Chapter 4

The room was filled with a tense silence as Sarah returned with the box labeled "Charity." Emily's eyes gleamed with a mix of amusement and malice as she watched Tim, who stood naked and ****, the pink thong clinging to his skin. The sight of him in the underwear was both humiliating and arousing, a constant reminder of his betrayal and the consequences that followed.

Emily stood up from the bed, her movements graceful and deliberate. "Alright, Tiny Tim, let's get started. Sarah, hand me the waxing strips."

Sarah complied, handing Emily the box of waxing strips, her eyes focusing on Tim's face, seeing it flushed with embarrassment and fear.

Emily opened the box and pulled out a strip of wax, knowing exactly what method to use to hit up the wax. “Sit down at the end of the bed here Timmy.” she said, putting the bed for him to sit down, looking the smaller man in the eye so that he knew she wasn’t asking.

"Please, no," he begged, his voice trembling. "I'll do anything else, just not this." Despite his begging and assertion he would do anything other than this he still sat down where he had been told.

Emily's smile was cruel. "Too bad, Timmy. You should have thought about that before you broke into our room and went through Sarah's underwear, you little pervert. Now take this." Emily handed him one of the sealed waxing strips. “Hold that in one hand and rub on your palm across it rapidly that way the waxing strip heats up. I normally use a hair dryer, but I like the idea of you putting some effort in to get nice and smooth.”

Standing still Sarah watched on in fascination, the anxiety from the teen boy was palpable as Emily controlled him down the path of his own destruction. She thought the word destruction that came to mind was a bit hyperbolic, but nonetheless she stood there just watching as he heated up the strip before Emily Peeled it back to place it on his thigh.

Tim took a deep breath, steeling himself for what was to come as he watched the taller girl’s fingers pinch the strip after it sat on his skin for a short while. “Ready?” Emily asked before starting to count. “On three, one, two…” She then pulled the strip off in one smooth motion before getting to the correct count.

Tim knew he had little to **** but to comply with this insanity if he wanted to avoid the cops and the potential ruin of his college career. So he sat there just staring at the strip on his leg, biting his lip, feeling the wax that had been warmed up just enough to make it adhere to his leg. Tim tried to be emotionally strong enough to not let tears come to his eyes as he braced for what was to come. The blonde boy didn’t have the frame of mind to know how this was about to feel though and as the strip was ripped off he yelped in pain.

Tim's eyes watered, and he couldn't help but cry out in pain after taking in a deeth breath through his clenched teeth. "Fuck, that hurts!"

Emily's laughter filled the room, a chilling reminder of his humiliation. "You don't even sound like a man. Not even a woman. You sound like a little girl."

Sarah watched the scene unfold, her expression a mix of pity and fascination. She could see his tear filled eyes welling up even before the wax strip was pulled from him, making her feel a sense of pity, something that would make her want to help him, but she wasn’t going to give in to her natural sense of empathy. This was still the person that put his hands in her panty drawer just because a stupid frat thought it was okay to violate her personal space and steal from her. The exclamation itself from the sudden pain was both disturbing and captivating. She couldn't help but feel a twisted sense of satisfaction, knowing that he was paying for his actions. Filling her with complicated emotions on wanting him to both suffer and to come to his aid.

“Awww, it doesn’t hurt that much little one, you have to be a brave girl for me because we are just getting started.” Emily laughed as she put another wax strip in his hands, planning to actually do more than one at a time now that she got his first reaction to being waxed. When one was warm enough she instructed him on peeling back the initial strip and placing the next strip on so there was a slight overlap from the first so that they got all the hair. Making him place all the strips, the boy doing exactly as she said knowing he was about to feel the pain from his own efforts gave her some satisfaction.

Initially the idea of just beating the shit out of him and then calling the cops was really appealing, but now she wasn’t positive she could go through with that kind of act of ****, it was a bit too far, an emotional response that didn’t seem to fit now that her adrenaline had come down. A bit of suffering though for what he did… that felt right to her.

With each yank of a strip, each flinch from the freshman gave her a sense of vindication. Boy’s always seemed to just do what they want in her life. She had shot up in height in middle school, at home her mother and aunt said how beautiful she was, but Emily only felt awkward as it made her stand out. Sure she wasn’t the only girl at that age that had a growth spurt, but few boys did and they found it as an avenue to make her feel like she was standing out in the worst ways, like when they snapped her bra strap. The saying boys will be boys infuriated her, like just because they had a dick it gave them the absolute right to just act out without real repercussions while she was told to just ignore them, to smile and move on. Tonight she was not going to move on. Tonight she was going to start making things right.

With wax stripped applied then ripping it off with the same cruel efficiency each and every time, Tim's cries of pain filled the room, a symphony of his humiliation and suffering. The volume of his exclamations went down significantly as things went on, but by then it was just time for Emily to move on to another part of his body, his chest, arms, and underarms, each strip of wax tearing at his skin and leaving him in just a little bit more agony. The pain wasn’t exactly excruciating, but it was repetitive and Tim couldn't help but beg for mercy.

