(All involved were over 18 at the time of the events)
I was inspired to write this story based on a similar one I read here recently. In other words, what happened in that person's story was pretty similar to something that actually happened to me in real life.
My co-worker/friend and I were out of town on a job. The company only paid for one room, not individual rooms, which was no big deal because that's how it always was. This particular time, my friend and I had made the rounds at the local bars and a strip club, but were now back chilling in our room.
He told me that him and his girlfriend recently broke up, and he shouldn't have gone to the strip club because now he was horny as fuck. I said, "Well, jerking off is the usual remedy for that." He said, "Yeah, I know." but then said jerking off just didn't cut it sometimes. Then he started asking me about the pros and cons of being bi, which he knew I was.
I said being only straight or only gay was like ignoring half the menu in a restaurant, the way I looked at it. Then he asked me if I ever let a straight guy just fuck me, "you know", without getting fucked in return. I said maybe not a whole lot, but a few times, yeah.
Being the dumb ass I was, I just then realized what he was getting at. Most people would have seen it way before that, but no. So I said "Sooo, you're wanting to fuck, is what you're saying?" He said, "Yeah, would that be cool?" I said, "Well fuck, man, you can't just spring that on somebody like that." He said, "My bad, just forget it."
I said, "I'm not saying I don't want to do it, but maybe you need to be a little smoother than that in the future." He said, "Nah, I was just fucking with you anyway. We're cool."
So we watched TV for about 30 minutes, and I could see him out of the corner of my eye rubbing his dick through his pants. I was wondering if he was planning on just cumming right in his pants or what. It was pretty comical.
After another minute or two he said, "So, uh, about before. You think we could go ahead and do that or what?" I laughed and said, "Well, you're the horny dog that's jerking off through his pants, so it's kind of up to you whether you want to do it or not." He said, "Uh, yeah, I guess so."
I got some coconut oil out of my bag. He stood up and walked over to my bed. He said, "So how do we go about this?" I said, "The usual way. You don't know how to fuck?" He laughed and said, "I meant, you know, what position or whatever." That was a little bit surprising because in my limited experience with purely straight guys, almost invariably, they wanted to fuck you doggy style. That was the easiest way to pretend you were a girl, I guess. Looking straight down at your ass while they were fucking.
He just stood there. So I said, "Did you have something in particular in mind?" He said, "Well, I guess so. If you're cool with it." I said, "Spit it out, man! We're going to be here all night playing question-and-answer."
He said, "It'd be cool if you laid on your back and let me get on top of you and fuck you kind of missionary position." That was REALLY surprising. This guy and me that used to fuck (just a fuck buddy, I guess) did that quite a bit, but never once, ever, had I heard a straight guy say he wanted to do it like that.
I said, "Ok, that's cool." I stood up and took my shorts and underwear off and laid back down near the edge of the bed and pulled my knees up toward my chest. I said, "Like this?" He said, "Hell yeah, exactly like that."
He dropped his pants and underwear. His dick was hard as a diamond. He stepped closer but made no move to actually stick it in. He said, "So, uh..." I said, "Holy shit, dude. You've never fucked before. Now everything makes sense. You have no idea how to fuck." He laughed again and said, "Yes I have, I'm just not sure if this is kind of like the same thing or what?" I said, "Fuck yes, it's like the same thing. To fuck, you just, you know, start fucking."
He pressed the head of his dick against my butt hole and started pushing. It went in. He pushed it further. He said, "That doesn't hurt?" I said, "A little bit yeah, but go ahead."
Instead, he laid on top of me. We were face to face. Very highly unusual, like I said. Then he started fucking for real. Now it was my own dick that was hard as a diamond. He reached down between us and gripped it with his hand. Not jerking me off, just holding it. Not really squeezing it gently but not hard either. I thought it was a little bit odd, but I wasn't complaining.
Suddenly he said "Fuck, dude!" and jammed his dick in balls deep and held it there. I was amazed. I said, "What the fuck? That wasn't even 20 strokes." He pulled his dick out and laughed and said, "I told you I was horny as a motherfucker! I wasn't bullshitting." I said, "Yeah, I see that."
He went to the bathroom and came back out with his pants up and flopped back on his bed. I said fuck it, and just left my own off. About another 30 or 40 minutes of watching TV, and he turned to me and said, "Hey, uh..." and stopped. I said, "Are you fucking serious? Again?"
He laughed but stood up and took his pants back off, I guess assuming (rightly, I guess) that I wasn't going to say no. He came to the side of my bed and just stood there. I said, "Same thing?" He said, "Yeah, if that's cool." He acted like he was about to stick it in, but then stood back upright and looked down at his dick. It was only about 3/4 hard.
He looked at it and looked at me. I said, "Oh, for fuck's sake." I sat on the edge of the bed and started sucking his dick. After about a minute, he said, "Ok, that's good." I laid back down on the bed and pulled my knees up.
This time there was no fucking around asking what to do, he got straight to business. And he was seriously getting down to business. He was alternating between slow fucking and pounding. My own dick was hard as a rock, of course, since I'd never jerked off or anything from before.
After about 5 minutes of fucking, he reached down between us again and gripped my dick. He was squeezing it, then relaxed his grip, then squeezed it again, over and over. Like I said before, it was a little odd, but it felt good, so I didn't say anything. After a minute, he said, "Do you want me to jerk you off?" I said, "Hell yeah, I want you to jerk me off." He said, "Where's that coconut oil?" I said, "I have no idea, it's wherever you put it."
He fished around under the edge of the bunched-up blanket and came out with it. He lay back on top of me and was giving me what I would call a pretty damn decent hand job, all while he was fucking me like he really meant it. He said, "Are you about to do it?" I said, "Yep." and did just that, the cum squirting on both of us, but mostly my stomach.
He let go of it and started pounding like he was trying to break the bed. After a minute he said "Fuck!" and jammed it in and held it there. This time he didn't immediately stand up. He lay on top of me breathing hard then finally did stand up and said "Thanks, dude." I laughed and said, "No, thank YOU. That was a seriously nice fucking and a hell of a hand job too."
He looked sheepish and said, "About that. Uh..." I cut him off and said, "It's a fine time to give me the "Don't tell anybody" speech after you've cum in my ass twice and given me a hand job, don't you think?"
He just laughed and said, "Nah, it's not like that, I was just going to say..." I said, "Yeah, I know what you were going to say. No, I'm not going to tell anybody. Who in the fuck would I tell, your mom?"
He said "Well, anyway, you think if we go out of town again, we could, uh, you know?" I said, "Hell no. I'm not about to be your cum bucket." then realized that sounded like more of an asshole than I meant to sound. So I said, "Yes, I mean, sometimes, yeah, but I'm not bending over every time your dick gets hard."
Sure enough, he didn't always bring it up and want to fuck, but occasionally he did. I found out later what the trick was. It had nothing to do with him having a girlfriend or not, it had to do with whether we went drinking, then to a strip club, then back to the hotel with nothing to do. Whenever that sequence of things happened, that's when he'd want to fuck. Back in our hometown, he pretended that never even happened, only when we were out of town and only when we did that first (drinking and strip club then bored in our room).
Anyway, there's my story that I mentioned before that I was reminded of by another story I saw here. I don't claim to be Mr. Expert In The Art of Fucking or anything, but for one reason or another, an amazing amount of interesting things have happened to me if anybody would be interested in hearing about some of them.
