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(This a true story. Both of us were of legal age, consenting, and enjoyed ourselves very much.)
I don't know who can relate, but probably every young guy ends up begging their first pretty serious long-term girlfriend to let them try it out. "Please, baby. Can I try putting it in your ass? Just the tip? What about for Christmas or my birthday or something?" I was no different.
Except that, for all the freaky things that girlfriend was willing to do (she's the girl from the cult story), anal was a hard no. I probably asked her about it a handful of times, definitely begged once, in the first year we dated, but, after she kept flatly rejecting the idea, gave up.
I ultimately ended up thinking about it a little further and chalked it up to the fact that she was very petite and that my cock is not small. So, just from a size-of-things perspective, it was probably a bad idea. And, just speaking as a man, I had to learn that I can't have everything I want and that I should have respected her wishes instead of pestering her. It seems silly to think that lusting for her asshole caused such introspection, but it's true.
Anyway, I hadn't even thought about trying anal with her for some time when my 21st Birthday came up. I was at college at the time, and despite having plenty of friends and going to a party school, I didn't have much planned. I told her that I wanted to keep it low-key, maybe just spend the evening with her. Her face lit up when I said that. This was over ten years ago, and I still remember how big her smile was. I told her that a couple days before my birthday, and I also remember when her look turned devious and she told me, "You won't regret this."
I had an evening class that ended at 9pm on the night of my birthday, and let my girlfriend into my dorm room. I'd had my dorm, a double, to myself since my roommate dropped out halfway through fall semester. All the while when I was in class, my phone would buzz in my pocket with a new nude, a new pic of her in lingerie, or a nasty message like, "I want your tongue on every part of me." It was a Thursday night, but she'd brought enough lingerie to peel off something new for breakfast, lunch, and dinner - even if what I was eating was the same thing each time.
When class ended, I was practically sprinting back to my room - my mind completely erased of any thoughts besides how good my cock was going to feel throbbing inside her and "I want your tongue on every part of me," and how this was going to be the best birthday ever. How little I knew...
I knocked on my dorm door, like she'd asked me to, and she answered. She was wearing a faux-leather garter and matching "bra" that was basically straps connected to a metal ring that circled her nipples and no panties. I was dumb-founded and stupid horny. She just stood there with the door wide open. Anyone walking by could see. Hell, they would see; how could they not?
She beckoned me in. She backed slowly to the spare bed - I assume now that she thought there would be a mess. She undressed me, slowly, one piece of clothing at a time. She made me stand there, by the bed, naked, and as fucking hard as my cock could be.
I don't remember what she said exactly. But I remember her sitting down on the bed, looking at herself in the mirror mounted to the bathroom door, and then looking back up at me with the sluttiest fuck-me eyes I have ever seen. I'm going to do my best to paraphrase what I remember.
She laid back on the bed, holding eye contact. "I told you this would be special."
She ran her fingers over her thighs, along the garter. "That we could do something you've always wanted to do."
She turned over, and pushed her ass up in the air. "I'm going to let you fuck me in the ass."
She laid back down and squeezed her ass cheeks. "Before you do though..."
She spread them apart, opening her asshole slightly, "You can't stick your cock in there unless your tongue has gone in first."
We'd been dating over a year at that point, and her asshole was taboo as taboo could be. No fingers, no toys, and definitely no cock. Now, she wants my tongue in her ass? The blossoming hedonist in me didn't know what to think and, honestly, hadn't even fucking thought of that as an option in the first place. For my generation, I was extremely late to the ass-eating game.
I didn't hesitate. The next thing I can remember, my face was buried in her ass like I was trying to get my tongue, lips, whole damn head inside there. I probably ate her ass more intensely than I'd ever eaten her pussy before. I could feel my cock throbbing.
Then I heard her moaning. It wasn't just like she was enjoying it, but moreso like she was surprised at how much she enjoyed it. It was like she was discovering a kink she didn't know she had (spoiler: that's exactly what happened).
My cock kept bumping up against her calves and thighs. I must have been involuntarily humping her legs as I sloppily toungued her asshole. I got so wildly carried away that I ended up on the bed with my cock pointing to her face while I kept eating her ass. She tried to suck my cock while I did, but the angle just wasn't right. She ended up stroking it instead.
And stroking it was a terrible idea. I came. Very fucking hard. It shot all over her shoulder, upper back, it hit me in my chest, and in the stupid fucking goatee-thing I had. It felt like my balls imploded. All she could say was, "Holy fuck!"
We did end up fucking again later that night. She never took off the lingerie. But, she ended up requesting that I eat her ass again. I did, just not as voraciously. The sex was fairly normal for us. She was bent over the edge of the bed, we had the blinds open for the campus to see, and I was definitely getting close. She finally said, "Fuck my ass."
I pulled out, but I guess any prep-work she'd done in advance had been undone. Even with as much lube as we were using, I couldn't shove my cock all the way in. It ended up being enough for me to shoot a load in her ass, but I don't even remember getting the head all the way inside.
As I predicted, we did end up fucking a lot that weekend. However, there was a change. As part of every bit of foreplay, she had to get her ass eaten. That ended up being almost universally true every fuck after that weekend. Soon fingers and toys were introduced to her asshole, and she ended up liking it every time. During that relationship, we bought one vibrator...
...and eight (I think) different toys for her newly needy ass.
An obsession was born.
And, in case you're wondering, no, I never did get to actually fuck her in the ass. I missed out on Birthday Anal, and any anal with her altogether.
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