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A Life-Changing Experience
by SandraB
Chapter 1
My life has changed forever. Ever since that fateful day almost two
months ago, my life has taken a dramatic turn. I no longer have the freedom
I once enjoyed. Things I had taken for granted are either gone or
drastically changed. The strange thing about it is that I think I am happier
than I have ever been before. Let me go back to that day that changed
everything.
My wife had gone to her mothers for the day. Usually that meant that I
had all of the morning and most of the afternoon to myself. I adored my
wife, Abby. She was beautiful, sexy, kind, funny, smart – the entire
package. She worked hard to support us as I was working toward a graduate
degree. As far as I was concerned, she was as close to perfect as a person
can come. But, as much as I loved her, there was still something missing for
me. I never told Abby, but ever since I was a little boy, I have been a
closeted crossdresser. It started with my mom and sister's clothes when I
was young. When I was in college, several times per year, I would pay to
have a makeover and crossdressing session with a wonderful lady named Cleo.
Once, I even went out on the town with her to visit a gay bar. I freaked out
when a guy tried to flirt with me and we hurried out the door. Of course,
later I fantasized about what might have been. Abby knows nothing of this
part of me. I had resisted for sometime and even convinced myself that I no
longer wanted to crossdress. But, lately, I had not been able to stop
thinking about it.
Now, with Abby gone, temptation got the best of me. I found myself
looking through some of her clothes in the closet wondering what it would be
like to wear them. Both my wife and I are very thin, but she is 5'4" and I
am 5'11". I knew I would have a hard time finding something that would be a
good fit. I decided to start with a pair of black silk panties. They felt so
good. I got braver. I slipped on a black dress that Abby had worn recently
to a dinner party. I loved that dress. It was short and sexy and looked
fabulous on Abby. I looked in the mirror – I had to admit, it did not look
so hot on me! But it sure was fun to pretend. I noticed my cock was now at
full attention. Oh, how I was loving the feel of the fabrics and imagining
myself as a desirable young woman. My name is Steve, but at that moment, I
decided to call myself Sandra (after my favorite actress – Sandra Bullock).
I slipped on a pair of black boots. My toes had to curl up and it was not
very comfortable. But, in my mind, I was Sandra and I was feeling great. I
went to my wife's dresser and opened the top drawer. I pulled out a pack of
her cigarettes. I don't even smoke, but I have always found that Abby was a
sexy as hell smoker. She smoked the long Virginia Slims cigarettes and it
was just so feminine and sensual. I found a spare lighter and went to the
den. I sat on the sofa with my legs crossed. I opened up the cigarettes and
pulled one out. I placed the cigarette between my lips and lit it. I took a
deep drag, just the way Abby did when she smoked, and exhaled the smoke. I
must admit, I thought it must be an acquired taste, but that it did feel
sexy to me. I sat there smoking a cigarette and flipping through some of her
Cosmo and Glamour magazines. I was hard as a rock so and I began to rub my
cock through the dress. It was then that the inevitable happened…Gwen walked
in the door. I never heard the car and I was trapped.
"What the hell are you doing?!", Abby yelled. She stood there with her
mouth open and I sat there like a deer caught in head lights. I had nowhere
to go and nowhere to run. After several minutes of awkward silence, I tried
to explain it away. "It is not what you think", I said. Before I could say
anything further, Abby stormed off to our room and slammed the door shut. I
could hear her crying. I felt like shit.
After what seemed like an eternity, Abby came back out of the room. By
then, I had changed into a t-shirt and shorts that I got out of the dryer.
"You have a lot of explaining to do", she said. She continued with barely
taking time for breaths between questions, "Do you want to explain why you
were wearing my clothes, smoking my cigarettes, looking at my women's
magazines? Are you gay or something? How long has this been going on? What
does all this mean? I am so confused".
I decided to come clean. I told her about my past, but I also reiterated
my love to her and assured her that I was not gay. I told her that beyond
that, I cannot really explain it because I did not really understand it
myself. I was also confused.
"I am going to stay at my mother's tonight. I need to do some thinking. I
will tell mom that you need to work on a paper and can't have any
distractions. It will give me some time to sort this thing out", she
informed. With that, she threw some stuff in an overnight bag and left.
The next day she arrived at lunch time and seemed to be in a better state
of mind. We sat down on sofa together and she looked into my eyes. "I love
you", she said, "and I have decided to help you explore this side of you.
