Anonymous Confessions

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Welcome to the ultimate confession booth, Men Only!

This is the space where you can share your deepest, darkest, and most embarrassing misadventures without judgment. Have you ever found yourself in a cringe-worthy situation that you couldn’t shake off? Perhaps you got caught checking out your boss's wife, or you accidentally sent a sext to your mom instead of your girlfriend. Maybe you were the guy who couldn't hold his liquor at the office party, or you clogged the toilet at your date's house.

We understand that being a man comes with its own set of unique challenges, triumphs, and mishaps. From awkward boners at the most inconvenient times to embarrassing wardrobe malfunctions, we've been there. This is your opportunity to share your stories of masculinity in all its glory, from the hilarious to the humiliating. So go ahead, confess your secrets and release your burdens. The community is here to support (or laugh at) you bro, no matter how wild or embarrassi

- Masculine Misadventures -
Straight Male / 48

I have several businesses, dealing mostly with real commercial real estate. I ventured out and started buying office buildings in downtown areas of major capitals and I went to Oslo to look at a building. I arrived from Hamburg and caught the train into town, I was traveling light with an overnight carryon and when I arrived at the station to go find my hotel it was raining. I stayed under the cover of the station to let the rain go by and this girl was standing there so I spoke to her. She answered and said she was a student in Oslo but she was Kiev, a Ukrainian girl. I guessed her age somewhere in her early 20s.

The rain stopped and we got ready to walk out to the street and asked if she wanted to share a glass of wine with me and she accepted and we stepped into a street side restaurant and ordered wine. She was studying Political Science and I told her it was a waste of time but European's seem to like that type of worthless careers. We had two glasses of wine and in the conversation she told me that her University was a couple of blocks away and her apartment just down the street from the University.

We walked and found the building, a pretty worn down affair without an elevator built in the sixties when Norway was one step from being communist. Her room was small, a little bed and a kitchen top with a shared bathroom at the end of the hall. She took off her shirt, she had a very small bust, took off her pants and underwear and said she charged fifty Euros and I sat on the little chair and I told her I don't pay to fuck. She put her shirt on and her pants and she started to heat water for tea. We talked for a while and I told her that a free fuck I could do but I wasn't going to pay for it, there was just too much free pussy out there to pay.

We had out cup of tea and she said she would do it for free and she took off her shirt and her pants and went to the bed and spread her legs open so I sat there and just looked into her eyes and her soft furry pussy and asked her what it would take that instead of fucking her pussy she let me fuck her behind. She sat up and said no, she never did that. I asked again and told her to bend over the bed and let me see if her little dark hole was something I wanted to fuck. Her hole was dark, it is funny for the fairest skin girls to have such a dark hole with her hairy pussy extending high up and swirls of hair covering her hole.

I asked her if she had anything to lubricate her so that it would not hurt her and she said no so I took my fingers and felt up her vagina and spread some of her vagina lubrication around her hole and stuck my cock in her vagina and got it good and wet and then I told her it was time so she should brace herself in case it hurt. It did hurt I could tell but she kept her mouth shut and when I finally got my cock in all the way I told her that what I liked was for her to sing a song to me while she got fucked. I wanted her to sing a Ukrainian lullaby while my cock stroked her hole.

When I let all my juice in her and withdrew her hole was red and swollen and I had her stay in position while I touched her hole gently with my finger and asked her how she felt. She stood up and used a small towel to clean herself and I took the towel and ran some water from the sink and washed myself and told her she had done well, that a tight little asshole fuck was something that I enjoyed. I got myself together and told her I had to go to my hotel and she walked down to the street with me and I walked to the corner and on to my hotel which was six blocks further down.

