Chapter 11

The borrowed heels Tim wore heels clicked sharply against the pavement as Emily’s hands pressed firmly into his shoulders, steering him down the sidewalk outside the sorority. One foot stepping in front of the other, heel toe, heel toe like he had been taught, moving like he was a doll being guided on stage. His legs wobbled inside the glossy red heels, each step precarious and ****, the pointed the pointed toe shoes with the four inch heels were wrong for a male like him to be wearing, but he could admit looking down at his feet in them was a bit of a turn on, only it was his own feet, making his own feelings adding to the wrongness. The clinging of pantyhose against his thighs only made him more aware of every movement, the material on his legs a new and exciting experience, not that he would ever voice such a thing. The slinky spaghetti-strap dress clung snugly across his chest and hips, the hem swishing indecently high against the middle of his thighs, the brushed lightly over his nylon covered legs with every movement. Almost every few steps he darted a glance down at himself, as if hoping the outfit might miraculously cover more than it did.

Sarah trailed behind with a bright grin, her voice far too cheerful for the pit of dread curdling in Tim’s stomach. “Tammy is going to have so much fun tonight,” she sang, swinging the little red purse hanging from her fingers before pushing it against his side. “I’m a bit jealous, well not with who you are going out with Tammy, but I’m thinking about a date in the near future for myself.” The petite brown haired girl said, looking over the feminized boy as her friend helped guide him down the path to where they were going. “We made sure you are ready for whatever you get up to. Condoms so you don’t end up pregnant, mouthwash in case you want to go down on your date. Gotta keep your options open, right? I mean, one of your goals is making him happy, and with how you are dressed I’m sure he will have ideas of things he wants. Boys are like that, perverts that get ideas on what they want and deserve.”

Emily glanced back at her friend, agreeing for the most part with what she was saying, but keeping it to herself how she knew more than a few girls with just as dirty minds and not wanting to do any self-introspection on the topic.

Tim meanwhile held his pretty makeup covered eyes wide as if paralyzed that way. He stumbled, the heel of his shoe catching in a crack on the sidewalk before Emily steadied him with a semi gentle shove forward. “I… I can’t do this… I don’t want to do that, please don’t make me?!” he whined in the feminine voice he had been practicing, it sounding like it was both a statement and a question. His face burning as if the entire neighborhood had just overheard what they had been talking about, seeing a boy in a dress, being pushed off to meet up with a guy he was going to have sex with. The purse’s strap slid against his bare shoulder, the little heart-shaped clasp glinting in the morning sun.

Neither girl slowed, Emily’s guiding hands like iron against his back while Sarah’s grin widened with every word. “Relax, Tammy. We aren’t making you do anything.” she said, her tone light and playful, but carrying just enough weight to remind him this wasn’t really a choice, despite what she was saying out loud.. “We’re just making sure you’re prepared. You know, for when you decide you want to feel his… girth inside you.”

As she spoke Emily had a difficult time not laughing. “A good sorority sister doesn’t show up unprepared for a date.”

Tim swallowed hard, his throat dry. Just hours ago, breakfast had seemed almost… normal. In fact despite the situation he had been in, breakfast has been better than normal. Awkward, humiliating, yes, but still nice in more than a few ways. Now here he was, being shoved out the front door in a skin tight red dress walking in heels, that made him feel like he was going to fall down despite all his practice, while listening to Sarah talk about him having sex like it was the most natural thing in the world. ‘This can’t be happening to me…’ the thought ran through Tim’s mind. He was a virgin and they wanted him to be with another guy, not that he told them he had never been with, let alone kissed a girl before.

His stomach knotted as he thought back over the day before, how it had all spiraled to this moment. Yesterday had gotten worse and worse, this morning hadn’t been pleasant, with a calm within the storm he seemed caught up in, that was breakfast. After that they’d drilled him again, making him sit straighter, cross his legs at the knee, at the ankles when sitting. Soften his voice like the night before, practice smiling and giggling until his jaw ached. Then came the news. The “good news,” they’d called it. A date. Tammy had a date.

