Jennifer's Love Story
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Jennifer's Love Story
By Jennifer Rose
Here's my story; I wish that it were true. A certain select items are
true and I believe that you won't have a difficult time finding those
that aren't. (You may not believe me but Bruce's cock size is not
exaggerated.) Anyway, I hope that you enjoy!
Getting Started
I had just turned 12 when we met. I was a thin boy with longish dark
brown hair. I was pretty plain looking but definitely not ugly. I
wasn't sexually active and honestly didn't think a whole lot about it,
I guess because my parents basically forgot to teach me the facts of
life. I spent most of my time alone reading books and playing video
games. Being very shy most of the kids thought I was a little strange.
I was a latchkey kid and for the most part only saw my folks on the
weekend. My father was always traveling and my mother usually worked
the night shift.
One weekend my mom finally got tired of hearing me say how bored I was
so she got me a job. She knew someone who knew someone who ran his own
small business that wanted someone to take on all of the administrative
things he didn't have time for. He worked at home and it was only a
few blocks away. My family was definitely not poor but when I pulled
my bike up to this mansion I felt like my family lived in a shack! It
was an absolutely beautiful home on about 10 acres. I rang the bell at
the gate and after a minute I was buzzed in. I didn't realize it but
there was a hidden camera so you could see who was there before you
buzzed them in.
I rode my bike up to the house and realized that I had no idea what to
expect. I didn't know anything about the guy or what he did. This
actually made me nervous and I had to fight hard not to turn around and
go back. I set my bike on the ground near the front door and slowly
walked up the steps. Before I had a chance to knock the door opened
and a good looking tall muscular man of about 35 stepped out. He had
brown wavy hair and was about 6' 4", well above my small 5' 4," 100
pound frame.
"Hi, you must be Jim Smith. I'm Bruce Rose," his voice boomed in a
loud friendly manner.
Looking at the ground I managed to whisper, "Hi."
"I heard that you were a shy one," he laughed. "Come on in and let me
show you around," he said as he put his hand on my shoulder and led me
through the door.
I looked up and saw how huge the entry room was. It had a huge vaulted
ceiling and was about the size of a medium size home. There was a
spiral staircase leading upstairs. I won't bore you with the details
but the house had 5 bedrooms, a pool room and a home theater and it
took him about an hour to show me through the house and around the
yard. He was such a warm friendly person that I began to feel a little
comfortable with him after about half an hour, much less than my normal
week or two.
The last stop was the office. Like everything else it was huge. There
was a smaller desk with a computer by the entry way. That was where I
was to sit. He had me sit in the chair while he sat on the desk and
explained about the job. He dealt in real estate. He would buy all
sorts of properties, have them fixed up and sell them for a very large
profit. He traveled infrequently but was sometimes gone all day
looking at properties. However, most of the time he was in the office
coordinating everything. He had little time for taking notes during
his calls, filing paperwork and so on. He wanted me to work at least 3
days a week after school for a few hours each day. However, if I
wanted to work more than that he was all for it. Since summer vacation
had just started and I had nothing to do I worked every day for about 8
hours each day.
He was impeccably groomed and dressed so I asked him what I should
wear. Since clients would come by periodically he wanted me to have
some nice clothes for those days. Since he never knew until the
morning of the day they were coming by he said that he would purchase a
couple of outfits and I could come in my jeans and a t-shirt and change
into better clothes at work if I needed to.
He led me outside so we could get to know one another. I told him
about myself and he told me that he had a brother and sister. He was
divorced after being married for 5 years. His wife just took off,
leaving everything behind, even her jewelry. For him that was enough
of dealing with women and he decided to bury himself in his work. He
was so friendly I was shocked that someone would leave an attractive,
wealthy, seemingly very nice man.
We went back to the office and he showed me around. Pretty soon it was
5 PM so we said goodbye and I rode my bike home. I would have to say
that I was pretty happy. For some odd reason one of the things that I
kept thinking about was how good looking he was and how it felt nice
when he had his hand on my shoulder.
Changes
Over the next month I became more comfortable around him. He really
was a nice guy and he seemed to become better and better looking each
day that I saw him. I was excited to get to work every day. One day
about 5 weeks into the job I put on old jeans and a t-shirt and rode my
bike to work as fast as I could. When I got there I was worried when
he looked at me. "I must have just missed you at home. I tried to
call to tell you that a client was coming by and I needed you to take
notes so you needed to dress nice." I felt terrible and got really
nervous that he was mad at me. "Hey, don't worry we'll work something
out."
He led me to one of the rooms upstairs. "I hope you don't mind but my
clothes definitely will not fit you but my wife was about your size and
she has some clothes that could be worn by a guy or a girl." For some
reason I didn't mind, in fact I started to get excited about what it
would feel like. Bruce rummaged through the huge walk-in closet.
Eventually he came out with a pair of black slacks and blue button down
shirt. He left the room and I got changed. The pants fit fine and so
did the shirt. The odd thing about the shirt is that the buttons were
on the wrong side. I figured that this must be a defective shirt and
didn't say anything about it. I realized that I needed a belt so I
ventured into the closet to find one. I passed row upon row of
dresses, other clothes and shoes. Again I found myself becoming
aroused at the sight of all of these pretty things. His ex-wife seemed
to have very good taste. I can't imagine what some of these clothes
cost. I finally found the belts hanging in the back of the closet.
There were so many that it took a while to actually find one that
wasn't too feminine. On the way out I ran my hand along the clothes
and felt very excited by the silky texture of many of the items.
I heard the buzzer for the front gate go off and started to get
nervous. What if this guy found out? However, looking in the mirror I
relaxed because there really was no way to tell that I was wearing
women's clothing. I made my way back to the office and forced my
shyness to the back of my head. I realized that I would not last in
this job if I couldn't get over my shyness. Bruce was with an older
man in his office when I came in. Bruce gave me a big smile and
introduced me to his client. I pulled a chair up next to Bruce's desk
and began to take notes. It was perhaps the most boring 60 minutes of
my life.
As Bruce showed his client out I sat at my desk and transferred the
notes to the computer. Bruce returned and placed a hand on my shoulder
and gave it a little squeeze. "Thank you so much Jim. I know that
it's boring but it really saves me a ton of time." As he walked away
he said, "Oh, and by the way, you look great." For some reason I
turned bright red. I went back to work wondering why I was so
embarrassed. Throughout the rest of the day it never crossed my mind
to change clothes. I would also look up at times and see Bruce looking
at me. He would smile and turn back to his work.
At five I was getting ready to leave when Bruce reminded me of the
clothes. I was so embarrassed that I had forgotten to change that I
ran upstairs without looking at Bruce and changed. Bruce was waiting
for me when I got down. "Don't worry; this weekend I'll pick up a
couple of things for you to wear." Once again he put his hand on my
shoulder and showed me to the door. I thought that I even felt him
give it a little squeeze.
I dreamed of Bruce that night and of wearing his ex-wife's clothes. I
couldn't wait to get back to Bruce's. The work was boring but I found
that I really enjoyed being around him. It was a rainy day. I rode my
bike to Bruce's as fast as I could but my clothes were soaked by the
time I got to his house. "You should have called and I would have
given you a ride," he said. He showed me upstairs and had me shower in
what must have been his ex-wife's bathroom. It was pretty and pink. I
came out of the shower smelling like flowers since the only soap had
perfume in it. There were some clothes piled in the bedroom and a note
on top.
"I'm washing and drying your clothes. I'm sorry but this was the most
masculine stuff I could find. Sorry about the panties but your
underwear was soaked. You don't have to wear them if you don't want."
There was a pair women's jeans, size 2, a powder blue polo shirt and a
pair of white silk panties that were, I found out later, Brazilian cut.
They seemed to crawl between my butt cheeks. I really didn't think
twice about putting them on since I always wore underwear and didn't
think that it would feel comfortable wearing jeans without a pair of
underwear on. And I must say that the silk felt very nice. The jeans
fit quite well even though they were a little wide in the hips. They
also crawled up between my butt cheeks and when I looked in the mirror
I found that these were the first pair of pants that I had worn that
made it look like I had a butt at all. In fact it looked like a cute
little bubble butt. The polo shirt was rather short so that you could
see my belly when I raised my arms even a little bit. The sleeves were
also very short and a little puffy and just barely covered my
shoulders. Again the buttons were on the wrong side. I figured his
wife must have gotten a lot of clothes that were irregulars.
When I was dressed I looked in the mirror and was surprised at how
pretty I looked. Like I told you I was a pretty plain looking boy but
for some reason the color of the clothes and the fact that my hair was
getting rather long made me look like a pretty cute young girl. I
should have been terrified to go downstairs and have Bruce see me but
for some reason I wasn't. I practically bounded downstairs and into
the office. Bruce was rummaging in a file cabinet behind his desk. He
didn't look up when I came in but said, "Hey, I'm sorry about the
clothes but that's all I could find. I hope you don't mind wearing
them for an hour or so until your clothes are ready."
"I don't mind at all," I said.
He looked up when I said that and when he saw me he gave me a big
smile. "Don't be offended but you look great in those clothes," he
said with a smile.
"Thanks. Don't worry, I'm not offended. In fact I can't remember the
last time that someone told be that I look great."
With that I sat down and began to work. I seemed to feel his eyes upon
me the entire day. Rather than make me uncomfortable I became very
aroused and kept thinking of Bruce. Like I said earlier I wasn't well
versed in the whole sex education thing but I wasn't stupid either. I
knew that many people frowned upon men being with men but my family
wasn't one of those. I had an openly gay uncle who was very
affectionate with his lover at family gatherings and nobody raised an
eyebrow. Still, I had a hard time thinking that I might be gay. At
lunch time Bruce came to my desk and snapped his fingers to rouse me
from my daydream.
He puts his hands on my shoulders and said with a laugh "I hope you
were dreaming of something nice." I turned bright red and apologized
for not focusing on work. He said that he didn't mind and offered to
take me to lunch. I agreed and we went to the garage where he led me
to his Lexus convertible, a $70,000 car! He even held my door open for
me. We drove to a local sit down restaurant and it wasn't until we got
out that I remembered that I was wearing his ex-wife's clothes!
"Oh my God, I forgot to change!"
"Oh, don't worry about that. You look fine. Nobody will be able to
tell either way," he said as he took my hand and led me into the
restaurant. I couldn't believe he actually held my hand! My hand
began to sweat profusely from both the nervousness of being in girl's
clothes in public and holding the hand of a man that I was becoming
increasingly attracted to. We were shown to our table and when we sat
down Bruce grabbed his napkin and dried his hand. I was so
embarrassed!
The waitress came and I was shocked when she said, "What would you like
to drink miss?" I turned even redder if that was possible and without
looking up I ordered a coke. Bruce did the same and when the waitress
left he took my hand again and said, "Don't turn so red or she may
realize you're a boy and then wonder why you're wearing girl's
clothes." I hadn't thought of that and quickly tried to compose
myself.
The rest of the meal went by okay. When we were done eating the
waitress came by and dropped off the check and made small talk while
she cleared the plates. "So, what sort of father daughter activities
do you two have planed for the day?" I could have died! Bruce winked
at me and said, "I have a feeling we'll go clothes shopping, that's all
she ever wants to do." The waitress laughed and said, "You're a lucky
girl; my father would never take me clothes shopping. Well I hope you
two have fun!"
She left and Bruce paid the bill. "Come on sweetheart, let's get
going," he said with a big grin. With that he took my hand, led me to
the car and held the door open for me. When he got in he put his hand
on my knee and said, "God that was fun!" I actually had to agree. We
laughed about it all the way back to work.
I couldn't believe it but I was developing a crush on this man. Since
he had been married he obviously was straight. I did begin to wonder
though if he wouldn't mind being with a guy dressed as a girl. I mean,
he obviously liked the way that I looked. I could feel his eyes on my
butt whenever I walked away from him and he was definitely looking at
me whenever I reached into a tall file cabinet and my shirt lifted up
to show my belly.
Sadly the work day came to an end and I went upstairs to change. I got
a little nosy and walked into the closet to get a better look at the
kind of clothes his wife used to wear. Bruce obviously wasn't lying
when he said that he could find much in the way of non-feminine
clothes. The things that this woman had would put every girl I had
ever seen to shame. She was the ultimate in femininity. There were
all sorts of pretty dresses and skirts of every length. Beautiful silk
blouses and many camisoles were to be found. Most of the slacks were
the length of Capri pants.
Sadly Bruce was to be out all day the next day so I wouldn't get to see
him but I had plenty to do so he gave me the code to let myself in. I
got to work but after about 15 minutes I couldn't help myself and went
back to the bedroom. This time I looked in the dressers as well and
found all sorts of beautiful lingerie. On impulse I stripped down to
nothing and put on a pretty white thong and black camisole. The
camisole had some padding in it so it looked like I was just beginning
to grow a chest. Next I went to the closet and found a pretty white
business suit with very feminine fluttery silk around the jacket and
bottom of the skirt. I also found a pair of 2 inch white heels that
looked good with the suit. My legs were basically hairless so although
they were quite skinny they looked pretty darn good. I felt wonderful!
I went down to the office, sat at my desk and began to work. I was so
aroused by the clothes that I realized I was playing with myself. I
have had wet dreams before and almost every night since I met Bruce but
have never played with myself. Everything just felt so good that I
couldn't help myself. I grabbed some tissue and put them in my panties
so as not to make a mess of my clothes. Between the feeling of the
clothes and thinking about Bruce I didn't last long.
As you probably guessed I lost track of time and didn't hear Bruce
enter. I have no idea how long he had been standing at the entry way
to the office but he obviously saw what I was wearing. He startled me
when he said, "If you dress in clothes that sexy every day I won't be
able to get any work done." I turned 10 shades of red when I heard him
and ran past him out the door and upstairs to change. I began to cry
from the embarrassment and hoped that he would be gone and I could
slink out the door never to return. Unfortunately I didn't even have a
chance to begin getting undressed when he knocked on the door.
"May I come in?"
"Please no, I don't want you to see me like this," I pleaded.
"Please don't be embarrassed. I'm not mad and I'm not offended I just
want to talk."
"Can I change first?" I asked.
"I'd rather you didn't. I think you look great and I'd like to see you
dressed like you were."
He sounded so sincere that I relented and told him that he could come
in. I looked down at the floor when he entered. I felt him sit on the
bed next to me and he put his arm around me. I was surprised and happy
when he pulled me in for a hug. "I'm so embarrassed," I said into his
big strong chest.
"You have no need to be embarrassed. I can't believe how you look.
Have you done this before?" he asked.
"Never," I replied. "It wasn't until yesterday. For some reason
wearing those clothes made me feel really good. I also liked how I was
treated by you and the waitress. Nobody has ever paid that much
attention to me."
He lifted my chin with his hand and looked my straight in the eyes.
"You know," he said, "it's been a long time and it would be nice to
have a girl around the office. How would you like to work dressed like
this, provided we don't have any clients coming by?"
"I don't know, maybe. Are you sure I look okay?" I said meekly.
"You look absolutely incredible!" he exclaimed. "We do, however, need
to come up with a name. Can you think of one?"
"No," I said. I really couldn't. This isn't something that I had ever
thought about.
"Well, I love the name Jennifer," he said. "It's a pretty name and it
would befit a pretty, young girl. What do you think?"
"Okay," I said. I think that I would have said okay to anything at
that point. I was a mixture of nervousness and relief. In a short
period of time I had changed dramatically. I began to wonder if maybe
this was fate. Although I never consciously thought of this it just
happened and I was happy about it. "Thank you," I said and I wrapped
my arms around his neck and we hugged. His hug was strong and
comforting.
"Well Jennifer you'd better get changed," he said. "I want you here
bright and early tomorrow so you can get changed in time for work." He
patted me on the knee and gave it a little squeeze and left. I
reluctantly changed and rode home.
Flirtation
I got to work about 30 minutes early the following day. I would have
gotten there two hours early because I was so excited but felt that 30
minutes would be enough time. I let myself in and went to the office.
Bruce wasn't around but there was a note on my computer saying that he
had laid some clothes on the bed for me to wear. I bolted upstairs and
found a note on top of some clothes. The note read "Good morning
Jennifer. I hope you like the clothes that I picked out. Feel free to
put on any jewelry that you would like. There's makeup in the bathroom
that you can use as well."
Bruce had picked out a pretty, white suit. The jacket was cropped and
the slacks were cropped as well. There was a dark pick scarf like belt
with the pants. He had forgotten to include a blouse so I went to the
closet. After a while I found a pink silk and lace camisole that
matched the belt. I put on a pink thong thinking it should match the
camisole but I found that I could see it through the fabric of the
pants so I opted for a white thong instead. I got dressed and I must
say that I looked very pretty. I put on a pair of white heels and
found a necklace and matching bracelet to wear. I did my best to brush
my hair into a feminine style. Obviously I needed to grow it out a bit
more. I was afraid to try too much makeup since I had no idea what I
was doing. I put on some lip gloss and a bit of eye shadow. All in
all I think I looked like a fairly attractive 16 year old girl rather
than a plain looking 12 year old boy.
