Older brother’s “straight” roommate
one of my spiciest stories I have happened fairly recently
my older brother lives with some of his friends in an apartment. I travel to see him on occasion and stay with him when I do
one of his roommates recently moved away for a new job. my brother and the other roommates had a sort of “going away party” type thing. I was invited and went
to preface- Ryan (28), the roommate, has always been straight. he’s always had girlfriends here and there, hooked up on occasion, but never had any long term relationships since I knew him, and he never showed any remote signs of being gay…
Ryan is tall- probably 6’2, extremely muscular, has curly brown hair, and a beautiful smile
as you can imagine, at this party, the drinks were flowing. people were having a pretty good time. Ryan and I started talking about how he needed to “go out with a bang” half joking, but half entertaining the idea of going out to try to find a girl to hook up with
Ryan, like nearly everyone in my public life, did not know that I’m bi. I never really was attracted to Ryan just because he was my brother’s friend, so it’s not like I was planning this whole thing out
we were both somewhat drunk but sobering up, still joking about finding some horny girl to tag team on tinder or something
Ryan started complaining that no one on tinder was responding, and none of his usual hookups were responding either
that’s when I decided to make a joke that, until I said it, I didn’t realize i was actually kinda thinking about it…
”well if you can’t find any girls I’ve got a nice ass bro don’t worry” I said, intending to just make a gay joke like a lot of close friends do
he played along
”sure bro. i know you wouldn’t leave me hanging. thanks bro” he responded
we shared a laugh over that, but then my tipsy mind shifted. it shifted entirely. I now realized how sexy Ryan is. if he actually wanted to fuck me, I’d let him. not only that, but my drunken brain wants it to happen.
i couldn’t focus on anything else after that
the party was winding down. almost everyone was gone and the roommates were starting to go to bed. my mind was wide awake
”so no play for you tonight?” I said
”nah man nobody answered. it’s alright I’m tired anyway” he answered
I decided to be bold and see how he responded to another joke, basically saying the same thing as before
”offer still stands bro! I’ll help you out don’t worry” I said, keeping my voice lower so no one heard
”yeah bro for sure I’ll take you up on that right now let’s do it” he responded, still very clearly joking
“you’re joking but you also know my ass is fat… don’t pretend like you don’t know that” I said back, pushing things a bit more
”yeah bro bring it over here then!” he said, still playing along with the joke
i too decided to continue the joke. I continued it by walking over to him and shaking my ass in his face as he sat on his bed
”you know you want it bro. you know you want it” I said, taunting him
he jokingly smacked my ass
”alright bro that’s enough. I’ve gotta go to bed” he said, effectively shutting down what I almost thought was progress
“you’re really gonna just go to bed without getting your nut?” I asked, now almost throwing caution to the wind, wondering when he’ll realize I’m not even joking anymore
”hey man, you can’t make the chicks answer, you know?” He said
“I’m saying though, you don’t need them bro. you‘ve got everything you need right here” I said as I turned around and jiggled my ass again
”yeah yeah bro whatever” he said, brushing it off
”you wouldn’t last 30 seconds in here bro” I said back
”alright bro… I think I need to go to bed” he said back
i thought it was lost, but at this point, I couldn’t tell if I’d made it obvious enough that I was serious
”just let me take care of it. I’m telling you you won’t last 30 seconds bro” I said
”what is this about?” Ryan said with a chuckle
”nothing… all I’m saying is if I bounced on it right now, you’d get your nut, and I guarantee it would be less than 30 seconds”
”yeah right dude… goodnight” he said back
”what are you scared because you know I’m right?“
”I’m starting to think you’re serious…” Ryan said with a concerned look
“I just know I’m right is all” I said, conveniently dodging the question
then, the tide turned. he tried to call my bluff.