And now, with each **** step where he moved with a wiggle to his hips down the walkway, Tim felt the dread settle deeper into his chest. He wasn’t Timothy Thompson anymore. Not to them. Not tonight, whoever he was meeting would only see Tammy.

Tim’s chest tightened as he walked, the sway of his hips no longer just clumsy stumbling but a practiced, unnatural rhythm. Heel to toe, hips rolling slightly, arms kept soft at his sides. Every step was borrowed, an echo of what Emily and Sarah had drilled into him upstairs. The glossy red heels pinched at his toes, forcing his arches high, while the thin pantyhose slipped inside the shoes with each step, making him feel unsteady no matter how carefully he moved. The sound of his footsteps echoed sharp and clean, the kind of clicks that could only belong to a girl’s shoes.

Every muscle in his legs burned from the posture, but worse was how easily his body obeyed. Even when he wanted to stomp or slouch, his body kept falling back into the motions they had hammered into him. His mind scrambled back to the hours that had carried him here, trying to piece together how everything had unraveled.

After breakfast, the calm ended quickly. Emily had him standing once again on the duct-taped line in their bedroom, his feet now in a different pair of shoes, but very much still heels. Emily had her arms folded and her voice sharp as she spoke to him more like an odd drill instructor that was obsessed with making him more feminine. “Voice, Tammy. Softer… little breathier. Try again.”

Sarah lounged on her bed, chin propped in her hands, eyes sparkling like she was watching a favorite show. “Don’t stiffen up so much. Just let it roll off your tongue, like you’re saying something fun.” She raised her own pitch in a sing-song imitation. “Hi, I’m Tammy, I do love shopping!”

Tim’s falsetto cracked as he repeated it. “Hi… I’m Tammy.” he tried to mimic what she was saying, feeling like he was one of those speaking dolls and they had just pulled the cord.

Emily’s head shook immediately. “Too flat. You sound like you’re being strangled.” she demonstrated by pretending to strangle the air.

Sarah giggled and leaned forward. “Hey, it’s still better than last night. Then you could barely get through a sentence without croaking. Now it’s… I don’t know, halfway cute?” she said trying to play down her own thoughts.

Heat crawled up Tim’s face as he kept trying, the blush being pretty much continuous as they made him practice, each correction making him feel smaller, but there was nothing else he could do.

When Emily gestured for him to sit, he dropped into the chair too quickly, legs spreading wide until Sarah nudged his knee with her foot.

“We went over this. Tammy, sometimes I think you have the memory of a gold fish and we need to improve that to at least blonde bimbo level. Now, legs together so that your thighs are touching and cross your ankles. We at least need you sitting like a girl, before you can sit like a woman.” Emily coached in her not so gentle tone.

“Pretend you’re wearing a skirt. Because, well, you will be.” Sarah offered, looking at the blonde boy still wearing the same thing he had to sleep in with his legs exposed.

Tim obeyed, the corset pressing into him, though the compression felt less like a vice and more supportive than it had the night before. That wasn’t to say it wasn’t a problem and something he did not want to wear as it **** his back straighter, the boning holding him upright whether he wanted it or not.

Emily circled him, eyes sharp. “You’re improving,” she admitted at last, though her tone made it sound closer to a warning than praise. “But you have a long way to go little girl.”

“How long is this going to go on? I mean… are you ever going to let me go?” His voice cracked closer to his real one, the words spilled out before he could stop himself.

Sarah tilted her head, her smile softening. “We told you, Tammy. You can’t just walk out half-finished. Training takes time.”

Emily took in a slow breath. “We are going to give you a test, once Tammy proves she… you can really pass as the kind of girl people expect, then things will change for the better.”

Tim bit his bottom lip, looking between the two girls, feeling as if the words were dangling before him like bait. “What kind of test?” They had kept him compliant with their threats, still what they had said they would do weighed heavily upon him. It would ruin his life to come and being embarrassed, much as he didn’t want to go through all this, it was the better option.

