The Wager
A Short Story
By Maryanne Peters

“Are you proposing a wager?” Professor Harrison Hunt smiled mischievously at his colleague. The tall, sinewy academic leaned against the bookcase in his old fashioned study.

“I would be happy to take your money, Harry,” responded Professor Michael Danes. “It is a bold claim for somebody with my knowledge in the field.”

It was. Mike had been professor of endocrinology at Lakes University Medical School for 4 years now, and had seen many transgender people in that role, and in lesser roles at the school and in medical practice before that.

“Set your terms” Harry challenged. He was confident too. He was head of the University’s Psychology Department with a background in human behavior. For years he had conducted work human sexual behavior, and also in the differences in behaviors between the sexes.

“Well you said ‘anybody’ so we need a masculine subject. Somebody who has never identified as transgender. A trans-person would have a head start.”

“For the set I can select from, go as masculine as you like, but I make the selection from a given set of subjects,” said Harry.

“I suggest they be somebody who has played for the Timber Wolves sometime in the last, say 5 years.” Mike was referring to Lakes University’s football team. A seething pool of testosterone.

“Okay”, said Harry, confidently. Whatever doubts he may have had needed to be suppressed. His only concern was whether he could find a footballer who would be willing.

“I need to meet the transitioned subject and converse with them for a period, say up to 10 minutes, and either challenge them or you, as soon as possible. Only if I do not challenge will you have won.” Mike was thinking what else needed to be covered.

“You need to give me time to find a suitable candidate and get them ready to meet you,” said Harry. “Realistically I need up to a year. You have to meet the subject before this day next year. I am happy to carry the cost of the transition, but I suggest we both put $10,000 each into a fund to cover those costs.”

Mike nodded. Both of them were independently wealthy and this seemed like a small sum for an exercise in fun. But he asked: “So what do I get if I uncover your ‘woman’?”

“You get your $10,000 back, and say $100,000,” said Harry. “Plus the bragging rights on having defeated me for the first time.” He was of course, referring to a long friendship and a sequence of wagers, each larger than the one before. Harry had lost a few bets, but Mike had lost many more.

“Make it $200,000 and you have a bet,” said Mike, extending his hand. He felt that he was on very solid ground this time.

“Done!”

***

“So let me understand this Doc, you want me to dress up as a girl to win you a bet?” Liam Sharp stared at Professor Hunt incredulously.

“You can put it that way,” Harry replied, trying to be honest. “But I think that you need an escape from your present issues. I think this could be therapeutic for you. Work with me over the term break. Stay at my house. Focus on this, like you did on your sports. Win this. I think you can.

Liam thought that his psychology professor knew the right buttons to push. He was a person who always needed to win, but his football career was now over. The damage to his back ruled him out of all contact sport, and chronic groin muscle and Achilles tendon problems took him out of serious competition in most other sports. His loss of confidence had destroyed his relationships with his friends, and with women. He was clinically depressed and was on anti-anxiety medication. He was a mess.

Harry had heard of his problems and had taken it upon himself to offer help, even before the bet had been made. But in Liam he saw the potential to win. As a running back Liam was not big, but he would still make a large girl. He had small hands and feet for his size, big eyes, and not a heavily boned face. If you disregarded the ugly broken nose and a rather too prominent chin, he would have been a good looking young man. Appearance was important, but it was not the heart of the challenge. The trick was feminine behavior. Behavioral differences, in particular behavioral differences between the sexes, was Harry’s area of expertise in his role as Professor of Psychology.

“So what do I get if I win?” said Liam. Just using the word encouraged him slightly.

“My bet is $200,000,” said Harry. “You can have it all if you win. If we win. And if we don’t, I will pay you say, $100,000. Oh, and of course I would pay to reverse any body modification that we may need to make.”

“Body modifications?” A year ago he would have been shocked. But now he just added: “Any modification to this body has to be an improvement.” He was in discomfort and his nose had been broken so many times that he could hardly breathe through it. Sleeping was difficult. His football career had not been kind to him, and now it was over.