"Please, stop," Tim pleaded, his voice hoarse from crying. "I can't take it anymore."

Emily's smile was cruel. "You can and you will. We're not done yet." she said, ripping a strip from his back.

Emily stepped back, her eyes roaming over Tim's body with a critical gaze after she had pulled off more strips. "Not bad, but now we do need to do some after care." she sighed, knowing the pain part of her plan was coming to an end. Not applying a balm to ease his soreness felt right, but she also knew that was her just wanting to be vindictive. “Here, put this one, is a hydrating cream with aloe.”

The lightly tossed bottle hit Tim’s hands, and he fumbled with it a few times before it fell to the floor. “Sorry…” he apologized, picking it back up.

“Don’t be sorry, just do as you're told.” Emily snapped, glancing over to Sarah.

The cream from the bottle felt cold on his skin as he ran his hands on his tender skin, and it seemed to be exactly what his body wanted after the punishment it had just endured. It didn’t magically make his red skin better, but it was something close, though another side effect of it made him that much more aware of just how close to being naked he really was. His freshly waxed skin feeling tender and cool from the cream allowed him to somehow feel the air conditioning over his body that much more, leaving him feeling more exposed.

Sarah, who had been mesmerized by the waxing process, blinked a few times as if waking from a trance. She shook her head slightly, a bubbly smile spreading across her face. "Right! Hair time!" she exclaimed, clapping her hands together enthusiastically.

Grabbing a spray bottle filled with water, she motioned over to the cheap metal chair they had by their shared vanity in the shared room. “Can you please come sit over here Timmy, I promise this next part will be less painful.” she asked as she pulled the chair out.

Her pleasant expression was completely different from the hot girl who had been giving him what felt like an evil glare the entire time she was making him suffer. It was like the look his own mother gave him when she was serious, but it dialed up to eleven. “Yeah, yeah, sure, but umm you can just call me Tim if you want. No one really calls me Timmy.”

“Don’t correct her Tiny Tim.” Emily prodded him with the tip of her index finger so that her acrylic nail pressed into his skin.

When he sat down he immediately felt himself being sprayed with water from the spray bottle in the much happier girl’s hand. The cool liquid dripped down his scalp and neck causing Tim to shiver at the sensation, a mix of relief and discomfort washing over him. Sarah's hands were gentle, so much gentler than Emilys but firm as she brushed out his hair, the bristles gliding through his golden blonde locks. Each stroke of the brush felt good, a real contrast the pain he had just endured, allowing the tightness in his muscles to start to relax. ‘This isn’t so bad…’ the thought coming to his mind unbidden as the tension started to leave his body, almost enough to make him temporarily forget that the only article of clothing he was wearing was a pair of pink panties.

"Ooh, look at that hair," Sarah cooed, her voice bubbly and happy. "It's like a golden waterfall. I wish my hair was as pretty as yours, Tim."

Emily chuckled, watching the scene with amusement. "You're enjoying this a little too much, Sarah."

Sarah giggled, not taking her eyes off Tim's hair. "Oh, absolutely. It's like giving a puppy a bath. He squirms and whines, but deep down, he loves it."

A heavy blush came to the teen boy’s face at the comparison, his face burning with embarrassment. Those thoughts of what he was wearing came back to his mind in full ****. He wanted to protest, to tell them that he didn't enjoy any of this, but he knew it would only make things worse.

Emily rolled her eyes but smiled. "Well, let's hope he enjoys the next part even more. I know I will." She said opening up her makeup bag.

Every time the brush got caught on a tangle, Sarah had to be rougher, pulling at his hair to untangle it. Tim winced in pain, as she pulled on his hair but before he could squirm away, he felt Sarah flicking the back of his ear, a sharp sting that made him yelp.

"Stay still, Tim," Sarah said, her voice sweet but firm. "Your hair could use a good wash and conditioning, you don’t take nearly as good of care of your hair as you should, but we don’t have time right now."

Tim gritted his teeth, trying to hold still as the girl continued to brush his hair. The sensation was almost completely pleasant, each stroke of the brush feeling nice, but every so often it would get caught in a tangle, adding a little jolt of discomfort. "Ouch!" Tim exclaimed as Sarah flicked his ear again as he pulled away on instinct.

"Sorry, Tim," Sarah apologized even as she flicked his ear. "You have to stay still."

Emily watched the scene with a smirk. "Timmy, I don’t want to hear you whining like a little girl. You are in college, do try and act your age."

Sarah giggled, at the comment, leaning in close to whisper to their captive. “I think it is cute that you are so sensitive.”

Tim's face was a mask of humiliation as he sat there in silence while Sarah finished brushing his hair, her hands moving to the back of his head. She began to gather his hair, twisting and pinning it up into rollers. The sensation was unfamiliar and intimate, a constant reminder of his current torment. Tim could feel the tightness of the rollers as they pulled his hair tighter and tighter as they rolled up to press against his scalp.