Sitting down on her own bed Emily cracked her neck to one side and letting out a happy groan at the release. “The kind that you will fail if you continue to act like a tomboy. So simple question Tammy. Are you the type of boy that will steal girls' panties to join a frat, or the type of girl who would have fun with her friends in a sorority?”

A light giggle escaped Sarah’s lips at the odd question. “I think she looks more like a girl.”

“I’m…” Tim stated and then stopped. What he was about to say felt wrong, but so much of everything in his situation was wrong. Him getting caught on the very pantie raid Emily was mentioning, possibly going to jail if they reported him, being kicked out of school, disappointing his family, never having even the smallest chance of getting friends at the fraternity because he had not been cautious enough. He needed a way out and that meant pushing through his pride, little that he had. “I’m Tammy, of course I would rather join a sorority.”

Tim didn’t know if his lips were actually dry or if it was just a subconscious feeling after what he had just said, but he licked his lips as the softer more feminine voice he had been using played out in his own mind. ‘I’m Tammy, I’m Tammy, I’m…fucked.’ He hated himself for saying it, but he had to do something to improve his situation.

Emily’s smirk spread slowly, satisfaction written across her sharp features. “There we go,” she said, leaning back on her bed. “Finally admitting it. Our little Tammy is starting to understand where she belongs.”

Sarah’s giggle bubbled out, as she wiggled happily. “See? I told you she looked more like a girl anyway.”

Tim hunched slightly, or as much as he could with what was wrapped around him.He wanted to take it back, to say it was just words to keep them happy, that was the truth of it but that didn’t matter and speaking the truth wasn’t going to help him at all.

“Well, since you’re so eager to be one of us,” Emily began, her tone shifting into something falsely bright. “We’ve got good news.”

Tim doubted it was good news, but if it led to his freedom and escaping the threat of the police getting involved then he was all for it. “I could use good news”

Sarah perked up too, eyebrows lifting. “Ooh, what is it?” She hadn’t been in the loop for her friend's idea of a test, just having been going along with it till questioning things now.

Emily raised one hand in the air, moving it around in a circle before letting it fall so she could point directly at the blonde college freshman. “Tammy has a date.”

“A… a date?” His voice cracked high, close to his real one, and he scrambled to pull it back down into the softer tones they had drilled. “With who?” He had never been on a date and the idea of it being one of the girls he was in the room had its appeal. Both of them were pretty in their own way, he didn’t have a great deal of money to take either of them out or really anyone out, but if they wanted him to act girly to go out he could… he really didn’t want to, but it wouldn’t be that bad. That led his mind down the path of wondering if one of them, or both of them were more into girls than boys or they liked both.

Emily only shook her head, wagging a finger. “Doesn’t matter. What matters is you’ll be out in the world, with a boy, and he’ll see you as the girl you are.”

Sarah’s mouth formed a perfect O before she broke into delighted laughter. “Oh my God, seriously? That’s… Wow. Wow, wow. Talk about a test run.” Her blue eyes locked onto his hazel ones that looked practically large enough to be dinner plates with how wide they were. “Your first date, Tammy.”

Tim put a hand to his head, taking a step backwards, him not even noticing how he didn’t stumble or twist his heeled foot at all as he did so. “No. I can’t do that. I’m straight! And… and someone outside will know, it’s too much.”

Emily’s voice cut him down, calm but with a sharp edge. “Yes Tammy, I know you're straight. Think carefully. Why did you admit the truth that you are Tammy, not some tomgirl trying to join a frat, or worse… The creepy boy who tried to steal panties? Or would you rather be the cute new girl who gets asked on dates?”

Tim’s throat worked, but no sound came. His own words from a minute ago twisted around him, a trap he had freely walked into thinking it was his salvation. ‘I’m Tammy, I’m Tammy…’ not for the first time or the last his own words repeated in his mind. ‘Emily is using me against me! This isn’t fair, this isn’t… I don’t… have a choice.’ he cocked his own head back, looking up to the bedrooms ceiling. “I do have a choice.” he whined out loud as he corrected the thought, but knowing the consequences between those choices. Go along on this date with a boy to earn his freedom, or refuse and be doomed.