“We are talking up to a year,” said Harry. “You stay at my house. As my guest. It is a big house so there is no problem in you having private space. I am sure you will be very comfortable. Plus it will give you the chance to focus more on your studies. I will take you through the last paper you just missed. I am sure I will be able to pass you. And I will tutor you on next semester’s papers. The idea is that you come out of this with a degree, a novel experience, and a positive outlook on life. Even if none of that happens, you are no worse off.”

“Okay,” said Liam. “I will do it. I can hardly say no to the money. But I need an advance on the $100,000. I have to visit my Mom for a few days then I can come back and move in to your place.”

“I can do that,” said Harry. “But I need to have your total focus and obedience on this. If I do, you will be able to pass as a woman.”

“I sure hope you are right about this, Doc,” said Liam. “I could do with the $200,000. And maybe you’re right. I need to focus on something. I just hate being so useless.”

***

“Whatever is in the bag, you won’t be needing it here,” said Harry, once Liam was inside.

The house was even bigger than Liam had imagined. It was old and sprawling, but with even larger grounds. He would later learned that it was the professor’s family home. Other members of his family had moved away from this area, but Harrison Hunt had stayed close to his roots, favoring life in academia over a life of pleasure in a warmer climate.

Harry showed him to his room upstairs. It was large, with an en-suite with both bath and shower. There were large built in wardrobes and a queen size bed, and a large dresser with boxes on it. Outside the room was a small living area with sofa and a balcony overlooking another large living area downstairs, adjoining an indoor pool. Liam has never seen such wealth and luxury.

His mother had been happy to see him, and happy to for the money he had brought. But happiest of all that this project, whatever it was, seemed to have imbued her son with a trace of positivity that seemed to have been lacking in him for some time. That positivity he expressed by asking Harry: “When do we start?”

“We need to get started straight away,” said Harry. “I suggest you have a bath and a shave down. That means everything below the neck. Above the neck will require professional attention. And there are clothes in the wardrobe.”

“Sure, Coach,” said Liam. “Whatever you say.”

“You can call me Harry. And I think that for now I will call you Lee. That’s fairly gender neutral.”

Once alone, as instructed Liam put the clothes he was wearing in a cardboard box provided and ran a bath. He looked in the wardrobe. There were only women’s clothes, and not many of them. They still had labels on them. He found a robe that he could slip on after the bath. There were women’s underwear as well, still in boxes. The boxes on the dresser had a range of cosmetics, all brand new. He had no idea about such things.

Beside the bath were ladies’ razors and “post-shaving” perfumed moisturisers. He did the best job he could. As the bath filled he shaved his body with foam and a razor – legs, arms and chest. As instructed he had added bath salts. The perfume was slightly intoxicating. He rinsed off his smooth body. He imagined that he was running his hands over the body of a beautiful woman. He jerked off. He considered the sexual possibilities of this exercise. He had never worn women’s clothing before. Would it be a turn on?

When he emerged from the bath he looked at his body in the mirror. He had shaved off his pubic hair as well. ‘Everything below the neck’ was what he was told. He pushed his penis between his thighs and covered his nipples with his hands. Yes, he could see the body might pass. Since his injuries, and lack of training, his muscles had wasted away quite a bit. He was underweight, but the legs looked good.

He toweled off with the softest and fluffiest towel he had ever had contact with. He applied the moisturizers, and he savored the perfume. It felt good. For the first time in a long time, he smiled at himself in the mirror. He decided to himself: “I am going to do this. I am going to win this bet”. Liam Sharp was a determined young man. It was the determination of mind rather than the physical prowess that had made him a successful track athlete and footballer, and a very good all round sportsman. When he set his mind to a challenge, he usually succeeded. His injuries had knocked his confidence and his self-esteem, but now he felt that he had something to aspire towards. With the help of his professor, they were going to prove a point. That were going to win.

***

He felt stupid in his first dress. That was because it was so unbelievably stupid. It was a little girls dress. The kind of dress that no little girl would be seen dead in. All pink ruffles and lace. Before he could sit down, Harry admonished him: “No. You need to smooth your dress under your bottom like this, and then sit down. And keep your legs together like this.”

