Soo I was 24 last year when I did this… still my only crossdressing experience pleasing another man.
My girlfriend was out for the night having drinks with friends, so I took the opportunity to get dressed up in her black lace bodysuit, and put on some red lipstick, mascara, and blush with glittery eyeshadow. I loved the risk because I didn’t know when she’d be coming back.
Anyway, I’m watching sissy hypnos and edging whilst talking dirty to guys on grindr and kik which I usually do secretly when I’m really feeling like a sissy. One guy pops up with a cock pic demanding a facepic from me. Now I never usually do this due to risk but because I was so fucking horny I sent him some pics pouting and winking and stuff.
He messages back saying I’m sexy and he wants to come through to me, he’s a half hour drive away. I bite my lip while I’m playing with my clitty and say OK.
He dawdled and actually took an hour to come through, which got me so fuckin nervous my gf would walk in. I left the door unlocked and sat in my front room, heart beating out of my chest. I text him saying to just let himself in and lock the door behind him.