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The first time Steve ever put on a pair of panties, he’d been fifteen, crossfaded to fuck at a house party at the Wilson twins’, in a circle of other crossfaded teenagers, and staring down the barrel of a triple dog dare. Tommy had been smirking at him like he’d thought he’d balk when he’d said to go get a pair of Betty Wilson’s panties and see how they fit — but Betty had been across the circle from him biting her lip and staring at his legs, and Paulie was somewhere else in the house and what he didn’t know wouldn’t hurt him, right?
So he’d gone upstairs with Betty and she’d handed him a pair of sweet little cotton undies, butter yellow with tiny blue flowers and a bow at the center of the waistband. She’d told him she would turn around while he changed — not leave, just turn around, and he’d known, of course he’d known, that the other messed up kids would want proof and Betty’s word would be good, but it still sent a nameless heat zinging up his spine.
Steve had stripped his jeans off, his briefs, and then pulled the panties up. The fabric had been soft against him, but the elastic at the leg holes itched, too tight, and the waist band had cut into his stomach in a way that wasn’t flattering on anyone. Still, he hadn’t been able to stop staring down at himself, a fist holding his polo up so he could look at the panties, the hair at the crease of his thighs, his belly, stark against the yellow cotton. He’d watched his dick twitch and chub up. The panties had distended, a little gap appearing at the waist band from the hardened weight of him. His heartbeat had pounded in his ears.
“How do they feel?” Betty had asked.
“Tight.” His voice had sounded hoarse to his own ears.
“Can I see?” she had asked.
He’d turned, and she’d still had her back to him, so he’d reached out, turned her himself. Her eyes had gone directly to his crotch, hadn’t even made a brief pit stop at his face, and her mouth had dropped open into a little O, pink and slick looking. She’d bit her lip again and she’d said, “You look hot.”
“Yeah?”
“Yeah.” She’d finally looked up at him. Her pale eyes had gone dark, all blown open pupil, and she’d put her thumb on the button of her acid wash jeans; her other fingers lay, long and fine, over her fly. “Want to see how they look on me? How they fit?”
Steve had nodded, and Betty had flicked open her fly, put her hand down her jeans and cupped herself before shimmying them down her waist. Her panties were lilac, solid, with lace trim at the legs; there was a wet patch where she was soaking them, and Steve looked at himself now too, his own wet patch.
“We match,” he’d said, and that was pretty much the last thing anyone had said for a while. They’d made out, messy with weed and beer and desire, and she’d pushed him back on her frilly comforter so she could straddle his thighs and put her hand on him while they’d kissed. She’d jerked him off like that, just rubbed his leaking head really with an open palm where it jutted out of the panties, until he’d creamed. Then she’d climbed over him, backwards, so she could sit on his face and still see his softening dick in her panties while he’d eaten her out. He got hard again, from her pussy or from her watching him, he hadn’t been sure, and she’d leaned over him to suck him through her panties while he tongue fucked her until they both came.
Betty had slapped him on the thigh when they were done, said, “You should keep those, a little something to remember me by,” and he had, after they’d emerged from the upstairs to a bunch of passed out kids who wouldn’t remember Steve’s dare in the morning.
He had kept them — only they’d never been something to remember her by.
They’d been a memory of that night, sure, but mostly they’d been a memory of how he felt that night. What it was like to pull that sweet cotton over his legs, to have that fabric cover his dick and balls so tight and soft — to have it darken with arousal when he started to leak. How hot he’d felt, under her eyes; how hot he’d felt, when he’d gotten home, still wasted and still wearing them, and stripped down to them in his bedroom to stare at himself in the mirror: the fabric wet again, where he was straining, and a little spunk dried on the bow.
What if it was someone else’s, a little voice had wondered that night, and he’d jerked off so hard and so fast, his legs had nearly given out when he came. Then, he’d stripped them off and shoved them in the back of his underwear drawer, and tried to forget.
Only Steve couldn’t, was the thing.
It was a thought that festered, an ache that kept throbbing. He couldn’t get it out of his mind: how he’d felt wearing them, how he’d felt having someone look at him wearing them — he couldn’t tell which one made him hotter, which made him crave doing it again more, to get to the bottom of this awful desire of his. But who the fuck could he let see him like that? He was almost positive Betty didn’t remember herself, the one person that might have been safe, because she never really looked at him sideways.
And anyway: it did feel good to wear them just on his own, right? Because he did, in the darkness of his bedroom when his parents were gone, he’d dig them out from the way, way back of his underwear draw and he’d put them on and he would lay there, a hand over himself in the soft cotton, just rubbing himself with the heel of his hand and luxuriating in the feeling. He told himself that was what made him hot: just wearing them. He told himself: he didn’t need to be seen wearing them, this was enough.
He could still go out with girls too, take them on dates and get them off, and he can get off with them too. It wasn’t like he needed the panties. He just liked it, right? It was just something fun for himself, something taboo and dirty and something no one would expect from Steve. It didn’t need to be a thing he did with a partner.
Even if imagining someone looking at him as he touched himself through the cotton made his toes curl. Even if imagining broad hands scraping up his thighs and toying with the leg holes as he pinched the head of his dick and made himself leak made him even wetter. Even if imagining someone telling him he was such a bad girl, getting his panties all dirty made him come harder than he ever had in his life.
That didn’t mean anything. It didn’t.
And it didn’t mean anything either when he picked up his first girly mag at that gas station outside Indy, saying it was for his girlfriend. It didn’t mean anything to bring that home and look at it, and the oiled, pretty men inside, and feel the burning urge to get his gifted panties out from their secret place, to put them on, and then roll over onto his belly to hump his pillow until he came, eyes locked on the thick, tattooed arms of the September centerfold.