Sarah leaned forward, her smile softening. “It’s not that scary. Girls go on dates all the time. Think of it like… trying to find the one, you know someone to be your boyfriend. Sometimes we have to kiss a few frogs to find our prince.”

Emily raised an eyebrow, already knowing the answer to her question before she asked it. “Oh, found a lot of princes?”

Sarah gave her stupidly tall and pretty friend a partial frown as she slumped her shoulders. “Just frogs and you know it, but we will see.”

Emily stood, circling behind the upset boy again like she had during femininity drills, her hand brushing over his shoulder. “This is the test, Tammy. You said you’d rather be a girl with friends in a sorority than a boy caught as a creep. Or something close to that…” She closed one eye trying to think, not able to come up with his exact words so she powered on forward. “So prove it. Prove you’re the right kind of girl. All you have to do is smile, talk pretty, laugh at your date's jokes, flirt a little but mainly make your date happy.”

His heart thudded painfully. “And if I do?” he asked, his voice barely audible.

“Then things change,” Emily promised, her tone firm.

Sarah clapped her hands together, unable to contain her excitement. “So… you want to go on a date with a cute boy, right Tammy?”

The way she looked at him, expectant and eager, made his insides twist. He couldn’t say no, not now, not after everything. Slowly, he nodded, each word scraping out of him like it cost a piece of himself. “I… I want to go on a date.” he swallowed hard, taking a breath before forcing a smile to his face and speaking with a false chipper voice. “But, only if he is cute.”

The girls beamed, their satisfaction filling the room like sunlight. “Great!” Sarah said practical with stars in her eyes. “So you tell us, what would you like to work on next? Do you want to practice flirting?”

Tim knew he had no real skill with flirting, tips on how to be better on it would be helpful, but what they were offering was not a skillset he wanted to learn. How to pick up boys and keep their interest was not on his agenda, not that he could really say that right now. “I just want this to go as painlessly as it can, whatever you say.” Tim’s voice came out soft, the practiced lilt in his voice as he spoke, his very voice sounding out of place to himself.

Bouncing her head from side to side Emily’s dirty blonde hair that she still hadn’t taken the time to tame yet that morning bounced about as she considered the answer and how to proceed before giving a short nod as if that were the answer she had been waiting for. “Good girl. Then it’s time to get you ready.” Her gaze swept over him, unimpressed. “That t-shirt might work for sleeping, but you’re not impressing your date in it.”

Sarah perked up immediately, bouncing to her feet. “Finally, dress up time.” She hooked her fingers into the hem of the oversized shirt and tugged it upward. “Arms up, Tammy.”

With little choice in the matter Tim still hesitated before lifting his arms, his face once more becoming a shade of pink as Sarah peeled the shirt off over his head, to leave him mostly exposed. The cool air of the room hit his skin, leaving him standing in few articles of clothing, none of them his own and none of them fit for a college age boy to be wearing. Panties, the same ones he attempted to steal the night before, bra, a corset and the high heels he had just been practicing walking in. His chest felt bare despite the bra straps biting into his shoulders, the unease having him cross his arms over himself instinctively.

Tugging his arms down firmly, Emily shook her head. “None of that. You wanted this to be painless? Then stop trying to cover yourself, after all you are a pretty coed getting ready for your date, you should be happy, not self conscious.”

Sarah gave him a reassuring smile before walking over to the shared closet and pulling out a slim red dress. The thin straps dangled from the hanger, the cotton blend fabric shifting slightly as she walked closer. Then she stopped, tilting her head. “Wait. I’m getting ahead of myself.” She gave an apologetic smile to the boy that was about to pretend to be a girl, though he didn’t really pick up on her own embarrassment.

