My E-Girl (Commission) (Patreon)

Commission for Serious Sentence

Tyler knew he should count himself lucky. He was lucky really; most people would kill to even hang out with PeachyPip let alone date her. A few months ago, he’d been just another of the thousands who watched her streams and socials religiously and now he was living with her. How an average guy like him had managed to win her heart was completely incomprehensible, all he’d done was take up the opportunity to carry her bags when he saw her shooting a video at the bobba tea place down the street. At first, she’d told him it was his quiet, respectful demeanour that had won her over, but after several weeks of dating he was beginning to believe she just liked having somebody there to carry all her stuff and film free of charge.

Tyler’s stomach growled and he bit his lip. He’d been hidden away in the spare room of their apartment for hours now while she livestreamed. Pip had made it very clear nobody could know they were dating.

“It’s important that my followers think they have a chance.” She’d explained the first time before shoving him into the spare room, “If they knew I was dating somebody like you, they might not tune in.”

What did that mean? ‘Somebody like him’? Somebody average probably. Pip was everything anybody could ever want; a platinum blonde with curves to spare and the outfits to show them off. Every day he diligently sat and helped her prepare the intricate hairstyles and costumes she was best known for. He was just plain, simple Tyler and every day he feared she would wake up and see it. After all, being the secret boyfriend of PeachyPip was one thing, being the guy who got his ass dumped by PeachyPip was even sadder. For this reason, keeping her happy was of the utmost importance.

Ultimately, that very mindset would be his downfall.

~

The outfit was incredible; A flared black skirt and matching crop top with a set of long arm length gloves and high heeled boots. Pip had laid out a number of silver chain belts and accessories to match it, and was standing over the outfit beaming.

“I don’t think I understand.” Tyler croaked, “You want me to wear this?”

When he’d first seen the clothes laid out, he’d assumed she wanted his help lacing up the boots or something, not this.

“C’mon baby.” Pip pouted, “It’s just a little fun. Our sex has been getting so vanilla lately.”

Tyler blushed; it had been great from his end. Now he felt even more inadequate, he should have known somebody as exotic and sexual as Pip would never be impressed by somebody like him in bed.

“Will it even fit me?”

“Oh yes!” Pip jumped up and down on her toes, making her heavy breasts bounce, “I made sure to get the right size.”

People dressed up in the bedroom all the time, right? Dressing up as an e-girl for his streamer girlfriend was a little extreme but it wasn’t like she was asking him to put on a gimp suit. And nobody was ever going to find out; it was a small price to pay for keeping somebody as amazing as Pip in his life.

“Okay then.” Tyler shuffled uncomfortably, telling himself the clothes were going to be ripped right off again within a few minutes anyway.

“Oh baby, thank you!” Pip grinned, if Tyler hadn’t known better, he’d have even said there was a sadistic glint in her eye. “Go on then!”

She sat herself down on the bed, arms and legs crossed with an expectant look on her face and Tyler flushed.

“I didn’t realise you were going to…watch.”

“Of course, I am.” She smiled, twisting a long strand of blonde hair between her fingers, “I want you to put on a show, babe. Make sure it’s a good one.”

“Couldn’t I just put the outfit on in the walk-in?” He tried, “Just the first time, it’s a lot all at once-“

“Oh, no!” Pip glared, “You’re going to put it on right here and now, understand?”

The look she shot him was icy, yet warmth bloomed in Tyler’s lower stomach. Pip was always quite dominant in the bedroom; it was part of what he liked about her. She wasn’t like other women who expected him to just figure out what felt good, she told him exactly what to do. It felt so good to find a woman to submit to who didn’t judge him for it. And right now, she couldn’t have been clearer.

Trying his best to ignore the feeling of humiliation he unzipped his jeans, wiggling them off his hips in a way that he hoped was suggestive. Pulling off his shirt at least let him hide his burning face for a few minutes and Pip clapped and cooed.

“Aww, don’t be shy.” She teased, “Look at those cheeks! Like a blushing bride.”

