Freshman Re-Orientation 6 - Pt. 3

“Fine. Be sure to thank both of them before you’re done, though.”

“Yes, ma’am,” Taylor said, already mounting the stairs that led to the girls’ rooms. “I won’t forget!”

She knew Jackie’s room, having cleaned it many times before. Taylor navigated the hall in her tall heels and flattened her dress, which was already clinging to her body, before she took a nervous breath and rapped delicately against Jackie’s door.

“Who is it?” the sorority girl called through the door.

Taylor heard the sound of a man, too, the voice muffled by the door. It sounded like he was teasing Jackie, though. And there was a low chuckle, enough bass that it rattled Taylor right down to her shrunken clit. It rarely gained its former rigidity. She shivered, the memory of the man she had been crashing through her thoughts, a stone shattering the image of her sissy reality. She saw Brina and the others, girls that didn’t look all that different from her. Sissies who were boys before. Like Taylor.

“Well?”

“Oh, sorry, it’s Taylor, ma’am. Becky said you wanted to see me?”

More laughter shared between Jackie and her hidden boyfriend. The door opened and Jackie filled it, leaning on it while it swung open, a girl-next-door vision with her curly dark hair and cutoff jeans. She had great legs and knew it. Taylor was a little jealous. That flame of envy grew hotter when she saw Jackie’s man.

He was handsome in a bland sort of way. Generic good jawline, generic shag of hair, generic scrub of beard. His shirt was unbuttoned and Taylor saw his toned body beneath, curly blonde hairs decorating the expanse of his chest. She immediately wanted to feel them threading through her fingers. His jeans were faded and he wore tan work boots. He was sitting at the edge of Jackie’s bed, arms propped behind him to support him.

“I thought you said you were going to bring some dude up,” he said, eyeing Taylor with one part confusion and one part lustful curiosity.

“I said a boy. Does this look like a dude to you?” Jackie laughed and took a hit from a THC vape she pulled from her front pocket. She exhaled and fell onto the bed beside her guy, reaching up to hand him the vape pen.

“It definitely doesn’t.” He took a hit for himself. His eyes never left Taylor.

Whatever thoughts of Brina and the young man Taylor had once been existed, they were shredded by the look of Jackie curling around her boyfriend, his leering making pinpricks of pleasure dance along Taylor’s spine. In turn, she eyed the bulge in the young man’s jeans. She could make out the barest hint of the outline of his cock. It made her stupid with desire for it.

“Besides, Taylor is barely even a boy anymore. He’s a sissy. Aren’t you, slut?”

“Yes, ma’am.”

“Did Becky tell you about our little problem with Reg here?”

“Yes, ma’am,” Taylor answered. “She said he was finishing too fast. That maybe I should take that first load off your hands.”

Jackie cackled and rolled onto her back, kicking her legs up in the air.

“You are such a fucking whore!”

“Yes, ma’am,” Taylor said, a cheeky grin tugging up the corners of her mouth.

“Well, go on, then,” Jackie said with a grand wave of one hand while she took a fresh hit of the vape with the other. “Reg, give our sissy some dick.”

While Reg unbuckled his belt and spread the fly of his jeans, Taylor took her position between his legs. She was transfixed by the sight of the white briefs revealed when Reg unzipped his jeans. She had never experienced a cock this close before besides her own limp excuse for one, and she approached it with something like worship. She nestled between Reg’s thighs and helped him shuffle the denim down his thighs. Taylor was salivating. She knew what awaited inside the white cotton, could se eit straining to be free.

When reg reached for his dick to free it, he was interrupted by the eager sissy between his legs, already tugging down the waist of the briefs. His cock sprang free, bobbing in front of Taylor’s face. She gasped when she saw it, and part of her brain lit up with its programming. Her hand slid around Reg’s staff and she lazily stroked it. She treated his cock like it was some rare and endangered species, coddling it, examining it, looking upon it with reverence.

She held him and closed her eyes, descending while her muth parted. She felt a twinge of something – shame? disgust? – as his round tip slipped between her lips and her body relaxed around it. The whole universe was Reg’s cock and she orbited it with her tongue, taking him deep in her mouth.

“That’s a good slut,” Jacke cheered, “take him all.”

