Chapter 12

Tim found himself staring at the two girls beside him as they made their way across campus, the same ones he hated himself for being attracted to after everything they had put him through. No matter how much he wanted to deny it, the feelings rose up anyway, and that only made him despise himself more. The contrast between their outfits alone made him stand out, for people to look at. At any moment he was afraid someone was going to ask why he was crossdressing or yell out some slur. The two coeds were dressed so much more casually showing off their personal styles, while the style he currently possessed had nothing to do with who he really was.

Emily looked sharp in her fitted pink button-up, the mock-rolled sleeves fixed neatly with crisp white cuffs. Her tight jean skirt cut off two inches above the knee, casual yet flattering, and the plain white sneakers gave her a relaxed but commanding air. She carried herself like a woman who never had to try for attention; it simply followed her.

Sarah offered a softer kind of beauty. Her blue high-collared blouse with puffed cap sleeves peeked from beneath a red tank that buttoned neatly across her chest. A dark brown pleated skirt with two tiers fell just past her knees, paired with calf-high leather boots that gave her a steady, practical presence. She looked approachable, even warm… she had been much nicer to him, but that hadn’t changed what she was forcing him to do.

Then there was him… Tammy, dressed for her date with someone he didn’t have the name for yet, other than knowing it was someone here at college. The tight red dress hugged in ways that felt more exposing than flattering, yet it showed off the feminine curves created in his thin frame by the taut corset beneath. Pantyhose clung to his legs with a sheen that made him think everyone was going to look with every shift of his body, every step he took in the four inch high heels. That wasn’t even counting how much makeup they had put on him compared to what they were currently wearing. Standing beside Emily and Sarah, he did not feel like one of them. He felt like a doll… a puppet that had to do as they commanded, he only hoped that he really did look as much of a girl as he saw in the mirror. It had been painful in its own way to see the reflection of Tammy looking back at him, the makeup doing such a great job of making her eyes pop, his hazel eyes looking alluring in a way he wasn’t comfortable with.

The two putting on the outfits had been an experience that both demeaned and exhilarated him, a memory that lingered in his mind like a haunting secret. They had undressed in front of him with an ease that denied his maleness entirely, as if he were no more than another girl in the room, a silent observer to their intimate ritual. Emily, with her tall, lean frame, stood confidently as she peeled off her clothes, revealing her smooth, pale skin. Her dirty blonde hair, cut in an uneven bob, framed her face, and her brown eyes sparkled with a mix of mischief and amusement. She was a vision of confidence and allure as far as he was concerned and the fact that she was so well aware of his lingering gaze and acted like he didn’t matter did things to his mind as his body had its own reaction as her body a testament to her vitality. Her breasts, full and round, swayed slightly as she moved, and her hips, narrow and toned, accentuated her long, slender legs.

While Sarah acted more hesitant as she undressed and left parts of herself covered, the act of disrobing in front of the hormonally charged teen boy had grabbed hold of his attention just as strongly as her taller roommate. Her petite frame, standing at a mere five foot three, was a stark contrast to Emily's towering five foot ten. Her long, brown hair cascaded down her back, framing her delicate features. Her blue eyes, wide and innocent, met his with a mix of curiosity and a bit of shyness of her own that only deepened the need he felt growing. She was a picture of innocence and vulnerability, her body a testament to her the kindness she shared with everyone around her. Her breasts, small and perky, smaller than Emily’s but like any boy he liked them all the same. As she undressed, her movements were hesitant, her eyes darting to his, a half-smirk playing on her lips, a look that promised something more, something he couldn't quite place.

The sight of their bare skin, revealed so casually, pushed them in his mind from simply pretty to almost painfully hot. His stomach knotted with shame. They had treated him like just another girl, stripping without concern, and that indifference only deepened the sting. Emily had moved just as boldly now as before but in a new way he hadn’t expected, while Sarah had taken her time, more hesitant, and that half-smirk she gave him still burned in his thoughts. He could not decide if it was teasing or something else, but it left him rattled, caught between humiliation and a stirring he did not want to name.

It had been minutes since Sarah’s hands had been sliding up his now smooth legs as she slid the nylon fabric up, and thoughts of it returned with a flush of heat. That weakness of his body reacting on its own, much to his shame now haunted him. There was nothing he could do about what they were doing, what they were making him do, nor his physical reaction to it.

Tim gave his head a small shake, feeling the loose sway of his blonde hair as its slightly wavy curls brushed against his cheeks. The movement dragged him back into the present, away from the lingering memory of Emily and Sarah undressing in front of him. The sharp click of his heels on the pavement filled his ears, each step sounding too loud, the footwear he was **** to wear looked wonderful on a girl, but the sounds they made as he walked made him know he was just calling out for people to look in his direction.