"You know…” Sarah said, rolling up a section of the boy’s hair. “If you took care of your hair more it would really be lovely, I mean you got pretty golden hair, while I have boring mousy brown hair. Really isn’t fair."

Emily, who had been watching the interaction, as she finished setting out what she was about to start using on him, chimed in with a soft smile. "Your hair isn't boring, Sarah. It's cute. I wish my hair was as thick as yours."

Sarah blushed slightly at the compliment, her eyes meeting Emily's for a moment. "Thanks, but I think boy’s notice yours a lot more than mine."

The two girls shared a brief, positive moment, their banter going on just long enough for Tim to feel like they had forgotten he was there, or it would have if the smaller girl’s hands hadn’t continued to put his hair in girly rollers. He could tell there was a real friendship between them, giving him a pang of jealousy at their connection. It was what he wanted, the reason he had done this in the first place, to join the fraternity and gain friends.

As he ruminated on his lot in life, he heard the brown haired girl speak up, pulling him back into the moment. "There we go," Sarah said, stepping back to admire her handiwork. "You look cute."

Emily, having finished setting up the makeup she needed on the shared vanity, turned her attention back to Tim. She had a wicked grin on her face, her eyes gleaming with malice. "Alright, Timmy, it's makeup time. I bet you can’t wait to be pretty."

Tim's heart sank as he realized what was about to happen. He could recall sitting at the edge of his parents bed, kicking his feet in the air as a child as he watched his mother put on her makeup more than once, her natural beauty being enhanced one stroke at a time with the different products. The thought of having it applied to his face was both more than a little humiliating, though not much so than being waxed. He thought about protesting, as he slid his hand over his smooth thighs, it not being the first time he had done so as he sat in the chair, any protest he had dying before it came to his lips.

Seeing the boy open his mouth and close it without saying a word Emily still snapped at him."Shut up and hold still," she commanded.

Emily began by applying a primer to the boy's face, the cool liquid spreading across his skin. She could feel the shiver run through his body at the sensation. Emily's hands were gentle as she spread the primer evenly, her fingers brushing against his skin that she thought was actually well taken care of considering he was a teen boy, she had known more than a few girls with worse complexions.

With the base done, she applied a layer of foundation, the makeup blending into his skin and giving him a smoother, even complexion. Tim could feel the weight of the foundation on his face, a new reminder of his feminization. He tried to keep still, but the sensation was both unfamiliar and intimate, making him squirm slightly, the entire time the pretty girl sitting so close to him and him not knowing where to look as she gave him a makeover.

Emily noticed his discomfort and smirked. "Hold still, Timmy," she said, her voice sweet but firm. "We don't want to make a mess of this."

Tim gritted his teeth, trying to hold still as Emily continued to apply the makeup and will himself to not let his eyes linger on her chest.

Meanwhile Emily moved on to the blush, sweeping the brush across his cheeks and adding a rosy hue to his skin..

"Ooh, look at that," Emily cooed, stepping back to admire her handiwork. "I’m starting to see a pretty girl. Maybe the time Timmy is too macho from someone like you."

Tim blushed at the comment, his face burning with embarrassment, it bright enough to show through the makeup to a small extent. He wanted to protest, to tell her that he didn't want any of this, but he knew it would only make things worse.

Next she moved onto the feminized boy’s eyes, applying a light pink shade with shimmer to his eyelids. She blended it carefully, her fingers brushing against his skin. Tim could feel the coolness of the eyeshadow, the sensation unfamiliar.

"Keep still," Emily warned as she applied mascara to his lashes, the brush tickling his eyelids. Tim tried to hold still, but having a dark wand come so close to his eyes made him blink and try to pull away.

Noticing his discomfort Emily smirked. "Hold still, Timmy," Her voice firm as she slapped his inner thigh gently. "We're almost done, next is eyeliner, it really help your hazel eyes pop."

Finally, Emily turned her attention to his lips. Holding his chin firmly from under his jaw, Emily pursed her own lips as her fingers squeezed his cheeks as she applied a bright pink lipstick to his lips.

The pressure of her fingers holding him still made Tim feel powerless as he felt the creamy substance rub over his lips, the entire process making him want to not just rub it off but to flee as fast as he could, but he had nowhere to go.

Still holding his face still, Emily’s eyes ran over his face, to examine her handiwork. Tim had soft features, more rounded than a lot of boys or at least she was pretty sure it was different than most boys, thinking about how boys would look in makeup wasn't normally something she did, but with Tim, she saw a girl sitting in front of her.

As the makeup portion of the evening started to come to a close Sarah held up one of the things she had found in the costume box that she had brought up. A pair of lifelike breast forms that irritated her a little bit with them larger than what she was able to grow. “Wow he… she is looking good but I think it is time we start working on her body.”