Everyone in this story is of legal age. Please remember to donate to Nifty to keep you, and the stories, cumming!
Jack woke up with the bed sheets stuck to him. He came twice in bed the night before and after smearing his skin all over with jizz, he'd fallen asleep like that. Now he pulled the sheets off and dumped them in the laundry hamper before washing the dried cum off himself. In the shower, he tried to figure out what was going on with him, but soon was distracted by his growing erection. Of course he started stroking it, his soapy hand sliding up and down the shaft and over the sensitive head. But he didn't want to cum in the shower, he wanted... something else. He wasn't sure just what, but the experience with Bill had awakened a curiosity in him. His fingers found his asshole and he circled around it before slipping a finger slowly in, just a little at first. Soon he had it in as far as he could and the feeling was like nothing he'd had before. He had to try something more, something bigger and thicker, and he started thinking about what that might be. A cucumber, he thought, a cucumber would be perfect, but what would he say to his mom? Hi Mom, just heading out for a picnic and thought I'd take along a cucumber if that's okay? Too weird. He'd have to wait until his parents had gone to work and the house was empty.Coast clear, Jack grabbed a cucumber that didn't look too big from the kitchen and headed out to a spot in the woods behind the house where he regularly went to jerk off. He'd slipped a tube of KY Jelly that he'd found in the back of one of the bathroom drawers in the pocket of his cut-offs. Jack liked the feeling of wearing nothing but cut-offs when he went out into the woods alone - no shirt, not underpants, just sneakers and shorts. He slipped a hand up under the cut-offs to fondle his balls and thickening cock as he walked out past the garage. If a neighbor saw him carrying a cucumber into the woods, they'd might think it was a strange snack for a guy to take into the woods, but he doubted they'd guess what he was really planning to do with it. Jack sat in his usual hidden spot behind some thorny bushes. There were a couple of well used porn magazines stuck under some leaves, the pages warped from cum and exposure to the elements. Jack pulled his now hard cock out of one of the leg openings of his cut-offs, the soft frayed fabric rubbing nicely over the sensitive head of his erection. He stroked his hard-on as he pulled the shorts aside to get at his asshole and began tickling that sensitive spot with his finger. It felt especially sensitive - tingling and hot. He squeezed out a dab of lube and slid a slippery finger into himself, gasping at the sensation. Ready for more, he slicked up the cucumber he'd brought - he thought he'd chosen the smallest one, but now it looked big and he wondered if it'd ever fit. His asshole felt so tiny and tight, almost like it wasn't a hole at all, but now he needed it bad. He slid the tip of the thing in just an inch, feeling his hole stretch to accommodate it. His cock had never been so hard and he stopped stroking, afraid that he'd cum too soon. He withdrew the cucumber and then slid it back in, but it wouldn't go any farther, the tight muscles holding it back. He got into a squatting position and, angling the cucumber against the ground, pushed himself down onto it. It still wouldn't go, but he started moving on it so that it slid in and out a little, the way his buddy Bill had on his finger the day before. Though it wasn't really in him completely, it felt very good, and his cock was dangerously hard, swinging up and down as he moved. He tried to focus on relaxing his ass and when he sat down with a little more force it suddenly pooped past his clenching sphincter and into him. Jack yelped at the sharp stab of pain. He wanted to pull it out, but he also wanted more of it in him, so he just held very still for a moment, his ass clenching and his cock throbbing. He imagined what someone walking through the woods and happening upon him would see: a young man on the ground, nearly naked, his cut-off shorts pushed to one side, his obscenely hard cock pointing to the sky and a cucumber stuck halfway up his ass! It was a nasty, naughty thing and it got him even more turned on to think of it, his head was clouded with lust. And now the pain was subsiding and without deciding to, Jack began moving on the cucumber. It was like instinct taking over and it felt so good now. He took a little more into his ass each time he sat down on the thing and then it went in far enough to touch something and he felt incredible pleasure, like it was stroking his cock from the inside. He moaned and rode on, grunting each time the cucumber hit the spot. He was really fucking himself now - he'd though only girls got off on fucking themselves and it made him feel extra perverse and sexy and made him bob faster on the thing, jamming nearly the entire length of it into his tight, stretched asshole. And then, without even touching his cock, he felt an orgasm coming. Suddenly he was past the point of no return and his cock swelled and throbbed and he felt his asshole clenching and watched the spunk rocket out him. Spurt after hot, messy spurt flew into the air and splattered back down onto his heaving belly and chest. He pulled the cucumber out as he finished cumming and collapsed onto the dirt. He would need another shower and he knew, despite the creeping guilty feeling, that he would need to experiment more.