Free Fiction Friday: The Sorority Sissy (WIP)

Sorry that this is a bit late, my computer is on the fritz right now, and for some reason I can only get blogger to load in Google Chrome. Something is broken with Firefox.

Anyway, today's story is an old Work-in-Progress that I abandoned last year, about a young male college student accidentally trapped in a Sorority during the beginning of Hell Week, and mistakenly being forced to pledge the Sorority as a female.

I ended up rewriting the whole story, adding two additional cross-dressed characters to add a sense of competition, which became Pledge Week Revenge: SISSY MAKEOVER. 

As a WIP, this tale is unfinished, and actually ends rather abruptly. I've recently considering giving this one another go, as I had a lot of it planned out and some of the ideas still sound pretty fun to play with.

Anyway, the story is about 3,000 words long, and after the break.

- Tabitha Kohls

Sorority Sissy

by Tabitha Kohls

Copyright 2014

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Jesse walked with his girlfriend Anita to the end of Sorority Row. She started to say goodnight, but he cut her off with an unexpected kiss. She resisted for only a heartbeat and then kissed him back, their lips locking for seemingly forever under the moonlit sky.

When he broke the kiss, Jesse was happy to see that Anita was left stunned. Now was his chance.

"How about you show me your room, Anita," Jesse said. It wasn't really a question.

Anita opened her eyes, smiling softly. She blinked, and replied, "What? My room?"

She suddenly seemed to snap out of her reverie, and shook her head. "I don't think that would be a good idea, Jess. If the others found out..."

Jesse rolled his eyes, and snorted. "How are they going to find out? The sorority house is right over there, just take me in the back way and show me your room."

Anita looked nervous, and turned to look back at the Epsilon Zeta House behind her. The front yard of the large sorority was filled with cars. She felt a pang of worry. "Maybe some other time, but not tonight, Jess. This is pledge night."

Jesse cocked an eyebrow, suddenly curious. "Pledge night?"

Anita nodded, not taking her eyes off the long row of cars. "We had three girls graduate last semester, so we're having pledges over tonight to fill in the open slots. The more senior sisters will be running the pledges through our... hazing rituals, and then choosing the top three as our newest members."

Jesse noticed that the upper floor windows of the sorority house were all dark. Only the lower front windows glowed with light.

"Looks to me like tonight is the perfect chance to sneak me in, without anyone seeing. The other sorority chicks must all be busy with the new pledges downstairs."

Anita started to argue, but stopped and chewed on her lip, reconsidering his point.

Jesse smiled as he saw Anita chew her lower lip; it was a tell of hers. He knew she'd do what he wanted, he just had to wait.

Sure enough, after only a moment Anita turned back and said, "Okay, but only for a few minutes, alright? If I get caught sneaking a boy into the sorority, they'll kick me out!"

"Just five minutes, babe, I promise." Jesse lied, showing her his best Cheshire grin.

As Anita led him behind the expansive sorority house, Jesse could help but congratulate himself. He had worried that his hold over his slightly older girlfriend was waning, but clearly he still had it.

Anita was only a few months older than Jesse, but she'd graduated high school the previous year. She was now a college sophomore, while he was just beginning his freshman year. The whole campus was still a mystery to him, while she knew her way around with ease. It was slightly humiliating to him, to be led around by his girlfriend.

To make matters worse, Anita had gotten a late growth spurt since she entered college. She'd always been a bit taller than his own rather short five-foot six height, but now she practically towered over him. He hadn't dared ask her how tall she was now, but figured she must have reached at least five-foot ten. And that was not counting her three inch heels!

The tall auburn girl reached the sorority back door, and carefully unlocked it. The door squeaked open, making her wince in the moonlight. She peered inside the darkness beyond, and snuck inside.

"Okay, the coast is clear. Come on, Jess! Let's hurry!" Her voice said, coming from the dark back room. Jesse nodded, and slipped inside, beginning to feel excited. He was sneaking into the Epsilon Zeta house! It was like a dream come true! All of his wildest college fantasies rolled into one!

The back door had opened onto a lower landing of a winding staircase, and Anita all but dragged him along, pulling him up two flights and down a nearly pitch-black hallway until they reached a door. She unlocked the door, and pulled him inside.

He stood in shock, realizing he was in her actual room, at long last!

"So, is it everything you imagined?" Anita teased, plopping down onto her bed. Jesse spun around, grinning widely.

The walls of Anita's sorority room were pastel pink, with an eggshell white ceiling, and dark cherry floorboards. Most of her simple furniture was no different than the stuff he had found in his new dorm room earlier that week, but he still felt a momentary exhilaration just knowing that her dresser was packed full of her sorority dresses, skirts, and especially, her underwear!

