A few weeks ago I got this message on one of my sites:
“Officially straight, but had a couple of discreet bi meets, and after more. Ideally with a younger guy. Available most mornings, but cannot accommodate. Have a thing for crossdress if that interests you at all? Be great to hear back if interested, and we can message and exchange pics first.”
Repeating my mantra of “I’ll try anything once…”, I got back in touch and told him I was available some mornings depending on Uni, that I can accommodate, and that I was happy to dress up for him as long as he provided the clothes. Photos were exchanged and eventually, when conflicting work and study schedules were resolved, he came to mine last Tuesday for some fun.
I was pleasantly surprised when I opened the door; he was actually really good looking in person and his body was more toned (not that he was topless on the doorstep, you understand, the neighbours wouldn’t approve). I let him and and showed him to the bedroom, while I went into the bathroom to change into the clothes he handed me when he arrived. Fully kitted out in tights, a black and pink bra and a vest top (which actually all fit really well), I went into my room to find him naked on my bed, and as we’d described in our email exchanges, I set to work sucking him off straight away.
He came after less than three minutes, like he thought he would, so while he was recharging he reached down into his bag and pulled out – not a sex toy, as I was expecting – a carrot. I shit you not, a carrot. “Work kept me really busy, so I couldn’t get everything I wanted…”
But, in for a penny, in for a pound(ing), I lay back and relaxed as he put a condom on it and lubed me up and in it went.
Carrots… they’re not as smooth as you might think. This one was fairly straight as far as carrots go (I’ve taken to evaluating the shapes of them whenever I’m in the supermarket now and thinking thank Christ it wasn’t that one) but still,their surface is quite rough and even through the condom I could feel that. After a few minutes he pulled it out and I expected him to fuck me, but no, he couldn’t get it up, so I decided to give him a helping hand (read: helping mouth). He still didn’t get hard for ages, and then when he did it was only to cum (again) and then he got soft again. Very disappointing.
So to cut a long story short, I more or less just finished myself off and kicked him out. I couldn’t help but think, maybe you are just straight after all – so why bother finding a guy who’s going to dress up for you? Still, it was an experience and I don’t know that I would be very resistant to crossdressing again (There’s a seemingly endless subculture of self-described “traps” and/or “fembois” on Tumblr and a lot of them aren’t bad looking at all, at least in my view!). Who knows?