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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 -
Bi-Sexual Male / 24

From 13-19, I was attracted much more to same sex. I always got crushes on the older boys. I ended up doing favors sometimes for older ones who made me feel safe. I was always the skinny boy. I wasn't a fighter & I was bullied a lot. I was the prime target no matter what because I looked so fragile. I'd given head to four other boys by the time I was 18 & all of them are straight. They only wanted to get off. They did nothing sexually in return. I had low self esteem & hated my body although, everyone outside of school said I looked like a model. Maybe in a lot of clothes, I looked okay but I was the tall, skinny, blond boy. I did have a rather large dick but I'd never got to use it. I loved how some girls were. More than just looks. I mean, that total fem quality only a female has. Even a female who is tough still has that special quality. I had some female friends but one really close friend & I thought I was gay so I told her. She didn't care. We told each other all our deepest secrets. We were hanging out together a lot. We totally loved each other as friends. I would have done anything for her. I know that was true on her side for me too.



I started to spend a lot more time with my best friend. I was staying at her house some on weekends. Her parents knew I was gay so they figured I was very safe as male friend. No sex was going to happen if we went in her room to watch movies or anything. We talked about sex a lot. She asked me what I was looking for in a guy. What did I think it would be like & would I be bottom or top or what did I think. I wasn't really sure but I had sucked dick before. It was okay but I knew those guys didn't care about me. Maybe it would be a 69 in a relationship. I didn't know for sure. I was sure I wasn't interested in anal sex though. I know it's medically not dirty & the mouth is the dirty area but it wasn't something I figured I'd not be into. My friend had broken up with her BF a while back so there I was five years ago at age 19 staying at her house & we were drinking some. Sneaking some stuff into her room. That night, she asked if she could see my dick. She just wanted to see what it looked like. I was really shy about that. It took a while for her to talk me into pulling my pants down to show her. When I did, she touched it & it went from totally soft to fully hard. I could feel my face getting red since I was embarassed by that. She pulled me on top of her & she took my jeans & underwear all the way off. She took her clothes off too. We didn't say much but I was on top of her & hard. My face was down between her tits while she was holding my dick & aiming it to go inside her. It was the most amazing feeling I'd ever had. I didn't expect that. No lube needed & it was a different type of lube feeling. For some reason, I insticivly started sucking her nipples while I went ahead & thrusted while inside her. I remember her holding my buns & we kissed. She told me she wanted to feel me cum inside her & it was okay to do that. It was safe. She wasn't going to get pregnant.



We did it four times that night. My dick just kept getting off. Each time it came, it wasn't long before it was fully hard again. I wanted to keep feeling it inside her. The next day, I woke up in her bed but I woke up with this weird feeling I'd never had. I was in love with her. I can't explain how I went from love as in friend only to this other new feeling but it happened. Since that weekend, I've never done it with anyone else & neither has she. We live together now & are going to get married in a year. We have been taking some things slow but we have a lot of sex & I really love her. I'm not in some closet or hiding behihnd her & she knows totally about me. I have noticed females & guys in a sexual way but there's no way I'd cheat on my woman. I love her too much for that. I'm not the skinny boy anymore. I'm rather muscular now & I workout a lot. None of those guys from HS would ever want to mess with me these days. I'm not the guy to bully anymore. I'm also totally cool with gay guys. I'm cool with everyone insofar as I'm not a bigot & I believe in you let people live how they are or need to. So long as no one is harming a kid or anyone else, I say leave things alone.

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# 43059 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 47

    There should be a subsection for giving into temptation. Like for instance when I was in the ninth grade and this friend had me over to his house and he got into his father's beers and he told me to drink one. I gave into temptation even if I was only 14. That kind of stuff.

    I found myself on a date with a girl, she was really a friend of mine but we went out with some other kids and when we were back at her house she said she wanted to talk so we stayed in the car with radio on. She talked for a while but eventually got around to what she wanted to say, she wanted to have her pussy touched. But don't hurt her, just touch her pussy. What a thing to ask a 16 year old. I am pretty damn sure she had never used that word with a boy before. I had never touched a pussy, I had no idea how to touch her and not hurt her, I had never even touched a girl's tits and the most I had managed up to then was to get one kiss off of Sarah at the basketball game. But she asked and I had to agree, you can't tell a girl no after she asks you to touch her pussy.

