Jump to content

Roleplay and fantasies


bostonman
 Share

Recommended Posts

I thought it might be fun to start a thread on this topic. (I thought of this, actually, based on the current "dumb jock" thread in the Deli section, but didn't want to hijack that thread, so here we are.) I've always been a big fan of roleplay and fantasy scenarios - perhaps because my biggest first exposure to porn as a teen was with porn novels and "letters" publications, more than picture mags or porn films (though of course I saw those too). Making up the story for the sex to happen around could/can be as titillating as the sex itself. Some of us may fantasize more about the sex itself without much to go on besides that, for me, it's much more fun to create the whole situation.

 

So, I thought it could be hot to describe some fantasy/roleplay ideas - stuff we've done, stuff we've thought about. For those of us with that kind of creative yen who want to share. Maybe not full stories a la Nifty, but at least the gist of the idea. Or of course actual roleplay enounters that we've enjoyed, etc. I'll have fun posting some of those, and hope that others out here will do the same.

 

Currently I have this hot fantasy going about someone in my building. He's in his late 20's, actually my landlord's son, who still lives at home, and who does most of the handywork around the apartment when needed. They live on the first floor, I'm on the 3rd, in an old 3-family style house. He's very straight as far as I know - has been in a few relationships with girls over the time I've been here. I'm pretty sure he knows I'm gay, but has never said anything about it (I'm sure he's mature enough not to care, frankly). Very friendly guy, attractive. Irish, tall, black haired. My fantasy is that he's secretly curious, and that I actually see an ad he's placed on a local meeting site, looking to get a blow job from a guy. I take the chance and let him know he's welcome to spend some time with me if he'd like - and amazingly he takes me up on it. I imagine the small talk that might happen beforehand (maybe he even admits that he did have a college buddy blow him once, and he wanted to try that again), and love to think about the maybe sheepish way he gets undressed, etc...what his cock might be like, and what it would be like to suck him. I think about the little vocal reactions he might make, and maybe the nice surprise of feeling his hand gently caressing my head (probably the way he does with girls lol). I think about edging him a few times, then him almost begging me to get him off as he doesn't think he can hold back much longer. So I oblige and finish him off - imagining that I can feel his cock pulse as he starts to shoot, and what that load would be like as I swallow it. How he thanks me afterwards and sheepishly gets dressed and goes, but intimates that he might want to do this again sometime. Which leads me to thinking about variations on the theme as we wind up doing it pretty regularly.

 

And of course in real life, he'll never know I have these crazy thoughts about him. ;)

 

I do have a roleplay I did about a first-time blow job that I'll post about later - one of my all-time favorite roleplays I've done.

Link to comment
Share on other sites

So – this was a roleplay I did with a guy who lived down the street from me – we had met several times before, basically I just sucked him off each time. I think he was around 30, but looked younger. The roleplay idea was that he’d be a straight college student curious to get his first bj from a guy. We played with the idea that I had already been meeting with one of his friends, who had told him about me, and now he was trying it out. We also decided that it would be fun to keep the roleplay going from the time he came over through the time he left – we wouldn’t go “out of character” at any point.

 

So, when I greeted him at the door, he was this typical college boy. We shook hands, I invited him in. He was polite but clearly nervous. He reminded me that his friend had told him about me and that he was curious about trying this out. We sat down for a few and made smalltalk about school, girls, etc – his answers tended to be a bit reserved, and he was playing games on his phone to distract himself from the situation at hand. (I really enjoyed this take on things by the way.) Finally I asked if he’d mind if I touched him a little, and he didn’t object. I ran my hand over his upper body for a minute, and I could feel him tense up, but he didn’t stop me. Still tense as I put my hand on his thigh and rubbed a little. He kept playing on his phone. I reassured him and told him he could stop me if he needed to. I ran my hand over the crotch in his jeans. He was already hard. I played with him like that for a minute. He was still tense, and I could hear him breathing. But then he seemed to relax just a bit and sat back a little and spread his legs a bit. I played a bit more, and asked again if he thought he wanted to try getting a blow job. He quietly said yeah. I suggested we go into the bedroom, and I led him in.