Her name is Anatalia, she is 25 and she has finished her schooling and she works for me as the building manager in Oslo, I have an apartment there in the nicer part of town and she lives there and takes care of it for me. I take her to London on shopping trips, and once or twice to New York to see the sights and go to the theater. I love to take her to nice stores and buy her things, and of course one of my goals is to take her around the world and fuck her skinny ass overlooking the various iconic spots around the world. She is not a girl who looks for things to buy, she likes her job and does a good job for me. But for me she is a jewel in the raw, she needs polishing, and she is learning that she is mine, I keep her and I fuck her. If I can't get to Oslo she comes to where I am. She is my fuck, skinny legs and all. I just love to fuck her ass. I love her mouth around my cock. I love her hot little pussy. I love her eyes and the long slim fingers on her hands. I love her made up and love her when she wakes up. She is such a good fuck. I never complain about the rain in Oslo, if it weren't for that my little jewel would be with someone else by now.

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# 43501 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 53

    When we were growing up we had a park that was a block away from our house. After school we would go ride our bikes and we would end up at the park to catch up and drink from the water fountain. That afternoon there was a little girl all by herself, swinging with no adult nearby. The swing went up and so did her dress and you could see her white panties up between her legs, we sat on the bench and watched as she flashed us.

    When she got off the swing we went over to talk to her and she told us her mother had left her there because she was going to a meeting. She had a sandwich in a paper bag in case she was late. We stayed with her and it got late and then dark and the mother didn't come back. Finally we knew we were so late that we were going to get in trouble and my friend took off to go home. I convinced the little girl to walk home with me, she couldn't stay out all night.

    That is how we ended up taking her in. She lived with us as a throw away child and my mother made me look after her. I had to walk her to school and go to school to walk her home. I had to play with her after school and not go bike riding with my friend. She was good at puzzles and stuff. I guess I never paid attention to her clothes but my Mom bought her real nice things and fixed her hair every day and she got a fattened up as my Mom would say. As to age, she was six when we took her in. And she was now my little sister and I made sure she never flashed her panties to anyone.

    When she got to that age when everything changes she turned into a beautiful swan, every stupid boy within ten blocks was after her, I had this baseball bat that I kept in the car and I would stand outside on our driveway with the baseball bat. Everyone knew that getting close to her was a death wish. Seventeen and she was the talk of the town, by then she was adopted and she was my sister and no one really knew she as adopted. She was a stunner, smart like smart and so damn pretty that she stopped cars. Watching over her was hell, except that she was real obedient to me. If I said no, it meant no.

    I got done with college and what was I going to do? Let her go by herself to some college where there would be nothing but vultures? No way, so I convinced my parents that the best thing for her was to come live with me and go to the city college. That is where we committed adultery, committed i****t between brother and sister. Sure it was glorious, sure it was like a gift from heaven, sure I lost my virginity and so did she. But it was adultery and I guess i****t, making love like that with your adopted sister. But we could not stop, I don't doubt that I was filthy horny about her but so was she.

    If I thought that a little bit of play got me somewhere we did it, but she always took it up three levels, nothing stopped her from wanting more and more. She wanted sex all the time and I felt guilty about it but she didn't. She was born to have sex with me and she intended to make her birthright known. Outside in the open world we were two loving siblings who took care of each other, she cooked for me and took care of the house and went to college and I worked and paid the bills, but at night she was a sex machine, a beautiful sex machine. It isn't very manly to say that I could not keep up and lots of time she sat looking at me with a big lip because I just had to take a break.

    The day came when we had to tell my parents that we were active and that we wanted to get married. The legal world got easier when she was adopted but not easy by any means. The adoption had to be reversed they said, the state just did not let a brother marry his sister. In the meantime we had sex. Finally the adoption was annulled and we were able to get married. Lots of problems in the neighborhood, and with some of our extended family but in the end it was accepted, I had found her she was mine to keep.

    Been forty years now, still the brightest star in my sky, still beautiful, she will never not be beautiful, still has an engine that won't slow down. One thing for sure, I never had enough gas to mess around, she emptied my tank.