However, we will only do this my way. Do you understand me?". I said yes I
would do whatever she wanted.
Chapter 2
The week went by without much discussion of what had happened. It almost
felt like things were back to normal. Abby only worked half a day on Fridays
so when I got home from classes, she was already there. "Steve, I picked you
up so new clothes. They are lying on the bed. Why don't you go see how they
fit", she announced as I walked in the door. Much to my surprise, Abby had
purchased a couple of outfits for me, complete with some bras and panties. I
could not believe it! "Are you serious?", I shouted back. "You better
believe it, buster", she replied, "Try them on". So I did. It felt so
wonderful but I was worried at appearing too enthusiastic. What would Abby
think? How far will she let me go with this? Was this really happening? My
head was spinning.
"Nice fit", Abby said as she walked into our bedroom. "Definitely much
better than you wearing MY clothes", she added. She then told me to take
them off and to go take a shower. "I am going to come help you take all that
yucky body hair off", Abby inserted. I was now getting scared. Sure, I
thought about what it would be like to have smooth skin without all this
hair, but actually doing it was another thing. But there was something about
Abby that was different. It was as if she had become more assertive and
controlling. For some reason, I did not argue with her, I just did as she
said.
When I got out of the shower, Abby wrapped me up in a pink bathrobe and
sat me down at her vanity. She told me to stay still as she did my make-up.
It took some time but when she was finished, I could hardly believe the
result. There looking back at me in the mirror was a truly feminine face.
"Put on your panties", she ordered, "that is, if you can get them over your
hard cock". She was right, I was as aroused as I had ever been. She then
helped me with my bra and added some breast forms to help me look full. She
then helped me slip on the black dress she had purchased for me. "You do
like black, don't you Steve", she said, remembering that she caught me
wearing her black dress the previous weekend. "What was your girlie name
again?", Abby asked. "Sandra", I replied. "Yes, Sandra, my dear…that is what
I will call you", she said.
Then Abby brought out a box and opened it on the bed. It was a beautiful
brunette wig that she carefully placed on my head. After fiddling with it
and brushing it, she led me to the mirror. "What do you think?", she asked.
I could not speak. I was overwhelmed. I looked like and attractive young
woman. "I must admit", she added, "if I did not see it, I would not believe
it. But you are beautiful. No one in a million years would guess that under
that layer of femininity is actually a man. Well, at least a semi-man". What
did she mean by that last comment I wondered. "You will stay like this", she
said. "I am going to teach you the art of being a woman and we will see how
much you enjoy it", she added.
That entire weekend, Abby taught me to sit, talk, walk and act like a
lady. At one point, she sat me on the sofa and gave a small black purse. In
it, she had already placed some make-up – lipstick, blush, eyeliner, etc.
Also, she had placed a pack of Virginia Slims Luxury Menthol Lights 120s.
She instructed me that over the next week, I was to practice touching up my
make up and also smoking cigarettes like a lady. The next weekend, I was
informed, we were going on a little adventure. My heart pounded with both
fear and excitement.
Chapter 3
When I arrived home Friday afternoon, my wife was waiting for me. She was
dressed to kill. She had not dressed this sexy since we were dating. Our
luggage was packed and I was instructed to put it in the car and then take a
shower. I was also instructed to remove all body hair and that she would
help me get dressed. Waiting for me on my bed was my black dress that I had
worn around the house the previous weekend. "You looked too good in that
dress not to show you off a little bit", Abby yelled from the hallway. A new
pair of black high heels were beside, a little higher than what I had become
accustomed. Abby walked to see me staring at the shoes. "Don't worry, I have
complete confidence that you are going to do great", she said. I was not so
sure.
It was almost dark when we left the house. The darkness gave me some
comfort and I began to loosen up a bit. I had no idea where we were going.
My wife had arranged something for us, and I was not sure what it was. "It
will take us a couple of hours, so you just relax", Abby stated. She added,
"We will have a late dinner when we get there". I kept imagining that the
people that looked into our car would think that there were two attractive
young women going out for a night on the town or shopping. At least that is
what I hoped they would think. The entire trip, Abby kept giving me a pep
talk about acting like a lady and putting in all the things we practiced at
home. I practiced talking like a lady, sitting like a lady, and smoking like
a lady. I was so nervous but also very excited. In fact, I was probably as
excited as I had ever been in my life. Little did I know how soon my world
was going to change and that there was no turning back now.