It didn’t mean anything, because he would never do that, no in real life. It was just a fantasy, right? He still liked girls, still got them off and got off in turn to the taste and feel of their pussies — so what if he also got off on the thought of a guy between his legs sometimes? It wasn't like he was asking those girls to pretend with him, right? It wasn’t like he needed to picture some guy’s dick rubbing between his ass cheeks to blow in a girl.
It was okay if he was alone. It was okay if he just imagined sometimes. It was okay if he kept his fantasies to men in magazines, to Harrison Ford and Sean Connery and George Michael — guys he’d never see in real life. Like, wouldn’t it be so much easier that way, and less likely to end up with an ill-timed boner when Chief Hopper came to break up a party? (To say nothing of the sheer embarrassment that would probably actually kill him if he’d let some of his musings there grow legs once the Upside Down shit popped off.)
He was straight; it was just something hot and weird and he didn’t need to act on it. It would be fine, this way. No one would ever have to know.
But like being unable to keep it to just a simple memory, the desire found its way out eventually. It probably was always going to, would have grown too big within his chest to be contained to just himself. Almost immediately, in fact, did it start to expand and evolve.
It was always in the privacy of his home, of course. He could very easily get his rocks off like that, and then still take a girl out to dinner and go down on her in the beamer after. But the single girly mag became a couple, and his one pair of panties started becoming a collection when he realized he could just order from the Sears catalog with his mom’s name on the mailing address.
Did it make him feel gross putting her name there? A little bit, sure, but not for long — especially after he realized he could get other things besides just panties. He could buy panties, and bras, and dresses and skirts that swirled around his ankles and pooled at his waist when he was flat on his back, legs bent and open so he could watch himself in the door mirror take the tip of a finger through his panties. Which —
Okay, fine. Sure! Maybe it was more than just a harmless fantasy when he was alone! Maybe it was something bigger than that!
It was still — it wasn’t something he needed to get off, like he said, it wasn’t! It would just, like, creep into other things. Never a lot, never enough to be a problem, to be something someone would raise their eyebrows at. But enough that he started seeking out a certain type of girl: girls that would take control, would take the lead, put him on his back and take care of him while they took their pleasure.
Because it wasn’t like he wanted to have his control completely wrested away, or anything. He just liked — he liked being pretty for them, liked it when they treated him like he was the one who had never done anything before and they were the ones who were gonna show him a good time. There wasn’t anything wrong with that!
And sure he wanted to talk about it, to dissect it, but who the fuck would he do that with? Tommy? Nancy, maybe, once, when Steve had let her take the reigns and she’d decided she liked it. But that chapter was closed, and he thought he might break out into fucking hives if tried to bring it up with her and found out Jonathan was into similar shit. No thanks.
But then there was Robin. Robin, who was mean and funny and special, who showed him the soft, secret parts of herself with some fear and hesitation but no shame. Robin, who loved him against all odds and got him like no one else. Robin, who never judged him except for the candy he ordered at the movies and the way it took him a full ninety minutes to get ready every day when she preferred to roll out of bed. Robin, who never once hesitated to share whatever depraved little sexual fantasy she’d had with him but still screamed and tried to hit him when he said bobbies. Robin, who got out of Hawkins with him, who survived, who let him follow her to San Francisco and college and make a life with her.
(They’d all gotten out, nearly every last one of them, and they’d somehow all managed to land in California. Scattered between the Bay and LA and NorCal where Hopper was getting really into owning a vineyard, all of them happy to leave the demons behind for sand and smoggy skies and fancy colleges when the kids come of age. Steve couldn’t think of a better ending for their story, all of them safe and mostly whole, though he did always pour one out for Murray and Mr Wheeler on the big anniversaries.)
She had become so entwined with his soul, with all those soft, vulnerable parts of himself, he almost made believe that she knew already, by the time he told her. After all, they’d spent nearly every waking hour together they could, back in Hawkins before shit went tits up; and after, during the Almost Apocalypse, they’d lived out of each other’s pockets in a way that the government shrinks once said was “troublingly codependent.”
Steve didn’t give a fuck what they thought; didn’t really give a fuck what anyone thought, and if either of them got girlfriends or boyfriends or whatever that had a problem with it, they’d dump their asses. Anyway, Eddie lived with them and didn’t have a problem with it, thought that might have been because they’d given him the in-law suite in the basement of the town home Steve’s parents had co-signed the loan on (“Guilt’s a hell of a drug,” he’d said sagely) and he never really had to bear the brunt of their more allegedly codependent shenanigans. Plus, he was almost always off being a roadie for some band or another, so.
It had ended up coming up almost naturally one night. They’d been talking about going to a drag show with some of the girls from Robin’s lesbian roller derby club, and Steve had commented that he’d always been kind of curious about drag, thought he’d probably look pretty killer as a queen, but he was worried, what with his proclivities, he might, like, get a semi or something.
“I don’t think it’s actually physically possible to pop a boner with, like, the tucking,” Robin had said philosophically, then, “Wait, what?”
“What?”
“Why would you pop a boner in panties?”
“Histocially,” Steve had said, “it’s something I do.”
She’d blinked, and then blinked again. “Explain.”
So he had, and Robin, to her credit, only gagged when he said the word panties, which she said was less about Steve wearing them and more that she hated the word. She’d said, “I bet you look good.”
“I do, thanks,” he’d said. “You don’t think it’s weird?”