The comments only added fuel to the fire much to his chagrin, though he couldn’t deny that praise, in any form, from PeachyPip was like ambrosia to him. Kicking off his boxers he approached the bed, bending over to pick up the skirt and swallowing nervously. The material felt alien against the skin of his legs, it tugged at his hair uncomfortably and when he caught a glance of himself in the mirror he balked. The flared skirt looked odd on his square hips, giving the illusion of curves that simply weren’t there. While he was frozen, staring at his own strange reflection Pip snuck up and pulled the crop top over his head making his appearance seem even less appealing. The top was tight at the sides, but clearly missing the much-needed filling at the front, making it hang awkwardly. There was no way Pip could find him appealing, let alone sexy, dressed like this.

Much to his surprise though she wasn’t dissuaded, pulling up those long gloves and making him hold out his arms so she could slip them on before clicking on the many chains and belts.

“Are the heels really necessary?” Tyler squeaked, already feeling so embarrassed he was worried he couldn’t be able top get it up.

“Definitely.” Pip grinned, handing him the unlaced boots and sitting back to watch him struggle.

Why fashion moguls had decided boots and heels should mix Tyler would never understand. Even fitting his big feet into the shoes was difficult when the leather brushed his knees and tying the frankly ridiculously long laces took several minutes but when he finally finished, he let out a sigh of relief. At least now they could have sex.

“Time for finishing touches!” Pip squealed and that relief drained from him.

“Finishing touches?” His voice was so meek even he couldn’t respect it.

His heart began to beat faster as Pip produced several tubes of make up and compacts full of powder.

“You want me to wear make-up?”

“If you’re going to be my good little sissy e-boy, you need it.” She replied, as if that answer was at all acceptable.

If he were a man, a real man, he’d say no to this. Fuck, she’d just called him a sissy and instead of being insulted his cock had twitched in arousal! He should be saying no to this but the way she put emphasis on the word ‘my’ like he was some object she owned made his skin tingle. Having this hot woman, the apple of so many eyes, own him was a turn on to say the least. She shoved him down onto the bed, tube of lipstick in hand and with a gleeful smile began to apply it. Tyler could feel the smooth pigment staining his skin a deep red to match his cheeks.

Pip continued, applying mascara, eye liner and all manner of other pigments and powders to him, all while sitting he knees across his hips. Each time she leaned over he felt her breasts brush his chest and his cock twitched. She gave him a teasing laugh each time she felt it against her thighs but didn’t reward him by grinding down against it like he so hoped.

“Stay still, and then you get your reward.” She whispered, painting a tiny star on his cheekbone.

Yes. This was definitely worth the humiliation; he was sure now. As Pip snapped the last compact closed, he surged forward, achingly ready to begin but she stopped him, a finger on his now pouted red lips.

“Just a few more touches.”

Tyler felt like he was about to explode. Pip skipped over to a box in the corner he’d not noticed till now, opening it to reveal what at first looked to be a small snow storm of white fabric, broken up by a bright flash of blue. The white was an amorphous mass he couldn’t identify but the blue was undeniably a long-haired wig with curling waves. She strode back over to him, both in hand, diligently ignoring the way his new skirt was lifted by his hard cock.

“Stand.”

He did so, for a moment she dropped to her knees and Tyler felt the anticipation build, temporarily forgetting the items in his lust. But instead of a blow job, he was met with the scratchy feeling of stiff fabric against his thighs as she pulled a crinoline under his skirt, giving it extra volume. That flash of blue zoomed past his vision as she stood and suddenly, his dirty blonde hair was covered in neon blue.

“The crowing jewel.” She sighed, “Almost perfect.”

“Almost?” Tyler felt his heart was going to give out, just how long was this whole dress up game going to last?

Pip pushed him toward the mirror, forced to stare at his own ridiculous appearance while she rummaged in her dresser. With the wig, make up and outfit all working together he really did almost look like a real e-girl. He lacked the all-important curves but despite that he did look stylish; at least he could take solace in that to help keep the utter humiliation at bay. Pip returned with something made of soft silicone which she unceremoniously pushed into his chest and under the crop top. This should have been his breaking point; an outfit was one thing but fake tits? He swallowed, opening his mouth to tell Pip enough was enough but she silenced him with a soft kiss at the base of his neck.

