I’ve only had one successful role play experience. The guy I was chatting with—through Manhunt, but of course—was a beefy, hairy daddy type, and he told me he’d be coming to my place directly from the gym. As someone who watches way too much porn in my spare time, I suggested we do a simple coach/player scenario. He would catch me in the shower and “punish” me for misbehaving.
So there I was, soaping up every inch of my body, playing with my hole and stroking my hard cock. “BOY!” I hear someone shout from behind the shower curtain. He chastises me, as I grab a towel and quickly dry off, apologizing profusely and telling him I’ll do “whatever it takes” to stay on the team.
I start doing push-ups, he starts rubbing his crotch, and before you know it, I’m on my knees swallowing his uncut shaft down to the base, looking up at him dutifully and asking if I’m doing a good job. “I’ll do whatever it takes,” I repeat, as I arch my back and stick out my ass for his approval.
This, surprisingly, did not lead to him fucking me. (He actually came back a few weeks later to get fucked by me.) We swapped blowjobs, shared a few kisses, exchanged rimjobs and, eventually, broke character and got to know one another beyond our fictional personae. To this day, it’s an experience that I’ll think back to when there’s no other visual material (aka porn) available for my masturbatory purposes… Grr, I’d really love to see that guy again and go for another round!
Hmm, does that make it clear where I stand on this Hot or Not topic? I am all about role play! Wherever you may stand, leave a comment and tell me about some of your best (or worst) experiences embracing a role play fantasy. Feel free to tell me all of the juicy details. All of them.
– Dewitt
Photo credit: Cocksure Men
Check out two role play scenarios and discuss your personal experiences below:
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Jason Prode and Austin Ryan play coach/player for HOT DADS HOT LADS:
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Mike De Marko and Connor Maguire play patient/nurse for COCKSURE MEN:
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I’ve done it – can be really fun but also really uncomfortable unless both parties are totally into it. No bigger turn off than over-acting a part too. My ex and I once did a role play where he was straight and he and his girlfriend owed me a lot of money. He couldn’t pay up so… It was pretty amazing.
firstly very nice story dewitt hehe fo me tho have never done ny role play esk stuff i think its cause if someone yelled at me to suck them off etc i wud start laughing lol i wudnt take them serious at all…..i have dressed as a school boy to get a guy i liked cause i knew he was into the uniform so showed up on his bday in it hehe but that was just se with a uniform on……fun to watch in porn tho hehe
I love roll playin almost can’t stop myself majority of the time
Role play is fun but eventually someone says something over the top, I get the giggles and it’s all over.
Did a role play once where I pretended to break into the guys house,he caught me, I had to do things to keep him from calling the cops. It was fun,would do it again.
Role play with friends and FB’s is wild I love it…. Makes the experience much more exciting and erotic…
lol :3
Connor MacGuire can be my coach/boss/doctor/fireman/ teacher/whatever.
I’d like to play doctor with Connor Maguire.
The magic was disappearing from the relationship with the ex. I had been at work all day, but got real horny so decided to make an impromptu stop at the then-bf’s house. I showed up in a full suit and tie and knocked on his front door. When he opened it, he asked me what I was doing.
I immediately went into character (unknown to him) and started talking about how my tire had blown out in his front yard. Since it was raining, I ask to come in and use his phone since my cell wasn’t getting great service. He let me in and seemed to still be unsure of what was going on. I “called” the tow truck and they said 45 minutes to an hour.
He offered me a towel (it was really raining) to dry off and I accepted. He offered to take my coat and hang it by the AC vent to help it dry a bit. I took him up on his offer and as I handed it off I grazed the head of his cock through his pants. I went to the bathroom after he showed me where it was (though I could have gotten there with my eyes closed).
I cam back from the bathroom and he asked me about my job. Note- part of the success of a role play is in the story. Make something up so you are having fun and it adds an element of unknown to a situation. I made up a career in law. As the tender age of 30, I was a partner in one of the most successful environmental law firms in the U.S. I managed drilling rights and negotiations for oil strikes.
He became intrigued in my job and asked me to sit on the couch. He also asked if I wanted something to drink and I asked for a big glass of water. As he sat down aznd handed me the glass, I fumbled it on purpose and spilled it all over his tshirt and shorts, leaving him wet. He said it was okay and got up to chance and I stopped him. I told him I felt horrible but wanted to help him get out of those clothes. I stripped him down to his underwear right there in the living room.
The next three hours was filled with our own version of roleplay, mostly with my in my suit. The tie was handy for a restraint and, as an environmental lawyer, I got right down to drilling rights. This was one of the better times we ever had sex and one of the longest sessions. We fucked all over his house and I never broke character. Eventually the “tow truck” came and I went home, where he eventually drove over and begged for round 2 and 3.
Have also done coach/player (involving ripped speedos), teacher/student, and tailor/client. It’s all about the character and creativity.
very hot! and i just came from reading your role play experience, dewitt.
my favorite personal role play experience was harry potter themed. im a huge nerd and so was the guy i was hooking up with. i was a douchebag from slytherin house and my friend was in gryffindor. he was gloating about winning a game of quidditch and i was gonna teach him to shut his mouth. i used the petrificus charm on my dick to make it hard. we made references to wands. then i bully-fucked him and made him cry “gryffindor is a bunch of pussies!” we both also wore scarves the whole time. afterwards, i jokingly awarded 50 point to gryffindor house ~8)
That is the most amazing role play story I have EVER heard.
glad you enjoyed it 🙂 sad it wasnt you
I choose body form-displaying clothing. Once, the clerk attending me in mens wear stroked my ego, saying I had a nice round seat. He was a nice everything! Damn, I imagined he came into the fitting room FOR A VERY PERSONAL FITTING! Another scenario for role play? YES! Great improviser, no props or costumes needed!
I nominate you for an OSCAR! Fabulous role-play, unscripted! You’re HOT, man! Pardon me while I JO triggered by this scenario!