He did not want to be here.
James held the acceptance letter in his hand as he stood in front of the school. It was a large, old building. The kind he saw in TV shows and in movies, built with large gray blocks with gargoyles perched on the roof. The place was intimidating. He shifted nervously from foot to foot as he unfolded the letter once again. He read the details and folded it once more.
Congratulations James,
We are happy to accept you into Femme University on a full scholarship. Your mother made a compelling case and we are pleased to know we have her full support. For the next three years, you will undergo a rigorous and extensive educational curriculum in support of your own personal development. We look forward to seeing you in the fall.
Your initial course schedule and uniform will follow.
Femme University
James looked down at his so-called uniform. Black mary janes, white thigh high cotton socks. A plaid skirt, white girls blouse and a tie. If that wasn’t embarrassing enough, he knew he had on white panties and a training bar underneath. At that moment a breeze lifted his skirt up slightly and he pressed his hands down to keep from being exposed right there on the steps of the school. He felt so vulnerable, standing there dressed in girl clothes. Even though he seemed to be one of many.
He was still shocked at how quickly it had all happened. He had been a bit of a jerk in high school, he knew that much. Didn’t study like he should have and never thought about what his future might be. But when it came time to graduate, he had nowhere to go. But the most important part was that he got drunk at a party and crashed his mother’s car. The police were called and the judge was all set to crack down on him. Hard. That was when his mother suggested a compromise that would keep him out of jail and even get him a job. He thought that sounded like a great idea … until he heard the specifics. That he would spend three years in a school designed to take men and make them more feminine. He had heard of Femme University, but had always thought it was an urban legend, something that the guys in the locker room would joke about. But it turned out to be real, a public-private partnership between the government and private charities to help soften the harder edges of society and stop men from becoming criminals and repeat offenders before they could start. And now he was standing right in front of it. He nearly jumped out of his skin when he heard a voice behind him.
“Hi, you must be James. Pleased to meet you.”
He turned to see a woman who looked just a few years older than him. She wore the same uniform he did, but she filed it out in all the right places.She was the same height as him, and had thicker thighs framed by an incredibly short version of his skirt that barely covered a plump, rounded ass. Her long red hair fell over her shoulders and she had dimples in her cheeks as she smiled. She was perhaps the cutest girl he had ever met.
He realized he was staring at her breasts, which were straining against the buttons on her shirt. “Uh…” no words came out.
She giggled and extended her hand. “I’m Penny, and I’m supposed to be your senior partner for your first year.” He took her hand and she shook it once. “We’re going to have so much fun together!” She practically beamed at him. Then she looked him up and down and smirked. “Your skirt is way too long. That’s going to earn you some spankings for sure.” She winked at him. “If that’s what you’re going for then mad respect girl.:
James blushed and shook his head. “I just thought that I, I didn’t know that—” But Penny waved him off.
“You don’t need to explain yourself to me. We can talk more about it when I give you your bedtime spanking.”
James blinked. “My what?”
But Penny had apparently moved on. “Is that your class schedule? Let me see.” She reached out and plucked the letter out of James’ hand before he could protest. She unfolded it and looked at the bottom. “Let’s see, you have Ms. Havenworth for makeup and fashion. She’s good, you’ll love her. A bit generous with the cane but that's no big deal.” Penny blew a stray hair out of her face and continued on, ignorant of James’ distress. “And you have Home Ec with Mrs. Evans, that will be good you’ll love it.” Then her eyes widened. “You took chastity as your elective? In your first semester? You wild thing you.” And with one hand, she casually whipped up her skirt and James saw a small penis encased in a chastity cage.
Penny was a boy.
She flipped her skirt down. “I took it again my senior year, but most of us girls try to avoid it for as long as possible.” She looked at the letter again. “Oh, and Anal, that’s surprising. Do you have any experience?”
James shook his head. He couldn’t even make eye contact with her now. Was this what he was going to become? She .. he looked so feminine. So soft and round.
“It seems you have one class missing, so we will have to get that sorted out before classes start I think.” Penny reached out and pulled him in for a hug. “But that’s what I’m here for. Oh we are going to have so much fun.”
James could only shake his head as Penny led him up the steps of Femme University.
“Do you want to keep the name James, I was thinking maybe we keep the name but just spell it Jamie? With an i and an e? Or maybe just an I. Like Jami? What do you think?”
But James had no idea what to think. He didn’t say a word as Penny ushered him into the school alongside all the other boys that would spend the next three years being feminized beyond their wildest imagination. Penny seemed to take it all in stride.
“Don’t worry James, I’m going to take very good care of you,” Penny said. “By the time I’m done, there won’t be any trace of masculinity left, I can promise you that.”
She slapped him on the butt.
“Now let’s go find your dorm so you can meet your roommates.”
Holy thud! This kid is likely to be his/her class "sissy".
More stories!!
Would be good to hear the elective options. Secretarial?😈