The College Wager
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The Wager free porn video
Chapter 1
"Shit, shit, shit, Tom, how the hell did we let ourselves get into this
situation?"
"Greed and overconfidence, love, greed and overconfidence, we only have
ourselves to blame."
"Yes, but we knew that little shit Justin was not to be trusted. Sooner
or later he was going to catch us out."
Justin had originally been my closest friend, right from primary school
days. We had always been hugely competitive and I generally had the
upper hand. We had indulged in dares and bets right from when we were
nine or ten. We would race each other on foot, on bikes, in the pool and
in boats. Competition was everything.
The loser would have to pay a forfeit and the forfeits escalated over
the years. At first it was things like kissing the school bully (very
painful, I lost that one) or stealing girls knickers and wearing them to
school, shouting out a rude word in class. The forfeits were always
getting us into trouble and giving us a reputation. It was fun at the
start.
At the grammar school the challenges escalated. They ended up with us
both having criminal records. Mine was as a result of ending up having
to walk into our local police station, naked and ask the time. I was
fourteen years old. I could have been done for indecent exposure but
ended up with a formal caution for wasting police time. Justin ended up
with a conviction for breaking and entering. The forfeit was to get in
to the sacristy at the local church and liberate a bottle of communion
wine. The dozy git chose to drink a bottle and a half of the wine and
pass out. He was found by the verger. If he had not been so foul mouthed
and aggressive, when he came round, he would probably have got away with
it. At the age of fourteen he had a conviction for breaking and
entering.
Our wagers carried on through university and later, when we each went
independent as software designers. The wagers escalated and Julian got
more underhand and sneakier with each wager. One major falling out was
in the first year after university. Justin reneged on a ?500 bet saying
that the terms of the bet were different than we had originally agreed.
As a result we started to specify the terms of the wager and the forfeit
in writing. We then got a lawyer friend to turn the wager into an
enforceable contract. It was no problem because I won most of the time.
Every time I won, Justin would come back to me with another wager. I was
reluctant to continue because the wagers kept escalating. Justin just
kept badgering me saying that it was only fair to give him a chance to
gain back some of his losses. I had to be very careful every time I
accepted a wager. Justin had become extremely devious. Fortunately I
understood him well enough to see the traps that he had set for me.
Justin had started to get badly out of control when we were at
university. He persuaded me into a bet that in the long run turned out
wonderfully for me. There was a very attractive girl called Samantha, in
the second year with us. She was very shy around guys but very bright
and as good as I was at computer sciences. The bet was to go on a date
with her and return with an article of her clothing.
I thoroughly enjoyed chatting to her and fell for her straight away. I
knew she was shy and I did not want to spoil my long term prospects by
rushing things. Justin, the devious bastard, came in apparently grief
stricken that his mother had been diagnosed with terminal cancer and
only had weeks to live. He went straight to Sam and broke down in tears
in front of her. Sam, being the lovely person that she is, started to
console him. From that point he played her like a violin. He kept
escalating the grief and needed much care and attention. He eventually
got her to his room and fed her a drink with a date rape drug in it.
When she was out of it he stripped her and took photos. He kept her slip
when he reclothed her. When she came round again, Justin told her that
she had passed out and that he was just about to call an ambulance when
she came round.
When I found out what Justin had done I paid my debt and then hit him as
hard as I could. He had a beautiful shiner and I had a swollen hand. I
was the winner in the long run. Sam was now my partner, my wife, my
lover and my best friend.
The stupid bet that we had lost was one that we knew for definite that
we would win. I should have known that something underhand was taking
place. Justin had pestered us into a series of escalating wagers, each
of which he had lost. The previous one had been a competition for a
contract. Not only did we win the contract but we won ?20,000 from
Justin.
Justin had pestered and pestered to have another wager. I had told him
that it had got totally out of hand and that we were never going to have
another wager. Justin went on and on about the unfairness of ending
after he had gone through a long losing streak. He claimed that one last
wager was only fair. His suggestion surprised us. We were both bidding
for an NHS project. The project would be the biggest we had ever gone
for.
