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Broken Dreams, Broken Buttholes

Broken Dreams, Broken Buttholes

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1
Anonymous
@confessions
4d ago
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A long time ago, the strangest thing happened to me, I still think about it fairly often over the years. Lately it's been back on my mind a lot, for whatever reason.

I had been swimming with my friend Nicole, and afterward we decided to go back to her place and hang out. We got there and there was nobody else home, so we grabbed some snacks and soda and headed to her room.

We had been casual acquaintances for a couple years, but we became better friends the beginning of that summer. I hung out with her brother sometimes, mostly in the computer room, but I had never been in her room before.

I remember she had bunk beds for some reason, the weird kind with a big bed on the bottom and a slightly smaller bed on top. I have no idea why, either. She had siblings, yeah, a brother and a sister, but they had their own rooms, and her sister was a lot older, by maybe seven years or so. Older to the point where I was surprised she was still living at home. I could only guess that maybe they were a holdover from some time she shared a room with her older sister or something, I never asked and never found out.
I was also extremely jealous because she had a cable box, in her room! Even if my mother could have afforded such a thing, she never would have let me have one, I was stuck with cable coming straight from the wall, like a chump!

She said she had to wash her hair and left to go take a shower. I was sitting on her bed, flicking through channels, watching Nickelodeon or MTV or whatever. I won't lie, I was thinking about her in that shower. We were friends, and I had no delusions of us being more, but she was quite a looker.

Eventually she returned to the room, wearing only a towel... on top of her head! Otherwise, completely stark naked! I tried not to be noticeably surprised, I tried not to have her catch me gawking like a geek, whatever, but she didn’t pay me much notice. I expected her to, like, shriek and back out, like she forgot I was there or something, but she just came in and closed the door.

It wasn’t anything sexual, either. She didn’t come on to me or anything, she just went about her way, casually getting things out of her dresser, looking in the mirror, moving stuff around on her vanity, holding a casual conversation about what was on TV or whatever, I could barely think because I was so distracted. She was acting perfectly normal other than the fact that she was naked.

I couldn’t help but sneak peeks, and longer looks whenever I got the chance, not like I had to worry because it wasn’t like she was trying to catch me or anything, but I was still worried she might. I had no idea what was going on, still don’t to this day. Her family weren’t nudists or anything, as far as I had ever known. I had been to her house before, nothing like this ever happened.

I fully believe she wasn’t coming on to me or trying to entice me in any way, either. I've told a very few people this story before, and they all seem to think I missed my cue, like she was giving me a signal, but I sincerely doubt it. She never gave me any kind of look or approached me in a proactive way or anything, there wasn’t anything sensual or cloying about her manner. She acted the same way she acted while clothed. I’m pretty sure if I had tried to hit on her or touch her or anything, she would have thrown me out. I didn’t so much as comment about her nudity, for fear of ruining anything.

Instead I just accepted the strange luck I had been given and let my eyes absorb everything. For a good while she stood in front of her big vanity mirror with her back to me, giving me a good look at both sides. The mirror wasn’t full length but it was big enough to let me see everything. I remember her wispy blonde pubes, thin enough to let me see the lips of her vulva beneath. I remember her holding the towel with her left hand while bending over to retrieve something from a low drawer. The dimples on the sides of her butt.

Eventually she took the towel off her head and dabbed at her legs and backside a bit with it, before brushing some kind of products through her long blonde hair, still nude the entire time.

I tried not to be visibly excited but I was exploding, in my mind. She shook her still damp hair and retrieved some more things from her bureau.

Eventually she put on a white, lacy bra, not see through but frilly, and then some shiny, slightly blue panties, I watched her pulling them up the entire time, wishing I were them. She finished getting dressed and opened her door, then came and sat beside me on the bed, her hair was still slightly damp.

We sat there watching TV and chatting, eventually her father came home and greeted us, soon enough the rest of her family was there, as well. I was still running her previous nudity through my mind the entire time.

After who knows how long, it got dark, I left and went home. She and I were still cool that entire summer, still hung out at the pool a lot, but there were no more nude house visits after that. I hung with her at her house a few times after that, sometimes we were alone again, but they were all normal, fully clothed hangs. Much to my chagrin.

After that summer we were still cordial, but she was already moving on to different friends, mostly girls, generally stuck up snobs. We would see each other in the hallways and be cool, but we weren’t really hanging out anymore. I still hung out with her brother sometimes, but she would only barely acknowledge me when I was over.

We fell even further out of touch after that, maybe an acknowledgment in the hallway, head nod or a smile, but no more friendly stop and chats.

After a while I realized I stopped seeing her or her brother at all and found out months after the fact that they had moved to another city, entirely! Didn't even think to tell me about it, the last time I had hung out with her brother, nobody had mentioned anything about moving.

