This story is a work of fiction which is inspired by a masculine lesbian I attended school with. Writing this story has brought back some fond memories. Donations are important to the sustainability of nifty.org; returning to this website is an indication you enjoy reading the stories. Please try to send a donation. If you like this story, please email me at alternativereality783@gmail.com and let me know.
Human sexuality can be a great mystery to some. Some people figure it out at an early age, whereas others are never quite sure. This story centers around one person who is best classified as questioning throughout his teen years.
Coming of age in the nineties in small town USA was quite different than it is today. For one thing, if you were not a heterosexual, you were not permitted to attend high school dances with your partner. This story is a prime example of that mindset.
Jeremy Jacuzzi was the prettiest boy in his senior class. Jeremy had one bad character flaw: He was very self-conscious and was low in self- esteem. To compound these issues, he came from a very strict family. In the eighth grade Jeremy and his mother had a conversation concerning his interest in girls,
Mother: Jeremy, do have a girlfriend??
Jeremy: No.
Mother: Is there someone you like?
Jeremy: Doris from church.
Mother: What do you like about her?
Jeremy: The way she is (she was full figured and about sixteen or seventeen years of age).
Mother: Boy, you are too young to think about that.
Despite being the prettiest boy in class, Jeremy did not have much going for him. He did not excel in athletics, academics, was very timid, and was prone to procrastination. He seldom had a girlfriend because he was afraid to ask one to spend time with her. AS a result, he spent most of his time with male heterosexual friends. He did enjoy gym class and really looked forward to taking a shower. He got to look at all the cocks and tried to match them according to body type. He preferred to hang out with males and his sexual orientation would be best classified as questioning.
Jeremy would occasionally sit on the bus with Lucy, a very friendly girl.
He would get a very stiff erection, but did not proceed the matter any further.
He discovered early on in life that certain things would give him an erection.
He was somewhat a masochist and also would get an erection over seemingly inconsequential happenings.
One such time he was reading a western comic book when an older man hit this young cowboy. did he ever get a hard on; he definitely loved pain.
He also would pre-cum in his pants quite often.
Jeremy was acquainted with a lesbian couple in school. Their names were Leslie Lesbonaire and Dreama Delicious. Leslie was very masculine and Dreama was very feminine. He was not real acquainted with Leslie, but he was with Dreama.
Jeremy was set to graduate in a couple of months and the senior prom was coming up. Leslie and Drema were not permitted to attend the prom as a couple. They both wanted to attend the prom, so Leslie concocted a scheme so they could attend. They would agree to disagree and end the relationship so they could attend the prom with others. Before they separated, they would have a parting kiss on Saturday evening. Leslie and Drema got together at Dreama's house. Dreama's parents always went shopping on Saturday night. And what a kiss it was. As they were in the 69 position, Leslie stuck two fingers up Dreama's ass until she squealed with delight. She then stuck a big dido in Drema's pussy until she had an orgasm.
Now for Leslie's escort to the prom: Drema told Jeremy that Leslie wanted to go to the prom with him, but he needed to ask her. He asked Leslie to go to the prom with him and she happily accepted. Jeremy's mother was happy too; she was afraid he would shame their conservative family by announcing he was gay. Poor Jeremy, he has no idea what he has gotten himself into.
Jeremy's mother rented him a nice tuxedo, while Leslie's father bought her a very modest evening gown. Leslie being very masculine did not want to expose her breasts, but she could not wait to get her hands on Jeremy's ass. She had her one fine bitch and she was going to fuck his brains out after the prom.
In the days preceding the prom, Jeremy and Leslie practiced acting as a couple. They began by holding hands, and finally he was allowed to kiss her. The first time he kissed her was on the cheek; gradually he got the nerve to kiss her on the lips and finally he French kissed her. Leslie noticed every day that Jeremy's pants had a wet spot. She had a mean streak to her; One day at lunchtime, they went to a secluded spot and began to French kiss Jeremy. With her right hand supporting Jeremy's head, her left hand began rubbing his dick until he shot the whole load in his pants. Jeremy had to spend the rest of the day in cum soaked pants.
The week of the prom, Leslie decided to explain to Jeremy the proper way to clean his rectum. She said, "This is knowns as the double finger fuck method". In reality, she did not want to get shit on her dildo when she ass fucked him. On Friday at lunch time she gave him a genuine French kiss and told him I will see you about 4:00.
On the day of the prom, Jeremy washed and waxed his car and then took a bath. He made sure his rectum was clean, shaved and shampooed. He put on his tuxedo and drove to Leslie's house. The Lesbonaire family was very gracious and invited Jeremy to stop by for a visit. He then took Leslie to meet his parents. After another photo shoot, He took Leslie to a fancy restaurant where they had a table reserved for them. Many of the female guests stopped by to speak to Jeremy and Leslie. They were a nice looking couple, especially since Leslie had a facial for the prom.
When they got to the prom, Jeremy and Leslie greeted their friends before settling in at a discrete area. Leslie gazed into Jeremy's eyes and they held hands. Leslie made sure they appeared to be a genuine couple. They ate refreshments, and danced the night away. Jeremy was a good dancer, due to the fact that his parents had sent him to dancing lessons the last couple of months. After the prom was over, the happy couple went for their private celebration.
Jeremy had the keys to a cabin that a family friend owned. Jeremy carried Leslie into the cabin. The couple French kissed and Leslie began to undress Jeremy. As she laid Jeremy back on the bed, she began to lick his nipples. She then kisses and sucked on his neck until he had a hickie. She was wanting everyone to know that she owned Jeremy. She then began to suck Jeremy's dick but already decided that she would not swallow. For her to swallow would be an admission that she was being submissive to a man. No self-respecting lesbian would do that, so when it came time for Jeremy to cum, she jacked him off. After giving Jeremy a few minutes to recuperate, she spread her legs while Jeremy sucked on her breasts, ate her pussy and licked her ass. She was squealing like a pig by the time Jeremy got done with her. Leslie told Jeremy she loved him. She probably did not love him, but that was a ploy to get what she wanted. She then told Jeremy he was a naughty boy and told him to sit on her lap. She then turned Jeremy across her lap, spanked him and stuck her finger up his ass. It was Jeremy's turn to squeal; she then lubed her dildo up, fucked Jeremy in the ass until semen was dripping out his cock. After this they had a serious conversation.
Leslie: Jeremy do you love me?
Jeremy: Yes, I do!
Leslie: Prove it.
Jeremy: How?
Leslie: Be my little sissybitch.
Jeremy: What is that?
Leslie: Let me feminize you.
Jeremy did not know what to say.