‘What do people see? A boy… fuck I’m not even a man, just a crossdressing boy. Will they see that or would they pay more attention to the tits on my chest that look too much like the real thing thanks to the addition of makeup.’ The strapless bra he wore eased some of the weight from the glued on breast forms, but their pull was still there, a constant reminder of the curves **** upon him. All while the pantyhose added another layer of strangeness, the nylons wrapped around him brushing with every step as his thighs touched, sending shivers up his spine no matter how hard he tried to ignore it. All while his feet still ached in the four-inch heels, though he was steadier now, his body beginning to adapt. But that steadiness only deepened his shame, each step was carried out with a semi practiced feminine gait, a sway in his hips, a wiggle that Tim was aware drew the male eye, him having admired such a thing on many an occasion, and now it was him moving that way.

The two college coeds walked easily at his sides, the trio taking up the full sidewalk as they moved. Emily’s fitted pink shirt and short denim skirt gave her an effortless style, her white sneakers making Tim feel as if what he wore stood out even more. Sarah’s layered blouse and pleated skirt gave her a softer, more thoughtful appearance, her boots clicking quietly beside him. Both looked natural, each in her own way. Tim, by comparison, felt artificial, **** into a version of femininity that was exaggerated, yet he knew what he saw in the mirror. Tammy appeared to be a pretty young woman, and yet he still couldn’t shake the feeling he was going to be outed for a pretender.

The dressing wearing young man kept his eyes down, convinced that every passerby was staring, that any second someone would shout out that he was a man, or some slur in his direction. The sound of the heels on his feet, the tug of the dress, even the faint touch and scent of makeup seemed to announce what he was. His chest grew tight with panic,causing a line of sweat to run down his compressed body.

At first Tim paid little attention to where they were headed. All his energy was spent on the simple act doing as he had practiced back at the sorority, not even taking a single glance at anyone they passed in fear of it drawing attention in his direction. Sarah telling him to relax, how the only thing anyone would see is a pretty girl, didn’t in fact make him relax at all.

It was only when the path began to feel familiar that unease crept into his chest. The sidewalks, the curve of the road, the shape of the trees—he knew them. Timothy’s breath quickened as he dared a glance up, praying he was wrong. ‘Don’t be here, don’t be here, don’t be…’ the thoughts came to a crashing halt when the street opened ahead, and he found himself exactly where he didn’t want to be. The Omega Omega Kappa house loomed up ahead like a bad omen of what more was to come.

Once the OOKay house had been a place he longed to belong within, a home he thought would make him somebody. Now, dressed as Tammy, paraded forward by the girls at his side, it stood as the cruelest destination imaginable. Each step toward it tightened the knot in his stomach. His humiliation was leading him back to the very doorstep of his own fraternity, closing the circle in the most brutal way possible.

Jake had been sitting on the porch steps with his elbows on his knees, watching the three figures come down the walk. Looking over them he tried to put names to faces. A girl named Emily had been the one who messaged him online, mentioning a friend would be with her, another member of Tri-Sigmas, would be coming by to introduce him to a cute pledge of theirs. How they were doing her a favor by setting her up on a date with him. How she thought he was cute, and a way to bring their houses closer together. Two birds with one stone, was the phrase she had used.

Even so, a tightness sat under his smile. He had sent a pledge of his own to their house… Tim Thompson was sent on a raid to steal panties the day before and the kid never came back, making the timing of things suspect. This all seeming a bit like an attempt at payback, fallout from what happened. Like this Emily was trying to organize a time where she could confront him. Jake could picture some fat cow of a girl reading him the riot act in front of his own house. Wanting to look unbothered by the possibility he kept his posture loose and easy, but watching them now the tension he felt was already starting to ease. None of the three were overweight, pimple faced cows, already making things better than his worst predictions.

Staying in place as they drew close enough he lifted a hand and pointed lightly at the brown eyed girl that had dirty blonde hair in an uneven bob cut. “Emily Donnalds?” He guessed, having a fifty-fifty chance of getting it right before motioning to the petite brunette. “Sarah Johnson?” He wanted to be sure he had it right.

Then his eyes settled on the third girl, examining her even as the two confirmed his guesses. Golden blonde hair with a soft wave, bouncing slightly as she walked. Hazel eyes that seemed glued on him as she came closer, her wearing a tight red dress that hugged her narrow waist. Dark pantyhose covered legs that ended in heels that clicked with each step. As his brown eyes met hers she dipped her chin, glancing away as if she was nervous about being caught staring at him. The way her lashes fluttered as she did made his own uneasy smile become something more genuine. That little hint of her being drawn to him and shy about it made her seem sweet.

The combination of it all loosened wariness enough for it to be washed away. They really had brought a pledge of their own, a pretty little thing that clearly had a crush on him.

While Jake admired the pretty girl being set up on a date with him he had no idea he was reading the situation so wrong. Tim being all nervousness, embarrassment and a strong desire to flee all mistaken for a shy girl who was interested in him.

The tall twenty one year old looked the three over once more, and came to a final decision. ‘So, not a trap, no setup for ****.’ With that last thought he put the over eager pledge out of his mind, assuming he had just chickened out. Standing up he brushed his hands on his jeans before stepping down from the porch with his normal easy smirk in place.