Standing behind him so that he could see her in the mirror’s reflection, long arms shaking around his torso and bright hair over his shoulder; his knees went weak.

“You’re such a good boyfriend.” She praised, “I knew I picked well with you.”

The approval made his balls tighten; he could see himself in the mirror, skirt tented by his cock despite the layers of fabric beneath. Now that the outfit was fully complete, he realised there was a little lacy headband threaded through the blue strands of hair, that paired with the black and white girly aesthetic made the submission all the sweeter. Pip’s hands smoothed over the plane of his stomach, one coming to rest against the front of his skirt, palming his length.

“And because you’re such a good boyfriend, you’ll do anything to make me happy, won’t you?” Tyler could feel her hot breath on the shell of his ear.

“Yes.” He breathed; his cock was absolutely aching to be touched.

“You’ll play dress up like this for me again? Everyday?”

Tyler nodded, Pip undid one of the buttons at the waistband, allowing her thin hand to slip underneath.

“You’ll be my good little e-girl?” She teased.

“I uh…” It was getting hard to think, “I’ve got to keep my audience h-happy.”

Pip purred with approval, finally taking his length in her hand and gently stroking. Tyler moaned in both relief and pleasure, his desire had been building this whole time, he wasn’t going to last long.

“Perfect answer.” Pip whispered, “I want you to look at yourself while I do this.”

Tyler obeyed without hesitation; the pleasure of her touch was so great he didn’t want to do anything to risk losing it. With each slow pump he gasped, watching that pretty red mouth form an O and moan; he barely recognised the girl in the mirror as himself. His hips began to buck as he got closer, balls tightening further as he neared the edge. Fuck, he was getting turned on by his own reflection; he could see that blue haired girl slowly getting closer and closer to orgasm as her eyes glazed over.

“Careful now, if you stain your new clothes, I’ll need to punish you.” Pip teased, increasing her pace.

Tyler tried to hold back but it was impossible, he found his body arching back into Pip’s touch, unable to look away from the mirror as his whole body tensed. He was so close, there was no stopping it now.

“Say my name as you cum.” Pip whispered huskily.

He did. He cried out her name as hot seed burst forth, he watched as a stain appeared in the folds of the crinoline as he did so. White wetness, dripping between the folds. He shuddered, almost collapsing backwards and Pip finally stepped away.

“Oh f-fuck that was…”

“Very good.” She finished for him, “But, you did stain your new clothes.”

Was she serious, about punishing him? Tyler’s stomach churned at the idea, half turned on and half concerned.

“You’re going to wear them, till they dry.” She nodded, “I want it to really sink in, what these clothes did to you.”

Tyler blushed, there were worse fates he supposed. Again, nobody but Pip was going to see him anyway and she was clearly getting off on watching him. He owed her after that amazing hand job. And if he was honest, fake tits aside, he did look pretty cool, even if he did look like a girl. It was all just for fun, pretend. Nothing to be concerned about.

~

Tyler had been hoping the taunts of playing dress up every day had been just that. Taunts. When he walked into the living room the next morning to see another outfit meticulously laid out for him, his stomach clenched. Immediately his system was flooded with adrenaline and conflicting emotions; arousal and humiliation chief among them. This one looked like something out of a Hot Topic catalogue from ten years ago, all pink and black plaid and silver buckles, his eyes were immediately drawn to the fishnet stocking and swallowed.

“Good, isn’t it?” Pip smiled, “You’re going to look so adorable.”

“It is not a compliment for a man to be called cute.” Tyler mumbled only to be met with an icy glare.

“But you’re not a man, are you?” Pip said in a low voice, picking up the skirt and holding it against his hips, “You’re my good little e-girl. Because that makes me happy and you want PeachyPip to be happy, don’t you?”

