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The bright summer sun shines down onto Michelle, Jal and Cassie’s shoulders, their sunglasses shading them from the bright light. As the students leave class and pour outside onto the bustling London streets, they eye each of them intently.
“Him?”
“Nah, hands are too muscular.”
Last week, Jal’s dad hosted a party in some fancy bar downtown. Jal ran out pissed from her dad starting a fight and stumbled into another bar. While viewing a cocktail menu, something caught her eye.
‘LADIES NIGHT! GIRLS DRINK FOR FREE (MUST BE GROUP OF 4) PARTY MUST BE ALL WOMEN. NO EXCEPTIONS!’
Jal’s eyes sparkled. But she only knew three girls including herself.
The next day, she mentioned it to Michelle, then Cassie. Each of them both only knowing each other, the search for the fourth girl began. Slowly but surely though, they all realized how horribly annoying every girl in their town is. They’re either strangers, or have some unspoken drama between them. Then, Cassie jokingly said,
“We should just put a wig on Tony and bring him instead.”
At first, they laughed. Tony was too tall, and although he’s pretty, he’s got his flaws. He could also probably get free drinks from anywhere if he really wanted to. But the longer they thought about it and the more dead ends they hit, it became a real possibility.
Could they really sneak a guy in?
That leaves them with Maxxie, Anwar, and Sidney. Anwar would never. Maxxie has dance rehearsals. Sidney…
He has crumbs from lunch on his shirt, his beanie is barely on his head, he’s slouching, his shoes are untied, but his hair is long, he’s fit, he’s short and he’s got a good face under all that.
Sidney would– no, he will. He’d do anything to make Michelle happy. And she wanted free drinks. So free drinks she will get.
Jal and Michelle instantly perk up and look at each other. No words need to be exchanged before they’re speed walking over to him.
Sid catches whim that Michelle is walking towards him, faster than ever before. She’s clearly got something on her mind based on the smile on her face. He straightens up and awkwardly waves to her. Oh, Jal is here too.
“Sid! Do you want to go out with us tonight?”
Michelle asks although she already knows the answer.
“Just us. You, me and Jal –and Cassie. ”
“Alright. Where’we going?”
“There’s a bar downtown that’s having an event. Free drinks all night.”
Jal and Michelle nod.
“My house at 10?”
Sid’s eyebrows raise, and that’s all it takes.
—-
The room is dimly lit by LED lights. Clothes are scattered around the floor, the closet swung fully open. Michelle pulls up her tube top, then pulls it back down a bit to show her cleavage. Jal does her mascara in the mirror, while Cassie, who’s been ready since the afternoon, sits on Michelle's bed.
“How are we gonna tell ‘em? We can’t just drug him and make him wear ladies clothes.”
Cassie says, legs crossed and picking at every loose string on Michelles blanket.
“Cas, he’ll do anything Michelle asks. And Michelle better ask.” Jal looks at Michelle.
Michelle smiles. A knock and she runs to the door. She slides from her tights on the hardwood floor before opening the door to a poorly dressed Sidney. He couldn’t be more underdressed and more happy to see Michelle.
“You look… great.”
He says, his arms to his side. She pulls him inside. He’s tense, he’s never gotten this much attention from girls, let alone the one he’s deeply in love with. She leads him to her room, a first for Sid, and the girls look up to their victim.
“Hey Sid.” Cassie smiles. “We’re going to make you pretty now, yeah?”
“What?”
Michelle panics. “Cassie– Sid. Remember when I said– about that bar with the free drinks.”
Jal stands up and walks to the closet.
“This stuff might be a bit tight on him, ‘Chelle.”
She pulls out a gray tank top with a rhinestone pattern.
“I like that one. With a skirt and my thigh high stockings.”
Cassie giggles, unable to contain her laughter. The girls all look at Sid as Jal nudges the shirt towards him.
“Why’re you looking at me?” His eyebrows knit together, confused. “I think what I got on is fine.”
“Sid, you want free drinks, right?”
Michelle stares at Sid, batting her eyes unintentionally. Sid loses his breath just at the sight of it.