Blowing out a breath of air, Emily moved toward a dresser. “Good point. No boy wants a date who still looks like she just rolled out of bed.” She slid open a drawer and pulled free a fresh pair of panties. “Tammy is going to borrow these… They match the dress.” Emily glanced over to her friend, seeing her wince slightly before shrugging. They both knew Tim didn’t have any panties of his own to wear and Sarah’s would fit a lot better than Emily’s underwar. with a small bow stitched at the waistband. She tossed the undergarments in a way that they landed on the frozen boy’s face, the little bow on the waist band on display. “Change, and don’t hide yourself, we are all girls here.” Emily didn’t really have any interest in seeing his little penis, but the boy seemed so shy that she was sure it would bother him.

Pulling the panties into his hands he felt the thin fabric between his fingers and nodded slowly, agreeing. He got through life by trying to put his best foot forward when someone asked him to do something, but it was hard for him to just go along with this, despite his agreements. “I… do I really have to…”

Emily’s eyebrow arched, daring him to continue.

With his lips pressed tight, Tim peeled off the old pair, his body twisting slightly as he stepped out of them. Quickly as he could, he pulled the new panties up his legs, the underwear feeling cool as he stepped into them, the silky fabric pulling snug around his hips until the little bow at the waistband sat squarely against his front. It stood out like a mocking reminder, a detail no boy should be wearing.

Sarah held in the mega-watt smile that wanted to show on her face, though she couldn't fully contain it as she watched the boy slip into her panties, her underwear covering his manhood.

“Okay, that is cute.” she said, her eyes lingering towards his groin.

Emily was already reaching for the next piece. She held up a strapless bra, the cups lightly padded. “Arms through.”

Things were happening quickly enough that Tim had enough time to be uncomfortable, but not enough to over think things as he slid his arms into the bra straps. The underwear felt different than anything he had worn in his normal life. He had worn a pair yesterday, they just like what he put on down was forbidden and yet comfortable. The bra on the other hand was something only girls wore making it more than a little taboo, making him once more swallow hard, as it was adjusted, the thing clinging to him.

“Hmm, tha looks looks good.” Emily nodded, her seeing Sarah doing so as well so she continued wanting to tease him a little. “Boys pay attention to these things.” Emily said, poking the fake artificial cleavage.

The touch caused Tim to flinch, he couldn’t actually feel her touch, but he could feel the pressure of it through the glued on assets that filled out the bra cups.

Emily stepped behind him again, fingers catching the laces of his corset. “Time to up the gear on your waist training, everyone has unrealistic expectations of how us girls should look… Breathe in.”

While Tim sucked in a sharp breath, Sarah gave her friend a questioning look, the taller girl always having a natural figure she envied as her own lack of self confidence let itself be known.

The laces tightened, the boning pressing harder against the teens ribs until the pressure made him wince. “Again.” Emily said, holding the laces tight, them wrapped around her fingers. After another pull a knot was made to hold everything in place. Almost like magic the shapewear helped transform the boy. Not much had changed from the outside, the adjustment only getting another half inch off his waist, but it was indeed narrower than before.

“There,” Emily said, giving his side a pat. “Now you actually have a figure. Still not much, but no one’s going to take one look at you and think boy.”

Tim let out a shallow breath, his chest restricted, each inhale shorter than the last. The corset **** his shoulders back and his spine straight, holding him rigid whether he wanted to be or not. None of that was different than what he had endured while even sleeping in the thing, but he had grown more accustomed to it, now it was back to square one.

Sarah finally returned with the dress. Her eyes glittered as she held it open for him. “Now you’re ready for this.”

His lips pressed tightly together, knowing he couldn’t fight this and needed to do everything he could to make his tormentors happy so it didnt’ get worse. So he did what he always did in life, smile and do what he needed to to get along to go along. “That is a super cute dress, are you sure I can borrow it?”

Not for the first time Sarah’s eyes practically lit up, the question raising her level of excitement. “YES!” She blurted out before clamping her hand over her own mouth. “I mean, yes, I don’t mind at all.” The dress itself had been one her aunt had bought for her, hoping Sarah would open up more in college and go to parties, but it had mostly just sat in her closet till now.

The dress hugged his waist and hips, then stopped at mid thigh, indecently high as far as Tim was concerned or at least he thought so when it was on him. Sarah smoothed the fabric down with both hands, smiling with a pure chipper attitude as she did.

