Clothesline GameChapter 2
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The Big Game - Part 1 free porn video
The Big Game - Part 1 Written by ShariT
Matt Ruggieri is a successful investor in Boston. We met through some
mutual friends a few years ago. We had been out clubbing and competing to
see which of us would hook up with the sexiest girl. At the time I was 23
years old and not quite as successful financially as my friends who were
already making six figure incomes in the financial world.
In the past few years I had lost touch with the guys because we had very
different lifestyles. They went out partying and socializing a lot with
their clients and I tended to stay at home. They often entertained clients
by taking them to sporting events like Red Sox and Patriots games. I
worked from home as a computer consultant and we never really crossed
paths anymore. I would enjoy going to an art gallery or movie but rarely
did as I never had anyone to go with and didn't like to go out alone. I
enjoyed going to games but never had someone to go with.
It was during these few years that my fascination at an early age with
women's clothes began to get more serious. Now that I was out of my
parents' house and living alone I could experiment with no inhibitions. I
began to order everything I would need for a foundation on the internet.
Before long I was spending all of my extra money on women's clothes. I
would get packages from Victoria's Secret and Bluefly weekly. I was
careful to buy sale and clearance items only because I could buy more that
way. I would visit department stores that were in malls far away so I
could buy my makeup and some jewelry. I had built up quite a wardrobe. In
fact my guest bedroom became more of a closet with over 50 pairs of shoes
and boots, nothing less than 3" high heels, in boxes and more dresses and
clothing than I could find space to hang. The clothing felt nice but I
didn't feel as though I looked very convincing.
I guess the more money I spent on clothes the less I had for food and as a
result, and without realizing, I began to lose weight. I also had less
free time as I was always anxious to dress when I got home from work.
After a year or so I woke up one day and realized I had shrunk. I was
still 5'10" tall, but went from 185 lbs. to just 165 lbs. I also lost a
lot of muscle mass. My waist went from 33" to 29" and I realized that now
that my waist was narrower than my hips I started to look better in my
dresses and jeans.
My new thinner male look began to change my experiences. When I did go to
an art gallery I started to attract the attention of men instead of women.
The women that I did speak to talked to me and treated me like a
girlfriend rather than a predator. I met Olivia at an art gallery on
Newbury Street. She was a beautiful girl with a mix of Italian and Greek
looks. She was only an inch or so shorter than me and had an amazing body.
I started to think of myself more as a girl and wondered what it would be
like to look like her and actually be dressed out in public. That New
Year's Eve, my first ever spent alone, I decided if I am going to try it
out I would have to be as feminine as possible.
I began to order diet supplements and hormones. I was careful to eat a
proper diet but began to exercise at home with workout tapes and my
treadmill. I was exercising to Denise Austin and doing Pilates for women
and it all began to take shape. I also started to go to the tanning salon
twice a week. By the end of the summer, just 6 months later, my little
experiment was a success. I was now 145 lbs. and with the help of the
hormones my measurements were 38A-26-38.
During this time Olivia and I became friends. She would invite me to
gallery events as she was the manager. I would always stay behind and help
her close up the gallery then we would go for a drink or coffee and talk.
I could tell she was beginning to wonder about my changes.
"Stephen, are you ill?" Olivia asked.
"No, not at all," I responded. "In fact I have never felt healthier
physically."
"Why did you clarify that you feel better physically, do you not feel good
emotionally?" she asked.
"Well I just don't feel like myself," I responded.
"Stephen, I haven't known you for that long but from all the signs I see
either you are ill, which you say you are not, or..." she paused. "Your
body is changing from something else."
I began to speak, but before I could say anything she added, "I want you
to know that I think of you as a close friend and I hope you trust me
enough to tell me anything."
Her words seemed to be a magical spell that allowed me to feel safe and
open up my feelings. Before I could answer I began to cry. I never cried
in public before, it was a strange new feeling. Olivia held my hand and
tried to console me.
"What is it?" she asked worried. "Are you really ill?"
I had to answer before she started to cry too "I have been trying to get
in shape," I stated.
She laughed a little as she responded, "In shape? Hun, you are wilting
away. You are in perfect shape though if you wanted to be a sexy woman."
I could tell the minute she spoke she saw a light. "OH MY GOD," she
exclaimed.
"Yes," was all I could say.
"Can I ask what started all of this, and what have you been doing to
yourself?" she asked.
For the next hour I told her all about my diet and exercise routine and my
extensive clothes shopping. I also told her that it all started when I was
younger but really began in the last year.
"Do you think you want to be a woman?" she asked.
"I am not sure what to think," I stated. "But I want to find out," I said
with a smile.
It was about 1am by the time we realized it was too late to continue the
conversation so we hailed a taxi. I offered to drop her off first as she
was working the next day and she quietly said, "You're such a gentleman,
for a girl," and declined as I was the closer of the two of us. As I got
out of the cab she said, "We'll have to talk more tomorrow Hun."
I couldn't sleep at all that night. I don't know if it was the threat of
someone else finding out about my secret or the extra few glasses of wine
I had while we talked. I slept in all day and was awakened by the phone
ringing at about 4pm on Friday.
"Steph, are you serious about going out in public as a girl?" Olivia
asked.
"Yes," I said, wondering where this conversation was going.
"Well," she said, "you're going to help me out this weekend."
"What do you mean help you out?" I asked.
"Today, two of the investors in the gallery were in the office checking
the financial records. Anyway, we were talking about different things and
the subject of football came up. I got into a heated debate with one of
the guys, Matt, because he is a Colts fan. Well the other investor Ken
asked me if I would like to go to the Pats-Colts game this Sunday and help
him shut Matt up."
"That's great, so are you going? And how can I help, do you need to know
player names and things to sound like you have a clue what you are talking
about seeing that you have never even seen a football game?" I asked.
"No" she said "I need you to be my double date because they have four
tickets and Matt asked if I had a friend that was a Colts fan."
"Are you crazy, you want me to go out on a date?" I said.
"Steph, I really like this guy Ken. And by the way Matt is really good
looking too, and tall!"
"How tall?" I asked. Wondering if it could be the same Matt that I know.
"About 6'4" I guess," she said. "Because I was wearing my new Prada pumps
with a 4" heel and he was 3 or 4 inches taller than me," she said.
"Oh shit!" I said. "Did you catch his last name?"
"Yeah, it's Ruggieri," she said.
"I can't do it, even if I wanted to because I think I secretly had a crush
on him," I said.
"I used to hang out with Matt and some other mutual friends, he'll
recognize me for sure."
"Steph, I have a hard time recognizing you sine I first met you, and you
told me you were somewhat of a jock before. Trust me when I say he won't
recognize you."
"I don't know," I nervously replied.
"Tell you what, I'll take the day off tomorrow and if by tomorrow night
you think you won't pull it off I'll call and cancel my date with Ken,"
Olivia offered.
"Alright," I replied- "I'll do it."
"Awesome, I'll be at you place at 8am, get a good night sleep Hun."
End - Part 1
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