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Desperate Times, Desperate Measures

Desperate Times, Desperate Measures

Lana Rhoade's Biggest Regret

Lana Rhoade's Biggest Regret

Wrong Hole... LIKE A BOSS

Wrong Hole... LIKE A BOSS

EPIC Butt Plug FAIL

EPIC Butt Plug FAIL

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Cumshot Fail

Chef Boyardee Jizzes Upon Contact

Chef Boyardee Jizzes Upon Contact

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5
Anonymous
@confessions
06 Dec 2025 5:09AM
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I finally had my first anal experience.

I am seeing this married woman for almost a year, it is a thing from work, that escalated to FWB situation. She is a beautiful woman, little bottom heavy, but still very, very good looking for a 40 year old.

We fuck once or twice a week, and this is an arrangement I am totally happy with. Now, the confession part is, that last week, we had sex, she had already came when we switched to spooning position. I kind of separated, if you understand what I mean, to enjoy the view of coming in and out of her, so I was going all the way in and all the way out, she was wet that much, that her thighs were all sticky. I was doing this slowly, and she loved it, and one time that I was going back in, I kind of missed, and pressed against her asshole. I did back out immediately, but she reacted with a loud moan. So I pressed against her, kissing her neck, now trying to "miss" on purpose. And I did, and loved her reaction. Everything was so wet, that when on the fourth or fifth "miss" I pressed, and did not back out, it just went in.

She moaned loudly, and turned to kiss me, eating my face from lust. I managed only three more strokes and finished inside.

After the shower, I asked her if she enjoyed it, and she said yes, admitting that she had no idea that she might enjoy such a thing.

I am seeing her Monday after work, and I think I just struck gold.

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4
jessxxx
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@confessions
3d ago
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A confession.
when i have sex i ask bf to put a vibe/ dildo in my ass as he isnt really into anal. Does this make me strange ? 

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Anonymous
@random
4d ago
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My wife. Do you think she likes anal sex ?

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ProfessorBobo
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@confessions
14 Dec 2025 2:01AM
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Back in the day, I got with my friend’s ex, behind his back. They weren’t serious or anything, and he would constantly complain about her to me. Plus, I knew her first, so I didn’t see it as much of a thing.

Me getting with her wasn’t exactly unprecedented either, before they had even met, she and I had been flirty and sort of dancing around the sword, I’m actually the reason she was hanging around and they met in the first place, I was talking to her but we hadn’t done anything yet, there were a few women I was courting at the time, and one random day he just asked her out, first. I wasn’t mad about it or anything, totally fair play, but I did think he had perhaps done so to, undercut me, kind of show me up or something, but it didn’t bother me. Hey, I had irons in the fire!

But he would always bitch about random problems he had with her that were either completely minor, or invented, like he was just taking issue on purpose to be difficult. He kept complaining that she was annoying and the sex “wasn’t even worth it” because she was “too freaky”, I kept telling him stop being a prude and experiment, go with the experience, but it would actually bother him, he would get angry for real, so I stopped and just let it be.

After maybe three months they broke up, I was surprised it even lasted that long, and I did ask if he would be bothered if I picked up where she and I left off and make a move, and he actually said yes, he was mad that I asked! Considering how poorly he treated her, I figured it was hardly his place to take issue. So I resumed talking to her, anyway. She was surprised that I was still interested and didn’t consider her “sloppy seconds”.

We never formally dated, but very soon after that we were hooking up. She was kinda freaky, I will say. In a good way, though. Nothing too far, at least for me. She liked anal more than vaginal, which had been a huge problem for my friend, but no issue for me! It was a total plus! Hell yeah!

This was back before anal became the mainstream thing it is today, but I’ve always had a thing for it, and I’ve been really lucky to mostly find women who were into it, too, or at least willing to try it.

Other than that she like some very light bondage, barely even bondage I’d say, liked to have her hands tied, liked to be held down, like, shoved down, pushed into the bed/floor, spanked fairly hard on the ass and sometimes slapped in midsection during sex, really minor stuff like that.

The freakiest thing was, she liked to be peed on, sometimes. I also had no problem with this, it’s not exactly my thing, but if it turns you on, it turns me on! She would kneel in the shower and close her eyes and I would piss all over her pretty face, or she would bend over and I would piss all over her ass and back, sometimes she wanted it on her feet, or her tits and stomach. She didn’t drink it, she never tried to make me play with her while she was covered in it, and she never asked to piss on me, I might have let her, hey, I’m adaptable!

We hooked up off and on for the next year or so, it was great because she was down for anal every time, sometimes I wouldn’t even fuck her ass as a form of teasing. My friend never found out, at least as far as I know.

I’m not really a prude but I’m not much of a kinkster, myself, other than anal and ass eating, which were once considered semi-kinky, I’m pretty much a “mostly normal sex” dude. She was probably the freakiest girl I ever hooked up with, and it wasn’t even that freaky in the grand scheme of things.

She had cerebral palsy, and a few years later, I
hooked up with another chick who also had cerebral palsy, and she also preferred anal (never found out if she liked being pissed on, though!) and it’s kind of given me the probably-false stereotype that all women with cerebral palsy prefer anal. Sometimes I’ll watch one of those comediennes who have cerebral palsy and assume they prefer anal. Let me have my fantasies, okay!?

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redblackpassion
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@confessions
2d ago
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married to a slut who likes to fuck young black men ,she is over 30 and has set her next goal at a 100 ,Tanzania Morocco Malawi had the best sex , in Malawi she had her first gangbang ,she fucked the biggest dick she has ever seen live in her life ,tried anal sex with a black man ,is searching the internet for the next African country we'll visit

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