Sara 1
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It's amazing the things you remember from your childhood on important
days of your life. Today I remember when my father died from pancreatic
cancer when I was seven. I remember the funeral that followed and the
sadness in my mother's eyes as we left the gravesite. He was fifty-two
years old.
My mother married my father when she was twenty-one and he was forty. Of
cause everyone told her he was too old for her but my mother didn't care
they were in love. It took five years for their love to bear fruit.
My mother had been trying to have a baby since she and my father had
first gotten married. When they finally resigned themselves to being
childless I came along. Though I was a two and a half months premature
and only weighed two pounds and three ounces I was a welcome sight to
both of them.
As a child I was never sickly though due to my premature status I never
grew into the strapping young lad that my parents had hoped for. By the
time I was sixteen I stood around five foot two and weight less than
ninety pounds.
This is not to say my mother was disappointed in me. No she was quite
proud of me. I was an "A" student and captain of the debate team for my
high school. I was also a good actor though the roles I could play were
hampered by my small stature.
My mother didn't coddle me at all. When I reached the age of fourteen I
was put to work in the family restaurant that she and my father had
started. At first I was a busboy cleaning up after our customers had
left. I became a waiter at fifteen and then host at sixteen.
The restaurant was quite successful in our small town, as everyone who
lived in the town either came in to eat or ordered from our take out
menu. Our home delivery service was a booming business employing several
boys from the high school.
On my seventeenth birthday I was given a new car from my mother. The
next day the reason I was given the car was apparent. My mother pressed
me into service taking deliveries. It really wasn't that bad as it got
me out of the restaurant. Besides the tips I received were quite
generous.
Most of my work time I spent in the restaurant but several times a week
I would have to run one or two deliveries. It was mostly when one of the
other drivers didn't come in. Like on nights when there was a game at
the high school. It was on one of these nights that I met Stan Franklin
for the first time.
Stan was not one of our local residents. He owned a large two story home
about ten miles outside of town that he lived in on the weekends. During
the week he would go back to the city and live there until the following
Friday.
I knew exactly where his house was, as my mother had pointed it out
several times. She was quite proud of the fact that he would pay extra
for one of her meals. We normally didn't deliver that far out because of
the cost to the driver. Stan was the exception seeing he made it worth
the driver's time with a generous tip.
I remember vividly the night I first met Stan. I had just turned
eighteen three weeks earlier. I was looking forward to graduation from
high school in less than two months and going on to a college in the
fall. On that night I had to deliver four other meals before I made it
to his house. The drive up to the house was well lit and there was a
light on the front porch. As I reached for the doorbell I saw my hand
was shaking slightly from nervousness.
When he open the door I was take aback by the size of the man. He stood
six foot five with very broad shoulders. He had brown wavy hair and
brown eyes. He was so huge I felt even smaller than I really was. He was
younger than my mother by about ten years.
Stan smiled down at me and said, "You're the owners son, Scott isn't."
I can't tell you how thrilled I was. No one took notice of me before. I
smiled back and said, "Yes Sir Mister Franklin I have your order."
"My name it Stan not Mister Franklin," he told me as he took the
package. After looking at the receipt he handed me a fifty-dollar bill
and said, "Tell your mother she makes the best Italian food I ever
tasted."
As I tried to give him his change he waved me off saying, "You keep the
change." I then thanked his as he closed the door. It wasn't that
spectacular of a meeting but to me it was a memorable one.
My second meeting came about a month later. I had an order for Stan that
was the only one I made that night. When I arrived at his house instead
of answering the door he asked who it was over an intercom.
"It's Scott from Teresa's restaurant. I have your order," I told him
through the intercom.
"Boy that was fast. I just got out of the shower come on in and I'll be
right down," he told me.
Seeing the door was unlocked I opened it and stepped inside. I placed
his order on the hall table and waited for him to come down. A few
seconds later I heard what sounded like moaning coming from the room to
my left. It sounded like a girl in pain. My curiosity got the better of
me as I stepped up to the door where the moaning was coming from and
looked inside.
I looked into what appeared to be a sitting room with a large screen TV
on one wall. On the TV I saw a naked girl lying on her back with another
girl face down in the first girl's lap. The girl on her back was moaning
as the other girl was licking her pussy.
I've seen those adult movies on the premium channels we had on cable but
those didn't show it in the detail that this movie did. In this movie I
could see the girls tongue go into the other girls slit as she licked
her.
It wasn't until I felt the hand on my shoulder that I realized what I
doing. I must have jumped ten feet in the air as Stan chuckled and said,
"Calm down buddy."
"Sorry Mister Franklin I shouldn't have been watching. I mean it was
wrong for me to watch that sort of thing," I told him as my face started
burning with embarrassment.
Stan chuckled again and said, "Don't worry about it I watch it all the
time. If you would like you can stay and see the whole movie."
I could feel myself blush even deeper as I said, "No I have to get back
to the restaurant. My mother wouldn't understand."
"Okay buddy maybe next time," Stan told me as he put his hand on my
shoulder. He steered me toward the door as he placed a fifty-dollar bill
in my hand and said, "You could come back after work and watch. I'll be
up till three or four in the morning."
"I don't think that would be a good idea. I don't think my mother would
like me being out that late," I told him.
Stan squeezed my shoulder and said, "Maybe some other time then." He
then walked me to the door. It wasn't until then I realized he was only
wearing a pair of boxers and a short robe.
Two weeks after this incident I was standing in the restaurant seating
customers when Stan walked in. As far as I knew this was the first time
he ever came to the restaurant.
Stan smiled down at me and said, "A table for one if you please." As I
walked him to he table he said, "I expected you to come back last week.
I was disappointed you didn't."
"I'm sorry. It's not easy for me to get away from my mother. I don't
usually go out after we close," I told him.
"You're a senior now aren't you," he asked as he took his seat. I nodded
my head as I handed him the menu. Nothing more was said as I had other
people to seat.
After Stan finished his meal he was standing by the check out with my
mother when she called me over and said, "Scott honey Mister Franklin
said he knows a few professors at NYU and he thinks he can help you get
in. I know your grades are good and your SAT's are outstanding but it
never hurts to know some one that knows some one."
I was shocked by what they were saying. First of all how did he know I
wanted to go to NYU? That was my first choice and the one I hoped would
except me.
Before I could get over my surprise Stan said, "Why don't you bring over
your application after you're through here and I'll go over it with you.
On Monday I'll give it to my friends and put in a good word for you."
"He can go now. I wouldn't want to inconvenience you," my mother told
him.
"Scott I'll see you in an hour or so. Teresa thank you for a wonderful
meal as always." Stan told us just before he left.
After Stan was gone my mother said, "Scott go home and change into
something nice before you go over there. You want to make a good
impression on Mr. Franklin. Don't over stay your welcome but don't run
out on him either. We don't want him thinking we're using him."
"Okay Mom but how did he know I wanted to go to NYU?" I asked.
"I told him," my mother told me as if it made perfect sense. Then she
explained. "He asked me if you were going to college and I told him you
want to go to NYU. That is where you want to go isn't it?"
I had no idea what was going on but I wasn't about to turn down an offer
for help. So I went home and showered then put on a clean pair of khakis
and a polo shirt before driving out to Stan's house.
All the way to his house I wondered if he was serious about helping me
get into NYU or was this just a ploy to get me away from my mother. I
wouldn't mind seeing some more of the porn movie I had seen, but I
wouldn't mine help getting into school either.
I didn't even have to ring the doorbell this time as Stan open the door
before I reached it. "Come on in Scott," he told me. Stan must have come
home and showered too as his hair was wet and he was now wearing a pair
of black pajama pants and a black silk robe. I could see his bare chest,
as he didn't bother to belt the robe.
Stan took the application from me and said, "I'll get us a couple of
beers and we'll look these over."
"You were serious about helping me?" I asked.
"Of course I was, why else did you think I would want you over here." He
asked.
I could feel myself blush as I said, "I thought you might be giving me
an excuse to watch some more of those tapes you have.
Stan laughed and said, "Well the real reason was for the school but that
doesn't mean we can't watch a few fuck flicks when we're done."
Stan told me to go into the room with the TV while he went for the
beers. When he came into the room he was carrying a glass of beer and a
bottle. He sat the glass in front of me and took a swig from the bottle.
After he sat on the sofa next to me he started going over the
application. For the next half hour he made changes and asked me lots of
question. He would take drinks from the bottle and he made sure I took
drinks from the glass. When he was done he put the application into a
leather folder.
He finished off his beer and put his arm around my shoulder and said,
"Well Scott as far as I can see you should have no problem getting in.
I'll grease the wheels a little but mostly it will be your merit that
gets you in."
"Do you really think I can get in?" I asked and I'm sure my excitement
was showing.
Stan handed me my beer and said, "I have no doubt next September you'll
be in class at NYU. Now drink up and I'll get us a few more beers before
I put in a tape." I had only finished half my beer so far but seeing I
didn't want to disappoint Stan I drained the glass in one drink.