“--Yeah.”
“I think we should change your outfit, the dress code’s a little modest.”
Jal throws the tank top at him while she grabs for a skirt and socks. She finds a short, tight purple skirt with black stockings.
“Jal, these are girls' clothes. Why would I wear—”
The girls look around the room. Something’s up. Sid did find it weird how they invited only him out and not the other guys. But he thought they just woke up and suddenly decided he was attractive and wanted to get him all for themselves. Clearly this wasn’t the case.
“The bar we’re going to… it’s free drinks for girls only. And we needed a fourth girl. So…”
“What?” Sid tenses. “Do you guys think I’m a girl–”
“No! Obviously not.” The girls shout. Cassie looks him up and down. “Well–”
“No, Cassie. Sid, listen. Jal saw this bar was giving out free drinks tonight to groups of girls, but we only had three girls and needed a fourth.”
“We were hoping you would let us give you a little makeover to get free drinks.”
Jal blurts out.
“And you’ll get free drinks too. And go out with ‘Chelle.”
She nudges Michelle’s shoulder. Sid looks around, speechless.
“You guys are absolutely mental.” Sid turns to walk out when Michelle grabs his arm.
“Please. It’ll be fun. We know how to have a good time.”
She looks around the room. “Plus, I think you’d look really good in my clothes.”
Jal raises the skirt and tights, showing them off. Sid sighs deeply. He stares at the ground for a second before shutting his eyes tight. He looks up.
“You cannot tell anyone about this, yeah? Not a word– especially to Tony.”
The girls all promise. Cassie just giggles.
“Okay, fine.”
Sid gives in. How can he say no to Michelle? The second he answers, Jal and Michelle jump up and get started. The girls sit him down on the bed, taking off his beanie and sweatshirt. Although, he wishes they were doing this under other circumstances.
The girls take turns putting on eyeshadow, blush and lipstick. Cassie gets started on his hair, she teases it a bit and brushes it out. Sid just sits there in his head thinking about how absolutely plastered he’ll be soon.
“Do we paint his nails?” Cassie asks.
Sid objects but Michelle says yes. Whatever Michelle wants, she gets. She goes with a dark purple color, and applies it neatly on. Sid holds up his hands in front of his face, admiring it.
The last thing was his outfit, which consisted of a gray tank top, short skirt and knee-high sheer socks with sneakers. Maybe some rings and bracelets too. Sid was fully flushed at this point. He walks into the bathroom to change, seeing himself in the mirror. He makes a disgusted face as he pulls his shirt over his head and swaps it with the tight tank top.
Michelle knocks on the door.
“Sid? We forgot something, here.”
She opens the door just a crack and hands Sid a bra and panties– no, her bra and panties. It’s pink and has a shit ton of padding inside– the underwear is a dark red cheeky cut, enough to ‘fit’ him in it.
Sid lets Michelle’s hand wait there for a moment, unable to process what’s really happening. Finally he grabs it from her and she closes the door, giggling.
Sid sits there in silence staring at the pieces of fabric. He doesn’t know which he’s getting more worked up over, the fact that this is Michelle’s intimates or the fact that he has to wear it. Either way, he tears up from embarrassment and swallows his shame. How the fuck do you even put a bra on?
He throws the tight tank top over the bra, an unusual feeling washes over him and he turns around to the mirror. He makes a face as he adjusts the shirt, pulling it down to reveal the top of the bra. Sid groans at the sight of it. He looks down to Michelle’s underwear on the sink.
He unbuckles his belt and lets his pants fall to the ground, delaying the process as much as he can. He sighs and shuts his eyes, like if he can’t see it then it’s not really happening. He quickly undresses and switches their underwear, the fabric meeting uncomfortably with him. He cringes and quickly puts the skirt on over it.
The feeling makes his heart race. His hands become clammy as he grabs the stockings on the floor.
Sid sits on the toilet and rolls up the stockings to his thighs, a glimpse of Michelle’s underwear peeks through his thigh, making his stomach turn. His face is red hot as he looks into the mirror. The girls knock on the door impatiently.