We had done more groundwork and research on this project than ever
before. We knew that our bid was very competitive for price. We had
discussed our bid at length with the end users who were delighted with
our proposals. The finance people were pleased with our financial
proposals and their IT department thought we were great. All it needed
was for the procurement committee, or more importantly the committee
chief, to sign on the dotted line. It was as close to a done deal as
possible.
Justin's wager was his house against ours. We had a lovely large house
with a secluded garden and a large studio which we used as our work
space. We had bought the house a year ago, off the back of our
profitable and thriving business. We had had five years of steady growth
and profitability and the bank loved us. The house was worth nearly a
million pounds, the value had fallen slightly over the last year because
of the recession. The house was mortgaged to the bank for a bit over
?900k. We thought that we would only be wagering the ?50-100k worth of
the house that we actually owned. A huge bet, but we had over ?50k in
the bank, and could raise the balance by selling cars and borrowing a
bit more money.
What fools we were. First we had not even considered that we could lose
the bet. Secondly, we had stupidly misread the bet. The bet was for the
full, unencumbered value of the house, not the balance. We owed Justin
the full value of the house. Justin's lawyers had moved fast to
sequester our company as security. In order to meet the debt, Justin
could strip us of our only asset of sufficient value. Justin effectively
owned us.
Our company owned all our intellectual property and the income to come
from the systems that we had designed. We were both contracted to the
company for all our future developments for the next five years. We had
become his slaves overnight. He owned us lock stock and barrel. We
consulted our lawyers to see if there was a way out. We looked at the
possibility of selling our company or our intellectual property. The
lawyers confirmed that with Justin's seizure of the company, he had
blocked our ability to liquidate it as an asset. They only confirmed
what idiots we had been. We would be slaves for five years and at the
end of that time we would be penniless and starting again from scratch.
It would hurt like hell but we could do it.
We steeled ourselves to accept defeat when we had a message that Justin
wanted to make us an offer. When we met Justin he was attended by his
lawyer and two large, ugly men. It was just as well for him as I think I
would have beaten him to a pulp otherwise.
He said that he wanted to offer double or quits. If we lost then we
would have to hand over the business and remain working for him on our
existing contracts for ten years rather than five. If we accepted the
wager, he would release our company and other assets back into our hands
for the duration of the wager.
The terms of the wager were typical of Justin. He had developed into a
very twisted and vicious person.
"Right my lovely friends, the broad terms of the wager are as follows.
You will have to get divorced and you will have one year to find a man
and get engaged to be married. The wedding has to be already booked
before the year is up. The man must be heterosexual, healthy, under 45,
a British citizen, worth over ?250k net and know nothing about the
wager. The wager includes having to have spent at least three nights in
the same bed with the man before the year is up."
"There is no way I am letting Sam go through with that."
He had a wicked grin that split his face.
"Who said anything about Sam. It's you that will have to meet the terms
of the wager."
"What? You must be joking. I am a man remember."
"Well you may be for now, but not for long."
Justin was laughing when he said that the man had to believe that I was
a woman. He told us that we had two weeks to decide.
Chapter 2
I was as angry as hell. I started listing down our options.
1. murder Justin (Satisfying but probably not practical)
2. work out the five years and start again
3. accept the wager
4. run away (Would not be a long term solution)
5. declare ourselves bankrupt (Would not get us out from under)
6. find something on Justin to put him in jail
7. find a loop hole.
That left us four options. The last two were speculative. That left
giving in and being slaves to Justin for five years, or accepting the
ridiculous wager.
I was still raging away, saying that I would take on the wager just to
spite him, when Sam stopped me.
"Tom, don't be so bloody stupid, there is no way that you would want to
stop being a man. Just think before you start contemplating being a
total idiot. Even if it was a possible starter, just think what the
wager would mean for us, I need to say what it would mean to me. I think
the idea of divorcing is not a problem because we could remarry. What is
more fundamental is what it means in terms of three things, my
relationship with you, my sexual needs and my values.
