Date: Thu, 23 Jul 2020 10:26:40 -0700
From: C <00wcal@gmail.com>
Subject: Jack and Bill Part 3 (gay rural)

Everyone in this story is of legal age. Please remember to donate to
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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.