“This has to be a joke, Coach?” Liam still used the term. It was as if he was holding on the masculinity by pretending that this was a training camp. One of those training camps with weird techniques.

“We need to build your feminine persona from the ground up, Lee,” explained Harry. Every woman starts out as a little girl. You need to want the things that all little girls want. To become a princess.”

Liam sat down in exactly the right manner, and asked: “So what’s the game plan? How do I get to be a princess?”

“I have surgery scheduled in a few days,” said Harry. “I want the physical changes made as soon as possible so we can work with them for the maximum period of time. Until then I want you to learn to love all things feminine. I want you to want to be a girl. I want you to understand the joys of not being male. I want to explain those things to you.”

“This surgery is not going to going to be in my crotch, right Coach?” Liam was starting to worry.

“No,” scolded Harry. “We will go through it, but for the next few days we are working on you wanting to be female.”

“So what are the reasons why I want to be a girl?” Harry liked the question. It was not a challenge. Liam seemed to have already bought into this, and was looking for answers.

“Well; let’s see,” said Harry. Being an organised person he had made some notes which he could refer to: “Women live longer, they don’t lose their hair, they achieve more in certain areas, they are more emotionally intelligent. But most women like things that they do that men can’t do. They like it that they can cry, that they can make themselves pretty, that they can wear different clothes, different colors, different hairstyles. They like being clean and smelling good. And women (and this is a man talking) like the attention of men. They like men who will do anything to please them. They like being looked after. They like being the centre of attention.”

“Hey Professor,” said Liam with a smile. “I’m no expert like you, but that has to be the most sexist shit that I have ever heard.”

“I agree,” said Harry, “but they’re not my words.” He handed some papers, some DVDs of “compulsory viewing” and box with some toys. “Enjoy your girlhood, because a week from now you will be jumping straight into womanhood. Oh, and try not to swear – it’s very unladylike.”

***

When he came to, He could see Professor Hunt beside him. His mind was still fuzzy from the anaesthetic, but he was listening.

“Don’t try to talk Lee,” said Harry. “Your voice-box will not be fully functional for about 2 weeks, as I warned you. We will have to use the slate I mentioned, when you are fully conscious.”

Liam struggled a little and then gave the thumbs up sign. He had experienced the first pain arriving after consciousness, but that only made him think about the $200,000.

“Okay,” said Harry. “So everything was successful and I will run through what we have done. We have remodeled your nose, and I am sure that you will find that it now works as it should. We have reduced your chin, but we have a cast of what it was and we can easily restore it later. We have given you a pair of breasts. Completely reversible. We have fixed your hamstrings, so there should be no discomfort there, provided you avoid athletics. It will mean feet up for over a week. But we can get you back to my place for that. Unfortunately the Achilles problems cannot be fixed without crippling you for an extended period, but we have a solution there. And, as I told you, we have given you those hormone shots.”

It was those injections that had worried Liam, and he had expressed some concern about before the surgery. He had been under the knife before with painful shoulder reconstructions, so he knew about that. This time he felt a little bruised around the face, but otherwise fine. It was the chemical changes to his body that he fretted about. But he had been assured that it was essential to the plan and would not cause any lasting effects provided that it was only for a year. He gave another thumbs up.

“So, we get you home and give you some recovery time before Phase 2. You will not be talking for a while but you have plenty to do learning. We are going to be looking at contrasting male and female movement and expression. It will course time worth credits on your psychology papers, but then you will be putting it into effect. In the meantime you have some new “compulsory viewing.” I want you to introduce you to teenage magazines and ‘the chick flick’”.

Somehow Liam found it hard to raise his thumb a third time.

***

Lee walked briskly down the hall to Professor Hunt’s campus office. She wore wedges will a 3 inch heel, unlike most of her classmates, because that was the solution to the ongoing problems with her Achilles. She had indeed discovered that with heels on there was no pain.