Taylor did. She felt him strike the back of her throat and she released a hollowed, deep sound that wasn’t quite a gag. Her head rocked on his hard member, forcing him to the op of her throat, stroking his shaft while she blew him. Reg reached forward and gathered her hair in his hands, guiding her pace. First, he slowed her. Then he was pulling her face against him, filling her mouth with his veiny rod, using her mouth like the cumhole it was. And Taylor adored it. He rbrain was quiet of all rational thought. All that echoed in her programmed brain was ‘Good girl’ over and over. Her body hummed with use.

“Oh fuck,” he groaned.

Taylor felt him tense, felt the orgasm gathering like a thunderstorm building, the moment right before the rain began and the lightning raged. Taylor lost herself in that moment, when she was fulfilling her sole purpose: to serve and suck cock.

He pulled out before he came. She felt him spasm in her mouth and then he withdrew. Taylor opened her eyes in time to see the wad coming at her, to snap her eyes shut again as the ropey line of semen spille dover the ridge of her nose and began its snail-paced march down her cheeks. Another squirt on her right cheek and another, smaller load deposited at the base of her throat where it trickled down toward the valley between her breasts. She licked her lips and tasted his tangy cum there. She shuddered with pleasure.

“That’s all,” Jackie said, dismissing Taylor with a wave. “Oh, and no cleaning his cum off you until I say so or one of the sister stells you. Understand, slut?”

“Yes, ma’am.”

“Good. Now get out of here. I want some alone time with my man.”

As Taylor left, Jackie was sliding on top of Reg, who looked after Taylor as she exited the room. She felt a secret thrill that Jackie’s man was still looking at her. Cum cooled on her face and chest as she carefully descended the stairs.

Many of the other sisters of Kappa Rho were seated on the mismatched couches and chairs of the common room. The cum painting Taylor’s face and chest shone under the lights, leading to catcalls and shouted humiliations. Taylor heard it, but none of it dented the haze surrounding her. She was floating on air. A sissy having been put to good use and now wandered back to her downstairs room consumed by lust for more. Her asshole tingled with need to be plunged and pillaged.

There were no thoughts of Brina or a boy named Tyler.

When James was called to Miss Slade’s office, he was sure it was about his schedule. For two weeks he’d been attending classes that were filled with boys, but every bit of the class material was aimed squarely at girls. And not just any girls. Whether it was learning how to cook in Home Ec, not to mention all the emphasis on navigating a kitchen in high heels, or the Fashion Arts class where he was informed which color went best with his complexion, it all felt like something straight out of the 1950s. Women were docile and pretty and eager to please according to his lessons.

The strangest part was how much he was growing to enjoy it. He looked forward to his classes, now. Some of the other boys, James included, were becoming friendly and enjoyed giggling together like gossipy schoolgirls. When they were excessively chatty, Miss Prader, she of the Domestic Engineering class, would even refer to them that way.

“Alright, ladies,” she would say, sending them into a new fit of giggles, “time to concentrate. You need to learn if you’re ever going to be of use to anyone.”

That was another recurring theme of his lessons. Being of use. Such language led James to look back over the course of his young life and ask himself that very question. At what point had he been of any use to anyone? Perhaps his old running-around gang, the ones who had protected him. But they had to protect him because he was weak. It was a difficult thing to admit certain truths to yourself he was discovering. One of those truths was that he was weak.

A second truth, one that had not formed fully in his thoughts yet, was that James enjoyed feeling feminine. Whenever the thought rose, he quickly stuffed it back into his subconscious, but that didn’t mean it had no effect. He didn’t think about it, but his gait had a little more wiggle in it, his voice was landing in a higher range these days, and he discovered a newfound appreciation for how weak and silly strong women made him feel.

And that ignored the physical changes that were slowly making themselves known. His hair was growing quickly, already shaggier than it had been on his arrival. Not quite to his shoulders, but the light red hair looked full and lustrous. His skin, too, had softened, and the hair on his legs and belly felt finer under his touch. And surely the itch in his chest and around his nipples was nothing to worry about.

Miss Slade’s office was on the third floor of the liberal arts building. Most of the campus was made up of old homes, quite large homes, repurposed for education. More modern edifices stood scattered among the more quaint, older structures to give Llewelyn College a feel that was both throwback and intrusively modern. James made his way up the stairs, past the two floors used for classes, and to the third, which was dedicated to administrative offices. Miss Slade’s was the last on the left.

