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Butt-Fucking Cindy

I met a girl soon after my break up with Cindy. Coincidentally, this new girl was Cindy also. She was a very petite person, with blond, Nordic looks, and curly hair. She kind of looks like Meg Ryan probably did around age nineteen.

Cindy was very interested in music, and played piano very well. I too, am a music student at the university, so we hit it right off with our mutual musical interest. Only thing is she’s more about classical, and I’m a roadhouse boogie kind of guy. But still…

We had sex, if you want to call it that, on our very first date. She told me she was on the pill, but it made her constipated. Actually, I think a diet of coffee and pastries was more to blame. Anyway, I said, “I know a cure for that.”

She was all ears. I told her straight out that anal fingering seems to help with constipation. I have no idea whether that’s true, but that’s what came to my mind. At that point, I knew I’d either get slapped, or laid. I’ve learned to speak the truth, and directly in such matters, and as usual, it paid off this time.

We played some strip poker. I was naked first. I couldn’t hide my erection, even though it kind of embarrassed me. It’s kind of like showing your hand in cards. When a guy is erect in front of a girl, it’s pretty obvious he’s attracted to her. But then again, I did find her exceptionally attractive. Why hide it, right? I just happen to like skinny, light-skinned girls. Her breasts could have been bigger, but who’s complaining?

I sat my bed, and had her lay face down across my lap, with one leg dangling over the edge of the mattress, exposing her small, puckered pink asshole very nicely. I was already in heaven, because I love seeing female anuses. Now, I know that male anuses are pretty much the same thing, yet they don’t attract me at all. Go figure! Then, I caught a whiff of her sweet girl anal gland smell, and I swear, I could have orgasmed right then and there if I had let myself.

Knowing what little I do know about sex, and even though this was the first time I’d have an opportunity to finger a girl’s ass, I knew to proceed slowly. Very slowly. For a good two minutes, all I did was swirl my finger around her anus, staying a half-inch away from the opening itself.

She was already going “Ummm,” and “Oooh,” letting me know I was on the right track, and she was fully on board.



In time, I pushed very gently against her anus itself. I somehow thought I’d have easy entry, but she let me know some sort of lubricant would be required. I started to get up to see what I could find in the kitchen, but she stopped me, saying only, “Here.”

With that, she pushed her fingers over my legs and under her stomach, reached into her vaginal slit, then reach out and around, spreading her natural girl lubricant on her own anus. She reached under again, then put some on my index finger.

I ever so slowly pushed my now lubricated finger into her anus. It was much smaller and tighter than I had imagined. I mean, I’ve seen many pretty anuses on the Internet – what guy hasn’t? But I didn’t realize how tight they are.

I fingered her for a good couple of minutes when she started shaking. I mean, like totally shivering. I stopped, and started to pull out.

“No, stay, It’s wonderful.”

I continued fingering her, and her very quiet moans turned practically into shrieks. I was worried that my roommates might hear, but also, dare I say, rather proud. I kind of wanted them to hear me being all sexual with this beautiful girl.

The shivering got really strong. Then she orgasmed. I never realized that you could feel a girl’s anus contracting in orgasm around your finger. (Later I found out that this doesn’t always happen to the degree where you can feel your finger being compressed.)

I let her settle down for a while figuring that was probably it. That was most likely all the sex we’d have, but of course realizing we’d be doing more things in the future. I was mildly disappointed however. I would have liked to have an orgasm with her. Very much so!

She totally surprised me by asking whether I thought I could get two fingers in. Of course I was all for that, and in a few minutes, did in fact manage to get two well-girl-lubricated fingers into her anus. She didn’t orgasm again, however.

Then, she floored me entirely: “Do you think you could get your penis in there?”

She didn’t have to ask twice. It took some doing. It seemed like it wasn’t going to fit, and I didn’t want to hurt her. I asked several times, and she insisted it didn’t hurt at all, even though I felt her muscles tense quite a bit a couple of times.

Finally I was fully embedded in her rear end. It wasn’t lost on me that with my cock stuck fully into her asshole, I was laying with my full weight, my chest against her back, and it was simply a delicious feeling hugging her like that.

I’d like to say we fucked and fucked, but unfortunately, I came almost right away. As I was just calming down, she orgasmed again. I didn’t feel her contractions against my penis on that occasion, but have noticed that sensation since.

Because, here’s the weird part. I have yet to fuck that girl. I mean, Cindy is so in love with anal intercourse, that we have not yet had regular vaginal intercourse. It’s fine with me!

And, it gets weirder – maybe. I’ve met her brother. He too, is light-skinned Nordic. He’s tall, and and I have to say, a very good-looking dude. Both Cindy and he have asked me whether I might like butt-fucking him. She would really like to watch that. I’m not entirely opposed to the idea.

One thought on “Butt-Fucking Cindy”

  1. I too have a similar situation except my girl is a virgin. 4 years now and I still haven’t broken that barrier. But it’s because I get all the ass I want.

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