She was using that dominating, oh so sexy voice that made his knees wobble and mouth go dry. Memories of that girl in the mirror yesterday bubbled up inside him and his cock twitched. Submitting to her touch in that sexy outfit had been so hot, maybe doing it again wouldn’t be so bad. Nobody was going to find out and she’d get sick of dressing him up and pleasuring him eventually, right?

“Yeah, of course.” He swallowed again trying to wet his dry tongue, “I’m sorry Pip.”

“Sorry isn’t good enough, you’ve made me sad.” She pouted, “But that’s okay, because I know just how you can make it up to me.”

Tyler smiled tightly and took the skirt, slowly unbuckling his belt to put it on. The pink made this outfit even more embarrassing than the last and putting on the stockings was near impossible. In the end Pip had him sit, leaning back on his hands and extending one leg in the air at a time so she could slip them on him. Tyler had never blushed so hard in his life.

“Oh, what a cute pose that is. I’ll have to remember that one.”

That comment seemed ominous but Tyler didn’t have time to focus on it; the blood was rushing to his cock as Pip ran her fingers along the waistband of the stockings, ensuring they were even along his hips. Pip seemed to delight in getting him ready as slowly as possible, applying the make up with a light hand so that he had no choice but to sit still and endure the soft tickle of brushes against his skin while his erection got harder and more painful. By the time he was fully decked out, black wig with pink skull pigtails and matching goth make up applied, he was ready to scoop his girlfriend up and plow into her right there on the living room floor.

Unlike yesterday though, this time she took a step back, eyes roaming up and down his body with an approving nod before sitting back on the couch.

“Now then, let’s practice your demeanour.”

“My what?”

“You’re demeanour.” She repeated as if it were the most obvious thing in the world, “You look like my good little e-girl, but you don’t carry yourself right and your voice, well, that certainly breaks the illusion.”

A cold sweat formed on Tyler’s back.

“We’ll start with something easy.” Pip pointed her index finger into her cheek, tiled her hair and hummed while looking skyward. It was a cute ‘thinking’ gesture he’d seen her make a hundred times on stream.

Did she serious expect him to do that? The serious look on her face when she stopped told him she did.

“This is too much, it’s one thing to dress like a girl but acting-“

“It’s not acting, it’s who you are.” Pip corrected, arms crossed, hard glare boring into him. She was really taking this roleplay stuff seriously. He really didn’t want to make her mad, or worse, disappointed.

Shame burning through his entire being he copied the pose, his hum coming out squeaky and wrong due to nerves.

“You can do better, try again.”

He did so, figuring the faster he got this right the quicker he could get laid but every time he mastered one pose Pip proposed another. He made his voice higher and breathy; she made him practice various sayings similar to the ones she used on her own streams. Once he had that down it was on to the gestures, some were so complicated they were almost full on dances. He blushed as she ordered him to stick out his chest and ass more.

“You have assets down! Use them!”

It was so exhausting posing and jumping around that he ran out of energy to be embarrassed. Leaning over with his hands against his knees and a playful grin, Pip clapped approvingly and he felt warmth bloom in his chest, despite the cool silicone breasts. It was good seeing her happy and the poses and affectations she made him do weren’t that bad really.

“Hey guuuuurl.” He purred, sticking out his tongue with a wink, Pip bounced on her heels.

“Perfect! Just perfect! Didn’t I say you would have fun doing this?”

“Totally.” He giggled before he could stop himself, this act was going to his head.

“Who’s a cutie?”

“I’m a cutie!”

The pair of them fell into a fit of giggles, after so many hours the motions and affectations were becoming second nature. It was still embarrassing as hell but so long as Pip was the only one seeing him emasculate himself, he didn’t mind too much. Anything to keep her happy with his sorry vanilla self.

“Now, I think you’ve earned yourself a reward.” She whispered huskily.

He barely lasted a minute.

