true story: anal sex?


Bacchus was talking about anal first-times (bad one mentioned here) 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. 🙂

About the author

Vikki McKay


  • [laughs] That’s the funniest part, that the anal sex part didn’t hurt at all. Ah, well. I learned a valuable lesson. And the encounter was sufficiently fuzzy that I can still enjoy another “first” time, at some point in the future. 🙂

  • That reminds me about my first , and only, anal sex experience. But I was so drunk that I can’t remember anything… My girlfriend wasn’t so drunk as i was, so she said it was nice… I can’t remember anything. I think I just have to belive in what she said. Maybe it was nice…

  • My boyfriend is crazy for anal, but I am like um. isn’t it un-hygenic ? What if your colon is not completely emptied.
    sorry but this thought’s been haunting me and I CAN NOT anal..because of this fear.

  • WOW !! your story really is funny ( my boyfriend told me about it a while ago ) …
    Today was my first ANAL experience and I can say it wasn’t as hard as I tought.
    I was so, so , so horny that when he asked me in the middle of the foreplay I acepted. This time I didn’t chickend out as usualy …
    I’m looking forward the next round. …

  • My girlfriend has an ass shaped like an onion and it sits on her back,but to make it better she’s slim with a 20 pound ass. But for some strange reason after I first had anal sex with her I became totally addicted to her ass. I mean that’s all I want from her now is my dick in that juicy tight ass. And I can’t stop calling her every 10 minutes now either. I think anal sex with the right girl can turn you out because before that expirence I was just fucking her pussy and that didn’t make me act the way I am now. And on top of that I had anal sex with previous women but it didn’t have this type of affect. Anal sex with bubble butt girls is addictive, trust me.

  • The bit about your back made me wince in synpathy – been there and it’s AGONISING! Not fun at all.
    Sorry you were too numb to enjoy the anal bit. Done sweetly between lovers it can be sooo intense. And then there’s the intriguing question about what to do with your unoccupied pussy while you’re already flying……..

  • I had my first anal experience when I was 22 years old, while on a bus tour of Europe. I met a 19-year-old hunk on the tour, and by the time we got to Rome, he and I were drinking buddies. That night, I surrendered my body to him for his pleasure. A few nights later, we arrived in London, and I knew that the tour had come to an end and that I might never see him again. So I visited him in his hotel room for one last encounter. His room was equipped with several shampoo bottles and he took one of them and invited me to take off my clothes. When ready, I positioned myself nude on his bed, and he opened the bottle and poured shampoo onto my pubic hair and pussy, using his hands to lather it up in the crotch area between my thighs. Then, he undressed, and I thought he was going to fuck my pussy. But he lifted my ankles up high and positioned his cock against my shampoo-lathered anus. Without warning, he suddenly shoved his entire erect cock into my asshole, slicing through my sphincter muscle and ripping through my rectum. I buried my face into the pillow to muffle a cry of incredible agony. He sensed my discomfort and asked, “Does it hurt?” And I lifted my head and whispered back, “Yes.” So he asked, “Do you want me to stop?” And I whispered, “No, I don’t care how much it hurts…I want you to enjoy me for your pleasure…don’t hold back…please fuck my ass.” And that he did. He proceeded to pump his cock back and forth inside my anal chute, as I continued to writhe in pain while stifling my moans by biting my own forearm. It was painful, but very intense, and I found myself turned on by merely THINKING of the fact that I had just given him permission to fuck my asshole as hard as he wanted, and he was DOING IT. I let myself go, and after about 10 minutes of his thrusting, my pain subsided enough that I was able to focus on his breathing and his pleasure with every stroke. Another 10 minutes or so, and he finally came deep inside my ass while biting down hard on my left nipple. I never saw him again, although we did correspond by mail for more than six months. And to this day, I have never experienced more pain, intensity, and pleasure as I did on that night in London.

  • I had an awesome butt fuck the other night. Im a transvestite and so was she. Ive had anal sex with rather small girls and it felt more like a large finger. But this girl was at least 8 inches long and very wide.
    Anyway, we were just messing around when her finger brushed against my ass, She saw me gasp a little bit and went in for the kill. She prodded my bum with her finger. I let her do that and I kept getting hornier. She just didnt slide in, she sort of pumped her fingers every time I was coming down from the shock of them going in. It was like walking a tight rope.
    Eventually she said,well, I got two in pretty good, I think I can slip a cock in. I was scared, she was big,and i wanted her.
    She pushed in, and I beared down on her. Her head popped in and it hurt. I said slow, and then I ground down on it. It hurt again, but I again ground on it. Eventually, it was all the way in. God, I felt full. After feeling full for a min, she started to pump against me. God, I just lifted my ass higher and let her pump. I could have gone on all night. I asked her to pull out about 2/3rds and slide back in. I nearly passed out in extacy, I felt like a greedy person getting slammed with all that pleasure. Well, needless to say, when you submit to a good fucker, it is absolutely wonderful.

  • my anal sex is very much painful, i think i can’t explain what i feel’ but this become my hobbit. honestly i like guys fucking my back….:)

  • When I was a junior in college, my boyfriend invited me to his dorm room one night while his roommate was out of town on vacation. One thing led to another thanks to the use of Hershey’s Kisses and a bottle of rum. I took off my shirt and bra, and he took off my pants and panties. As I lay nude on his bed, he slowly inserted Hershey’s Kisses one at a time into my asshole, filling my ass with 20 of them. Then, he placed his nine-inch cock against my anus and spent the next 90 minutes reaming out my asshole with it. I found anal sex to be very intense and pleasurable, despite the extreme pain of the initial 10 minutes of penetration. I came twice, and he came four times before I sucked him off a fifth time.

  • texas hold’em

    The human mind evolved to believe in the gods. It did not evolve to believe in biology. Acceptance of the supernatural conveyed a great advantage throughout prehistory, when the brain was evolving. Th

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