It had only been a few weeks since her hair extensions had been woven in, but she was already adept at styling it is a loose bun on top of her head. And her skill in makeup was also coming along. She had learned that less can be more. Now that her face was fully healed only mascara and a little lipstick was needed over the barest colour on her little nose and her cheeks. For a few days now she had been confident enough to attend classes, presenting herself and Lee Blunt, cute sophomore.

She held her books up to her chest. Her bra felt comfortable, although this was one of the hardest things to get used to. Her breasts filled the cups nicely, and her top displayed a hint of cleavage. Just enough to remain modest. The gaff under her skirt was less easy to wear, but that seemed to have improved too. It was essential. Her skirt was straight, and fairly short, but would betray a penis hanging there, even if the size had reduced recently.

She knocked on his door and received the call to enter.

“Hey there Coach,” she said breezily, her high feminine voice now flowing easily. “I’m just here to cadge a lift home.”

Harry looked at her severely: “I have told you not to call me Coach. Call me Harry.”

“Not here, Harry,” she whispered playfully. “We don’t want the students to know that I am living with Professor Hunt.”

“I do believe you are flirting with me,” Harry remarked.

“Do you like it,” said Lee, lasciviously.

Harry thought for a minute about a response, but found himself smiling at her and saying: “Yeah. Sort of.”

She planted her now well shaped bottom on the edge of his desk and pulled a compact from her shoulder bag to check her makeup. She said: “So when are you finished?”

Harry looked at her. He could smell her perfume in the air. He remarked: “You really are liking this whole girl thing, aren’t you?”

“Well, you told me I had too if I wanted to pull this off,” said Lee. “You told me that I needed to like being a woman to collect my winnings so …, so I like being a woman. Yes. I like it.” With a single manicured finger she stroked her chin while looking in the compact mirror. “I sure like make up better than shaving.”

Soon after the surgery but before the hair salon she had submitted to a “face peel” that had removed all previous imperfections in her skin and seemed to have arrested all hair growth on her face. It was not expected to be that effective, but perhaps combined with the daily hormone dose there was not a sign of a whisker. She was checking now, but was pleased to see that there was nothing. At another time she might have been concerned. She might have been concerned that without a beard she could never go back to being Liam. But not today. Today she had been wolf whistled twice and 3 guys had tried to chat her up. Today she had shared coffee with two other girls and they had complained about men together for a full hour. Today she felt like a woman. Today she did not want to think about going back to a life as Liam.

“Come on then,” said Harry, putting some papers into his carry-case. “Let’s go home.”

There was something about that last word that made Lee feel even better. They were going home. She was going to cook the meal tonight. She was really enjoying cooking these days, although this was still a work-in-progress. They might watch TV together. He had work and she had study which he could help her with, but it would just be time at home. Together.

***

She met him at the door with a huge smile on her face. He instinctively returned it.

“Natasha came round for ballet training this afternoon,” Lee gushed. “This time we spent the whole time dancing in heels. I need to show you before dinner. Pleeease tell me you want to see.”

He had forgotten she had the class, but she did not need to tell him. She was in a leotard and her hair was in a ballerina bun, but she had on a flared skirt and 4 inch black patent leather heels.

He left his papers in the hall and let her lead him by the hand to the area beneath her room where the floor boards were perfect for her weekly dance classes. She showed him to an easy chair and put on some music. The music was modern rather than classical but started with a slow moving piece that allowed her to stretch and present herself. The feet in heels were placed perfectly, but it was the grace of her hand movements that impressed him. He really had not realized how far she had come. She was a big girl, but she moved with a grace that made her appear so much smaller.

Then the music changed. It was Latin-American or something similar. He moves in time with the beat became faster, but she showed the same fluidity. He enjoyed watching her, but clearly not as much as she enjoyed dancing.

When the music finished he found himself applauding. She walked over to him. She was flushed and the moisture between her breasts shone alluringly.

“With my heel problems I never liked dancing in flats,” she said. “Natasha says I am a natural for ballroom and Latin.” She swept her skirt to one side and struck a flamenco pose. Then she added looking at him suggestively: “All I need is a partner.”