While Stan went for more beer I realized that the alcohol in the beer
was starting to affect me. I could already feel my head was slightly
dizzy. I knew this was from the fact that I never drank much before. I
had wine at dinner with my mom quite often but never more than a small
glass and even that would give me a slight buzzing in my head. I also
knew I would have to drink the next beer slowly as I had to drive home.
Once Stan came back from the kitchen he placed the beers on the coffee
table and then when over to the TV. As he put a movie into the VCR he
said, "This is the movie you saw last week I figured you would want to
see the rest of it."
After he sat down he handed my beer to me as he took a drink of his own.
As I tilled the glass to my mouth Stan reached over me for the remote.
As he did his shoulder hit the glass and dumped the glass of beer all
over me.
We both jumped up at the same time and Stan said, "I'm so sorry Scott.
God you're soaked."
"It's okay it was an accident. I'll go home so I can changed," I told
him even though I didn't want to go. I was looking forward to watching
the movie.
"I don't think that's a good idea Scott," Stan told me. "I mean what if
you get stopped you've already had one beer and you're covered in
another one. One whiff and a cop would bust you for driving under the
influence. Besides what would your mother think of me once she smells
beer all over you."
He was right of cause. My mother wouldn't understand about the beer and
why I was drinking it. Besides that I can't afford to get stopped. But
what else could I do.
Stan came up with a plan that seemed to work. "I could wash your clothes
and when they're dried you can put them back on. I'm sure I could find
something you could wear while they're washing. You could take a shower
in my room while I find you something and put your clothes in the
washer." Stan told me.
Seeing I really had no other recourse I followed Stan up to his bedroom.
It was a nice room with dark rich furniture. He had a king-size bed and
two dressers. There was another TV in his bedroom, even though it was a
projection screen TV it wasn't as big as the one down stairs.
His bathroom was quite large with a large shower and a large whirl pool
tub. The counters were tiled, as was the floor. There were mirrors on
each wall and all the fixtures looked like they were made of gold.
As Stan started to close the door to the bathroom he said, "Take off
your clothes and hand them out the door then get in the shower. I'll put
your clothes in the washer and find you something to wear."
It didn't take me long to shed my wet clothes and hand them out to Stan.
It also didn't take me long to shower but Stan was back in the bathroom
before I was done. Through the door of the shower I heard him say. "I
left you something on the counter. It's not much but it's the only thing
I have that will fit you. All my clothes will fall right off you."
Once I heard the door close again I stepped out of the shower. I looked
around for the clothes he left me and saw what looked like a black silk
robe sitting on the counter. It looked a lot like the one Stan was
wearing.
Once I dried off I picked up the robe and found a pair of black satin
underpants under it. I quickly put on the underpants but I thought I had
put them on backwards, as there wasn't an opening in the front. After I
check the back of the underpants I saw it didn't have an opening either.
That's when I noticed that the waistband as well as the leg openings had
a small band of lace. I knew then that the underpants I was wearing was
really a girl's pair of panties.
My mind spun with what was happening. I couldn't figure out what to do.
Surly I couldn't let Stan see me wearing girl's panties. I mean what
would he think of me. But then I realized he must have known what they
were. He did bring them to me so he should known.
With no other option left open to me I put the panties and the robe on
and I open the door to the bathroom. As I did so I could feel my face
heat up with embarrassment. I had a feeling that Stan was going to laugh
at me for wearing girl's panties.
Stan took one look at my face and said, "Sorry Scott they're all I had
that could fit you. If I gave you a pair of my boxers they would have
fallen off you and that would be more embarrassing." Seeing he was sorry
made me feel better about my predicament.
Stan and I went back down to his living room to watch the movie. Before
he started it he got us two more beers and promised not to spill this
one on me. I chuckled as he sat next to me on the couch and we started
watching the movie.
The movie we were watching had a lot of girl on girl sex in it. There
were two guys in the movie that fucked a girl or two but mostly the
movie was about what the girls did to each other. From the minute the
movie started my dick became hard and stayed that way through out the
movie.
Obviously the movie must have gotten Stan excited as well. As he held
his beer in his left hand his right hand would move down and squeeze his
cock every once and a while. I'm not sure why I noticed this, but I
couldn't help watching him, as he squeezed it.
I also realized that Stan's dick was a lot bigger than mine was. Mine is
only four inches long and about the size of a quarter thick. Stan's
looked like it was twice as long and three times as thick.
I think the beer had something to do with my wandering eyes. After
getting doused with my second glass and the shower after I had lost the
fuzzy feeling in my head. But now that I had a second beer in me that
fuzzy feeling came back quickly.
When the movie ended Stan replaced the movie with another one before
going into the kitchen for more beer. As he walked around the living
room I could see his erection pushing out the front of his pants.
My own erection was pushing out the front of the panties I was wearing
but in my sitting position it wasn't as obvious. I could also feel a wet
spot formed on the panties right where the head of my dick was. I was
thankful I had the robe on as it covered my excitement.
When Stan sat back down next to me the movie had already started. On the
screen we watched a guy and a girl kissing passionately and I could see
their tongues going into each other's mouth.
We watched that for a few seconds before Stan asked, "Scott have you
ever kissed a girl like that or been kissed like that."
I knew the beer was working on me when I chuckled. It sounded more like
a giggle when I said, "No I haven't been that lucky yet. Every girl I've
ever met wanted to be my friend but not my girlfriend."
"Well don't feel bad, most girls want one thing. As soon as they get it
they want to change it. But god loves them, because I sure do. There's
nothing like having a cute girl in your arms while your kissing them."
We watched the movie for another thirty minutes or so. This had almost
all guy girl sex in it. I watched girls suck on really big cocks and I
watched the same girls getting fucked by these well-endowed men. It was
quite exciting to watch and I couldn't help reaching down and give
myself a squeeze.
Stan was squeezing himself more and more and once he saw me do it he
said, "You know Scott if you want you can take out your dick and
masturbate I won't mind."
I chuckled nervously and said, "I couldn't do that I would be too
embarrassed."
Stan laughed before saying, "I'll tell you what I'll pull mine out and
you can pull out yours. This way there's nothing to be embarrassed
about." Stan didn't wait for me to agree he popped the snap on his
pajamas reached inside and pulled out his cock.
I knew Stan's cock was big but until he pulled it out I had no idea how
big. He made mine look like a needle, as his seemed to reach half way up
to the ceiling.
After I stared at his cock for a minute or so Stan said, "Come on Scott
it's your turn now."
With out even thinking about it and with out taking my eyes off Stan's
cock I pushed the panties I was wearing down and pulled out my much
smaller dick. I watched as Stan's hand moved up and down the length of
his cock and I stroked my smaller one to the same beat.
How long I sat there starring at him I don't know but I was finally
heard Stan say, "You know you can touch it if you like. I like having
some one else's hand on my cock. It feels better than doing it by
yourself."
I was quite embarrassed that I was caught staring at his manhood but
Stan didn't seem to mind. He just put his left arm around my shoulder
and pulled me closer. His right hand came off his cock and it reached
over and took my right hand off my dick. He then wrapped my hand around
his cock.
In my mind I was telling myself that I should stop this but I couldn't
get my body to cooperate. My hand simply started to move up and down
Stan's cock as if it had a mind of it's own. At the same time Stan's
left arm had moved down and encircled my waist. The next second his left
hand was stroking my dick.
Just the mere touch of someone else's hand on my dick was too much for
me. I instantly felt my orgasm start to build but Stan wasn't ready for
that to happen. Stan pinched down on the base of my dick and my orgasm
subsided. Once I had calmed down his fingers started moving once more.
My hand never stopped its up and down strokes.
Stan kept me on the edge of orgasm for a long time. Each time I thought
he was going to let me cum he would pinch down on my dick till I calmed
down once more. It was agony, but a sweet agony. Each time I was close
to cuming my hand would move faster on Stan's cock but he would slow my
hand and tell me to make the pleasure last.
How long this lasted I don't know but when the movie ended Stan stopped
it and turn toward me. He cupped the back of my head in his hand and
pulled my head closer to his. Even before he kissed me I knew that's
just what he was going to do.
Even though my mind was screaming for me to stop this, my left hand
moved up and encircled Stan's neck. When our lips touched for the first
time I felt a small spark jump between us. It was like there was magic
in his kiss. When his tongue entered my mouth I licked it with my own.
Stan saw I wasn't about to stop him so his left arm came away from my
waist and it pushed my shoulder so we were closer. His right hand moved
down and an instant later the satin panties covered my dick once more.
Stan right hand then cupped my balls as his thumb started to massage the
underside of my dick through the satin panties.
My orgasm came over me quickly and this time Stan didn't try to stop it.
I saw sparks before my eyes at the same time it felt like my dick
exploded. I pulled my mouth from Stan's and gasped a loud moan as my
dick filled my panties with cum.
A moment or two later I felt Stan's body become rigid as he groaned out
an "oh god". The next instant I felt his cock become larger as my leg
was hit by something very hot and wet. Once our orgasms abated our lips
met once more and we kissed for several minutes.
After a few minutes Stan pulled his lips from mine and looked down at my
leg before saying, "It looks like I spilled on you again. Let me take
you up upstairs and clean you up."