    0
    # 43473 - by Anonymous
    - Masculine Misadventures -
    Bi-Sexual Male / 46

    I used to Love fantasizing about being naked and forced to Suck a stranger's Cock, one day i made it happen, i was chatting with this guy explaining to him my fantasy, he asked where i was he said he could meet in 30 minutes and did i have any place in mind, I suggested my local shopping centre restrooms i had used them once in the 10 years I was living there and they were spotless clean with 5 stalls. I was sitting there naked in the last one stroking away my head was spinning, feeling a bit scared, what if he doesn't look like what he said or something bad was going to happen, 40 minutes had now passed and i was thinking he isn't coming, when i heard footsteps, again. Then he stopped i could see his polished shoes under the door, then he tapped 4 times, i opened the door right on the last tap and was very relieved to see a handsome man maybe 40 in a suit, i recognised him from one of the real estate places there, he came in unzipped pulled out his lovely cut Cock which quickly hardened to 8 inches at least grabbed my head and pulled me to him i opened my mouth as he forced that lovely big Cock in my hungry mouth, at first he was gentle sliding it in me slowly and a bit more each time, after a couple of minutes he was resting his balls on my chin as he held me firmly with what felt like his whole Cock buried in my throat, i did not seem to have a gag reflex, and i was loving it, what a feeling this was in a public place being fed a Big Cock, of course I was really loving it and then we heard footsteps, he pulled out, i pulled him back in and held him there in my mouth as the guy finished his piss and left. Then he was like a man posessed he held my head tighter than before and Fucked my mouth and throat with such force that I barely had time to catch a breathe as my throat started to sting A bit, Then he slowed his thrusting as i felt his Cock swell before his warm juices began to spurt sharply in my mouth then he forced his big meat slab back down my throat and he emptied the rest of his massive load i knew I had to swallow quickly or I would pass out from no air, when he finally pulled out I drew a huge sigh like breathe and the air gushing in enhanced the smell and taste of his salty semen that lingered long after in my mouth, he tapped me on the head with a good boy, tidied up and left, i sat up to close the door behind him just as another guy walked in and must have seen him leave my stall and that I was still naked, he changed directions and was heading towards me I managed to close the door but not enough time to latch it, he pushed the door so hard I flung back against the cistern and by the time I'd sat back up he door was now closed and he was pulling out his Cock, you want more he said ?

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    # 43465 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 44

    Just an ordinary guy who appreciates a surprise. There I am in the men's room standing at the urinal and in comes this hot looking girl in her twenties, I turn and looked at her, she stares at me and walks up to the urinal, lifts her skirt up and pulls a penis out of the side of her panties and starts to pee. I stare, he gives me this look, he shakes and sticks his penis back in his panties, lowers the skirt, stops in front of the mirror, fixes his look and walks out. I am standing there and slowly get my penis back in my pants, wash my hands and leave.

    Museum of Modern Art men's room July of 2015.

    1
    # 43366 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 29

    This goes back to Junior High School. There was a party, with a couple of the mother's as chaperones. We went outside beside the pool to talk, and I asked this girl Stephanie to go see what was on the other side of the pool. When we were there I said let's go look at what is down there behind the pool shack. When we were there I told her that I had tricked her and I wanted her to let me kiss her. She got kissed and she got felt up including her pussy. After that she said she was my girlfriend and no one else would talk to me. She had told the other girls that we had done it and no one else would be my friend.

    To go out we had to be driven by a parent and we went mostly to the movies. In the movies she wanted my arm around her, and she put my hand under her tit. She rubbed my pants and several times took my prick out and she held it and rubbed it and several times she got me to cum. She was a kisser and expected to spend a good part of our date making out, she liked to have her tits rubbed when we kissed or have her pussy fingered. When we went to this lake house for a class party she expected me to take her to one of the rooms and get it over with, she went prepared she had a condom and she made me stand beside the bed while she put it on and she lay back and spread her legs. We fucked.

    At her house if we were upstairs alone she gave me hand and oral sex until I came then she let me watch television in peace. She had condoms all the time, she got them from her older sister and we had sex in her room, a couple of times totally naked. She was open to try anything, front or doggie style, sitting on my face or kneeling and giving me puppy dog eyes while she gave me a blow job. She never stopped. I didn't know what a nympho was but she was a teenage nympho.

    For Thanksgiving at her grandmother's house she suggested that we go outside, it was cold but we went outside anyway. She wanted me to announce to her family that we would be getting married when we finished high school the following spring. I had to stand and tell her family. They asked for the ring, no ring then the engagement wasn't real. I had to get my mother to give me her engagement ring to give to Stephanie. She wore the engagement ring to school. Sex never stopped, she was always ready and she gave as much as she received. Her goal was one and only one, I would never have enough energy to look at another girl. In our senior year there was no curfew and there was no off limits place for us to go, including into her bedroom. Everything was foreplay, in the end she needed to feel it, she needed it.