I made my way to the office and the closer I got the more nervous I
became. Yes, he was encouraging me to do this but I was so afraid that
he would think that I looked silly. His opinion had begun to mean so
much to me since I was developing a real crush on him. I meekly poked
my head around the door. Bruce, sensing my presence called out,
"Jennifer, great to see you!" Well this gave me a quick boost of
confidence so I walked into the office.
Bruce said, "My God, you look great. Turn around so I can get a better
look at you." So, I walked in a little further and turned around and
walked away. Bruce let out a wolf whistle that made me turn red.
I turned back around. "Thanks Bruce. Are you sure I look okay?
"Jennifer, you look so pretty I'm going to have to pick out plainer
clothes for you or I'm not going to get anything done!"
This really boosted my confidence. I decided to play it up a bit to
see where this might lead. "Thanks. Tell me," I said as I turned
around, "the material of these pants is really thin. Can you see my
panties?"
Very hesitantly Bruce said, "Um, no."
"Good," I said, "because I'm wearing a thong. I think that it gives my
butt a little more definition. Do you agree?"
Bruce paused again. "Yes, it looks very nice," he said this in a very
nervous voice which both raised my hopes and worried me that I had laid
it on a little thick.
"Well, we'd better get to work, there's a lot to do today."
We worked quietly throughout the day. A couple of times I had to ask
Bruce a question. When I would go to his desk and bend over to point
something out on a piece of paper I could swear he was looking down my
camisole. That made me chuckle because I had no boobs. I also felt
his eyes on my butt whenever I would walk away. Of course I would also
give my butt an extra wiggle.
I was really enjoying wearing the clothes; especially the thong. It
was a continual reminder that I was wearing clothing meant for a girl
which started to bring out my feminine side.
Eventually the day ended and I had to change and leave.
"I'll see you tomorrow Bruce. Will you have something else picked out
for me to wear?"
"Of course I will Jennifer. Tomorrow's Friday so I'll find something a
little more casual."
I absolutely could not wait until the morning. I had a wet dream about
Bruce over night and was desperately hoping that it would come true
someday, hopefully soon.
I got to work about 45 minutes early. I wanted to spend a little more
time on my makeup today. Bruce had picked out a pair of really cute
Capri jeans and an off-white silk camisole. Obviously he liked Capri
pants and that was fine with me. They looked simple but there was
something kind of fun about wearing them. It's really a feeling that I
can't describe, I just know that I like it. He obviously liked seeing
me in a camisole as well. I did like how they looked on me. I really
had skinny arms and legs even for a 12 year old. I guess it's because
I never was active in sports because I was too thin and nobody would
pick me at school when everyone played. Again I wore a thong and was
very happy with how my butt looked in the pants. I figured I wouldn't
make a comment to Bruce again because he seemed a little uncomfortable
when I did it the first time.
My hair was long enough that I could put it in a short ponytail. I
placed it high on the back of my head so it stood out a little more. I
fastened it with a white hair clip. I must say that it looked pretty
cute. I had gone to the mall the night before and checked out the
girls about my age and how they wore their makeup. I figured that I'd
give it a try. For the most part they wore lighter shades of eye
shadow and bright pink lip gloss. It took me a bit of time to put it
on but I was pretty pleased with the results, being a beginner and all.
I finished up with a necklace, one of those hair scrunches that a lot
of the girls were wearing as bracelets and a pair of small dangling
hoop earrings. No, my ears weren't pierced at the time. I bought a
pair of clip on earrings at the mall. I didn't have the guts to go
through with the piercing yet although a lot of guys at school had both
ears pierced. I didn't think my mom would mind but I didn't want to
surprise her so I figured I'd wait and ask her first.
I ran downstairs and when Bruce saw me his said, "Oh my God, you look
just like a sweet little 12 year old girl!"
"Thank you," I said as I walked to my desk.
Bruce came over and kneeled down beside me to show me what to work on.
He was very close and I was getting excited as I felt his breath on my
neck as he talked. I got even more excited when he put his hand on my
knee. When he was done explaining what I had to do he looked at me a
said, "You've worked hard this week so you can knock off at lunch
time."
"Okay," I said as I tried to hide my disappointment. I was really
enjoying wearing my clothes and with the weekend coming I knew that I
would have to be in boy mode for 2 straight days which really bummed me
out.
However, I really brightened up when Bruce said, "Don't be disappointed
sweetie. If you want to stay I've got a surprise for you. You can
also come by this weekend and just be a girl and not have to work."
Oh my God, he wants me to come by on the weekend! Then I realized that
he had called me Sweetie!
"That would be great!" I exclaimed. His face was so close I wanted to
kiss him. There was an uncomfortable silence as we looked into one
another's eyes. I broke the silence by saying with a big smile "Do you
call all of your employee's sweetie?"
This time it was his turn to turn bright red. "I'm sorry Jennifer,
it's just that you look like you could be my daughter, or niece anyway,
and I call my one niece sweetie. Don't worry I won't do it again."
"Darn. Does that mean that I can't call you Uncle Bruce, or better yet
daddy?" I asked with as cute a pouty face as I could manage.
"Well, I can't say that I wouldn't enjoy it! Okay sweetie, you can
call me daddy if you'd like."
Without thinking I threw my arms around his neck said, "Thanks daddy,"
and gave him a kiss on the cheek! I think that this shocked us both.
We gently pulled apart. Both of us were a little red. However, Bruce
made me feel better by giving my knee and squeeze and saying, "Okay,
let's get to work sweetie."
The next few hours seemed to take forever. I tried to get up as much
as possible and get into positions where Bruce could see my butt. Not
being a girl I knew that was about the most exciting part of my body
that I could use to flirt with him. He sure did seem to like it
because he kept his eyes on it every time he thought I wasn't paying
attention.
At close to Noon he said, "How about you call it a day?" I agreed.
Bruce then told me to come with him. He took my hand and we walked
into a room that I had never been in before. It was set up with a
stool and a camera. Bruce asked me to have a seat and I nervously
walked over to the stool and sat down. "I need to take a couple of
pictures of you for your surprise." Although I was nervous I sat and
smiled. Bruce took about 20 pictures with me making all sorts of
different faces.
When he was done he said, "Okay sweetie why don't you go into the
kitchen and get yourself something to eat while I get this taken care
of," I said okay and got up and went to the kitchen.
I knew what he liked to eat so I made lunch for the both of us. I
called out when I was done but Bruce told me it was going to take a
while longer. I asked him if it was okay to change into a different
outfit and he enthusiastically agreed.
I ran upstairs and decided that I wanted to put on something even
cuter. I had seen a bunch of miniskirts in the closet so I looked
through them and found a really cute white pleated one that came to
about half the way to my knees. There were some shorter ones but I
didn't want to go that far just yet. I also picked out a cute little
light pink crop tank top. I wanted to have a chance to wear a bra and
this was perfect.
Just as I finished up he called out so I ran down to the kitchen and
got our lunch. It was fun to run in a miniskirt! With each step it
flew up although I don't know if it was far enough to see my thong.
As I walked into the room I said, "Here's your lunch daddy." He was
sitting at my desk and said, "Thanks sweetie," without turning around.
When I brought the lunch to my desk I kneeled down next to him, placed
my arm on his leg and kind of snuggled up to him. Without looking at
me he absentmindedly placed his arm around my shoulders and pointed to
the screen. "Here's your present baby. It's a virtual makeover kit.
I put a couple of pictures into the program and you can experiment with
different looks. What do you think?" he asked.
"Oh my God that's neat! I've been so worried about putting on makeup
because I didn't want to look silly." He glanced down at me with a
smile when I said that and his eyes got huge. "Um, that's a really
cute outfit."
With that I stood up, backed away and gave a little twirl. "Are you
sure? My legs look so skinny in this."
"Some men like skinny legs," he said quietly.
"Are you one of those men?" I asked with a very innocent voice.
"Yes," he said. Again he said it quietly and without looking at me.
Instead he was looking at my legs and the way he was shifting in his
seat I think that he was starting to get hard!
"Goody," I said. "Can I play now?" I asked.
He was kind of in a trance staring at my legs but he visibly snapped
out of it and said, "Sure, come have a seat and I'll walk you through
it." I was hoping that he would pat his lap. God, what I wouldn't
give to sit on his lap! But instead he shifted off the seat and
squatted onto the floor right next to the seat. I bounded over knowing
that my skirt would fly up a little. It did but not as much as I
hoped. I plopped down on the seat and my skirt flew up a little so it
was creased under my butt and a little uncomfortable to sit on. Of
course Bruce was watching all of this and his face was no more than a
foot away from my butt as I lifted up a little and smoothed the skirt
out before sitting down again.
Bruce placed his arm along my leg and his hand rested on my knee as he
walked me through how to use the program. I worked the mouse according
to his instructions. However, I would sometimes purposely move the
pointer to the wrong spot. This would cause him to place his hand over
mine and move my hand and the mouse to the right spot. We spent almost
half an hour doing this. Finally Bruce gave my knee a squeeze and said
that he had to get up because his knees were killing him. "Oh, you're
not that old daddy," I said as I placed my hand on his trying to keep
it on my knee for as long as possible. He paused and looked at me with
a smile before getting up and saying, "Have fun baby and call me when
you're done so I can take a look."
I was sad to see him go but also excited to play with my new toy. I
set about trying a bunch of different styles. It took me a couple of
hours but I found about five I liked and got up to stretch my legs a
bit. I found Bruce outside sitting on a two person chair. He had
changed to shorts and was reading a book. As I walked out he looked up
and patted the chair. "Have a seat and tell me how things are going."
I sat down with my feet off to the side away from Bruce. This caused
our thighs to be rubbing against one another. His tan strong muscular
legs had just a hint of hair and were at least twice the size of mine.
"It's going great!" I exclaimed. "I have a few ready to show you."
"Great. Let me finish my drink and we'll go take a look at them," he
said.
"It's chilly out here in a miniskirt," I said half lying. He did as I
hoped and put his arm across my back and pulled me close. "Thanks," I
whispered into his chest.
We sat in a comfortable quiet as he sipped his drink very slowly as if
to make the moment last forever. Finally he said, "Okay, let's go take
a look at what you've done." We got up and he put his arm around my
shoulder and hugged me close as he led me back to the office. I sat
down in my chair and again he squatted down beside me and placed his
arm along my leg with his hand on my knee.
We looked through the pictures and he made comments about each one. I
made a couple of changes based on his suggestions. Finally we heard
the grandfather clock chime 6 o'clock. We had completely lost track of
time. Bruce said, "You'd better call your mom, change and head home
young lady." I reluctantly agreed and before I could stand up he
looked deep into my eyes and said, "Would you still like to come by
tomorrow and spend the day with me? Maybe you can try out your new
looks."
"Oh that would be great daddy!" I exclaimed and jumped up and gave him
a hug.
We hugged tightly for a minute or so before he took my shoulders and
looked down at me and said, "Okay, how does 9 o'clock sound
sweetheart?" he said with a grin. I agreed and then bounded away up
the stairs and into my bedroom to call my mom and change. I started
referring to it as my bedroom since I was the only one that used it and
it is where I kept all of "my," clothes.
The Beginning
I left quietly and rode my bike home. My mom was there when I got
there and it was a rare occasion that she had actually made dinner.
Dad hadn't returned home yet so I talked with mom while we ate. I told
her all about work and Bruce. She must have noticed the way that I
looked whenever I mentioned him, which was a lot. As we cleaned up the
table all I talked about was Bruce. Of course I didn't notice but my
mom sure did. When we were done mom told me that we should talk. I
was a little nervous as we walked into the living room.
She sat next to me on the couch and said, "Is there something else that
you want to tell me about Bruce?"
"What do you mean?" I asked innocently.
"Well, you obviously have grown to like Bruce a lot. He's about all
you've talked about since you got home. Don't get mad if this isn't
correct but it looks to me that you have a crush on him." I turned
beat red!
"I guess," I said after a moment. I was afraid that my mom was going
to be livid. Instead she said, "You know, you're only 12 and this man
is old enough to be your father."
"But dad's old enough to be your father too!" I exclaimed. Of course
I was right but then again mom was 20 when they started dating.
"Have you and Bruce done anything yet?" she asked. I assured her that
we hadn't and that Bruce hadn't even tried. "Does he feel the same
way?" she probed.
"I don't know for sure but I think so. We've had a couple of moments
where we've looked deep into each other's eyes. I've also caught him
staring at my butt a few times."
Mom laughed at that. "Well, given your age difference I think that
you'll be the bottom in this relationship!" I didn't know what that
meant so I asked.
She looked surprised for a second and slowly looked sad. "I guess your
father and I are so busy we've neglected to tell you about the birds
and the bees. I'm so sorry." I assured her that I didn't mind and I
had learned a lot about it already. "Well," she said, "let's get
started." She began to talk about sex and asked about what I did and
did not know. Where I was ignorant or fuzzy she went into detail,
sometimes graphic. It was strange but I wasn't at all uncomfortable.
Next she went on to gay sex. Since her brother was gay she knew quite
a bit about it. She had skipped oral sex during the first part of the
conversation but explained it now. I asked her what happened when the
man came and she gave me one of three options. I could finish him off
using my hand, I could finish him off using my mouth and spit it out or
I could finish him off using my mouth and swallow. This last one
surprised me. "You mean some people actually swallow cum?" I asked.
"Yes," she replied, "Some people don't mind the taste and others
actually enjoy the taste." Lucky for me she didn't tell me her
preference!
Next she moved on to anal sex. I was so naïve that I was shocked by
this. "You mean men actually put their penis in the butt of other
men?" She even went so far as to tell me that men did it to women in
some cases as well. Again I was glad she didn't tell me if she had
done it but she did say that many people actually enjoyed being fucked
in the butt. "Is this what you mean by being a bottom?" I asked.
"Yes," she responded. "And from what you tell me about the two of you
if you do have sex with Bruce be prepared because I'm pretty sure
you'll be on the bottom. I guess that's a sure fire test as to whether
or not you're gay." I don't think that she expected me to answer but I
said, "I sure wouldn't mind finding out!" I turned beat red when I
realized what I had said. She just smiled and let it go.
"Do bottoms dress up as women?" I asked without thinking. She looked
at me intensely. "Some do, but most don't." After a second she asked
"Do you want to?" "I don't know," I replied. She just stared at me so
I decided to tell her what happened. She wasn't happy or angry. She
did, however, tell me that although she would tell dad about my
feelings towards Bruce she wouldn't mention this. "For some reason
this is a larger taboo than being gay. I'm not sure why but it is."
"I'll level with you," she said. "I lost my virginity at 14 to an
older man. It wasn't rape but I thought it was love. We dated for a
while, secretly of course. I'll be honest with you, it was great. He
was very gentle and caring. Although it hurt when we stopped seeing
one another I wouldn't trade the experience for the world."
"So you're okay with this?" I asked.
"Well, it would be pretty hypocritical of me if I said that I wasn't.
I'm not ecstatic about it but I'm not against it," she said. That was
good enough for me and I thanked her and we hugged.
"He wants me to go over tomorrow and just hang out," I said. She
looked a little concerned but told me that it was okay.
Just then my father pulled up. We greeted him and realizing how late
it was my mom sent me to bed. I pretended to go to bed but didn't.
Instead I hid where I could hear them talk. It started with the
typical "how was your week?" This seemed to take forever. Finally mom
got around to telling dad about my feelings towards Bruce. I was
pleasantly shocked when I heard him say that he wasn't surprised I was
gay! He said he had had an inkling ever since I was young. "Well", he
said, "maybe now he'll be able to make some friends. It's sad to see
him spend so much time alone."
I woke up early the next morning and was surprised to find dad eating
breakfast. Normally he slept in late on weekends. I poured some
cereal and sat down at the table. He put his paper down and told me
that he had spoken with mom and that he was okay with my lifestyle
choice. However, he wasn't too sure about the fact that I had a crush
on someone so much older than me. He wanted to meet Bruce and
suggested that I invite him over for a barbeque on Sunday. I told him
that nothing had happened and may never happen and that Bruce didn't
even know about my feelings for him. Dad assured me that he wouldn't
spill the beans. He said that we could make it look like a thank you
for giving me a job. I told him that I would ask Bruce and call home
if he agreed to attend. With that I left to clean up and head to
Bruce's.
When I got there I ran right up to my room. He hadn't laid out any
clothes but had placed a note on the dresser that said, "Jennifer,
You're a big girl now :) so why don't you pick out an outfit yourself.
I'm sure you'll look great." And it was signed "Love Daddy". I was so
excited!!! Bruce had printed out in color all five of the looks that I
had chosen. Since it was a bright sunny morning I chose the light pink
combination. Bruce had seemed to like this one best. It took me what
seemed like forever to get the makeup right but when I finally did I
looked great! Just like in the picture from the computer program it
had the effect of making me look like I was about 10 or 11. I wondered
if that was why Bruce liked this one so much.
Next I picked out my outfit. I think that his ex-wife either kept all
the clothes she wore when she was young, really was young or liked to
dress that way. Whatever the reason I loved her taste in clothing.