My mind screamed for me once more to stop this but Stan didn't give me a
chance to stop him. He slid his right hand under my legs and his left
held my back. He then stood and picked me up and carried me to his
bedroom. All I did was wrap my arms around his head and held on.
Once in his bathroom Stan placed me on my feet and helped me remove my
robe. He then started the shower before he went to his knees in front of
me and pulled the panties off. He helped me in the shower and a moment
later he was naked as he joined me.
I'm not sure but this didn't seem to bother me. In fact it felt good
having him scrub my body clean with a washcloth. He made sure to scrub
every part of my body from my face to my toes, from my dick to my
asshole. When he was done I did the same to him even his most intimate
spots.
When we were finished in the shower he dried me off then took me into
the bedroom. I stood naked while he went to a dresser and pulled out a
baby doll nightie and help me put it on. As he was pulling up the
panties I told him I really should be going home.
Stan stood and said, "No you'll sleep here tonight. You've had too much
to drink and your too tired. I'll talk to your mother in the morning and
I'll explain you fell asleep watching a movie and I thought it best to
just leave you on the couch. Now hop into bed while I get some clothes
on."
As I got into bed Stan put on a clean pair of boxers before siding into
bed next to me. If I had any trepidation about sleeping in the same bed
as Stan it evaporated the instant his lips touched mine. We kissed for a
few minutes before Stan placed my head on his chest and I fell asleep
instantly.
When the intimacies of the night before hits the cold light of day your
perspective changes. What was good and natural becomes wrong and
immoral.
When I awoke in Stan's bed for the first time I was over come with
guilt. I felt guilty for enjoying the things Stan and I did the night
before. I also felt guilty for the wanting to do them again. I knew I
couldn't do those things with Stan any longer. It wasn't right, two men
aren't supposes to do those sort of things together.
Thankfully I didn't have to face Stan when I first woke up. By the time
I open my eyes he was gone. At the foot of the bed I had shared with
Stan I found my own clothes. And though I had enjoyed the satins I had
worn I was relieved to put on my own clothes once more.
Just as I had finish dressing Stan came into the bedroom. He had a sad
look on his face as he said, "I was just coming to wake you. Breakfast
is ready."
Just looking at him I was over come with guilt. I couldn't look him in
the eye when I said, "I should be going. I know my mother must be
worried about me." Another thing to feel guilty about.
Stan came over to me and placed his hand on my shoulder and said, "I've
already talked to your mother. She understands you were too tired to
drive home and you slept on my sofa. Before you go I think we should
talk, in fact I know we should. Now come along before breakfast gets
cold.
I followed Stan down stairs and sat down to breakfast with him. We sat
and ate together and for awhile neither of us said anything. Just when I
thought he was going to remain quiet for the entire meal Stan said, "I
hope you know I enjoyed our time together last night. I would like it if
you came back again tonight after you're done with work."
Stan was silent after that and I know he was waiting for me to say
something. I didn't want to hurt his feelings so I said, "I enjoyed it
too but I'm afraid what other people would say if they found out."
"First of all, no one is going to find out anything unless we tell
them," Stan told me. "I am not going to tell anyone. What goes on behind
these doors stays here. Also we didn't do anything wrong at least not in
my eyes. You were acting the girl's part and I was acting the boy's part
it was like a play."
I knew that was pretty lame reasoning, but I could see where he was
coming from. After all I was dressed up like a girl in the panties and
the robe. Even the nightie I wore to bed bespoke of the female gender.
But I couldn't deny I liked what we did and I would like to do it again.
I mean he showed me so much attention, more than any one else ever did.
I just couldn't come out and say it.
I'm not sure if Stan understood this but his next sentence seemed to say
he did. As he stood up he said, "Scott if you want to come back I'll be
here waiting. Your restaurant closes at ten so I figure you can be here
by eleven. If you're not here by midnight then I'll know your not
coming."
"What should I tell my mother?" I asked.
"Well Scott it's time to be an adult. Tell your mother your coming over
here and you may be home late. It's time to cut the apron strings." Stan
told me as he showed me to the door.
I knew Stan was right about my mother, but was he right about
everything. I was after all a man even though I had worn panties the
night before. My mind was telling me what we did was wrong but my body
kept giving me a hard on every time I thought about the pervious night.
When I got to the restaurant my mother asked me about my application and
what Stan thought of my chances of getting in. She didn't even mention
the fact that I had stayed out all night. I told her about the
application, she told me to go to work as if I hadn't stayed out all
night.
All day my mind went back to the night before. Several times I was so
caught up in my daydream that a customer had to tap me on the shoulder
to get my attention. It was probably around six that night when I
convinced myself I would be going back to Stan's. I knew I couldn't stay
away.
It was my mother who gave me the opening I needed to tell her I would be
going over to Stan's that night. About nine thirty she came up to me and
said, "Mr. Franklin want's to know if we could still deliver a pizza
tonight. I've already let the other boys go home. Do you want to deliver
it, if not I'll tell him we can't?"
I wondered briefly if Stan was giving me a reason to come over. Then I
though he had no idea who would be delivering his order. After I thought
it over I said, "Tell him we'll get it there. I'll take it and I may
spend a few hours with him."
My mother smiled and said, "Okay honey if you do come home late be
careful driving. If you don't think you can drive stay the night like
last night."
A half-hour later I was on my way to Stan's this time I didn't bother
stopping at home as I had a suspicion that I would be once more in
panties and a robe. I figured I could shower before I changed.
When I arrived at his door Stan looked surprised it was me who was
delivering his pizza. I also saw he was once more wearing the black
pajama pants and the silk robe from the night before. When he looked for
the bill I told him, "My Mom said this one was on the house because you
are a good customer."
"Well tell her thank you but I still owe you a tip for driving it out
here." Stan told me as he picked up his wallet off the hall table.
I waved him off and said, "That's okay I was coming out here anyway."
The look on his face told him I surprised him.
He recovered quickly by saying, "Would you like to change so I don't
spill anything on you."
This was a problem that bothering me all day. For some reason Stan
wanted me to wear girl's clothes. I didn't mind it but I wanted to know
why. So I said, "I will if you want me to but why do you want me to? Are
you gay?"
Stan chuckled and said, "No I'm not gay but I'm not straight either. I'm
bisexual. I like girls, but I really like boys that look like girls. I
like knowing they have something under their skirts they shouldn't
have."
This was something I never heard of. I've heard about gays and lesbians
but I never heard about guys that like boys that dress like girls. So I
had to ask, "So when I put on those panties yesterday I looked like a
girl to you?"
Stan knew I was catching on to his game so he said, "Well you have
feminine qualities but you needed some make up and a few other things. I
would have to say, I think after some practice you could make a
wonderful girl if you want."
I thought this over. I liked Stan a lot and he was being pretty nice to
me. I also knew I didn't have much hope of attracting a girlfriend with
my small statue. So I figured I give this a shot and see how it works
out. I mean the sex we had the day before was pretty good and it could
only get better. I just wasn't sure what I would be expected to do. I
was still pretty naïve when it came to sex.
After thinking this over I looked up at Stan and said, "Do you have
something you would like me to wear. I'd like to give this a try."
The smile on Stan's face couldn't have been brighter. He took my hand
and led me up the stairs and into his bedroom. As we entered I saw there
was a pair of red panties and a red satin robe on the bed. This told me
he had hoped I would come.
Instead of telling me to put those on he walked over to the dresser that
he had taken the nightie from the night before and started going through
the draws. He first pulled out a pair of stockings then what I would
later find out was called a chemise. He also pulled out a pair of
panties that matched the white chemise and a white garter belt. He also
pulled out a pair of white high heels from the closed.
As he stood in front of the open closet he said, "There a few things in
here you could wear on top of you outfit. Why don't you look them over
and decide on something.
I walked over to the closet and looked inside. There were several
dresses as well as several robes and long nightgowns. There were also
quite a few pairs of high-heeled shoes at the bottom of the closet.
There were sweaters, blouses and skirts, but not a single pair of
women's pants.
After looking over the array of women's clothes I asked, "I gather I'm
not the first boy you've had here. Do you fine boys willing to do this
often?"
Stan chuckled and said, "Not often enough but I have entertained a few
sissy boys, no one locally until you. They usually came here with me
from the city."
"In that case do you have any makeup I could use?" I asked.
Stan looked surprised as he asked, "Do you know how to but it on?"
I smiled and said, "I've been in a few plays and I had to wear make up
on stage, but I didn't have to make myself look like a girl. I've also
watched my mother put on her makeup quite often as a child. I'll give it
a try but I can't make any promises on how good I'll look."
Stan walked over to what looked like a writing desk. He lifted the
center and flipped up a mirror. In the space under the mirror was an
array of cosmetics. He then said, "In the draws you will find more, but
don't over do it. I want a pretty girl not a street whore."
"I'll try my best now if you would give me some privacy I'll try an turn
myself into a pretty girl for you," I told him. I was hoping that Stan
would kiss me but instead he went toward the door and left the bedroom.
