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That One Night

Jerry was lonely. This was nothing new, he'd been lonely for a while. Emotionally, romantically, physically... so lonely. He wasn't a weirdo, he had a quiet job and plenty of friends there, he was only about an hour away from his hometown, so plenty of old friends, family. But that's not what he was looking for.

Most nights he'd come home from work and scroll tinder. He'd make dinner, a left swipe, a right swipe, but nothing ever really came through. Some girl he wouldn't rate super high and they'd have a conversation that went nowhere and the night would be over, dishes done, maybe a show watched or a couple of pages of a book he'd probably never finish, that's it.

But he'd try. He'd give it some attention and try, really do what he could to make a connection he wasn't excited about with someone who didn't really move him. Sometimes he'd look at a profile and know that he'd like to have sex with the girl in the picture, but he was always pretty sure she wasn't thinking the same thing. He was uninspiring. 5'6", a little heavy, a haircut that never looked quite right, and at this point, at 39, usually a couple days ambivalent facial hair.

What was he looking for? Love? A few dates? A tired handjob at the end of a third boring date would be the best day of his year. He didn't know what he was looking for, only that he was looking. But however much he looked, he ended up empty.That One Night фото

This is how Jerry was living, four years since his last uninspired relationship. They'd gone out for about 6 months, bad sex twice on his couch, and she was done. She worked at Hobby Lobby over by the mall, and she started feeling guilty about him not being religious, but Jerry wasn't heart broken. It just didn't click. And every night since, it's the same. Home, tinder, dinner, wash up, clothes ready for tomorrow, and to bed.

But when he went to bed, Jerry came alive. He always slept without his pants, and liked to jerk off really slowly. Some days with lube, grabbing tightly at the base of his shaft and pulling his regular sized cock to the tip, pulling his head and arching his ass up, his eyes closed tight imagining those long powerful thrusts into some woman's tight little asshole while he guided himself with great handfulls of ass. He'd never been in a woman's ass before, but his imagination was SO GOOD. Or he'd grab himself raw and stroke furiously, imagining her lips around him, bumping his balls to her chin while the tip of his cock ran up against the back of her throat, imagining her hands on his ass, holding him as deeply as she could while he came, then she'd swallow and kiss him while she gently stroked until he was completely soft.

And Jerry would cum, lying there alone in his bed, and fall asleep while the little pools of cum dried on his belly or ran down onto his balls.

This was the very best part of his day.

But Jerry wanted his day to be better. Fucking a real woman would make it better, feeding her his cum, which she'd want like it was air to breathe. But he hadn't found her, so he'd have to find the next best thing.

A few times while he'd traveled for work, he'd gone to sex shops and gone into the booths at the back. He'd lock the door, ignore the world around him, and jack off to strange porn, leaving a puddle on the floor at the end. But tonight, he thought, he would try this closer to home. He knew there was a big sex shop off of the highway, and he started to get hard thinking of the videos he might see: severe European brunettes smoking cigarettes while hairy, thick cocked men fucked them with punishing thrusts, or young white girls in detention giving blowjobs to the black football team in the back of the room before the teacher steps in and really shows her how to fuck... he was really excited.

When Jerry arrived at the store, he nervously entered. It was already 9 and they'd close in about an hour, but he knew that he find some cure for his desperate loneliness. He walked toward the back of the store (it was huge and so much cleaner than the shops he'd been to before) looking for the booths, but... no booths. He'd been suspicious at how corporate it all seemed, and he'd been right.

But Jerry was too lonely to give up. I imagine a lot of us have been through this. He wandered the aisles, the DVD's with star stickers over cocks driving into hairy pussies, or the look of surprise on a girl's face as she sits on a toilet and looks up at an enormous, soft penis hanging thought the wall. It was a little hot, but Jerry needed more. A sex doll? Too expensive. Maybe some sort of toy?

Jerry found his way into the aisle with the toys. The store had not been crowded, but there was another guy in this aisle, kind of looking around, seemed disinterested. But Jerry was becomming too horny to care. He looked at the vaginas and imagined his cock sliding in and out, it was so hot. But the experience was hot for Jerry too, and he didn't want it to end. He looked at the other guy in the aisle as he picked up his pocket pussy, and watched him looking at butt plugs.

He felt bold suddenly. "Hey, how do you choose? I can't tell which one of these is better," Jerry said, gesturing to the different vaginas.

The man looked over at him, then at the vaginas. "I think you just have to try a couple and see which one suits you. I had the purple one over there, but it's probably as good as the one you've got."

"Oh! I assumed you were gay."

"No, it's weird, not attracted to guys, but I've had sex with two guys and it's been pretty hot."