I had figured out we were going to Atlanta, which was only a couple of
hours away. Soon, Abby was pulling into the parking lot of Sheraton Hotel in
the trendy Buckhead area. Abby went in while I waited in the car. She came
back with room keys and a bellman was there eager to help us with our bags.
As we made our way down the hall, I noticed that the bellman was checking
both of us. I was surprised to discover that Abby had booked separate rooms
with and adjoining door between them. "Why did you do that?", I asked. "You
will see", was her reply. Then she authoritatively instructed me to ask her
no more questions.
She tipped the bellman thanked him for his help. Abby had long ago
instructed me to take off my wedding ring because it just looked to
masculine to wear when I was being Sandra. But for the first time, I noticed
that Abby had removed her wedding ring as well. I started to ask her about
before remembering her order not to ask any more questions. "Let's take a
few minutes to freshen up before we go to dinner", Abby said to me. "I don't
know if I am ready for this", I replied. "Oh, you're ready", she teased
back, "I promise you are more than ready."
Chapter 4
As we headed to the door, there was a taxi awaiting us. Abby must have
asked the bellman to get us a taxi when they were alone in the hallway. I
guess that means we both were going to have a few drinks that night. Abby
instructed the taxi driver to take us to Dante's, a jazz club and restaurant
which was just down the street. The restaurant had a wonderful ambience
about it. We sat at our table and listened to the jazz band playing. We each
had a glass of wine before we ordered our dinner. I was so nervous that I
did not have much of an appetite, but I knew I should at least eat a little
something. After we ordered our dinner, we each had some more wine and
smoked a couple of cigarettes. I was really beginning to loosen up a bit and
enjoy myself. I leaned over toward Abby and said, "Thank you for this. This
is such a thrill for me and I am finally having fun." Abby chuckled, "Oh
honey, your evening is only now getting started. You have no idea what is in
store for you, or for that matter, for us." The way she said it was
frightening. "Abby, what are you talking about?", I asked. Abby leaned
closer to me, "Let me explain, my dear"…
When I said, "I do" to you, you were a man. I am a woman and I need a
man. When I saw you dressed in my clothes, you ceased to be man to me. Sure,
I still love you, but now I can only see you as a girlfriend. I have tried
over the last couple of weeks to see you as my husband and a man. When had
sex, I tried to enjoy it like I had always enjoyed our sex life. But I could
not do it. You are no longer a man to me. However, I still love you, so I
have decided to help you fulfill your desires to be a woman. And as a woman,
you need a man, just like I need a man.
"I am not gay!", I shouted back, almost drawing attention to ourselves. I
even started to cry, but the worst was not over yet. Abby pointed to a guy
at the bar. He looked strangely familiar to me. "That is Jeff from work",
she said. She continued, "Jeff has always flirted with me but I always
rebuffed him because of our marriage. However, because I need a man in my
life and you are unable to fulfill that role, I began to return his flirting
with some flirting of my own." I began to sink in my seat. As the waiter
delivered our food, I thought I was going to loose control and start crying.
I gathered my composure and asked, "Have you had sex with him?" Abby did not
say a word, she just nodded her head yes. "Last week, when you were studying
at the library, I went over to his apartment. I told him all about you and
explained my situation to him", she said. "Stop!", I pleaded, "I would
rather not hear it." "Suit yourself", Abby said, "but you will have no
choice to deal with it soon".
I could not eat. I just sat there staring into oblivion. My whole world
was crashing down around me. But it was about to get worse. Abby motioned
for Jeff to come over. He said down next to Abby and gave her a kiss. "So,
this is Sandra", he said, "It is great to finally meet you." I said nothing.
"Well, you are going to see a lot more of me so you might as well get used
to it", he added. They began to carry on as if I was not at the table. I
kept asking myself, "Why is she doing this to me?"
I got up and went outside. I walked back to the hotel and cried all the
way there. I curled up on my bed and wept. A few minutes later I heard Abby
and Jeff come it. "Sweetie, you might as well get used to this and get a
good attitude about it. I think you may actually discover you will like some
of these changes", Abby said. Then she went back through the adjoining door
to her room. I could hear her and Jeff laughing and talking. Then I could
hear them kissing. These rooms were not very sound proof. Then I heard Abby
moaning. They were having sex right next to me as if to make me suffer more.
