Freshman Re-Orientation 6 - Pt. 4

James was in his second class of the day, Domestic Arts, when he realized that Taylor had been his roommate for over a week already and they still hadn’t moved a bed in for her. It wasn’t like they fooled around or anything, but it still seemed odd that the college would allow a young man and woman to share a bed without any kind of questioning or supervision. James liked it, that was certain. Taylor had a sweet, soft scent and she liked to snuggle against his body when they slept. He was both aroused by her and felt intensely connected with her. It didn’t help that she liked wearing clothes that showed off her trim waist and perky tits.

“James,” Miss Holling said, waking him from his daydreaming, “why don’t you come to the front of the class and help me model proper poise.”

“Yes, ma’am,” he replied and made his way quickly to the front of the room.

Like every other instructor, Miss Holling was unnaturally pretty, and made James feel weak and compliant as a result. He discovered he felt a thrill when he did what the teachers told him. His cock would stiffen when they praised him for his quick and correct responses. Being told he was a good boy made him especially happy.

Standing at the head of the room, James was afforded the opportunity to look at his classmates. Many of them ha the same classes together, and so James had seen them from the first day of classes to this, enough day sin between that the changes in them were subtle. Now, seeing them scattered across the seats of the classroom, James realized how girly they looked. Soft and wide-eyed and happy. It sent a shiver of pleasure through him to think he might have the same kind of softness.

“James, it is important to maintain one’s poise, even when distracted. No matter what else is happening, you must keep your focus. Now, stand up straight like I’ve taught you.”

James stood at attention, his chest thrust out ahead of him. He was acutely aware of the fabric brushing against his quite sensitive nipples.

“Now remain still,” Holling ordered. She lifted a heavy textbook from her desk and placed it atop James’s head. She withdrew her hands slowly, ensuring the book was balanced.

“Good boy. Now don’t move. Maintain your focus.”

Now, Holling took something else from her desk. At first James couldn’t see, but then she faced him and James saw she was holding a tube of lipstick. James’s eyes widened, but he did not move. Her words slowed while she uncapped the tube and pressed the very red lipstick to James’s mouth.

“If you can maintain this kind of poise you see in James while something unexpected is happening, you will be able to keep your composure any time. And you ladies will learn that being able to bend with a changing situation is absolutely essential to your classwork. And to your lives. Now purse your lips like you were going to kiss.”

James obeyed and felt the pressure of the lipstsick. The book wavered on his head, but he did not allow it to fall. He felt the thickness of the lipstick as Holling withdrew and surveyed her work.

“See class? James did not lose his composure. Even while I was applying such a pretty shade of lipstick to him.”

Holling carefully lifted the book from his head and returned it to the desk.

“You did very well, James. And your reward is this.”

Holling pressed the tube into his hand.

“I expect you will use it well.”

Taylor was on their shared bed when he returned from class. She gave a squeal of delight when she saw James and his painted lips.

“That’s a pretty shade of red!”

“I need to wash it off,” James said, but his voice was tired.

“Don’t be silly. You look totally beat. Lie down here and let me help you relax.”

James did not argue. Seeing Taylor spring from the bed in her gray leggings and loose white top, loose enough that when she bent low he could see her breasts cradled in her bra, inspired him to acquiesce. They hadn’t fooled around or anything, but they were certainly snuggled close when they went to sleep. James wasn’t much bigger than Taylor, and the two fit together nicely. Sometimes she only wore panties to bed, and he could feel the smoothness of her legs entwined in his. He found it strange that he had never tried to pursue sex with her, but then quickly countered with his desire to please her.

While James spread out on the narrow bed, Taylor climbed atop him, her knees on either side of his chest. Her slender hands pressed into his shoulders and kneaded the muscles bunched there. The rhythmic motions, the relaxing massage… soon, both conspired to lull James into sleep.

Taylor watched over him while he slept. Just as James had before, she noticed the way his face and skin softened. His breasts were budding on his chest. His hair was getting longer at an increased rate; it was shaggy and nearly to his shoulders now. He was making the transition from masculine to feminine in a way that seeme doth agonizingly slow and shockingly fast.

Taylor’s consuming thought was that beneath him, pressed into the mattress, was a male cock for the taking. Even if James was beginning to present as a sissy, he still had that piece of flesh Taylor hungered for. She imagined rolling him ove,r taking him in her mouth, drinking down his delicious cum. But then she felt the flush of shame. Had she become this because of the whims of Slade and Dr. Collins? And here she was inducting another into that tribe of sissies. She thought of herself as a good person, but how could she be if she was aiding Llewellyn in its corruption of ano9ther man?