    She opened her legs and she took my hand and squeezed my fingers together and put my hand on her pussy. What do you feel? Hell I didn't know what I was feeling, all I felt were her pants no different than touching her leg. She pushed my hand down lower, leaning forward and she said to touch her but not hurt her, just touch her. After a few minutes of that she said OK maybe she should go in. That was the first time I touched a girl's pussy. That kind of temptation. But I did have more experience than I did before we went out that night. Boy you would think that after than she would be my friend for life but what happened is that she was embarrassed and she only talked to me when I talked to her. She did spread the word around that we were going steady, it would have been nice if she had told me because my mother is the one that told me I was going steady.

    But fair is fair and I told her that I wanted her to touch my dick. She was my steady so it only seemed right that she should be the one. I got my pants undone and pulled down and got my dick out and sat there waiting. I had her hand in my hand but she pulled back so hard that I could never get her hand over to my dick. Then I noticed that she was crying, sniffling really so I let her hand go and pulled my pants up. Remembering it all sort of makes those years come back to life, her name is Mary Jo and she was fourteen years old at the time and her parents gave her permission to go out with me because I was responsible. God that girl caused me problems, I was going steady with her and we had never kissed, she was always embarrassed about everything, she clung on to me if things were bad and if things were good she sent me packing.

    She was my first, or going to be my first, I gave into temptation on the night of my senior prom. That's the night you are supposed to get laid. I didn't read the manual to find out if your girlfriend who was in the tenth grade was supposed to get laid, she really didn't have a choice. I couldn't go back to my friends and tell them we had gone out, ended up at the Waffle House and I didn't get laid. So we went out to this spot that I had been told about and I got her panties off from underneath her prom dress and this time I did feel her up, touched her bare pussy this time, hair and all. Damn thing gave me an erection which is all I needed to get laid that night. I did get her laid back onto the seat of the car, I was driving my mother's 1964 Bonneville and I got on top of her when the cop hit the window with his flashlight. Nothing happened, no penetration, but she was a tenth grader and I was a senior and the judge felt that the only thing to do was for us to get married. I should have never given into the temptation of getting laid on my senior prom night.

    We got married in a ceremony at her parent's house, presided over by the county judge who married us. The preacher was there but he didn't officiate, something about not agreeing with the whole thing. Do you think anyone there believed us that we had not had sex? Not a soul, the cop had us nailed and either get married or he was going to make sure I served time for touching the poor little girl. That's what you get for dating your best friend. I got married and I had never had sex. Our wedding night if you call it that was pretty embarrassing all the way round. Her mother took her back into the bedroom and talked to her for an hour. When she came out she was dressed in street clothes and had this small suitcase with her and a letter from her mother stating that she was married. We went to the Ramada Inn where every thing had been set up in advance, Pepsi Cola in the room and flowers.

    Now I won't tell you that temptation wasn't all over me that night, it was. But my Mary Jo was so scared that all we did was lay on top of the bed and she did let me hold her. Nothing happened, nada, zilch, nothing. I didn't even get laid on my wedding night. For breakfast in the breakfast room we sat in a booth and the waitress kept hinting at how was our night. All I could focus on was Mary Jo's and her wedding rings, the diamond shone brighter than the chandelier in her house, it was my mother's engagement ring and she had it fixed up and cleaned and everything for Mary Jo. Her hand looked positively beautiful that morning. God how can one girl tempt you so much?

    I had been accepted to the University of Georgia in Athens and that meant I had to leave town and she had to stay behind and finish high school. The school let her stay enrolled as long as she wasn't pregnant. Believe me if she had gotten pregnant it would have been an immaculate conception, she was my wife by law and all but she was still not married as far as being married went. Temptation or not she was sixteen going on seventeen and God is my witness she was a little girl when it came to all that. And if I have to admit it to myself I was so in love with her that the biggest temptation by the Devil himself would never have been enough for me to hurt her. Damn I was in love, like you know you can't think of anything but her. It is a wonder I didn't flunk out of college. I won't bore you anymore with temptation and all because she got temptation herself when she was a senior and one day we just got together and had the most wonderful experience a man can ask for. I still remember that afternoon and yes I answered yes when she asked me if I loved her, God it has been fifty years and the answer is yes.

