Normally Valentines day is just a big reminder that I'm single. Not really an issue since really, I've tried the whole relationship thing on more that one occasion and I'm kinda terrible at it. But this day also serves as another kind of reminder for me, something that is a lot more fun to think about than me sucking relationships, the day I lost my dreaded V-card.
Since the incident at Cody Vegas me and Britney had developed a kind of friends with benefits type situation. That went on mostly fine for a few months until I managed to screw things up on a epic scale when I started to have a thing with her OTHER best friend. That started a whole shit storm of female drama and now those 2 girls that were once inseparable before me no longer speak. I was able to eventually patch things up with Britney's friend first and then later on with Britney (how I manged this while they still hate each other, not sure) but eventually me and Britney just sort of naturally fell into our old habits of her coming to my apartment and giving me head.
We never got past oral because as I had alluded to in the "Coming of Age Story: Part Two" the prospect of sex more or less terrified me since well...I was scared of the vag. I can't really explain it, maybe it was because I was exposed to hardcore porn at way too young of an age and seeing some girl spread eagle spreading something open that I have never seen before traumatized me on some kind of level. While others looked at the vajay-jay with yearning, all I saw was the sarlac pit monster from Return of The Jedi. It took one of my ex's more or less forcing me into a situation where I'd have to touch it and lick it for me to ever do it. Even while it wasn't anywhere near as bad as I had thought it would be, it still made me gag slightly and I couldn't get over the weirdness of how the vag felt on the inside. Seriously it was like some kind of jelly cave.
Anyways so Britney is over and we are fooling around and I'm getting ready to get my pants off so i can get my BJ and just be a happy dude but that wasn't in the cards tonight. While I was gettin into the motions Britney mentioned about how dry her mouth was. Sure kind of an obvious sign, but I was in full on horny mode and all I knew was that something was going to be happening down in my pants soon.
I kept trying but she remained insistent that nothing was going into her mouth tonight. So there I was with a full on boner in "I need to get off" mode and my only outlet was closed for shop. Could of tried for a handjob but really no girl knows how to jerk off a guy properly. Since puberty I've been doing it like 3+ times a day, she just can't beat that kind of experience. So no mouth, her hands were just not interested and that left me with one option. I was a lot more resistant to the idea of actually having sex then I'd like to admit. I mean really if the younger me knew that I could have gotten laid months ago if I had just took off her pants, he would probably kick me in the balls. But still it just seemed like a huge step and really I was pretty clueless as to what to do. I mean yeah I have seen plenty of the X-rated movies in my day but there's a huge difference between seeing and doing. But really, the second she decided that I wasn't going to be getting head that night my fate was sealed, I couldn't in good conscious just say 'well I guess we aren't doing anything tonight" plus really she had been gettin by on just fooling around blowing me for months. I owed her, honestly don't know how I got away with some of the shit I got away with, with that girl.
So got the condom out, put it on and was all set to do it. Right off the bat though ran into the issue. I mean, I know my female anatomy but I still had quite the issue of gettin it in. Eventually she just had to do it for me. The sensation was....good. Can definitely see why I've been craving this for so long despite my weird vaginal phobias. But still there were some kinks. For one thing for every like 5 thrusts, i would get over eager and pull back to far and it would pop out, which would start over the whole "where the fuck did it go" search. Really the whole thing quickly just became more frustrating then fun so I kinda just....pulled out, rolled over and went to bed without either of us finishing.
Yeah, real great thing to do I know but it was just pissing me off and I was sick of it. Though I will say though my 1st time was anything but a success, got to try again with her soon after and at least I was able to finish...like 2 minutes later. It went like that for a few more times until it all just sorta clicked and was able to last long enough to watch an episode of Nip/Tuck or two while we were going at it, and both of us were able to get off, her a lot more times than me.
But yeah, that's how I lost my virginity which somehow ended up on valentines day. Though technically we started going at it around like 11:50 something at night on the 13th....but February 13th is my mom's birthday so i'll much rather say I lost my virginity on valentines day than on my mom's birthday.