 

He didn’t get naked all the way – just sliding his jeans and briefs down so that they were around his ankles. Too nervous and guarded to want to really take his clothes all the way off lol. I complimented him on his boner, which in real life was really very nice – maybe about 6, a little on the thick side, and very very stiff, standing straight out. I had enjoyed sucking him in real life, and was now looking forward to doing it in this roleplay context. In real life, he liked to remain standing as I knelt, and it was the same way with this game of pretend.

 

So I started to go down on my imaginary college boy. Although this was his first bj from a man, it wasn’t clear as to whether he had done this with girls before – maybe so, or maybe this was his first actual bj. But it was clear that he liked it. Again, his responses were a bit reserved, just as a nervous straight boy might be in this situation – but he did keep muttering “feels good” under his breath. A lot. I was getting very turned on by the halting way he was responding, actually. I stopped at one point just to admire his cock and play with it a little. I commented on how incredibly stiff it seemed, and how lucky the girls were to get boned by it. I saw him smile at at that. Then I went back at it, not wanting it to end, but all the same, eager to get his college boy load and figuring that he might not last much longer anyway. He started to grunt a bit more and I knew he was close. And then he shot – perhaps the first time he had ever been able to shoot into a mouth. Very hot. Nice load - just as in real life with this guy, of course – but pretending it was from this curious straight kid made it even hotter.

 

His cock was still hard when I stopped, and I asked him if he thought he wanted another bj. He hedged, clearly embarrassed about what had just taken place. But he did stand there for another minute, and I did start to suck him again. But then he pulled away and said he had to get going. He awkwardly pulled his pants back on, thanked me, and was on his way. Typical straight boy, a bit confused about his feelings after getting blown by a guy for the first time. I’d probably never see him again, but maybe he’d eventually come back. I like to think the he went back to his dorm and jerked off thinking about what had just happened, his thoughts torn between having loved it and still being unsure if he should have done it.

 

In real life, I then emailed the guy to tell him how awesome he had been – the blow job was great as always, but I was particularly amazed at how well he had played the character. He really was 100% believable.

 

We met several times after that, and I always wanted to do that kind of roleplay with him again. But he didn’t seem to want to – maybe he was a bit embarrassed about the whole thing, or maybe he just thought it was too special to try again. But I have the memory to savor – and although I’ve done scenes that were much more involved sexually, the way he so perfectly captured the essence of the curious straight boy was so good that I still consider it one of my favorite roleplay sessions.

 

And it's led to further fantasies as well. Like thinking about another session where he came back, but his friend came over with him, and I blew both of them as they watched each other get done. Endless possibilities. :)

Link to comment
Share on other sites

An escort couple, now retired (why do my favorites always retire? Is it me?) indulged me in a manhandling fantasy. They'd just had a new shower installed, big enough for several people, and we played out gym shower. One grabbed me from behind and bear-hugged me, while the other soaped me up while I struggled. He moved down & started blowing me while the other guy rubbed his cock against my ass. The pulled me over to the bed, tied me down, and tag-teamed me.

Link to comment
Share on other sites

An escort couple, now retired (why do my favorites always retire? Is it me?) indulged me in a manhandling fantasy. They'd just had a new shower installed, big enough for several people, and we played out gym shower. One grabbed me from behind and bear-hugged me, while the other soaped me up while I struggled. He moved down & started blowing me while the other guy rubbed his cock against my ass. The pulled me over to the bed, tied me down, and tag-teamed me.

 

If I had a big enough shower, I might be into trying something like that. Not the tying up part, but the horsing around in the shower stuff sounds fun.

 

BTW - the object of my first post, the landlord's son, stopped by this afternoon to check the smoke alarms, etc. Just kinda funny after having just posted the fantasy about him. (And no, he really did just come up to check the alarms.)