“You alright?”
Jal asks, she backs away once he slowly opens the door and shyly walks out to all the girls. They all glance towards him, staring in awe.
“Sid, you look…”
“Like a whore?”
“No, nono, you look really pretty actually… like a girl.”
Sid blushes.
“Shut up. Let’s just go– and give me my hat.”
Sid grabs his beanie from Michelle's hand. The taxi waits outside and they head out.
The taxi is cramped. Michelle’s leg rubs up against Sid’s after every bump they hit. It sends a weird feeling to his stomach. The taxi driver glances at the girls in the back, Sid included. He keeps licking his lips and awkward eye contact is made between them. Gross.
“Now, Sid, you gotta work on your lady voice.” Jal turns to him.
“What if we just say I’m mute and can’t talk?”
“Who’ll believe that? C’mon, give us a girl voice.”
Sid considers it for a second, then when the girls stare at him amusingly, he looks out the window flustered as they laugh.
“I hate you guys.”
Michelle turns to Sid and rests her head on his shoulder. “Thank you for doing this, Sid.”
Sid’s eyebrows raise and he sighs as he leans into her touch.
———
The taxi stops in front of the bar. Everyone gets out and adjusts themselves, Sid pulls his skirt down which only exposes his stomach, he can’t win. They take a peek at the line, which they can’t see the end of. Everyone's eyes gravitate towards the group, Sid gets embarrassed and hides behind Michelle.
Jal walks up to the bouncer, she chews her gum with confidence.
“We’re here for Ladies Night.”
She holds up her ID.: JAL FAZER
The bouncer looks at her up and down, before smiling sweetly.
“Nice to see you again, Ms. Fazer. Enjoy.”
Jal walks in. The rest of the girls giggle in disbelief. They’re actually in.
“Why’re you walking like that?”
Sid gives Michelle a look before she realizes.
“You could always take them off.” Michelle smirks.
Sid rolls his eyes.
“Where’s the bar?”
Jal walks them to the counter and just like she said: “Party of 4+ women drink free!” The sign stares all of them in the face.
Sid eyes the bartender, they make eye contact. He gets nervous that he’ll see right through him and kick him out and everyone will make fun of him. Before he has any more time to panic, the bartender walks over to their group.
“Welcome ladies, what can I get you?”
He doesn’t look at Sid when he speaks to them all. Sid’s nerves grow deeper in his stomach, he might throw up before he even gets drunk.
“A round of shots please. Strongest you got.”
“You got it.” The bartender finally looks over at him. “Think you can handle it, lass?”
They all stare at him, Sid clears his throat to speak. He just smiles and nods.
“She’s the heaviest drinker out of all of us, give her the hardest you’ve got.”
Jal talks to the bartender. He gives Sid an excited; almost seductive look as he turns his back to pour the drinks. Michelle whispers to Jal,
“I can’t believe it’s working… We deserve extra drinks for pulling this off.”
The girls laugh to themselves before turning to Sid, who is being eyed by every single guy in the bar. His back is turned to them all, he fidgets with the loose piece of wood on the bar and occasionally adjusts his shirt.
The shots finally arrive at the table. They’re gone as soon as they arrive. It burns going down, and they all make a face. Sid shakes his head vigorously to try and ease the burn, it doesn’t work– they recover and laugh it off.
“Another round please!”
Jal calls out. As they make conversation, they all decide to head to the dance floor. Michelle holds her hand out to Sid. He waits a second before hesitantly accepting her invitation. She pulls him violently into her and the two begin to dance to the booming music.
The men around the bar watch the group as they dance, Sidney takes notice and begins to get shy. He goes back to the bar and downs another shot. Just as his hand slams down onto the bar, a big, wrinkly hand brushes up against his.
Sid jerks up from the sudden touch, he meets the gaze of an older man. His skin wrinkles into a smile when Sid locks eyes with him, Sidney’s eyes widen in shock– it’s his dad.
“Can I get you a drink, darling?”
