Sissy Forever, Part One

A few notes about this story:

Some 35 years ago, when I first began really exploring my fantasies of being a girlish boy, one of the first sources of TV fiction I found was Astounding Transvestite Tales, published by Empathy Press. In an early volume was a story called "Evelyn Manor." I later came across that story again, and realized it had elements that could be reworked into something along the lines of my usual transformation themes.

I've reset the tale in the third person, and all the hypnotic elements are my own. There was no author credited in the ATT publication, but this story is dedicated to that anonymous inspiration.

Mother called to Robert as he opened the door to his bedroom upon returning home from school, “Robert, I would like to speak to you". He entered her room and was surprised to see his Aunt Christine sitting on the edge of his mother's bed. He had not seen his Aunt Christine for over five years.

Mother, his older sister Deborah, and he had visited Aunty when he was eight years old. Robert has never liked her and he knew she did not like Robert as she had made it quite clear she did not like boys. She had a beautiful two-story home located on a large estate.

Deborah had spent every summer since their initial visit, at Aunty’s.

Aunt Christine was a woman of 40, a bit overweight, tall, and very attractive. She had never been married and had at one time been the executive of a fashion advertising firm and had been very successful, this had followed a career of modeling. She had always bestowed many gifts upon Deborah, and Deborah would tease Robert at times, saying, "If you were a girl you could go to Aunty’s for the summer and you would get lots of presents." When Deborah would leave for Aunty’s there were times when Robert would feel jealous, but he knew that if he had gone with her, Aunty would have made him miserable with constant corrections.

Deborah was two years older than Robert--tall, attractive, and possessed a very pretty figure. At 15, she was in her third year in high school. She was always on the honor roll in school, although she worked after school at a women's apparel store as a sales girl and also modeled, Mother was very proud of her. Aunty had been instrumental in Deborah obtaining her job as Aunty was one of the owners of the women's apparel store.

Robert was just 13 and quite the opposite of his sister. They were physically similar, as he was tall and quite slender for a boy, but the similarity ended there. Robert's record in school had always been wanting for improvement. He did not like to study and was constantly getting into trouble with his teachers for teasing the girls and just plain unruly behavior. This pattern of behavior was also evident at home.

Robert's father had passed away when he was four years old and Mother had raised Deborah and Robert from that day to the present. Mother was in her late 30s and similar to Aunty in looks and physical make-up.

Robert had a good idea why mother had called him to her room, as he had been severely reprimanded by both the principal of the school and his teacher. They had made it quite clear that since there were only six weeks to the end of the school year he would not be expelled but Mother would be called and told of his disrespectful attitude and continued bad behavior.

Mother confirmed his suspicions. As she scolded him, she was interrupted by Aunty. Aunt Christine said, "What are we going to do with you? You apparently have no respect for women nor do you have any respect for yourself.

"Your mother and I have discussed several avenues of punishment and have arrived at one that we feel will teach you respect for women, teach you discipline and crush your boyish arrogance," she said. "Tomorrow is Friday and we are going to keep you home from school. When you awaken in the morning you will begin your punishment period. It will last through Saturday, Sunday, and through to Monday morning. I will also warn you that should you not cooperate during this period and should your mother receive any more reports of disagreeable activities from school, this punishment will be repeated each weekend and if necessary you will be invited to spend the summer at my estate with your sister.

"Your punishment will deny to you everything essential to being a boy," she concluded.

As Robert left the room and went to his own, Aunt Christine's words were repeated in his mind. "Your punishment will deny to you everything essential to being a boy."

Once Robert had left, Mother turned to Aunt Christine. "You're certain the program your friend Wanda has given us will work?"

"Absolutely," Aunty replied. "It's well tested by the staff at Evelyn Manor. They send it out as part of their student recruitment system. While the same kind of hypnotic suggestion could be used to simply control the boy, they've found more lasting success in a series of subtle shifts in his personality, all tied to the clothing he wears and the way he looks.

"Believe me, after just one night with these special tapes and one day in the right girls clothes, Robert will be experiencing strange new feelings...and enjoying them."

Mother called Robert again and again he entered her room. Aunty directed him to strip down to his underwear. Being afraid of her, Robert did as he was told.

Mother and Aunty both began taking measurements. When they were through, they told Robert to dress. As he left the room, Mother said that she and Aunty were going shopping and would be home later. When they returned later, they had Deborah with them, as they had picked her up from work.

Deborah said, "We really have a surprise for you, but you have to wait till tomorrow morning."

As he climbed into bed the things Aunty and Deborah said really bothered Robert. "Oh, well, I can handle anything, I'm a big boy."

Mother dropped a tape cassette into his stereo. "What's that?" Robert asked.

"I can tell you're all upset about not knowing what's going to happen tomorrow...and you'll never get to sleep, you're so wound up," she answered. "This is a special 'new age' music tape. It helps to soothe your mind and help you sleep."

Mother pressed the play button and soft, quiet, strings and chimes floated from the speakers. She stepped out of the room. Within a few minutes, Robert felt himself drifting off to sleep, but with the sensation that something more than music was coming from the tape, though he could not really hear anything else.

The subliminal sleep suggestions gradually switched over to more hypnotic suggestions and then came to dominate the sound--and Robert's subconscious mind took in every word.

"When you see your nails painted red, you will feel a stirring in your cock," the tape told him. "You will not recognize what is making you excited, but you will want more of it. Wearing high heels, especially sexy sandals, will have a similar effect. You will also enjoy the sight of your wrists with feminine bracelets on them...and you will think of the bracelets not only as adornments but as slave ornaments, enslaving you to a feminine future.

"You will think of these experiences as 'strange new feelings,' and they will be stronger every time you see yourself in these feminine things."

The tape repeated several times through the night and then shifted back to the "new age" music to let Robert drift into a normal sleep until morning.