[TF/TG] My E-Girl - Part 2 (Commission) (Patreon)

Chapter 2 commissioned by SeriousSentence

~

To say Tyler was nervous was an understatement. Somehow, he’d let this whole crossdressing situation get way out of his control. It was one thing to dress up in the bedroom for his girlfriend, it was another thing entirely to dress up and appear on stream pretending to actually be another girl. Ever since her announcement in bed the other night Pip had been getting him to assume his Tiffany Tate persona more and more. Now it wasn’t just for sex, she was getting him dressed in the morning straight away and parading him around the apartment for hours, insisting he stay in character. So much so that the persona was becoming habit; he’d nearly died with embarrassment when they were at the grocery store; where after dropping his wallet he responded by giggling and saying ‘oopsie’. The lady in the aisle with them had given him such a look he wanted to melt into the floor and disappear. But then Pip had pulled him into the alleyway afterwards and kissed him so hard his head spun, telling him how hot it was and how sexy she found Tiffany. The mixture of praise and humiliation made his head spin and he didn’t know what or how to think anymore.

He knew he had to put a stop to it before the stream tonight. He just couldn’t appear online for thousands of people made up like that. His mind tortured him with scenes of his wig coming loose or his voice cracking, watching the constant stream of derogatory text filling up the screen as people realised he was really a man. He’d never be able to go out again, the internet and news would be filled with stories and discussions of PeachyPip’s weird, cross dressing femboy boyfriend. It was too much; his heart couldn’t take the embarrassment.

Tyler gripped the sink, looking at his own male reflection in an effort to build up the courage to say no to her. Pip was going to be so disappointed in him and that was the worst feeling in the world. He just had to push through it, she’d understand, right? He took a deep breath; he was Tyler, not Tiffany, Tyler.

Pip was in the bedroom as he entered, already dressed and prepared for the stream in her usual gothic themed apparel. A matching outfit of blacks, grey and pale pink was laid out on the bed ready for him; his cock twitched in anticipation and habit.

“There you are.” Pip smiled, “I have something very special prepared for your first stream. I got it online and it was very expensive so you’d better appreciate it!”

“Oh…I wish you hadn’t spent a lot on it.” Guilt was already seeping in.

“Nonsense.” Pip waved him off, “My girl deserves pretty things.”

“About that Pip,” Tyler licked his lips nervously, “I don’t think I can do this. Go on the stream. I love dressing up for you, really but I don’t think I can pretend to be Tiffany Tate for thousands of people. It’s too embarrassing, I’ll never be able to keep up the act.”

To his surprise, Pip didn’t look mad, on the contrary she looked at him with eyes filled with pity.

“Oh Tiff.” She cooed, “It’s just nerves! You’re going to be a star; I just know it.”

“No, really, I can’t humiliate myself-“

“You won’t.” Pip cut him off, “I’ve been training you for this since day one. Besides, think about how hot our sex will be after.”

Tyler felt his mouth go dry and his knees wobble a bit, how was Pip able to turn him on so easily? Already he could feel the desire, like a trained response, making his thoughts go sluggish.

“You get so turned on wearing these outfits for me.” She whispered, running a hand along his chest, “Think about how hard you’ll cum after being held at the edge for over an hour on stream.”

Tyler swallowed; this wasn’t how it was supposed to go. He was supposed to be a man, he had to stand up to her finally and tell her what’s what but he could feel his control over the situation slipping. Pip was so close now; he could feel her warm skin through the thin fabric of her shirt and his eyes kept ducking down to her cleavage. The outfits did turn him on, even if they were horrifically embarrassing. Maybe it was even the humiliation itself that got him hot. He was paralysed by his own confliction and Pip’s smile turned cool and victorious.

“Come on Tiffany, let’s get you dressed. The audience awaits.”

One last time, Tyler told himself, this would be the last time. The second things started to inevitably go wrong on stream, he was out and never becoming Tiffany again. At first, he wasn’t sure why the new clothes were so special, they looked like the standard fare; black and pink leather skirt, fishnets, knee high boots and a black top with a hole cut out for his cleavage but then he noticed the…extra attachments. The fake silicone breasts Pip usually had him wear to fill out the bust in his outfits had been replaced with far more detailed ones. Instead of plain, skin coloured rubber they were complete with pert pink nipples and beside them was an extra strip of flesh coloured plastic shaped suspiciously like a soccer cup. When he was fully naked Pip picked up the rubbery item and carefully placed it against his cock, pushing it back against his skin as the slightly sticky substance adhered to him.

“What are you-“

“As hot as it is to see your skirt get a tent when you’re turned on, we can’t have that happen on stream, can we?” She explained as though it were obvious, “Now your cock is nice and hidden, it almost looks like you really do have a pussy now.”

Tyler looked down at himself, the smooth expanse of fake skin between his legs and flushed a deep crimson; he looked like a barbie doll. He wanted to rip it off but knew Pip was right, at least now he wouldn’t give himself away in the most obvious manner. Gently she attached the breasts to his chest; they were bigger than usual and seemed to stick to his skin more closely. He could barely even make out the seams where silicone stopped and skin began.