Link to comment
Share on other sites

In terms of jock-oriented roleplaying, I've done a few that have been very hot. I hired an escort once (retired now, I think) who played a very credible young jock who was conflicted between enjoying his foray into male/male sex and yet regretting it as well - I enjoyed feeling like every time he grunted with pleasure he also felt like his masculinity was being taken down a peg. The sex was fun and the reactions were even more fun.

 

I've done "starfucker" fantasies a few times as well. I remember hooking up with a guy once who was pretending to be Drew Bledsoe (Patriots quarterback before the Tom Brady era). I don't honestly remember that much about what we did, except that "Drew" really wanted to fuck me, and I wasn't going there (that was around the time that I decided I really just didn't enjoy being fucked, no matter how I tried it). But of course the idea of being fucked by a star pro quarterback was smoking hot, lol. We compromised with him lubing up my thighs and giving me a good strong football stud humping between them - and actually, that was very very hot.

 

But one I do remember vividly - an online conversation with a potential hookup about our shared interest in baseball studs led to a fantasy session with him playing the then Sox captain/catcher Jason Varitek. We played that I was a fan getting to talk to him after the game. At first, it was all baseball talk, with him being rather boastful, etc (that attitude might have been obnoxious in real life but in the fantasy it was hot). Then out of the blue he started pawing his crotch and saying something about needing a blowjob. At first I didn't respond to that, but soon enough he brought it up again, saying that if I really wanted to show how much of a fan I was, I'd help him out. I pretended I had never done this before - he assured me he'd teach me. He unzipped and pulled his bone out, and had me kneel in front of him. He put his strong athletic hand on my head but then guided me to his cock gently (we had talked beforehand about loving that dichotemy between being a tuff jock who could also be very sensual), telling me to suck it nice and slow. He guided my head a lot. "Jason" clearly liked it slow, and very very wet (things got really slobbery and messy lol). He would make little cute baseball references - things like "suck that bat" or talk about scoring a home run, etc. A few times I remember he pulled out and batted his cock against my lips and tongue - he joked about that being me taking "batting practice." The end of the session was particularly goofy and sweet - when he was ready to score his "home run," he pulled out and aimed at my Sox jersey, "autographing" it with his cum. I have to admit that I kept that cumstained jersey around for a good while before I finally decided to wash it lol. If it wasn't the real Varitek, it was a very fun memory of a fantasy version, and I had the stained shirt to prove it lol.

Link to comment
Share on other sites

loving these fantasies, B-Man!....sometimes I can't even tell where the real and fantasy starts and ends in your text!!!

 

Ha! Not for nothing, but I have been told a number of times over the years that I should write porn professionally. But as far as what I'm writing here about my actual roleplay experiences, I'm trying very hard not to embellish.

Link to comment
Share on other sites

  • 1 year later...
  • 9 months later...

I love role play.   I used to teach high school.   In one of my favorite fantasies, my fellow teacher (the stud football coach) is on the verge of a possible state championship run this year with a major stud QB who's a 5-star recruit and trying to decide between several top notch D-1 programs who have made offers.   2 have told the coach they will hire him as the QB position coach at the college level if he "guides" the QB to their program.    The problem for coach?   We're a "no pass, no play" State and this star QB has an F in my class with no way to get to a passing grade in time to get to pass and play this semester.  Coach sends me an email and asks if he can come by my house to talk to me about the kid's grade.

He does come by, definitely dressed to seduce, but the teasing and seduction do not work.   Don't get me wrong, I love looking at his great body and even the feel of his muscles he invites me to touch, but I'm not willing to risk my job for that.  He finally figures out that if I'm going to risk my job, I'm going to need a lot from him and he gives in to that!    In my mind, the coach not only gets the kid a passing grade but actually gets him an A (but that involves full access to coach's body for the whole semester, not just today).

 

Link to comment
Share on other sites

Create an account or sign in to comment

You need to be a member in order to leave a comment

Create an account

Sign up for a new account in our community. It's easy!

Register a new account

Sign in

Already have an account? Sign in here.

Sign In Now
 Share

×
×
  • Create New...