I've been meaning to write about this encounter for a while so apologies as i don't remember all the details. i don't remember how this dude and i connected - Manhunt, Adam4Adam, craigslist - who knows. Gay guy, never fucked a pussy before, really wants to hook up with a transguy, very cute. We had been corresponding for a while but unable to hook up due to both our living situations. we finally set a date. I head over one friday night, he lives in the gay section of town. he is also very discreet, won't exchange numbers only email.
get to his place, nice place, small, turns out he's a med student crashing with his brother who just happens to be out of town. he is as cute in person as his pics, skinny, tall white guy. we sit on his couch chatting for a bit. he admits he is very nervous.
he says i look kind of like demi moore in GI Jane. OK this is a bad sign and that comparison is far from reality.... however after saying that he leans over and kisses me. we start making out. its very hot. i'm horny.
i forgive him the demi moore comment. i can feel his hard on through his jeans. we take off our shirts and continue kissing and grinding. i unbutton his pants, pull out his cock and suck him off.
he says lets go to the bedroom so i follow him in. i suck him off some more. then i hand him a condom. he slips it on and pushes into me however soon after he goes soft. he pulls out and i suck him off some more however he is still soft. he apologizes says he's just so nervous.
so for the next seems like hour but i think it was more like half an hour he and i try to get him hard.
i'm patient but this is not fun and i'm starting to have feelings of insecurity i.e. is it me, type of feelings. at some point i'm thinking should i just leave. this is ridiculous. after what seems like forever he finally gets it up. he fucks me from behind - lasts about ten minutes... i get up, put my clothes back on and bid him good bye.
this perhaps was not a good use of my time