Once Stan was gone I took a quick shower. When I was dry I sat at the
makeup table and looked over the cosmetics. I really didn't know where
to start, as every thing looked so foreign to me. In the end I decided
to start on my eyes, as it was where my mother always seem to start.
I picked up the mascara first and looked it over. I wasn't sure how to
start but when I though of my mother my hands seem to know what to do.
After almost poking myself in the eye I was able to get the brush on my
eyelashes. I didn't put on too much, as it seemed like I didn't have on
enough. When my eyelashes were slightly blacken I stopped and thought it
was enough.
I didn't try putting on eyeliner, as I was sure to mess it up. I then
used a light brown eye shadow to darken my eyelids. I put a little blush
on my cheeks then used a deep red lipstick on my lips.
When I was done with the makeup I looked my face over. How feminine my
face looked surprised me. I mean my face looked like any girls at
school, though I wore less makeup than most of the girls at school wore.
As far as my head went I looked like a girl except for my hair.
My hair was another problem. It wasn't that long as I had just gotten a
hair cut, and no matter what I tried to do with it, it still took on the
shape of a boy's haircut. In the end I mousse it down and tried to fluff
it up. After giving up on my hair I sprayed myself with a little perfume
before moving over to the bed to get dressed.
I took the panties first, but when I went to put them on I noticed that
they didn't have a back to them. There was a thin strip of satin cloth
that connected the triangular piece that would cover my dick and balls
to the waistband in back. When I slid these on I realized that the strip
of cloth was suppose to go between my butt cheeks. This really felt
quite odd as the strip settled between my cheeks.
I next put on the stockings. I knew how to put these on as I had watched
my mother put on pantyhose hundreds of times in the past, well until I
was about eight anyway. Stockings were actually easier as I only had to
worry about one leg at a time. I wasn't really happy with them as they
pulled on the hair of my legs and once they were on all the way the
hairs made my legs itch. I guess that was why girls shaved their legs
all the time.
Once I had the stockings on I turned my attention to the garter belt. I
had seen girls wearing these before on TV, but I never saw anyone put
one on before. I couldn't even tell the front from the back. Getting it
on was easy enough as it had a clasp like a bra but was it suppose to go
in front or in back.
I finally decided that the clasp was suppose to go in back as there was
a tiny pink bow that was centered on the opposite side. I figured the
bow should go in front. Next came the garter straps. At first they were
too long and it took me some time to figure out how to shorten them. It
also took me some time to figure how to attach the garters to the
stockings.
By the time I got the garters attached to the stockings and they were
tight enough to pull on the stocking I had broken out in a sweat. Before
putting on the chemise I went to the bathroom and wiped off with the
towel I had used earlier. I them put on the white chemise and went to
the closet to find a top.
There were a few dresses I was sure would fit me, but I knew it was
late. I couldn't see wearing one of those at this hour. For the same
reason I didn't look at any of the skirts or sweaters. Instead I chose a
white satin robe that seem to match what I was already wearing. Seeing
the panties and the chemise was satin the robe seem to be perfect.
I had save the heels for last for a reason. First of all I knew they
wouldn't be easy to walk in and I wanted to get dressed before I tried
them. They weren't really high, as the heel was only two and a half
inches tall. They had straps that crisscrossed over my instep and a
strap that went around my ankle.
When I got both shoes on I stood for the first time. I was surprised
that my balance was thrown off and I nearly fell over before I took a
step. Once I got my balance right I took a step. This was hard too as I
almost lost my balance again and fell over. Each step after that made me
feel like I was going to twist my ankle. I had to walk around the room
several times before I could get use to them. I wound up taking tiny
steps and mostly walked on the balls of my feet.
Once I could walk with out tripping I went over to a full-length mirror
and looked myself over. My legs looked rather nice in the stockings
though I could see the hairs on my legs. They actually looked like
girl's legs. Seeing the rest of my body was covered in white satin I
looked like a flat chested girl. The only thing that didn't look
feminine was the way my dick pushed out the front of the panties.
I had also noticed I had licked off the lipstick I had put on earlier. I
went over to the makeup table and re-coated my lips. When I was done I
went to put the lipstick back on the makeup table. Instead I dropped the
tube into the pocket of my robe. I then went looking for Stan.
I only had to walk down stair, which was not an easy task to find Stan.
He must have heard me walking down the stairs as he came out of the
dinning room just as I landed on the first floor. The smile on Stan's
face made all the work I had gone though worth it. He also had a hungry
look in his eyes, as he looked me over. For some reason I couldn't
explain that look made me feel special.
Stan took my hand in his and said, "God you're really beautiful dressed
like that."
I felt myself blush before asking. "Do you really think so? I know my
makeup could be better."
"With practice you could pass anywhere as a real girl." Stan told me
before he gentle pulled my hand so I would follow him.
Stan guided me into the dinning room and asked me to sit. He then pulled
a chair over so he could sit directly in front of me. He took my hands
in his and asked, "How does it feel to wear girl's clothes?"
It only took me a second before I said, "I like it. I like how they feel
though I don't care for how the stockings feel right now. If I get a
chance to do this again I think I'd like to shave my legs first."
Stan lifted my hands to his face and kissed my hands before saying, "I'm
glad to hear you say that. I'm also glad you want to do it again. I
don't think I could look at you again as a male and not see the girl
that sits in front of me. You will always be a girl in my mind."
I don't know why but what Stan just told me didn't bother me. I didn't
mind that he would always think of me as a girl. With out thinking I
said, "I always want to be a girl for you."
By the look in Stan's eyes I could have sworn he was going to kiss me
but instead he said, "You do realize what we're doing has nothing to do
with me helping you with college. I mean I would help you get into NYU
with out what we're doing together. I just don't want you thinking I'm
using you."
That thought never occurred to me and I told Stan as much. He then
pulled me onto his lap and we kissed. It was the sweetest kiss we shared
to that point and it was one I would remember always.
When Stan stopped kissing me I said, "I'm not sure what you expect from
me, sexually speaking. I've never been with anyone before and you may
have to teach me."
Stan kissed my cheek before saying, "I'll teach you everything you need
to know on how to please a man. If that's what you really want. That
means I don't want you saying we shouldn't be doing this to each other.
I want a she-boy that wants to be a she-boy. Not a boy who only acts
like a girl when it come to sex, I want you to be a girl all the time
around me."
I wasn't sure I wanted to be a girl all the time but I also knew I
wanted to give it a try. I want to see how far we could take this. I
knew my life, as a boy wasn't the best. I hated getting picked on by
bigger boys in school and I hated the way girls treated me. They always
treated me like a little brother. Mostly I hated being ignored by just
about every one.
It didn't take me long to think this through and I said, "I want you to
teach me how to be a she-boy. I want to be a she-boy for you."
Stan kissed me again though this time it was hard like he was over come
with passion. This time his hand moved up and covered my flat breast. A
few seconds later I felt his thumb and forefinger start to play with my
male nipple. I was shock by how sensitive my nipple was. I couldn't stop
the moan >from escaping my throat.
We kissed passionately for several minutes then Stan stood me up and
said, "Come on my beautiful sissy boy I want to show you a tape of what
sissy's do for their lovers."
Stan took me by the hand and walked me into the living room where the
big screen TV was. As he started looking through tapes he said, "Why
don't you go into the kitchen and get me a beer and a glass of wine for
yourself. Girls shouldn't drink too much beer, as it's bad for your
figure." As I went into the kitchen I could feel Stan's eyes follow me
every step of the way. I liked knowing he was watching.
I knew quite a bit about wines and when each should be drunk. I knew
that a nice Merlot was good this late at night and it was rather low in
calories, compared to other wines. After pouring myself a glass I opened
a bottle of beer and went back into the living room.
When I got back into the living room Stan was standing by the sofa
waiting for me. While I was gone he had taken off his robe but left the
pajama pants on. He took the wineglass and the bottle of beer from me
and placed them on the coffee table. He then took me in his arms and
kissed me. Sometime during the kiss he removed my robe, but I really
don't remember it.
We then sat on the sofa. Stan sat in the corner with me right along side
him. There was no pretence that we were just going to watch the movie.
Stan pulled me close and kept his arm around me as if he was afraid to
lose me.
When the movie started there was a man and a woman on the screen. They
were in the middle of a kiss when the action started. It didn't take
long for the girl to drop to her knees and after unbuckling the man's
pants she started sucking his cock.
The man wasn't hard when she started but in a few minutes his cock
started to grow. The girl was quite good at giving head, as she didn't
seem the least bit bothered by the man's huge cock. If I had to guess I
would have to say he was at least as big as Stan was.
I wasn't sure why we were watching this movie, as it reminded me of one
we watched the day before. That was until the girl got off her knees and
the guy went to his. As he pulled off the skirt she was wearing I saw
there was something odd with her panties. As the guy pulled off her
panties I realized what made them look so odd. The girl had a cock where
she should have had a pussy.
She looked just like a girl. She had long brown hair and full breasts
just like a girl. The only difference was the cock and balls that hung
from her pelvis. Even her legs looked like a real girl.
