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“Would you ever try pegging?”
When you’d first brought it up, he shrugged. You couldn’t even tell if he’d heard you properly, so you decided to drop the subject. It wasn’t urgent.
The second time you brought it up, he choked. Not because of what you said, but because a strong gust of wind blew smoke from a burning book directly into his face. He didn’t even acknowledge your statement until you’d returned home for the night, back to your apartment full of torn pages and obscure knowledge.
“I’ve never thought about it.” He said, retreating to the bathroom to try and rinse the ash from his hair. You tilted your head. It had been over an hour since your question, and you’d forgotten what you’d asked. He leans against the door frame, explaining.
“Pegging,” he states plainly. “I haven’t thought about it.” He finishes speaking and then he’s gone. You sigh as you hear the showerhead turn on. The dye around his roots was already faded and you knew this would just fuck it up more. He waves you off with a laugh when you try to warn him.
The third time, surprisingly, Gerry is the one to bring it up.
“I’ve tried things like that on myself. Never with a partner.” He almost seems to spit the words out, twirling a ring around the eye-emblazoned joint of his pointer finger. A small nervous tic he’s developed over the last few years. It’s like he’s embarrassed to admit it.
“Would you want to try it with a partner?” You ask softly. Gerry isn’t a prude, not by any means, but you don’t want to scare him off by reacting too enthusiastically. Not when you’re finally having this conversation.
He shrugs like he’s trying to take up as little space as possible, nervous in a way you don’t often see. Every time you try to make eye contact, he averts his gaze.
“I’m not doing this with an unwilling partner.” You say. You’ve lost the softer tone of voice. It was going to get you nowhere, and if you’re doing this, you’re doing it right. “It’s up to you. You can research on your own, if you want. Or I can walk you through it. Take your pick.”
You know that letting him find things out his own way is generally the best course of action. It’s how he thinks things through, decides his next move. Until then, you’ll drop the subject. He’s just fine with that, and you go about your afternoon as usual.
He comes to you again about two days later, with a black bag and a grin that you know means he’s done something. You’re sitting, reading one of his latest finds at the kitchen table, when he strolls in. He drops the bag down onto the table in front of you before leaving without a word. You don’t touch the bag until he’s fully shut the door to the bedroom, knowing that usually when he brings an unknown object home, it has the capacity to kill you. But, given how smug he seemed about this one, you tug the bag open quietly.
Inside is a decently sized black box, a note, and what is quite possibly the largest container of lube you have ever seen. The box is emblazoned only with gold lettering spelling out ‘Sinful Solutions’. It’s sleek, smooth under your fingers as you open it. The cardboard gives way to a velvety interior, weirdly lush for its contents. You’re greeted by the sight of black leather straps, silver buckles, and a clear dildo.
You raise your eyebrows ever so slightly at the sight. It’s become apparent that Gerry left this as a gift of sorts. And, well, it would be rude not to use it.
You fish around in the bag for the note you’d seen, you end up grabbing the receipt. You scan the items listed. Lube, douching kit, strap on with a price tag you’re choosing to ignore… everything you’ll need. You don’t see the douching kit in the bag, so you assume Gerry took it with him for his own use.
The note itself reads only ‘Go get ready’, no punctuation and no signature. You know it’s from Gerry, though it’s a bit unusual of a style for him to write in. Must be antsy.
You’re knocked out of your stupor by the sound of the bathtub turning off. Guess that Gerry meant for this to happen tonight. You want to get your part of the prep done before he gets out of the bathroom, so you bring the contents of the bag to your bedroom.
After dumping them on your bed, you strip down. You’ve done almost nothing today aside from showering this morning, so that wasn’t a worry for tonight. You grab the strap out of its box and try to maneuver it onto your body, twisting your foot at a weird angle to avoid getting tangled. After tightening the straps around your hips and thighs, you grab the dildo. You can see a distorted version of your fingers through the silicone and it almost makes you snicker. It attaches to the harness easily, sitting on your hips.
You move towards the mirror hanging over the back of the door and take a look at yourself. The harness is decently comfortable, but the dildo looks ridiculous jutting out from your body. You stifle a laugh and gather up the remains of the packaging to move them aside, then place the note in your nightstand. It was short, but getting rid of it felt wrong. Gerry had a tendency to make you oddly sentimental.
Leaving only the lube on the bed, you flop back and await your partner’s return. The linen closet was only accessible via the bathroom, so you’d have to wait for Gerry to finish in there to lay them out. Your preparations for this were underwhelming at best. You weren’t sure what else to do to make him more comfortable. There were plenty of pillows on the bed, your sheets were clean, and candles would be a fire hazard with the sheer amount of paper in the apartment, so you simply sit and wait.