“Oh, definitely,” she’d said, “but all sex stuff is kind of inherently weird when you think about it. Sex is weird! It’s fun and funny and it’s weird! And like some of the stuff we’ve seen at clubs — yeah, you putting on panties and fantasizing about men is pretty low on the list. I mean, you also still sleep with girls, so maybe you’re bi?”
“I sleep with guys too,” he’d told her.
This, more than anything, had seemed to throw her for the biggest loop. “Wait, when?”
“Uh, pretty much since we moved here?” he’d said. “I mean, I figured, we’re here, it’s queer, if there’s anywhere for me to, like, self-actualize and shit and figure out if I liked it in, like, practice as well as theory, you know?”
“Look at you, like a little gay explorer,” she’d said. “I’m proud of you! I mean Eddie is totally gonna kill himself when he finds out, but I’m proud of you.”
Steve hadn’t been entirely sure what Eddie had to do with anything because, sure, he was hot as fuck and Steve totally would — but even though the guy seemed like he was flagging he usually had some goth chick on his arm when he was around, so it was probably just a fashion statement. Steve had been about to ask but then Robin had started talking again about how, yeah, it was totally normal but definitely a kink thing of some kind, and it would be pretty hot, you know, if she was a guy, or if Steve was a girl she was into.
“Well, as long as it would be hot to people who aren’t just me,” he’d said.
“It is,” she’d said seriously, and then offered to talk to the girls in the roller derby dykes to see if anyone had any zines that would be illuminating.
That should be that, he thought.
Robin knew, and was supportive, and they were going to figure out if there was, like, a name for his stuff and a community for him to try to get involved in, like she has her roller derby and her book club and shit. There was no one else that needed to know, right, that wasn’t a partner for sexy times.
And even that was weird to bring up on a first date, even a second or third, and he figured he should just wait, right, until the council of Robin’s lesbians came back with their findings. After all, he’d spent enough time doing it on his own time; it wasn’t suddenly harder to get off with other people now that one person knew. Sure, his hook-ups weren’t totally fulfilling but, again, they never quite were, that thing in Steve yearning and craving for his secret desires.
But he was good, as long as he fed it when he could, right? And he did.
Because once a week, he had the house entirely to himself from nine am to eight at night while he had his usual day off at the library and Robin was in class all day (and Eddie was on tour). He didn’t need the run of it, of course, because Robin would actually kill him if she found out he was engaging in sex acts in the kitchen — but it was nice to know he could be, like, loud and shift if he needed to.
(That, actually, might have been the only other thing Robin judged him for, but, in his defense, he grew up alone in a big ass house — he never really had to learn to be quiet.)
So he took advantage of it, and put on some pretty clothes and imagined some guy railing him in them.
Since leaving Hawkins and coming to a big, accepting city like San Fran, he’d been able to amass a bigger collection of pretty things to wear. He’d kept his old faithfuls from the Sears catalog of course, and Betty’s panties which had definitely become worse for wear — but he’d added to it, found some pretty second hand Laura Ashley dresses he liked to put on and pretend he was a housewife getting fucked over the kitchen table by her husband after a long day at the plant, and a slinky gown that made him look like a high end escort, he thought. In general, though, he pretty much just bought bras and panties that made him look virginal and sweet and asking for it. Those were his favorite to wear, to play in.
When he was alone, lying in his bed, he could imagine anything, be anyone: he could be himself all dolled up; he could be the housewife; he could be the escort; he could be at a party, making out in a closet with the guy he’d been going steady with and he was letting him cop a feel and spray sticky cum all over his panties because he was just too turned on by Steve to even manage to get them off and fuck him proper. He could be back in Betty’s bedroom, her eyes on his hard cock in her panties, about to blow just from the look of her and the feel of them. He could be anyone, anything.
Maybe it wasn’t everything he needed but it was enough. For now, it was enough.
He was out hitting up what felt like every thrift store in the Castro with Robin one Saturday when he spotted the cheerleading outfit. It was by no means what he’d been looking for; mostly, he was along for the ride while she tried to find a pair of Docs, because she was too much of a pussy to break them in herself but she still wanted to be a cool baby butch. He was always down to shop and he probably should invest in some new to him slacks for work, since his favorite two pairs were really starting to show some wear in the ass and he wasn’t going to be able to camouflage that with big ass sweaters once spring hit.
But they didn’t have anything in his size at this shop, so he’d been browsing through the racks when his eyes caught on it. Robin had been saying something to him but it was like all sound cut out when he’d pushed the hangers back to reveal a green and gold cheerleading outfit. It was from USF, of course it was from USF, but tell that to the static in his brain that was trying to resolve itself into technicolor porn that he was much more interested in exploring behind his closed bedroom door than in the aisle of this second hand shop.
“You thinkin’ pervert thoughts?” asked Robin quietly, leering over his shoulder at him.
He elbowed her hard in the chest, while she cackled at him, spinning a way to rub her sternum and cursing his sharp elbows.
When she’d calmed down, she returned to him, both of them always reeling in and out of each other’s orbits. He was holding the uniform, eyeballing the size, and she said now, calmer and sincere, “I think it would fit you. It’d be a great Halloween costume next year; you might re-traumatize Eddie but mostly I think he’d think it was funny.”
He probably wouldn’t think it was funny, Steve thought, but also Steve was never wearing this out of the house anyway. They were in a safe neighborhood, sure, but they both knew they shouldn’t loudly advertise that Steve’s actually intended purpose with a green and gold cheerleading uniform was to immediately put it on and pretend like he was back in high school about to get fucked by some jock for the first time.
