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Dean and the Butt Plug (Masturbation Challenge 06)

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Title: Dean and the Butt Plug (Masturbation Challenge 06)
Author: Beren
Fandom: Supernatural
Pairing: Dean/Sam unrequited
Summary: Dean needs to sort a few things out in his head, so he experiments.
Rating: NC17/18
Disclaimer: This story is based on characters and situations created and owned by WB and Eric Kripke et al. No money is being made and no copyright or trademark infringement is intended.
Warnings: unrequited wincest
Author's Notes: Thanks to Soph for the beta. This is 6 out of 31 short fics, all involving masturbation in honour of the Merry Month of May. All fics were written with knowledge up to Hell House, no canon after that was used since that's as far as I've seen.
Word count: 1,394
Link: to other mmom fic

Dean was confused, and if there was one thing he hated more in the world than Sam going off on one about leaving, it was being confused. Knowing exactly what he was about and where he was headed were two things Dean took for granted in his life, but the last few weeks had been making him think. Definitely not one for inaction Dean had therefore decided to figure out what was going on with him and sort it out.

Sam was off doing research things since it was the middle of the afternoon and Dean had told his brother that he was going to follow a lead, only there was no lead and Dean was in their motel room bathroom with the door closed. On the counter was a tube of lube and a sleek black butt plug.

Dean's problem all stemmed from one night in a bar three states away where he and Sam had ended up after a wash out of a hunt that had in fact just been some teenagers getting their rocks off by scaring people. They had crashed into the first bar they found and it hadn't turned out to be quite your normal back woods establishment. Sam had been at the bar when one of the male patrons had first tried to hit on him, and Dean would have laughed his ass off about it if little Sammy hadn't flirted right back.

The fact that both those of the male and female persuasion liked their own sex was not something that bothered Dean in the slightest, but he had never in a million years connected anything like that with his family. Sam having tendencies both way he could have coped with quite easily as well after a few drinks and making himself think it through and not have a knee jerk reaction. Sam was a big boy and could make his own decision. No it was the overwhelming surge of jealously that had hit him from left field and sent him reeling.

Dean had always been straight as an arrow, never even so much as considered that he might be anything else, but when the guy at the bar had touched Sam, Dean had wanted to punch him so hard that he'd be shitting teeth for a week. Dean had rationalised it away by deciding that it was brotherly jealousy in that chicks were fine, but he was the only guy allowed to be in Sam's life, platonic or not. Only over the last couple of weeks Dean had been becoming less and less sure that that was it.

He'd been watching Sam carefully and had come to the conclusion that his baby brother made him think things he really shouldn't be thinking. That still left him with the major question though; the thing that was confusing him: was he thinking these things just because of what he had found out about Sam or did he really have bi tendencies and wanted to find out personally what his brother was packing?

Hence he had decided to try a few things alone before he so much as let Sam get a whiff of what he was up to.

Eyeing the butt plug speculatively Dean could not help feeling a little well of excitement in his gut, and the throb of arousal that arrowed straight for his cock told him that he was going to do this. Of course he could not tell if it was just the illicitness of the act that he was anticipating or the act itself yet, which was the whole point of the experiment.

Unbelting his jeans he pushed them and his underwear to the floor before stepping out of the clothes. He was already mostly hard just from the thought of what he was about to do and he gave himself a quick stroke to make sure. He had looked up the logistics of this on the laptop when Sam wasn't paying attention; never let it be said a Winchester would go into a situation unprepared, but the mystery of what it would feel like was tantalising. Even just standing there Dean can't help thinking that he might already know the answer to his question, he was just being a dumbass and denying it.

Still, he was here, he'd bought the things he needed so he might as well use them.

Taking the butt plug he smeared it with lots of lube; that was one thing he remembered very clearly from the instructions on the internet; lube was his friend. Then he perched on the side and placed one foot on the toilet seat so that his legs were nicely spread. It felt weird to be the one exposing himself and he saw and felt his cock twitch in response.

Feeling around back there he located his entrance and carefully lined up the butt plug with his hole. Then he pushed and was remarkably surprised by the resistance he felt. The couple of porn sites he'd taken a glance at had made it all look really smooth and easy, but the plug did not want to go in. Taking a deep breath he tried to relax; he was going to do this, nerves or not.

The second time he pushed he felt the narrow tip of the butt plug breach the tight muscle and shocks of pleasure radiated from the point of contact, making him pause again. What he had read had been right; it really did feel good. That answered at least part of his question, he did like the sensation of something up his ass.

He pushed a bit more, enjoying the feel of the intrusion and his small victory over his own body. It didn't take him long, however, to come to a halt as he felt a biting pain.

"Too fast you idiot," he berated himself and withdrew the plug a little way.

He'd gone for a medium size plug and obviously it was going to take a little more work for it to all fit inside. He was still hard and throbbing even with the pain, but then he'd always known he had a thing for sex a little rough. Taking more deep breaths and doing his best to convince his body to relax even further he went back to moving the butt plug. It slid in and out quite easily to a certain point and each time he worked it in a little deeper.

When his body finally opened to accept the whole thing, closing around the plug like a glove, it bumped something inside of him that left him gasping. That was something he had never felt before and he had no doubt he definitely liked it. He had had no idea what he'd been missing all these years and if Sammy really was an ass bandit then Dean could see why.

Moving his hips slightly he experimented with the feel of the plug inside him and it did not take him very long to find a move that made it bump that place again. Knowing that he would not last very long with sensation like that Dean took hold of his cock for the final part of his experiment.

In his mind he conjured up a blond god, all firm abs and athletic prowess and focusing on the image he stroked himself. It felt good and the guy in his mind was hot, but there was not that extra magic that he had known with some women; the little spark that made good sex great. He pictured the Adonis pushing into him; imagined that the plug was a thick oiled cock and as he stroked himself he was on the edge, but it was nothing spectacular.

Keeping up the pace with his hand and the rocking of his hips he let the mental image morph into Sam. Blond hair became brown, blues eyes shifted to grey-green and the athletic body flowed into Sam's powerful, lanky frame. At the thought of his brother's cock up his arse Dean came so hard he hit the toilet seat next to his foot as well as his hand and the floor.

He was left panting and dazed and with one very clear thing in his mind; he and Sam were going to have to have a talk, and soon.

The End