Date: Mon, 24 Sep 2001 23:29:50
From: Veronica Eggert <veronica_tv@hotmail.com>
Subject: A Bet Gone Bad

(The following chronicles a day I had as a student in London and what could
have been)

It is a late morning as I am walking to class. I live all the way on the
East End in a small rat hole that I can't afford. It's a long walk through
crowed streets everyday, but on this particular day things were going to
change. A gentleman asks me for directions and in the process of our brief
conversation he indicates he knows someone form my hometown back in
Maryland. He offers to buy me a drink so we walk into a corner Pub. He is
fascinated with US politics and starts asking me a number of questions. My
history isn't too good as one-thing leads to another he convinces me to bet
him on the order of the Speakers of the House. Before I know it, I am out
$300, all the money I need for the next two months rent. I'm not a welcher,
so I go to a cash station and get the funds. I know I had been swindled but
I view it as a life lesson. I try giving Alex, the stranger, the cash,but he
hesitates and says I can keep the cash if I agree to go to a play that night
with him. The catch is simple, I agree to go but he'll flip a coin, if it's
heads I go as my normal self, if it's tails I agree to go as a woman. Either
way, I don't owe him the $300. I quickly agree to the proposal since even
the embarrassment of going out dressed, as woman isn't as bad as having no
money or a place over my head. I lose the toss.
I spend the whole rest of the day affecting my transformation. I go to a
woman's saloon and solicit help to make me up. They wax all of my body hair
off, pierce my ears, perm my hair, and against my strong protests, shape my
eyebrows. (this will look funny at school tomorrow. I then put on sheer
black stockings and attach them to an elastic garter around my waist. This
seems natural, maybe because I have taken them off of women in the past. On
the suggestion of the woman at the saloon, I then proceed to put on a tight
cinching corset that pulls my waist in a good two inches and pushes up my
chest. I slipped on an innocuous little black dress that hugs my body and
shows off a femine looking figure. I finally slip on a pair of 4" black
heels that have straps that wind-up my legs. I thought of going smaller,
since I was unsure about walking in heels, but I decided I always like woman
in heels, so that I would practice what I preached.
My heart races as I got into the cab and exposed myself to the outside
world. I met Alex at the restaurant but the events were blurred because I
was so nervous that everybody was starring at me. After three bottles of
wine latter I finally let go of the frieght and settled down into a nice
conversation. I ended up telling Alex of my predicament of not being able to
find work and meeting rent and tuition expenses. He smiled and suggested a
solution, one I might or might not like.
Alex said I could stay in the extra room at his house but only if I agreed
to a series of 8 predetermined bets. He would give me 200 a week but if I
lost that week's bet I would have to undertake a new form of humiliation and
servitude. The schedule went like this.
Bet 1/: If while watching a she-male giving a guy a blow job, I got a
hard-on, I would have to dress like a sissy slut when I was in his house.
Bet 2:  If I ever put a run in my stocking, I would have to give him Blow
jobs on demand.
Bet 3. If I ever spilled any of his cum, I would let him pop my as cherry
and have free access whenever he wanted
Bets 4-6 were more insidious. He wanted me to lose weight to look more
feminine. He said that if every week I didn't lose three pounds the first
time he got to pierce my nipples, the second time I would have to have laser
hair removal so that I never grew back body hair, third time I would agree
to have breast implants and tattooed eyeliner, the fourth time he got to cut
of my balls and put them in a jar.
The bets scared me. I wasn't gay or even interested but I need the money and
the housing. I decided I could win these bets or least drag them out until
the end of the semester.
I moved in. Before, I even got to my room Alex handed me a beer and sat me
down in front of his television set. He popped in a VHS but instead she-male
action it was regular porn with bondage. I was ready not to react to his
she-male porn but after an hour of regular porn and three more beers I was
getting honey. Alex got up and swapped in a new tape. Before I realized what
I was watching I was watching a she-male blowing a guy. Alex reached over
and grabbed the hard-on in my pant and said "welcome home sissy, you room is
already full of your new clothes"
I went into my room and changed into small leather min skirt with fishnet
hose and a spandex top. I kept telling my self I could get through this and
a least I could pay tuition.