I love you and the you I love is the one I see before me. We trust each
other in every way and believe in each other. If you are going to con a
man into proposing marriage you will have to change in so many ways.
Firstly you will have to prepared to lie and cheat an unsuspecting
person. The Tom I know could not do that. In order for you to con the
man you would have to be a very convincing woman. In order to do that
you would have to change massively and I do not know how I would feel
about the person you changed into.
Secondly, when we first got together I was naive sexually. You woke me
up to the joys of being a full blooded heterosexual woman. I love sex
with a man, with you. If you wore women's clothes and started to become
female, I do not know how I would react, but I know I am not a lesbian."
Sam could see that I was wound up and not thinking straight. She was
very quiet and looked very sad. That night we went to a cold bed, not
talking. When we woke in the morning we hugged and had wonderful, slow,
making up, sex. When we finally sat down for breakfast Sam sat deep in
thought.
"Tom, I think there is no way that you should ever even contemplate
taking up Justin's wager. But, and it is a huge but, I am prepared to
help you see what you would be like as a woman. I hope that it will
convince you that it is a bloody stupid idea. We can then grit our teeth
and survive five years of hell with Justin. It is the easier, safer
option."
We spent the morning preparing. First we went to Marks to get a bra and
panties in my size and got some hold up stockings. We searched the
charity shops for clothes in my size that would make a sensible outfit.
It had us both laughing like naughty children picking out inappropriate
and outrageous options. In the end we had a selection of stuff in my
size that went together. We even found a pair of shoes, in reasonable
condition, that were my size and that would go with the outfit.
When we got home Sam systematically removed all my body hair using a
depilating cream. It took ages and left me feeling burnt and raw. The
applications of a soothing cream felt wonderful and restored me to a
feeling of ease. The hairless legs looked so different, but it was the
arms that shocked me most. Suddenly they were not mine. Removing the
hair from pits and cracks did not seem as strange as having hairless
arms.
Sam then washed and conditioned my hair which was long for a guy, almost
shoulder length, with her own special shampoos. The result was that my
hair was more full and shiny than usual. Next Sam wound my hair,
tightly, over hot rollers. It was uncomfortable but bearable. My nails
were the next task. They were filed to some sort of shape and then both
toe and finger nails were given coats of deep red polish.
We then started to get me dressed. Sam squeezed and manipulated my balls
till they, rather painfully slipped into my body cavity. With that done
she pulled my dick back between my legs and taped it down. It was
uncomfortable, but bearable. She then pulled the panties up my legs.
They were tight and gripped my junk into hiding. When I looked down it
looked very female.
Next came the stockings. They felt wonderful and silky and erotic on my
legs. I could feel my todger trying to stir within its restraints. If
stockings felt that good, I could get used to them. Next the bra, Sam
helped me fix it on and then stuffed the two cups with seed filled
stocking socks that had been tied off in the rough shape of a bust. When
Sam put them in the cups of the bra, I could feel my balance shift. They
felt heavy on my chest, dragging me forward.
"Jesus, Sam, you did not have to make them this big."
"God, what a wimp you are. That bra is only a B cup. Mine are C. you are
a fair bit bigger and much heavier muscled than me. I should have given
you a D cup."
Next came a thigh length slip and then a very fine long stretchy grey
woolen dress. It was long sleeved, with a high neck and came down to mid
calf. Sam then put a deep red wide belt around my waist and pulled it in
so tight it felt as though my lower ribs might crack. Sam then started
on the make up. First the foundation, then she spent ages on the eyes.
There was so much blending and shaping going on that we were a full
twenty minutes just on that. All this time I had not been allowed to see
myself. The rollers were removed and Sam brushed out my hair. Sam found
a deep red choker with a small cameo on it and put it round my neck, to
cover my Adam's apple. She finished me off with a couple of bracelets
and a ladies watch.
I then mounted the open toed red shoes and felt as though I was
balancing on a tightrope. My feet, calves and shins protested. Sam led
me to the full length mirror for my first sight of the female me.