Stepping off the last stair, Jake’s smirk widening as he looked over the three of them. He gave a quick nod to Emily and Sarah, enough to be polite, but his focus slid straight to the blonde girl clutching her small red purse like it was the only thing keeping her upright. “And…” he turned his head slightly, already confirming the two others names, but they had never given him the name of the girl he would be going on a date with. “Could I have your name? I’m Jake, Jake McGraff.” he said in a way James Bond often gave his name in the movies. “But you know who I am, I just haven’t been lucky enough to learn your name yet.”

Tim’s heart pounded hard enough he was sure Jake could hear it. Out of everyone he could have been thrown in front of, Jake was the worst possible person. He kept his head slightly bowed, hazel eyes darting up once before lowering again. His throat tightened as panic clawed at him, his thoughts in a frenzy. ‘Jake is going to… he will… No, no, no! He will see through it all! He knows, how could he not!? Me being a girl is flimsy, it is obvious I’m not…, he will see right through me. If he doesn’t he will… he will… why is he smiling at me? Lucky enough to learn my name? He knows my… No… he couldn’t be buying this. Is he? Shit… okay, okay, just smile, just be Tammy, she is supposed to like him and needs to keep him happy. God, I can’t think about what they put in the purse. Need to just make it through this without dying or letting him figure me out… That being the same as dying, shit okay, okay.’

“Hi,” Tim **** out, his practiced voice catching for just a moment before smoothing into something higher, softer. “I’m Tammy. You can call me Tammy, because that's me, Tammy.” he let out a nervous laugh.

Jake’s grin curved into a lazy chuckle. “Tammy, okay. Just Tammy? One name, huh? I can get that.” His eyes roamed over her face, catching the way she blushed and ducked her head, lashes flicking nervously. To him how she acted was textbook. Tammy was a girl with a crush, trying hard not to make a fool of herself in front of someone she liked.

Tim gripped the strap of his purse tighter, fighting to keep his hands from trembling, every fiber of his being screaming to run. Jake had been someone he once looked up to… he did look up to. They were someone he wanted to impress as a pledge and here he was needing to do the same on a date, while pretending to be a girl. Now the same man was standing close enough to touch him, smiling at him, teasing him, and Tim could barely breathe between the stress and the ever so helpful corset.

Jake noticed none of the panic hidden behind her eyes. All he saw was a pretty blonde in a tight red dress, shy and bashful, and clearly made up just for him. Her coyness only stroked his ego, confirming everything he had already been told about Tammy, that she liked him, that she thought he was cute. In his mind it was easy to picture how it had all happened, a late-night sorority sleepover, Tammy confessing her crush to the other girls, and Emily deciding to step in and play matchmaker by arranging the date.

Jake’s grin lingered as he stood beside her, moving with the easy confidence of someone who expected the world to follow his lead. His arm slid around the blonde’s waist as though it belonged there, the unprompted gesture showing how certain he was. The faint shudder that he felt passing through her body told him everything he wanted to know. The excitement, Tammy practically vibrating with pleasure at his touch. The blush rising in her cheeks sealed it in his mind. She wanted this, she wanted him, and now it was clear to anyone watching that she was his for the night, perhaps longer if he chose.

Tim’s every muscle locked up as an uncontrolled shudder of revulsion ripped through his entire body. The corset kept his back straight and his stomach drawn in, but inside he felt like he might explode. The heat of the older boy’s hand against his side seeped through the thin fabric of the dress, burning into his psyche. When his muscles unlocked instinct betrayed him as his own hand lifted and rested against Jake, a reflex to steady himself. His own move surprised him, yet all he could do was to **** a small smile onto his face, eyes darting to the two girls who had brought him here, pleading silently for help from those who had trapped him in this moment.

Then, before Tim could even think another thought, the brown-haired young man leaned down and brushed a quick kiss against his cheek. The contact was brief, almost playful, but it sent a shock through him all the same. His skin tingled where the lips touched, bringing forth a wave of humiliation that spread like wildfire until his face burned with the deepest blush he had ever known. He wanted to wipe the spot clean, to shove Jake away, to run. Instead, he stood frozen, aware that Emily and Sarah were right there, watching. The knowledge that they were witnessing his first kiss from a non-relative, even if it was just one to his cheek and it coming from another boy made the shame unbearable.

“Thanks for setting me up with such a pretty girl,” Jake said, turning his grin toward Emily and Sarah. His tone full of easy charm, the kind that came naturally to someone who had never doubted his place in the world. “I owe you one. Feels like everybody wins here.”

“I couldn’t agree more, all those that deserve a win are getting one.” Emily smiled back at the cocky frat boy in front of her.

Tim swallowed hard, the words hitting him like another blow. ‘A pretty girl… he really does think I’m pretty.’ he thought, knowing he had a similar opinion on what he saw in the mirror. It was what girls wanted to hear, or so he presumed.

“Have fun together.” Sarah looked between the two in front of her, before focusing in on the tormented boy. “You two make a cute couple.” She beamed, her smile overly large, all while she thought being the one to spend time with the crossdressed boy a year younger than herself, her mind losing track of the point of the setup.

“Right.” Jake nodded, giving his date a gentle push with his hand around them to move away from the little gathering to actually start the date. Hearing the click clack, click clack of Tammy’s heels as they walked he glanced back at the two coeds. “Thanks again, I will make sure we both have a fun night.