”take your pants off then tough guy. I know you’re just fucking with me” Ryan said
”I’m not scared of you bro” I said back
i immediately slid down my jeans and underwear with them, facing away from Ryan, presenting him with only my ass
”you’re the one that’s scared. you wouldn’t last 30 seconds in this” i continued to taunt
there was a pause. a pause long enough to make me wonder if he was actually checking me out
”yeah right bro. I still don’t believe you. anyone can just moon someone else. you’re full of shit” he said
“I’ll sit on your dick right now bro. I’m not scared of you. you’re doing all this talking now… take your dick out and I’ll sit on it right now” I said back to him, trying my hardest to invoke his competitive nature
”you’re full of shit. as soon as i pull out my dick you'll fold. I’m not scared of you either bro” Ryan said back
and then he did It. he pulled out his cock. it was still mostly soft, but I swear it was at least a little bit of a chub… and now all I had to do was win the game of chicken
i walked backward toward Ryan, bare ass out
”just tell me when to stop because I know you’re gonna chicken out” I said
I got no response from Ryan and kept backing up, backing up, backing up toward him. only a couple steps left. still nothing.
I made it to him, and began to lower my ass down toward his cock
“last chance bro. you know i wont lose to you” i said
”you wont do it” he said back
i finished the job. I sat down basically on his lap. on top of his soft cock
but as soon as I sat down, I felt it. I felt a notable, unmistakable twitch beneath me
i stood back up and turned around, my own cock still out and almost fully erect before I could even notice it
”told you I would bro…” I said to him
”I can’t believe you actually just did that. i didn’t think you’d actually…”
I cut him off
”you started getting hard right away. youre not lasting 30 seconds I guarantee it” I said
“I was not getting hard bro. and you know I’d last longer“ he said back, now entertaining my bait question
“prove it then. I just proved my dare”
“you’re not serious” he said back
”I know you've got condoms in here. throw one on and put your money where your mouth is”
“dude… I’m not doing that… what do you mean” he said
”fine. take your loss then. you’re just scared”
without a word, he got up, went to his nightstand, grabbed a condom, and tore open the package. he was now hard. he was liking this more than he wanted to admit…
he didn’t even need to jerk himself to get fully hard. he rolled the condom right on. he grabbed some lube and put it on his cock
also, I should mention, Ryan‘s cock was fucking thick. it was pretty average length, but thick like a fucking soda can almost…
”sit down bro. I’m making you put your money where your mouth is” I said
”i know you’re not gonna do this. go ahead. do it. I know you won’t” he said back, lying back and presenting his now fully hard cock to me
without a word, I walked over, grabbed his cock, and sat down on it.
no words were exchanged. just surprised gasps from both of us reacting to what had just happened
his cock filled me to the brim. like i said, it was fucking thick. going from nothing to his cock was admittedly a bit painful, but I was so fucking turned on I didn’t care
i sat all the way down. ryan’s cock was now fully inside me.
i began to bounce. my feet were off the bed standing on the ground as i squatted up and down, having to stay at a slower rhythm to keep quiet with the roommates
still no words exchanged. I was just doing my best to take in the sensory overload I was experiencing. a guy I’ve known for years to be fully straight was stretching out my asshole with multiple other people I’m close with just on the other side of the walls.
not long after, Ryan’s breathing became quicker. I felt him get even harder. I felt him begin to tense up.
before I knew it, I felt it. I felt his cock pulsate and begin shooting his load into the condom inside me.
we were both struggling immensely to stay quiet. I wanted nothing more than to scream out with pleasure, but I had to stay completely silent, and so did Ryan
after a few powerful shots of cum that I felt from his cock pulsating, Ryan grabbed my hips and thrusted himself into me powerfully for another 30 or so seconds until finally, he went limp, heavy breathing, slumping onto the bed, and his cock finally slid out of me
i must say- I have never seen a condom look so full in my life. I would’ve loved to have seen just how much cum that would have been on my face or my chest.
”that was at least a minute. told you bro” Ryan said, breaking the silence
without really talking about the insanity that had just taken place, we cleaned up, and I left.
Ryan moved away about a week later. he will still come back on occasion, and we have since had some more experiences, and absolutely no one knows about them
thanks for reading if you made it this far ;)