He'd spent many nights in high school visiting her room, but he'd never gotten a real chance to be alone with her in it. Anita's parents were far too protective to risk leaving him and their daughter alone in the house for long. But now, now he was alone with her, in her sorority room and half a State away from either of their parents! He flushed red with sudden lust and excitement.

"Well, someone's excited to be here," Anita said, holding a hand over her mouth to keep from giggling. She stared straight at the rapidly expanding tent in Jesse's tight jeans, even as her boyfriend grimaced with discomfort.

Without asking, he started to unbuckle his pants. Anita stopped giggling instantly, and cried out, "What are you doing?!"

Jesse shrugged, still trying to pull his pants off. "What does it look like? These damn jeans are pinching my cock, so I'm taking them off."

"You can't undress in here!" Anita cried, jumping up from her bed and grabbing desperately for his pants.

Jesse pulled back, just keeping out of her long reach. He laughed at her sudden fear, making her face burn with anger. "Dammit Jesse, this isn't a game! If the others find a naked boy in here--"

They both stopped dead in their tracks as they heard a scream from somewhere in the sorority house.

"What the hell was that?!" Jesse exclaimed, dropping his pants around his ankles. Anita shook her head, and carefully opened her door a crack. The hallway outside was no longer dark, but fully lit up.

Jesse started to try to stop her, but jumped away as several woman ran past the door. As fun as it was to annoy Anita, he didn't actually want to get caught in the sorority, especially pantsless!

To his shock, Anita turned to him and said, "Hold on just a sec, Jess. I'll find out what's going on."

Before he could argue with her, Anita had slipped through the door, running after the passing sorority girls. Jesse fumbled with his pants and began fighting his erection as he tried to refasten the thick jeans. Just as he finally got the brass button to slip in place, pinching his hard cock painfully, Anita returned.

Jesse started to yell at her for leaving him, but the look of terror on her face stopped him cold. He swallowed deeply, and managed to whisper, "What's wrong?"

Anita ran her hands through her long auburn locks of hair, looking horribly distraught.

"Th-there has been a break-in. Some frat just pulled off a panty raid."

Jesse sighed with relief. "A panty raid? Well that's not so bad then."

Anita stared at him, her face flushing with anger at his obliviousness. "Dammit Jesse! My sisters have called campus security! They're going to search the whole house, room by room. For hiding boys!"

Jesse's blood ran cold. "Y-you have to get me out of here!"

Anita threw her hands up, in exasperation. "How, Jess? How? Do you want to jump out a window? They're already locking down the house!"

Jesse actually considered jumping from the second story window for a second, but dismissed the idea just as quickly. The last thing he needed was a broken leg.

"Well, you have to do something. If they catch me in here, I could get expelled!" He whined.

Anita rolled her eyes. "What the hell do you think will happen to me, Jess? You think I don't know we're in trouble?!"

Jesse was starting to panic, frantically looking around the room, as if hoping to find some magical exit that would solve his problems.

His tall girlfriend sighed, and dropped back onto her bed, causing a pile of folded clothes to spill off her pillow and over the floor. She sighed again, and started to pick the clean clothes up, when she suddenly got an idea.

She looked up at Jesse, who was starting to pry the window open, clearing reconsidering her earlier suggestion. She nearly laughed, as she asked, "Jesse, what are your measurements?"

The strange question threw Jesse for a loop, and he instantly stopped pushing the window open. "What? My measurements? I don't know, why?"

"Because I have an idea," Anita said. "Not a great idea, but better than jumping from the window."

Anita quickly explained her idea, and as she expected, Jesse balked.

"No, hell no! I am not dressing like a girl!"

***

"Why do I have to wear your panties too? Can't I just wear my own underwear?" Jesse said, his voice coming out as a whine.

Anita stopped her work on his face for a second, and stepped back. She said, "Because I don't have any pants that will fit you, and if you wear one of my skirts over your boxers, someone will notice. Now quit distracting me, we don't have long before my sisters search my room, and I haven't finished your makeup..."

Anita let her words hang ominously in the air for a second, until Jesse slumped his shoulders in silent agreement. Smiling to herself, Anita began working on dolling up her boyfriend's face again.

He'd have been livid if he knew just how much fun she was having, she knew. She'd never had a little sister to play with before. Of course, if he knew she was thinking of her short boyfriend as her 'little' sister, he'd have probably attacked her.

Anita smirked ruefully at that thought. As if he could take me. I've got at least four inches on him.

The tall auburn-haired sorority girl skillfully slid her mascara applicator along the edge of her boyfriend's lower eyelid. She was working quickly, but Anita was well practiced with applying her own makeup, and she thought that Jesse was turning out pretty well.

"Now a little blush," She said, quickly adding a light dusting of reddish powder to his cheeks. Jesse rolled his eyes, but didn't argue. After a minute of carefully blending the powder into his natural skin tone, Anita stood back again and said, "Okay, all done!"