As the guy in the movie started to suck the girl's cock Stan whispered
in my ear. "Honey take out my cock and play with it. I don't want to cum
but I like feeling your sweet little hand on my cock."
I'm not even sure I though about doing it before my hand reached over
and undid the snap on his pajamas. I then reached inside and grasped his
manhood in my hand. Stan was already hard and it took a little
persuasion to get it out of his pajamas. At the same time I couldn't
take my eyes off the TV.
As I slowly stroked Stan's cock I continued to watch as the guy sucked
the girl's cock till it was as hard as his was. Once her cock was hard
the guy turned the girl around and started kissing her bottom.
It was then that Stan whispered, "Honey pull your feet onto the sofa so
I can play with your sweet ass. I've thought about that beautiful ass
for weeks now."
I couldn't understand why Stan wanted to play with my ass. I mean we all
know what comes out of there, but I wasn't going to deny him anything at
this point. I pulled my legs up so I was practically lying on the sofa.
Stan reached behind me and started massaging my cheeks. At the same time
Stan leaned over and kissed my head.
Even though I couldn't understand why anyone would want to touch my
backside it didn't stop me from feeling the pleasure of his caress. I
mean it felt odd but good to have his hand on my bottom. But what made
me moan was when he slid his finger along the crack of my ass.
I continued to stroke Stan's cock as a moaned escaped my lips each time
his finger went up and down my crack. I could barely concentrate on the
movie, as I wanted to close my eyes and relish in the pleasure of Stan's
finger. But I really wanted to see what the two on the screen were going
to do next.
I watched the guy lick the girl's cheeks before he started licking the
crack. I really couldn't imagine any one doing what he was doing. What
really shocked me was when I saw the guy lick her asshole. I mean I
could see him run his tongue around the hole like it was a pussy.
At the same time Stan reached over to the end table next to him and
picked up a bottle. On the label I saw the words super lube as it passed
my head. A second or two later I felt Stan pull the strip of cloth from
between my ass cheeks and then I felt something dripping on my ass hole.
As I watched the guy stick his tongue up the girls ass hole I felt Stan
push a finger up mine. At first there was a bit of pain but that quickly
vanished as a moan escaped my lips. I was surprised by how good his
finger felt as it slid inside me.
Stan started fucking me with his finger and it was like nothing I ever
felt before. I couldn't stop the moans and groans from coming out of my
mouth, not that I thought about stopping them. I even rolled over to
give Stan easier access to my ass. This brought Stan's cock only inches
from my face.
His cock looked so big and yet so beautiful this close and there was
clear fluid leaking out the tip. I couldn't stop my self as I leaned
over and kissed his beautiful head. My lips touched that clear fluid and
my tongue quickly licked it off my lips.
There was very little taste to the fluid though it was slick as oil. It
had a manly taste though not unpleasant and I leaned over and kissed his
cock once more. This time I made sure to get plenty of the fluid on my
lips and again I licked my lips to taste the fluid. After smacking my
lips I started licking the head of Stan's cock.
I heard Stan moan before he said, "That's it honey lick my cock but keep
you eye on the TV."
I had to force myself to look at the TV as my tongue moved all over the
head of Stan's cock. On the screen I watched as the guy who was now
standing eased his cock between the girl's ass cheeks. A close up shot
showed how the head of the guy's cock penetrated the girl's ass hole.
The girl moaned deeply as she begged the guy to fuck her pussy. It was
the first words I heard on the movie.
At the same time I felt Stan slide a second finger into my ass. At first
it felt tight. I really didn't care, as the only thing I cared about was
what I was doing to Stan's cock and the pleasure of his fingers in my
asshole. When Stan saw I was enjoying his finger fucking he added a
third finger.
At the same time I took the head of Stan's cock in my mouth for the
first time. I didn't go too deep like they did in the movie, but it seem
to please Stan as I heard him moan and I felt his cock lurch.
His cock felt good in my mouth as I sealed my lips around the head. I
sucked slightly and I felt some more of the clear fluid leave Stan's
cock. I tried moving down his shaft like they did in the movie but his
cock quickly filled my mouth.
By this time I had forgotten all about the movie as I tried to suck my
first cock. I could hear the girl asking to be fucked harder and I could
hear grunts and groans coming from the TV, but I didn't care by this
point. I only want to suck Stan's cock as he continued to finger fuck my
ass.
After a few minutes I felt Stan's hand on mine as he forced me to stroke
his cock. Once I had the rhythm he wanted I felt his hand move to my
head. His other hand never left my ass, as his fingers seem to go in
deeper. I can't tell you how great this felt as I sucked my first cock
and had my ass fucked at the same time.
My mouth soon grew used to the thickness of Stan's cock and soon my lips
were moving further down his shaft. It didn't take long before I could
feel the head of his shaft touch the back of my throat and my lips slid
easily up and down his shaft. I felt Stan's hand on my head as if he was
guiding me in my first blowjob but he never forced me to go deeper than
I wanted.
At the same time I started humping the sofa as Stan continued to finger
fuck me. I was beside myself with pleasure and I wanted to cum with
Stan's fingers in me but I also wanted Stan to cum too. I wanted to make
him cum.
I didn't have long to wait as I heard Stan say in a gasp. "Oh god girl
I'm going to cum. I'm going to fill your mouth with cum any second." I
wasn't sure if this was a warning or a statement but I wasn't about to
stop.
A few seconds later I felt Stan become rigid and his cock became harder.
A moment later I received my first load of man cum. It squirted out of
his cock like a bullet out of a gun. It instantly filled my mouth and
some squirted out the sides of my lips. I tried to swallow knowing guys
loved it when the girl swallows. I couldn't even tell you what it tasted
like except it was thick like egg yokes and hot like melted butter.
I didn't have time to taste it fore as soon as I swallowed the first
load the second one was filling my mouth. How many times he squired his
love juice in my mouth I couldn't tell you as it was all I could do to
keep it >from escaping my lips.
It wasn't until he was drained that I could taste it. It was slightly
bitter like a dark beer and slightly salty like beer. There was a slight
metal taste to it though that didn't bother me. I actually found I like
the taste and I knew this wouldn't be the last load of man cum I would
drink.
I continued to suck until Stan pulled my head off his over sensitive
cock. Once my lips were free of his shriveling cock I saw there was some
of his cum that had escaped my lips. I licked up all I could find and
swallowed it down like it was manna from heaven.
Once Stan's cock had shriveled into softness and I had cleaned up any
cum I missed I realized I didn't get to cum with him. I was too
preoccupied in my endeavor to bring my lover off. I also realized that
the movie we were watching had ended and the TV screen was nothing but
snow. I took the remote and turned off the TV then rested my head on my
lover's tummy till he recovered from his orgasm.
It only took a few minutes till I felt Stan stroke my head like he was
petting a dog. I then heard him say, "You surprised me girl. I didn't
think you would suck me off the first night."
"I'm sorry should I have waited until you told me too?" I asked even
though I knew the answer.
Stan chuckled and said, "No you did just fine. Most first timers have to
be talked in to sucking cock. The way you seem to take to it naturally
tells me you really enjoyed doing it."
"I did enjoy it Stan. As soon as you're ready I'll do it again. I
especial like doing it with your fingers in my backside," I told him
before I kissed his cock once more.
Stan turned me over so he could look at my face before he said, "I think
you could be just the girl I'm looking for." With that said he kissed me
deeply.
When we ended our kiss I asked, "What do you mean just the girl your
looking for?"
Stan caressed my side as he said, "I'm looking for a boy who is sweet
and feminine and likes being a tranny. Most of my lovers don't want to
go that far, They like dressing up but after they get out of bed they
want to be boys again. I'm looking for a she-boy that wants to be a
transsexual like the girl in the movie."
I didn't say anything, as I wasn't sure I wanted to go that far. It was
fun dressing up for Stan and I know I would anytime he asked me too. I
also knew I liked sucking his cock and I loved having his finger up my
ass, but I wasn't sure I wanted to be a girl all the time. If I had
breasts then I would have to dress like a girl all the time. Besides how
do you get breasts anyway?
Stan must have understood my trepidation as he said, "Come on honey
let's go up to the bedroom so I can return some of the pleasure you gave
me."
I stood up to let Stan up and as I did so I bent over to pick up the
robe that I had worn earlier. As I did so I felt Stan's hands on my
bottom and then I felt his lips on my cheeks. I knew then that he was
going to fuck me when we got upstairs.
I shivered from the thought of his big cock going into me. Stan must
have known what was going through my mind. Stan stood up and hugged me
to him before saying, "Relax honey I'm not going to take you tonight.
The first time I make love to you that way I want it to be special. I
want you to want it as much as I want it. I don't want you experiencing
any pain with our lovemaking. I want you to remember it as a wonderful
and loving experience." That really made me feel better.
I turned in Stan's arms and kissed him. We then went upstairs to the
bedroom. Once inside Stan took off his pants and lay on the bed. I went
around to the other side and as I passed the makeup table I took a quick
look at my face. I saw that the lipstick I had put on was now completely
gone.