"What do you think?"
Standing looking back at me from the mirror was a bloke with a broken
nose, make up, a dodgy hairdo, muscles, bow legs and a frock standing as
if he was waiting to tackle a second row forward. It was not a pretty
sight. Both Sam and I burst out laughing and could not stop. Tears were
running down our faces we were helpless. When we finally stopped
laughing Sam suggested we analyse what we were looking at.
"First thing is to stand up straight with your head up and shoulders
back, yes chin up, that's better. Chest out and legs straight, stand
with your legs together and one heel into the instep of the other. Good.
Spread your weight across the whole of your foot. Now that is better.
From the waist down you do not look bad. You have nice legs and ankles.
Your legs are a bit too well muscled. Your feet are not too big. Your
hips look too slim and your bum too firm. Looks a bit like Jess Ennis's
so I suppose that might pass. The top half is a different. Your eyes are
lovely. Green eyes and auburn hair are a great combination. Your jaw is
too strong and your neck too broad but the overall shape of the face is
not bad. Your hands are not overly large and your fingers are slim and
well shaped. Your torso has far too much muscle and definition and you
have no waist to talk about. There is no chance, looking as you do, that
you could convince anyone that you were an attractive woman.
I like you though, come here."
What followed was some of the most wonderful kinky sex that we have ever
had. Sam slowly stripped me down to stockings and bra and released my
massively straining dick. It was weird, but nice, kissing when we were
both wearing lipstick. The feeling of the stockings on my legs was very
sensual. Sam must have thought so too because she kept rubbing herself
against them. We got so into each other, that we spent a long time
licking and sucking each other in a sixty nine. That was a very rare
event for us. We eventually lay back in each others arms, totally
exhausted and slept like babies.
When I awoke in the morning there was make up all over the pillow and
when I looked in the bathroom mirror my face looked a total mess. A
yawning and stretching Sam came up behind me giving me make up cleaner
and moisturizing cream.
"Sam, just humour me for a moment and give me an assessment of what I
would need to do in order to convince people I was an attractive woman."
"You really want me to do that?"
"OK, top down. You would need to grow your hair, nurture it and get a
woman's style. Get your ears pierced. Eyebrows need shaping and possibly
a shave of your brow ridge. A nose job is needed to straighten and
reduce your nose. Cheek bones are OK. Beard needs removing. You need a
reduction of your jaw line. Eyes are great and lips OK. Neck needs
thinning. Adams apple needs shaving. Muscle mass needs a lot of reducing
and softening. You would need to lose at least a stone possibly two.
Your nipples and auriolas would need to grow. You would need at least B
cup breasts. You would need to find a waist and grow hips. From the hips
down you are fine apart from being too hairy and too well muscled.
That is the easy part. You are a natural alpha male, dominant and very
competitive. You would need to change your behaviour, mannerisms and
speech from very male to female. You would need to change your
personality to lose all that lovely maleness and start to think and act
as a woman. I have left the hardest thing of all to last, you would have
to see men as attractive."
"Wow, why do you make it sound so easy?"
"I'm just telling you how it is."
"I reckon it would be possible for me to act female without actually
changing personality. I could probably keep up a pretense for a few
months."
Sam gave me a look that made it abundantly clear that she thought I was
talking bullshit.
"Tom, trust me on this, it is not a runner."
"Sam, we have thirteen days before we have to submit. We should at least
research the possibility. I can't just give in without checking every
last option."
"OK, but it is a fools errand. I will help you research but you must
know that I am 100% opposed to you trying to take on this wager."
"Thank you Sam, I love you."
Chapter 3
I decided to approach it in the same way that we would any project. I
would identify key target points which had to be reached before other
things could happen and then work out the critical path to those points.
After a lot of discussion I decided that the target points would be.
1. get fundamentals sorted. Nose, jaw line, removal of beard and male
pattern body hair, growth of nipples, loss of weight, softening of
muscles, development of a waist and female body shape, brow alteration,
breast implants
2. create the illusion of an attractive woman in dress and behaviour.
