How to Roleplay During Sex

The TMI Tuesday topic a couple of weeks back was about the use of roleplaying during sex. SilverHubby and I were dismayed at the number of people who said something like ‘I’ve never roleplayed during sex’ or ‘I wouldn’t know how’.

So I figured it was time to write a How To guide, using a session from last week as an example.

The fantasy: I am a hot young male university student and SilverHubby is my sexy older male professor.

The reality: We’re middle aged, married, and one of us is female. 

To help keep everything straight, whatever is part of the fantasy will be blue, and whatever is happening in reality is grey.

The scene begins:

Professor? May I come in?” I ask.

“You’re late, boy.” he says sternly.

I shuffle my feet and lower my eyes. “I was in the locker room with the football team.”

“Have you been naughty, boy?”

“Yes, Sir.”

“You’re going to have to be punished for being such a slut, you know.”

“Yes, Sir, I know.” I start to bend over in front of my professor.

“Oh no, boy. I’ve thought of something better. I’m going to punish you today by NOT fucking your ass. Instead, you’re going to fuck mine.”

“Please professor? Please put your cock inside me.”

“No, boy. You haven’t earned it. You’re going to have to use my ass in just the way I like. Now go and get ready.”

Reality intervenes, and I get the strapless strap inserted, then try to put on the RodeoH harness to help hold it in place. “Um, SilverHubby? This isn’t working. Can you bring the leather strap-on?”

“Where is it?”

“In the dressing table, the door on the left, on the upper shelf.”

“I can’t find it.”

I waddle in, trying to keep the dildo in place inside me. After digging around on the shelf for a moment, I find it. “Oh, I forgot I’d put it inside a Lovehoney bag.”

“What do you need me to do?”

“I’m going to step into it and put the dildo through the O-ring, then I need you to buckle it and adjust the leg straps. Pull them together, g-string style. I think that might help hold it in better.”

“You realize I already put two syringes full of silicone lube in my ass, and I’m having trouble keeping it in.”

After much fumbling around, we get back into bed together. I lube up the dildo and get into spoon position behind him.

More “in character” talk occurs, which was almost certainly sexier to experience than to read, so I’ll spare you. I get my “cock” ready to enter his ass and…

“You’re a little too high”

“Is that better?”

“I think so. No, wait, stop.”


“I think that’s far enough for now.”

“Alright. I’ll stay still, and you can push back when you’re ready.”

More fantasy talk, and our sex progresses, with me getting a little bit further inside. Then…

“You just fell out.”

“Oh hell, did I? Let me just…”

“Hold on, I think the dildo needs more lube.”

“Okay….. is that better?”

“Can you try moving your body more this way?”

“I can’t. The dildo doesn’t have any flexibility. It’s this position or nothing.”

“Okay, then… CRAP! It fell out again!”

“Fuck. This isn’t working is it?” I get out of bed, remove the harness and dildo, and replace it with the RodeoH harness and O2 Mark Dildo. “How about this?”

“Oooh, yes. You feel so good inside me, boy.” And so on…

And yes, that really is all there is to it. Just pretend and dirty talk. Despite all of the miscues in the above scene, we still had really hot sex that night. When things go wrong just roll with it. Choose a different position, a different toy. Heck, change the fantasy completely. Maybe what started as a gay professor / student fantasy turns into a naughty French maid offering extra services to the rich businessman staying at the hotel.

Yes, you will feel silly. That’s normal. Do it anyway.

It’s definitely worth it.

Something for the weekend

This entry was posted in Anal, Archive, Dildos, Gender Play, Pegging, Sex Talk on by .

About silverdrop

Silverdrop and SilverHubby are a middle aged married opposite-sex couple living in the UK. Silverdrop is gender-queer and SilverHubby is pansexual. We use this blog to talk about our sex lives (especially our fanaticism about anal and pegging), share erotic photos, and offer sex toy reviews. Our [sex isn't always great], mostly because of our health problems, but we always write honestly about it. Our kinks include BDSM, gender-play, pegging, roleplay, fantasy, and lots and lots of anal.

One thought on “How to Roleplay During Sex

Comments are closed.