Anonymous Confessions

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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 / 55

I worked at a hotel behind the front desk between college tries. A girl kept hanging around the front desk, and from time to time she would disappear and I would see her again another night. Frankly I was so naïve about it that it took another employee to tell me she was a hooker. I couldn't believe it, not her? She had to have been seventeen maybe eighteen, she was so small too, maybe five feet tall. But the show went on and on and on over several weeks and she came, hung around the lobby, talked now and then to a man and she disappeared until the next day or two and she was back.

I got friendly with her and got her cokes from the restaurant and she gave me her name, she was from Oklahoma and making a living. One day I asked her if she really was a hooker and she said 'yeah'. I asked how much for the night and she said I couldn't afford it but if I wanted a quickie she could work me in for thirty bucks. We went back to the stairwell behind the elevator bank and she lowered her pants and bent over holding on to the rail and told me to hurry up I wasn't paying for her to lose time. It was my first hooker.

She gave BJs for twenty bucks, same stairwell, thirty bucks for a quickie, but I didn't make enough money to get a treat more than once every two weeks when I got paid. One day she asked me if I had a nice place, maybe I could take her there and she would teach me and she whispered to me that it would be free seeing as she was teaching me. It was my first time naked with a girl, she was eighteen because I saw her driver's license from Ponca City Oklahoma. She got naked, like bare butt naked, for me. She stood naked and turned naked and then bent over naked and let me take a look at where the sun don't shine, to take a good look because she wasn't going to do that for free again.

We got on the bed and she told me to lay back and she got on her knees and started to work me into a hard on and suck me in deep long sucks, nothing like when she gave me BJs in the stairwell. She swallowed it and she told me she liked long hard dicks like that, seemed only right that she got to suck one down to the nub. She held and played with my balls while she sucked me. She got turned around and put her butt in my face and told me to lay my head down and stuck her soppy wet pussy in my face and I started licking and sucking and she kept on licking and sucking my dick. I think she had an orgasm because she stopped for a minute and then laid her pussy right down on my face again. It was about then that I wasn't able to hold it back and she took everything I had, she licked up and down my dick and cleaned her face with the sheet.

She got off and sat beside me Indian style with her pussy wide open, her crack split open, her dark red pussy in plain view while she continued to massage my limp dick. She leaned over and told me to open my mouth and she put her mouth above mine and she let some spit fall right into my mouth. She worked up the spit and she let her spit fall over and over again into my mouth. My dick started to get hard again so she bent down and gave my dick a long suck and she asked if I liked it hot because she was pretty hot. She got back up on her knees and she asked me if I liked her pussy, she asked me if I wanted to see where the sun don't shine again and she turned around and spread her legs over me and opened her butt wide and asked me what I thought about that. Her butt flower was quivering as she squeezed her sphincter and then she said enough of that, she just wanted me to see her because she wanted me to remember everything. She sucked me again and I was hard and she got on and fucked up and down for a while and then said that she wanted me to get on top but no kissing.

She lay down and opened her legs and told me to get on. She took my dick and lined it right up to her hole and it felt good to fuck, and I kissed her and she got mad and said no kissing, but I kissed her anyways and after a minute she let me kiss and she put her arms around my neck and we kissed as I pumped. Somewhere in there she let me go and said to go ahead and fuck her and fill her up so I finished fucking her and filling her up.

She slept with me and the next morning we went to breakfast at the Waffle House and she said that she could not be my girlfriend, I needed to understand that. But she was and I never paid for her again, and I never had to go to the stairwell again, we had sex in bed. If she had a client she would douche her pussy before she got in bed. Of course life is life and she could never really be my girlfriend and she moved on to greener pastures, a bigger and better hotel. But she was right, I never forgot her.

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# 43323 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 48

    Our graduation class of 1968 was a small class, there were only 28 students our senior year. Five boys and 23 girls. One of the boys turned out to be gay and he went to work as an airline attendant, one of the boys was killed in a traffic accident, I went to college, the other two boys went to work in blue collar jobs. Of the girls only one went to college and she became an English teacher. The other girls married or went off to work somewhere and it wasn't my place to follow up. We had our 50th High School reunion and all the ones that are alive showed up.

