Headmistress' Favorite Sport

Headmistress' favorite sport

By 2NN

Authors note:

Be warned: This one is more than a little extreme.

This story should not be shown to, or be read by, minors. It is strictly adult material.

Prologue

The twins Joanna and Jocelyn watched their older brother, Dennis, with contempt. They both thought that he was a complete wimp, a weak little sissy. Being related to the useless creep was embarrassing. Not only was he small and weak, his tiny hands and feet combined with his very fine features made him look more than a little feminine. Furthermore he wasn't exactly the sharpest tool in the shed. If he had been a girl he would have been called an airhead. He was their mother's favorite and she always pampered him at the expense of his kid sisters. Dennis was seventeen and the twins were sixteen but to the casual observer it would seem that the twins were at least nineteen and that Dennis was sixteen at the most. They were much more mature and physically well developed. Both the twins and Dennis went to high school, but whereas the Dennis had yet to have a sexual encounter with anyone but himself, the twins were already experienced man-eaters. Both had several sexual affairs behind them, but most people didn't know just how experienced they were. Not only had they slept with more than one boy, they had also slept with more than one girl. Neither had had anyone you would call either a boy- or a girlfriend, only torrid sexual encounters that left the ones they had had sex with dazed at the intensity of the sex. For that reason they didn't have a reputation for being loose. Whoever they had been in bed with always kept quiet about it. The most well kept secret, which not even Dennis or their mother suspected, the reason neither had a boy- or a girlfriend was that they were lovers. The twins had exactly the same taste in everything and their taste ran more to girls than boys and both thought the other was terribly sexy. So they were lovers. Whenever they were sure no one was looking they kissed or had sex if there was time. Joanna and Jocelyn were partners in everything.

Dennis definitely didn't like the way his sisters were looking at him. They had that special smile on their faces, which told him that he was in for a hard time. Dennis knew that he wasn't the smartest guy in the world and that his sisters were both far superior in both physique and brains, but he was smart enough to recognize that look on Joanna's and Jocelyn's faces. They were up to no good. Dennis had felt inferior to his sisters for most of his life. They had almost always been smarter and stronger, but in recent years the difference had become bigger and bigger. Whereas the twins had grown into young adults, Dennis seemed to remain a teenager. Tiny hands and feet, thin wrists, almost feminine features, practically no facial hair and a very light voice; all branded him as a wimp. He was no good at sports and he struggled with even the simplest things in class. He had no friends and the only person who seemed to love him was his mother. She was terribly concerned at his lack of growth and wanted him to see a doctor about it. Dennis knew that he would go to the doctor eventually, even if he hated the idea, but he also knew that it wouldn't be right away. They were not terribly well off and a visit to the doctor would probably require his mother to ask her sister Rachel for money, and his mother hated that.

Aunt Rachel was very rich. She had made her money first as a stockbroker and since as a venture capitalist and she had been enormously successful. Not even thirty-five she was already retired with enough money to last more than twenty lifetimes, even if she was lavish with it. Rachel had married Tony a huge black guy, much to the dismay of her parents. But now that they were dead no one cared if Tony was black, only that the man was very mysterious. No one but Rachel knew where he came from and more than a few suspected that he had married her for the money.

His own mother, Susanna, was the older of the two. Susanna had had considerably less success. She was thirty-eight now. When she had been nineteen she had married Dennis' and twins' father, Tom. Tom had been a lot like Dennis, small and weak but the two had been happy, if not rich. Neither had any real education and worked odd jobs, Susanna as a waitress and Tom as a cab driver. When Dennis had been seven his father had disappeared. He had seemingly driven his cab to the buss station and taken the first buss out of town. Although no one could remember him buying a ticket or getting on the buss, there was no indication of foul play and everybody believed that he had just had enough and run out on his wife and three kids.

With her husband gone Susanna had to work two jobs to make ends meet. Her younger sister had offered to take all of them in, but Susanna had refused. The two sisters weren't the best of friends and it was only after great persuasion that Rachel convinced Susanna to accept money to pay for the kid's education. The twins had been very disappointed that they weren't going to go live with their aunt. The twins were very fond of their aunt and spent many afternoons and weekends in her company.

Dennis thought of this as he watched his sisters smile ominously at him. Things were not going his way, but he had no idea that things were soon about to get a lot worse. This was the reason for the twins' smiles. They had a pretty good idea of what was going to happen. They spent a lot of time at their aunt's house because they liked their aunt a great deal. She was the only one they knew who was as perverted as they were. Aunt Rachel knew all about their love affairs, including the one they had with each other. She regularly had sex with the twins and she treated them as her natural heirs. Aunt Rachel had hatched a truly evil plan, which would change all of their lives for good. Rachel despised her sister as a useless underachiever and had wanted to get to her for a long time. Rachel had found out just how desperate her sister was financially. If she lost one of her waitressing jobs, she would be unable to pay the rent. Times were hard and there were no other jobs to be found. Rachel had also found out that one of the places Susanna was working was about to go bankrupt.

Rachel wanted the whole family to come live with her so that she could take control and the twins were in on the plan. To make sure that her sister would have no choice but to come live with her, Rachel pulled a few strings. This would result in Susanna losing her other job as well, making sure that she came to live with her sister. Once this happened Rachel would take charge. She had long had a fantasy about turning Susanna into her slave and soon she would do just that. She would turn her older sister into a groveling nymphomaniac slave.

But the truly evil part of the plan had been hatched by the twins. The wanted to turn their brother into a real sissy, a shemale slave. They had already started the preparations and had for more than two years secretly been feeding him female hormones. This was the reason for his weak physique. He hadn't been given enough hormones to grow tits or other outright feminine features, but that was only a question of time. The hormones were very special, not pure female but rather a product that promoted certain feminine traits, while ensuring that some male traits remained or were even enhanced. Dennis for instance, could get an erection. Not only could he get an erection, but also the hormones made him terribly horny all the time. The twins had a camera in his room and reported with glee that he masturbated almost constantly. Dennis thought that the horniness was a normal part of growing up.