“Don’t look at me,” he laughed. “I am hopeless. I can only dance if I don’t have to move my feet.”

She looked a little glum. So he said: “But I think you should do this. We should find you a partner. You are a competitive person Lee. You are doing well with your papers, but you need something other than your studies. Something that is physical and makes you push yourself. Your success on the gridiron shows me that. Maybe you should get serious about dancing. I am no judge, but I think that you are very good.”

She smiled and swiveled her hips looking at him coyly, and she said: “Well thank you, sir.” It was the most girlish thing he had ever seen her do. It seemed to have a strange effect on him. He had to correct himself.

“But you may need to check your back is up to lifting,” he said. “You need to be able to lift your partner in this kind of dance. Even if she is very light, you will need to be up to lifting her.”

“I wasn’t talking about dancing the male role,” she said. He saw the look on her face. She was deeply hurt.

***

“Let me thank you for a wonderful meal,” said Mike. “And let me now tell you that I have identified two of your guests as not being women.” He had a very smug look on his face.

They were the last two in the restaurant having shared the tab and now sharing a glass each of the best cognac on offer.

Mike added: “I am sure that you thought as a trick you would invite two transwomen, one as a ruse to conceal your candidate, and the other, well, your real creature.”

“Go on,” Harry invited.

“Dido,” Mike said. “She was the ruse. Quite clearly a man. And … Pamela, the younger one, she was the bet.” The statement was made with absolute confidence.

Harry said nothing. He continued to sip from his brandy snifter. Mike was infuriated. He asked: “So, have I won the bet? You need to tell me.”

“The year is not up quite yet,” Said Harry flatly.

Mike smiled and drained the last drop from his glass. He wished his old friend a good night and left.

It was raining hard and he hailed a taxi. As one pulled over he could see a woman also waiting on the kerb sheltering under an umbrella. He opened the door for her, surrendering the cab gallantly. She took her seat swinging her legs inside. He could see that she was wearing a sequined cocktail dress and her perfect legs were shown off by black stockings.

The window came down and she spoke to him: “I cannot leave you out in the rain. Are you going far? If we are heading in the same direction we could share?”

“I live in Bewley Heights,” said Mike. “Quite a distance I’m afraid.”

“I am on the way there if you take the 23.”

“I do. That’s my route. If you are sure you don’t mind. I really appreciate it. There seems to be only a few cabs working tonight. Thank you very much.”

He stepped around to the other side and got in.

With the hood of her coat now pulled down he could see that his fellow passenger was very attractive young woman. She was dressed for the evening and impeccably so. Her blond hair was piled up in a complex style and her pretty face was made up exquisitely. Her dainty hands had manicured nails in pink. Her dress was low cut showing impressive breasts. Her long legs below her sparkly dress terminated in patent leather black high heels.

“I am Mike Danes,” he said, offering his hand.

She took it in hers and squeezed it slightly in response. Her smile could melt an iceberg. She said “Geraldine Pettiford. Call me Gerri. It looks like if you are last out, you might have to pay for the ride.”

She was smiling, so he understood it was just humour, but he said. “Seriously, for your saving me from the rain, and allowing me to accompany you for the next half hour, I would be very happy to pay for the entire fare.”

“No, please, it was just a joke,” she said, rustling through her clutch bag for her purse.

Mike held up his hand. “I insist,” he said.

She said: “Well, I always let a man pay for my drinks so why not for my cab?”

“Your clothes tell the story of an evening far more sophisticated than drinks in a bar,” he observed.

“It was a charity function,” she said. “V-day against violence. I was one of several unaccompanied ladies, I am afraid. Some men feel uncomfortable in that environment. Self-conscious about accusatory looks, I guess.”

“It’s a good cause,” he said. “I would have been glad to accompany, had I been given the chance.

***

“I assume that you have invited me over to admit defeat,” said Mike, as he walked in the door. “Those two women at dinner last night. That was your best effort. Not bad, but clearly men.”

“I am sorry to disappoint you,” said Harry. “But I have identification details for both of them in the living room. They are both women. Dido is a little heavy set, but a woman. A mother of two. Pamela is my housekeeper’s younger sister.”