I had never heard Abby scream so much in all of our time together. Was she
just putting on a show to humiliate me more or was Jeff really that good?
Either way, it was not a pleasant feeling for me.
After a little while, Abby came back in to see me. "I know that was rough
on you, but that is just how it is going to be. You need to get used to it
Sandra", Abby said. "Besides", she added, "You have a visitor coming in just
a moment and the four of us are going back out for drinks". I was
speechless. What was she doing to me? As I sat still on the bed, Abby began
to reapply my make-up. "Do you feel pretty?", she asked. "Yes", I replied.
"Good, because you are very pretty. And I want you to live it up tonight
Sandra. Think of this as your 'Coming Out Party'. I have a special friend
that I think you are going to really enjoy meeting. He should be here any
moment".
I was suddenly terrified again. Abby explained,
After I told Jeff about our situation, he mentioned it to our co-worker
Gary. At first I was furious with him for doing that, but the more I thought
about it, the more I thought it could be a great thing. Everyone in the
office knows that Gary is gay but there is more to Gary than meets the eye.
He and I had some long talks over the last couple of weeks. He is such a
nice guy and very handsome. It turns out that he is particularly drawn to
"girls like you", if you know what I mean. He is a wonderful guy and he
wants to meet you. And he will be here in about 5 minutes.
I just looked at her in disbelief. However my cock was getting hard and
that did not escape the notice of Abby's watchful eye. "See, I knew you
would like the idea", she said. But I still said nothing.
Chapter 5
I heard the knock on the door and I wanted to go and hide, but I had
nowhere to go. Abby let him in and after exchanging pleasantries, Gary
walked over toward me. "Sandra, it is so nice to meet you. I thought you
were beautiful when I first saw the pictures that Abby showed me, but now
that I see you in person I find that words cannot truly express just how
beautiful you truly are", he said as he looked into my eyes. I really think
he meant it and in some strange way in made me feel wonderful, but at the
same time I felt scared and awkward.
"Let's go everyone", Abby shouted, "We are all going to ride in Gary's
car". Gary grabbed my hand and walked me out the door and down the hall. In
the elevator, I watched Jeff put his hands on Abby's waist. He even kissed
the back of her neck. Why did he have to do that in front of me? Abby sure
seemed to be enjoying herself. Instinctively, I looked at Gary for help. He
put is arm around me and gave me a gentle hug. It felt nice to be comforted.
He leaned over and whispered in my ear, "I really want to get to know you
tonight. Would that be okay with you?". My reply was actually my first words
to him and I could hardly believe what they were. "That would be nice", I
replied.
As we approached Gary's car, I started to reach out to open the front
door. Gary's hand beat me to it as he said, "let me get that for you". I
guess I need to get used to things like that. It was kind of nice. We went
to a dance club just a couple of miles away. Gary and I sat at the table
while Abby and Jeff danced the night away. I was not ready for that and Gary
was very understanding. Initially, he did most of the talking. I just sat
quietly and listened. I really did find myself liking this guy. He was kind,
considerate, funny, and shall I say…charming. I also had to admit that he
was very handsome. He was tall and thin but with a more athletic build. He
told me he was 35 years old and had been married once before he came to
grips with his sexuality. I began to relax a little bit as a drank another
glass of wine. I reached into my purse for a cigarette. As I brought it to
my lips, Gary reached over with a lighter to offer me a light. As I took
that long first drag on my cigarette, I found myself incredibly turned on.
He was such gentlemen and he seemed to love treating me like a lady.
Soon, I began to pour my heart out to Gary. I told him about my feelings
about my marriage, about my crossdressing, about him. I cried a little and
laughed a little too. I guess I was being a typical woman! Through it all,
he just listed with his eyes as well as his ears. He had such a look of
compassion and understanding. The music suddenly switched to a slower tempo
and before I knew it Gary was holding me by the hand and leading me out onto
the dance floor. He wrapped his arm around my waist and I instinctively
placed my arms around his neck. He pulled me close as we slow danced. I
glanced off the side and saw Jeff and Abby dancing. They were looking our
way as well with smiles on their faces. Gary reached his hand to my face and
guided it back in his direction. "Don't pay attention to them", he said. I
stared at Gary's beautiful brown eyes. I began to run my fingers through his
hair on the back of his head. He leaned toward me and gently placed his lips
onto mine. The kiss was so sweet and gentle and I found myself kissing him
in return. It was an incredible moment. My legs became like jelly and I
would have fallen on the floor had it not been for Gary's strong arms
holding me up. The kiss became more and more passionate and then our mouths
opened and our tongues began to explore one another. I knew that life would
never be the same and at that moment, I was very happy about it. The song
ended and the music returned to the up tempo dance music that had played
earlier. I just held onto to Gary's hand as he walked me back to the table.
