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How did you lose your virginity?

“Sleeping Over” with my “Friend”

Post by Anonymous on 20 March 2010

Okay. I’ve definitely had a lot of sexual experiences before then, but because I define intercourse as anal sex, I would say that the first time lost my virginity was around the time I turned 17.

See, I’ve always had a type A personality. I’m ambitious- I know what I want, and I do whatever it takes to get what I want. That paired with my skills in empathy, I was able to identify and manipulate most gay guys at school into the sack.

And let’s face it people, guys are easy. So for any straight guys reading this, I feel sorry for you. It is so unfair that you have been cursed with your straightness, that you have to spend so much time, money and effort on the fairer sex when you could be having casual sex 3+ times a day like us gay guys. And that you are prone to the most expensive STD known to man… the girlfriend pregnancy, which leads to the ‘child’, which leads to the ‘child support check’.

Anyway, now that I’m done tangenting- back to my first time. Ah yes, my first fuckbuddy (who is now, my sort-of boyfriend after a few guys in between). We were in highschool and all it took was for me to catch him staring to tell that he was probably undressing me with his eyes, like I had done so many times to him (along with every other guy) in gym class.

We soon became good “friends” that had regular “sleepovers”. Note the use of quotation marks. Parents- if your boys are having sleepovers when they’re above 16, they’re probably not actually sleeping, they’re probably having races to see who cums first and using playstation sounds to mask the sound of their fapping.

Anyway, we had only done things like mutual masturbation and the wonderful, underrated non-penetrative intercrural sex because usually all it took was like 5 seconds before he came. Which was alright with me, but one day we took it further.

That night his parents just left to go do whatever it is annoying cockblocking parents do when they go out for the night, eating up the lie about us not needing a movie because we were just going to play playstation all night.

We heard the car leave and I went to work. I knew that to get him to last longer in the sack, I needed to bring him into maybe the third or fourth round. Having read extensive online texts on how to give a guy extreme pleasure orally (and having experience in place from just having a cock), I felt I was ready… Too bad he wasn’t. I pulled down his pants, put his piece in my mouth and used my tongue to apply pressure in just the right place while he throbbed in my mouth and prematurely ejaculated everywhere within seconds.

He lasted much longer in round 2. He seemed more comfortable too, and wanted to experiment with different things. He gave me a blowjob but I stopped him when I started convulsing (not wanting to cum just yet), and to my surprise, I let him top me. AND to my even bigger surprise, I let him top me WITHOUT protection (Stupid! Stupid! Stupid!)

Receiving his banana was… okay to be truthful it was painful. I had not researched anal sex and neither of us knew what we were doing. So I just told him to keep going. Instead of taking it slow like we should have, he pounded me like crazy, like the tacky porn-stars we watched in our hidden stash. Except I’m pretty sure he went harder than that. He’s a muscular athletic islander guy, and I’m just a fragile little thing. And his cock curves slightly, so he must have friggin ripped some wall in there because I was sore for a few days after.

I tried topping later that night, and I hated it. So the whole anal thing just didn’t work out for me.

(He doesn’t know this part)... Early in the morning the next day I went home and sat in the shower and just wept. It wasn’t the pain, it was the fact that I was so stupid by letting him fuck me without a condom. It’s one of the most horrible feelings in the world, not knowing. I was in control, like always, but somehow that one moment was all that mattered to me at the time, and I didn’t think about protecting my future.

I went to get myself tested about a year later. You want to know the results?... Can you guess?... HIV NEGATIVE YEAHYAHHHHHH!!! (You thought I was going to say positive huh?). I felt like I was given a new lease on life, and the scare forced me into ALWAYS playing it safe and fuck or be fucked with caps on!

The moral? Always use a condom. For your peace of mind, and for your and your partner’s health. Moral number 2? Anal is so overrated. We stick to blowjobs and intercrural sex now. Sometimes though, he pesters me to bottom, which I only do on Saturdays because I don’t have to limp around as much on Sundays.