It took the tube from my pocket and reapplied it to my lips. As I did so
I heard Stan chuckle. When I asked his what was so funny he said,
"Nothing sweetie. You just did what any self-respecting women would do.
Now come here." I slipped off my robe and lay on the bed in Stan's arms.
I don't know why I bothered putting on the lipstick seeing Stan had
kissed it all off. We kissed for a long time before Stan moved down to
my neck. He kissed and licked my neck before taking off my chemise. He
then licked and sucked on my chest and even on my tiny nipples. I really
enjoyed it when he sucked on my nipples. It made me want to have big
breasts for him to suck on.
He then moved down to my tummy, he licked and kissed it before moving
down to my pelvis. At first I thought he was going to remove my panties
but he just pulled them down and licked all around my dick. I was still
quite hard, as I had been most of the night. I really didn't think he
would suck my dick but Stan surprised me by taking my dick into his
mouth.
This was the first time I ever had any one do this and the feeling of
his warm wet mouth was too much for me. I barely told him I was going to
cum when I started squirting my sperm into his mouth. Stan didn't miss a
beat as he sucked down all my juices and sucked on my dick for more.
Seeing I just came I thought Stan would stop but he continued to suck me
for another few minutes. I thought I would shrivel to nothingness but
Stan kept my dick hard. Once he knew I wouldn't go soft he moved lower
and started licking my balls. He lavished my balls for a few minutes
before he turned me over on to my tummy.
Stan licked and kissed the cheeks of my bottom till I thought he had
touched ever inch of skin back there. He then started to lick the crack
of my ass. I never knew anything could be so wonderful. Stan's tongue
slipped into my crack and he moved up and down. Each time he changed
directions he went a little deeper. I'm sure Stan knew the pleasure he
was giving me as I whimpered on every pass.
When I felt the strip of cloth being pulled from between my cheeks I
knew Stan was going to lick my hole like the guy in the movie did. At
first I was worried I wasn't clean enough back there, but the second his
tongue touched my hole I didn't care any longer.
Stan licked my hole for several minutes then I felt his tongue push at
my hole as if he was trying to push it in me. That was what Stan was
trying to do. As his tongue penetrated me the first time I squealed like
a girl. It was amazing and stars popped before my eyes. I honestly felt
like I was going to cum again.
Stan tongue fucked my hole for a long time till his tongue grew tired
and he had to stop. He then straddled my legs and his cock rested
between my cheeks. To tell the truth if he wanted to push his cock into
me at that point I wouldn't have stopped him.
Stan merely humped my ass as he reached into the nightstand. He pulled
out a transparent blue bottle and what looked like a small cock. He then
moved back down and I felt cool liquid being poured on to my asshole.
Once he worked the lubricant into my hole I felt something blunt at the
entrance I though he had changed his mind about fucking me till I heard
him say. "Relax baby I'm going to use this dildo on you to so you know
what it feels like. I'm going to leave it in you so we can train your
pussy. This way when we're ready to make love for the first time you'll
only feel the pleasure and not the pain."
I felt Stan work the dildo into me until I felt the head of it pass by
my opening. It hurt a little but Stan was very gentle. Once the head was
in I felt him push in a few more inches. He worked the dildo in and out
for a few minutes then I felt him push it in a little more.
I was surprised at how much I enjoyed the dildo. I thought it was a
shame it wasn't Stan's cock that was fucking me. But I also knew I could
never take Stan's cock I wasn't that big back there.
Stan worked the dildo in and out of me for several minutes. Ever few
minutes he would push more into me. Each time he pushed in more it felt
like it was getting wider. When he push in the lasted of it I felt like
I was open up a mile. When my hole closed around the base I thought he
had pushed it in too far until I felt the wide flange that was still out
side my hole.
Once he had it in me he patted my bottom and asked if I was all right.
"Yes," I said, "but I feel so full. Like I have to go to the bathroom."
Stan kissed the nape of my neck and said, "You'll get use to it. Believe
me this will help. Now turn over."
I flipped over onto my back and Stan got between my legs. He then lifted
my legs and put my feet over his shoulders. With his hard cock resting
on my smaller one he squeezed my thighs together with his cock between
them. He then started to thrust his cock between my thighs.
At first I wasn't sure what he was doing but once his cock started
rubbing against mine with only the thin satin panties between us I
didn't care. His cock moved back and forth rapidly and in no time I was
sinking into the blissful feeling of my impending orgasm. Stan wasn't
far behind, as he started grunting each time he pushed forward. A few
seconds later I was filling my panties once more. A moment or two later
I felt hot thick ropes of Stan's cum land on my chest and stomach.
Stan released my legs and they fell to his sides he then leaned over and
kiss me passionately. When our kiss ended he said, "It looks like I made
a mess of you again. Let's go hit the shower before bed."
As Stan went to turn on the shower I removed what clothes I was still
wearing, I then joined him in the shower where we kissed and hugged each
other till the water turned cold. We dried each other off before going
back into the bedroom. As Stan climbed into bed naked I went into the
closet and put on a long sheath type nightgown. Once I was in bed we
kissed then Stan placed my head on his chest where I fell asleep.
When I woke up the next morning Stan was in bed with me. He was nibbling
on my ear and I'm sure that's what woke me up. When he saw I was awake
he said, "Time to get up love. Breakfast is ready and we need to talk
before you leave. Now don't change and don't take out your butt plug
unless you have to go to the bathroom. If you do, I want you to put it
back in when you're done."
Stan kissed me then left the room. Thankfully I didn't have to go the
bathroom that way so I didn't need to take the butt plug out just yet.
After peeing I washed my face and hands then went back into the bedroom.
Just to let Stan know I was serious about being a girl for him I decided
to put on some makeup. Like the night before I put on mascara and blush
before coating my lips with a pale red lipstick. I then found some tan
fuzzy slippers in the closet that went well with the tan nightgown I was
wearing.
I went down to the kitchen where I found Stan sitting at the table. I'm
pretty sure he noticed that I had put on makeup as he smiled when he
looked at my face. As I sat down next to him he leaned over and gave me
a kiss on the cheek.
We ate breakfast together and when we were done Stan said, "Do you have
a name you like. A girl's name you would like to be called?"
I thought about it for a few minutes, I remember a girl I knew in
grammar school. Her name was Sara and she was the only girl that didn't
treat me like I was her kid brother.
I told this to Stan and he said, "From now on I'll call you Sara. Seeing
the way you're dressed I can't call you Scott any longer." I actually
blushed when he said this.
Stan then reached below the table and came up with a bag. It was a plain
brown bag like the ones you get at the grocery store. Stan placed the
bag in front of me and said, "I want you to take this home with you.
Inside you'll find several pairs of panties a new bottle of anal lube
and another butt plug. I want you to wear the panties as often as you
can with out getting into trouble. I don't want you wearing them when
there a chance you will be found out.
"As for the butt plug I want you to put it in as often as you can and
when you think you can handle it I want you to switch to the larger one.
This will prepare you for the first time I make love to you," Stan told
me as he slid the bag closer to me.
Stan then took a key out of his pocket and slid that over to me and
said. I'm going to be gone for two weeks. I would like it if you would
come by and check on things. While you're here I want you to dress as if
I was here and stay that way until you leave. You can do what ever you
like as long as you're dressed like a girl."
I don't remember ever feeling as sad as I did at that moment. Stan must
have seen the sadness in my eyes. He took my hand and said, "I'm sorry
honey but I made these plans before we became lovers. I would cancel
them and be here next week but I really can't. I do have a business to
run. I have to leave shortly as I have to get back to the city and pack.
Can you take care of the dishes if it's not a bother?" How could I
possibly say any thing but yes?"
Stan came over to me and kissed me deeply for a few minutes before he
left the house. I stood at the window as I watched him drive away. The
sadness I felt earlier became worse once his car was out of sight.
After I consoled myself for a few minutes I went back to the dinning
room and took the breakfast plates to the kitchen. After loading the
dishwasher I went upstairs to change. I made sure to put on panties
under my male clothes. I knew Stan would like that. Less than an hour
after Stan left I was locking the door before I went home.
As I drove home I knew my mother would be home when I got there. Sundays
and Mondays the restaurant was closed. My mother thought every one
should have a home cooked meal on Sunday. Sunday were also the day's
that my mother went over the books and now that there was online banking
she was able to pay her bills.
Sunday's were also the days I caught up on my studying. Thank fully this
semester I only had three courses and seeing it was the end of the year
I had very little studying to do. In fact there was just one final I had
to take seeing I was a straight A student. History was the only course I
had a final in.
As I walked into the house I heard my mother say from another room.
"Scott honey is that you?"
"Yea mom I'm going up to my room," I told her as I started climbing the
stairs.
Before I got half way up she was at the bottom of the stairs saying,
"Scott we need to talk. I know you don't like to talk about the
restaurant but I really need you to listen to me."
"Okay mom I'll be right down," I told her as I went up stairs to put the
bag that Stan gave me in my room.