Which, like —
Of course that was what he wanted.
He wanted that so bad.
Steve said, “Cool, I’ll get it then,” and threw the flannels Robin found over his arm, the cheerleading uniform sandwiched between them. It was a bust on the Docs anyway, so he bought their shit and they headed out for the next thrift store while he pretended like the cheer uniform wasn’t burning a horny hole through the back of his mind.
Pretended, in fact, for the whole four days until Wednesday rolled around, and Steve was gloriously home alone. He tried not to seem antsy or anxious about it, but he was pretty sure Robin had known for a long time what he got up to when he had full run of their empty townhouse and she definitely knew he was getting up to something extra depraved that particular time.
Truly, thank God Eddie was off on that tour. Steve didn’t think he had another day in him to wait for complete solitude.
As it was, the front door had barely shut on Robin’s smirking face before Steve was tripping his way up the stairs to his bedroom. He stripped his shirt as he went, hopped out of his socks and sweats and briefs and made a beeline for the bottom drawer of his dresser, which house most of his pretty things (save for the few dresses that would be wrinkled messes if he didn’t hang them at the back of his closet). For this one, he decided to get out his favorite set, lacey little numbers, panties that cut up high on his hips and ass and went translucent when he was turned on and a bra that made him look like he had actual tits by the time he got his pecs poured into the little demi cups, all perky and full and shit. It was his favorite set to wear when he needed a little pick-me-up, would stare at himself in the mirror on the back of his bedroom door and just run his hands up and down the curves of himself until he couldn’t stand it.
He looked great in just the set; it looked even better under the cheerleading uniform. He hadn’t tried it on yet, too aware that he would be starting something he might not be able to stop if he did, and he was thrilled to see it fit him. The sweater top was maybe a little tight, his shoulders probably much broader than the average USF cheerleader, but the skirt fit him perfectly, the hem just below the swell of his ass.
Steve wanted to get started immediately, but he made himself wait, letting anticipation build as he went to his en suite. He had a little make-up in one of the drawers from when he would go out with Robin, and he normally didn’t put it on when he was playing by himself, but something about this felt like it called for it. He put on some cherry chapstick and a little lipgloss, because he liked how it made him look like he’d been sucking cock, and a little mascara too, because he really liked the way that would run down his face when he was gagging for it.
Back in his bedroom, he tried not to get distracted by his reflection too soon, and grabbed his lube and a dildo out of his bedside drawer before sitting down at the foot of his bed. Then, then he could look at the picture he made.
He looked fucking unreal he thought, fresh and pretty and hot: the best kind of temptation. He put his hands on his knees, pressed tight together, and ran them up his thighs, careful not to disturb the way the skirt lay. He ghosted over his hips and then up his sides, over his chest, down his own arms. He stared at himself with wide eyes and imagined someone next to him on the bed, a faceless amalgam of guys in centerfolds and ballers he’d seen on TV. Steve Kerr, maybe, or someone like that: clean cut and handsome and talented, because that was who the person in this cheerleading outfit on this bed would go steady with, he thought.
Steve turned on his radio low, like music coming from the floorboards of a party, and imagined the guy kissing up the side of his neck, one arm around his waist and the other hand high on his thigh, over the warm wool fabric of his skirt.
You looked so hot out there cheering for us, he said.
“I was cheering for you,” Steve told him. “I knew you could do it.”
Yeah, baby? Knew I could take home the championship?
“Of course,” he breathed. The hand on his thigh slid down, between, and gripped him tight. “You’re the best player on the team. You’re gonna go pro after school, I know it.”
I’ll take you with me, he said. You’ll be so hot as a Laker girl. Everyone in America will want you, but only I get you, right?
“Right, baby. I’m only for you.” The hand on his thigh played with the hem of his skirt and he said, “You could, you could touch it, if you want.”
I could?
“Yeah. Want you too. Touch me.”
There, baby? Normally I only get to suck this pretty titties before you suck me off.
A pinch to his nipple and a little bitten back moan. He said, “You don’t make a, a championship winning three pointer every day. I want you to touch it.”
The hand on his thigh disappeared beneath his skirt and cupped him over his panties. His baller boyfriend groaned in his ear, said, You’re so wet for me, baby, soaking through these panties, and fingers trailed through the mess he was making, rubbing up and down and up and down.
Steve forced his hips to stay still, to not press into the feeling, as his boyfriend asked, Does it feel good? Does your pussy feel good?
“I, I don’t know,” he told him. “I've never —”
Not even a finger?
“No,” he whispered. “Ive been saving myself.”
It feels really good, you know, he said. I can just put a finger in, just one. Can I? Please?
“Just one.”
But then one became two became three and fuck he was so wet with it, his cunt was so wet, pussy throbbing as the fingers pressed in and out of him, and he’d be on his knees, probably, the boyfriend, but he wouldn’t try to eat him out. Half the guys Steve used to roll with never bothered to eat a girl out, so he figured this one probably wouldn’t either, even in Steve’s imagination, but he’d looked, and maybe he’d touched himself through his track pants while he waited for Steve to get wet and loose enough, and —
Steve scooted up the bed, lay back and put his knees up. His cheer skirt fell around his waist, exposing his panties, pulled to the side to expose his hole and messy with lube and precum. He said, “Maybe, maybe, if you’re gentle, you could put it in? Just, just a little.”
Groaning, his boyfriend said, You sure? I’m big.