    1
    # 42997 - by Anonymous
    - Masculine Misadventures -
    Bi-Sexual Male / 43

    I AM SO HARD RIGHT NOW. I'M 43 YEAR WHO HAS HIDDEN MY GAY DESIRES. I HAVE ALWAYSto afraid. but I want swallow a cock.I have been picking 1 old friend om messenger a day showing my friends my cock an my cum.
    I just need to show the world. and I want to get fucked and fuck aa
    i. so fuck hotny, hard and want to explode. I want every make friend to fuck me. pleads I need your cock. fuck, fuck me please

    0
    # 42983 - by Anonymous
    • - Masculine Misadventures -
    Bi-Sexual Male / 34

    My compulsion has take me to see a therapist. I am and have been for a very long time a seeker of men. I don't live the life of a homosexual, I am married with a family, but I seek out men. I have gone through several stages, back when I first started I hung out where men came to look for young guys, later when I was older I associated with men I knew to like men, then I moved to where I live now and everything I do is hidden from the light of day.

    The reason I am with a therapist is that I got careless and I got caught giving a blow job to a man in parking lot. It was the security guard not a real cop and he didn't take names but he caught us, it could have been a real cop.

    I know I have an obsession and it is real. I can go for a while, maybe a month or six weeks without it, but then I have to go find it. There was a time when I hung out at places where I know men find men, clubs. But that is dangerous, you can be seen and who knows who will be there. I got cold feet and stopped going there and my source dried up. I tried the internet but all of the men that agreed to meet me wanted money. So I am back to going to clubs. Fortunately I live in a very large metropolitan area and I can go far away from where I live, I go after work and I am just looking for a quick blow job so I usually get home a little late but not real late. It is only when my wife goes to see her mother that I stay out late and have complete sex. Fortunately my wife goes to see her mother at least once a month and takes the kids (ages 3 and 7) so I have that night to myself.

    My therapist agrees with me that I am not gay, I have a compulsion, some men like whores they don't know, some men like me like anonymous sex with men.

    0
    # 42913 - by Anonymous
    - Masculine Misadventures -
    Gay Male / 47

    I went to a boy's school for disciplinary reasons. When I got to the school I was paired (roomed) with an older boy whose job was to show me the ropes and put me in my place. I wasn't going to let myself but he trapped me between the wall and the bed and after a long fight got my pants down and dry fucked me. I learned, either way I was going to get fucked, I could either cooperate and get lubed up or not cooperate and get a dry ass fucking that hurt like hell. After the first three times I started to enjoy getting lubed up and I was compliant after that and I was his for the rest of the year. I was not a disciplinary problem for any of my years there.

    That's life, if you get out of line someone is going to fuck you back into line. If you fight it, you are going to get fucked the hard way, if you follow the rules and you are compliant the fuckings are lubed and enjoyable. The thing is whether or not you think you are a fuck toy, you are. That comes with being the new boy on the block or the new guy on the team, you get fucked and the big dog does the fucking. It was the most important life lesson I learned.

    I am not a big dog, never was. I was a shit head when I was a kid that is why I got in problems. I found out that my place is being the fuck toy, I am just not the Alpha dog. When the Alpha dog comes by you drop your pants and adopt the position, makes life worth living. Life is just so much better when the Alpha dog likes you.