Then my balloon was shattered. As I walked down the hall to prove my
compliance with the bet, I stumbled as my heel caught part of the carpet. I
looked down and saw a run in my stockings. The blood drained from my face. I
had only been here for two hours and I had already lost bet two. I had
resigned myself that at somepoint I would lose bet two but I thought it
would be weeks and close to the time when I was scheduled to go home.
Alex of course saw me stumble and its effects and ordered me to come over
and pay-up. He took my shoulders and pushed me to my knees. He undid his
trousers and I tried to look away. I had never even touched another man's
cock and now there was a huge erect one not an inch from my mouth, a mouth
with ruby red lipstick. This was not going to be fun. Alex moved the
situation along a little by forcing my lips to his head. My lips slowly
gave-way and let his cock into my mouth. I tried to think of something other
than the fact that I was in a strange mans living room, dressed like a
female whore, sucking his cock. My lips formed a tight seal as I continued
down his shaft. Then almost instinctively I  began moving mouth up and down
on his shaft. Then with almost no warning my mouth filled with a salty
liquid and it just kept coming. I found my self gagging and spitting just to
breathe. I had now lost bet number 3.
I knew I wasn't going to like this new housing arrangement. A number of
weeks went by in which I felt like Alex's person pin cushion. I was always
sore at school but strangely relieved to get home and back into my hose and
heels. I had now lost 12 pounds and was looking hot in my tight clothes.
What was happening to me?
Then it happened on week five, we ate a large pasta dinner, followed by my
crawling under the table and giving Alex head for desert. When I was done,
he announced it was weigh-in time. I got worried. We did weigh-ins on Sunday
night and I had always made a point of not eating on Sunday's. Then I
realized it was Sunday and not Saturday as I had previously thought. I got
on the scale, I had only lost 1.5 pounds. My heart dropped into my stomach
like a stone and I started to get sick to my stomach. The next day I had
additional jewelry to wear. I now had to lose 4.5 pounds in a week, I
failed.
Here I was, with 8 weeks left in the semester and I was in the doctors
office having them burn off all of my hair follicles. I kept trying to
rationalize that I could still lead a life as a normal guy but I ended up
crying all the way home as I felt the smoothness of my crotch rubbing
against my panties. I felt like running, but I didn't know where to go.
I started fasting and exercising. At the next weigh-in I made it by a hair,
hair I didn't have. All I had to do is make one more weigh in and I was home
free from the potential life altering surgeries.
Alex was horney that week. I think he just wanted to fatten me up with his
cum. I must have turned ash white when I missed weigh-in by two ounces. I
felt faint. I knew I couldn't go through with permanent tattooing and
breasts. It had gone too far. Alex could see this on my face. He went to the
kitchen and brought me back a wine. I started to feel dizzy. When I woke it
felt like a car had hi me in the chest. Then I looked down and saw C cup
breasts. I ran to the bath room, and although my face was still swollen, I
could see eyeliner around my eyes and a redline outlining my lips. I took
some aspirin and cried my self to sleep.
I was slowly getting used to my new center of gravity and the fact that my
life had changed forever. Three months earlier I was a sex crazed
heterosexual man chasing woman, and now I was no more than a cum sucking
sissy slut. Oh had I not taken the bet.
Alex called for another weigh-in. I knew I had lost the few onnces that I
failedby the week before since I had starved my self since the surgeries. I
got on the scale and saw that I had actually gained 4 pounds. This couldn't
be right...then it hit me...I now had breasts.
I now work at a gay nightclub as their receptionist, selling my self for
extra cash. Alex has long asked me to leave, my schooling being finished. As
I walked out the door, Alex grabbed my hand and deposited a small box. On
the tube I opened the box to find that Alex had turned my balls into
earrings. I thought I'd cry but instead I put them in my ears and stared at
the crotch of the guy sitting across from me.