“I know,” he said, and grabbed his dildo, pressing the thick head of it to his lube-slick asshole. He teases himself with the head of it, turning his own head to the side so he can watch it pop in and out in the mirror. It looked obscene, the thick, veiny plastic pressing against his hole while his cock twitched beneath translucent, butter yellow fabric. He’d discovered pretty quickly he liked to bottom when he was with guys, and the bigger and harder the better; Robin high-fived him when she saw this particular dildo for the first time and called him a slutty little size queen.
“You gotta be gentle with me, baby,” he whined, as he bore down against the thick cock. “I”m a good girl, never even, never even put a pinky in there. Oh, it hurts, baby, it hurts —”
But it feels good too, right? My cock in your tight little pussy.
“It does, oh, oh, it does —”
Say it, baby, wanna hear you say it —
“It feels good —”
What does, baby? C’mon, use your words —
“Your cock,” he moaned, loud enough that he thought the people in the party downstairs could hear him over the music. “Your cock feels so good in my pussy. My tight little pussy. Feels so good getting my pussy fucked, baby, my tiny, tight, pretty little pussy around your big, fat cock —”
Of course, this was when Steve’s door opened and Eddie wandered in. Or, more accurately, about halfway through Steve’s moaning, his eyes closed in bliss as he took the dildo in halfway now, Eddie walked in saying, “Hey, man, I didn’t realize anyone was home, but I heard your music, and you would not believe the week I just had —”
He cut off, then, and seemed to realize what he’d walked in on. Namely, Steve, flat on his back, his uniform top pulled up to expose his butter yellow lacy bra, his hairy tits spilling out as he pinched a nipple, and his cheer skirt pooled around his waists with his panties yanked to the side so he can ride his admittedly alarmingly large dildo. Steve wanted, almost immediately, to die with a quickness, but he had a dildo in his ass and a moan stuck in his throat and Eddie was just — he was just —
Well.
Huh.
He was staring at him. Or, more accurately, he was staring at Steve’s lubed up asshole around the dildo, then his panties, then his bra, then his face where Steve wasn’t sure the mascara had started to run yet but his lips were probably bright red from biting them, and then he looked back at his hole and oh. Huh.
Eddie was rock fucking hard in his jeans. At least, he was pretty sure that was the case. His jeans were super tight and Eddie always looked pretty big on a normal day because yeah, fucking sue him, Steve’s got eyes and Eddie was hot. He was pretty much the epitome of his fucking type these days — jock fantasies notwithstanding — but never thought Eddie would be into him, on account of how he was pretty sure he was straight or at the very least just not into preps.
But Eddie was hard, probably, and his face was bright red, and he couldn’t stop looking at Steve splayed out like this on his bed.
“You’re supposed to be on tour,” said Steve eventually, voice small.
It might have been his imagination but it looked like there was a wet spot appearing on his jeans. Eddie said, “Singer was a genuine fucking crazy person, got in a fistfight with the bassist and then arrested. Tour got canceled. You, uh. You.”
“Yeah?”
“You look pretty,” Eddie blurted. Somehow, his face got redder, which Steve didn’t think was possible. “Fuck, fuck, I’m sorry, I’ll just —”
“I do?” he asked.
“What?”
“Look pretty.”
“Yeah, you’re fucking — unreal.”
“Yeah?” he said again, and then, “You know, I’ve never taken a real one,” which was a bald-faced lie, but it definitely seemed to short circuit something in Eddie — something similar to what normally short-circuited in Steve when he pretended like this or encountered a virgin in the wild.
“You don’t say,” Eddie basically shouted, and Steve was so, so helplessly fucking charmed.
“My mom says I should save myself for marriage,” he told him. He slid the dildo out of his hole and put it next to him on the bed, but made no move to close his legs or to fix his panties, laid his hands palm down at his sides. His hole was just out, a little gaping, wet. Eddie swallowed hard and Steve said, “But I’ve always had a crush on you, you know?”
With wide eyes, he looked up at Steve. “Wait, really? Like, for real, or —”
“Yeah, man, for real,” said Steve with a snort. “But I’m, like, trying to do a thing here, and I thought you were into it, and —”
Dropping to his knees, Eddie said, “No, I’m into, I’m so into it. I’ve just, I have a crush on you too. Continue. I’ve got a crush on you too.”
“Yeah?” he asked, breathily getting back into character despite his heart pounding in his chest and butterflies in his stomach. “I’ve always thought you were really, really cute, but I never thought you’d like a prep like me.”
“I think you’re beautiful,” he said with startling sincerity. “The most beautiful, um, girl I’ve ever seen. I’ve, um, I’ve never gone all the way, either, you know.”
“You haven’t?”
“No,” he said. “But I know how to use my mouth. On girls, and guys. I’m good at it. And I, I really like it. Can I use my mouth on you, pretty thing?”
Steve groaned, chest heaving, and between his legs Eddie smirked at him, said, “I promise I’ll make it really good for you,” and then dove in to stick his tongue up his ass.
No one had done this to Steve, yet, but he himself had eaten enough pussy and ass that he could immediately tell that Eddie was a certified pro. It made him feel hot with jealousy, that someone got this with Eddie before him — that probably a lot of someone’s had — but he figured if he played his cards right, maybe he’d be the last. Which was probably an insane thing to think for a guy in a cheerleader’s uniform pretending to have his virgin pussy tonguefucked for the first time, but Steve had pretty much given up on being normal a long time ago. That shit was overrated, anyway.
He was messy with it, Eddie, sloppy and desperate and hungry, groaning and moaning as he tried to suffocate himself between Steve’s cheeks. He could feel his spit sliding down his thighs, spit and lube, which Steve knew tasted awful but Eddie was lapping it up like it was his last meal. He gripped his cheeks with his big hands — god, how had he never noticed how big Eddie’s hands were before, Christ — and his thumbs tucked in to try to spread Steve’s hole wider, like Eddie was genuinely trying to consume him from the inside out.