    It was a quiet affair, everyone's life having been so different. I managed to do well for myself, not rich but certainly well off. My school mate guys are good at their skill sets and still work, but by far they are not well off, mistakes, bad decisions, and low paying jobs taking away their chance for a retirement without worries. The women, some are married, others went through marriage and divorce and a couple never got married and that left my classmate who became a school teacher. The two of, the only ones with college degrees sat at the same table staring at each other.

    She asked me if I remembered the day she got down and she couldn't cover herself and I saw her panties. We were in the tenth grade. I said I sure did. She asked me if I remembered the day when we were on a field trip and I told her I had a boner and she sat with me on the bus until it subsided. I sure did. She asked me if I remembered when we were in the seventh grade and I had to kiss her playing spin the bottle. I sure did. She asked me if I remembered our first car date and how we had gone to the makeout spot and no one was there because it wasn't the makeout spot. She asked if I remembered how I had put my hand in her shirt and touched her tit. She asked if I remembered when we were seniors in college and we had gone to the movies to see Young Frankenstein and she had held my naked boner in her hand while we watched the movie. I sure did. She asked if I remembered taking her to my friend's apartment and laying her on her back on his bed and taking advantage of her. I sure did. She asked me why I didn't marry her.

    I didn't have an answer, she was destined to marry me but I never asked her and after I went to work and she went to work she and I remained friends and one day I married a girl I had met at work. She spent her life never having been married and I spent my life married to the wrong person. I don't think I ever loved my wife, my wife was just in love with the idea of being married. We divorced after 30 plus years. But here we were 50 years after graduating from high school and I apologized to her for wasting her life and mine and we got up and went to the hotel room and we had sex. We made it official, we are married and we are both healthy senior members of society, I have my life well taken care of and she has her pension from Teacher's Union and we spend our days traveling, and having sex. No lights on in the room, it is all under the covers, but it is sex and to tell you that it is the best sex of my life is not an exaggeration. And yes, this time I am pretty sure that I am in love, and I know for sure that she is in love. In fact I know I am in love and I was always in love with her.

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    # 43319 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 54

    I grew up in a small town in East Texas near the Louisiana border. My father was clerk for the city and my mother was a homemaker. I was their only child and our only entertainment was church. The school board decided to bring two high schools together because there were too few kids for each, for me it meant riding the bus forty five minutes each way. At the new high school, which meant we now were merged with kids from another town, I got in trouble. It happened at one of the track and field events, at that time I ran track. She was there, her name is Sarah and she was the daughter of the town bank president, she lived in the big house over by the lake. She had a maid and this black man that drove her mother around. That day at the track meet I took her with me into the building to find a restroom for her. I took her to the restroom that the coach used, not the girl's restroom in the building. I told her I wanted to watch, I had never seen a girl use the toilet. I took out my pee stick and peed first, showing her how it was done, I showed her my pee stick and let her touch it. Then it was her turn and she looked at me with crazy eyes and she pushed her pants and panties down and sat down to pee. I wanted to see her pee so I opened her knees and she peed all the way and her eyes watered up. When she stood I examined her, touching her with my fingers and looking at her. I took my pee stick out and pushed it up against her, she stepped back and fell back on the toilet. I told her to kiss my pee stick and she did. I rubbed her lips and she twirked her tongue like a snake to lick it and I was hard by then. I pushed my pee stick into her mouth, she more or less gagged so I pulled it out. I stood her up from the toilet and I put the lid down and sat down and turned her around and licked on her slit through her bush, I held her butt cheeks in my hand and dug my nose and mouth into her. I then stuck my hand up between her legs and ran a finger deep into her vagina, I got her to kick off her pants and got on my knees and lowered her panties until she got them off one of her feet, licking and sucking on her pussy all the time. The world could have come to an end but there was only one thing that was going to happen, right there on the bathroom floor. She took it with her legs wide open and I fucked her as deep as I could until I just came with all my dick snot going up high inside her pussy. When I was done I stood more or less and helped her stand and let her lean on me as she got her panties back on and then her pants and slip on her shoes.