It isn’t long before Gerry enters your shared space, a towel wrapped around his waist with another in his arms. He takes one look at the silicone between your legs and lets out a sound that’s almost a giggle. It’s the most comfortable you’ve seen him since you originally brought up the prospect of pegging and you feel a small weight lifted from your shoulders.
“You look insane.” He grins. He walks over to you and bats at the fake dick with amusement. It wobbles a bit, but stays in place.
You just roll your eyes good-naturedly and take the towels from him. He’s already sporting a semi, but you ignore that in favor of laying the towels out in what will likely be a futile attempt at keeping your sheets clean.
When you finish, Gerry situates himself over the towels, legs spread and facing you. He leans back casually, as though he wasn’t completely bare in front of you. You take a moment to absorb the sight before speaking.
“Flip over, it’ll make it easier.” You grab a pillow to place under his hips in order to keep them elevated. He moves to lie over it.
You move behind him to see his ass in the air and the smooth planes of his inner thighs spread around the pillow. The small amount of fat adorning them catches your eye and you can’t resist palming them to spread them wider.
His tip peeks out from beneath his abdomen, fully hard and leaking slightly onto the towel. You can see him shifting to try and create some type of friction, to no avail. You want to have mercy on him, get him off as many times as he can stand, but you maintain your self control. Tonight is different.
“You look so good like this.” The words slip out before you can stop them. They aren’t a lie, far from it, but the praise risks undermining whatever dominant persona you had planned for the night. Fuck it. You grip his ass and spread him apart. “So pretty for me.”
You get no response from him, but he pointedly avoids looking back at you, preferring to bury his face in the comforter. That’s fine. You’ll be hearing plenty from him soon enough.
You grab the bottle of lube from the edge of the bed and squirt some on your fingers, spreading it around and slicking them up as much as possible. Straddling the man’s legs, you squeeze a bit directly onto Gerry’s hole for good measure before gently prodding him with your middle finger. His back arches, pale, with a line of tattooed eyes down his spine. You run your hand up and down it as he sucks your finger in to the second knuckle. He’d loosened up a bit from the douching, but Gerry was so tense that it would take a decent amount of work to get him ready for your strap. He shivers as you finally insert your finger all the way and you rub soothing circles into his hip with your free hand.
You add a second finger slowly before hooking them down towards his bellybutton, hitting a small notch inside of him. Gerry keens below you and you have to take a moment to recover. You feel him throb around your fingers, and you make a mental note to aim for that spot again. He pushes his hips back into your fingers in a desperate attempt to grind against the pillow beneath him.
“Right there, fuck.” He groans. He spreads his legs further, giving you better access to where he wants you. You rub against it again, hearing him try to bite back moans as you do so. He’s so much more sensitive than he usually is, and you plan to take full advantage of that.
You scissor your fingers a bit, mainly focused on stretching him properly, when he pipes up.
“I think that was my prostate. Haven’t been able to hit that before .” He chokes out. You smile. He definitely did some research on his own. You’ve always loved that about him; His willingness to learn and try new things for you.
You’ve given him some reprieve from direct stimulation, but you can’t help but brush against it while adding the third finger. Gerry shudders beneath you and grips the sheets next to his head. His hips buck back into your hand, cock fully hard now, the head red and weeping. You run your thumb over the slit lightly before returning your attention to his ass.
Letting it drip off your tongue, you spit onto his hole. You thrust your fingers into him, watching as the substances mix to make a creamy ring around the base of your fingers, before taking your fingers out and licking it off his ass. You dip your tongue inside him for a second just to hear him whine softly. When you pull back, he turns to look at you.
“Why’d you stop?” He asks, his voice coming out weaker than usual. You smooth your hand over his back one last time before standing up.
“Because I need you to flip over. I wanna see your face when I fuck you.” You say. You could see a blush creeping onto his cheeks as he complied, turning onto his back and placing his hips over the pillow once more.
Your eyes drift down his body, the eye over his heart, his thin waist, the blonde happy trail leading to his hard cock. You lean down and take a moment to breathe him in as you lick and suck at his neck. Going painstakingly slow, you’re careful to leave marks where everyone can see them. To make sure they know he’s yours.
He pushes at your shoulder, trying to force you down, to touch him where he needs. You lick the shell of his ear before giving in.
“You’re so impatient. Let me play with my food.” You whisper. You pinch at his nipples, watching as he arches into your touch. He’s always been responsive when you play with his chest.