First came the obligatory thong; this one in pink. I followed this
with a pair of small white shorts with a 1 ½ inch inseam. This allowed
him to see not only a lot of my legs but my butt as well. I really
liked these shorts because they made it look like I had a pert little
butt. This had become very important to me now that I knew what a
bottom was and I wanted him to fantasize about sticking his cock in it.
To heighten his interest the shorts were also the low rise kind so if I
squatted down you could see that I was wearing a thong. Next came the
top. I found a really cute short sleeved crop top. The outside was
pink and sheer and it had a lot of lace accents. Underneath was an
attached white camisole. I decided against stuffing my top since I
wanted to go with the very young look. I also decided to paint my
fingernails and toenails a sparkly pink. There was a pair of cute open
toed sandals that I wore so he could see that I painted my toenails.
Finally I put my hair up into its little ponytail using a pink ribbon
and put on a bit of jewelry.
When I was ready I ran downstairs to find Bruce. I heard him fumbling
around in the laundry room. He was loading some of his clothes in the
washing machine and I could see the clothes that I had worn and put in
the laundry chute. This didn't seem fair so I said, "Why don't you let
me do that daddy?" Bruce turned around and, "Oh wow, it looks like my
little girl is getting younger and younger. You look absolutely
adorable! Are you sure you're 12 and not 10?" I turned red and turned
around walked away a little and said, "So you like?" He quietly said,
"I guess this makes me sound like a dirty old man but I would have to
say that I like very much." This really made me smile.
I walked back into towards him and said, "Now you get out of here and
read your paper and let me take care of this. Most of these clothes
are mine." He gave me a big smile and I realized what I had just said.
"I'm sorry, they're not mine but they're clothes that I've worn." He
just laughed. "Well, I can never wear them so we might as well
consider them yours."
I then realized that this would be the perfect opportunity for me to
squat down in front of him. I did just that to gather the clothes up.
He just stood over me and stared down the back of my shorts. This was
great! It was having the exact effect that I wanted. I looked up at
him and said, "Are you just going to stand there staring all day or are
you going to go read your paper?" Boy did he turn red! "Sorry, I was
kind of drifting off there. Thanks for doing this pumpkin; I really
hate to do laundry." I smiled and said, "You can now consider it one
of my jobs. And thank you for calling me pumpkin, I really like that."
Bruce left and I went about getting the laundry started. I realized
that I always fought doing the laundry at home but I was kind of
enjoying this. Next thing you know I'll be cleaning his house for him
and liking it!
Once I got things going I found Bruce on the patio reading the paper.
Bruce heard me come out and patted the spot next to him. I quickly sat
down and snuggled into his shoulder. Two weeks ago I never would have
thought of doing that but it seemed natural now and I know that Bruce
enjoyed it. Bruce lifted his arm and put it around my shoulder drawing
me close. He looked down at me and said, "Thanks for doing that
pumpkin, you have no idea how much I hate it." He then kissed me on the
forehead! This wasn't one of those absentminded kisses but a long more
affectionate kiss.
"It's my pleasure daddy. I'll do it anytime you'd like. This house
also needs a cleaning. I'd be happy to take care of that for you as
well."
He looked at me and without thinking said, "Maybe you can wear the
French maid outfit my wife got for Halloween one year." He turned red
after he said it thinking that I might be offended. Instead I said,
"That would be fun."
There was a slight pause before he said, "So, what did you have in mind
for today sweetheart?"
Have in mind? I hadn't really thought of anything other than hanging
out all day and trying on different clothes.
"Well," he said, "we need to do something. How about we go out for
brunch?"
I paused, a little disappointed that I would have to change. "Okay.
Give me a little time to take off the makeup and change into my other
clothes."
"Don't you dare," he said. "I will only take you out like this. You
could pass for my daughter without a problem. As long as you act
confident nobody will suspect a thing."
He looked dead serious and I didn't want to make him mad. If this is
what it took to get him to get into my panties than I would go through
with it. Plus he'd never ask if he didn't want to be seen with me.
"Okay, as long as we don't go to a place too close. The chance of
seeing someone I know would make me too nervous."
He agreed and we got up and left. He told me that he wanted me to hold
his hand whenever we walked anywhere and to refer to him as dad or
daddy. Well of course I had no problem with this!
Bruce drove to a restaurant in the next town. We had a wonderful time.
The waiter referred to me as miss and I actually felt quite
comfortable. On the way back home it started to cool down and
eventually it began to rain. So much for a warm sunny day. When we
got home Bruce decided we should watch a movie and maybe play a little
pool or something. I had never played pool before but he said that he
would teach me.
It had cooled off quite a bit and I knew that I had been laying it on a
little thick so I decided to change things up a little. I found a
really cute long sleeved pink sweater with a pink rose embroidered over
the left breast. Next I found a really cute blue jean miniskirt. This
ensemble was both cute and just a little sexy. I just touched up my
makeup. It would take me too long to completely redo it.
Bruce was in the media room when I found him. When he saw me he said,
"I can't believe it but it looks like my little girl has grown up fast.
I'm guessing 16 or so." Well, that was close enough to legal for me!
We decided on an action adventure movie. I can't remember which one or
even if it was any good! I cuddled up next to him and all I could
focus on was how big, strong and handsome he was. My miniskirt rode up
just a little so if he had been walking towards me he would have gotten
a little hint of panties. When he began rubbing my bare leg I almost
came in my panties! "That feels nice," I whispered into his big strong
shoulder. He didn't say anything but continued on, sometimes moving
all the way up my thigh to the bottom of my skirt. I also noticed a
distinctive bulge in his pants. I couldn't take my eyes off of it.
All I could think of was how huge it was. I mean, this thing must be
absolutely mammoth! It actually frightened me a little. I began to
wonder if I could even fit it in my mouth much less my ass.
As the movie drew to a close Bruce's rubbing trailed off and I noticed
his bulge getting a little smaller. I guess he wanted to make sure
that he could turn on the lights without me seeing what I had already
been watching for the past hour. I was thankful as well because my
hard on also went down a little. The miniskirt did a good job of
concealing it while I was sitting but I wasn't sure if it would work
too well while standing.
We got up and stretched our legs after the movie ended. I made a show
of stretching. I got on my toes and raised my arms above my head.
This caused the sweater to rise up so he could see most of my belly. I
changed out the laundry and then went upstairs to freshen up and
decided to change my jewelry. Bruce had asked me not to change my
outfit. I put on another necklace and as I was rummaging through all
of the jewelry I found a couple of pairs of clip-on earrings. I was so
excited! I went with a pair that had a bunch of gold hoops, each
smaller than the other. I thought that they were cool because they
jingled whenever I moved my head.
I bounded down the stairs mainly because it made my earrings jingle and
went to the game room. Bruce had already racked the balls and had made
himself a scotch and water. Good, I thought, maybe if he gets a little
drunk it will be easier to get him to take advantage of me. I asked
him to break since I didn't know what I was doing. He proceeded to
pocket a couple of balls. When he missed I took my cue and set up for
my first shot. Of course I did it all wrong. Bruce decided that he
should show me how to do it.
He came up behind me and told me to bend over the table to get eye
level with the cue ball. This was my chance to let him see my panties
full on. I bent over and lifted one leg to get further on the table.
I knew my skirt rode up high enough to see not only my thong but a
little bit of butt cheek. I think that this was too much for him. All
of my efforts had finally paid off. He came up behind me and
positioned himself along my back. His face was just off to my side.
As he took my hands and repositioned me I looked over to him. Our lips
were only an inch or two apart. "See, that's how you do it." He
whispered. It was too much. He was too close to do anything but kiss
him!
Our lips met hesitantly at first but slowly we got more and more into
it. Soon I felt his tongue along my lips. I joyously opened my mouth
for him and his tongue shot in. It was long and thick and filled my
mouth. We tongue wrestled for about a minute. It was a wet, sloppy
kiss. We were both in an uncomfortable position so without missing a
beat he rolled me over and picked me up. I wrapped my legs around his
back, my skirt hiked up high and without breaking our kiss he carried
me over and laid me down on the couch. My legs still straddled his
back as he began to gently dry hump me. We kissed eyes open and
looking deep into each others eyes for what seemed like an eternity.
Finally we broke.
"I'm sorry, I just couldn't take it anymore," he said.
"Don't be sorry, I couldn't take it either," I replied.
We kissed long and deep yet again. When we broke I looked into his
eyes and said, "Please, daddy, I want to see your body so badly."
Without saying a word he stood up and stripped. He towered over me and
I was amazed by his muscular almost hairless body. As he pulled down
his pants I sat up and kept him from pulling down his tight white
underwear. The bulge was fantastically large and at the tip the
material was wet from pre-cum. I gently lifted the waistband over the
tip of his cock and pulled down the underwear. I watched intently as
his huge cock was revealed. When I finally got his underwear down far
enough his cock fell down and hit me in the forehead. I looked up at
him and laughed. He, of course, had a huge grin on his face.
I took the monster in my hands and studied it intently. I was amazed
at the size and perfection. This was indeed something to be very proud
of. Finally I could hold back no longer and positioned myself directly
in front of it. Looking up at Bruce I kissed the very tip. Then I
stuck out my tongue and slowly, gently licked the tip. His pre-cum was
warm and salty; not at all what I thought that it would taste like.
Not bad, just different. I was sure that I could grow to love it. I
alternated between kisses and licks and soon moved to a full on tongue
bath of the tip of his cock. Next I opened my mouth to take in the
tip. It seemed strange to me how something so hard could be so soft
and velvety at the same time. I was practically drooling and looking
Bruce right in the eye the huge head penetrated my lips and about two
more inches went in. Bruce closed his eyes and let out a long sigh.
He obviously was enjoying being in my mouth. It was strange because I
was having difficulty getting him much further into my mouth. I only
got about 4 inches in before my mouth was stretched so wide I couldn't
get any more in. I sure hope my butt was more pliable! I began
bobbing up and down the shaft as far as I could. I noticed that I
could hear myself slurping and my earrings were jingling. This added
to the eroticism. I would sometimes stop bobbing and swirl my tongue
around the head. I also began to use my hand to rub up and down the
shaft. Since my mouth was watering so much there was plenty of
moisture to make things easier.
After about 5 minutes Bruce slowly pulled me off. I reluctantly let go
and looked up at him questioningly. "This is wonderful pumpkin. Let's
change positions because I'm going to cum soon and I don't want to cum
in your mouth." This confused me. "Why don't you want to cum in my
mouth?"
"Because," he answered "I never knew a girl that wanted me to cum in
their mouth. Besides, I cum a lot and wouldn't want to make a mess of
your outfit."
I didn't reply because I wanted to surprise him. There was no way I
was going to waste this wonderful man's cum. Why would any girl not
want to taste the fruits of her labor?
Bruce pulled me up and kissed me long and hard. I draped my arms
around his neck as his hands reached under my skirt and grabbed each
globe of my ass. I was on my tiptoes because he was so much taller
than me. I lifted my left leg onto his hip and he used this
opportunity to take the index finger on his right hand, slide it under
my thong and massage my butt hole. I shivered when he did that. He
began to pull his hand away but I moved it back letting him know that
the shiver was from pleasure not from fear.
Eventually Bruce moved his hands from my butt to my shoulders signaling
the end of our kiss. We reluctantly parted and Bruce said, "Jennifer,
I don't want to offend you but I would love to videotape this for
posterity's sake." How could I say no! This was to be my very first
time and I thought that it was rather romantic. I agreed and he ran to
set up the camera on a tripod. It was funny watching him run with a
hard-on. It bounced up and down and had to be rather uncomfortable.
When everything was ready Bruce proceeded to lie down on the couch; his
cock pointing straight up strong and hard. I got on my knees between
his legs so I could look at him while I sucked his beautiful tool.
I went back to my fun job and after about 5 minutes I noticed his
breathing getting heavier. Finally he said, "I'm going to cum
pumpkin!" And cum he did! I pulled off just in time and backed away a
little. I watched as first a small amount poured out onto my hand.
Then came a huge blast that must have shot 3 feet in the air! This was
followed by several more blasts. I watched the tip of his cock
absolutely mesmerized. When he finally began to trail off I looked up
to his face and there was a look of utter satisfaction. I also noticed
that his chest was just soaked in cum. Could there be over half a
cup's worth or even more? I vowed that someday soon I would find out.
"How was it daddy?" I asked as I continued to gently stroke his cock.
"Oh my God sweetheart, that was spectacular," he said through half open
eyes.
I looked down at my hand which was covered in a thick coat of cum.
Curious, I stopped stroking and brought it to my face. I took my index
finger and stuck it in my mouth. I closed my lips around it and pulled
it out taking the cum into my mouth. I swirled it around with my
tongue and finally swallowed. "Not bad," I thought. I proceeded to
lick the rest off of my hand. I was so focused on getting every last
bit that I hadn't noticed that Bruce was intently watching me with a
look of wonder on his face. I looked up at him questioningly. "That
was the sexiest thing I have ever seen," he said.
I smiled and turned bright red and then bent back over and began to
lick his cock clean. I would look at his cock to spot the next glob
and then look him in the eye as I licked it off. Once his cock was
clean I proceeded to lick his legs clean followed by his stomach and
chest. It took me a couple of minutes to finish. When I was done I
moved up to his face. I wasn't sure what he would do. Would he kiss
me after I ate his cum? My question was quickly answered as he kissed
me hard and deep. He once again brought his hands up under my skirt
and began rubbing my cheeks and gently probing my asshole with his
index finger. It only took a few seconds for me to cum. It was a
spectacular orgasm. My eyes actually rolled back in my head!
We continued to kiss for a few more minutes. Bruce rolled onto his
side, our legs intertwined. "Wow," he said with a big grin, "that was
incredible."
"I can't wait to do it again," I said. "That was a lot of fun!"
He began laughing hard. "I wish you could stay the night pumpkin," he
said almost as if asking if it was okay. "If you can't at least you
can come by again tomorrow."
Just then I remembered that my father wanted Bruce to come over
tomorrow. "I'd love to Daddy but I was supposed to ask you something
but I forgot to. My father wants to know if you can come by tomorrow
for a barbeque. He wants to thank you for giving me the job and wants
to get to know you." I was afraid that he would turn it down.
"Sure pumpkin. I just hope that he doesn't find out that I just robbed
the cradle with his kid. I guess I could go to prison for this."
"Don't worry sweetheart, he won't find out. I don't think that he
would send you to prison either since he got busted by my mom a few
years ago. He was having sex with the babysitter and she was only 14.
I don't know why my parents stuck together but they did."
We snuggled quietly for a while; sometimes sharing tender kisses. I
must have dozed off because I awoke with a start and noticed that Bruce
was gone. I got up and looked in the mirror over the bar and saw how
disheveled I looked. There was no way I wanted Bruce to see me like
this. Unfortunately it was too late because Bruce came back into the
room just as I was getting ready to leave.
"Pumpkin, your mother just called. She wanted to know when you would
be coming home. I hope you don't mind but I told her that I was hoping
you could stay for dinner. She said it was okay as long as you were
home by 11," Bruce said. "Oh, and I told her that I would be happy to
come over tomorrow. Your dad flies out late in the day so everything
will start at noon."
I was delighted, to say the least. Dinner with Bruce! What should I
wear? Remembering how terrible I looked I covered my face in my hands,
ran out of the room and asked him not to look at me. He laughed but
stayed behind.
Once I got out the door and out of sight I called back. "I'd love to
stay for dinner," I yelled. "What should I wear?"
"Let's do something romantic. Pick out a dress and we'll have dinner
here," Bruce said.
This was so exciting! A romantic dinner with Bruce and my first time
wearing a dress. I quickly ran upstairs to pick out what I would wear.
For makeup I chose the dark, sexy look I had made with the makeover
program. In the picture this made me look like I was maybe twenty.
Next came the dress. She had so many to choose from! I decided on a
little black dress as this seemed to be the best choice for a romantic
dinner. There must have been 20 of them in the closet. Some were
extremely short and tight, some looked almost liked ball gowns. I
found an absolutely beautiful black dress. It had a single strap over
the left shoulder and came down to my knee on the left side and my
ankle on the right. It was form fitting but not too tight. Best of
all it was backless. It was the epitome of pretty with just a hint of
sexiness. Given the style of the dress I couldn't wear a bra but the
dress had push-up forms that gave the appearance of having at least a-
cup breasts. I went with a black thong, of course!
Once I picked out my outfit I hopped in the shower. I had found a
razor and used this to remove what little body hair I had. When I was
done I did my best to style my hair in a sexy up-do. I was past due
for my normal haircut and since my hair was already a little long to
begin with I was able to do a halfway decent job. I worked on my
makeup and nails. I was surprised that in such a short period of time
I was able to do an admiral job with my makeup. I chose a deep red
nail polish for my fingernails and toenails. I finished dressing with
a pair of black strappy sandals with a 3 inch heel. I didn't go
overboard on the jewelry. I chose a pair of diamond dangling earrings.