    The judge yelled at me, and kept telling her just how sorry he was that she was in this predicament, but the law was the law and taking into consideration who she was and all he was going to allow her to get married instead of sending me to reform school and sending her to a home for unwed mothers. Me, well he gave me a lecture on that fact that I was now responsible for a family and if I messed up just once he was going to take matters by the letter of the law and I was going to reform school. The judge officiated at the ceremony in his office, her mother wore black with a veil and her father stood stiff as a board. My mother cried and my father slapped me on the back and told me I had screwed up and now I had responsibilities. This was serious, she couldn't possibly come live with my parents, not in our town and certainly not in our small house so the only answer was that I had to move in with her and her father made sure I had a job as a clerk in the bank. Life in her house was bad for me, a regular 64 dollar prison, they had color television and we didn't have to share a bathroom and there was a maid to clean up and wash the clothes and make the bed. I won't go on about how it was but one day she and I had snuck off after dinner and we were necking and getting serious when her mother walked in on us an she started to yell. Her father came in and told her mother that she was a woman now and anything that I did to her was legal.

    Anyway that is how I got in trouble in the ninth grade with a seventh grade girl. She tells the story different, not quite like that, she tells a more romantic story but there was no romance that day at the track meet, there wasn't nothing but lust in my loins and she was the object of that lust.

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    # 43306 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 50

    I grew up in a small town in a small catholic country. Our family owned the small hotel and restaurant in town and my grandfather had been mayor and my father was mayor at that time. We had one Catholic church and we attended the Catholic school. Everyone knew each other, everyone knew each other's younger and older brothers and sisters. Everyone each other's parents and grandparents. It was a small town.

    My cousin who was in the second year of secondary school told me that she knew of a girl who was the girlfriend of the Nun that taught social studies. She said that her friend told her everything and she told me in great detail what the girl did with the Nun. It would be many years later that I would learn that my cousin was the girl but I never knew at that time. I apologized to her and she told me not to worry about it, she wasn't the only one and if that is why she liked to be with girls or maybe because she liked to be with girls the Nun picked her, on one will ever know. I didn't know until that day that I apologized to her that she liked to be with girls.

    My cousin liked to tease me, tell me stories about what she did with girls, what felt good to do and what she sometimes had to submit to. But one thing was always the same, she loved to kiss girls, she is and always has been very romantic. We were at university at the time and she let me meet her girlfriend. She was from another town and they lived in the same student house. If you walked down the street you would never guess that either girl would be like other girls. But they did and they proved it to me by kissing right in front of me. It was from my cousin and her stories and her telling me what she liked that she taught me what to do.

    I met this girl at a party. She was from another town, her parents were Italians just like us, she had something about her and after several times going out with her I was able to convince her to go with me to this small hotel close to the university, it was well know for taking girls there. The room was small and there was only a bed and a small washroom. She told me I was crazy she wasn't a whore and she left. The next time I convinced her to be alone with me was after a party and we went out into the gardens and she let me kiss her. I let my hands find her shirt buttons and unbuttoned her shirt and she let me kiss her breast. The third time I invited her to the movies and I had rented a room at a nice hotel and after the movies I took her there and she let me take off her clothes and make love to her. I did everything my cousin told me about, things my cousin had told me that felt good to girls.

    I had finally at the age of 21 lost my virginity. The first person I told was my cousin. She laughed and told me that if I had wanted to lose my virginity why hadn't I told her, that was what she was for. My cousin found another girl, she was the daughter of a doctor and lived at home with her parents. That made it difficult for them to get together. My cousin asked me to take her out, her parents would let her go out with me and that way I was able to let my cousin and her friend get together. More than once I rented a room at that hotel where I made love for the first time. Only this was for my cousin and her girlfriend.

    We graduated from university and it was time to get married and I asked my girlfriend and she agreed and we had a traditional wedding. We invited my cousin and her girlfriend and I made arrangements for them to see each other on our wedding night. My wife and I stayed very close to my cousin and her girlfriend, as we grew up they kept their relationship pretending to be good friends and my cousin lived with us and her girlfriend lived with her parents. For many of us, we all knew they were together but it wasn't something you could talk about. My wife was very close to my cousin and our home was a safe place for them to be together.

    It was sometime later, when I was in my forties that a friend of mine from my school days told me that he joined the Opus Dei. This was very religious and he told me that he had wanted to be a priest but his parents had said no. He also told me that he was gay. It doesn't matter how much you want to act normal, you can't. I didn't know what to say, I knew my cousin was a gay woman, but him gay? And he wanted to be a priest and he joined the Opus Dei? He told me not to worry, he wasn't alone. Today it doesn't surprised me, but then it did.