"Huh. So is it different? Like is it different to have a man go down on you instead of a woman?"

"Why?"

"I was just..."

"Do you want me to suck your dick?"

Jerry thought. Fuck, he was lonely. If he could imagine it was a woman, he could close his eyes and not have to buy this, and a mouth is so warm..."No kissing or touching?" He said quietly, "Could I just close my eyes?"

This new man smiled. "Yeah, yeah you could. Right now? I live 5 minutes away."

He thought for one second. "Okay, let's see."

Jerry went out to his car, following about ten feet behind this new man into the parking lot. He drove behind him for a few minutes and parked.

"Come on upstairs." The new man let him up a flight of stairs and into a relatively clean apartment. Why don't you sit on the couch and take your pants off. You can put that blanket over your body, and you'll never know."

The new man turned the tv on in front of him, turned to the browser and chose a porn site, handing the remote to Jerry. He then turned off the lights. Jerry flipped through until he found something he liked: a large breasted Scandinavian girl sucking the cock of an old man. He watched and tried to focus while he saw the edge of the blanket near his feet lift.

There was pressure on his balls and the base of his cock when the man placed his hand on him. This guided the cock perfectly into his mouth, warm and wet, immediately taking Jerry's cock in the long slow strokes he liked when he imagined fucking a girl. He'd never had his cock sucked so completely. He watched the porn, the auburn haired girl quickly sucking the old man's thick cock, his own being sucked better. The man shifted his hands to Jerry's hips, most strokes starting with the top of his tongue on the head and finishing with his lips pressed agains Jerry's balls.

He didn't stop, he didn't slow, he didn't ask if Jerry was almost ready. He just sucked his dick like that cock and the cum inside were the most important thing in the world. He sucked slowly and thoroughly until Jerry suddenly grabbed his hands and thrust his hips while the man sucked in each drop of Jerry's load.

"Oh my fucking god," Jerry said as the man moved his mouth off of Jerry's cock. He leaned back, his wet and flaccid cock hanging off to the side. The man stood up, pulling off the blanket.

"How was that? You've got a great cock," He stood up and walked into the kitchen. It was only now that Jerry saw that he was naked, his short skinny cock fully erect before him. "Do you want a beer?"

Jerry lay there for a moment, surprised at how relaxed he was. He stood and walked to the open kitchen, "sure."

They sat back on the couch, Jerry without his pants, and Michael, as he'd now introduced himself, naked. Michael had grown up here, was fluent in German, read a lot of fantasy. He managed a small electronics store. Jerry was working IT, struggled with getting through the books he read, mostly non-fiction. He'd never been with a man. Michael had gone down on two guys; he'd implied it was more, but he had been talking to a stranger and was very horny, he didn't mind misleading him in the shop. But as he told him, he saw Jerry's cock begin to lengthen. He reached over and began to stroke him as he talked about his job. Jerry didn't seem to mind.

Jerry looked down at Michael's hand stroking his cock. "Can I ask you something?" Michael nodded but was looking at Jerry's cock in his hand. "I have two fantasies, really." Michael looked up at him, pausing his stroke for a split second before squeezing him tighter and starting again. "The first is a great blowjob, which, I mean, that was the best blowjob ever. The second is to fuck a girl in her ass. Would you want to...?"

Michael opened his mouth, and Jerry saw just how hard they both were. "Yes, right now." He went into his bedroom and returned with lube. He squeezed some into his hands and rubbed them together, warming it. He spread it on Jerry's cock, then got on his hands and knees and put a generous amount onto his asshole, rubbing it around in a circle until Jerry leaned up. "This is my first time with an actual cock, fuck me but be gentle."

Jerry pressed the head of his cock into the tight pink hole and moved back and forth a few times until it started to slip in. Then he pushed firmly until his head popped in and put more lube on the shaft of his cock before pushing deeper.

Jerry fucked Michael, gently until they were both ready, and then fucked him like a man who knows who this asshole belongs to. He came hard and Michael jacked himself off, cumming while Jerry's cock softened inside of him, cum spilling from his ass.

They lay on the couch not touching until the cum had dried on both of them, and maybe they'd even fallen asleep.

Now most days, Jerry comes home from work and makes dinner. Usually his boyfriend Michael is there, mostly without clothes, often slowly jacking off unitl Jerry is ready; or doing something in the house with a butt plug in him. It was the early days of the relationship, and they were still fucking once or twice a day; Jerry had begun giving handjobs to Michael and even sucked his dick once, and would many more times. Michael wasn't yet sure if they were in love, but he was thinking about it now as Jerry's heavy balls slapped against his ass and he stroked his cock in long, smooth strokes.

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