“Oh, oh,” he said, trying to grind down onto Eddie’s face but the grip he had on him made it impossible. He reached for his head then, tried to pull him even closer, while Eddie just groaned and practically unhinged his jaw to lick him out more thoroughly. He held tightly to his hair as he whined, “It feels so good, it’s so good, Eddie.”
Pulling back with a lick from his hole to his balls, trapped in lace, Eddie leered up at him and said, “Yeah? You know, they say it doesn’t count, you know, this way, so we don’t have to worry about your daddy coming at me with a shotgun for taking his baby’s virginity.”
“No, no, it doesn’t,” agreed Steve as he dove back in to stick his tongue as far as it could go into his hole. “It doesn’t count this way, I’m still — I’m still saving it for marriage. Mouth stuff, hnn, mouth stuff totally doesn’t count. I’m still a virgin, I’m still —”
Eddie groaned and yanked at Steve’s legs until his ass was hanging off the bed. He spit into his hole and then licked it out again while Steve fisted his hair and desperately tried to hump his hole against Eddie’s mouth. His tongue felt deeper in him this way but not deep enough, so he begged, “Fingers too, please, fingers too, Ed, baby, I wanna know —”
"Know what,” he mumbled into his most intimate skin between licks and nips and sloppy french kisses to his quivering hole. “You wanna know what it’s like to really have this pussy played with? Wanna know what it’s like to have someone reach deep in you and touch your spot? You want me to fuck this pussy with my tongue and my fingers? I don’t think it counts that way either.”
“No, no, please, please, fuck my pussy with your fingers,” he moaned. “Doesn’t count. Doesn't count if it’s just your fingers. Oh, please, fuck my pussy, Eddie, please.”
“Of course, baby,” he said. “Beg so pretty for me. Gotta touch yourself, though. Show me how much you like it.”
“Touch myself?” he asked, feigning nativity.
“Yeah, touch yourself. That sweet little clit there getting your panties all messy. Play with it. Get yourself hot while I finger you.”
“Okay,” he said, and reached down to pinch the wet head of his dick. Eddie bit his lip, watching.
“Look at you. Dirty girl, playing with herself.”
“You asked —”
“So it’s just for me, then? Pretty thing, playing with her fat clit while she begs for my fingers. God, I’m the luckiest boy, huh? To see you like this, to get my fingers wet like this. What would your parents think, to see slumming it with me and begging for my fingers in this tight virgin puss while you played with yourself like a dirty girl?”
“Eddie,” he warbled.
He said, “Here you go, baby, here you go,” and stuck two fingers in him. He was so wet with lube and spit, stretched from his own fingers and Eddie’s tongue, they slid it with no resistance, and Steve felt his back bow on the bed as they pressed hard against his prostate. Stars burst behind his eyes and Eddie relentlessly pounded into him, saying, “Good, huh? That’s your g-spot, baby, get you nice and hot and soaking for me. Wish I could feel this wet pussy on my cock but I know you’re a good girl, right, baby? So good. You’ll take my fingers and my tongue and my spit but not my dick and cum, huh?”
Thrashing his head, Steve said, “No, no, I’m, I’m a good girl, and it’s, fuck, you can finger me and spit on my pussy but not your, not your thing, I can’t —”
“My cock, baby,” he said. “I heard you say it earlier. Heard you imagine some boy sticking his dick in you, but you won’t let me even put the tip in? Probably ‘cause I’m not one of the good boys from your mommy’s church, huh, You’d let them put the tip it. Probably ‘cause they’d done it before, too —”
“No,” he said again. Fuck, it was too good. This was too good: Eddie’s fingers, his words, his everything, just Eddie, he was gonna explode. “I’d, I wouldn’t let them. But you, I’d — you can put it in my ass? I, I, I heard some girls talking if you, shit, if you fuck me from behind it doesn’t count either. I want you too. I want your dick in, in me. Like that.”
“Yeah?” Eddie pistoned his fingers in and out, furious against Steve’s prostate. He leaned in and licked sloppily between them, swirling and fluttering his tongue against Steve’s walls. He was going to come, shit, fuck! He was gonna come like this. Eddie pulled back, said, “Oh, baby, fuck if you let me, I’ll make it so fucking good for you,” and then he spit into Steve’s hole again.
Steve came so hard his left leg cramped where it had gotten draped over Eddie’s shoulder, and he shouted loud enough that he thought the neighbors would hear.
When he came back down to earth, Eddie was still between his thighs and still had his fingers in his hole, though they were still, and he seemed more interested in suckling at Steve’s spent cock through his ruined panties. He reached down and petted his hair and said, “Take them off so you can get a better taste.”
Eddie stared up at him with those wide, luminous eyes of his. “Yeah? Gonna let me get a good look at this fat clit finally, suck on her all sweet?”
Steve bit his lip. “I mean, if you don’t think I’ll be too sensitive after you made me cum so hard. Or if you just wanna fuck me, I know most guys don’t like —”
“Baby, I could spend the next twenty-four hours with my mouth on your sweet hole and never get enough, I would love to gag myself on this pretty little clit,” he said, and proceeded to gently put Steve’s sensitive, soft cock into his mouth. He just held it there, warming it, as he stared up at Steve and Steve stared at him. He reached down, took one of Eddie’s hands in his, and lifted it up to his own mouth, and sucked on his fingers like he was sucking on him. Eddie’s eyes rolled back in his head.