Sarah stepped back to admire him, then clapped her hands once. “Almost there. But a girl like you never goes out without her nylons.” She bent to retrieve a fresh pair still in the package from her drawer, the thin square of plastic crinkling as she tore it open.

Tim’s stomach tightened. He had seen pantyhose countless times on girls in real life and on TV, their legs shimmering faintly under skirts or dresses, the sheen catching light in ways bare skin never did. He had said out loud or even really gave it much thought, but he had always noticed, his eyes lingering longer than he meant them to. Now Sarah was kneeling in front of him, holding out the gossamer fabric. The pretty petite girl kneeling in front of him had its own train of thought as he sat on down on the edge of the bed and his hormonal mind had a hard time parsing both the sight of the girl smiling kneeling in front of him and what she was about to put on him.

“Sit,” Emily ordered, giving him a command for something he was already doing on its own, resting her hand on his shoulder, giving it a light squeeze that might have been reassuring to others, but not to Tim in that situation.

Sarah shuffled a little closer, her crouched gracefully, bunching the pantyhose with practiced fingers. “Point your toes.”

As Sarah began to slide the pantyhose up his leg, Tim felt a rush of sensations he had never experienced before. The cool, smooth fabric glided over his skin, the slight tension as it stretched to fit his form sending shivers down his spine. The material was surprisingly thin yet remarkably strong, the delicate weave clinging to his legs with a gentle, almost intimate pressure. He could feel every slight movement, every shift of the fabric against his skin, the sensation both exhilarating and slightly unsettling. The pantyhose felt like a second skin, enhancing the sensitivity of his legs, making him acutely aware of every touch, every brush of air. He tried to keep his expression neutral, to hide the flush of arousal that threatened to betray him, but the sheer sensation of his skin was almost overwhelming. Sarah’s fingers, gentle and sure, guided the pantyhose up his thighs, the sensation of her touch through the thin fabric sending waves of heat through his body. He could feel the material hugging his legs, the slight give and pull of the material as he moved, the way it accentuated the slight curves of his smooth shaven skin. It was a strange, intoxicating feeling, one that he knew he would never forget.

It was unlike anything he had ever felt. The fabric was so thin that it seemed to amplify every sensation, making him hyper-aware of the faintest breeze from the air conditioning. As the brown haired girl continued to pull the pantyhose up, he could feel the material tightening around his thighs, the gentle pressure sending a thrill through his body. He tried to focus on his breathing, to keep his composure, but it was impossible with the garment restricting him under the dress, making the eroticism of the moment too much to ignore. The sight of Sarah, her blue eyes locked on his, her hands gently guiding the pantyhose, only added to the intensity of the experience. Tim had never been touched like this and could once more feel the heat rising in his cheeks, a blush that wasn’t just embarrassment but a flush of desire spreading across his skin, and he knew that she could see it too.

Tim swallowed, each of his shallow breaths coming rapidly as he shifted slightly. The silky texture of his thighs touching one another making his groin cause a bump that looked out of place on the tight red dress, making the wrongness mix with his personal excitement to add confusion to it all.

Before he could process it, Emily was crouching at his feet, the red heels already in her hands. She slid one onto his nylon covered foot, the fit smoother now then when he had the feminine footwear put on before, making him not sure how to act, only hesitation filling him.

Emily’s eyes swept over him, her lips curving faintly. “Good… Huh, I wasn’t expecting that.” her eyes holding firm on the tent that was being made in the dress.

Drawing attention to it only made Sarah burst out into laughter, her covering her mouth trying to hold it in and failing miserably. “Oh…” she laughed some more. “Tammy, you look…” she continued to laugh. “That isn’t lady like, you are going to need to calm down.” Despite how funny she found it, another part of Sarah was feeling intense feelings of her own that she wasn’t sure how to grapple with.

“Okay, okay.” Emily looked between the two. “We still need to do her hair and makeup, but Tammy here getting excited is the perfect time to transition to a talk about what is expected on her date.”