Chapter 8

The question posed to him, Tim shuddered as the girl looked at him looking so happy despite the plight of his situation. Was he ready to do even better, the dress wearing teen didn’t want to do better at talking and walking like a girl. Though doing so was his only hope of having a real future. “Sure am, though I’m trying to do better than… better.” he said smiling brightly, though it came across as looking more than a little awkward.

The smile still firmly in place, Sarah turned her head slightly to the side, very much enjoying him playing along with things and not just repeating what she told him to. She wished his smile was something more genuine, she was having so much fun and it would only make it better if he enjoyed it as much as her. Still this was the pervert, even if they were a sort of **** pervert, so she was going to give him a correction when the doorknob to the bedroom clicked and turned.

Tim’s head whipped around, panic rising until Emily stepped back into the room with her usual composed confidence. Her eyes flicked from Sarah, sitting cross legged on the bed, grinning like a proud coach, to Tim, still standing unsteadily near the duct tape line, him smiling though in a way that made it clear how awkward he felt.

“We’re good,” Emily announced with a little wave of her hand. “They’re hanging out downstairs watching some Netflix trash and trying to pick ice cream from the twenty four hour diner. No one’s coming up.” She paused and bobbed her head from left to right slightly. “They might go to bed, but they won't be coming in here, that is the point.”

Exhaling shakily, Tim felt a rush of relief flooding through him, though it was quickly punctured by Sarah speaking up that left him feeling like he was standing on pins and needles despite the truth not being much better with him wearing the girly footwear.

“That is good news…,” she started to say before her own body interrupted her with a long yawn, stretching her arms overhead in a slow, dramatic arc before letting herself fall back onto the bed with a bounce. “I so wanted to keep going.” She said to Emily while physically looking up to the ceiling as she lay on the bed. “I was gonna have Tammy strut down that tape like she was auditioning for a Victoria’s Secret catalog, maybe do a twirl, blow a kiss or two or twelve…”

Emily yawned in reaction to seeing her friend yawn tiredly, double checking that the bedroom door was fully shut. “You can do that tomorrow. I’m beat.”

Sarah sat up slightly, looking toward her friend, half pouting. “Seriously? But we were just getting to the fun part.”

Emily walked past her captive, over to her bed and tossed herself down with a quiet grunt. “We’ve had her playing as our sorority doll for hours, my brain’s fried. She’s fried. You’re hyper and overly tired at the same time. And yet, I don’t trust what you’d make Tammy do if I let you keep going.”

Tim stood frozen, a strange lightness creeping into his chest. ‘Is it over?’ he mentally asked himself, his legs trembling inside the wedge heels, his body aching under the lingering pressure of the corset. His lips still tingled faintly from all the gloss and repetition, and yet, somehow, hope flickered behind his eyes.

“Wait…” he said, voice cautious. “So… are we done?”

Sarah propped herself up wit her arms, sitting up slightly more than before, her smile a little too mischievous. “Aww, does Tammy wanna go home?”

“I…I mean, yeah? Maybe?” He looked between them, unsure whether to feel grateful or braced for another trap.

Emily tiled her head to the side, using one hand to help crack her neck before answering the question. “We’re going to let you get some rest, Tammy. You’ve had a big day, with the pervert coming into this room and you wanting help to be the pretty girl you always were on the inside.” She paused, locking eyes with the blond boy. “But don’t think that means we’re letting you run off into the night.”

Tim’s stomach dropped, his relief premature, his own hope and expectations feeling like a self betrayal. “So I can’t leave?”

Sarah giggled and swung her legs over the edge of the bed. “Silly girl. Of course not.” she answered as if the entire thing had been planned and they weren’t making it up as things went along.

Emily added to it, her own voice firmer.. “We’re not stupid. You think we’re just gonna hand you back your boy clothes and hope you keep your mouth shut? Still, you should be more worried about us keeping our mouths shut.”

Tim shrank slightly at her tone, his hands unconsciously tugging at the hem of the dress that touched his thighs.

“We’ll get you cleaned up,” Emily added with false cheer. “You’ll be much more comfy in your sleepover outfit.”

Sarah clapped lightly, her eyes gleaming. “Slumber partyyyyy!”

Tim felt that same chill crawl up his spine. Whatever break he thought he was getting, it wasn’t freedom. Just a different flavor of the same control.

Emily grimaced, holding two fingers up like she was pinching in the air, a small gab between them. “Tone it down just a little Sarah, I mean…”

Sarah nodded, feeling like a child all over again, tired but too excited to want to go to sleep the night before Christmas.

Emily ran her fingers through her hair with a tired sigh and shifted to the edge of her bed. “Alright, Tammy. Time to get you ready for bed.”

Tim wasn’t sure what they were going to do next and didn’t want to have hope that it would be positive. “Wait…what does that mean?” He took a half-step back, nearly stumbling in the heels once more.

“Exactly what it sounds like,” Emily said with a tired smirk. “You’re not sleeping in that dress. We’re not monsters.”

