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‘I have to take a shower. You said you were tired, right? Why don’t you have a nap?’
Sure, it started out innocent enough. Come over to your girlfriend’s apartment for a date, but she’s not ready, and you stayed up until Stupid o’ clock in the morning drinking with your brothers, so you’re exhausted. She has a really nice bed, too, so you were excited about taking a nap on it for twenty to thirty minutes while she showered.
Except, uh.
There happened to be something on the bed. Really, at your age, you shouldn’t be getting this excited about seeing a bra on a girl’s bed. Especially if there’s no girl in it. But it’s so pretty… Pale pink with little white polka dots about halfway up the cups, then adorned with thick, ruched lace and a little bow in the middle. It’s attractive as a garment, fitting of your girlfriend and her style.
You don’t know what possesses you to put it on.
It’s amazing that you can even clasp it together at all, but maybe you aren’t as much wider than her as you thought. Although you spend about two minutes fighting with it with your arms bent behind your back before giving up, turning it around, clasping it, then rearranging it so it’s facing forward and you can get your arms through the straps. Your face is on fire as you kneel on the bed and look at yourself in the mirror adjacent to it, but you can’t deny that you like what you see. Your pecs actually fit almost as nicely in the cups as Todoko’s breasts do, though they’re the wrong shape and there’s a little bit of space between the lace and your body.
You also can’t deny that you’re already a little hard.
Twenty-five minutes. Twenty minutes? How long has it been since she got in the shower? You seem to recall her taking longer showers, so you might have time to take care of this problem before she comes back and finds you wearing her underthings. Eyes fixed on the mirror, you unbutton and unzip your pants, shoving them and your underwear down a little until your cock is exposed. You spit into your hand and stroke it a few times, coaxing it to life gently, but insistently. You don’t have unlimited time, after all.
But something about seeing yourself with your dick in your hand and your girlfriend’s bra on is…weirdly thrilling. Somehow a little forbidden, giving you a pang that makes you think maybe this is wrong. Well, maybe you should have asked her. Maybe you shouldn’t be jerking off without her. Maybe you should just wait and you can have sex together, as you’re meant to.
“Ahh…” The first moan breaks free from your lips and you can’t bring yourself to find this wrong any more. Your other hand crawls up your torso, nudging under the wire of the bra to pinch at your nipple. Dirty. You’re embarrassed, still, but you like it. You like the shame, and no one is watching, so it’ll just be you being guilty about getting alone when you’re supposed to be sleeping. Except you don’t feel tired anymore, just horny. You get a little reckless with your fingers, shoving at the bra until it slides up over your nipple, lewd and forbidden. Moaning again, you wet your fingertips with your mouth before pinching again, feeling the moisture slide over your skin as your hand slides around your cock.
You’re not really sure what’s going on in your head as you continue to play with yourself and jerk your dick. You’re not imagining Todoko wearing the bra, you don’t think. It’s just you. You like the look of your stomach tensing, your cock dripping in your hand, your more-muscle-than-fat pectorals messily concealed by what is meant to be women’s clothing. One of the straps slips off your shoulder, and you gasp when your cock twitches, eyes drinking in the picture of you looking disheveled, but also in control.
How long has it been? How much more time do you have? Maybe you need to step it up a little if you’re going to get off. You’ve never tried this, but since you’re already… You can’t think of a better word for it than ‘emasculating’ yourself, but even that doesn’t feel quite right. Essentially, you’re toeing a line, so maybe you could just get one foot all the way over it. Wasting no time on hesitation, you lean back and shove your pants all the way off. At the next step, you do hesitate, wondering which position would be best, but you quickly decide. You shove your fingers into your mouth, purposefully avoiding looking into the mirror because you know what you’re doing isn’t quite sexy, as you’re just trying to get them good and wet. But you’re less concerned about looking at yourself now and more just on feeling.
You collapse forward on one shoulder, pinning it between your body and the sheets to grip your cock as you spread your knees apart and reach over yourself to nudge a finger at your hole. The puckered muscle twitches at the contact, but you push through before you lose your nerve and open your mind. The sensation is…unusual. You thrust your finger in and wiggle it around, trying to get a better feel for it, thinking that the more you do, the more you’ll feel, and the faster you can get all your clothes on and pretend to be asleep.
You suppose it’s kind of hot to just think of the simple fact that you’re actually fingering yourself, but even that isn’t quite enough. You work a second one into you before it goes dry and stretch the two of them apart.