~

Turning into a girl for Pip’s amusement was becoming a daily occurrence; each time she’d prime him with gentle touches and inuendo ladened words until he was so horny he couldn’t bring himself to care about the embarrassing outfits. While the method wasn’t exactly his cup of tea, Tyler had to admit the sex he’d been getting had never been better and sometimes she even wore a matching outfit. He was living the dream, the most popular streaming e-girl in his bed doing unspeakably good things to him. If playing dress up and acting a little ditzy was what it took, he’d do it.

So, when he walked into the kitchen one morning to see an elaborately decorated slice of strawberry cream cake sitting next to a new outfit, he knew exactly what to do. Sliding into his ditzy valley girl style persona was as easy as breathing after all the practice.

“Oh, so cuuuuute!” He made sure to push his palms into his cheeks for emphasis, Pip gave him a proud smile; he was getting the hang of this, she barely had to tell him how to act anymore.

“And it’s all yours.” She purred, “Once you get dressed of course.”

He giggled to cover the way his stomach growled, cake for breakfast wasn’t the best but he couldn’t deny the dessert looked delicious. There was even a perfectly placed strawberry right atop a dollop of whip cream as decoration, it was like a painting.

The outfit was nothing particularly outrageous either, the usual hot topic meets modern goth aesthetic she normally had him wear with one distinct difference. A pair of simple blank bikini brief style panties. Normally, he wore no underwear at all, it seemed counter to the eventual goal of sex. They were fairly simple though and he wasn’t one to complain about free cake and sex, he didn’t hesitate to put them on before turning to the rest of the clothing, much to Pip’s delight.

He had noticed she’d been adding more ribbons and other girly accessories lately. This time it was little strawberries to match the cake; hanging from his belts, braided into the pink wig and even patterned across the fingerless gloves. He slipped them on and posed for her appropriately, lapping up the praises she gave him.

“Which nail polish?”

Pip held up two tiny bottles, one black, one pale pink; this was an easy one.

“Pink of course! You know it’s my colour, girl!”

“That it is.” Pip’s smile looked almost sinister.

“Apply it for me?” He asked, biting down on his knuckle, “You know I’ll just spill it everywhere, I’m so clumsy.”

Pip gave him a pat on the head that sent warm tingles spreading through his body.

“Of course. Now hold still.”

He spread out his hand accordingly, letting her paint his delicate nails; he’d started filing them to half moons as she’d suggested, it made the process much easier. The sugary smell of the cake made his mouth water; he was starving. It had been forever since Tyler had eaten cake, he gained weight so easily he had to be careful with sweets. He’d worked hard to get out of his pudgy stage in college and didn’t want to risk backsliding, but one piece of cake wouldn’t hurt.

He raised his finished nails up to admire them before blowing on them gently to help them dry. He’d seen Pip put tiny stickers on her nails in the past, idly he wondered if she had any strawberry ones, that would really bring the whole look together.

“You look fabulous.” Pip praised and he blushed.

“Aw, thanks babe. Can I have the cake now?”

“Sure thing, sweets for the sweet.”

He couldn’t stop a giggle escaping at that. Licking his lips, he picked up the tiny silver fork beside the cake and took a mouthful. The sweet cream and sponge practically melted on his tongue and he moaned.

“This is so yummy, thanks so much Pip!”

“Only the best for you.”

She stood behind him as he ate, rubbing his shoulders and Tyler sighed in contentment. This really was the perfect life; it simply couldn’t get any better than this. The cake was so good it was only hours later, in the shower that he realised they never had sex.

~

Pip was having the time of her life. Tyler, her wonderfully submissive little guy, was turning into her best project yet. Watching him squirm under her gaze as he put on that first outfit had been so incredibly hot but even she couldn’t have foreseen how easily she’d be able to get him turned on by the idea. Pip had been expecting this plan to take weeks, if not months to slowly implement but instead she was almost ready for phase two after a matter of days.

Every day she presented Tyler with a new outfit, each more outrageous than the last. He was still a bit embarrassed, poor thing, always hesitant but in the end she had him crying her name as he came, camisoles and leather be damned. She had him thoroughly programmed now to associate the outfits with sex; sometimes he started getting hard before she’d even helped him into the skirt. It was so strong she’d even noticed the ditzy affectations she’d had him perform were slipping into his regular vernacular. The first time she saw him bite his finger while trying to decide which coffee to buy at the café she almost came.