My Mother knew I hated talking about the restaurant. In my father's will
he gave his half of the restaurant to me in case my mother married
someone else. This way I would always have part of it. My mother held my
half in trust until I was eighteen. And now that I was I had to sign off
on anything relating to the restaurant.
As far as I was concerned the restaurant was all hers and she could do
what she wanted with it. After all it was her business sense that kept
it going since my father's death, but my mother didn't see it that way.
She wanted me to be involved with it. It really didn't matter, as I
would agree to what she wanted.
After I put the bag away I went down to our home office where I knew my
mother would be. She was sitting in front of her computer going over the
bills when I walked in. She patted a chair next to her and told me to
sit down.
I was pretty sure I knew what this was all about as we had these meeting
each month. She would go over the books showing me how much we took in
and spent and our net profits for the month. I would always look over
the numbers. But I had very little input. I really wasn't interested.
After going over the records she said, "We had a really good month this
time, but that's not what I wanted to talk to you about. I was thinking
of selling the restaurant."
To say I was shocked was an understatement. I know my mother had offers
before. In fact she usually got two or three a year. Most she didn't
even bother to think about, as the terms were not to her liking. Most
buyers wanted her to carry a note where they would pay her off each
month for several years. My mother didn't like that. If the restaurant
went under she would be out quite a bit of cash.
"Are you serious?" I asked dumbstruck.
"Yes honey I'm seriously looking at the proposal. It's all in cash I
won't have to carry a note and it's a very generous offer," she told me
as she handed me a sheet of paper.
It was the offer to buy from the Chef who now works for my mother. This
told me he would most likely keep the menu as is seeing he knew all her
recipes. Our loyal customers probable would never noticed the ownership
changed.
I also saw it was a very good offer and most likely my mother wouldn't
have to worry about money for the rest of her life. I also knew she had
quite a bit of money in the bank and in stocks from the life insurance
from my father. He made sure we were well provided for before he died.
After looking over the offer I asked, "Can you tell me why you want to
do this?"
"It's simple honey," she told me. "First of all I'm forty four years
old. I've been running the restaurant for the last ten years by myself.
I think its time for me to sell and enjoy the years I have left. You're
going away to college in the fall and you won't be here for me to take
care of. As far as your college is concerned you have the trust fund to
pay for that and you'll receive an allowance each month to cover
expenses."
I knew all about my trust fund and I also had a pretty good bank account
that I could use if I need it. Money for me was not a problem and
neither was it for my mother. I just couldn't see my mother sitting at
home all the time.
"Once you do sell what are you going to do? I can't see you sitting at
home for long," I asked.
My mother laughed then said, "I can't see that either. I was thinking
about moving to Florida with your Aunt Cheryl. She's been after me to
moved down since her husband died."
My Aunt Cheryl was quite well off seeing her older husband was a doctor
and he left her a ton of money. But I also knew Cheryl was a flirt and
she always had quite a few men following her. "Are you sure about this I
mean Aunt Cheryl is rather um."
"My sister has a tendency to be a bit of a floozy. I know." My mother
said as if finishing my sentence. "Really she isn't like that at all.
She just likes the attention men pay her."
I couldn't see my mother fitting in to that crowd but she was my mother.
She was right though she did deserve some enjoyment in her life. "If you
want to sell then go ahead. I think you should enjoy yourself."
"I think its time we both enjoyed ourselves honey. I also wanted to say
I love you very much and I will support you in anything you do. No
matter what you do in this life I will be behind you one hundred
percent," my mother told me. I had a feeling she knew something and it
had nothing to do with the sale of the restaurant.
Except for saying thank you and telling her I love her too I had nothing
else to say. As I got up to leave the office she nonchalantly said
"Honey before you go to school tomorrow make sure you remove your
mascara."
I was dumbfounded. I couldn't say anything as I remembered I didn't wash
my face before getting changed to come home. I froze in place thinking
my mother was upset with me, but she came over and took me in her arms.
After she kissed my forehead she said, "Honey like I said before I'm
with you all the way. If you want to talk about it or you need any help
just ask."
"What do you mean," I asked even though I knew what she meant.
"Don't be silly honey." She said, "You got on mascara and I can see pink
lipstick on your lips but most of that has worn off. There's also
blusher on your cheeks. That tells me you are the female in your
relationship with Stan Franklin. I'll have to admit, if you're going to
date a man he is a prime stud. He makes me weak in the knees just
looking at him. Though I know I don't stand a chance with him. Besides
the fact he likes girly boys he's way too young for me."
I was shocked my mother would say that to me. But that wouldn't be the
last time I was shocked that day. My mother had a few more surprises in
store for me.
My mother held me out at arm's length and looked me over before saying,
"I'm going out for a few hours. There's a roasting chicken in the
refrigerator, put it in the oven at around three. Also put in a couple
of potatoes to bake and there is a bunch of asparagus in the fridge,
we'll steam those when I get home."
"You want me to cook?" I asked stupidly.
My mother laughed and said, "Honey I know you know how. I've been
teaching you most of your life. Now you're going to be the woman in your
relationship its high time you start doing it. After all a man can't
live on sex alone, though most would like to try." She laughed again
before grabbing her purse. After a brief kiss on the cheek she was gone.
Even after she was gone I was still in shock over what we had talked
about. I always knew my mother was a loving and understanding woman. She
never berate me for any thing other mother's would carry on about. Even
when she caught me masturbating it wasn't any big deal to her. She never
told me fibs about the palm of my hand growing hair or any such
nonsense. All she really told me I should lock the door.
When I got up to the bedroom I had to go to the bathroom and this time I
had to remove the butt plug. As soon as I did I saw it was covered in
fecal matter and it grossed me out. I washed it as quick as I could but
it left a lasting picture in my mind. Even so I still put it back in
when I was done going to the bathroom.
After the bathroom I went into my bedroom and turned on my computer. I
had about two hours before I had to put the chicken in the oven and I
was all caught up on my homework.
Normally I would play an online game but this time I didn't feel like
it. I started searching the chat rooms to see if any of my online
friends were on. None of them seemed to be on, but a room called Tranny
girl quickly grabbed my attention.
The room was filled with about fifteen people and I watched as they
chatted to each other. I've never been in an adult chat room before, as
my mother didn't want me to go in one. Though I wasn't sure why as the
kids chat rooms could get pretty raunchy at times.
I watched as what I thought were guys talked on and on to the ones that
sounded like trannies, though I really couldn't be sure. I knew in chat
rooms there was more lying going on then truth. Most of the talk was
pretty graphic, as the guys told the girls what they wanted to do to
them.
I noticed one girl called T-rose didn't talk back to the guys when they
started talking about sex. She would just say a good girl didn't do that
sort of thing.
After watching her chat for about twenty minutes I instant messenger
her. "Are you a real Tranny?"
It took a few minutes before she IM'd me back. "Yes I am Sweetie. Why
would a young thing like you want to know?"
"I just wanted to talk to a real Tranny as I want to be one," I wrote
back.
"Really you're a little young for that. Just barely eighteen though I
have hear most girls wanted to be a girl their whole life. What do you
want to talk about," she asked.
"I was wondering how you clean your bottom so there's no mess. My lover
wants me to keep a butt plug in till he makes love to me for the first
time. When I pulled it out the first time in was covered in. Well you
know."
"LOL sweetie. Its not a problem, you just need to cleanse your bottom
after you go to the bathroom. I do it each morning and any time I go to
the bathroom." She wrote back.
"I know I sound naïve but how do I do that?" I asked.
"You are a new-be. It's easy, go to the drugstore and buy an enema. I
like the one you can reuse but the disposable one will work just as
well," she told me.
T-rose was pretty helpful as we chatted on for well over an hour. She
told me about hormones and breast implants. I found out she lived in New
York City. She told me to save her screen name so we could chat again
and maybe meet when I was in the city. She then had to leave, as her
honey wanted some loving.
Once she was gone I did a search on the web for tranny sights. I was
actually surprised when I saw how many sights there were. Most had
pictures of trannies and some had small clips I could watch if I wanted
to. I was really interested in sights that could give me some help. I
did notice that almost all the pictures I saw, the tranny didn't have
any pubic hair. This made me wonder how I would look with out pubic
hair.
At three I went down to the kitchen and started dinner. I knew how my
mother seasoned the chicken before she put it into the oven. I also knew
to poke the skins of the potatoes with a fork before they went in. I
took out the steamer and put water in it but I didn't turn on the heat.
About a half-hour later my mother came home carrying several bags and a
few boxes. I was actually surprised she had bought so much as she
usually only bought one outfit at a time. This much was unheard of.
Out of one of the bags she pulled a white and blue bottle and asked,
"Have you shaved your legs yet?"
"No not yet," I told her as I felt my face start to heat up with
embarrassment.
"Take this up to the bathroom and use it on anywhere you want to remove
hair. Wait about ten minutes then shower the lotion off. After that put
on a pair of shorts then come down here. Don't put it anywhere that will
show when you wear your boy clothes." She told me.
As I took the bottle from her I saw the bottle was hair remover. I still
found it hard to comprehend why my mother was doing this but as always I
did what she told me. I took the bottle and went up stairs to my
bathroom.
