It started not too long after Stanford.
Sam kept his college experimenting a secret from Dean, unsure of how his brother would react to the fact that his baby bro sometimes liked it up the ass. Sam knew that John would have been ashamed, yelled at him for the wrongness of it all, and he figured Dean would be just the same.
Little did he know, it turned out.
They were heading for Bobby’s to get as much R&R as they could before another hunt came up. Sam had quickly ordered the package from a website that promised discretion, calling the post office in Sioux Falls to make sure they held it there and didn’t deliver it to Bobby’s house.
It was easy enough to pick up, since Bobby took a day for himself to deliver a book to another hunter and Dean absolutely did not want to do the grocery store run. Sam happily went shopping, with a pitstop at the post office on the way home.
He opened the box in the car and stuffed it in his backpack after admiring it for a moment, his stomach twisting with anticipation. He didn’t want to take the box inside and risk Dean asking what he’d gotten, better to carry it in his backpack, which Dean rarely looked inside of.
Sam thought he’d done pretty well, actually, with how casual he was when he went inside. He helped Dean unload groceries while his backpack stayed snug on his shoulders. Sam then ran it up to his room, grateful for the hundredth time that Bobby’s house was large enough that he and Dean didn’t have to share rooms when they stayed there.
Sam was a bit twitchy through dinner, feigning restlessness that he used as an excuse to take a shower and go to bed early.
Once he’d grabbed his backpack and a change of clothes, he shut the bathroom door behind him, carefully taking it out of his backpack.
It was purple and long, with a handle on the end for thrusting. There were ridges along it, sure to make Sam’s hole flutter with each in and out movement.
He washed it carefully in the sink as the shower ran behind him before he stripped his clothes off. He coated his fingers with lube, reaching behind to open himself up.
He took his time, the steam of the bathroom calming his body even as he got harder and harder from the stimulation. When he was open enough for the dildo, he slathered it with lube and notched it at his ass, finding the best grip on the handle.
Leaning over the sink, his feet planted wide, Sam slid the dildo inside of him. He bit his free fist to muffle his grunt of pleasure, wanting more already but also keeping himself under control.
It had been so long since he’d had anything inside of him, he wanted this to last.
Soon enough, Sam was fucking himself on the dildo, not touching his weeping cock that bobbed between his legs. He’d have to make sure he cleaned the bathroom floor, with how much precome was dripping from his swollen head.
Just as he was getting close –
The bathroom door opened.
“Dude, how long does it take to sh-“ Dean’s words stopped in his throat as he saw the picture in front of him: Sam leaning over the sink, fucking himself with a long purple dildo instead of taking the shower he’d claimed to need.
“Dean!” Sam squealed, a sound he’d forever deny. He tried to stand too fast, making the dildo uncomfortable inside of him. He turned slightly instead, covering his cock with a hand towel.
Dean shut the door, but instead of shutting the door and leaving, like Sam expected him to, he shut himself in the bathroom with Sam.
A few unreadable emotions crossed Dean’s face before it landed on one Sam recognized. Lust. “Damn, Sammy,” Dean said, his voice smooth as butter. “Why didn’t you tell me you needed a good fucking?” Dean stepped close to Sam, looking around to admire the purple handle that was sticking out of Sam’s ass, as the toy was still snug inside of him. “That’s a nice toy you’ve got there.”
Sam’s eyes were wide, but he was still horny and Dean was standing awfully close. And he wasn’t disgusted by Sam, in fact he seemed… interested?
“Dean?” Sam said quietly, a million questions hiding in the name.
Dean smiled, biting his lower lip for a moment to make it pink and perky. “Want some help?”
Sam’s eyes grew wider, if that’s possible, and he nodded before he realized what he was doing. Dean’s hands were gentle on Sam’s shoulders as he turned Sam back toward the sink, moving him into the same position that he’d been in before Dean surprised him. For a minute Sam wasn’t sure what Dean was doing, just standing there, but Dean was taking his time to admire the ass in front of him.
“Damn, Sammy,” Dean repeated. “Where have you been hiding?” Dean’s hand found the grip on the dildo and he started to move the toy again, making Sam whimper.
It didn’t take long for Dean to find the right angle so that the head of the dildo hit Sam’s prostate with every movement. Sam quickly came all over the floor, teeth marks sure to leave a bruise on his fist with how hard he was trying to keep quiet.
Dean pulled the dildo from his brother’s hole, catching his thumb against the rim to tease Sam just a bit. “Dean…” Sam groaned, his blush covering his entire back. Dean smiled and looked from the toy in one hand to his brother’s ass.
“What do you say we actually get in the shower and you try this thing out on me?” Dean asked, sounding a hell of a lot more confident than he felt.
Sam stood, turning to look at Dean in the eyes. Dean’s eyes couldn’t hide a thing from Sam, not after the years of admiration and devotion Sam had given him. He saw the nervousness in Dean’s eyes, but he also saw the arousal and lust.
“I say that sounds like a wonderful idea,” Sam replied, taking the dildo from his brother. “You need less clothes, though.”
Dean was hasty to strip, the two of them quickly figuring out just how tight the shower was for two grown men and a purple dildo.