“Oh, you look just darling.” Pip squealed.

“Aw, thanks girl.” Tyler responded before he could stop himself, feeling his cheeks turn even more red.

“See? You’re already getting into character, you’re a natural.”

Tyler just nodded, keen to get the clothing on to cover his rubber attachments. He was experienced now in many of the tricky aspects of getting dressed to be Tiffany; sliding on the fishnets, bra and panties took only a minute and lacing up the boots was second nature. He couldn’t help but notice there was something…odd, about the way the fabric felt against his skin. It seemed to almost hum or vibrate against it, sending strange warm tingles spreading through him.

“What’s this made of?” He asked, his voice slipping into his high, Tiffany cadence on its own.

“Something very special, some even call it magic.” Pip gave him a wink, “Don’t worry about it. Come on, let’s do your makeup, we’re starting soon!”

Tyler was in a daze, he almost felt drunk. His thoughts were coming slowly, as if through molasses and he couldn’t figure out why. The clothing felt good, right. He’d never felt more at home in his own skin and that idea was confusing to say the least. He watched as Pip painted his face, she’d really gotten good at hiding his masculine features; he swore his lips looked fuller and his face rounded than they ever had before. Maybe this stream would be fun after all, she’d done such a good job transforming him into Tiffany Tate even he couldn’t see any signs of fakery.

The tip of his tongue dipped out to taste the pink gloss across his lips. It tasted like sugar and made his stomach rumble. The final touch was the wig of course, his mousy brown hair disappeared beneath blonde ringlets, tastefully styled into a long-twisted ponytail. Just like the clothing this wig seemed to vibrate against his skull, it almost felt as though it was melting onto him, that was ridiculous though.

“Ready for your debut, Tiffany Tate?”

Tyler felt his mind slide backwards, relaxing into the back of his subconscious while another persona pushed forward. He turned and gave his girlfriend a sweet smile.

“Born ready, PeachyPip!”

~

Setting foot in Pip’s streaming room was like entering a sacred space. She often filmed all over the apartment but the streaming room was her sacred domain; fully dressed up and teched out to be the perfect space for her to perform and interact with her fans. Now there was a second swivel chair placed before the screens and cameras, waiting for Tiffany to take a seat.

He did so, self consciously running his fingers through the long hairs of the wig, gratified to see it didn’t shift even if he tugged at it. Already he could see the lobby of their stream filling up, so many people waiting for PeachyPip to log on for her weekly stream; Tiffany’s heart pounded in her chest. Pip swivelled the camera so she was the only one in frame and hit a button on her keyboard, her image appearing on the stream window as they went live.

“Hey guys!” She gave the camera a wink and a kiss, “Miss me? Of course you did!”

Tyler could feel his head pounding in time with his heart, it was so loud he couldn’t even hear what Pip was saying. Why was he doing this? This was such a mistake! Maybe if he was quick about it, he could sneak out before-

“And I have a very big announcement! I have a new co-host! Everybody, say hello to my good friend Tiffany Tate!”

The camera swung into his face and he opened his mouth, ready to introduce himself in the cutesy persona he’d been taught. But no words came out. Like a deer in headlights he froze, blinking like an idiot and watching himself on stream sitting perfectly still.

“Aw, she’s shy.” Pip gave him a quick hug, using the action to hide the sharp pinch she gave his thigh.

“Hi guys!” Tyler gave a little wave, “Sorry ‘bout that! I guess I’m just a little nervous is all.”

His head sunk down to his shoulders as he bit on a nail self-consciously in what he hoped was a cute manner; eyes glued to the chat stream.

‘Aw, she’s so cute’

‘Look at that rack! You got nuthin to be nervous about girl’

‘How did you guys meet?????’

They seemed to like him, so far at least. Tyler licked his lips; he could do this.

“I’m ah, so happy to be here.” He giggled, “I have always been such a fan of PeachyPip and to have her invite me was such a dream, especially ‘cause I’m nothing special.”

Adoration flooded through the chat and Tyler felt himself relaxing, that warm tingly feeling from the clothing seemed to be seeping through his skin down into the core of his being. It was sort of nice, being so adored by online fans, even the male ones who talked about how hot he was.

“So modest.” Pip sighed, “Now, I also have a surprise for you, Tiff?”

“Oh really?” Tyler clasped his hands together and gasped, funny, he didn’t even have to try to make his voice high pitched anymore it seemed to come almost naturally.

“Bobba tea!”

Pip reached under the desk to reveal two bubble tea cups topped with cheese foam and sprinkles. Tyler squealed with excitement, he loved bobbas, especially with extra sweetener.

“To answer your question Ransom356 we met at a bobba café.” Pip smiled, “Tiffany has quite the sweet tooth.”

Tyler was already sucking on the tea and managed to spill a few drops on his exposed cleavage while trying to reply causing Pip to scoff.

“She’s such a ditz I swear.” Pip laughed, “Clean yourself off Tiff!”

Tyler blushed, wiping a finger along the silicone skin to gather the sweet tea that had landed there, intending to pop the finger in his mouth so it wouldn’t go to waste but instead he froze. He could feel his finger against his breasts, properly feel it as though those tits were real. His eyes darted to Pip who was grinning, eyes glinting with a cold light.

