Role play experiences?

Question

I’m a guy and my girl wants to make me cross dress, paint my nails, and peg me. I’ve never tried this stuff before and am unsure about how it will go. Do you guys have any experiences with this?

Leapfrog00 · Accepted Answer

My ex-girlfriend was super into role-playing. We used to play dress up all the time and pegging was rather fun. It felt different. If you've never done it before, you'll probably feel uncomfortable at first. It takes getting used to, but after that, no problem.

There's a G-spot in your rectum, so the orgasms are a lot more intense. Cross-dressing is no big deal. It's about feeling comfortable with yourself. My ex used to put me in her skirts and nylons, and I'd play her, she'd be me, it was wild! I loved it!

It makes the sex a lot better, for sure! It might feel weird at first because girls' clothing feels so much more different than guys' clothing, but that's the fun in it. Trying new things. Just relax and enjoy it!

Jocktober · Accepted Answer

Well, I don't know anything about girls and strapons or makeup. But I know the rest. I second the buttplug. At least use a finger or something, stretch yourself out as best you can. Even if you get to start with a small strapon, you're so not ready for it. I went straight to a huge cock and it was horrible the first several times. Clothes are just clothes. I've dressed up in girls underwear and a schoolgirl skirt for a man more than once. It shouldn't matter, it's just wearing something different, all very superficial.

BrookeAZ90 · Accepted Answer

I peg my boyfriend pretty regularly. It's not exactly roleplay, just a different activity to mix things up a bit. I didn't go straight to the dressing up for it though. I waited years before I brought that up. If either makes you uncomfortable, you might want to say that now. I don't know about the makeup. I'd have no interest in that really. But yes, as said below, spend a week or two preparing yourself to fit something that big in it. I think as much as many guys don't want to admit it, the science behind nerve endings in your prostate is pretty inarguable. You'll love it.

Berethor · Answer

Sounds gay, if a girl wants me to take part in crap like that I would tell to go fuck herself.

BradBoy · Answer

Not sure I'd call any of it roleplay but I've played dress up, though it was for an older man when I was younger. My girlfriend pegs me occasionally, but not with the dressing up or makeup or anything. You definitely want a butt plug to get yourself ready for that. It feels awesome to take it in the back, but it'll be painful if you're not ready.