He is clearly shit-faced. Mark leans into Sid’s ear to speak, Sid shivers and backs away to Michelle and the others. But before he’s lost in the crowd, Mark grabs Sid by the wrist and pulls him into himself.
Their bodies meet as Sid feels his dad’s hand slide up his body to his fake, padded chest– a grotesque emotion fills Sid’s body and he elbows his father in the stomach. Mark doubles over in pain as Sid manages to get away but not before turning around and slapping Mark in the face.
“So gross, dad.”
He mumbles as he slips through the crowd back onto the dance floor to find the girls.
––––
Shots and shots after shots, and cocktails, margaritas, beers, speciality menu drinks, Sid drank as much as he possibly could. When was there gonna be another time where he could drink for free?
As rare as the occasion was, he might’ve gone a little overboard. His vision is blurry and he can barely form a coherent thought– and these stockings are way too tight around his thighs.
The gang walks outside together. Sid wobbles, his makeup smudged and messy. The sun peeks through the very start of the horizon, but the night still fills the sky. Michelle looks over to the staggering Sidney. She locks her arm with his.
“Thanks again for doing this.”
Sid smiles weakly, trying to focus on walking without falling over.
“S’right.”
He did have a good time. Yes, it was horrendously embarrassing and he got touched up by his own dad thinking he was some random chick, but he got to drink as much as he wanted for free so, whatever I guess.
Sid feels his stomach catch up with him and clutches it. He stops walking and Michelle turns back.
“You okay?”
“Yeah. Just gonna sit down for a second.” He winced between words. The vomit was inching its way up his throat.
“You guys go.”
“What? No–”
“Your mom’s gonna kill you if you’re not in bed when she wakes up– please. Sid’ll be fine. Right, Sid?”
Jal protests. Sid gives a thumbs up, still clutching his stomach. Jal and Cassie walk on, Michelle kneels down to Sid’s level. She cups his face and brings her lips to his cheek. It leaves a wet mark.
“Get home safe, okay? I’ll pick up my clothes tomorrow. Unless you wanna keep ‘em.”
She jokes, Sid playfully nudges her away. Michelle catches up with Jal. Sid smiles as he watches her, his excitement from Michelle’s touch numbs the feeling of nauseousness for a moment.
His head spins as he groans and shuts his eyes. He sits for a bit, regretting the liquor intake. People walk past and throw cocky names at him, but his head stays down.
He can’t hold his liquor anymore and leans on a brick wall for support as he spills his guts. He groans and spits up what’s left in the back of his throat.
He wipes his mouth against his arm and composes himself. The thought of laying in bed is the only thing that keeps him going. The girls are far gone now, it’s up to Sid alone to get home.
As he looks around his surroundings, he recognizes some buildings and streets from his walks around town. The mental map in his brain barely laid out, he stumbles home.
—---
The sun’s light passes softly through the trees as Sid arrives home. Walking felt like ages, and with such a ridiculous outfit– he desperately wants to take it off. He grabs onto the front door knob and turns, not bothering at all to keep quiet.
There is a familiar smell in the air. His eyes barely open as he walks to the staircase up to his room. The stairs creak loudly, and he walks up them painfully slowly. Sid is still shit-faced drunk, but the motivation to simply be in bed was all that was keeping him from passing out on the streets like a hooker.
He finally makes it up the stairs and to his bedroom. He smiles to himself from just thinking of undressing and being under the covers. His bedroom door swings open, and there stands Tony.
Sid squinks and rubs his tired eyes. He looks around his bedroom, but only, it’s not his bedroom. It’s Tony’s bedroom– this is Tony’s house.
“I was wondering who was coming up the stairs– didn’t expect it to be a cute girl…”
Tony’s lips press together into a smile as he looks Sid up and down. He stands at the edge of the bathroom door in a t-shirt and pajama pants.
His comment sends shocks to Sid’s brain and he can suddenly feel the tights squeezing his thighs again. He adjusts them and moves around awkwardly, trying to cover himself with the air around him. Tony begins to walk over–
“NO– No. It’s me, Tony, it’s Sid.”
