a little background; i'm 31. i was never popular with the ladies, even when my house was used as a party house where plenty of teen sex was happening, but i was never involved. nonetheless, i have had a few relationships, and a few chance one-night-stands.
the latest time (after 2.5 years of "celibacy"); was after chatting with a girl 10 years younger on a website. we went from web-chatting to text chatting, then met up. we went out to a billiards hall, where i "let" her win. then she drove me home (i don't have a license or car at the moment). the next day she picked me up after she got out of school and we went to eat, then came to my place and had sex.
the only real problem was that i wasn't able to maintain an erection. i had one during foreplay, but when it came time to put the condom on, he took a nose dive. she sucked it to get it going, i put on the condom, and went long enough for her to (fake?) orgasm, and i pulled out and said "this isn't working" to which she replies, "well i'm not on the pill so you can't do it without it." at which point i had to reassure her it wasn't her, it was me. and we cuddled. then she left, and we shared a total of 4 text messages since.
not that i really want to be with her again, i really want to redeem myself, and use a more comfortable condom or something... should i just leave her alone and more on to the next?
i could include more details, i just didn't want to make the post too long.