She’d also started priming his with desserts and treats, she knew deep down he had a sweet tooth and she used that knowledge to her full advantage. She’d secretly taken a number of photos of him all dressed up, dainty spoon in his mouth as he ate. You couldn’t even tell he was really a man under all that make up; she’d really outdone herself. And so, on the seventh night, as she was putting the finishing touches on her latest creation for him, she decided it was time.

“I’m going to introduce you to my audience.” She beamed, snapping his knee-high socks into place.

“Really?” Tyler’s eyes were already blown wide with desire, she’d made sure to really tease out this outfit change so he was good and pliable for the announcement. This outfit was the girliest yet, all pink chiffon and pearls; not remotely her usual fare but it worked wonders as emasculating him. It had been a final test of sorts and while he’d initially blushed, he was so used to this now that was the only hesitation she’d seen. He hadn’t even flinched when she’d tied a pretty pink ribbon around his neck, a perfect match for his glossy lips.

“Yup.” Pip popped the P on the word, “You’re going to be my new co-host, dressed just like this.”

Tyler balked.

“Oh n-no I don’t think I could-“

She silenced him with a deep kiss, the gloss on Tyler’s lips tasted of strawberries. Pip pouted as she pulled back, giving him a look she knew he could never resist.

“But Babe, it’ll be so fun.” She whinged, “It’ll be our little joke that you’re not really a girl. Nobody will be able to tell the difference. We’ll call you Tiffany Tate.”

“But…but-“

“I thought you said you’d do anything to make me happy.” She continued, pushing him down onto the bed and crawling up his body, “Plus, you look so sexy dressed like this. I want to share you with the world.”

She could see the hesitation still shining in his eyes, so Pip pushed back the leather skirt she’d dressed him in, palming his cock. She made sure to keep a little of the fabric between them, ensuring the skirt itself bought him pleasure. She watched as his eyes began to glaze, he truly was helpless against her.

“O-Oh…”

“You’re my good e-girl aren’t you? You want to make your viewers proud, don’t you?” She teased, making her touch lighter before moving forward, pushing back the skirt fully to position her wet hole against the tip, “What do you say?”

“Oo-okay.” He shuddered, Pip grinned victoriously and sank down on his shaft.

She moaned, letting the hardness penetrate and stretch her inner walls, revelling in the feeling of his tip brushing her G-spot before beginning to roll her hips. For a minute she closed her eyes, letting herself marvel at the sensations before looking down at Tyler writhing beneath her. She’d dressed him in a punky, almost entirely pink, and black leather ensemble tonight, highlighted with a pink wig and bright girly make up. If it weren’t for the cock she was currently riding, she could almost believe he really was another streamer girl.  His pink, pouted lips were glistening with saliva, forming a cute little O as he struggled to hold on. She knew he was close but he wanted to hold back to please her, such a good boy. At least for now.

She had him curled around her little finger, the power was intoxicating. She began to bounce on his cock, riding him hard and enjoying the control she possessed. She could make him do anything.

“Tell me you’re my girl.”

“I-I’m your girl.” He was getting closer; she could feel it.

“What’s your name?”

“Ty-Tiffany Tate.”

“Good girl!”

His eyes sparkled with lust; she knew what her praise did to him. Fuck she was getting close too, watching him melt under her touch, it was so hot she could barely stand it. Her inner walls were squeezing around him and she could barely even give orders, the words turned to moans in her mouth. She gripped onto his shoulders as she got closer, remembering how hot it had been to watch him that first night cumming into that skirt as she pumped his cock. She shuddered, pleasure exploding inside her as she came, milking him for all he was worth as she felt hot cum flood her. She sighed, enjoying the sensation for what she knew would be one of the last times. If everything went to plan for her stream tomorrow, Tiffany would be cumming in a very different way from now on.