    My son is gay, he is in New York and he works for a shipping company. It was my cousin who helped us. We live in Miami now and there are gay people everywhere, but it is different when your son tells you he is gay, especially that he is gay and he is the boyfriend not the man. I have not yet come to accept that he is gay, I never had to accept that my cousin was gay, it just wasn't something that bothered me that she loved another girl and my wife and I did everything we could for them to be together. It does bother me that my son likes a man and to tell the truth I don't like him. I prefer that I never see him. It bothers me that my school friend is gay and he is in the Opus Dei.

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    # 43299 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 18

    I'm almost 19 & I always thought I was straight until last November. I've had two girlfriends since I was 15 & I had good sex with both. I wasn't dating them at the same time. When I fap, I always think of stuff anyone would consider straight. Sometimes I just do it fast though to get off not even thinking much about any fantasy. Last November, I went with my parents to visit my grandparent who lives a long ways away. We went by car & it was a long drive. We had to stay at a hotel one night after driving all day then we got there later afternoon the next day. We made lots of stops mostly because of my mom. She always has to get to a restroom. There was this huge gas station place. That type where those big trucks pull in on the back side & everyone else on the other side. There was a fast food place in there & also a restaurant. My parents had us eat in that restaurant & we were there a while. I was horny like always because I need to get off two times a day. I said that I gotta use the restroom. I just needed to piss & then get off.


    There were stalls that have real doors without those cracks down the sides but because of I figure keeping air circulating, there was maybe 1 ft of space between each one once you're inside. You can tell if someone is in another one by movement or noise. I cleaned the toilet seat then sat there to fap after I pissed. I was trying to do it in a quiet way because I didn't want anyone to know what I was doing. That's when I saw part of the leg from the guy in the stall next to mine. His jeans were all the way to his shoes on his right side like he had them off just hanging there & I heard noise like when you fap. I looked down a little just to see if I was hearing things or not & I saw an obvious shadow of him doing it. You could really see his dick & his hand going fast up & down in a shadow. He kept shaking it in a strange way like just shaking his dick around more than rubbing it. Maybe it was just the shadow but it looked like that guy had a huge dick. He then started more rubbing it to fap & I heard him move & the seat made a noise. He got up fast & stood there. You could see he was doing it real fast then & he even moaned. His stuff came out but he missed the toilet some because some was hitting the floor. For some reason, that turned me on so much that I didn't even care if anyone heard me then. I started fapping mine fast & it came so hard. It's not like I wanted to suck his dick or do anything with him or his dick but it made me so turned on from what I heard & saw that I had a strong orgasm so now, I'm worried some if maybe I could be bi sexual. I don't have anything against gays but for me to think I might be at least bi kind of worries me. I wouldn't want to date a guy so I don't know what's going on now with me. I've thought about this a lot since last year. I still get turned on thinking about that in that restroom.

    3
    # 43249 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 22

    I've been living with my dad since I was 18 and met and liked his girlfriend Jenna. When she moved in with us last year I now like her much more. My dad is 45 and Jenna in 37 and exceptionally good looking. My dad is a fireman and works crazy hours and I am here alone with Jenna often. She thinks nothing of me seeing her with only a bath towel around her and I can tell if she has underwear on with her night shirts. Its rare but over the last year I have seen her naked 7 times but only once she knew I did. When my dad works nights she is in the kitchen making cookies and cakes all the time. I go out on the back patio and watch her and a lot of times when she stoops down or bends over I know for sure she isn't wearing panties. I see her ass and vagina mostly from the rear and I sit at the window jerking off while watching her. I don't do this when my dad is home but when I know she is getting a shower I leave my bedroom door open. When she comes out of the bathroom she always only has a towel around her. If I'm lucky she might not shut her bedroom door all the way and that's when I get to see her nude. My dad is clueless about how I look at her all the time. She wears those night shirts every night after she showers even when my dad is home. He never says anything about it but we can see her nipples and know she don't have a bra on. The night shirts go down to her knees but if she bends over her ass sticks out a bit. When she sits down sometimes I can see her vagina and know she has no panties on and know she has no pubic hair. He must think I don't have any interest in her body. He'd choke me to death if he knew how often I masturbate just looking at her.

    2
    # 43243 - by Anonymous
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