“What’s the matter?” She tilted her head, pouting innocently, “Something wrong?”

He couldn’t say anything, not with the camera pointing at him like that.

“Um…ah…” He could feel the lace of his bra now, resting against his hard nipples, “You know what? It went straight out of my head. You know me, mind like a sieve.”

“Oh Tiff, it’s a good thing you’re such a cutie.”

Pip pinched his cheek and a giggle escaped him, what had he been so worried about a moment ago? It was getting hard to keep all his thoughts straight. Especially with this deliciously sweet bubble tea coating his tongue. Off camera, Pip placed a hand on his knee, gently running her thumb across the skin and sending warm streaks up heat up his thighs. Memories of the many hand jobs she’d given him while playing dress up bubbled to the surface and he felt pleasure start to pool in his lower stomach.

‘Poor Tiff, look how red she is. Maybe Pip should have waited to bring her online?’

‘Nah, I love that, girls are so cute when they blush’

‘I will pay $$$ to see her wipe tea off her tits again’

The knowledge that all these people were looking at and judging him made humiliation flare up inside, mixing with the lust. He knew this was a bad idea, what if Pip ripped off the wig and revealed him? God, he might die then and there. He was so embarrassed and so turned on he couldn’t think straight. Subconsciously he rubbed his legs together, pleasure blooming there as a subtle dampness began to leak through onto his panties. Was he sweating that much? No, there was something different about this wetness, it was thick and slick, leaking from his wet hole…

Wait, what? How did he…? Pip had said these clothes were special but surely they couldn’t do what he thought they were doing. Without thinking his hands few to hit tits, grasping them firmly, mouth falling open in surprised as he felt the fingers there brushing his nipples through the shirt. The seam between rubber and skin was gone; these breasts were real.

‘holy shit!’

‘That’s hot af’

‘Who has the bigger boobs? I think Tiffany wins out here’

“Tiff! What are you doing?” Pip laughed incredulously, “I know you love the attention but girl, have some respect for yourself.’

“Omigosh!” Tyler dropped his breasts, feeling them jiggle as they came to hang free again, “I’m so sorry I just uh, well I guess I just got caught up in my own head. My mind tends to wander.”

He was giggling, tongue stuck out with a wink to the camera. It just felt like the right thing to do and it seems the instinct was correct. Messages of adoration and quite a few lewd ones flew across the screen. He could figure out what was happening later; right now he had to keep up appearances and try to deal with his own horniness. The knowledge that below his leather skirt was a pussy aching to be touched turned him on, the fact that Pip’s hand was just inches from it only adding fuel to the fire.

Relaxing into the situation, Tyler felt himself let go, Tiffany fully in control. The words seemed to flow from his mouth naturally; answering viewers questions about his likes (cakes, pink, sweet teas) and dislikes (getting dirty and bitter coffee); Pip almost seemed to slide into the background of her own stream. Her attention seemingly focused on getting him as hot under the collar as possible. Her hands traced across his thighs and ass, the latter of which was now full and round like the peach she was named for. He had no idea how this was happening but he really was becoming Pip’s good little streamer girl and to his surprise it felt good. Yes, it was embarrassing as hell but he couldn’t deny the love his viewers gave him was gratifying.

“Well, that’s the hour guys!” Pip announced all of a sudden, “I am so glad you like Tiff, she’ll be back, don’t you worry!”

“Aw it’s over already?” Tyler pouted, “I wanted to talk some more.”

Pip’s hand on his thigh began to move upwards, only a finger away from his wet pussy now. God, he wanted her to touch him so badly, maybe it was a good thing the stream was ending.

“We can’t go giving it all away in one stream!” Pip replied, “Can we guys?”

The chat flooded with messages asking for an extended stream, Tyler felt himself flush when he saw how many people wanted more of him. Well, more of Tiffany. Pip gave the camera a kiss and wave, he did the same. The camera shut the stream off and almost immediately Pip’s finger slipped between his pussy lips making him moan.

“H-How…?”

“That’s for me to know and you to get used to.” Pip glared, “You’re my Tiffany forever, understand.”

“Yes, oh God yes.” Anything to make sure she didn’t stop.

Her finger was circling Tiffany’s new clit, making her hips stutter and moans escape. She’d been right on the edge all stream; she wouldn’t last long. At this moment in time, she didn’t care how Pip had done it, her mind was filled with nothing but bliss as more of that wetness leaked out of her as she got closer to the edge.

“Your job is to make sure I look good, understand?” Pip whispered, “If you do, I’ll reward you just. Like. This.”

Each word was punctuated by a strong stroke, Tiffany was seeing stars.

“Yes, Pip.” She breathed, “Please, I’m s-so close.”

“Cum for me baby.” She whispered.

Tiffany did; her whole body seizing as a wave of ecstasy like nothing she had ever felt as a man moved through her. She felt wetness flow over Pip’s finger, squirting out of her with each spasm of muscle and pleasure.

Tyler was a life left behind.

She was Tiffany Tate. A streamer who worked with PeachyPip.

That was all that mattered.