Whatever James expected from Slade, he was no prepared for the voluptuous cougar sitting behind the desk. Her hair was dark and curled at the tips, a pair of black-framed glasses balanced on a thin nose, full lips and a body that swelled at the chest. When she stood to shake his hand, he saw that proportion extended to her hips. She had the kind of body you wanted to sink into. James found that from the most moment he met Miss Slade, he knew he wanted to please her.

“Have a seat. It’s nice to met you finally.”

They both sat, a cherry oak desk between them. James noticed he could see Slade’s heels beneath the desk, black and polished, and he tried not to let the glint of their toes distract him.

“I understand there has been a mixup with your classes. I want to assure you were are working that out.” Slade leaned forward to look at the computer monitor perched at an angle on her desk. “I have to say, you are doing quite well int hose classes. If we don’t get the schedule straightened out before the end of the semester, at least you’ll have a heck of a GPA.”

James hadn’t considered he might have these girl-centric classes all the way through the semester. He found the idea was ot without some appeal. He did like them. And Slade was correct – he was doing very well. He was distracted from these thoughts again by the glint off Slade’s heel. She was rocking one of them beneath the desk, and sunlight from the window bounced off the sharp tip of the shoe. He blinked when he realized Slad had spoken again.

“I’m sorry?”

“I was saying that you’re going to be assigned a roommate. I know how uncomfortable it must be to be on a girls’ hallway in the dorms, but I’m sure it has its advantages, too.”

She gave him a sly smile that suggested she knew how boys were. Oddly, James had not felt particularly horny around all these undeniably cute girls on the hall. He was starting to feel at home with them, and did not want to do anything that might make them feel uncomfortable.

Not that he was complaining exactly, but why did Slade have to keep rocking her heel like that? The regular rhythm of the light winking on the tip of it was so distracting. He found it difficult not to stare at it, to measure the breath in between the peaks of the shoe’s swing, the light’s regular pattern. And Slade was talking. He was trying to focus on her words, but it was so hard when the glint off the black patent leather kept drawing his eye. And still Slade talked. Her voice was lower, now. She spoke with a pace that made him feel very sleepy and his eyes drooped along with the rest of him. His arms hung loose over the arms of the chair. He felt so incredibly relaxed, like all the bones in his body softened and melted. The only thing that remained steady was his focus on Slade’s light-catching heel and the sound of her voice, like warm water washing over his thoughts.

Slade snapped her fingers and James jerked to attention. He swiped at his mouth and discovered he was drooling from one corner. He felt a rush of embarrassment at how he must appear to the gorgeous administrator.

“I’m sorry,” he said quickly, straightening.

“Don’t be. We had a very productive meeting, I think. Now why don’ you scurry back to your dorm? I bet your new roommate can’t wait to meet you.”

“Uh, yes, ma’am,” he stammered.

He gave a little wave as he left, feeling awkward and silly. Slade wore a knowing half-smile that both aroused and worried him, a feeling that quickly evaporated as he descended the stairs. His head was swimming. Had he fallen asleep? He must have. He had the same dopey feeling he did when he took an unexpected nap and his thoughts still felt messy and heavy, unable to follow a complete line of thought. He embraced that hazy feeling as he stepped into the Autumn sunshine, the air crisp and pleasantly cool, the leaves drifting from the trees scattered across the campus in lazy drifts. A peace enveloped him, a feeling that he was exactly where he needed to be and doing exactly what he should.

He had all but forgotten about his new roommate until he opened the door of his room and found a cute blonde flitting around, placing her clothes in the standing closet. When she sa whim enter, her face split into a grin and she rushed at him, wrapping her arms around him and pressing her slender body against his.

“Hey, I’m Taylor,” she sang. “I hope you don’t mind that I started putting some clothes away. They said they have to get another bed for the room. I told them we could share your tonight. I hope you don’t mind.”

“What? No. That’s fine.”

He blinked. He was trying to think through the fog and process the fact that this sexy girl would be sharing his bed.

“That’s what I said. We are going to be really good friends. I can feel it.”