I never found out what was going on that day, never found out if hanging out naked was something she had done with other people or something, like it was just normal for her, never found out if she thought I was gay and that’s why she was fine being naked around me, never found out if I was actually totally wrong about it being innocent casual nudity, nothing.

Even to this day I would love to ask, if I somehow got back in touch with her. If she would even remember at all, or if she would remember but pretend not to, or if she would think/pretend I was making it up and being some kind of freak for even bringing it up. Like I was trying to get with her or something. Maybe be freaked out that it's been on my mind this many years later. I just want to put an end to my nagging curiosity, is all.

The whole thing was very weird, and she’s almost become a bigger part of my memories, than she ever was a part of my life, which is sad when I think about it, especially with how important it all felt back then, friends seemed like the biggest thing in your life, people you would know forever, and then one day you just, never see them again. It's an odd feeling when a memory seems more real to you than the person the memory is about, has a bigger impact on your life than the person it's about.

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2
UnLuckyDP
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@random
06 Dec 2025 5:34PM
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I have a little confession to tell you.
A few years ago, I dated a girl who was 10 years younger than me. I knew she was desperately in love with me and would do anything to please me, so I played mind games to see exactly how far she was prepared to go. I kept dropping little sexual things I would like to see her do, and she did everything, no holds barred. Things got a lot more adventurous, and I kept pushing the boundaries. One night, I said I wanted her to take a massive cock inside her, and I wanted to watch. To my surprise, she agreed as long as it was a BWC, I asked if a BBC would be better. No, I only want BWC, and I will want to be tied up and blindfolded. A few weeks passed, and nothing was mentioned about this. I was working on things behind her back, then I took her for a night out, wine and dine type thing out and ran into my mate (old-arranged, of course). I introduced him, and she seemed to like him. As the night went on, I brought up the subject of watching her. She was a bit tipsy, looked at me and said If you really want me to, I will, but I want to see just how big his cock is first, it has to be bigger and thicker than yours, By the way, his nickname was horse for obvious reasons. When she saw it, her eyes almost popped out of her head. OMG, are you sure? Yep, I'm sure,
Remember, blindfold and tied up, we went back to our apartment. Before long, we had stripped her naked, blindfolded her and tied her face down and her ass propped up in the air as we had shoved 3-4 pillows underneath her. I put her favourite vibrating toy in her pussy and left it buzzing away inside her. My mate and I left the bedroom and our naked girlfriend to get some drinks. Unbeknownst to my girlfriend, I had other plans. I had actually asked 7 other of my mates, all very well endowed, the smallest was 8 inches, but extremely thick, the biggest and thickest was, I guess, a good 11-12 inches long with thickness. Another thing I had not told her was that my mates were only allowed to fuck her in her tight, almost virgin ass. I walked back into mt bedroom, walked up to her and whispered in her ear, I was going first, and I was fucking her in her ass, and I was going to pile drive into her. At this, she began to try to get loose, shouting Not in my ass, please, you know I don't like it, please no!
I took her anyway, as she cried, begging me to stop. After I had finished cumming over her back, I called the next guy in, and I made sure she heard me say Remember, as agreed, ass only, 1 by 1 We all took her ass somewhere rough; some just made love to her ass. There were more than a few spanks, we even tried double Anal, boy did she scream. After all my mates had had their fill, some took her 4-5 times in her ass and came in her mouth. They dressed and left. She had absolutely no idea who had fucked her ass, except my mate and me, whom I had introduced to her. He also left before I untied her and took the blindfold off
She wasn't happy I had to carry her to the shower as she was so weak she could hardly walk, plus her ass was really, really red, raw, super sore and gaping wide open. After she was showered and clean, she asked me why I had made her do that. How many were there?
What had she done to deserve that?
Well, my dear, I said, remember you said you hated cheats? yes ? Well, why did you go and cheat on me? Who ? When ? How did you find out ? Who told you? is what came out of her mouth. Then the excuses came, I was dr*nk, etc, etc, etc, I'm sorry, it was only one time. I replied, It's ok, hope you enjoyed your one-time cheating on me, and I hope you enjoyed having your ass gangbanged.
In the morning, I will help you pack all your stuff up, as you will no longer be living here. I will drive you to you chap you cheated on me with; you are his problem now, she cried all night, kept saying I'm sorry, I will do whatever you want, please, please don't do this to me, to us.
In the morning, she begged me to let her stay with me, not to take her to the other guy's house, if she had to go anywhere, take her to her mum's, as the other guy was married. I replied I know he is married, he was my best mate, I asked him to be my best man if I married you, as we pulled up outside his house, I got out and dumped all her stuff on his door step i rang the door bell his wife answered asked what all this was about, I said ask her and ask your husband, I pulled her out my car, then i got in and drove off,
Don't ask me what happened as I drove away and left them to it

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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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