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Experimentation

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With Sammy out at school for the day and Dad out on a hunt, Dean was at their latest home alone. A call from his boss at the car shop told Dean he had the day off and now Dean was feeling a little antsy – nothing better to do than sit on his ass and watch TV. After aimlessly flicking through channels all morning, Dean sighed and launched the remote across the room. He was bored and feeling useless…and bored. He popped his lips a few times, drumming his fingers on his knees. There had to be something he could do.

 

After another few minutes of aimlessly lying around, Dean sat up straight on the lumpy old couch, a smile slowly spreading across his face even as his cheeks flushed a light red in response to his thoughts. With only a second of hesitation Dean went into the back of the house where he and Sammy shared a room and bent to retrieve his duffle bag from underneath his bed. Rifling through his clothes, Dean pulled out his hair gel, an old hairbrush he hadn’t used in forever and incidentally forgotten about, a spare knife, and finally what he was looking for, an old issue of Busty Asian Beauties, a place he knew his brother would never intrude on. Opening it to the centerfold, Dean slid out what he’d really wanted – the risqué, distinctly male-centered, obviously gay, magazine he’d smuggled into his bag over three weeks ago. Until now, he hadn’t had an opportunity to look at it and with a few hours yet until Sam returned home, Dean was finally getting his chance.

 

At 18 years old, Dean was only just now beginning to realize his sexual preferences weren’t exactly traditional. For years he’d been conditioned to want girls, women, whatever, to think sleeping with girls was something to be proud of and to brag about, a symbol of his virility, his strength as a man. Even now, Dean was having a hard time reconciling those beliefs with what he kind of knew was true about himself; as attractive as girls could be, they weren’t what he wanted. It seemed muscled lean bodies were more his thing. Problem was, Dean couldn’t be positive because as much as he thought the male form appealed to him, he didn’t have any experience to prove it. He’d been with girls, made a reputation for himself in being with a large number of them, even enjoyed himself, but he had no experience with guys to prove that would be better. The magazine had really been his first chance to prove it to himself, but until now he had never been alone long enough to start experimenting.

 

Standing up, Dean dropped the other magazine on his duffle, turning to sit on the edge of his bed and gingerly turning the first glossy page of the new one. He ran a hand through his hair and breathed deeply, trying not to think too hard about what he was doing. His breath hitched at the sight before him – a man, probably not too far into his twenties, leaning against a wall in only his tank, rucked up to show one dusky nipple, and his underwear, fingers cupped around the hefty bulge of his cock. The man was biting his lip, staring directly into the camera, a light sheen of sweat covering his skin. Dean couldn’t breathe. This was so much hotter than any other magazine he’d looked at before.

 

Forcing a breath through his nose, Dean rubbed his sweaty palm against the denim of his jeans. He flipped the page, finding another young man, this time somehow in an even more provocative pose. Dean found himself biting his lip, so far resisting the temptation to touch his rapidly hardening dick. Another page and he couldn’t take it anymore. Dean dropped the mag on the bed and stood, shucking his jeans and underwear as fast as possible before yanking of his socks and t-shirt off in the length of three heartbeats.

 

He settled back onto the bed, this time leaning back against his pillow and the headboard, his legs stretched out in front of him. When he picked up the magazine again, his right hand instantly gravitated to his groin, timid fingers wrapping around the base and moving in a slow slide up. After that the movements were mindless, uncontrolled; Dean couldn’t get enough. He could feel the blood pounding through his veins, the pulse of it in his cock, the tension in his thighs as the pleasure heightened.

 

On the next page were smaller pictures and some feature articles. He almost flipped right past them when a word caught his eye: prostate. Eyes flicking to the top, Dean’s hand froze mid-stroke. The article was talking about sex and adventurous ways to stimulate that sensitive gland. Shit. The other magazines he had never went into quite as much detail as that. This was starting to seem more like an instructional manual. Where the hell had this thing come from?

 

Dean skimmed the article, extremely aware of the blush covering his cheeks. He had slowly started to stroke himself again, but he couldn’t tell if he was more excited now or intimidated. Feeling his skin prickle in the cool air, Dean’s hips lifted into his hand. Excited it was.

 

Feeling emboldened, Dean shuffled the magazine to the side, sliding down on the mattress so he was lying mostly flat on his back. A few more even strokes to his cock to get his rhythm back and Dean let his legs fall open, parts he usually didn’t think about on display, exposed. Dean’s head rocked back against the pillow, strangely aroused by what he was doing. He continued stroking, switching hands so he could cup and tug his balls, and then his right hand was adventuring further down than it had ever gone before, skimming lightly over the skin, following the crack of his ass down and back up until his finger-tips were resting right over his rim.