Sid stiffens up to give Tony a clear view of his face, Tony stops in his tracks and stares, annoyed. He gives Sid a face as he walks to the window, holding a cigarette to his mouth.
“Why’re you still up?”
Sid nervously asks, almost insultingly. Tony lights it and turns back around, ashing it out the window.
“Exam tomorrow– well, today. I was studying. Clearly you… weren’t.”
Tony cockily smiles to himself.
“Shit. I thought I was walking to my house.”
Sid feels Tony’s stare on every exposed inch of his body, he can’t even imagine how stupid he looks right now, especially to Tony. The dizziness washes over him again, this time harder than ever.
Maybe it’s because he hasn’t had anything but alcohol in the past two hours, but his body is slowly giving up on itself. Sid wobbles towards Tony’s bed and presses a heavy hand onto it to break his fall. He can feel his stomach turning again as his head lies against the mattress and his body falls to the ground.
“Please don’t puke on my bed.”
Tony ashes his cigarette and plucks it out the window. He walks over to sit on his bed– he glances down at his miserable friend.
Sid can’t look Tony in the eye. He shuts his eyes to try and stop the dizziness, his eyebrows furrow together from the strange sensation in his head. No one speaks for a while until–
“It’s…a long story…’s the girl’s idea.”
“You were out with ‘Chelle? Where’s my invite?”
Tony furrows his brows, jealous. If only he knew what he’d had to do to be invited. Tony looks down at Sidney. He debates mentioning it but decides: of course he will.
“Did they put you in this?”
Tony slides a finger through the top of Sid’s tank top and lifts the fabric. Sid brushes his hand away and flops his head right next to Tony’s thigh. Tony takes this as an opportunity to see Sid completely, how the stockings squeeze his thighs and legs, the skirt riding up his legs, and—
“Sid…are you wearing ‘Chelle’s bra?”
Tony snickers as he grabs Sid’s padded chest and squeezes. Sid snaps awake and covers up as much as he can, embarrassed again. He swats away Tony’s hand, the sudden exertion makes him give out as he falls on the floor onto his back.
A wave of whiplash as his head slams into the ground. He groans in pain– without thinking, he cradles his knees towards the ceiling and his skirt reveals Michelle’s underwear.
Tony shamelessly stares through Sid’s legs, squinting to himself.
“No fucking way.”
He mumbles to himself before getting up and staring down at his limp friend. His foot makes its way towards Sid’s skirt– brushing up against the fabric and slightly lifting it to reveal more of him.
Just as he thought, Michelle’s underwear.
Tony scoffs to himself in disbelief and amusement. The scene is just too much for Tony to not do anything about.
Sid lays barely conscious on the ground groaning. Tony sighs, he leans down and grabs Sid’s wrist and attempts to pull him up. Sid struggles against his efforts,
“Sid– help me out here.”
Tony wraps his arm underneath Sid’s armpits and lifts him to his bed. He flops Sid down with a heavy exhale.
Tony looks down at the scene below him. It’s almost comical how perfect the situation is– your drunk best friend, who you’ve had weird sexual feelings for, is lying dressed as a girl in your bed.
Just as Tony is about to say something, Sid moves his hand to the back of his head and rubs it. He whines as he opens his glossy eyes and looks around.
“Ow.”
He innocently mumbles. Tony replies by crawling in next to Sid, his body inches away from embracing his friend, their bodies fit into each other perfectly. Sid turns onto his back and stares up at the ceiling, Tony eyes Sid for a bit before he lays on his back with him.
“Are you gonna explain to me why they dressed you up like a girl?”
Tony says softly. Sid, still wasted, mutters out a reply.
“...They told me I’d get free drinks if I was a girl… so, they….”
Sid moves in and out of consciousness, his exhaustion catching up to him with every slow blink. The room spins slightly as he closes his eyes and drifts to sleep, but sounds of rustling next to him startle him awake. Sid looks down to where the noise came from, Tony is no longer next to him. Instead, Tony kneels at the edge of the bed by Sid’s feet. Sid sits up on his elbows,
“What’dyu doing?”