Jesse hopped off the bed, and nearly twisted an ankle on his new high heels. "Ow! Dammit, do I have to wear heel too?!"

Anita shrugged. "They're only two-inches, Jess. I don't have anything shorter than that."

As Jesse sighed and looked himself over in the full-length mirror on her wall, Anita silently wondered why she had lied to him. She had several pairs of perfectly fine sneakers in her closet. But for some reason, deep down, she just had to see Jesse in heels.

Though she couldn't help but notice that she had chosen a shorter pair. She told herself that was because Jesse couldn't handle anything higher, and that was probably true, but only partly the real reason she had chosen such a short pair of heels. The real reason, she knew, was that she liked having Jesse look up at her. She couldn't really explain it, but ever since he had arrived at the university, she had gotten a little thrill to discover just how much larger she was than him.

Not that she'd ever tell him any of that, of course.

"So, what do you think?" Anita asked. Jesse just stood before the mirror, silently shaking his head in a weird mixture of horror and awe.

Anita had dressed Jesse in one of her more conservative skirts. It nearly reached the tops of his knees. Nearly. The skirt was a plaid pattern of reds, browns, and greens, looking like it had come from some Catholic schoolgirl's uniform.

Besides the skirt, he wore a simple t-shirt for a top, as nothing she owned would really fit him, and he had flatly refused to wear a blouse. Under the top, two small bumps pushed out, creating the illusion of breasts.

Jesse was glaring at his reflection, straight at his chest when he finally answered her. "I don't see why I have to wear a bra, Anita. Plenty of chicks are flat-chested."

Anita sighed. She'd already wasted several precious minutes arguing with him to get him to wear her old sports bra. It was tight across his narrow chest, and was now stuffed full of two thick woolen socks.

"I already told you, it makes you look more like a girl, than a guy in drag. We need you to look as far from your normal self as possible, otherwise the others will realize you aren't a real girl."

Jesse scowled at her, but seemed to accept her explanation. But inside, Anita was realizing that the bra and its tiny false breasts were truly unnecessary. No one looking at Jesse would ever think he was anything but a real girl.

He had been on the swim team all through high school, and was now on a sports scholarship to swim on the university team too. All those years of swimming had left him a lean young man, lacking the weight and thick cords of muscle the football players always developed. Jesse wasn't weak by any means, but his muscles lacked definition, giving his arms, legs, and belly a smooth appearance.

And best of all, he had almost no body hair! For years Jesse had been shaving his legs, arms, and arm pits. He'd read somewhere that professional swimmers shaved to reduce drag in the water, and his competition times had greatly improved once he too started shaving.

It was, Anita reflected, one of the reasons they had started dating in the first place. She had liked his smooth skin, his hairless body. Jesse was nothing like the big ugly football players, or even the taller basketball players at school. He never smelt of sweat, wasn't covered in ugly thick mats of greasy body hair, didn't look like he was on steroids.

Thankfully, Jesse had never taken his shaving routine all the way; his head was covered in a thick mass of light brown hair. Jesse was proud of his hair, Anita knew, and liked to wear it long, for a boy.

In fact, his hair was just long enough for her to pull into two short pig tails, each tied with a little pink-and-white ribbon. Jesse glowered at his new hairstyle. "I look like a freak! No one is going to fall for this, Anita!"

Jesse's voice was becoming whiny again. Anita sighed, becoming annoyed that her boyfriend didn't appreciate just what a spectacular job she had done transforming him into a passable female.

"I think it looks cute, and nobody is going to take a second glance at you, Jesse."

Jesse opened his mouth to retort, but was interrupted by a loud knocking on Anita's door. Anita nearly jumped out of her skin, and quickly flung the door open. A very severe looking brunette stood in the doorway, decked out all in sorority colors.

"H-hello Ashlynn," Anita said. Jesse swallowed hard; he knew that name, Anita had mentioned it often enough. Ashlynn Martin, President of the Epsilon Zeta Sorority.

She was a bit shorter than Anita, but still stood several inches over Jesse. In contrast to Anita's modest C-cups, Ashlynn had very large, full breasts. Jesse had to fight the urge to stare right at them, so tightly packed into a much too small bra...

"Hello Anita," Ashlynn said, without any affection. She turned her brilliant blue eyes to Jesse, her expression one of suspicion. "And who is this? One of your little lesbo friends, is it? She's pretty, I'll give you that."

Ashlynn's insinuation that Anita was a lesbian brought her blood to a boil. She and Ashlynn had never seen eye to eye, ever since she joined the sorority. Ashlynn constantly made cruel japes about her, always subtly accusing her of being into women, trying to drive a wedge between her and the other sorority girls.