Sarah clapped once, already hopping off her bed with newfound energy, not that she truly had any to spare after the emotional roller coaster of her evening. “But everything else stays on, of course. I mean, c’mon…Tammy can’t just run around braless.”

“Or un-corseted,” Emily added, standing and walking toward him. “That would ruin your posture, we just started your waist training after all.”

“Wait, no, can’t I just…” The distraught boy’s voice sounded much closer to a whimper.

“Arms up,” Sarah interrupted, grabbing the hem of the wrap dress before he could protest again.

“W-Wait, seriously?!” he exclaimed as it seemed like she was just going to pull the dress up and expose himself in the panties. It wasn’t about modesty, they had put him in them after all, but that didn’t mean he wanted to be left exposed like that again.

“Do you want us to not help you out of this thing?” Emily raised an eyebrow, only just now getting up from her bed, moving much slower than Sarah.

Tim groaned, his cheeks burning with embarrassment as he raised his arms, the hem of the dress sliding up and over his hips, exposing the full view of the pink thong he had tried to steal and now wore and the tight lace of Emily’s bra holding the glued breast forms firm to his chest. The corset wrapped around him from hip to ribs, still perfectly cinched and immovable beneath it all.

The dress came off Sarah tossed it onto her bed casually, while Emily circled him, appraising the outfit underneath. “Not bad. Sleep chic.” she said, it a nonsense sentence she was trying to just mess with the blushing feminized college freshman.

Sarah giggled. “Still gotta do something about that face though. Every girl knows you shouldn’t sleep in your makeup, it is bad for your skin, right Tammy?”

“Yeah…” Timothy answered, not enjoying being referred to as a girl even as he flinched when Sarah approached with a packet of makeup wipes. She gently cupped his chin, tilting his head up as she began to wipe away the layers of blush, powder, and gloss.

“There,” Sarah said with a satisfied grin as she finished. “Bare faced beauty.”

“Not quite done.” Emily held up a bright blue scrunchie in one hand and a yellow one in the other. “Pigtails. She needs the full tween-at-a-sleepover look.”

“I do?” Tim muttered the question, but he didn’t resist as Emily guided him to sit on the edge of the bed and began sectioning off his hair. The soft waves they’d set hours earlier still held shape, and she gathered each side into tight, high pigtails, securing them with a playful tug.

“Awwww,” Sarah cooed, cupping her hands under her chin. “You look adorable. Like… slumber party Barbie with her accessories.”

Tim groaned but didn’t argue. His humiliation felt complete, though he was afraid that despite being at rock bottom he would find out he could go lower.

Emily stepped back and nodded. “Alright, pajamas are on.” she gestured to the oversized Tri Sigma T-shirt Sarah handed him.

He slipped it over his head, the hem falling slightly lower than the dress he had been wearing, giving him an idea that it had belonged to the taller of the two girls. The tightness of the corset underneath caused the shirt to hang awkwardly, highlighting the fake but very visible curves of his chest and cinched waist, making it appear that he had a natural feminine form.

“Perfect,” Sarah said brightly. “Now grab your blanket, Tammy. We’ve got the perfect spot picked out for you.”

Emily knelt down between the two beds and started moving aside a laundry basket and an empty duffel bag, clearing a small patch of floor. “Alright Tammy,” she said, patting the carpet like she was inviting a dog to sit. “Here’s your little nest for the night.”

Tim stared at the space in disbelief. “Okay…” he didn’t argue, he had a bed, well a bunkbed at the frat but still had to sleep on the floor the other night as part of their week. So at least it wouldn’t be worse… or at least it wouldn’t if he was wearing his normal clothing. Telling others that he slept with some sorority girls would earn him some cred, but only if let out a great deal of information.

Sarah tossed a thin blanket into his arms when he hadn’t taken it when she offered, followed by a pillow that barely looked fuller than a couch cushion. “What? You’re lucky we didn’t stick you in the hallway. Besides, think of it like a campout! With your two new besties.”

“Wish that was actually true…” Tim muttered to himself, the idea of having two girls be his friends at college would be nice, real nice, even give him a chance to hook up with them or one of their friends they set him up with… heck just having besties… best friends would be a step up, but that wasn’t actually happening at all. Clutching the blanket he looked down at the cleared spot between their beds. His sides still ached from the rigid corset, that it being there, but from just how tightly it had been pulled, his feet throbbed in the shoes he’d been **** to wear, as they **** his feet to stay at an angle he was not used to. ‘Its fine… just wait till they fall a sleep and I can slip out. Take off the shoes and then make a run for it, no, no. Slow steady movements, don’t want to wake them up. Will they call the police in the morning? Wait, where are my clothes? I need to get my wallet so that way they can’t prove it was me.’ Fragments of a plan ran through his mind as he tried to think his way out of the situation that he had gotten himself into.

“Ready to be tucked in?” Emily chimed in as she picked up the roll of duct tape that had been used before.

Tim's breath hitched. “Wait, what’s the tape for?”

Sarah gave him a playful grin, one that made him feel a little sick. “Oh, this? Just a little extra security. You didn’t think we’d trust you to behave yourself all night, did you?”

