I don't know exactly when I became obsessed with fucking women in the ass, or how it happened, but I‘m an ass freak and I‘m proud of it. The attraction probably started from watching porn or surfing the Net too much with my dick in my hand, but ever since I stuffed my cock into a chick's tight asshole for the first time, pussy has been my second choice. Nothing tops a hard assfuck in my book. On top of being tighter and hotter, it also has a unique appeal as the most intimate sex act a man and a woman can perform.
My first was Ariel, a girl I dated in college. She’d tried anal once before with another guy and didn't like it, but after watching a porn together and seeing two chicks get their asses reamed by a guy with a huge cock, she asked if I wanted to try it and the rest is history. It took us forever to get her to relax her sphincter enough to get my cock inside, but I was hard the whole time in anticipation. When I finally got the whole thing in, it was one of the most amazing sensations I've ever felt.
Her ass was supremely tight and the feel of her body and the expression on her face was unforgettable. It was like she was concentrating as hard as she could to please me, and accepting the trust she'd placed in me not to hurt her made me feel very special. It was an awesome experience all around. She loved it, especially when I reached around and played with her clit at the same time, and for the three months that we dated I fucked her in the ass about every other time we made love.
That was actually a long time ago. I've had lots of girlfriends since then, but I haven't dated any who loved it in the ass as much as Ariel. I learned to curb my desires and settled for vanilla sex until about three months ago when I discovered online dating.
I realized I could find babes who were into anal sex right from the start and my life hasn't been the same. It's how I found Caroline and she's everything I ever dreamed of. On top of having an incredible body, she's so into anal she begs me for it and I can fuck her ass as hard as I want. It's like she has two pussies. The only downside is that she's married, but I'm still only 22. I'm not looking for a wife, fucking around is just fine by me.
We have a routine going that works perfect. I go to college and I have a spare early in the afternoon three times a week. It never fails. Every spare I'm over at her house stretching her ass to new limits and coming on her face.
She was a little shy at first online, especially getting her to talk about anal sex, but once she came around it was like we'd been lovers for years. She's introduced me to her collection of love toys and I've helped her use at least two dozen already. I think I've done enough experimenting now to know that I like sex without toys the best, but I'm not about to make a big fuss over shoving a vibrator in her ass while I fuck her pussy. I'm just happy to be with her for a wild ride.
Once I got the chance to fuck a chick like Caroline I broke up with my current girlfriend. She was squeamish about anything going near her ass and even though I really wanted to take her anal virginity, the time and energy I‘d have to spend to convince her to do it just didn‘t seem worth it. Not when there are thousands to choose from online who’ll take it up the ass on a first date.
Dumping my steady girlfriend did create one problem though: getting laid three times a week isn't enough. It's a good thing a one night stand is easier to find online than a girlfriend. I'm not sure if anyone would believe me if I gave detailed descriptions of the sex I've had with women who only wanted one night stands, but believe me, there are some seriously kinky babes out there. Some of them have been even too kinky for me to handle, but in each case let’s just say I did my best. I'll save those stories for another time though, after I see how well this story is received.
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