    2
    # 42874 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 39

    Three years ago my girlfriend Regina moved in with me along with her twin daughters Martha and Mary who both turned 20 years old last Friday. Regina is 42 and hasn't had contact with her x husband for 6 or 7 years. Her daughters who have angelic names are not at all, both of whom smoke weed constantly and I suspect other drugs like oxy. Regina and I get along well most of the time and she does work 5 days a week. Her daughters are deadbeats and the only one who works right now is Mary at a Taco Bell part-time. Regina has no problem with the weed and does it herself along with her daughters and I confess I smoke it also a few times a week along with the booze and beer we drink. For the first year or so it was done on the sly by the girls and Regina but has developed into a kinky relationship which Regina has never tried to stop. The girls wear clothes and night close around me that are very revealing and its common now for me to see them naked during the week and more so on weekends. Regina is a waitress and works most weekends a month and it seems the girls do this knowing I can see them or are to high to care. I never have any sex with them but am able to see them in various stages of undress most days. Now neither of them are what I would call beautiful but both are attractive and I do get aroused seeing them. Well over a year ago most of the time when I had smoked weed or drank to much I also began exposing myself to them. I think nothing anymore of going about with a towel around me after I shower and go in and out of the bathroom naked knowing one or both can see me. Regina knows I have seen the girls naked many times and knows they have seen me. She has never once ever objected to the way things are in my house now. Martha is the one I have seen masturbating I think more than a dozen times and Mary I have only seen her doing it once. When Martha masturbates with her door open its always on weekends when Regina is at work and I suspect she does it for me to see her. I have jerked off watching her many times and twice I jerked off in the hall outside her room. Other times I was in the hall naked with a hard on and know she saw me watching her. I began jerking off in my room with the door wide open know both were outside but again only when Regina is at work on weekends. The longer this goes on the more blatant is has become and nudity around each other seems to be no big deal. Martha has asked me why I jerk off if I'm screwing her mother and I just laugh anymore and tell her I only jerk off when her mom works weekends. Mary never says much but Martha has told me I have a nice ass and said a few times she likes seeing me nude. A few months ago she told me she loves seeing me with a "boner" and that's the word she used. Some weekends when Regina comes in from work Martha will tell her she saw me naked. I would think most mothers would not like hearing that but Regina only shakes her head and says nothing about it.


    For a long time now I hardly ever get dressed on weekends and am either in my underwear or my terry cloth bathrobe and never bother to use the tie strap for it. I see Martha naked more often than Mary but neither one of them has ever shown any sign of embarrassment around me and quite the opposite. Regina is also fearless about exposing herself but not nearly as brazen as her daughters. I suspect Martha is more involved with drugs than Mary is but both seem to be in a daze at times. I've seen them taking pills many times but they hide them all the time and I don't think Regina knows how much they use. I don't think Martha ever wears a bra except maybe when she goes out. When she wears night gowns she never has panties on either. Mary is almost the same way but sometimes wears a long button down shirt that she doesn't bother to button. When she wears this I know she is high on something since her breasts and vagina are on display. Even when Regina is home I never bother closing my bedroom door and the girls don't seem to care if their mother sees them naked or close to it. I can't understand the way Regina reacts to all this knowing I see her girls naked and they also see me like that. Last month Martha who is the loud mouth of the house told Regina she saw me with an erection and that I have a cute penis. Admittedly we were smoking weed at the time but instead of Regina being mad hearing that she just laughed it off. My house is a one story ranch with three bedrooms and one full bath. Both girls have their own rooms which are across the hall from the master bedroom. It used to be the girls who didn't shut their doors but since I've become accustom to all this I hardly ever shut mine until I go to bed at night. I doubt a day goes by without me seeing one of them naked or one or both seeing me naked. When I think back now the only reason I let Regina move in was because her x stopped paying child support and she couldn't find out where he was. If I said I didn't like the way things are I'd be lying. I know Martha has a boyfriend although I don't know who he is. Mary doesn't seem to have one and they don't seem to have to many friends. Martha is outspoken with everything and Mary is the opposite and quiet most of the time. It was last year Martha began shaving her pubic hair but Mary never has so far. A few times Martha has mentioned to me that the reason she shaves is because her boyfriend likes it like that. I don't think she has told her mother that but she has no problem telling me things like that. She has told me she uses tampons and once asked me if her boobs were big enough obviously knowing I see them often. I wonder sometimes if she is a little on the crazy side. Mary never asks or tells me anything but nonetheless has no problem seeing me or having me see her naked. When they moved in here I never expected how out of control it would become and were they always like the way they are now. Part of it has to be because Regina has never objected to anything. Just last night I came out of the bathroom after my shower. Regina was sitting in bed and I stood there naked drying myself off with the door open and Martha sitting in bed across the hall watching me. Regina knew Martha was there but never told me to shut the door. Hello is it me or does she just not care about any of it.

    4
    # 42863 - by Anonymous
    100 of 40,940 Confessions Displayed.

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