I stripped off all my clothes and started putting the blue green lotion
on my legs. Seeing it was hair remover I went and coated my balls and
all over my pubic area. I also did my chest and tummy as well as my
underarms. By the time I was covered in the lotion I realized it burned
slightly and it felt itchy all over.
I waited the ten minutes like she told me then jumped into the shower.
As I washed off the lotion I saw my hair went with it. By the time I got
out of the shower my legs pubic area my chest and my underarms were
devoid of hair. My skin felt smooth and soft where I used the hair
remover.
After the shower I went and put on a pair of panties for Stan and a pair
of shorts for my mother. I then went down stairs to our living room
where my mother was waiting.
As I walked into the living room I saw neat piles of clothes on the
sofa. My mother was sitting on one of the armchairs holding something
that had garters attached to it. It was white and covered in pink
flowers.
She came over to me and said, "There you are, see all the pretty things
I bought you. Next time we'll go shopping together now that you have
your own clothes to wear." She then wrapped the thing she was holding
around my torso.
"Mom what is this," I asked as she started hooking the hook and eyes
together up my front.
With out slowing her progression she said, "This is a corset baby. It
will pull in your sides and give you an hour glass figure. With any luck
it will pull all your baby fat up to your chest and give you a little
cleavage."
I couldn't believe my mother was doing this to me. I mean how could she
not only accept the fact I wanted to be a girl for Stan but embrace the
idea and help me achieve it. I was so stunned I just let her have her
way with out saying a word.
After she connected all the hooks and eyes she turned me around and
started pulling on the laces in back. On the first pass she pulled the
laces snug >from the top to the bottom. She then pulled them tighter
from the bottom to the top. At this point it was a strain to breathe,
but not difficult. She then pulled the laces even tighter and it felt
like any excess fat and skin I had was being pushed to my chest. At this
point I could only breath in short breaths and I was starting to feel a
little lightheaded.
Once the laces were as tight as she could make them my mother came
around to my front and pulled up on my breast. When she was done I was
amazed I had two small tits. They weren't very big, about the size of a
lemon but they looked like breasts.
My mom went back to the couch and picked up a small bra before coming
back over to me. The bra looked like it matched the corset with the same
flowers that adorn the corset. She wrapped the bra around my chest and
snapped it together behind my back. The bra was made of satin and it was
padded. It pushed my breast together adding size and shape. Looking down
I could see the bra gave me a small cleavage that made it look like I
had real breasts. Though I couldn't say so to my mother I was thrilled.
As my mother went back to the sofa I asked, "Mom why are you doing this?
I mean most mothers would have a fit if they found out their son wanted
to be a tranny."
My mother giggled and said, "You're probable right about that, but you
should know by now I'm not a conventional mother. I've never closed my
mind to other people regardless of what they are or whom they sleep
with. I understand you need loving too and more than I can give you.
Besides I've always wanted a girl I could dress up in pretty clothes. I
thank god every day for giving me you and I never wished you were a girl
instead of a boy, but if you want to be a girl then I want to help you.
And if you don't mind I'll have some fun helping you to become one."
I saw what looked like tears forming in my mother's eye but she blinked
them away before showing me a pair of stockings still in their package
and asked, "Do you know how to put these on or should I show you?"
After telling her I did she handed me a pile of clothes and said, "Good
while I go check on dinner you change into these. Oh in case you don't
know it, the panties go on over the garters. This way when you have to
go to the bathroom all you have to do is pull down your panties.
After she left the room I looked over the clothes she gave me. There was
a pair of panties that matched the corset and the bra. There was also a
white short sleeve sweater and a brown corduroy mini skirt with a chain
belt. For shoes I was given a pair of two-inch pumps.
I took the clothes upstairs to my bedroom and put them on. Seeing my
mother bought them with out measuring me they fit perfectly. The skirt
was very short though the hem did come down below the tops of my
stocking by a few inches. The heels were a little snug width wise but
not too bad. And the sweater was V-necked and it showed off my new
cleavage.
I was actually surprised how sensitive my legs were now I didn't have
any hair on them. Now that my legs were silky smooth the stockings slid
up legs easily and the sensation I felt was erotic. I couldn't help
getting an erection.
Once I was dressed and looked at myself in the mirror I could see the
difference the corset made to my body. My sides were pulled in giving me
a nice hour glass figure like most girls and the stockings made my legs
look beautiful now that I had no hair to ruin the look. Even though I
didn't have any make up on I thought I looked pretty good and I thought
I could pass for a real girl.
When I went back down to the kitchen my mother took one look at me and
said, "God you are beautiful. I could see why Stan was so taken with
you. Come help me set the table and we'll eat dinner. After dinner I'll
teach you how to put on make up." I blushed from her praise and the fact
that she knew about my male lover.
Eating diner turned into a lesson as my mother taught me how to sit and
eat like a woman. She had to counsel me several times to keep my legs
together, as I didn't want someone looking up my skirt. She taught me
how to cross my knees and at the same time keep my legs together.
Sitting up straight was not a problem as I normally did so but tonight I
really had no other choice, seeing the corset wouldn't allow me to sit
other wise. The corset also prevented me from eating my normal meal. Due
to the constriction on my stomach I was only able to eat half my normal
portion. By then I felt like I had eaten a holiday meal.
After dinner and after we did the dishes my mother and I took the
clothes she had bought up to my room. After putting them all away she
opened a bag that was filled with cosmetics. She then began to instruct
me on what to use and when to use it. Once she had my face all made up
she had me wash it off so I could do it myself. Over and over again I
had to wash off my face and reapply the makeup.
This lasted until eleven in the evening before my mother was satisfied I
knew what I was doing. She then handed me a bag and said, "Every girl
should know how to keep herself clean and fresh. In your case you'll
have to do it differently than a normal girl. You'll find what you need
in the bag and you should use it each day." With that said she stood and
kissed my cheek before telling me goodnight.
When I open the bag I found an enema kit inside plus three bottles of
concentrated soap. At first I was relieved that I didn't have to go out
and buy one, but I was also embarrassed that my mother had though to buy
it. That told me my mom knew why I would need it.
Even though I was embarrassed about the situation I stripped off my
clothes so I could go into the bathroom and use the enema for the first
time. I read the instructions carefully until I was sure I could use it
correctly. I filled the bag with warm water and a little bit of the
soap. I pulled the butt plug from my bottom and washed it. I then pushed
the nozzle into my hole and open the valve to release the water.
At first the warm water felt really good as it started to fill my
rectum. I had a sense of euphoria, as it seemed to fill every available
space. When I started feeling full I started to hurt as my stomach
started to cramp up. I almost stopped the enema but I saw I only had
about half the liquid in me. I let it continue, as I was sure I should
take it all.
I was relieved when I saw the last of the fluid leave the bag. I sat on
the commode and pulled the nozzle out of my asshole. That was followed
by a torrent of liquid that smelt awful.
Considering the smell and the dark brown water in the bowl I decided to
give myself a second enema just to be sure I was clean. The second enema
didn't hurt near as bad as the first one did. This one didn't smell as
bad and the water in the bowl was only slightly darkened. The third
enema came out almost the same shade as it went in so I thought I was as
clean inside as I could get.
After my bottom was clean and I reinserted the butt plug I scrubbed my
face with a facial scrub my mother had gotten to remove all traces of
make up. I then took another shower before going back into my bedroom. I
found a new nightie that my mother had bought and put it on. I actually
preferred a nightgown to the pajamas I normally wore. I fell into an
exhausted sleep as soon as my head hit the pillow.
The first thing I did when I woke up was pull out the butt plug to check
on its cleanliness. To my delight I found it to be as clean as it was
when it went in. I actually felt overwhelmed with happiness for this.
Knowing this was the right thing to do, I gave myself two move enemas.
As I put in the butt plug I noticed I didn't feel any discomfort and it
surprisingly slid right in. I knew this meant I could soon start using
the larger butt plug like Stan wanted. I then dressed for school in my
normal clothes before going down for breakfast.
When I walked into the kitchen I found my mother at the table. This was
not unusual as we always had breakfast together. The only difference
this time was my mother was dressed to go out.
"Are you going somewhere?" I asked as I sat down across from her.
"I'm going to see a lawyer about the sale of the restaurant. Now that
I've decided to sell I want to get it over with." My mother thought for
a few seconds and said, "Actually we're in the final phase of the sale.
I knew you didn't want the restaurant after you finished college so I
didn't tell you about the sale until now. I hope you don't mind?"
She was right about me not wanting it, as the real reason I was going to
college was to get away from the restaurant. It never really held any
interest for me. "I don't mind at all Mom. When do you think the sale
will be final?"
"I'm hoping for the day before you graduate," she told me as she took my
hand. "I'll need you at the signing seeing you are half owner."
"Just let me know where and when," I told her as I stood to leave. I
kissed my mom good bye as I did every morning and went off to school.
Before I left the kitchen she said, "Honey when you come home change
into something pretty. Don't worry about the corset. I just wanted to
show you what the right foundation garments could do for you. I should
be home around four or so."