Rather than go into his study, were they usually spent time at his house, he led mike into the living room. They were not alone. There was a woman standing at the window wearing a form fitting dress, her blond curls cascading down her back.

Harry said: “I believe you know Lee, or you might know her as Gerri.”

She turned and Mike knew her. With her hair down and lighter makeup she appeared to him to look even better today than she did last night. The same stirrings he had last night were just about to recur, until he realized.

“No,” he gasped. “That cannot be. You cannot be …”.

Before she could say anything, Harry proudly proclaimed: “Or perhaps you might know him as Liam Sharp, until fairly recently, reserve running back for the Lakes University Timber Wolves.”

Harry looked at her but she was not sharing his pride. She seemed to be … unsettled. There was the beginning of tears in her eyes. Before they could erupt she hurried past them and out of the room. Harry was confused and a little upset. He was thinking: ‘But we’ve won?’

He looked at Mike. He expected him to be pissed, but he was almost white with shock. He had after all, arranged with Gerri to take her to dinner, a week from tonight, at the most expensive restaurant in town. He had been kept awake last night with the fantasy of that date. After dinner of course, in a nearby hotel room he had already reserved in hope, he had pictured himself plunging his penis into her warm and welcoming vagina. A vagina which, he now realized, did not and never had existed.

It took Harry a while to collect his thoughts. Somehow the time was not right to crow about his victory. What about Lee? He found himself rushing after her, leaving Mike to his confusion and total disappointment.

Mike ran up the stairs and knocked on the door of her room, calling out: “Lee, are you okay?”

“Go away”. He heard her voice. Girlish, vulnerable, deeply hurt. “You have your win, now leave me alone.”

“Our win,” he said correcting her. But then he had nothing more to say. Somehow, he knew that pointing out that she was $100,000 richer was not the right thing to do right now. Although despite his qualifications and years of study in human behaviour, he had no idea what was going on.

“Please let me talk to you,” he pleaded. “Let me in. Just for a minute.”

He heard the old lock turned with the heavy key, but as he opened it she had already retreated to the bed. She was sitting there looking at him. Her eyes were still full of tears, and her mascara had run a little, but somehow that served to make her more attractive. Her sensual painted lips quivered in her distress. He suddenly felt what he needed to do. He needed to hold her. But that was difficult with her seated on the bed.

He kneeled in front of her and took her hands. He could feel her hurt. “How could you do this to me?” she sniffed.

“I tried to explain everything that I did. It is all reversible.”

“No it isn’t,” she said. “I am not talking about this. Not my body. Why did you make me into a woman? That is not reversible. Don’t look at me – listen to me. I am not a man anymore.

Harry was listening, and looking too, into her tear-filled eyes. He stood up, lifting her hands so that she should stand too. Without her shoes on, angrily kicked into a corner, and even being well above average female height, she was shorter than him. She seemed small and helpless, and so pretty. There was only one thing to do. The look that she was giving him demanded it. He kissed her, softly but deeply. His hands were in her luxuriant blonde hair, and her hands were caressing his back. And their tongues were embracing. And their bodies hungry for more.

When their lips parted she sniffed: “And why did you make me fall in love with you? What I am supposed to do now?”

He pushed some hair away from her face, now flushed with passion. The tears had stopped. He wondered by what miracle this beautiful creature could be in love with him.

“It was not deliberate,” he said, “But I am glad it happened.”

“$200,000 happy?” she accused.

“Mutual love happy,” he replied. “I have just this moment realized it. I kissed you because I love you too. Can you believe it?”

She threw her arms around his neck. “Oh Harry. I do believe it.”

After a prolonged embrace he said: “But I suppose that we should go downstairs and collect our winnings.”

“Can we spend some of it on the final surgery?” she asked. “I want this to be forever. I want to be a real woman,” she said. “I want to be your woman. If that is possible?”

“That my darling,” said Harry, “is more than possible. To me, it is essential.”

The End

© Maryanne Peters 2020