I vowed to get my ears pierced as soon as possible because the number
of clip-on earrings was limited but these were absolutely beautiful. I
also found a matching necklace. It was a gold chain with a single
teardrop diamond. Next came a tennis bracelet and a pretty gold ankle
bracelet. I didn't know it then but I was wearing about $50,000 worth
of jewelry at the time!
I was just finishing up when Bruce knocked on the door. "Hey babe, are
you about ready?"
I looked at the clock and realized that I had been getting ready for
over an hour! "I'm sorry honey I didn't realize how long this was
taking! I'll be right down." After a quick check in the mirror and a
tiny spray of perfume I opened the door. Bruce must have heard me
because he was standing at the bottom of the spiral staircase.
Bruce let out a wolf whistle that echoed in the cavernous entry room.
I blushed and made my way down the stairs. I couldn't help but notice
that Bruce was looking at me like I was a piece of meat and he was a
hungry animal. As I got to the bottom Bruce backed away a little to
make room for me. After I got off the last step I spun around and said
to Bruce "What do you think?"
He didn't say a word as he took me in his arms and kissed me deeply.
His hands were roaming over my butt and my bare back, focusing mainly
on my butt. A massive erection began in his slacks. I wanted to drop
to my knees right there. I dropped one hand from his shoulder and
caressed his hard-on through his pants. Bruce broke the kiss. "You
are so hot! Let's take it easy because I don't want to spoil your hair
or your dress before dinner. After dinner though is another story
entirely!"
I giggled. "Then let's eat fast," I said.
Bruce grinned and wrapped his arm around me, his hand caressing my butt
as we walked. I was so turned on I didn't think I could wait until
after dinner.
Bruce had set up the table for a candlelight dinner. He led me to my
chair and actually held it out for me. There was a glass of wine in
front of my plate. I guess he was going all the way in contributing to
the delinquency of a minor! However, I did sneak a drink every now and
again at home when my parents weren't around.
Dinner was beautiful. Bruce was an okay cook but I must admit that he
wasn't nearly as good as I was. Being a latchkey kid I had been making
my meals for quite some time. We chatted throughout dinner. Bruce
spent most of his time leering at me with a devilish grin.
When we were done with dinner I said that I would clear the table.
Bruce would have none of it. "I'll clean up later on. Right now I
want to eat you up for dessert!" He practically bounded over ripping
off all of his clothes, pulled my chair out, lifted me out of my seat
and took off my dress. I covered myself. I was very self-conscious
standing there in only a thong and high heels. Bruce moved my hands to
my side. "Please don't. You look absolutely stunning." I grinned and
wrapped my arms around his neck. We made out furiously. Once again
Bruce moved his hands to the object of his desire. He again took a
finger and massaged my asshole. This was really turning me on. I was
surprised when Bruce dropped to his knees and began kissing my cock.
Being new to this and feeling uncomfortable with him doing this to me I
gently pulled his head away from my crotch. "Please don't. I can cum
just by doing that to you." I don't think that bothered Bruce. By the
way that he acted I think that he might have actually been relieved.
He was definitely the top in this relationship.
What he did next absolutely blew me away. He gently turned me around,
facing the table. His face was pointed to my ass and he grabbed hold
of my hands and placed them on the table. Next he used his hands to
ply apart my butt cheeks, one hand moving the thong as well. Then he
started to lick my asshole! Far from being grossed out I was so turned
on I came right away, shivering uncontrollably.
"Wow, that was incredible," I exclaimed after I came to my senses. "I
can't believe you did that."
"Well, every good man eats out his woman. It's only fair you know."
"Believe me, I don't mind," I said. Then it occurred to me that he had
just referred to me as his woman! I definitely didn't mind that!
Bruce turned me around and we made out like two animals. I didn't even
think to not consider kissing him because of where his tongue had been.
After a minute of kissing I dropped to my knees and got his hard cock
into my mouth as quickly as possible. The head was slimy with pre-cum
which I licked off immediately. I didn't mess around. I wanted his
cum so badly I went to town. I didn't even realize that I was taking
at least 2 more inches of his cock in my mouth than I had the first
time. After only about 2 minutes of sucking he yelled that he was
going to cum. His first spasm was so violent that I couldn't keep his
cock in my mouth. It popped out and the first huge jet splattered
across my face. I got him back into my mouth in time to take the
remaining spurts. I swallowed as quickly as I could but some drooled
out of my mouth and down my chin. The taste was incredible. The
feeling of his cum running down my face turned me on so much I came
again.
Bruce collapsed back onto the table and I collapsed on the floor. Both
of us were breathing hard. I never thought that sex could be so
intense. After a bit Bruce picked me up off the floor; cradling me in
his arms like a baby. He carried me into the living room. I could
feel his cock bouncing up and hitting me in the back as he walked. I
couldn't believe that he was still hard. He sat on the couch with me
still cradled in his arms. We looked at each other and it was the
first time that Bruce noticed that he had cum on my face.
"Oh my God pumpkin, I didn't mean to cum on your face. I'm so sorry."
"About what?" I inquired. "I think it's kind of neat. You can do it
again if you want."
Bruce looked at me in wonder. "My God Jennifer, you are every man's
dream girl."
Well this just put me even higher on cloud nine! I felt some of
Bruce's cum leak down to my upper lip and I stuck out my tongue to lap
it up. I felt another on my cheek and took my finger and wiped it up.
I put my finger close to my mouth and licked the cum off. All the
while I was staring at Bruce. He still had that look of erotic awe and
I knew I'd be on my knees shortly to suck him off again. I knew I was
still covered in cum but wasn't sure where the largest globs were so I
took Bruce's finger, wiped it across my face to get any cum and then
licked it from his finger. This was all the hint he needed and he
began to use his finger to wipe my face clean. He would feed his cum
to me in different ways. Sometimes he'd stick his finger directly in
my mouth, other times he would wipe the cum on my lips so I could lick
it off. Once he was moving very slowly so instead of waiting for him I
lunged up and sucked his finger into my mouth. "After a while of
intently searching my face for more he proclaimed "all gone!"
I nuzzled into him gently kissing his tight stomach. His cock was
beginning to spasm so I moved my head a little and began to lick it.
Before long I was on my knees again gently nursing on his cock. This
time it took him much longer to cum. I was able to keep his cock in my
mouth when he came and the volume was less although still decent. I
kept the cum in my mouth and savored the taste before looking up at him
as I swallowed it. He seemed to enjoy seeing my throat move showing
him that his cum was traveling from his cock to my mouth and ultimately
to my stomach.
I crawled into his lap again and we snuggled for a while. I heard the
clock chime 10 so I told him that I had better get cleaned up and head
home.
"Okay pumpkin," he said. "Do you want me to drive you home baby?"
"Thanks Daddy, but it's not far and I can ride my bike. Sometimes it's
fun to ride at night," I said. I was thinking that I needed a bit of
time by myself to sort out my feelings. I was falling madly in love
but despite what my mom had said I was still concerned about her
reaction.
We kissed deeply one more time before I got up and moved to the kitchen
to grab my dress before showering and heading home.
Meet The Parents
I got home just before 11. The light in the living room was on and I
thought that mom had left it on for me and gone to bed. Instead I
walked in to see her lying on the couch reading a book.
"I didn't hear a car; did you ride your bike home?" She asked sounding
concerned.
I told her that Bruce had offered but I turned him down.
"Have a seat," she said while sitting up and patting the couch next to
her. I was hoping that this wouldn't happen tonight. I still wasn't
prepared to talk about it.
"So, how was your day?" she inquired.
"I had fun. We went out to brunch, watched a movie, played some pool
and had dinner."
"Did you dress up?" she questioned.
I think that my eyes just about popped out of my head. Should I tell
her the truth? She was looking at me with an impartial stare. It
seemed to take an hour but was probably only a few seconds before I
told her that I had dressed up.
"Did you have sex?" she asked matter-of-factly.
"Mom!" I exclaimed. I was shocked by her direct question.
"Listen," she said rather sternly. "It is my right as your mother to
know what you're up to. I won't be at all mad if you did. Seeing that
twinkle in your eyes when you came in I'm pretty sure that you did." I
didn't answer. Finally she said, "If you don't tell me I am going to
tell your father that you dress up as a girl when you're with Bruce."
This was downright blackmail! The last thing that I wanted my father
to know was that I was dressing up. "Yes," I said while looking down
at my hands.
Mom gave me a big hug. This surprised me. "How was it? She inquired.
This I couldn't lie about. "Spectacular!"
"Well I'm glad," she said. "You'll have to give me all of the juicy
details later because it's getting late." She gave me one last big hug
before going off to bed.
I can't tell you how I felt. A little relieved, a little scared. I
made my way up to bed. It seemed to take forever to fall asleep. I
had so much on my mind.
I woke to a knock on my door. I looked at the clock and it was almost
9.
My mom entered the room carrying something behind her back. She turned
on the light and I was temporarily blinded. "I have to tell you that I
lied last night. I already told your father about how you like to
dress up. Anyway, he was absolutely fine with it. So, I went out and
got you something to wear today. I figured I'd have you wear it since
you and Bruce are now an item. Oh, and I already told your father
about that. He's very happy for you. Anyway, I've always wanted to
have a girl that I could buy clothes for! Your father loves it and
can't wait to see you in it."
I almost wet my bed. This was the most frightening thing that I could
imagine! My eyes were finally adjusting to the light. Mom looked the
happiest that I had ever seen her. She was holding out one of the
cutest little dresses I have ever seen. This was definitely for a girl
in her early teens. It was white with a pink flower pattern
throughout. It had spaghetti straps and was tight through the bodice
with a flared pleated skirt that probably came down to about mid-thigh.
The material was quite thin so you would be able to see the outline of
my legs through the skirt if the light was right.
"Thank you mom but I don't know if I can dress like this in front of
you and dad."
"You can and you will," she said sternly. I guess I was going to have
to wear it whether I wanted to or not. Believe me; I really wanted to
wear it but just not in front of mom and dad. "Now get up, eat some
breakfast and get in the shower; um what does Bruce call you?" She
asked.
"Jennifer," I said a little embarrassed.
"That's a beautiful name! If you had been a girl I would have named
you Elizabeth. So, how about we go with Jennifer Elizabeth?"
"Okay," I said quietly.
"Fine then, get something to eat and get into the shower immediately
Jennifer Elizabeth. I want to have plenty of time to get you ready for
your boyfriend."
I blushed and got out of bed as mom left the room. I threw on some
sweats and went downstairs to eat after spending a few minutes studying
myself in the mirror. I came to the conclusion that I was much more
attractive as a girl. I got a little scared when I saw dad standing in
the kitchen. He looked up and gave me a smile. He walked over without
saying a word and gave me a big hug! Wow, he had never hugged me
before, at least as far as I remembered. "Your mother told me and I am
truly happy for you. If this is what makes you happy then I will
support you as much as I can."
"Thank you dad; I was so worried that you would be mad at me," I said
into his chest.
"I'm not mad at you at all. I always suspected something was different
about you. You're not hurting anyone by being this way so how could I
be mad at you."
I thanked him again and we broke our hug.
"From now on," he said, "you will be treated like my little girl and
that means that I had better approve of your boyfriend."
I blushed. "Don't worry dad, he's a great guy." He smiled at me and
left the room.
Okay, now I was happy. I knew that mom and dad were genuinely pleased.
I hoped that Bruce wouldn't be mad that I had shared everything with
them. I quickly ate my breakfast and ran upstairs to shower as mom had
asked.
Mom was in my room when I had finished. She handed me my dress and a
white silk thong. My God I didn't think mom even knew about thongs.
She must have seen my look because she immediately said, "This dress
will show panty lines so you need to wear a thong. Most girls wear
them all of the time now even if they don't need them. Now get your
panties and dress on and join me in my sitting room. I'm going to work
on your hair and makeup."
She left and I got dressed. The dress felt and looked wonderful. It
was so light and airy! It was definitely for a girl with little to no
breasts so it fit quite well. I spun around in a circle and saw that
the dress flew up really high. You could actually see above the top of
the thong. The feeling was indescribable.
I bounded to mom's sitting room. She had a bunch of makeup laid out on
the table. She told me that I looked very cute and she had me sit down
and walked me through all of the makeup. I told her what I had learned
from the computer program that Bruce had given me. She gave me a lot
of additional tips that really helped. She let me put on my own
makeup; helping me all the while. It took a bit more time than usual
but in the end I must say that I looked great. I was a very sweet
looking young teenaged girl. Then she opened a drawer and pulled out a
bunch of clip-on hair extensions. This was great! I would finally
have long hair! She showed me how to put them in and after quite a bit
of work I had beautiful long wavy hair well past my shoulders! She
showed me several different styles and we finally decided on a high
ponytail held in place by a really cute white bow clip. A little
tendril of hair fell on each side of my head. Next she pierced both of
my ears twice. It hurt like hell but I was happy with the results.
She put a small hoop in each ear followed by a really cute dangling
earring in the other hole in each ear. She also gave me a cute charm
bracelet and a simple gold chain necklace. We went with a couple of
rings on each hand and a toe ring on each foot. Finally came another
charm bracelet for my ankle. She polished all of my nails with a pink
nail polish that matched the flower pattern in the dress.
This was when we had our most intimate conversation ever. She asked me
what sex was like with Bruce. I opened up and although I didn't get
too graphic I told her about the blowjobs and the fact that he was so
huge I didn't think we could ever truly make love. She told me not to
worry and that my asshole was much more pliable than I thought. Based
on her knowledge she obviously had anal sex before.
After my nails had dried she handed me a pair of cute white sandals. I
put them on and she had me stand in front of the mirror. I was
flabbergasted. I couldn't believe how good I looked. You could tell
it was me; I just looked so much cuter than I had thought possible.
Mom was also impressed and poked her head out the door and called my
dad. I got nervous waiting for him to come up. Mom heard him coming
and partially opened the door.
"Mitch; I would like to introduce you to your new daughter, Jennifer
Elizabeth." With that she opened the door completely. Dad looked me
up and down and gave me a big smile. "My God, you're beautiful!" I
blushed and he came over and gave me a hug.
Just then the doorbell rang and I saw that it was noon. I looked out
the window and saw Bruce's car in the drive. I just looked around
wide-eyed.
"Aren't you going to get the door?" Mom laughed.
I ran downstairs without a word and nervously opened the door. I was
sure mom and dad were listening at the top of the stairs. Bruce was
standing there looking as handsome as ever. "Hi," he said. "I'm
Bruce. I didn't know that Jim had a sister."
I smiled. "It's me, Jennifer, silly." His eyes got huge.
"Oh my God you look absolutely adorable!" He came to give me a hug and
stopped. "Your parents know?" he asked a little nervously.
"Yeah, my mom got it out of me last night. Absolutely everything. I
wanted to call you and warn you in case you didn't want to come.
They're very happy about it," I said quickly. I was so worried he
would get mad and leave. Instead he said, "Wow, that's great!" And he
gave me a kiss right there on the front porch.
All of a sudden right behind me I heard mom say "You must be Jennifer's
boyfriend."
I turned around quickly, "Mom, don't embarrass me!"
I heard Bruce laugh and say, "Guilty as charged."
This made me laugh. Dad was right behind mom and I introduced Bruce to
both of them. It went great! Bruce held my hand as we made our way
out back. Bruce and my father hit it off right away. Dad got Bruce
and himself a beer and they began to talk about sports. Mom pulled me
away and into the kitchen.
"Wow, he's hot!" Mom exclaimed. All I could do was giggle. Mom then
said, "My God girl, don't let him get away. You don't know how lucky
you are! Good looking, good in bed, so far, a huge cock and lots of
money."
"Mom, don't talk about the size of my boyfriend's cock," I said
embarrassed. "But yes I do know how lucky I am."
She laughed and we made our way outside with some food. Bruce gave me
a hug and we all stood there walking. Bruce spent most of the day
either holding my hand or with his arm across my shoulders. This show
of affection meant a lot to me. He even gave me a kiss right in front
of my parents!
The barbeque was over much quicker than I thought that it would be.
The day was a great success. I was surprised when mom decided to take
dad to the airport. Then she reminded me that she was scheduled to fly
out to meet him on Friday and they were going to Europe for two weeks!
So much had happened recently that I had forgotten all about their
trip. Two weeks alone with Bruce! I hoped he would ask me to stay
with him the entire time.
Dad pulled me aside before he left. "Jennifer, I want to tell you that
I think that Bruce is a great guy. From the way he talks about you he
cares for you a great deal. So, whether it matters or not, you have my
blessing."
I gave him a big hug. "Thank you dad; all of this means so much to me.
I'm so happy that you're okay with this." With that he went to get
ready to leave.
Mom and dad said their goodbyes. Mom wouldn't be back for at least 3
hours so I had plenty of time to fool around with Bruce. He obviously
felt the same way because as soon as the door closed he gave me a deep
kiss and his hands once again found my butt cheeks. "Oh pumpkin, it
was all I could do to keep my hands off you today. You look absolutely
adorable!"