“Security? I’m not going anywhere!” he protested, stepping back and clutching the blanket and pillow to his chest like it might shield him, and hiding the guilty look on his face.

Emily grabbed his wrist with practiced ease and began wrapping a loop of tape around it before he could yank it away, causing the objects he held to fall to the floor. “We’ve heard that before, but boys can’t be trusted. That is why we want to keep Tammy around, one less perverted boy on the compass.” Her tone was light, but the tape still tore as she finished one wrist and moved to the other.

Sarah helped guide him down to sit, then laid his ankles side by side. “Let’s not make a fuss. It’s not like we’re tying you to a radiator.”

“Yet,” Emily added, "not that there is a radiator in the room.”

Despite the half hearted jokes, the tape held firm as it was pressed snugly around his calves, then his thighs. It didn’t cover his entire newly shaved legs, just two small bindings that didn’t cut off circulation, but it made it very clear that sneaking away in the night wasn’t an option. Not without loud rustling or a very awkward shuffle that would wake them both.

As Sarah pulled the blanket up over him, tucking it in a little too cheerily, Tim lay stiffly on his back, arms pinned close, legs held nearly together. Even shifting slightly was difficult. The soft cotton of the oversized t-shirt clung awkwardly to the corset’s boning beneath. His pigtails splayed out on the pillow, a cruel little flourish to finish off the look.

“Sweet dreams, Tammy,” Sarah whispered, flicking the bedroom light switch to plunge the room into soft darkness.

“Yeah,” Emily added from her own bed. “Don’t stay up, you need your beauty sleep.”

Tim closed his eyes, his mind spinning as he listened to their beds creak faintly while the girls settled in.

Laying motionless beneath the blanket, arms pinned awkwardly at his sides, legs taped together. Every inch of him ached, the corset compressed his torso with every shallow breath, his calves throbbed from his little walking training. He was sure that if he went through more even his cheeks would hurt from all the fake smiling. The oversized Tri Sigma shirt clung uncomfortably to his frame, its hem barely brushing past the tight panties that he didn’t want to be wearing despite how soft they were compared to his normal underwear.

He tried to shift but only managed a small twitch. He could move from his back to his side, but the tape around his thighs and calves didn’t leave much room for anything beyond slight wiggling in place. The pillow beneath his head was at least soft and comfortable, though having his hair pulled into pigtails in an unwelcomed way was unwelcomed.

His thoughts swirled like leaves in a storm for how his day had gone. Just this morning, he had been scrubbing grout in the frat house bathroom with a toothbrush, joking with another pledge about how being hazed was just part of brotherhood. He remembered thinking that once initiation was over, he’d have real friends, people he was bonding with right now, guys who’d back him up, who’d invite him to parties, who’d help him finally find his place. That was the goal, that was the dream.

Now Timothy found himself laying on the carpeted floor of a sorority house bedroom, his wrists taped together, wearing a bra stuffed with breast forms that were glued to his chest, hair in pigtails and wearing panties he had originally come to steal as the last step in his initiation. Least he was pretty sure it was the last step, the conversation he had earlier felt vague with how excited he was about the task before and how it had gone.

His lips trembled. ‘How had it gone so wrong?’ He tried to piece it all together, sneaking in, getting caught, being called a pervert, the waxing, the makeup, the dress, the voice training, the shoes. Each moment seemed too bizarre to be real. Like some absurd, humiliating fever dream he couldn’t wake from.

And yet… it had all happened. Tim knew the option to tell the girls no, or to be firm to tell them to go to hell… but that wasn’t him, the consequences felt dire. Really his best shot would probably have been to just run before they knew who he actually was, where he had come from, but he hadn’t done that. Tim knew he was a coward, he had things he wanted within his grasp and now he didn’t know what was going to happen.

They had him looking like a girl and it sadly wasn’t some magic, he was hardly a man or at least it felt that way right now. It wasn’t some joke, like when a football player put on a dress with his broad shoulders and hair legs sticking out from the bottom. No, when he saw himself in the mirror, it wasn’t just makeup and lighting, he saw a girl. He saw who they had dubbed Tammy.

He doubted anyone outside that room would’ve known it was Timothy Thompson they were looking at. The weary teen thought of his pledge brothers, to his friends… really just school mates he had grown up with back home and even his own mother. Doubt is what went through his mind on if they would call out his own name if he walked by them and it only made more feelings well up. The realization brought a fresh wave of shame that somehow felt deeper than everything else. His mind jumped to wild ideas as he laid there in the dark bedroom. Could he sneak out after they slept? Could he find his old clothes? Could he just… forget this ever happened?

But every path he imagined ended with disaster. They still had his ID, his phone, his clothes. They’d seen his face, his body, his reaction to every bit of this. He wasn’t just trapped physically he was trapped in the moment, in the secret, in the persona they had stitched around him piece by piece.

Tim wanted to cry, he wanted to scream at his own powerlessness.

Instead, he just laid there, staring at the ceiling, the dull ache in his legs matching the deeper emotional pain in his chest.