He worked him back up to a full hardness like that, cradled in his mouth and his fingers gentle but intent in his ass, before finally popping off and saying, “Now, I know I’ve, you know, never, and me putting it up your ass might be scary, but I promise I’ll make it good for you. Do you trust me?”
Steve nodded; Eddie’s fingers were still in his mouth.
But, reluctantly, he parted ways with them so that Eddie could get him on his hands and knees, facing the mirror with his head pillowed in his arms so he could watch. He gently pulled Steve’s panties down his legs but left him in his cheer skirt, groaning when he flipped it back so he could look at Steve’s ass. Steve watched him through half lidded eyes as he palmed his cheeks and then gently slapped each one until they pinked up under his touch. Then, he sat back on his heels and started unbuckling his belt, unbuttoning his fly.
It wasn’t a trick of tight jeans, Steve was gratified to see — he was hung. He felt his mouth start to water at the sight of it as it jutted out from a thatch of dark pubic hair and what appeared to be an elaborate tattoo. He was pierced, just below the head, and Steve wanted to grip it with one hand and impale himself back on it before Eddie knew what was happening. But that wasn’t the character he was playing right now, and the idea of it got him hot but not as hot as pretending to bite his lip and shyly say, “Oh, you’re so big.”
Eddie preened as he pushed his jeans to his knees. He said, “I know it looks like a lot but I know you can take it.”
“You sure?” he asked. “It’s — it’s got a little thing.”
“It’s to make your pussy feel good,” he told him. “That’s, you know, that’s what I’ve heard. Hit that sweet g-spot of yours. But I promise it’ll feel good up the ass too, baby. Would I lie to you?”
“No,” he said. “You’ll take care of me.”
“I will, baby,” he said, and then he leaned over Steve’s back, pressed a sweet kiss behind his ear, and started to drag his cock through the slick mess between his cheeks. He fucked him like that for a bit before and pushed Steve’s thighs together to fuck those, murmmurring, “You got a tight ass, baby, but I don’t know if I’m gonna be able to come like this. ‘Cause you’re all nice and hot and wet but this pussy, damn.”
He was holding Steve by the thighs, keeping them together tight to fuck them, but he raised one to palm Steve’s ass again and trail a thumb through his crack. He pressed on his hole, slipped his the digit in just to the first knuckle, and said, “Feel the difference, baby? Feel how hot your pussy is, how it wants something in it? I mean, it’s so wet and sloppy from my kisses I really think I could put the tip in and the tip, the tip, it doesn’t —”
“Doesn’t count,” finished Steve, cheek pressed into the sheet. His reflection in the mirror was obscene: sweat streaked hair, mascara starting to run from pleasure, the skirt flipped over his back and his ass hairy and tan as it stuck proudly in the air while Eddie moved like a god between his thighs. He wanted to see that pierced dick. He wanted to feel it in his guts. He wanted Eddie to fuck him until he cried. He said, “You can, you can put the tip in. But you can’t, you can’t tell, okay?”
“I never kiss and tell, baby,” he said, and quickly got Steve onto his back again. “Can I take your top off, baby? Wanna see this hot body better. Gonna keep that bra on though because those tits just look so sweet in there.”
“Yours too,” said Steve. “Can I see you too?”
“Of course, sweetheart.”
They pulled away from each other to carefully strip their clothes off, until Steve was only in his bra and Eddie was in his tube socks. His dick looked even bigger now that he was naked, proud and red and dripping from the slit. He was almost hairless except his bush and his pits and thighs, but he was covered in tattoos that flexed and moved as Eddie twisted his hair back into a bun. He was lithe and muscled and pale and Steve was almost delirious with the pleasure of seeing him like this, having him like this. It didn’t feel like a game, in these little moments between dialogue, and Steve tentatively allowed himself to want for more.
“I’ve got a crush on you,” he’d said. “I think you’re beautiful,” he’d said. “Wait, for real?” he’d said.
Steve laid down and spread his legs, saying, “Only, only the tip, right?”
“Only the tip,” he agreed, kneeling between his thighs.
“Will you, um, will you suck on my titties?” Steve asked. “To, to distract me, when you put it in? I heard it feels really good, and I think I’ll need the distraction.”
“Oh, I will suck on these sweet titties until they’re raw, baby,” he said. “Look so pretty in that sexy little bra, beneath all those little blouses of yours. Sometimes I can see your nipples, all perky and pointy and I cream myself to the thought of touching them, I swear.”
“Yeah?”
“Yeah,” he said. “You make me so hot, baby. I’m so lucky you’re letting me touch you. I’d kill to fuck you for real but if this is all I can have I’m gonna treasure every moment.”
“Eddie,” he said quietly, and the other boy bent his head and started to suckle on Steve’s right nipple where it peaked just above the lace of his bra.
It was part of the game, sure, but the feeling of his wet hot mouth on him did distract him from the fact that Eddie was starting to line his fat cockhead up to his hole, and press in. Steve didn’t have to force the tears to spring to his eyes at the pressure, the feel: he was fucking big and he could feel that little piercing dragging against the delicate skin of his hole as Eddie shallowly, carefully popped the head of himself in and out.
“Oh,” he said, “oh. Oh.”
“God you feel so fucking good,” he mumbled around his tit. “So fucking tight, so wet. God, I’m gonna cum.”
“No,” he whined. “No, you, you can’t, you — it’s only supposed to be the tip.”
“It is, it is —”
“Feels like more,” he said. “Feels so big, too big. Gonna break my little pussy. It’s too much, it’s too much.”