"Really," I said. I pulled a little bit away and said, "What do you
think?" Then I spun around so my skirt flew up and he could see my
thong. He didn't need to answer because a bulge instantly appeared in
his pants.
"Come here you sexy little thing!" He yelled. I wrapped my arms around
his neck and he ran his hands up my legs and under my dress. He picked
me up and I wrapped my legs around his back. We kissed while his
finger found and massaged my asshole. "Where can we go?" he asked as
we broke our kiss.
"There's a spare bedroom upstairs," I said breathlessly. He carried me
upstairs just as we were. I pointed him to the door and he opened it
and practically threw me on the bed. He leered down at me as I lay
there with my legs spread wide. He stared at me as he took off his
clothes. This man meant business and I knew it. I jumped up. "Hold
on," I said as I bolted out of the room. I ran to my mom's dressing
table and took out some of the clear lotion that I had used on the
rough spots on my elbows. It was pretty greasy and I thought that if I
used enough he could at least get a finger inside of me.
When I returned Bruce had thrown the covers from the bed and was
standing facing the door with his hard cock pointing straight at me. I
jumped into his arms and again wrapped my legs around his back. As if
on autopilot his finger again found my asshole as we kissed. I broke
the kiss and showed him the bottle in my hand. "Maybe you can find a
use for this," I said coyly.
He got a huge grin on his face and turned around and laid me face up on
the bed. He got down on his knees and lifted my legs. He put his face
in my ass and began to lick. It was incredible! He was alternately
frantic and gentle. I squealed and came all over without even touching
myself.
Bruce grabbed the lotion and generously coated his fingers and the
outside of my rosebud. Ever so gently he swirled his index finger
around my asshole and slowly entered into me. I began to moan in
ecstasy. Once he got in to his first knuckle he pulled out again. He
pushed back in and slowly worked his way up to his second knuckle. He
began to massage my sphincter which felt so incredible I immediately
got as hard as a rock. Sure it hurt a little but he was very gentle.
The thought that he would eventually be placing his dick in the same
spot added to the pleasure. If he wasn't so huge I would have taken
him in right at that moment but I had a long way to go before I could
accommodate him.
Eventually he buried his finger to the hilt and began to finger fuck
me. He moved up to me and I gave him a big smile. "How does it feel
pumpkin?" he asked.
"Absolutely wonderful," I purred.
We made out as he continued to finger fuck me. I came again after
about 5 minutes. I noticed that I had begun to groan and squeal louder
and louder every time I came. By the look on his face Bruce really
seemed to enjoy this. This squeal was particularly loud. After I
opened my eyes I noticed Bruce kind of laughing. I was embarrassed.
"I'm sorry daddy, I don't know what came over me."
"Be as loud as you like sweetie. It lets me know when I hit just the
right spot," he said with a smile. He continued to finger fuck me very
gently. Eventually he pulled out all of the way. I felt a little
empty but judging by how his dick was throbbing it was obvious that he
needed some relief. Since I would have to wash the bed sheets anyway I
used the sheet to clean off his hand.
I grabbed at his ass and pulled him forward. I knew that it wouldn't
take long so I figured that I would lay there while he fucked my mouth.
He got the hint and moved up to my face. I looked up at him as I began
to lick the underside of his cock. He looked down at me with such lust
I knew what I wanted to do. After about 2 minutes of licks, kisses and
gentle sucks he announced that he was ready to cum. I pulled him out
of my mouth and lifted my head a little just as he shot his first
spurt. It landed square on my forehead. All of the rest of the spurts
did the same. My face was absolutely soaked.
When he finally finished I opened my mouth and through a veil of cum
said, "How do I look?"
"Fucking spectacular; I wish that I had a camera."
I laughed. "Please run to the bathroom and get a mirror."
He got up and was back in a few seconds. There was cum on my eyelids
so I was afraid to open my eyes. Bruce saw this and used his finger to
gently clean it away. As he was doing this I said, "I want it, please
feed it to me." Of course he didn't hesitate to do this. He loved the
fact that I wanted to eat all of his cum. Eventually I was able to
open my eyes and was amazed at how I looked. Here was a cute 12 year
old "girl," absolutely covered in cum. It was indeed a spectacular
sight.
Bruce had me lay back on the bed and gave me the mirror. I held it so
I could see my face as he used his fingers to scoop up the cum and feed
it to me. When my face was clean we snuggled for a while.
"My mom and dad really liked you," I said.
"Thank God," he said. "I would have been devastated if they didn't.
Now we can be in the open about our relationship."
Relationship! What a wonderful word. I was now sure that he felt the
same about me as I did about him. This wasn't strictly to get in my
panties but to care for one another deeply. I was sure that I was in
love with him but didn't want to say anything for fear of scaring him
off.
"When did you become attracted to me?" I asked.
"Well," he said, "when I first saw you I thought that you were cute but
for some strange reason I thought that you would be even better looking
as a girl. I was pretty darn happy when you had to wear my ex-wife's
clothes. Once I came in and saw you in one of her suits I knew right
there that I wanted to get in your panties." We both laughed at that
comment.
We snuggled for quite a while. Eventually my face began to crust over
from the cum that he was unable to scoop up. I knew that I probably
looked terrible. I looked over and saw that I only had about an hour
and a half before mom got home. "I'm sorry sweetheart but I'd better
get this cleaned up before mom gets home."
"Yeah, I'd better be going too. I have some work to do around the
house," he said.
"Well don't do the laundry or the dishes. That's part of my job now
remember?" I reminded him.
"Oh pumpkin, don't even think that I would expect you to do housework,"
he said seriously.
"But I want to. It would be fun. Please let me do it?" I pleaded.
He looked at me to see if I was serious. "Okay, but don't feel like
you have to do it." After a pause he said, "You know Jennifer if
you're okay with it I would prefer to only see you dressed as a girl
from now on."
"Well that's good because I only want to see you while I'm dressed as a
girl," I said. Bruce gave me a kiss and got up to put on his clothes.
He looked down at me as he dressed. I was sprawled on the bed with my
dress hiked up far enough so he could see the material of my thong.
"Pumpkin, you are so fucking hot," he said.
I just smiled and then I recalled that my parents would be gone for two
weeks starting Friday. "Bruce, my mom and dad will be in Europe for
two weeks beginning Friday. I hope we can spend a little more time
together?" I inquired hopefully.
"That's great!" he exclaimed. "You can stay at my place the entire
time if you'd like." He bent down to kiss me. "I would love to wake
up next to you in the morning." I almost swooned as we kissed.
We were running late so I walked him to the door. We kissed each other
goodbye and he left. I quickly ran upstairs to get the sheets in the
laundry and take a shower. When I was done I threw on shorts and a t-
shirt and was just putting the laundry into the dryer when my mom
walked in. "So, you and Bruce dirtied up the sheets in the spare
bedroom I see," she said with a grin on her face. I just smiled and
didn't say anything.
I followed mom into the kitchen and she stopped and turned to me. "He
really is a great catch," she said. "It's pretty obvious that he's in
love with you as well. Consider yourself lucky." I told her that I
did.
"Now," she said, "I think that we should go shopping for some clothes
for you."
"Don't worry about that mom. His ex-wife left a huge closet full of
clothes that fit me perfectly. I could wear one outfit a day and
probably not wear the same thing twice. She even left all of her
jewelry and some makeup," I explained.
"Well the makeup is probably getting old so let's go to the mall and
I'll pick some up. We don't have much time so why don't you get
dragged along by me as a boy rather than be excited to be buying makeup
for you as a girl?" I told her that I could live with that.
Although I was dressed as a boy we talked like mother and daughter. It
was the closest that I had ever felt with her and I think that she felt
the same way. She bought a ton of makeup, hair products and perfume.
She said that she would drive me to Bruce's on Monday so I could leave
it at his place.
When we got home mom had me wait in the living room while she went to
get something. She came back with a box that she set on the couch
between us. She had me open it and inside was some lubricant and 2
dildos; one bigger than the other but neither close to Bruce's size. I
must have turned ten shades of red.
"How does Bruce compare?" she asked matter-of-factly. Still very
embarrassed all I could do was point to the larger one and say "about
twice as big."
Her eyes got big. "You're joking right?"
"No," I replied meekly.
"Well, if he knows how to use it consider yourself one lucky girl!" She
exclaimed. "How much does he cum?" She inquired curiously. I couldn't
believe that she was asking me this but I didn't want to make her mad
by being embarrassed. After all maybe mothers and daughters really
talked this way.
I pushed away my embarrassment. "It depends. I think there may have
been about half a cup's worth the first time." I don't think that she
believed me although I was telling the truth.
"Measure it sometime and then tell me," she said. "And how does it
taste?" She asked.
Again I was embarrassed but answered anyway. "Great. It wasn't what I
expected but it's really good. I can't seem to get enough of the
stuff." This last part just came out unexpectedly and I once again
turned red.
Mom laughed. "Well, that's important. It isn't nearly as enjoyable if
you don't care for the taste. Now let's get down to business. I'm
giving this to you because I imagine that at some point you and Bruce
are going to fuck. You will need to build up to his size as much as
possible. If he's a big as you say that he is, and if so I'm very
jealous, there's no way he'll be able to enter you without tearing you
apart. However, if you do it right you should be able to take him once
you can take on this big one comfortably. It's an amazing feeling so
you'll want to experience it in a positive way the first time."
Well, it was out. My mom had been fucked in the ass and she is a
swallower. Oh well, she knew that I was as well. I thanked her and
she patted my knee and told me to have fun.
Before she left she turned to me. "I imagine that you and Bruce will
probably be shacking up together while your father and I are away?" I
shook my head yes. "That's fine. If you find that you're running late
and want to stay the night at all this week just give me a call to let
me know you're okay. Don't stay there every night though because I
need your help getting things together for the trip. If you're here
Wednesday and Thursday night that would be fine with me."
This was great! I was feeling that I might be able to spend most of
the summer at Bruce's place! I thanked her and we hugged.
Two Weeks of Bliss
I had a hard time getting to sleep that night and was up at the crack
of dawn and ready to go to Bruce's. I kept pestering mom to get ready
because I needed time to get dressed at Bruce's. She calmed me down by
saying that she would do my makeup for me. She gave me a rather sexy
secretary look. "There, you now look like a secretary that any boss
would want to bang," she said with a laugh. I had to admit that I
looked pretty hot.
When we got to Bruce's I ran upstairs to change. He had picked out my
outfit for the day and left a note. "Hey babe, I can't wait to see you
in this. How about you do your real job for half days in the morning
and then work around the house in the afternoon if you'd like. This
way you can wear at least two different outfits each day. Love,
Bruce."
I was surprised by what he had chosen. It was a white pantsuit with a
basic pink tank top. It was definitely feminine; I mean the jacket
tied with a bow, but it was kind of plain. I got dressed, put on some
jewelry and heels and made my way to the office.
"Good morning," I said as I walked into the office. I was a little
concerned. Was yesterday just a flash before the light burned out?
"Good morning Miss Smith," Bruce said before looking up. He had a grin
on his face which turned to a look of lust. "Damn it! How am I
supposed to get anything done with you looking like that?"
I was taken aback. Was he really mad?
He stood up. "I chose that suit because it was pretty plain. I
thought that if I didn't let you dress sexy we could work instead of
fool around like two horny kids."
"I'm sorry," I said rather meekly.
He laughed. "Okay, tomorrow we'll find something frumpy for you to
wear."
I brightened up. "I have a better idea. How about if I come in a few
minutes early each day and give you a good morning blowjob? Then you
should be able to focus on work until at least lunch time."
"That sounds like a great plan! Now let's get started," he said as he
removed his belt.
I walked over to him, got on my knees and waited for him to unveil his
hard cock. I sucked him for about 10 minutes or so. I was just
enjoying the situation and didn't want to rush. Eventually he
announced that he was ready to cum so I jacked him off in my mouth. He
filled my mouth but instead of swallow I held it all in. When he
opened his eyes I stood up and looked up at him. He looked down with a
lusty grin on face. I opened my mouth to show him all of his cum,
closed it and swallowed a couple of times to get it all down and then
opened it again to show him it was all gone. He gave me a kiss on the
lips. "Good morning babe. That was spectacular. Now let's get to
work."
I turned back to my desk and he gave me a swat on the butt. "Don't you
know that's sexual harassment?" I said with a laugh as I looked back
over my shoulder. He laughed and walked back to his desk.
I was surprised that we were able to work. This had actually concerned
me because if we couldn't work while we were in this relationship I was
worried that I would lose either one or the other. I actually became
much more secretarial. I would bring him coffee; things like that.
It was almost Noon when Bruce mentioned getting lunch. I decided that
it was my duty to get him lunch as either his secretary or his
girlfriend. "That's an expensive suit so how about getting lunch as my
girlfriend; or perhaps daughter?" he said.
"Okay, I'll be back shortly," I said. So, if it's his daughter he
wants than it's his daughter he gets I thought.
When I got to my room I saw a note from Bruce on the bed. "Hey
Pumpkin, look in the smaller closet, you may find some other clothes
that you'd like to wear. Love, Daddy." Bruce must have placed this on
the bed while I was working.
I ran to the smaller closet; although smaller still meant larger than
any other closet I had seen prior to the big closet in this room. I
turned on the light and saw that it was about ¼ full of clothes. They
all had tags on them and all were for a young girl; perhaps between 10
and 16. There were assorted shoes, hair accessories and jewelry all
for the same age range. The clothes were so cute! Obviously he wanted
his daughter rather than a girlfriend. I pawed through the clothes and
found an adorable miniskirt. The top half was blue jean followed by a
white layer with a flower pattern followed by a lace layer. Since it
was for someone much younger it ended up barely covering my butt
cheeks. The top was a white short sleeved crinkled top. I took off my
sexy secretary makeup and put on just a touch of eye shadow and lip
gloss. I held my hair back with two butterfly hairclips. I didn't
wear a bra at all since I wanted to look as young as possible. I did;
however, put on a thong. I didn't think many young girls wore thongs
but I wanted Bruce to have easy access if he wanted it; which I was
sure that he would.
I checked myself out in the mirror and saw an adorable 10 year old
looking back at me. I was excited to see what he would think. I
bounded downstairs and into the kitchen to fix lunch. When I was done
I set it on the table and went to the office to get Bruce.
I skipped into the office saying, "Daddy, lunch is ready."
"Okay Pumpkin," he said before looking up. When he did look up he got
a rather dirty look on his face. "I should go to prison for thinking
this but you look very sexy."
"Daddy," I said in as innocent a voice as I could. "Does this mean you
like my outfit?" I asked before I spun on my toes. Of course my skirt
flared up just like I thought it would and I knew he could see
everything.
He stood up and walked over to me. "Yes, I like your outfit a lot.
Now give your daddy a hug."
I did as he asked. I placed my arms around his neck and he lifted me
up with his hand on the outside of my skirt. I felt his raging hard-on
against my body and decided to play it up. "Daddy, what's that hard
thing in your pants?"
Bruce laughed. "Why pumpkin that's daddy's cock. It got hard because
you look so pretty."
"Wow," I said, "can I see it?"
"You sure can," he said. "Get down on your knees in front of daddy
like a good little girl." I did as he asked and he proceeded to take
down his pants.
I looked at it. "Neat," I said, "can I touch it?"
"Sure sweetheart. What you're supposed to do is grab it in our hands
and run them up and down it, but not too hard, okay?"
"Okay daddy." I did as he instructed and before long he said that he
was going to cum soon. "What's that daddy?" I asked innocently.
"It's white stuff that comes out of the end of daddy's cock. Would you
like to see it?"
"Sure, that would be cool!" I exclaimed.
"Okay, here's what I want you to do. When I say so I want you to stop
stroking it and cup your hands in front of it. I'll finish stroking it
and it will shoot the white stuff into your hands. You can even taste
it if you want."
"Okay, that sounds like fun!" I said excitedly. I continued to stroke
for about a minute when he said that he was ready. I did as I was told
and the first spurt almost filled up my cupped hands. The second,
third and fourth overflowed onto my arms and bare legs. When he was
done I said, "Wow that was cool daddy. Are you sure I can taste it?"
When his breathing slowed enough for him to talk Bruce said, "Sure
baby, try some of daddy's cum. I think that you'll like the taste."
He watched me intently as I brought my hands to my face. Some cum
sloshed over the side and left a string all the way down to my legs. I
sucked up a little making a loud slurping noise, swirled it around in
my mouth and swallowed it while looking at Bruce. He had a lecherous
look on his face. "Yummy," I said. "Can I have some more?"
"Yes pumpkin, you wouldn't want to waste any."
With that I proceeded to finish it off. I tried to pour some into my
mouth but that didn't work too well and most of it poured down my chin
and into my lap. "Ops," I giggled. Bruce laughed when I did that. He
continued to leer at me in wonder as I lapped up the rest in my hands
and on my arms and sucked my fingers clean. "That was yummy daddy, can
I have some more?" I asked enthusiastically.
"You can have all you want pumpkin but I need a bit of time to
recover," he said as he laughed.