Anita felt her face flush red with anger, and caught the tiny smirk forming on Ashlynn's lips. Without really thinking, Anita responded, "S-she's just one of the pledges. She wanted to see what our rooms look like, that's all."

Ashlynn blinked, and so did Anita. She hadn't meant to say that, she'd planned on claiming Jesse as a visiting cousin or something along those lines.

But Ashlynn slowly nodded, seeming to buy her explanation. "Okay, fine. Well, pledge, you've seen the room, now get downstairs and line up with the other hopefuls. We're about to begin, now that the campus cops have arrived."

Jesse's mouth fell open; he stared at Anita, but she just shrugged. This wasn't part of the plan; he was supposed to spend the night in Anita's room, and leave early the next morning when everyone was still asleep.

"What are you waiting for, pledge?! Get moving, now!" Ashlynn's commanding voice hit him like a hammer, and Jesse stumbled out into the hall, precariously balancing on his new heels.

***

The hallway ran the length of the second floor, both sides festooned with doors leading to other girl's bedrooms. The stairs he and Anita had taken were on one end, another set of stairs must have been on the opposite end, he thought.

As he walked his way carefully down the hall, he could hear sounds coming from the lower floor. He followed the sounds to the center of the long hallway, and found another flight of stairs, this one clearly the house's primary staircase. It was much wider than the emergency stairs he'd taken earlier in the night.

Gulping, Jesse carefully walked down the stairs and into the lower floor.

The main staircase ended in a large meeting room, with dominated the sorority's lower floor. As he slowly stepped down, one hand holding the wooden banister in a death grip, he saw a sight that took his breath away.

Three dozen girls stood in three lines along the wood floor, each one hotter than the last. The pledges, he realized suddenly. Several other girls, wearing sorority colors like Ashlynn, stood around the room watching the pledges. Anita had said something about only the most senior members of the sorority attending Pledge Night, he thought.

A hand dropped down on his shoulder, making him jump and nearly lose his balance. He felt two lips brush his ears and heard Ashlynn's voice whisper, "Pledge, if you don't get down there and get in line, I'll have the girls blister your ass raw."

Jesse's eyes widened as he suddenly saw that each of the senior sorority girls were holding wooden paddles, each with multiple holes drilled through them. He gulped, and stepped off the staircase.

The other pledges gave him odd looks as he slowly walked to the end of the first line of girls, and took his place. He expected them to start pointing and crying out, "It's a boy!!", but no one did. Rather, they seemed to be giving him angry looks. One girl in particular was outright glowering at him.

They must think I'm more competition! Jesse realized, shocked.

Ignoring the angry glances, he looked around the large room, and was happy to see that he had accidentally placed himself less than fifteen feet from the front doors! He'd just wait till everyone was distracted with this stupid Pledge Night business, then slip away while no one was looking. He'd be home free.

He tore his gaze away from the door before anyone noticed, and saw that Ashlynn was striding across the room, seeming to be coming straight at him!

For another heart stopping moment, Jesse was certain that the angry looking Sorority President had finally seen through his disguise. But Ashlynn walked just past him, and stopped.

Jesse turned around, along with the three dozen pledges, and saw that Ashlynn had stopped before a huge black woman, wearing a police uniform.

No, he corrected himself, she was wearing a campus security uniform, solid black with little brass buttons. The woman was a giant though, a true Amazon. She was full figured, and held a long black club in one hand and smacked it down into her other palm with a loud crack.

Jesse felt a shiver run up his spine each time she smacked her hand. It sounded painful, and he didn't even want to imagine being on the wrong side of that huge, angry woman.

"We've searched the whole house, and it doesn't look like any of the boys are still hiding in here." Ashlynn said.

The black woman's voice boomed in reply. "Good. We ran a few of those little shits 'cross campus. Any idea which frat broke in?"

Ashlynn shrugged, causing her big breasts to wobble. "They weren't wearing frat colors, probably knew how much trouble they'd be in."

The campus cop nodded, smacking her hand again. "Well, we'll be keeping patrols running around the house tonight, just in case. If there is a frat boy still hiding in here, and he tries to leave, we'll catch him. If I get him first, I'll stick my stun gun up his ass and pull the trigger."

So saying, the huge woman moved with all the speed of a jaguar, pulling a large, black, metal cylinder from her belt. She pushed a button on the base, and a wicked blue arc of electricity shot out of the metal prongs on the other end, making a loud crackling sound. Jesse gulped heavily.

"I figure I could fry a frat boy's balls with this, no problem." The huge cop said, laughing.

Ashlynn thanked the campus security woman, and escorted her out the front door, then walked back through the throng of pledge.

Once she was standing before the assembled group, Ashlynn spoke in a booming voice, "Greetings, pledges! I must apologize for the delay in getting Pledge Night started. But now the matter is fully in hand, we can finally begin."

* * * * *