 

He stopped. No freaking way was he doing this. He couldn’t.

 

And yet…the fingers were already pressing a little harder, exploring the texture of the wrinkled flesh, massaging the skin even as it retracted under his touch. Dean felt light-headed. He forced himself to breathe, sucking in air while his fingers remained in place. He wanted nothing more in that moment than to go further, to press inside, explore, just touch and experience, but he was nervous. He forced another few breaths and sat up, pulling both hands off of his body. If he was going to do this, he would need something to ease the way. Even with no experience in this area, Dean knew enough to know some sort of lubrication was necessary.

 

Dean leaned over the side of the bed. He saw the bottle of hair gel, almost reached for it and cringed. That stuff was way too sticky to make things even remotely comfortable. Going into the bathroom, Dean returned with a bottle of lotion and some tissues. Biting his lip, Dean once more situated himself on the bed and leaned back, this time with lotion in hand. He eased himself back into it, stroking his cock, rubbing his balls, and then finally returned a finger to his crease, ghosting over the sensitive skin. His lungs froze in action once more.

 

Pulling his hands away, Dean reached for the lotion, globbing some onto his fingers and then reached back between his legs to smear it over his rim. He hissed at how cold it felt, but gradually relaxed as the cream warmed on his skin. For a few long minutes, he couldn’t bring himself to do anything more than massage the skin around his hole, but as he grew more comfortable, Dean dared to press a little bit harder. He held his breath and pressed down with one finger, sinking in only to the end of his nail before stopping. Panting breaths escaped his throat. He didn’t know if he could do this. Pulling back out, he gathered some of the excess lotion on his skin and pressed against his hole for the second time. This time he made it to the first knuckle before freezing.

 

If he did this he would never be able to go back. Dean knew that. He knew, even more than he knew that monsters existed, that if he continued on this path, that he would never be able to go back to women, to being what his father wanted. For a moment, Dean considered pulling out, had even started moving his finger, but before he could consciously make the decision, his finger was pressing deeper, surging within his body and sealing his fate.

 

With a finger fully embedded in his ass, Dean moaned and rocked his hips, turning his face into the pillow to avoid making a louder sound. His heart was racing, a loud thumping beat that felt as if it could escape right out of his chest. Pulling the finger nearly out, Dean wiggled it just inside the rim and whimpered, gasping as he plunged it back inside. This time he didn't stop, simply pulled back and did it again, and again, until he had a built a rhythm.

 

Minutes later, Dean wanted more and so he retracted his fingers and added more lotion, returning with two. He pressed gently, nervous about introducing more width to his tight hole. Rather than the fierce resistance he expected however, Dean was met with a welcoming suction, the two fingers swallowed as deeply as possible in a matter of seconds. A loud moan filled the room. Wiggling the fingers around, Dean tried separating them, pleased when he was able to and then he cut off a scream as a bolt of pleasure shot up his spine. Fuck. That had to be what the magazine was talking about. He’d found his prostate.

 

Slowly, experimentally, Dean spread his fingers again, and when the same feeling didn’t spread through his body, he pushed his fingers back together and plunged them at an angle into his body. After a few erratic thrusts inside, Dean’s back arched off the bed as a primal cry left his lips. He’d found it. For a few seconds Dean kept his fingers in place, dragging them repeatedly over the sensitive area, a scream finally breaking free when the sensation became too much. His body shook and went still, his fingers still buried inside.

 

Pulling out for more lotion, Dean panted. He wanted more. In seconds, he had replaced two fingers with three and was again thrusting inside his body with a bit too much force. Colliding with the nerves again, Dean sobbed and then did it again before leaving the spot alone long enough to try spreading his fingers. Now with three fingers, Dean found stretching his hole was much easier, the muscles relaxing incrementally with each thrust inside.

 

Every thrust heightened the pleasure spreading through Dean’s veins. He’d never felt anything like this before and wanted nothing more than for the sensations to never stop. Legs splayed wide, Dean lifted his hips, keeping the rhythm. Only when he felt the heat pool in his belly did Dean wrap his left hand around his cock, adding to the pleasure surging through his body and finally pushing him over the edge.

 

White stripes painted his belly as his back arched away from the mattress, his hole pulsing around his fingers. Flicking the digits one last time over his prostate, Dean whimpered and collapsed back against the bed, body drained of energy. After a few breaths, he pulled his fingers from his hole and sighed at the emptiness, reaching for the tissues and cleaning up his belly.

 

Sitting up, Dean groaned at the twinge in his ass. Shit, even after all that he wanted more.