The Monkey in the Middle, Dean/Sam/OFC; NC-17
Title: Monkey in the Middle
Author: softbluebuddy
Pairing: Dean/Sam/OFC
Genre: PWP - There is no story here.
Warning: 3some, pegging, DP
Rating: NC-17
Word Count: 1830
Beta: carinas_carinae
A/N-This started as a little comment porn ficlet at phantisma’s LJ. Today’s theme was threesome. This prompt which I thought was crazy was SPN-Dean/Sam/OFC-Monkey in the Middle. Anyway it wasn’t as crazy as I thought and decided to expand it a little before posting it anywhere else.
Summary: Dean and Sam pick up a girl and go home with her. After a fairly full evening she lets on that she has her very own harness and strap-on. This gives Dean an idea. Guess the evening’s not over yet…
Monkey in the Middle
Sam lay on the bed. They’d been at it all night. His ass was full of lube and come. He watched Dean and the girl across the room and heard her start giggling.
Dean was helping her get strapped into her harness with the purple dildo when she said the funniest thing. She must still be a little tipsy. “Your brother’s arms are so long he reminds me of a monkey.”
He laughed out loud, turned and looked at Sam and whispered to the girl, “He’s kind of sensitive. I’d appreciate if you didn’t say that loud enough for him to hear you.”
“Oops, sorry.”
“No worries. You know the plan?” Dean asked her after he pulled the leather harness extremely tight and buckled the last buckle.
She nodded her head.
Dean left her then, walked across the room to the bed with a bottle of lube in his hand. He looked at the fucked out face of his brother and reached down and applied even more lube to his juicy, wet ass. He was gonna need it for the next event of the evening.
Sammy moaned because he loved having Dean’s fingers in his ass that had already been fucked open. It felt so fucking good feeling Dean play with the come and the lube in his sloppy, wet ass and rubbing his spot till his body was just humming with sensation.
Dean nudged his brother, “Move, let me get under you and then slide down on top of my cock.”
After getting in position, facing Dean with Dean’s cock in his ass and his ass in the air, Dean pulled Sammy down onto his chest and gave him a slow, wet kiss, then said to the girl, “Okay honey. It’s your turn. Be sure to get enough lube on that dildo. My boy has never taken two at once before. And remember to take it slow.”
The girl, completely naked except the leather harness with the purple strap on dildo approached the bed where Sam was straddling Dean and Dean’s hard cock was already in his brother’s ass.
She grabbed the bottle of lube and climbed onto the bed in between Dean’s open legs and behind Sam. She watched raptly as Dean was slowly fucking into his brother’s beautiful ass while they waited for her to get ready. She could see the shine of all of the come and lube on Dean’s cock on every stroke he slid out of Sam.
Sam had been insatiable all night. When these two guys had hit on her at the bar she thought she’d died and gone to heaven. But, when they agreed to go to her house instead of their motel she really was about as excited as she had been in a long time.
Because she had the leather harness and dildos at home and she was hoping she’d be able to peg one of these guys before the night was over.
They had fucked in almost every combination, with the exception of nothing had gotten anywhere near the older brother’s ass. Apparently Dean was the top in that little relationship. Hell, she didn’t have any problem with that.
Watching Dean fuck Sammy’s ass earlier had practically made her mouth water. And, in fact, did when Dean had let her rim out Sammy’s come-filled ass after he’d dumped a load of come in his brother.
Sam’s hole was so hot and sweet. He was hot and sweet. She’d given him head once and then each of the brother’s had fucked her, in between Dean nailing Sammy’s ass and Sam sucking his brother’s cock. They’d also gone down on her together eating their come right out of her wet pussy.
Fuck, but these guys were hot. Too bad it was a one-nighter. She could totally get used to being their little fuck toy and watching them fucking each other and knowing they were brothers was just about as nasty as anything she’d ever seen or been a part of.
Thinking all of these things as she lubed up her purple dildo, she kept the bottle of lube in her hand and dribbled more onto Sam’s crack.
She scooted up right behind them and told Sam and Dean, “Okay, I’m ready. Lots of lube on the dildo and even more on Sam. I’ve pegged guys before, but I’ve never done DP before either. Gonna take it real slow, okay?”
Putting her hand on Sam’s hip she placed the head of the dildo at his entrance above and a little to the side of Dean’s. As she pushed in slowly she could hear his sharp intake of breath.
Dean was running his hands over Sam’s back and whispering encouragement to his brother, “Sam? Okay. She’s gonna wait a few seconds till you tell us you’re ready. Breathe, baby, come on, I know you can take it. It feels really full for me too with just the head in there with my cock but, Sammy, it is so nasty. Can’t wait till she fills you up and we both fuck you. You still want it?”