He picked me up by the arms and gave me a long deep kiss. "Oh
Jennifer, I wish you could stay here. The house is so quite without
you and it's all I can do to keep from jacking off while you're gone."
"Well," I said brightly, "Mom said that I could stay the night tonight
and tomorrow night if I wanted to but I'd have to be home Wednesday and
Thursday, but then I can stay for two whole weeks if you want!"
"Seriously?" He inquired. I shook my head yes and he gave me a big
hug. "Your parents are the best babe. Most would hate the idea of the
two of us even seeing one another and far fewer allowing you to spend
the night with me."
"Oh, my parents really like you; mom especially." I said happily.
Bruce picked me up by my butt. His hands were under my skirt gently
squeezing my cheeks and his finger once again began to probe my
asshole. We made out for a while before Bruce pulled his face away
from mine. The cum on my face was beginning to harden and I was about
to excuse myself and go take a shower when Bruce said, "Did you cum
princess?"
I shook my head yes. "I always cum when I taste your cum daddy."
Bruce smiled at me. "Good, because I want to make sure you enjoy
yourself too. Now, I want to save myself for tonight but there's one
last thing I want to do." With that he set me down and turned me
around to face the desk. He gently pushed on my shoulder as if asking
me to lay myself prone on the desk. I did so and he got on his knees
behind me, lifted my skirt and moved aside my thong. He pulled apart
my butt cheeks and next I felt the warm wetness of his tongue on my
asshole. The sensation was spectacular to say the least. He must have
tongued me for five minutes before he replaced his tongue with his
finger. He very gently entered me. He was able to enter very easily
with no pain at all because I was so relaxed. He kissed my cheeks as
he slowly fucked me with his finger. I was moaning very loudly and
after only a minute or two I came once again. I squealed very loudly
as I came. If Bruce had any neighbors they probably would have heard.
Once my orgasm subsided Bruce pulled his finger out, rolled me over and
we kissed deeply. I was feeling very crusty from the dried cum so I
excused myself to clean up. I reminded Bruce that lunch was ready and
I made him promise that he would leave his dishes on the table for me
to clean up.
I decided to wear something casual for the rest of the afternoon since
I'd be cleaning and doing laundry. I put my hair up into a ponytail
high on the back of my head. The extensions were working great but I
couldn't wait until I didn't need them anymore. I chose to wear a pair
of denim capri pants and a tight midriff baring tank top with a padded
bra. I kept the makeup and jewelry to a minimum.
When I went downstairs Bruce was at his desk. I walked over and gave
him a kiss on the lips. I turned to go and he swatted me on the butt.
"Nice ass," he said. I smiled and sashayed out of the office. I spent
the rest of the afternoon cleaning and doing the laundry.
I really hadn't spent any time in Bruce's room but now was my chance.
I was pleasantly surprised to find that he had framed a couple of the
pictures that he had taken of me! This was perhaps the most unkempt
room in the house. The bed wasn't made and his dirty clothes were
strewn about the floor. I decided to clean the sheets for our first
night together. I hoped that I would need to clean the sheets every
day after I spent the night. I found some silk sheets in the closet
and decided to put these on. I had never slept on silk sheets before
and they felt so erotic that I couldn't resist.
At about four I went in to see what Bruce wanted for dinner. "Hey
daddy, what would you like for dinner?" I asked. He moved his chair
out from his desk and patted his leg for me to sit down. I walked over
and straddled his legs, facing him. "A piece of sexy underage ass
sounds good," he said half jokingly. I laughed. "Maybe after dinner."
We decided to order Chinese in since he had a client coming over early
in the morning and it wouldn't be a good idea to be out late.
"How should I dress for work tomorrow?" I asked.
"I would go with a casual suit. He's a decent size client and I want
to impress him."
"Okay, but I need to go out and get one. I don't have one at home." I
stated.
He looked at me a little surprised. "You have a huge closet full of
clothes up there. I'm sure you can find something to wear."
"You mean you want me to dress like a girl, even in front of a client?"
"Sure babe. As far as I'm concerned you are a girl, and a damn fine
looking one at that. Like I said before, I only want to see you as a
girl from now on."
I kissed him. "Thank you. I feel the same way. I'm just worried
about being able to pass myself off as a girl."
"You look as much like a girl as any girl I've ever known. Now let's
order dinner, I'm starving."
We ordered dinner and when it came Bruce had me go to the door and pay
for it. I was happy when the delivery boy leered at me the entire
time. Nobody other than Bruce had ever undressed me with their eyes.
It was an uncomfortable, yet erotic feeling. Bruce was watching,
hidden from view, and gave me a hard time for the rest of the evening.
We ate dinner, chatting away like a young couple in love. I cleaned up
when we were done. I chided Bruce when he tried to help so he spent
the entire time sitting at the table staring at me. I would turn
around and give him a smile every once in a while. As I was finishing
up Bruce came up behind me and started kissing the back of my neck and
rubbing his hands all over the front of me. I could feel his hard on
pressed against my back.
"Do you want me to relieve you now daddy or should we wait until
bedtime?"
"What would you like to do pumpkin?" he asked.
"Well, as much as I want to blow you now I wouldn't mind waiting.
Remember, the longer I tease you the more you cum and I want as much of
that as possible," I said with a sexy grin.
"Okay, but get ready for a huge load because I've been hard all day
just thinking about you."
"That's fine with me," I giggled.
We decided to watch some TV. Much of the time was spent making out.
Eventually we couldn't take it anymore and decided to go to bed. We
made our way upstairs. Bruce had his hand on my ass the entire time.
I loved that feeling. When we got upstairs I excused myself to get
ready but before I went I said, "Daddy, would you mind videotaping
this? I think it would be fun to record." He smiled. "I'll videotape
everything if you want."
I went to my room and got ready. I had already chosen to wear a cute
white baby doll. I put my hair up in pigtails with cute little bows
and of course I wore a white thong. I freshened up my makeup and went
to Bruce's room. He was laying in wait on the bed once again sporting
a huge hard on. The video camera was already on and he was holding the
dildo that I had put on the bed earlier along with some lubricant. It
was the smaller of the 2 that mom had given me but it was still larger
than his 2 fingers. I was a little nervous but also excited. Seeing
his huge cock standing proudly in the air made me wish that I could
jump right on it.
Bruce looked at me when I entered. "Oh baby, you look so fucking hot.
Turn around for me," he said this in almost a demanding tone. I was a
little worried about the way he sounded. Would he be gentle or was he
so far gone that he would be rough? I turned around like he asked.
"Come here pumpkin," he said in a more gentle tone.
I walked over and climbed on top of him. His hard cock ran up my back.
His hands immediately went to my ass as I came down to kiss him. He
kneaded my butt cheeks as we made out in a wet slobbery French kiss. I
started to push my way down so I could suck his cock but he stopped me
and said, "This time you go first." With that he flipped me on my back
and grabbed the dildo and lube. The feel of the silk sheets on my back
was very erotic.
He towered over me and for the first time with him I felt vulnerable
and a little scared. He noticed this and said, "Relax sweetie, I'll be
very gentle." With that he lowered himself, placed my legs over his
shoulders, moved his head down and proceeded to give my asshole a long
wet tongue lashing. After a few minutes he stopped and grabbed the
bottle of lube. He grabbed a towel and had me lift my hips so he could
slide it under me. Next he poured a generous amount on his fingers and
coated my asshole. He poured a little more on and inserted his finger.
Again I gasped as he entered me which caused him to smile. I was
getting close to cumming so he stopped and just watched me. "Please
don't stop," I whispered.
"I don't want you to cum yet baby," he said. It took all I could to
calm down but after a minute or so I was back down to a less intense
state of arousal. He proceeded to coat the dildo in lube and place on
my asshole. "Are you ready pumpkin?" he asked. I shook my head yes
and he very gently began to penetrate me. I wanted this so bad that he
easily penetrated me. Inching in and backing out ever so slowly I was
in the throes of passion. All the while Bruce was looking at me with a
smile of lust on his face. I knew that he wished that it was his
humongous cock inside of me. Soon Bruce was in me about five inches
and he began to gently fuck me with the dildo. I was moaning very
loudly until I let out a loud scream and came all over. Bruce
continued to fuck me as I slowly came down from my orgasmic high. I
was breathing heavily as he pulled the dildo all of the way out. This
was the only time that it really hurt.
Bruce used the towel to wipe my asshole clean as well as the dildo. He
used another towel to wipe his hands off. By the time he was done my
breath was back to normal and he had straddled my chest with his cock
pointing straight at my face. I pushed myself up and back a little so
that the pillows were comfortably propping up my head. Bruce moved
forward a little so his cock was resting on my lips. I looked up and
him and began to nurse his cock and run my hands up and down it. I
began moaning as I was doing this. Bruce continued to look at me with
lust. I felt like I was being eyed like a piece of meat by a man who
hasn't eaten in weeks.
After only a couple of minutes I could feel that he was close. I kept
at it and soon he let out a loud growl and the cum began to shoot out
of his beautiful cock. It nailed the back of my mouth and I swallowed
as fast as I could but it was just too much. It filled my mouth and
began to pour out around his cock and down my chin. He must have
spurted out over a cup of cum. As he pulled his cock out he was
looking down at me and breathing really hard. I left my mouth open so
that he could see that it was full of his wonderful cum. Then I
swallowed. It took a couple of swallows to get it all down but
eventually I did. I then proceeded to lick his cock and my hands
clean. When I was finished Bruce laid down next to me. "That was
absolutely incredible baby. I have never cum like that before in my
life," he said as he tenderly used his fingers to move some of my hair
that was stuck to my face with his seed. I smiled and he gave me a
loving kiss on the forehead and then the lips. I wanted so badly to
tell him that I loved him but I was afraid of what he would do. I
snuggled up to him meaning to go and clean up in a few minutes but I
fell asleep and didn't move until dawn.
Bruce was sound asleep and still cuddling me when I woke up. My face
and chest were crusted over with his cum. I gently slid out from under
his arm and took a shower. I put on some makeup and a white bra and
thong. The clothes that I washed the previous day were still lying on
the bed in my room. I saw one of his white dress shirts and decided to
put it on. I had to roll up the sleeves a couple of times before my
hands were able to peek out from underneath. The shirt tail came down
to my knees. I looked in the mirror and thought that I looked pretty
cute. I made my way to the bedroom to wake Bruce up. He was just
clearing the sleep from his eyes when I walked in. "Okay, you look way
too sexy dressed like that," he said with a grin. I ran over and
jumped on the bed. He pulled me on top of him and we kissed for a
minute or so, his hands fondling my ass through his shirt.
Of course his cock got hard once again. This man is insatiable I
thought to myself; and that was fine with me! I grabbed the remote
control for the video camera and turned it on before I pushed myself
down and proceeded to give him a long gentle blowjob. He kept a close
eye on me the entire time; gently moving my hair out of the way
whenever he couldn't see. I took my time because I wanted this to
last. I would hold it steady with my hands and gently lick it all
over. Sometimes studying it closely and giving it little kisses. His
cock was truly a masterpiece; perfect in every way. I must have been
going at it for 15 minutes before he began to show signs of being ready
to cum. Since I needed to clean the sheets anyway and he needed a
shower I decided to jack him off. I loved watching the cum shoot from
the tip of his awesome cock. He began to cum. There was a little
dribble followed by three large bursts followed by smaller ones until
my hand and his cock and chest were coated. I proceeded to lick him
clean. I wish I could describe the wonderful flavor but words wouldn't
do it justice. To think that I was worried that I wouldn't like the
taste! I came without touching myself as I licked clean his chest.
I moved up to his face. There was just a bit of stubble on it which
kind of scratched when I kissed him. "Good morning pumpkin," he said.
"Hi daddy," I replied. "Thank you, last night was absolutely
wonderful."
"I should be thanking you. I've never experienced anything like it
before in my life," he said. "Would you like me to take care of you
baby?"
I snuggled up to him. "Definitely later daddy, I already came while I
was licking up your cum." He giggled a little when I said this.
"Sure thing pumpkin," he said as he kissed my forehead.
After about a minute I lifted myself up and asked him what he wanted
for breakfast. We talked about the day ahead and he got up to shower
and I went downstairs to fix him breakfast. I brought him a cup of
coffee when I heard the shower turn off. It was really fun getting
into the old fashioned wife routine.
When Bruce came down to eat he told me that I was too much and picked
me up and gave me a kiss. I went upstairs to get ready for work. I
decided on a short sleeved white lace shirt with a conservative black
skirt that came to just over my knees. I wore thigh high stockings and
black heels. I decided to leave my hair down. Bruce was in the office
when I came down.
He looked me over. "You're lucky I'm spent or I would need another
blow job," he said with a grin.
"Well hopefully you'll regain your strength before tonight," I said.
We got right to work. Bruce said that he wanted to get as much done as
possible so that we could both take some time off while my parents were
gone. I was looking forward to that! Not that work was bad at all; it
would just be nice to completely relax together as a couple. There was
one simple thing about being a girl that I really enjoyed for some
strange, unexplainable reason. I went over to his desk to ask him
about a couple of indecipherable words he had written. When I would
bend over I would take the hair that had fallen down and move it over
my ear. This really made me feel pretty for some reason.
The client that came to the office was a little older than Bruce. He
kept staring at me and Bruce had to repeat several things because the
man wasn't paying attention to him. I tried very hard to not be a
tease but it didn't matter. After the client had left Bruce told me
that he had a feeling that he would be seeing a lot more of him in the
future.
I made us lunch and Bruce once again told me to take the afternoon off.
I tried to argue that I had plenty to do but he would have none of it.
So I went upstairs to change. It was a rainy, chilly day so I decided
to wear a pair of white jeans and a cute pink sweater. It was a
camisole and cardigan. Although I liked to show my legs off to Bruce I
also liked to wear jeans because they would crawl up between my butt
cheeks which made my butt look very inviting. I brought Bruce some
afternoon coffee and of course he loved my outfit. I spent the rest of
the afternoon cleaning the kitchen and doing laundry. Of course I
changed the sheets on the bed!
I made a simple dinner. Bruce wouldn't stop saying how wonderful
everything was. We snuggled on the couch and watched TV until about 9.
This time I changed into a pretty pink silk chemise. Once again the
video recorder was running and Bruce was sporting a huge hard-on when I
came in. The night was just like the previous one. However, this time
Bruce was very gentle and loving rather than a sex crazed maniac. Not
that I didn't like the maniac it's just that I preferred the gentle
lover. Bruce used the smaller dildo on me again. I was so happy that
it was as pain free and pleasurable as the previous night. I figured
that I would be ready for the larger one by the weekend. I worked my
magic on his cock again and this time I was able to keep the entire
load in my mouth. Afterwards we snuggled together and I feel asleep
wrapped in his big strong arms.
On Wednesday I went with a pair of white slacks and a pink blouse.
Conservative; yet still pretty. I had to leave at noon to help my mom
which really bummed me out. I gave Bruce a goodbye blowjob after
lunch. He drove me home, still dressed.
My mom was home and she heard us pull up. She came out to the car and
poked her head through Bruce's window. "Hi, are you coming in Bruce?"
She asked.
"Sure, but just for a bit. I need to get back to work." He stated.
He opened my door for me and led me inside behind mom. Mom made Bruce
some coffee. She turned around after she got it started and saw me and
Bruce holding each other tightly. "My, you two are just glowing," she
said with a smile. "I guess that means you've had a lot of sex!"
"Mom!" I yelled as I turned bright red.
Bruce was red too and said, "I hope that's okay?" he asked.
"That's wonderful. You two look so happy and that's what matters," she
said.
Bruce looked a little relieved. We sat down and Bruce and mom drank
their coffee. She asked about our plans for the following weeks.
Bruce told her he wasn't sure but he wanted to know if it was okay for
him to take me away for a few days. I was shocked! This was great; I
just hoped that mom would say yes.
"Oh, that would be wonderful. Jennifer's never been much beyond the
city limits so I think it's a wonderful chance for her to see other
things," she said.
This made me really happy. Bruce finished his coffee and had to leave.
We saw him to the door and he gave me a deep kiss right in front of my
mom. "Bye pumpkin, see you first thing in the morning," he said.
As soon as he left mom said, "Oh isn't that sweet, he calls you
pumpkin," half teasing.
I turned red and she grabbed my hand and pulled me to the couch. "So,
how was it?" She asked excitedly. It was so much like talking to a
girlfriend rather than my mom that I told her everything! When I was
done I was practically breathless. Then I realized what I had told her
and looked at her shocked.
She gave me a big hug. "That is wonderful sweetie! I'm sorry to pull
you away but I really do need your help getting things in order." I
told her that I didn't mind and ran to my room to change. Mom had laid
some clothes on my bed. They were cute clothes that a regular teenaged
girl would wear. I changed into a pair of shorts and a tank top and
set to work. Bruce called me before bedtime to tell me goodnight. God
he was so sweet!
I woke early after a restless night's sleep. I put on some casual
clothes; a pair of blue jean capri's and a pink t-shirt. I made
breakfast for me and mom. She was amazed to see this. "Well, Bruce
sure has changed you!" She exclaimed.