These thoughts weighing heavily on her, Taylor rolled off James and tucked her body against his, trying her best to ignore how aroused the very nearness of someone with a cock made her.

Their meeting place was a coffee shop a mile from campus. It was inconvenient for most of the student body and too far away for most of the staff who could find their caffeine fixes from a half-dozen closer spots. In this way, it was perfect for a secret meeting between the awakened sissies.

Brina and Dani were there waiting when Brina arrived and was quickly informed Carrie and Gabi were at home in the event Brina and Dani were discovered and taken by Slade and the faculty of Llewellyn.

“If we were to-“ Brina paused, swallowing. “If we were to be taken back and lose ourselves again, there would still be someone to help us get free again. You know better than anyone how hard it is to think for yourself once Slade’s words are in your head.”

It didn’t take long for Taylor to catch the others up on James and his progress through the program. Just that morning, he showed Taylor the lipstick he’d been awarded in class. When he asked if it would be weird for him to wear it to class, Taylor unthinkingly urged him to do it. She felt guilt over that now, but at the time she had been excited to help him embrace his femininity. Was it because she enjoyed it so much or because she was programmed to enjoy it? Such a distinction as meaningless, she supposed.

“We need to start building some evidence, and that means documentation,” Brina said.

“Tell him to start keeping a journal,” Dani instructed. “That way when we extract him he’ll have a written record of everything they’ve done to him.”

“He’s sinking fast,” Taylor warned. “I think he’ll be dressing soon.”

She squirmed in her chair, turned on by the idea that James was so close to becoming his feminine form. Brina seemed not to notice. She looked out the window of the coffee shop and sat quietly.

“I know how difficult this is,” she said, finally turning her attention back to Taylor. Taylor was made very aware of the weight of her sissyclit, engorged and straining against her panties. She wanted to kiss Brina and to feel the gorgeous sissy kiss her. “I know how easy it is to let your sissy mind think for you. I want to remind you that you can live however you want when all this is over. If you want to stay femme, stay femme. But let it be your choice.”

“I appreciate it. And, yeah, I feel like I’m horny all the time. Like I can’t help myself.”

“Stay strong. Remember that you are doing this for you, for us, for James. For everyone Slade and Collings have caught in their web. Lives that they’ve stolen.”

“I will,” she promised.

At the time, it felt like she meant it. But how long, she wondered, could she resist her body’s insistence on mindless pleasure?

Morning was always busy on the floor. Just before the first classes started for the day, there would be the sounds of girls making their way to and from the bathroom and showers, the pipes complaining in the walls, and the smell of soap and perfume and femininity.

James was at the mirror in their shared room, lipstick turning his lips from pale pink to deep red. Taylor didn’t want to be the one to encourage the young man to fix his hair in a more feminine way, but the accelerated growth made it messy and unkempt. If it were straight, the rich strawberry blonde hair burning under the light, James would almost be passing as a girl already.

“How do I look?” James asked, turning and spreading his arms for inspection.

How would she answer that? Should she tell him that his body was melting into the softer curves of a woman? That his lips looked full and lovely and enticing? That his breasts were pushing out the top of his tee and he’d need a bra soon?

“You look great. You’ll be a hit in class.”

“Thanks!” he beamed, shrugging his shoulders in a girlish way.

“Before you go, one quick request.”

“Yes?”

James was close, and the softness of his skin made Taylor want to reach out and touch him. If she did, she knew she wouldn’t be able to stop. She reached behind her and produced a composition notebook.

“I want you to have this. You’re going through a lot of changes recently, and it’s important you remember the journey. So just a few sentences every day. Things that happened in class. Interesting thoughts you have about your new life at college.”

James appeared confused, but then looked up to see Taylor fixing him with her gaze. His face visibly softened when he looked at Taylor. He took the notebook excitedly from her hands.

“I will, I promise!”

It was true girlish glee he expressed, and Taylor believed she knew the root of it. Part of her programming was to defer to women. James didn’t know Taylor was a sissy. Thanks to the work of Slade and the college, she was not only passable, she was drop-dead gorgeous. When James looked at her, what he saw was a woman, and that meant a superior. Being treated like something more than a sissy made her stomach roll. Taylor wasn’t sure if her negative reaction was part of her programming or merely being a natural submissive.

There was also an underlying arousal. If she fixated on how sissified and submissive James was becoming, she felt real pleasure. Her ass tingled and her sissyclit stirred. Actual erections were a thing of the past for Taylor.

As long as she was Taylor.

“See you after class,” James beamed and waved at her with the gifted notebook.

“Yeah. See you.”