“I don’t want your shoes on my bed, they’re all muddy. Mum just washed the sheets.”
Tony rips Sid’s shoes off and tosses them towards the closed door. Sid’s legs hang off the bed, his feet now only covered by sheer black stockings. Sid’s feet stretch and ache, he’s clearly uncomfortable. He flops back down on his back.
“Can you take these–
He pauses, sleepy again, then,
–fuckin’ things off.”
Tony stares at the tights being stretched by Sid’s thighs, it’s weirdly erotic. His lips pursed together, he stays silent for a moment. Sid grows more restless,
“Tony…”
He breathlessly whines.
“Okay, Sid.”
He mocks. He can feel his heartbeat as he reaches for the top of the stockings, pulling them down slowly to reveal more of Sid’s skin. His thoughts won’t stop racing.
“Did they pick this outfit for you? Or did you?”
Sid cringes from the thought. He covers his eyes in the ditch of his arm and speaks,
“They just… put me in it, I had no choice.”
The stockings roll off Sid’s legs with ease the further down Tony pulls. The tightness is replaced by Tony’s hand barely caressing Sid’s leg. His body jerks from the sudden touch of skin on his, a soft groan leaves his lips.
“Even the panties?”
Sid pulls his skirt down, trying to cover himself up. He drunkenly blurts out.
“It felt so weird putting them on, they’re ‘Chelle’s.”
“They even made you shave?”
Tony looks up to Sid, his chest rising and falling more heavily the closer Tony gets to Sid’s thigh– He doesn’t reply. Tony slips off the socks from Sid’s feet and touches his bare legs with his hand, rubbing back and forth slowly. He can almost feel the new hairs poking through his skin if he presses down hard enough.
Sid’s lips purse from the feeling, his eyes still covered. He laughs to himself,
“...Like a girl.”
He inches further up towards Sid’s legs. The excitement moves from Tony’s heart to his groin, his pants getting tighter. Sid tries to stop him but the dizziness persists, he can’t move without almost vomiting.
Tony’s hands grip tightly around Sid’s thighs, his arousal and bizarreness of it all almost gets the best of him. Sid tenses up and whimpers from Tony’s grasp, his arm uncovers his eyes as he looks down at Tony.
“Tone, What’reyu doing–”
Sid tries to cover himself and push Tony away, but he doesn’t budge. His head spins again from the weight and he falls back down onto the bed.
“How many guys came up to you tonight thinking you were an actual girl, Sid?”
Sid makes a sound, he doesn’t know. It didn’t matter because he got to drink for free. Tony squeezes Sid’s thighs playfully, they weren’t full enough to feel like a real girl's thighs, they were boney and skinny– he pressed hard on the skin until he felt bone.
The longer he stays here, the more he wants to see what hides under Sid’s clothes. Finally, he decides. Tony sneers at Sid, his lips touch his leg. He looks up for a reaction, Sid tosses his head around, barely coherent– he doesn’t even notice.
Tony, unhappy with the attention being taken away from him, presses his tongue onto Sid’s inner thigh, licking and sucking until it leaves a red mark.
“Tony?!”
Sid squirms, his skirt riding up his waist and his underwear peeking through.
“Nice underwear, Sid.”
Sid shuts his eyes from Tony’s words, he squirms more, the tension rising up to his crotch. Tony smiles to himself and looks up to see Sid’s half-hard dick in Michelle’s panties, pre-cum soaking the fabric. Tony scoffs– It sends him over the edge.
“You like this?”
His eyebrows furrow as he leaves harder bites and sloppier kisses closer and closer to Sid’s groin. He moans into Sid’s skin, losing himself in it. Sid’s breathing deepens and he grabs ahold of Tony’s soft hair. He looks up at Sid,
“It feels like I’m about to eat your pussy.”
He snickers, his lips wet and red. Sid blushes from his sudden explicit words and pushes his face into Tony’s sheets,
“Stop it… I’m not… a girl.”
Sid says in between breaths, his grip getting harder as Tony opens up his legs to expose his soaked panties.