“Oh…” you murmur into the sheets. This is a little different, this stretch. Not quite pleasure yet, but you feel like you might be getting there. If only you could just—
The door opens, and the sound of humming fills your ears. Your fingers are quickly out of your body and away from your cock, and when you try to support yourself on the arm you’d had under you, you fall sideways down on the bed. It takes you a moment of frantic scrabbling to get up to a sitting position, but this doesn’t really change the fact that you’re wearing Todoko’s bra and jerking off and fingering yourself. Or you were. Now it’s down to one out of three, which is still pretty incriminating, and you’re burning up on the spot.
Todoko continues to hum and tugs the elastic out of her hair as she enters the room, her hair falling from the tight bun she wore to shower into loose waves around her shoulders. She pays you no mind, but goes over to her closet and starts moving hangers around, looking for an outfit, you would guess. You have nothing to do but sit and watch her with mortification creeping up your body, threatening to drown you. Is it possible she didn’t see you? You consider getting her attention if only to move out of this particular frame of suffering.
She picks out an outfit and hangs it on the door as you sit and watch, then unwraps the towel from her body, which does nothing for quieting your raging erection, and moves over to the nightstand. “Karamatsu?” she says finally.
“Y-Yes?” You clear your throat, but make no other movement, every muscle tense and anxious.
“Get on your hands and knees.” She’s still looking through the drawer, completely casual.
You stare at her for a moment, trying to puzzle through what’s happening, but find you’re still too mortified by how you’ve been discovered and the fact that she actually did see you to fight her. Not that you’d ever do that anyway, but you do feel like you should be having some sort of horrible confrontation that you are destined to lose, that you’ll never live down. But never mind that if you can avoid it, you suppose. You move over again, lifting your bare ass in the air and settling on your forearms. Your left shoulder hasn’t quite recovered all feeling yet, and you’re hoping this is an acceptable compromise.
She climbs onto the bed behind you, leaving you to feel very self-conscious until you feel two of her fingers pushing into your hole again. You half-groan, half-squeak with surprise, jerking your hips forward, but her hand is firm on you, pulling you back. “Shh. You weren’t doing that with any lube. That can’t be comfortable. Plus, I don’t think you can get very good angles like that.” She presses her fingers in and down and suddenly you’re choking on another, more violent moan as your cock jumps between your legs. “Good boy.” She pats your ass gently.
“Todoko?!” you gasp, trying to turn to look at her, but she pushes your head down and away from her. Her fingers of her other hand come up your side, playing with the band of the bra. She moves them around and pinches at your exposed nipple, rolling it tightly between her fingertips, and you moan again.
“You should have told me you were into this, Karamatsu,” she coos at you, pressing a third finger into your hole and stretching them all wide so you make another noise. “Good, good. See, it feels nice to be taken care of sometimes. Of course, I’ll make you return the favor.”
“I-I will, yes,” you gasp out, nodding and rocking back on her fingers, not even sure you know what you’re agreeing to. You’re distracted. Now that you’re feeling her experienced (and lubed-up) hand working you open, it feels a lot better than when you were just fumbling around. You wish she would touch your cock, but you’re sure that’s coming.
She curls her fingers again in you, bouncing her fingers against that one spot that feels ridiculously good and makes you sob out little noises of pleasure, and then her hands are pulling away from you.
“Todoko?” you call again, turning your head, but are pushed forward again.
“No peeking,” she chides you, practically singing it out. You hover, bent over like this, still wearing her bra and expecting her to flip you over soon. You even hear a condom wrapper, but she doesn’t call for you to change positions. You feel a hand on your hip again. “Relax, Karamatsu,” she tells you. Relax? Why—
“Oh!” you gasp when you feel something much bigger than her three slender fingers nudging into your hole. “Todoko, what—Ahh…”
“Oh, come on, Karamatsu. You know what a strap on is. Do you not want to?” she pauses with the head of the toy pressed into your ass, holding you wide but not pushing deep enough into you for you to get the full experience.
You hang your head between your shoulders and shake it. “No, keep going.” Truthfully, you’re on fire. Your girlfriend pushes the fake cock deeper into you until you feel her warm skin against your ass, and then she stays, letting you throb and acclimate to the thing. It’s really big and solid, and there’s a bit of pressure just on that spot she was poking at with her fingers. You let out soft little noises and shift around as she rubs soothing circles into your back.