She drove me to Bruce's and on the way told me that I could stay the
night if I wanted to. I told her that I promised to help her out but
she said that she had things under control. She did say that she
wanted to come by on Friday afternoon on her way to the airport. Bruce
greeted me at the door and fondled my ass as he kissed me hello; and he
did this right in front of my mom! She yelled "Get a room!" I turned
around and she had a big smile on her face as she waved goodbye. Bruce
was ecstatic to hear that I was able to stay the night.
The second we got inside I dropped to my knees and gave him a blowjob.
The day and that night was the same as the prior; except that night I
asked Bruce to move to the larger dildo. Unlike the smaller one this
one hurt a little when it went in but boy did it feel good when he
started fucking me with it! Although I was a little sore afterwards I
knew that it wouldn't be long before he himself would be fucking me. I
think that he knew it too because he fucked me with the big dildo again
Friday morning.
Although I felt like I was walking funny Friday morning Bruce told me
that he couldn't tell. After a couple of hours I felt back to normal
and was actually looking forward to being fucked again!
Since my mom was due over, and it was casual Friday I went with a cute
capri pants, camisole ensemble. Mom arrived at noon and I made lunch
for the three of us. Once again mom gave me a hard time about
willingly making lunch. When we were done Bruce showed mom around
while I cleaned up.
When they came back mom asked me to show her my wardrobe. She was
amazed by what she saw. Most of the clothes had come from Neiman
Marcus and Saks. I guess that I didn't look surprised enough so she
pulled out a cute camisole and matching skirt and told me that together
they cost about $600!
"I noticed that Bruce has a hot tub," she said. "Have you ever used
it?"
"No. He mentioned it once but I said that I wanted to have sex instead
so we did and completely forgot about it. Plus, I looked and I don't
think that I could wear any of her bathing suits without you being able
to tell that I'm not a real girl.
"Nonsense," she said. "Where are they?"
I showed her where they were and she rummaged through and found two
that she thought would work. They were both 2 piece thong sets. One
was pink and the other was white with a really pretty flower pattern.
They both had ruffles along the waist band and after trying them on and
mom doing a bit of embarrassing tucking they actually looked very good.
"When Bruce sees you in one of those he's going to want to fuck you for
sure," she said. Anymore talk like this from her didn't embarrass me.
"So, have you two done it yet?" She inquired.
"No, but he's used the big dildo on me twice. Once last night and
again this morning. It didn't really hurt so I think that I can handle
him after a couple more sessions." I said matter-of-factly.
"Good, you'll notice a big difference with the real thing. It feels so
much better. If you cum just by giving him a blowjob expect to cum
several times in a row when he's fucking you." She gave me a big hug,
"I'm so happy for you. He's a great guy; not to mention he's got a lot
of money and he's hot!"
"Mom!" I said blushing. It made me feel good that my mom was happy for
me; but to say that my boyfriend was hot kind of embarrassed me for
some reason.
"Okay, I have some time before I have to go and Bruce is going to take
you someplace nice for dinner. Let's work on your technique and get
you dressed up nice a cute for dinner," she offered.
I happily agreed and we spent the next couple of hours practicing and
then getting me ready for dinner. Mom was very happy with my progress
in putting on makeup. When it came to my outfit we chose a really cute
white drop waist sundress with a pink bow at the waist. It came to
just above my knees. I would have to say that it was more like a
little girl's dress but made for a teenage woman. We went with little
jewelry and light makeup since this was more of a daytime affair.
Just before I went to put on my dress mom gave me a package. I opened
it up and almost cried at what I saw. Inside was a pair of realistic
looking breast forms! They were a size A and fit me perfectly. From
my perspective the size and shape were perfect. They were on the
smaller side but you know what they say; more than a handful is a
waste. I was so happy! They looked very realistic and allowed me to
show some cleavage without the slightest hint that they were fake. I
gave her a big hug and almost started crying but she scolded me because
it would ruin all of the hard work we had put into the makeup.
Mom showed me how to put on the forms and when I looked in the mirror I
was shocked. It appeared as though I had breasts; even when I was
naked! The added weight caused by the forms was somehow very erotic.
I couldn't wait to show them off for Bruce. However, since the dress
had a square neckline he wouldn't really notice them until I was naked;
or at least wearing some revealing lingerie.
I finished getting ready and went downstairs with mom. The dress was
so light it felt like I was wearing next to nothing even though it was
rather modest. Bruce heard us coming and gave me a big smile when he
saw me. "My oh my you look absolutely adorable!" He walked towards me
and right next to my mom gave me a French kiss while he squeezed my
butt with one of his hands. Mom just smiled. I snuggled into him and
my mom said that she had to go. I hugged her goodbye and we saw her to
the door.
"Your mom's the best pumpkin. I am so happy that she's not mad about
the two of us and she's actually encouraging us." Bruce said.
"Yeah I know," I said. "You're looking rather handsome Daddy. Where
are we going for dinner?"
"There's a nice little restaurant not far from the airport. I'm not
quite ready yet so why don't you go to the sitting room. I got you
subscriptions to a couple of magazines that I hope you'll like."
"Thank you Daddy!" I said. I was wondering if they were porn magazines
but was pleasantly surprised to see that they were fashion and gossip
magazines for young girls. There was Seventeen, Teen Vogue, Cosmo Girl
and others. They offered all sorts of fashion and makeup advice for
girls. I couldn't believe that I now found things like this
interesting but I did.
I sat down to read and Bruce came to get me after about half an hour.
He took me to a nice restaurant. We sat outside and it felt wonderful
to be outside in a pretty dress with everyone calling me Miss. I don't
think that anyone suspected a thing which was a tremendous boost to my
confidence.
When we were done Bruce held my hand and we went for a walk to window
shop. We walked by a teen clothing store and Bruce took me inside.
"Buy whatever you want sweetheart," he said.
"But honey, I already have so many clothes that I don't know what to do
with them!"
"Nonsense," he said. "Here's credit card with your name on it. You
have a $2,000 dollar balance and I expect you to use it. I'll pay it
off every month and if you don't use it I won't let you give me a blow
job for an entire week," he whispered with a grin.
Of course I knew darn well that he was lying but I wasn't about to make
sure. I gave him a kiss and we walked about the store. It was full of
clothes for a fashion conscious teen which means camisoles, short
skirts and dresses. I tried on a ton of clothes but didn't let Bruce
see me in any of them. We were weighed down with packages when we
left. I was so happy! I couldn't wait to get home and give him the
cock sucking of his life. However, I was surprised when he didn't head
for home but we actually came to the airport.
"What's going on?" I asked.
"You and I are taking a romantic trip. You're mom said that it was
okay so I booked us a flight to a small island in the Bahamas."
I couldn't believe my ears! "But I don't have anything to wear except
for the clothes that I just bought."
That's okay pumpkin. I packed for you. You may be able to fit a
couple of things in one of your suitcases but the rest will have to
wait until we get home.
Bruce parked the car in the parking garage and I looked around before
giving him a big kiss and unzipping his pants. "But baby, someone
might see."
"I don't care," I said. "I want your cum and I want it now." As you
can guess he didn't put up a fight.
He was already hard and it didn't take much sucking to get him to cum.
I was getting used to his huge loads and swallowed this one with
relative ease. My God it tasted great!
Before we left I fixed my hair and makeup in the mirror. Bruce allowed
me to pick out a couple of cute camisoles and skirts which he put into
the suitcase himself. He didn't want me to see what he had packed so
he made sure I didn't watch.
We had first class tickets and snuggled close throughout the flight.
We arrived in the Bahamas in the early evening and got on a small prop
plane which took us to the island Bruce had chosen. I have to tell you
that I didn't much care for it. Bruce sensed this and held me tight
through the 15 minute flight.
We arrived at the island and were greeted with Champaign at a small
villa. We were shown to our room. It was huge! It had an indoor hot
tub and a big balcony facing the ocean. Bruce ordered in some food and
wine and we sat on the balcony eating and drinking. It wasn't long
before I was pretty tipsy so Bruce cut me off. We made out for a while
before going to bed.
I felt terrible when I woke up the next morning, but not from a
hangover. Here we were in a beautiful place on a small island in the
Bahamas and I didn't even give Bruce a blowjob. I decided to remedy
the situation by going down on him even before he woke up. I giggled
to myself because he started to get hard the second I touched his cock.
I kissed it to life and began going at it in earnest. I don't know
when he woke up but it wasn't too long before he started squirming
around and announced he was going to cum. Since I knew that he liked
to cum on my face and he also liked to see me lick up his cum I
positioned my head about 6 inches from his cock and jacked him off. He
shot all over my face and the cum fell back down to his body. There
were strings of cum between my face and his body and I knew that I
looked like a mess.
"Good morning," I said. The strings of cum moved up and down across my
mouth when I said it.
"What a wonderful way to wake up pumpkin, thank you," he said. I
licked up all of the cum from his body and then moved up and laid on my
back beside him. He got up on one elbow, "you missed some."
"Sorry about that. Would you mind feeding me daddy?" Without
answering Bruce proceeded to use his fingers and scoop the cum off of
my face and feed it to me. When he finished he kissed me long and
deep. I apologized for not sucking him off the night before but he
would have none of it.
I showered while Bruce ordered breakfast in. When I got out of the
shower I saw that he had laid out some clothes for me. There was a
note on top that read 'I want to take my darling little princess out
for the day. I hope you like the outfit that I chose for you. Love,
Daddy'. The outfit consisted of a tiny white halter top and a tiny
black miniskirt. Since Bruce wanted a little girl I decided to forego
the breast forms and go with a flat look. I went with a little girl
that wants to look grown up but doesn't quite succeed look for the
makeup. I pulled my hair back to either side with cute little clips.
When I looked in the mirror I saw a cute girl of 11 or 12 looking back
at me.
I walked out and Bruce was on the balcony. I hadn't looked outside
since we got there. The view was absolutely incredible! Bruce heard
me coming and turned around. "There's daddy's little girl. My-oh-my
doesn't she look adorable!" he said. He came up and lifted me up and
kissed me. "You look so fucking hot," he said into my ear. This
absolutely thrilled me. After making out for a minute he excused
himself to get showered and dressed.
Room service came while he was still in the shower. I answered the
door and the teenaged boy that brought the food leered at me. He had
that I'd love to fuck you look on his face. God, I loved getting that
look. Talk about a boost of confidence! Bruce came out not long
afterwards and we ate breakfast on to balcony. There was a light
breeze and I must say that I loved the feeling of the wind blowing up
my skirt.
Bruce decided that we'd take a walk and visit the shops before lunch
then we would hang out on the beach. "I guess we'll be father and
daughter today," I said.
"Are you kidding me? I'm spending this vacation with my underage
girlfriend. In fact I don't think there's such thing as having an
underage girlfriend here."
Well, I sure liked that idea! We freshened up and went for our walk.
The place that we were staying was small and only had a couple of
rooms. It was very fancy and must have cost a fortune.
Bruce and I left holding hands but for most of the walk he had his hand
under my skirt, fondling my ass. It was funny because nobody paid much
attention except for some of the guys. I could feel their eyes on me
as we passed. Bruce bought me some pretty jewelry and a very skimpy
dress which I absolutely loved.
We ate lunch at a small café before heading back to our room. Once
there I asked Bruce if he wanted a blowjob but he said that he thought
he could hold it until that evening. I went to the bathroom to change
into my bathing suit while Bruce changed in the room. Bruce gave me a
new bathing suit to wear. It was a thong but from the front it looked
like something a young girl would wear. It was white with little teddy
bears all over it. It was very cute.
I came out and was pleasantly shocked to see Bruce in a thong as well.
He had a very sexy butt and it looked great on him. The front bulged
out with his huge cock. I know that we would both attract the eyes of
the opposite sex. We walked to the beach holding on to each other's
ass. The day was spent in the sun and water.
For dinner Bruce picked out a cute little dress for me to wear. Again,
he went with the 12 year old look. It was pink with a little white
lace peaking out on the bottom.
Afterwards we went for a walk on the beach, holding hands the entire
time. We were near our inn when Bruce turned to me and said, "I love
you." I couldn't believe it! I was hoping that it would be said at
some point but I didn't know that it would happen so soon. I was so
shocked that it took me a minute to tell him that I loved him too. We
shared a long, romantic kiss. I snuggled into him and we both quietly
confessed out love again.
We walked slowly back to our room. Bruce set out a cute white short
babydoll to wear and had set a little teddy bear on top of it. As I
was getting ready I gave it a lot of thought and decided that tonight
would be the night. Although I wasn't sure I could take him I thought
that I'd give it a try. After all he had done for me I wanted more
than anything to feel him inside of me.
I got ready and found Bruce in bed once again sporting a huge hard-on.
The lube was on the table along with the big dildo, and the video
camera was set up once again. Bruce eyed me fondly as I walked over.
He was surprised when I grabbed the dildo and said, "We won't be
needing this tonight."
There was a look of shock on his face as he looked up at me. "Are you
sure pumpkin?" I shook my head yes and he pulled me down to him.
"I'll be gentle," he whispered. He looked deep in my eyes. "I'm sorry
princess but I'm close to cumming already, would you mind giving me a
blowjob first? I'll last longer that way."
Of course I didn't say a word as I jumped between his legs and started
to suck him off. It only took about 30 seconds before he shot a huge
load in my mouth. I swallowed a couple of times and held the rest in
my mouth. When he was done I looked up at him and showed him his load.
I swallowed and opened my mouth again to show him that it was all gone.
His cock never got soft. I gave it one last kiss before snuggling up
to him.
We kissed; our bodies intertwined when Bruce pulled his face away and
gave me a tender look as if asking me if I was still okay with this. I
gave him a look of pure love thus letting him know that I really was
ready. He reached for the lubricant and towel and moved down between
my legs. He moved the string of my g-string out of the way and began
to lovingly lap at my asshole. I was mewing quietly as he worked his
magic.
Once Bruce felt I was relaxed enough he placed the towel underneath me
and began to lube me up. He worked his way up to three fingers to get
me ready. He was more generous with the lubricant than ever and made
sure that his cock was coated as well. He then lifted my legs onto his
shoulders. There I was spread eagle on the bed with my legs on his
shoulders. He looked so huge and I felt so small and vulnerable. He
led his cock to my asshole and as I felt the tip touch me something
happened and I completely relaxed. He was actually able to get the
head inside of me easily. As the largest part of the head entered me I
let out a little gasp and came in the most intense orgasm I had ever
experienced up until that point in my life. I looked at Bruce and he
looked down at me with a loving smile. He proceeded to gently push in
and then pull out without ever completely leaving me. He worked up
until he was halfway in me and when I looked up he appeared to be in
more pain than I was at the moment. "My God, Jennifer you're so
incredibly hot and tight I can hardly take it."
As Bruce worked himself further and further into me the pain was
beginning to be very hard to take and I was ready to say something when
I felt his body against mine. He was completely inside of me and the
thought of that alone made me cum yet again. He lowered himself down
to me and with a big smile said, "We're one now love. How does it
feel?"
I began to cry. "Lovely," I said through my tears. He smiled, said,
"I love you baby," and gently kissed me. He continued to shower me
with kisses as he slowly and gently began to make love to me. I can't
describe the feeling only to say that I wished that it would never end.
Sadly, but gloriously it did end about 20 minutes later. With one last
push he burrowed into me deeper than ever and began to cum. As I felt
him pulse inside of me I came yet again. Feeling him shoot into me was
not at all what I expected. I could feel each pulsed of his lovely
cock and felt each spurt as it shot into me and made me feel wet
inside.
Bruce rolled over on his side and carried me with him so that he would
remain inside of me. I felt the pressure ease a little as his cock
began to soften. I fell asleep in his arms before he fully left me,
and didn't wake up until the next morning.
I woke up to a knock at the door. Bruce had already showered and
ordered breakfast. I was lying in bed looking disheveled and awful. I
got up to run to the bathroom when Bruce yelled "Don't get up or you'll
be in trouble young lady!" He walked in and I covered myself with the
sheet. He pulled it back from my head and asked "And just what is
wrong with you?"
"I look terrible. Let me go and get cleaned up."
"Nonsense, you look absolutely beautiful and you are going to stay in
bed and eat breakfast. You can get ready afterwards." Bruce kissed my
forehead and sat besides me as we ate.
We finished and I showered. Bruce left me a new bathing suit with a
note that read 'For my sexy little vixen. Your lover, Bruce.' This
one was shiny gold and very sexy and was more of a g-string than a
thong. It had a bit of ruffled skirting at the waistband so with some
adjustment I was able to hide myself quite well. I decided to go with
my breast forms since I guess I was supposed to be a little older
today.
I came out of the bathroom and Bruce looked at me shocked. "Oh my God,
those look spectacular, where did you get them?" I told them that my
mom gave them to me on Friday. He stormed up to me and picked me up
and held me tight. "They're perfect lover." I smiled and we kissed as
he rubbed my ass. "How do you feel?"
"Actually, I feel really good. I think that I'll be ready to go again
tonight with no problem."
"Good, because you have the hottest little ass I've ever seen."
