PLEASE NOTE: This is not one continual story, each chapter is a separate requested One Shot. I have grouped them all together to make it easier for people to read
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You stretched your arms out over your head as you let out a yawn, deciding to call it a night. You were hanging out with Roman and Dean at your house and although you were enjoying their company you could hardly keep your eyes open.
"You're not going to bed are you?" Dean asked as you got up from the couch
"Yeah, why?" You asked
"Well...why don't we do something fun?" Dean suggested
"Like what?" Roman asked wondering what Dean was getting at
"What about Truth or Dare?" Dean said
"Bro, that is so lame" Roman teased
"I don't mean normal Truth or Dare, I'm talking about dirty Truth or Dare" Dean stated
''Dirty truth or dare?'' you asked suspiciously
Knowing Dean, he proposed had something sexual in mind for this game
"Yeah'' Dean confirmed ''So, you wanna play or not?"
"Uh I don't know" you said reluctantly ''I mean I'm obviously outnumbered here''
''Come on baby girl, it's only a bit of fun'' Roman replied ''besides you can always choose Truth''
''Oh so now you're all for it!'' You replied ''Normal Truth or Dare is lame but dirty Truth or Dare is fun''
''You and I both know that Dean won't give up until he gets to play his stupid game'' Roman answered ''So I say we just play it and get it over with''
"Fine" you said as you realized Roman was right ''I'll play''
As the game got underway your earlier suspicions were quickly confirmed. So far the questions had be more than a little sexual and Roman was already stripped down to his boxers from a previous Dare.
"Alright (Y/N) Truth or Dare?" Dean asked looking at you
Up to this point you had resisted choosing Dare in fear of what they (or in particular Dean) would make you do "Truth"
"Okay..." Dean said, trying hard to come up with a good question "Have you ever fantasized about one of us fucking you?"
You were deeply attracted to both of them but you'd never told them ''Yeah i have'' you admitted
"Which one of us?" Dean asked eagerly
"I think you'll find that's two questions" you replied. You knew exactly what Dean was getting at but you weren't going to give it to him, not just yet anyway "Truth or Dare Roman?"
"Truth" he replied
You grinned as you thought of something you had wanted to know the answer to for a while ''How big is it?''
Roman's eye's widened as he caught on to what you were referring too "Big enough to blow your mind and wide enough to stretch you out"
"Oh really?" You asked with a smile
"Truth or Dare (Y/N)?" Dean asked, interrupting the moment
"Truth" you said
"Have you ever fucked two guys at the same time?" Dean asked, smirking
"No" you replied
"Well, there's a first time for everything, right?" Dean said, looking over at Roman and then back at you
. . . . . . . . . . . . . . . . . . . .
[5 minutes later]
"Truth or Dare (Y/N)?" Roman asked, giving you a discreet smile
"Dare" you said trusting Roman more than you did Dean
"I dare you to...make Dean moan" Roman said, anxious to get back at Dean for his earlier Dare to strip to his boxers
"Alright" you said getting up of the couch and making your way over to Dean, who was already fidgeting in his chair with anticipation. You straddled his lap, grinding down on his manhood, making sure to apply just enough pressure ''You like that?'' you asked as his breath began to hitch
''Fuck'' he replied, biting his lip
You wrapped your arms around his neck ''Do I turn you on?'' you whispered, your mouth close to his neck
A deep groan left Dean's mouth and you smiled to yourself as you stood up and made your way back to the couch
"You alright bro?" Roman asked laughing at Dean's expense
. . . . . . . . . . . . . . . . . . . .
[10 minutes later]
The game had escalated quickly and Dean was now shirtless (much to your delight). You were now the only one that was fully clothed and you already knew what was coming next.
"I dare you to take off your bra'' Dean said
''Oh come on!!" You protested
"What?'' Dean replied ''I'm half naked, Roman's half naked; well more than half naked. It's only fair''
"Okay fine!!" You said reluctantly as you removed your top. You slowly unfastened your bra and pulled it off your shoulders
"So fucking hot" Roman mumbled as your bare breasts came into view
"Shit'' Dean concurred, licking his lips ''Truth or Dare Bro?'' he asked not taking his eyes off you
"Dare" Roman said
"I dare you to suck on (Y/N)'s nipples"
Without saying a word, Roman stood up and walked towards you cupping your breasts in his large hands. You let out a faint moan as Roman covered your left breast with his warm mouth, gently flicking the other with his finger
"Fuck the game'' you panted ''I need you both"
Roman lifted his head up and laid you down flat on the couch "Hey, you don't have to ask me twice''
"Me neither" Dean said, unbuckling his belt on his jeans as he made his way over to you