    On our wedding day, before everyone got together to go to the church we had sex in the bathroom. At the reception after the wedding she told me that she wanted me to eat her like I ate that cake. She was all over the place, she had on a new night gown that her mother gave her, new bra and panties that her grandmother gave her and she didn't ask me to wear a condom. For weeks we fucked day and night. The only thing that stopped it was her morning sickness which lasted most of the day.

    I come across as I am complaining and in a way I am. I am pretty sure that I am the only guy in my graduating class that has never been with another woman. I am also probably the only guy in my graduating class that got milked every day, one way or the other. Stephanie is who she is, she is a sex machine on overdrive. When she asks now to be tickled that is code for get under her skirt and give her a quick in and out. She has used a stop watch to see how long I can keep it up inside of her. She is an expert at giving me a hand job and an expert at giving me a blow job. She doesn't mind if the kids come to our bed and find us naked from the night before, that is what the sheets are for, to cover up. If there is such a thing as a nympho then Stephanie fits the bill. The only way I can get away is to go work out at the gym or go help my father with some construction project that he has going on.

    This is not an ugly woman either, she is downright easy on the eyes and she carries herself in a way that makes you want to look. Maybe it is the jack pot, but I am not sure that I can keep up the payments.

    1
    # 43333 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 44

    I have an obsession with seeing women I know naked. I don't necessarily want to fuck them. I just want this mystery solved of knowing what they look like nude. I've snooped rooms and stolen shit while fixing computers. I've gotten on sites with state threads and put out feelers, hoping some pissed off ex will see it and decide, "yeah, fuck her. Here you go." That has actually paid off more than once for me.
    I've seen friend's wives and girlfriends, family, coworkers, my daughter's friends. I've stood outside windows in the middle of the night and been the peeping tom on a friend's wife taking a shower, and the hot niece I see once a year.
    Last summer we rented a beach house in Florida. It was night and my wife went to take a shower before bed. I stepped out for a smoke and walked around to the back where it was dark. I glanced through the slats in the fence and saw a guy standing in the darkness, watching my wife. He was half her age, but he was there to spy on a naked woman. He moved closer and I stepped further down where I could keep an eye on him. He had a clear view through the slats in the vertical blinds and I knew my wife always leaves the bathroom door open. I knew it was a clear glass shower door and that he was able to see her naked the entire time.
    I knew he was seeing my wife's shirt come up over her head, and the shorts getting pulled down. I knew he watched her reach behind and unhook her bra, and then her tits hang free. I knew he watched her fingers slip into her panties and then slide down over her ass, and I knew she turned around and he was able to see my wife's shaved pussy and that cute crease that disappears between her legs. I knew precisely what he was getting to see because I've watched my wife undress a million times. I knew he watched her lather her naked body and reach between her legs, and then her full tits move in her hands as she dried them off after.
    Between knowing the excitement of what he was feeling and the thrill of seeing my own wife being spied on, I just kept quiet and watched. I let him have his show to the very end and watched him sneak away into the dark after. She was completely unaware and I really don't know the show he got to watch, but for those few minutes my wife was on absolute display for his private show. I actually enjoyed that betrayal of her trust because it was an unknown moment of loyalty to a fellow voyeur. It was MY wife someone wanted to see naked, and I guess it was both flattering and owed for all I've seen over the years. I know the thrill of getting that prize, and my wife was the prize that night.
    That stranger was half her age and took great risk for that reward, and I'm kind of proud that it was my wife he chose.

    So given the same circumstance of catching a stranger risking it all to see your unaware wife naked, would you chase him off and preserve your wife's dignity, or let the betrayal happen and enjoy the cheap thrill?

    And what is your experience at being a peeping tom? Who did you see that you shouldn't have?

    5
    # 43328 - by Anonymous
    100 of 40,960 Confessions Displayed.

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