“I need you. Please.” He says. You’ve never heard him beg this easily, this readily. He must really want it.
You retreat back between his legs and squirt lube onto your strap. It’s been resting uselessly against Gerry’s own cock as you tease him, awaiting use. It’s nearly dripping by the time you feel that it’s slick enough, but you can never be too careful. The last thing you want is to harm your lover.
You grab the backs of Gerry’s knees and gently fold them upwards towards his chest. Looking down at him, you can’t help but think that he’s never looked more beautiful than he does now. Faded black hair fanned out around his flushed face like a halo, pale chest heaving as he waits for your next move. You feel your heart swell as he smiles up at you. The amount of trust he has in you, the love he holds for you, it’s all overwhelming. You can’t help but adore this man.
“You alright?” Gerry questions. Apparently you had paused a bit longer than intended.
“Yeah,” you respond, shaking your head slightly. “I just… I love you.”
He needs no pause before acting, looping his arms behind your neck and pulling you down. For the first time tonight, you kiss him properly, rubbing your thumb across his cheekbone. He leans into the gesture, lightly tugging at your hair. You don’t need any words; You can feel his love in every touch, every moment, every time he chooses to try something just for you.
Your breathing is heavy as you pull away, mere inches between your faces. It would be a crime to pull away further. He gazes up at you with adoration before slipping his hands down to your ass, groping and squeezing as he tries to calm himself.
“I need you to fuck me now,” he breaths. “Please. I’m begging you, please.” The sound of his pleading goes straight downwards. How could you deny such a polite request? You move his legs back up from where you’d let them drop down, pressing his knees as close to his shoulders as possible.
He gasps when you line the strap up with his hole. You know that you prepped him enough, but go slow nonetheless in order to make sure that he’s comfortable.
The only sounds in the room are your soft panting and Gerry’s moans. You look down to where the two of you connect and let out a groan at the sight of his hole stretching around your strap. The clear silicone lets you see everything, which, weirdly enough, makes it feel more intimate.
“You alright?” You ask. Gerry just nods, breathing heavily and trying to relax. After a while of slow movement, you’re able to bottom out. You can only imagine how he’s clenching around your strap.
“You can move now.” He breathes. “Just start slow.”
You heed his warning and start off with a shallow thrust, hearing him gasp as the head of the dildo hits his prostate. He grabs at your shoulders and drags you down to him, kissing you sloppily. You press his thighs further to his chest as you pick up speed.
His moans grow in volume, breath hot against your ear. You feel his cock throb as it rubs against your abdomen with every thrust. Precum smears against your stomach, but you ignore the stickiness in favor of reaching between your bodies and stroking him.
His breath hitches as you do and he lets out a choked whimper at the sensation. He can’t move his hips without overstimulating himself, moaning in your ear each time he does. He grabs your hair at the nape of your neck and tugs at it.
“I- I think I’m gonna cum.” He says, voice trembling with each thrust. His legs tighten around your hips forcing you to grind against that spot that makes him see stars. You suck at his jugular as he pants, before you feel his hot release in between your body and his.
His legs shake around you and his grip on your hair tightens as he cums. The sound he lets out borders on a scream, something you’ve never heard from him before. You keep thrusting slowly until you’re sure he’s come down from his high, then remove yourself from his hole entirely. The aftershocks have him tightening around nothing.
“That was,” He exhales. “That was incredible.” He shakes his head. You giggle a bit and run your hands along his thighs, slowly lowering them from their place against his shoulders. When he’s relaxed, you take your free hand to gather the cum on his abdomen onto your fingers. You bring them to your lips and suck.
Gerry watches, mesmerized, before taking your fingers into his own mouth. The salty taste of your skin and his cum mix on his tongue.
He drops his hand back down against the bed and sighs. The euphoria of his orgasm is fading and he’s beginning to feel his release drying against his stomach. He groans and you know exactly what he wants.
“I’ll grab a towel.” You quickly remove the strap and run to the bathroom, running a rag under the faucet. You return as fast as possible, wiping Gerry off and covering his face in kisses. He playfully pushes you away, rolling the both of you onto the bed. He grabs the dirty rag and throws it on the floor next to the bed.
“Ger, we gotta change the sheets.” You say quietly. He ignores you in favor of burying his face in your neck.
“We’re clean enough. Let’s do it tomorrow.” He whispers. You can never say no to him, especially not after he breathes a soft ‘I love you’ into your skin. The mess is tomorrow’s problem. All you need tonight is the feeling of him against you.