Sam listened to his brother telling him how much he wanted to feel that with both the cock and the dildo in his ass, and how nasty it was, but damn he was full already. Didn’t know if he could take anymore.
“Don’t know, Dean. Pretty tight,” Sam told his brother.
“I know, Sammy. Just a little more? Breathe slowly and relax,” Dean told Sam, then pulled him in for a kiss.
The girl took her cue and with both hands on Sam’s hips now slid in another inch. Sam seemed to take it okay.
After several more minutes of Dean soothing and kissing Sam and her dumping more and more lube on the dildo and Sam’s stretched hole, she had worked it all the way into Sam, and basically bottomed out with her pubic bone right up against Sam’s ass cheeks.
“I’m all the way in. How’s it feel?” she asked, really wanting to know.
Sam actually laughed, “Are you kidding? I’ve never been this full in my life. Jesus.” But he smiled at Dean who had remained motionless while the girl worked her way into Sam’s ass and Dean started to move.
“Good boy, Sam. Good boy. Gonna be so good. Feels so tight on my cock. Fuck, gonna fuck you, Sammy, slip and slide all inside your tight ass with her riding you with that dildo, too.”
Sam could feel them start to move inside of him. Somehow they had worked up a tandem rhythm that felt really good. Especially because he was so full his spot was getting hit on every stroke. There was no place for it to hide from the two cocks fucking his ass. Even if one of them was rubber.
Dean was babbling to Sam, asking him if he liked it. “You like being such an ass-slut that you’ll take two at a time? Oh man, how hot is that having a little girl like that behind you fucking your ass at the same time that I’m fucking you? Feel good, Sam?”
Okay, just a little overload here. It wasn’t enough that he was getting double penetrated by his brother and a really hot girl with a strap-on, but now he had to hear Dean calling him an ass-slut?
Out of the blue he heard himself answering, “Hell yes, I’m an ass-slut. Fuck, Dean, so hot having you fuck my ass anyway and having her pegging me at the same time. Jesus it feels incredible. I’m so full of cock, fuck!”
“I know you are, Sammy. I know you are. An insatiable ass-slut. Oh man, this was a great idea. I’ve always wanted to DP, but I don’t like to share what’s mine. But this little girl and her harness are just perfect. How’s she doing, Sam? She fucking your sloppy ass good? She is such a good girl fucking my boy. And you are such a good boy taking it.”
“It’s good, Dean. Really good. She is doing good. So full of both of you. Dean, touch my cock, wanna come. Need you to stroke my cock while you two fuck my ass. Come on, Dean; wanna shoot my load when you are dumping another load of come in my ass.”
Dean smiled. His boy was definitely getting into it now. He was making such nasty noises and Dean could tell he was getting close.
The girl still riding his ass, Dean sliding his cock in and out of Sam’s ass and rubbing against the dildo too, it was so wet and tight and nasty, that as soon as he started stroking Sam’s cock and listening to his brother make those nasty, needy little sounds that he makes when he is getting close, Dean was right there with him on the edge.
“Getting close, Sam? Almost ready? Gonna come for me, baby? Want to feel you tighten up even more on my cock. Come on, Sam, now. Come now, let me feel it.”
Sam always loved listening to his brother talking to him when he fucked him. This time was no exception. He had already been at the edge and when Dean told him how much he wanted him to come so he could feel him clamping down on his brother’s cock and make Dean come too.
“Coming, Dean. Coming,” was all that Sam could get out before he spurted come all over Dean’s chest, stomach and hand which was still jacking his cock.
And that is what pushed Dean over, the feel of his baby brother coming all over him, but even more than that when his ass tightened up before he shot his load and how impossibly tight that felt on his cock with that dildo in there too, he came so hard, and even though he had already come three times before this, he shot such a load of spunk that he immediately felt the friction loosen and his cock sliding in his brother’s slippery ass.
Sam collapsed on his brother’s chest as the girl slid the dildo out of Sam’s ass and kneeling behind Sam and between Dean’s legs, she fingered herself to completion almost immediately. She had been so turned on fucking Sam in the ass and double penetrating him with Dean, and her dildo had already been rubbing on her clit, it didn’t take long and then she collapsed forward resting her cheek on Sam’s ass.
Dean’s cock was still buried to the hilt in Sammy’s ass, which felt looser in the absence of the dildo, and he continued fucking the come and lube in and out of Sam.
“Unbelievable, Sam. You are so fucking hot. Such a good boy for me. I knew you were nervous, but you did it anyway. Give me a kiss. Such a good boy. I loved it.”
And that’s how Sammy became the monkey in the middle.
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