I smiled and walked away from him to let him have a good look at it.
When I turned back around his cock was peeking out from the waistband
of his bathing suit. I ran over, dropped to my knees and began to
noisily suck on it. Once again I was favored with a big load that I
showed to him before swallowing.
We spent the day at the beach and in the water. We made out in public
like two high school lovers and our hands rarely left one another's
body.
We went back to our room to clean up and get ready for dinner. I went
to shower and Bruce left me a note. 'I want to have dinner with my
hot, somewhat slutty looking girlfriend. Here's a dress for you to
wear. Love, Bruce." The dress was next to nothing. It had a plunging
neckline so I decided to wear my breast forms. The dress was cut very
low in back. It was so short that you could actually see the bottom of
my butt cheeks. So, if it was slutty he wanted it's slutty he would
get. I put my hair in an up-do with several small tendrils hanging
down. I really overdid it with my makeup but was proud of my look.
Slutty, yet not like a cheap whore. More like a girl that wanted to
get fucked, and fucked hard. I put on very high heels and a lot of
jewelry and went out to see Bruce.
"Holy fuck," he said, "you look fucking hot!"
"Why thank you kind sir. If you keep this flattery up you may end up
doing more tonight than just saying fuck," I said with a naughty grin.
With that Bruce placed his hand under my dress and on my ass and led me
out the door. We went to a nearby restaurant and turned the head of
every man in the room. Some of the men got caught by their wife or
girlfriend and reprimanded which was followed by a disapproving glare
from a couple of the women. Bruce wanted to show me off so we sat at
the bar. The dress rode up impossibly high as I sat down on the bar
stool but I didn't bother to pull it down. For the most part Bruce ate
dinner with one hand because his other hand was busy massaging high up
my inner thigh.
When we finished Bruce asked me what I wanted to do next. "Well, we
could either go for a long walk or you can take me home and fuck my
brains out." Bruce chose the later which was evident by the fact that
he pulled me from my chair, shoved his hand under my dress so my ass
was fully exposed for all to see and led me out of the bar.
We made it back to the room in record time and as soon as Bruce slammed
the door shut he turned around and ripped my dress off. I mean that he
actually grabbed the dress with two hands and tore it open. I was
standing there in my thong and heels as he took off his clothes,
leering at me the entire time. When he was completely naked he picked
me up and carried me to the bed. He threw me on the bed so I was on my
belly with my ass sticking up in the air. He grabbed the lube by the
table and poured it into his hand. He coated his cock over my ass so
the extra lube dripped down onto my asshole. He grabbed his cock and
gently but firmly began to feed it into me. Once again I came when he
was all of the way inside of me. I looked over my shoulder and said,
"Fuck me." Which he proceeded to thoroughly and soundly do.
Although it was intense he was still very gentle. I began to squeal
loudly as he grunted with each thrust. He would periodically ask me if
I was okay and I would always say "Yes, please don't stop." He fucked
me for about 10 minutes before shooting into me which made me cum yet
again. However, he didn't soften he just began to fuck me a little
more gently. Soon he was back to full power and we were in full rhythm
with one another. Sweat began to pour from out bodies as we made love.
I lost track of how many times I came before he did. This second round
must have lasted a good 20 minutes and we were both exhausted by the
end.
"I love you," he said when he finally caught his breath.
"I love you too," I whispered into his chest.
The next two days were much the same. We were both insatiable. I blew
him twice a day and he fucked me before going to bed both days. By the
end we were both sexually and physically exhausted. I was disappointed
when the trip was over but I knew that we had to get back to work. By
the time we got back to Bruce's house we were both too tired to fool
around so we cleaned up and went to bed. I loved the sex but I knew it
was more than just sex when we could fall asleep in each other's arms
without anything more than a sweet goodnight kiss.
I awoke early the next morning and decided to dress sensibly since we
had a lot to do and I didn't want to distract him. However, it didn't
work and as soon as he came down for breakfast and saw me he got a hard
on so I blew him.
We worked hard the rest of the week and I gave him the usual morning
and lunch blowjobs and we had the nightly fucks. I was in heaven. I
had gotten comfortable with the size of his cock so there was rarely
any pain. He was so gentle and loving while he fucked me; showering me
with kisses and I love you's. In fact the only time that he fucked me
hard was our second night together.
Since Friday was a casual day and we had pretty much caught up I
decided to wear a cute white cropped camisole and a blue jean
miniskirt. Bruce had to look at a property in the morning so he didn't
get a chance to see what I was wearing. He called me at about 1 when
he was headed home so I could get lunch ready.
Lunch was on the table when Bruce arrived. I gave him a big hug and
kiss when he came into the kitchen. Since he missed his morning
blowjob and it was late for his noon blowjob he wasn't as hungry for
food as he was for sex. His hands went under my skirt as he shoved his
tongue down my throat. I reached into the pocket in my skirt and
pulled out a little package of lube that I had put there just in case
he wanted to fuck me. That way we wouldn't lose the mood by having to
run and get some. When he saw what I had he set me down on the table
and ripped off his shirt and pulled down his pants. I got off the
table to get on my knees and suck him off for a bit but he didn't want
that. He pulled me up as I was bending down and turned me around. I
got his idea and laid myself prone across the table with my feet on the
floor.
I felt Bruce come up behind me and press his cock to my asshole. With
one hard shove he entered me to the hilt. It hurt but felt incredible
at the same time. I let out a grunt like the wind had been knocked out
of me. Bruce began to fuck me hard. I mean he was slamming into me
and you could here the slap of skin pounding against skin. He had a
hold of each ass cheek and would periodically let go of one and slap it
hard. I couldn't believe that I was being fucked like this much less
enjoying it. He pounded me like a jackhammer for about 10 minutes,
periodically yelling out the word fuck before slamming into me one
final time. He let out a loud yell and I felt his cum squirting deep
inside of me.
He collapsed on top of me. We were both working hard to catch our
breath as sweat poured from our bodies. When he could finally speak he
said, "Hi babe, I missed you."
I laughed, "I never would have guessed. Wow that was intense."
"I'm sorry baby; I hope I didn't hurt you."
"I'm okay, but you may have to settle for blowjobs for the rest of the
day."
He laughed and asked me if I was sure that I was okay. I told him that
I was fine, which I was. When he pulled out I felt his cum pour down
my legs. I was convinced that it was his largest load ever and I
wished that he had shot it into my mouth.
I showered and changed into a pair of jean capri pants and a red tank
top and since we were so tired following that fuck we didn't do
anything for the rest of the day except relax.
I wanted to conduct my little test on Saturday so I held Bruce off
until just after dinner. I wore a cute little dress and fixed him a
nice dinner. Afterwards I got a 2 cup measuring cup from the cupboard
and placed it on the table. I went and got the video camera and turned
it on and handed it to Bruce. Bruce looked at me curiously as I got
down on my knees and began to take his clothes off but he didn't say
anything.
I kissed and licked him to life and began to suck. I stopped for a
second, looked up at him and said, "Tell me when you think that you're
getting close to cumming but not too close, okay?" I wanted to get as
big a load as possible so I figured this was the best way to build up a
lot.
"Okay, but only if you tell me what you're doing first."
"I'm just conducting a little test is all. Promise to let me know?"
He agreed and I got back to work. I went at it for about half an hour
or so; stopping periodically to blow on his cock to calm him down.
Eventually my mouth started to get tired and I thought that I wouldn't
be able to calm him down again anyway so when he said that he was close
I grabbed the cup and got ready. A couple of licks and kisses later he
began to cum so I pulled away and began to jack him off into the cup.
It was kind of like milking a cow actually, which caused me to start
giggling.
He shot a very big load and when he was done I licked his cock off
figuring that it was a small amount and I didn't want it to go to
waste. Bruce's breathing calmed down as I help the measuring cup up to
take a look. I was amazed to see that there was a little over a cup of
cum. "Wow, almost 10 oz!" I exclaimed to Bruce.
He laughed and said, "You're goofy. What are you going to do with it
now?"
"That's a silly question," I said and then I took the cup and drank it
down. It was a little different drinking his cum from a glass. Bruce
obviously enjoyed watching me do it and smiled as I licked the glass
clean. "Good to the last drop," I said with a smile.
Bruce gave me a big kiss before leaving to watch TV while I cleaned up
the kitchen. I couldn't believe how much I enjoyed it. I even liked
it when he called in and asked me to bring him a beer. I did and
snuggled up on the couch with him to read Seventeen while he watched
the game.
That night he made long, slow gentle love to me. Nothing hard; even
when he came. He just pushed in a little further and I felt him
release several spurts. It was awesome.
In the morning he gently fucked me again. We did it in the missionary
position and since I had to change the sheets anyway when he was ready
to cum I asked him to pull out and cum on my face. He didn't make it
all of the way up to my face before he started to shoot his load so
some of it ended up on my chest. When he was done cumming he scooped
the cum up a bit at a time and fed it to me. It was romantic and
erotic at the same time.
After I was pretty well cleaned up I went down to fix breakfast for
Bruce while he showered. When he came down I gave him a kiss and said,
"Well I better take a shower, your cum's starting to harden in my hair
and if it gets too hard it'll be a pain to get out."
"But you look so sexy," he said with a grin. He gave me a little swat
on the butt as I left to shower. I decided to wear a knee length white
skirt and pretty lace blouse. We weren't planning on going anywhere
but I wanted to dress up a little just because it was fun.
I went downstairs and heard Bruce talking to someone. I thought that
he was on the phone but when I walked into the room his brother was
standing there. I recognized him from the pictures. I panicked
because I didn't know if Bruce had told him anything about me. I was
considering sneaking out when Bruce said, "Oh there you are babe, come
on in and meet Rick."
Rick turned around, "Hi! You must be Jennifer. It's great to meet
you." He shook my hand and gave me a big smile. He sure seemed nice.
"What does a beautiful young girl see in a big old man like him?"
This made me laugh, "He's pretty sexy for a big old man." I walked
over to Bruce and snuggled into his chest.
We went outside and just chatted. I really liked Rick and was glad
when he decided to stay for lunch. When I was bringing it out I
overheard him tell Bruce how hot I was and ask if I was any good in
bed. Bruce told him that I was spectacular and he'd never come close
to experiencing sex so good. This made me feel absolutely wonderful.
Rick left and Bruce and I were basically inseparable the entire two
weeks that my parents were gone. The sex never slowed down and I was
so used to having his cock in my ass that it didn't hurt anymore. One
day I spent the entire day in lingerie. Bruce did me 3 times and I
gave him two blowjobs. We took the day off the day before my parents
returned and spent the day out. We ate all three meals out and Bruce
bought me a bunch of clothes and jewelry.
I was so disappointed when my parents returned. I wouldn't be able to
spend the night with Bruce every night like I had done the past two
weeks. Bruce took me home the morning of the day of their return. I
wore a pair of cute white shorts and a pink camisole. I tidied up the
house and had dinner ready when they arrived. I was happy when my dad
gave me a big hug and told me that I looked really cute. Mom asked me
for all the sordid details which didn't embarrass me anymore. I was in
love and I really didn't care what she thought.
The Rest is History
Over the summer my hair grew down to the middle of my back. I was
always in girl mode and Bruce and I continued our love affair. I never
grew tired of him or his wonderful cock and the tasty cum that came out
of it. I never tired of blowing him or getting fucked by him. We had
done it everywhere in the house and pretty much everywhere outside. He
came over to my house often and we would make out on the couch while we
watched TV with my parents. My mom even walked in to my room not
knowing that he was there. Bruce didn't see her but she gave me a grin
as she saw him plowing me doggie style. "You two fuck like rabbits,"
she said with a smile when she saw me later.
I met his sister during the summer and I got along with her very well.
She helped me with my makeup and we would sometimes go shopping for
clothing together. I also met many of his friends. We had everyone
over for a barbeque and they were all very nice. I overheard a number
of them telling Bruce how hot I was.
As fall and the beginning of school approached I had a lot of thinking
to do. Going back meant cutting my hair and spending time as a boy.
Not completing at least my high school education would doom me to a
life of low paying jobs. However, if Bruce and I were to get married
it wouldn't matter anymore! I was doing my best to make him happy;
which in turn made me happy. I dressed how he wanted me to dress,
cooked and cleaned and brought him drinks, and I offered him my body
whenever or wherever he wanted it.
There were days he would cum all over me and I would spend the day
coated in his cum even as it crusted up on my face and body. I'd jack
him off onto my food and eat it for him. A salad loaded with cum
dressing tastes surprisingly good! These things were actually my idea
and they turned me on as much as they turned him on.
I looked into my options for going to school and after some convincing
mom allowed me to drop out as long as I promised to get my GED before I
would have graduated anyway. Bruce was so happy with the idea that he
took me to Hawaii to celebrate. It was there that he asked me to move
in with him. I told him yes even before asking my parents. If they
didn't like it that was too bad. I wanted their support but Bruce was
more important to me than anything in the world. Luckily they were
okay with it. Not overjoyed but they didn't object; which was probably
the best that I could have expected.
I left my boy clothes at their house and moved in right as school
started. Bruce had set up a separate office for me to study for
school. It was really girly. Everything was pink and there were
posters on the walls of famous guys that I liked. He even put up a
collage of facials that he had given me. There were also a lot of
photos of the two of us dressed and holding hands or kissing. I made
the mistake of inviting my mom in once and she saw the collage. "I
guess you weren't lying about how much cum he shoots," she said with a
laugh. I turned really red since I hadn't told her that Bruce liked
cumming on my face. However, she didn't seem offended and reprimanded
me for getting embarrassed.
For our first Christmas together Bruce gave me 3 things. The first was
a fake social security card and the second was a fake birth
certificate. He said that I could use these to get a driver's license
when I turned 16. My name was now Jennifer! The last one was the best
of all. It was a boob job! I got my fake boobs soon after. A friend
of his was a plastic surgeon and he performed the procedure. They were
a small B cup which suited me just fine. He also began prescribing low
doses of female hormones. They made me even softer than I was and
didn't lower my sex drive. We looked into sex reassignment surgery but
decided against it since the hormones would lower my sex drive and any
pussy they created wouldn't be able to fit his huge cock.
The years flew by and Bruce and I were still madly in love. We spent
all of our time together and were both happy to see that I didn't seem
to be having a growth spurt. I should have assumed this since both of
my parents were on the small side.
For my sixteenth birthday Bruce bought me a red Volkswagen convertible.
I always commented on how cute they were and he said that he couldn't
resist. I drove it to my parent's house for Christmas dinner. I
didn't know it but Bruce spoke to both of my parent's when he sent me
back to our house for a bottle of wine we had forgotten.
We ate dinner and as I was cleaning up Bruce came up to me, got down on
one knee and asked me to marry him! I screamed and of course I said
yes. The diamond was huge and when pressed by withholding sex I found
out that I cost over $200,000! We both wanted a smaller wedding but we
also wanted it to be elegant so we planned to do it the following
summer.
My dress was custom made. It was part fairytale princess and part
sexy. The bodice was like a corset. It was really tight, had a
plunging neckline and was essentially backless. In fact it went down
to just above the crack of my ass. The bottom was a huge skirt with a
lot of lace.
I spent a lot of time on the vows. I wanted to come up with something
that I knew that Bruce would like. I had found that over time I was
becoming more and more subservient to him. I actually enjoyed it and
he didn't overly take advantage of it. He was my protector and I was
his little woman. So, the vows that I wrote were quite fitting. My
mother said that she never would have said them but they did seem to
fit my relationship with Bruce.
Bruce's lines:
I, Bruce, take you, Jennifer, to be my wedded wife. With deepest joy I
receive you into my life that together we may be one. I promise you my
deepest love, my fullest devotion, and my tenderest care as my
beautiful, frail and sensitive wife. As your loving and tender husband
always will I perform my headship over you as the strong shall over the
weak. In recognition of these things, Jennifer I purpose to love you,
to provide for your needs, and to lead you as I see fit. I lay down my
life for you, Jennifer, my friend and my love. Today I give to you me.
My lines:
I, Jennifer, take you, Bruce, to be my wedded husband. As you have
pledged to me your life and love, so I too happily give you my life,
and in confidence submit myself to your headship. I stand here today to
proclaim and declare that I will fulfill each and every request of my
husband, every day and night, till he is satisfied. I desire to be
trustworthy as your wife by following your leading submissively. I vow
to spend every waking moment of my life being as beautiful and
satisfying as you desire. I will live unto you, serving you, loving
you, obeying you, caring for you and ever seeking to please you. Our
Father created woman to be man's helper. It is my desire and delight to
follow this teaching. Therefore, throughout life, no matter what may
be ahead of us, I pledge to you my life as an obedient, faithful and
loving wife.
The rest, as they say, is history. We lived happily ever after. We
never grew tired of sex and I continued to worship his cock and drink
his cum for years to come.
I hope that you've enjoyed reading this. Most of the outfits that I
describe in this story are based on outfits found on apparel store
websites. If I have time I'd like to post them on the web for all
readers to see. Send me your feedback at jn01820@yahoo.com