“Relax,” she tells you again. Her hand stretches across your back, the warm skin comforting you, and the other sneaks between your legs and grips your cock, giving it a few strokes back to full hardness. “You okay?”
“Yeah… Yeah. G-Go, maybe,” you mumble out. She moves, shallowly at first, then a little deeper, rocking her hips forwards and back and hinging along the line of her cock as it slides in and out of you. It’s making your whole lower body tight and warm and sensitive. Her hand around your dick feels twice as tight as usual, maybe more. Your ass feels slick and full and the friction isn’t like anything you would have imagined, not to mention the whole thing where it’s your girlfriend fucking you. You never would have thought you would end up like this. You’ve never really considered yourself gay, but you’re not sure if it’s even gay if it’s a girl doing it.
“Feel nice?” she asks gently, though her rhythm in and out of you is a little more fervent. “You look good like this. Really cute.” She giggles, rubbing her thumb in soothing circles into the back of your hip while her hand does a good job on your dick.
“It feels—ah—really good, please… Don’t stop.” Your face is just as hot as ever having to tell her to keep fucking your ass, but you only barely care. You were getting off on your own private embarrassment earlier, and isn’t it only embarrassing if someone else can know about it and judge you? It doesn’t seem like she is, from how carefully she’s stroking you and how insistently she’s fucking you. Your cock is twitching and leaking desperately and every time she rocks back and slams into you your arms quake. You’re not going to hold out much longer.
“You close?” Todoko smooths her thumb over your slippery head and you just moan in response. Your moving back on her, embracing the rubbed raw and fucked out feeling you’re beginning to have. In another couple of thrusts, you’re gasping out her name as you come into her hand, possibly the strongest orgasm you’ve ever had in your life. The extra sensation of her fucking you while she pumps you through it makes you come twice as hard, and the spasms shake your body for a few long moments afterward.
You hardly realize Todoko was half-holding you up until she pulls out and you collapse on the bed. Your eyes close for a second, and you feel the bed shifting as she moves, but when you reopen them you get a brief glimpse of her setting what looks like a massive pink cock on the nightstand, attached to some kind of harness, and then she’s crawling back on the bed over to you.
She’s on her knees, smiling a little deviously down at you. You’re on your back now, looking up at her and feeling a twinge that’s not quite arousal just looking at her, and only because you’re body has had enough for the next hour, you’d guess. But she hasn’t. She gets a knee on either side of your head and fists her fingers in your hair. You catch a glimpse of the insides of her legs, which are already wet and shiny, and knowing that she enjoyed fucking you as much as you enjoyed being fucked by her gets you salivating a little.
You grip her soft, creamy thighs and pull her down to you, mouth open to lap up the wetness between her legs. She grinds down on your face as your tongue settles around her clit, rubbing over the swollen nub again and again, and she makes a soft little whimper. “Karamatsu…” she moans, rolling her hips down over you. You eagerly thrust your tongue between her lips deep up into her, probing around her slick walls, desperate to lick up the taste of her. Todoko gasps and her thighs tense around your cheeks, so you hug her ass to you with a firm grip as you move up and down across her.
You hum a little with your lips locked around her clit, gently running your teeth over it and sucking it so she grips your hair tightly. You can tell she’s close from how tense her body is above you, and you mercilessly lave your tongue over the same spot until she’s shaking. She moans wantonly and falls down onto her other hand, pressing her body against your hot, wet mouth as you suck on her, and wails when she comes. You don’t stop, wrapping your arms around her legs and squeezing her too you as you continue to hold the pressure, swiping over and over with your tongue. She’s still shaking from the first orgasm when the second hits her and she’s rocking against you on quivering legs.
You back off a little, looking up at Todoko to see if she wants more, but she’s holding herself away from you now and slowly slinging her leg back over you and sidling down next to you. She leans her head against your shoulder and curls an arm around your chest. You can feel her body thrumming with energy and you feel a little bit smug, though perhaps she has more of a reason to be so than you do, and you can still feel that too. She’s gazing vacantly across your chest where her bra still covers your pectorals, and you watch her hand creep up to land on top of one of the cups. Okay, a little weird, but maybe her arm is just more comfortable that way.
No, she’s squeezing it now.
“Todoko…” you begin, watching her thumb and palm curl over your not-quite-breast repetitively. She’s wearing a slightly loopy smirk.
“Shh, let me have this.” She keeps squeezing.