Freshman Re-Orientation 6: Pt. 6

The next update will be the full story. Hope you're enjoying it!

Seeing James laid out, bared and beautiful in his burgeoning femininity, it took all of Taylor’s reserve to keep focused on her task. It helped, she knew, that the obedience to Slade’s wishes kept her hands steady.

She removed a pair of sheer pink panties from her side of the wardrobe’s bottom drawers, where all manner of lacy and delicious lingerie was stored, and stretched the waist between her hands. Kneeling by James’s feet, she threaded his legs into them, easing the women’s underwear up his smooth legs until they were snug against his small sissyclit. She saw him stirring, but his lids remained closed. She was assured that he would be still for her until she began her ministrations. Slade had seen to that. The panties fit well over his swollen hips. The fabric was translucent enough for Taylor to make out his cock and the tuft of fur surrounding it beneath. Now that he was properly dressed, Taylor climbed onto the bed beside him, even with his body.

Her hand rested on his withered cock, outside the panties. She gathered the material and surrounded his shaft, holding the sheer, slick material against his sensitive skin. Only once she had gripped him, the panties serving as a satiny barrier between the flesh of her hand and that of James’s sissyclit, did she begin stroking him. He rose quickly to attention, a thin erection that nonetheless stirred Taylor’s own loins. Once he was hard, she found a teasing pace. James began to squirm on the bed, his arms lifting over his head. Taylor could see the way his new breasts shifted on his torso, and how his nipples had tightened into tan nubs against his creamy flesh. The fan of his red-blonde hair spread about his head, and his tongue ran over his full lips.

“What are you doing?” he mumbled, eyes fluttering open.

“Showing you how sexy it is to be in panties,” she giggled, her strokes never ceasing, never varying the steady rhythm.

“What?” he said, cloudy and confused. He looked down to see her hand working his cock, his penis enshrouded in the sheer panties.

“Just lie back and enjoy it, James. Feel how goo dit is to have your cock in panties. How nice it feels against your skin. I bet you almost want to cum already.”

The words came from Taylor unbidden. They were the words of Slade, she knew,w ords that had been left inside her mind, the lid of the container that held them opened when certain criteria were met. Like james squirming on the bed, his legs kicking atop the covers, his hands finding his breasts and cupping, squeezing.

“You’ve been thinking about wearing pretty panties already. It’s okay. You should. You look se sexy in them. And they make you feel sexy, too. See how hard you are? Being in panties is the sexiest thing you can imagine. Wearing pretty girly clothes that show off your sexy sissy body.”

James groaned and lifted his hips, matching the strokes with the motion of his pelvis, fucking Taylor’s hand while she held him. She coaxed him deeper into his lustful haze with every brush and squeeze, hurrying her hand, urging his climax on. He was panting, clawing at the bed.

Taylor could see the schism in his mind, the fracturing of his male persona and the sissy programming that fought to take hold. His body betrayed him, his desire equated with femininity and weakness.

“Go on, sissy,” Taylor whispered, “cum for me and feel how good it is to be what you were meant to be.”

With that simple urging, James’s back arched and he squirted his seed into the panties, soaking them with his sticky seed. The sheer panties could not contain it all, and Taylor found her hand coated with the sweet-smelling semen. She swirled a finger around his panty-clad tip and gathered a fat drop.

“Open wide,” she urged.

He obeyed. A finger slipped into his mouth and he closed his lips on it, the first taste of cum filling his mouth rightfully his own. He sucked her finger until it was clean and withdrew his head, collapsing back onto the bed with a long moan.

“I know,” Taylor giggled. “It feels like everything changes all at once. But you did so good. You are super sexy, James. You want to clean up and really see how girly you can get?”

He blinked, slow and stupid.

“Yes, please.”

Taylor helped him wash his cock, again resisting her natural urge to take him in his mouth. She’d stolen a few tastes of his cum while she cleaned him, shivering when her tongue tasted the slaty, oily goodness of it. The panties she used to jerk him off were soiled, so she helped him change into a pair that were clean, but no less pink and silky.

“I think we might need some support here, too,” she said, pinching both of James’s taut nipples at once. He gasped and let out a pleased sound.

“I have boobies,” he said, as if the thought had just occurred to him.

“You do,” Taylor agreed, finding a bra with a smaller cup size than the ones she wore.

These had been given to her for just this occasion, and fit James well, cupping his small breasts. With his panties and bra in place, he looked exquisitely girlish. Taylor guided him to the mirror of the half-bath and stood him before it.

“Let’s make all the boys in your class jealous,” she grinned from behind him, and uncapped the jar of foundation on the sink counter.

The work to make him feminine was easy. The hormones and drugs he was being fed in his hypnotic sessions was doing a miraculous job of that. The makeup Taylor applied enhanced and refined his feminization. His lips were lined, then made glossy. His eyes were shadowed, and the lids dusted. His cheeks were highlighted by subtle rouge. When Taylor was finished, little of the James that existed before was left.

He blinked, seeing himself in total after the transformation was complete. His eyes blinked slowly and a smile crept across his features. With his head tilted downward and that mischievous expression playing across his features, he looked like the very picture of sissy seduction.

“How do you feel?” Taylor asked.

“Perfect,” he purred in a voice that had little trace of boyhood left.

Going to class in full makeup would have been completely ludicrous only a few days before. Sashaying across campus now, though, panties under his jeans and a simple bra under his hoodie, he felt like the girlish version of himself was bursting through his masculine façade. It did feel to James as if his truest self was hidden beneath the remains of masculinity, that this new version of himself would soon consume what had existed before. He wiled away the time it took him to cross campus by playing a scene between himself and his parents, explaining to them that this was the new James. They paid him little attention before, so why would they care now?