Abby walked by and whispered in my ear, "I just knew you would like Gary". I
could not reply. But I knew she was right.
"Why don't we go back to the hotel", Jeff said. As Gary drove us back,
Abby and Jeff kissed and ran their hands all over each other in the back
seat as if they were high school students. The strange thing about it was
that at that moment, I did not care. I just looked over at Gary and held his
hand. Abby and Jeff went straight into their room. Gary escorted me to the
door and stopped. "Aren't you going to come inside", I asked. "Not unless
you invite me", he replied. "I would really like you to come in", I said in
return.
Chapter 6
Without saying a word, I took Gary's hand and guided him in front of the
bed. I wrapped my arms around his neck as our lips met again. We kissed
passionately and deeply. I gently pushed Gary backwards so that he was
forced to sit down on the bed. I then began to unbutton his shirt. "Are you
sure about this?, he asked. "Oh, I'm sure", I replied. I took off his shirt
as he slid his body up to toward the pillows. "How about a message? Would
you like that?", I asked. He did not need to answer. I took off his shoes
and socks and threw them on the floor. I unzipped his pants, taking a brief
moment to feel his hard cock. I pulled his pants off and tossed them on the
floor as well. I rolled Gary over and began to massage his shoulders and
back. It felt incredible to be touching a man like this, particularly one
with such well defined muscles. I sensuously and deeply massaged his arms,
shoulders and back. I kissed his neck and ears then I whispered, "Turn over
please".
As Gary now lay on his back, I reached down and began to rub his feet. I
then worked my way to his calf muscles and then up to his thighs. He gently
moaned as I got closer and closer to his big, hard cock. I then began to
lick the inside of his thighs. I would circle my tongue so close to his
manhood without actually touching it. It was driving him crazy and I loved
it. Finally, when I knew he could not take it anymore, I began to suck his
balls. Then I slowly ran my tongue up the shaft of his cock. I leaned over
and slowly took all of him into my mouth. I could actually feel him getting
even harder in my mouth. What a turn on! I began pumping up and down slowly
and then I quickened the pace. I placed my right hand at the base of his
shaft as I continued to pump and suck. I placed my left hand on his ass and
even placed one of my fingers just inside his rectum. Within moments, he let
out a moan and filled my mouth with his cum. I eagerly swallowed every bit
of it.
Gary immediately took my dress and lifted it up over my head. He pulled
down my panties and eagerly took my cock into his mouth. It only took
seconds for me to return the favor and fill his mouth with my love juice.
Then we laid on the bed together kissing and cuddling. It was fantastic.
As our cocks began to harden again, I whispered into Gary's ear, "I would
like you to fuck me". Gary asked if I was sure that is what I wanted. My
reply was to stick my tongue into his mouth and my hand on his cock. "Please
fuck me", I begged. I reached over into my overnight back for some lube.
Gary took it from me and began to rub in on and into my anus. I then placed
some on my hands and began to apply it to his hard cock. I knelt over on all
fours as Gary got on his knees behind me. He began to tease me by rubbing
his cock around my ass. "Fuck me!", I pleaded. He then slowly inserted his
cock into my anus. He eased in until he was completely inside of me. Gary
began to pump slowly as he reached under me to rub my raging hard on. His
fucking began to pick up in pace as did the way he was stroking me. I could
hardly believe that a man was inside of me and it made me feel so good. I
could tell he was about to come inside of me when my own cock exploded with
cum. Within seconds Gary, filled my ass with his cum. We collapsed on the
bed together as Gary tenderly caressed my body. It was the best lovemaking I
had ever experienced.
Suddenly, Abby opened the connecting door. "Sounds like you two have hit
it off just like I knew you would", she said. I looked at her and gave her
smile. I silently mouthed the words "thank you" to her. She closed the door
and I snuggled up closer to Gary. I knew this is the beginning of beautiful
relationship.
The End
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