Kinky · Men and Sex · Sex positivity · Stories (Vicky) · Vicky

How To Have Anal Sex For The First Time

Bacchus from was talking about anal first-time and it got me to thinking about my own sort-of first time, only time, really.

This entry could be subtitled “Why you should not have hot completely drunk monkey sex with a bad back”.

About that bad back. Most of the time it’s OK. But I’m careful. I know what I can and cannot do with it. I can do many *wiggles eyebrows* things. I cannot, say, lift a computer monitor. But all this knowledge can go out the window if I’m not careful.

I am not careful when I am drunk.

And I was very drunk. It was one of the few times in my life when I actually acted like a Complete Slut (and yes, believe me, it deserves the capitals).


I was at my best friend’s housewarming party and there weren’t too many people there, so we drank all the more to make up for it–I think we started in about 3:00 in the afternoon. Those of you who know me also know that I can sock away about three or four drinks before being completely drunk; it only takes half that to make me so flirty and horny that I might just follow you home if you ask.

I hadn’t had three or four by late evening; it was more like six or seven, probably. Almost nothing for some, but I was pretty well looped.

And there was a guy.

You knew there would be. I’d been looking at him out of the corner of my eye most of the day, too shy to actually go up to him and say hi, much less flirt. But oh yummy goodness. Kind of bad-boy like, looking a lot like Luke Perry from 90210. Mmm. He didn’t seem to notice me much either, my wonderfully too-short denim skirt seeming to have no effect whatsoever.

I was sitting and pleasantly spinning in a deck chair in the dark, chatting with a friend, when one of my girlfriends came up behind me and started rubbing my shoulders. I am noisy about this at my most sober, so you can imagine the moans coming from me at this point. Well, turns out it drove Bad Boy insane. His eyes lit with that thing that’s even darker than lust; it’s about fucking, pure and simple. I’ve only seen it a few times in a man’s eyes, but enough to recognize the signs.

What did I do? I moaned a little louder, of course, crossing my legs so my nice bare thighs rubbed against one another.

Before I knew it, he was telling the whole group what a sexy moan I had, and that he had to hear it closer, and came behind me, and took over rubbing my shoulders. I moaned louder, pressing back against him in a way that left no doubt that I was hot and ready for it.

So anyway at some point we end up in the room where I’m staying overnight.

We get naked in the middle of kissing and groping. Honestly, I don’t remember much of it; I was that drunk. Should have known better, but didn’t. Rolled the condom down and then he was inside me, every position possible. At one point my ankles are wrapped behind his neck and he’s pushing into me and I’m moaning, near passing out, and his cock slips from one hole into the other and he’s moaning about how tight I am, and I’m so numb I couldn’t have felt it anyway.

I push closer.


That’s when I felt my back go out.

Correct. I was so drunk I couldn’t feel anything but the pressure of his cock in my virgin ass, but believe me, I felt my back go. We disengaged and somehow I got pillows under my knees before passing out on the bed.

I woke up with the world on fire and so sick from drink I wished I was dead. I didn’t even wake him to get his number. I stumbled downstairs, called a cab. It was almost a week before my back healed.

So, yes, I’ve sort of tried anal sex, and yes, it did hurt, but not where you think. 🙂

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