3. find and woo a qualifying male getting them to the point of a
proposal of marriage.
The last part was the determining factor. How long, realistically, would
it take to get through this stage? If we took it slow it would be at
least six months. The shorter the time span, the hotter the romance
would need to be. The hotter the romance, the more sexually attractive
and active I would need to be. Whilst it may be possible to get a
proposal of marriage after a brief courtship, without having first
having sex, it would be extremely unlikely. Couples tended to move in
together before marriage and celibacy prior to a marriage proposal would
be rare. There was a need to allow at least six months for a more sedate
courtship and a more conservative approach.
If that were the case, I would need to be passably female and able to
have some lower level sexual interplay within the next six months. That
would require that I was presentably female within six months. I would
need to be able to look and act like a woman.
After a couple of days heavy research on the internet we came up with a
list of actions that would be required.
1. get registered with a GP as transgendered. (week1)
2. get a referral to a specialist and a psychologist. (week 1)
3. get hormone cream to develop nipples and areolas. (week 1)
4. get hormones off the net until doctors prescribe (week 1)
5. contact a plastic surgeon about nose, jaw, brow ridge and Adam's
apple surgery. (week 1)
6. start diet and new exercise routine (week 1)
7. purchase corsets to start waist training (week 1)
8. start education on mannerisms and clothing (week1)
9. start electrolysis on hair, especially beard. (week 1)
10. start divorce proceedings (week 1)
11. start voice training (week 2)
12. probable first appointment with specialist and psychologist (week 5)
13. researching websites and dating options by Sam (week 4)
14. purchase first clothing and dressing at home as a woman (week 5)
15. undertake first surgery (week 6)
16. probable first hormone prescription. (week 6)
17. first visit to hair stylist and manicurist (week 9)
18. start correspondence with possible targets (week 10)
19. first outing as a woman (week 12)
20. first trial date (week 14)
21. first snog (week 16)
22. breast implants, these have to be left as late as possible to allow
nipples and areolas to grow first(week 18)
23. first date after implants (week 21)
24. selection of target men (week 22)
25. first dates with targets (week 26)
All of those dates were, probably, excessively optimistic. Any delay, or
slowness in development, and the whole timetable was unworkable.
During all that time we would have to keep our business going. That was
not a major problem because Sam usually did all the customer contact.
There would be the massive upset to our family and friends. I would not
be able to explain why I was suddenly turning into a woman and dating
men. I suspected that they would all be appalled by my behaviour. It
amused me to think of how the rugby club would react to their first team
scrum half dressing in skirts and dating men.
When we saw it all down on paper it really hit home what an impossible
task it would be. It also hit me forcibly, what the wager would mean to
Sam. She would be trapped inside a nightmare turning her husband into a
woman and helping him get dates with men.
The residual situation, if we won the wager would be a damaged
relationship between Sam and me. It would mean the loss of friends, the
possible alienation of family. I would be able to remove the implants
and when I stopped the hormones my body shape would return to something
more male. I would probably become sterile and may lose the ability to
get an erection. I would probably need testosterone supplements the rest
of my life and I would have had to have some level of sexual relations
with at least three or four men. I would have led at least one man to
fall in love with me and left him feeling stupid, angry and broken
hearted. My beard would have gone and I would always look feminine.
And the plus side would be? Not a lot, I would understand something of
the woman's lot and we would have our company, our home and a
financially good future. We would not have to suffer any more Justin.
When we finished our analysis it was clear that it was a non starter. We
would just have to grin and bear it.
The ridiculous thing was that, even after going through all that
research and discussion, it had not registered with me, at any
meaningful level, that I was actually contemplating giving up being who
I was and actually becoming female. I was seeing it as a problem solving
exercise and not as a fundamental change in both me and us.
Why I had taken the possibility of the wager in any way seriously, I do
not know. There was a huge gap between what I had been thinking and
reality. The more I thought about it, the more I realized that it was a
total non starter.
Kaylin
- 28.09.2021
- 17
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