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Most memorable anal experience.
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Fucking my wife's ass is always amazing. She needs to get slam-fucked. Literally, I sometimes suggest I could be gentle, but she whines and complains that she doesn't like it that way.

But this is about two times with another lady who actually somehow surpassed my wife's abilities. My wife got to witness this too, because that's how we play.

So, long story short, this woman I knew wanted me to be the one to introduce her to anal because I'm the safe, nerdy guy who also coincidentally knows how to take it in the ass. The trick however, was that when I was first intending to start, she kind of decided to take a job in another city and move away. Well, okay, whatever. I didn't expect to see her again.

Then one day about a year and a half later, she messages me on Facebook and says "Hey, still up for fucking my ass?" Oh wow. Yeah, sure, no problem. We set up a date and have her over at our place. I expect the usual sort of virgin experience, where she's going to be way tight, take a long time to get into it, and I have to be super gentle.

Wrong.

We're starting out in doggy style after lubing up, and I tell her "Okay, push back on me, you can set the pace... WHOA! Jesus! Be careful, or you'll hurt yourself!" She'd literally bent my cock in half shoving herself back at me. I didn't go in right away of course, but holy shit was she eager. It wasn't long before I was inside her, and she just ground herself back until I was in to the hilt in seconds. It's like... she'd been practicing on her own like I said she needed to, or something.

I ask her "How's that so far?"

"Oh ghod it's amazing! Fuck me harder!" It wasn't long before it was the complete opposite of the usual anal virgin experience. I was pounding her for all I was worth, and I commented about that too. "Anal virgin? No way, you're a total anal slut now, you filthy little whore."

And it got better too, because at one point I pulled out and she just instantly gaped. Big and wide, without even trying. I was beside myself. We went through a few positions before I ended by blowing my load on her face like she wanted.

I fucked her ass a few more times after that, but the best one was where that penchant for gaping came in. Seeing her ass wide open like that, I couldn't help but spit directly into her... and that made her cum. Like, massive, leg-shaking deal like I'd seen her do before, and I was just taken aback by it. "Was that... an orgasm?"

Her weak little "...yes..." after she regained her ability to speak was priceless.

I've never seen anything like it before or since. I had no idea it was even possible. Never heard of it, ever. If my wife hadn't also witnessed it, I would probably think it was some bullshit my imagination made up.

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2 months ago