His first class was his Fashion Arts class. Miss Wiley was always the very picture of female beauty. She was in her mid-30s if he had to guess, but dressed as if she was going to a nice party after class. She was never without heels or a dress, her hair was never less than perfect. When James entered, he saw that she was in a form-fitting green dress with dark stockings and heels, silver jewelry highlighting the deep verdant color of the outfit. She exclaimed with glee upon seeing him and rushed to James before he could find his seat.

“Look at your face! You look so pretty!” she exclaimed.

James felt a mix of pride and sheepishness spread through the middle of him. And not a little arousal. Being complemented for being ‘pretty’ stirred something inside him.

“Thank you, Miss Wiley,” he said, his head lowering automatically.

“Have a seat, pretty thing, and we’ll get started.”

As he took his seat, James saw that he was not the only one who wore makeup today. More than half the class was expressing its femininity now. James took his usual place in the second row while Wiley took roll and then paced in the front of the room, elegant motion in heels. She silently observed the boys in class and tapped her chin, pausing in the middle of the room.

“I don’t want to make anyone uncomfortable, but I have seen some changes in you boys. When I look at you know, I hardly see boys at all. What I see are a bunch of sissies. Look at you in your makeup. Why, I bet some of you are even wearing girls’ panties. Am I right?”

There were some murmurs, but the answer was largely found in the way the boys looked askance rather than meet their teacher’s eye.

“James, do you know what a sissy is?”

He did. He had been called sissy off and on most fo his life. Even though he had never evidenced any signs of femininity, he was smaller than the other boys, and his skin was soft and smooth while the other boys developed their first patchy growths of hair on cheeks and chins. It was a word used to humiliate him, to make him feel like less than a man. Somehow, though, when Wiley used it, it sounded like less of an insult and more… truth? Inevitability?

“Yes, ma’am,” he answered, his voice soft.

“I think you probably know what you think it means,” the stylish woman fired back, “but you, all of you, likely think of it as a negative. That’s not true. A sissy isn’t a real man, obviously, but that doesn’t mean a sissy doesn’t have a place in the world. Sissies can be so sexy and helpful. By looking sexier than some girls, they can lure a boy and make him feel better than he’s ever felt. And they are always quick to help a real woman. They are sweet and silly and sexy and fun. That sounds nice, doesn’t it?”

She aimed the question at James, and he nodded his head.

“And I don’t think the name ‘James’ fits you anymore. Would you like a sexier, more girly name?”

“Yes, please,” he said in that adopted sotto voce.

Wiley tapped her finger on her chin, looking over the boy. Her lip were pursed, and James couldn’t help but focus on the deep red varnish coating her nail a sit ticked against her soft chin.

“I think Gemma,” she announced. “It’s sweet and sexy and playful, just like you. What do you think, Gemma?”

Itr felt like he was crossing a line in his head and putting everything that had come before behind him. His old life, his struggles to fit in, his conflicts with his parents, none of that mattered. He had never been a successful boy. But he felt accomplished in his new role as a sissy, even if he hadn’t given name to it yet. He thrust his growing chest out and smiled.

“I love it, Miss Wiley.”

“I knew you would. Head back to your desk and we’ll see how the others feel.”

Gemma sat at her desk and waited patiently while Wiley moved up and down each row, first quizzing each of the boys on their sissy-hood, and then declaring a new name for them. None wavered and none protested. What had begun as a class of boys ended in a classroom full of self-described sissies, eager to explore their newfound femininity. And to that end, Wiley conducted a fashion seminar in the last half of the class, helping ach to decide what clothes might best be suited to their new life.

Gemma was made the poster girl for this effort. When she left class, gone were the jeans and hoodie she entered with. She left in a loose sweater and tight leggings and sueded, fur-lined ankle boots that lifted her and gave her ass a pronounced wiggle. Her strawberry hair was loose and down and straight. Wiley added a pair of fashion frames to enhance the difference between James and Gemma, though by this point, Gemma thought very seldom of James.

Before she exited the class, lost in the swirl of fledgling sissies eager to express these new personas, Wiley took him by the shoulder.

“Miss Collings needs to see you. Will you head to the Nurse’s Office?”

“Yes, ma’am,” Gemma replied, unsure of exactly where that might be. But when faced with a woman as imposing as Miss Wiley, she couldn’t quite bring herself to ask for directions or ask follow-up questions, like why she should have to go to the nurse in the first place.

Likewise, it was difficult for Gemma to feel comfortable asking one of the girls on campus. They all seemed so much stronger, so powerful, in comparison to Gemma. So it was one of the boys she asked. The moment he stopped to answer and gave her body a lingering examination, Gemma knew she had done the right thing. Having a boy look at her like a sexual object was making her sissyclit hum and tingle. She bit her lip seductively while he pointed the way to the Nurse’s Office, and the two glanced back at each when they parted – the boy to get a better look and Gemma to ensure that the cute guy was looking at her ass, as he should.

The Nurse’s Office was in a science building Gemma had never entered before. Fortunately, the room was close o the entrance and was marked by another sissy waiting outside. The two shared a nod and a smile before a third sissy exited the office. The cute sissy who had been waiting outside was called in and Gemma took the seat she left behind, awaiting her turn. She couyldn’t quite place why she flet happy to be waiting in the hallway like that, when delays had always frustrated her back when she had been a boy, but it was hardly worth thinking about the old self when this new one was so much more fun and satisfying.

It didn’t take long for the seat’s former occupant to emerge from the office, and for Collings’s head to pop out.

“Gemma,” she said with a smile, “come in. Just a little shot.”

It never occurred to Gemma that her new name had been used, nor did she question what shot she might be given. She obeyed, as all good sissies did.