“It’s just the tip, baby, I promise,” Eddie said. “It only hurts cause it’s the tip, if you let me get a little deeper —”
“I can’t, I can’t —”
“I won’t, Promise. I’m trying, just. Just feels so fucking good, you feel so good —”
Steve pressed his head back into the bed, hooked a thigh over Eddie’s ass to urge him deeper as he said, “It’s so big, you’re so big, you really think it would fit?”
Eddie pulled off his tit finally to look at him with big, watery eyes. “Your sweet little pussy is made for it, baby. Made for me. I could give you a little more, if you really want? Doesn’t, you know, doesn’t count unless I’m all the way in. You know, I heard —”
God, Steve was going to explode. He bit his lip and reached down to touch the hot, spread wide skin of his hole — regretfully bypassing his dick, which was leaking so profusely against his stomach it looked like someone had spilled a cup of water on him — and then wrapped his thumb and index finger around the base of Eddie’s cock. He said quietly, “So you can’t go in all the way.”
“Of course,” said Eddie, his eyes rolling back at the touch. “Of course, baby. I’ll go so slow, so gentle.”
Steve skated his other hand down now and touched this soaking wet head of his cock, said, “And I’ll play with my clit. To, to distract me too.”
Eddie made a sound like he’d been punched and said, “Yeah, touch yourself while I get it in you.”
So Steve did, pinching and petting himself while Eddie worked his dick in until Steve’s fingers kept him from getting that last inch in, all while he groaned and moaned about how good Steve’s pussy felt, and how it would feel even better if he got deeper, begging him to let him go a little deeper.
“Does it feel good?” he asked. He’d returned to sucking on Steve’s tits, determined to make sure neither felt left out. “Does my cock feel good? Tell me my cock feels good in this hot cunt.”
Steve dragged him close with his leg again. “Feels so dirty, Feels so good. Does it feel good for you too?”
“So good, baby,” he breathed. “Feel so lucky you’re letting me do this. Letting me put it in you just a little bit.”
“I’m glad it’s you even if, even if it’s not all the way, really. You know. I can, I think I can feel it, your piercing. Feels nice, in me. Like a kiss.”
“Yeah?” Eddie asked. “Like my cock is kissing your pussy walls?”
“Mhmm,” he said. “Want it on my spot. Want you to touch my g-spot with the head of your hot cock.”
“It would. Oh, it would feel so good. But I can’t, baby,” said Eddie, a genuinely contrite note to his voice. “I can only do that if you let go of me. If you let me get all the way inside you. Then my cock can get right up on your spot and make you feel so fucking good, make you cum on my cock as I fuck you nice and hard.”
“I,” he started. He twisted his hips, ground down on Eddie’s cock. He felt so big and hot and stiff, splitting him open. He wanted him harder, deeper. He wanted to finish the game so he could get Eddie on his back and ride him until his cum was dripping down his thighs. He said, “You can do it.”
“What, baby?”
Steve took his fingers off Eddie’s cock, and put it between his shoulder blades. He lifted his other hand from his own dick and put it there too, holding him, cradling him. He said, “I want you to fuck my pussy for real, please. I want to, I want to share this with you. Just you. I, I want you to take my virginity. Please.”
Eddie leaned back, just a little, to look him in the eye. “You sure, baby? That’s a really big step.”
“I want to do it with you,” he said. “Fuck me, Eddie. Make me yours.”
He kissed him. Later, Steve would never be sure who moved first; he didn’t think it mattered. Just that they were kissing as Eddie’s hips fucked hard into Steve, hard and fast and sweet. He could, in fact, feel that piercing on his prostate. He probably would have screamed, if it weren’t for Eddie’s lips on his, his tongue down his throat. As it was, he definitely scraped his back raw as he urged him harder and faster and it wasn’t strictly in character when he pulled back to hiss into his mouth, “I want your cum,” but it felt right, it was true, and he added, “They say it doesn’t take on your first time, anyway,” for, like, verisimilitude or whatever, which made Eddie’s eyes rolled back into his head and his hips stutter.
Hot cum filled Steve and Eddie kept fucking him through it, seemingly determined that he wouldn’t go soft if he just kept on dicking Steve down. He was, frankly, happy to let the man try, and gave himself over to the sweet sensations of his body, the pleasure bursting like stars behind his eyes with every drag against his prostate. Eddie dropped a hand to try to strip his dick in time with his hips but Steve batted him away and said dreamily, “No, like this. Vaginal orgasm, please.”
“Jesus fucking Christ,” spit Eddie, and put his head down and his back into it.
Eddie filled him with cum a second time before he got Steve to tip over the edge, wet and messy and, yes, screaming.
He was boneless, after, covered in sweat and cum and leaking the stuff too. Eddie was curled on his side, his head against Steve’s chest, idly kissing the lace of his bra while his other hand cupped Steve’s messy hole, trailed fingers through it and then stuffed the cum back inside. Steve luxuriated in the feeling for a long moment and then kissed the top of Eddie’s head.
“Was it good for you?” he asked.
“Was it good for me,” said Eddie. “Was it good for me? I almost broke my dick off inside you, and frankly I would have thanked you if I had! Was it good for me. That was the single hottest thing that ever happened to me, when can we do it again?”
Steve said, “Whenever you’re ready, big boy. You know a pussy is made to take a pounding.”
“You’re a sex pest,” he said blankly. “You’re an absolute sex pest.”
“Yeah, but you love it,” said Steve and Eddie surged up over him, kissed him hot and thorough and sweet, and said, “Yeah, I fucking do,” before rolling him over to eat the cum out of his ass.