“Then why’re you wet like one?”
Sid groans in embarrassment, he sits up– prying his back off Tony’s bed, he pushes Tony away from his intimates. They have a moment of heavy breathing as they both look at one another.
“Stop–”
Tony’s big hand slams Sid’s face into his bed sheets, his head hits the bed with a thump. He lifts Sid’s legs up to the ceiling and lets them rest on his shoulder and chest. His bare legs and panties exposed, he takes his hand off Sid’s face to tug down his pajama pants. His dick springs out of his boxers and thrusts into the tightest spot of Sid’s thighs. The wetness of Tony’s cock and the silkiness of Sid’s skin makes it easy to slide through his best friends legs,
“Fuck,”
Before he can interject, Sid’s face is pushed back into the sheets as Tony folds him together. The feeling of Tony’s slick between Sid’s thighs makes him paralyzed– all he can do is take it and listen.
Chills run through Sid’s body from the sudden adrenaline, being used as a toy for Tony’s enjoyment was always a given in their friendship but never like this. Tony stares down at the helpless Sid. He watches as he shifts uncomfortably from the negligence in his underwear. Tony fucks Sid’s thighs harder and harder,
“So wet…”
He pants– he grips Sid’s legs harder and firmer, the opening becoming tighter and tighter around his dick. Tony moans and Sid can’t even listen to it let alone watch it. Tony takes his hand and grabs Sid's face, forcing him to look at the scene in front of him.
Tony’s furrowed brows and his arms squeezing so hard his veins are showing, Sid just admires him for a moment. No wonder he’s so popular– he’s really hot.
Tony stares back at Sid, his breath hitching from the contact. They hold eye contact as Tony feels a bubbling in his stomach,
“Fuck, so tight.”
Tony slows down to feel himself, he shutters and looks down at Sid. His eyes are teary and hooded, his makeup smudged and messy.
“What a pretty girl you are, Sidney. You should wear girls' clothes everyday.”
Sid breaks eye contact, he shuts his eyes and bucks his hips into Tony’s crotch. He attempts to somewhat be touched, his dick growing more and more swollen. He grunts, frustrated, his hand grabs at his member. He touches the tip of his dick inside his underwear, reminding himself of what he’s got himself into. Sid swirls it around his tip, he can’t help but let out a moan from the feeling.
Tony watches him succumb to his position and that’s all it takes– his eyebrows furrow and his jaw slacks. White hot liquid spills onto Sid’s thighs and lower body, mixing in with some of Sid’s pre-cum. He shivers as he comes down from his high, shifting in and out of Sid’s thighs, wetter than ever.
Sid’s head pushes into the bed as he pumps harder, his hips thrust to a vertical rhythm. Tony puts his legs down, watching Sid lose himself to his pleasure. He smiles sadistically, his phone sits on his bedside table. He pulls it out and turns it towards Sid.
“Show me how a pretty girl comes.”
Sid shivers at his words, gentle but demanding, his eyes still shut– he feels his body clench. He mutters curses as his dick twitches and climaxes. He holds his breath, his stomach shaking and tense. He lets out deep breaths, his eyes stay shut– almost like he doesn’t want to realize what just happened.
“Wow, Sid.”
Tony laughs to himself, his phone still turned towards Sid.
“Get me a water, please– you bastard.”
Sid says in between breaths. He sits up and immediately sobers up– mortified. Tony stands there, recording him and everything that happened in the last minute. He snickers and stops filming, he puts his phone back on the table.
“What the fuck, Tone. Delete that now.”
“How will I convince you to dress up like a girl for me again then? You won’t do it unless I threaten to release that to our whole school.”
Sid’s face drops, reality crashing down onto him.
“I’ll dress like a girl whenever you want– just delete that, Tone!”
Tony leaves the room, Sid tries to get up, but stops from the disgusting feeling in his pants. He sits there, wallowing in his guilt. Tony comes back with water and a granola bar. He sits next to Sid.
“Here you are, pretty girl. Or should I say– my pretty girl.”