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 / 44

I met her in college in my last semester and she was anxious to get married. We got married right after graduation and went on our honeymoon. We came back after a day because she was unable to allow me to complete the act. She was very distant after we got back and I slept on the couch of our one bedroom apartment. No explanation given.

Several months of this and one night I am out with some people from work and I get close to this girl in another department and I end up at her place and we have sex all night. She is not uptight about it. I go home in the morning to shower, shave and get ready for work. I confess to my wife and tell her that she has to go see someone because either she puts out or the whole marriage thing was over.

But nothing happened, five years of nothing happening. In the meantime I am going out with various women, some not so nice other very nice and getting my sex that way. My wife is still a virgin and spends her time crying but does not put out. One night things get very heated and I slam her and fuck her. She gets pregnant from that one time and all her family is so happy she is pregnant. She goes through her pregnancy has her kid and she does the stay at home thing and does not go back to work. One kid is not enough and I tell her that she needs to have two and this time she just gives in and puts the pillow over her face and she gets fucked for number two. In the meantime I am fucking whoever I can.

I fuck this one girl and I tell her about my wife and she wants to meet her and I bring her over, my wife might as well meet one of the women that is putting her pussy on the line for her. After them spending a couple of hours together my pussy girl tells me that my wife is just one of those women that doesn't fuck. It is not in her. Shit, now what? and I never questioned my pussy girl, I just fucked her all night. My pussy girl gets to be friends with my wife and she tells my wife that she doesn't need to be ashamed, it happens and not all women like to get fucked but that she can still be a good wife and take care of her kids. My pussy girls spreads her legs and says fuck me instead.

This time I fuck her and fuck her and fuck her, I am so pissed off, so fucking angry at my wife and so I just fuck the shit out of my pussy girl and she tells me if I keep that up she is going to get off the pill and get herself pregnant. I fuck my wife right after that, another one of those arguments and I fuck her and she gets pregnant again. She doesn't fuck but she is fertile as she can be. Now my pussy girl does get serious and decides to just flush her pills down the toilet and dares me to fuck her.

On the one side of my life is my wife who won't fuck and gets pregnant and the other side of my life is my pussy gil who fucks all night and I have to fuck her for a year after she goes off the pill to get pregnant. My pussy girl gives me pussy but she won't do all the rest and my wife does all the rest and won't give me pussy. I am 44 and to say that my life is complicated is no lie. My pussy girl wraps her legs around me and my wife keeps them shut and they are both happy in their own way and somehow get along.

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# 43604 - by Anonymous
    • - Masculine Misadventures -
    Straight Male / 51

    Unlike the vast majority of kids who were in my freshman class in college I was 23, I had spent some time dealing with issues far away overseas and many months in a hospital on my back. These kids seemed like high school kids to me, just as stupid but just as nice, the boys pretending to be men and the girls sporting naked boobies under their Mexican blouses. I sat and watched, I was not one of them.

    I met this one girl, Sandra who was 17 and she came from a typical home of three kids and teacher parents, real middle class and she still lived at home. She must have liked older men because she got close to me and like gum on your shoe she stuck. We walked to and from class and one day she brought me shirt she had embroidered with all sorts of Peace and Love. Believe me, not the shirt you give to a guy who had been doing things that were anything but Peace and Love. But I took the shirt.

    When I asked her to come to my apartment she came. I tried taking her top off but she fought and then relented and too it off herself. Same with her pants. She sat on the old semen stained couch and I told her that I was going to fuck her so if she wanted to leave she should leave. But she didn't. I pulled off her panties before taking off her bra, she had a very thick carpet of hair, when I got off her bra she had nice looking tits with rosebud nipples. I stood in front of the couch and kicked off my shoes and dropped my pants and stood there in my shirt and hard dick straight out. I took off my shirt and told her to open up and her legs came open and I got on top and fucked her.

    We had been in class less than two weeks. She was going to be my girlfriend no matter what. She came over to my apartment between classes, if I was there we would fuck or mess around, if I wasn't there she would straighten up. She did laundry and washed dishes and took out the trash. She fucked, she sucked cock, she took classes, she got good grades, she knew how to grocery shop, and she liked to fuck. For a new freshman with need for a woman she fit the bill. When I say we fucked, we fucked as many times a week as we could, and as many times a day as we could.

    Her parents were too thrilled, they disliked me and didn't trust me, they were teachers who hated anything that had to do with what happened over there and they had no desire to have me at their table, knowing what I had done. So we hardly ever went there, we went to my apartment to fuck.

    It was when we were Juniors, by then I was pretty much set into a degree in Industrial Engineering and she into Elementary Ed that we met Katia who was a Veterinary student. It was by accident really, but she hung around with us, she was short about just so high as Sandra, she was a little darker and she said her parents were Greek and she was from Tennessee and she always liked horses. She worked at the campus bookstore and that is where we met her. She and Sandra hung out and Sandra would tell me that Katia took care of the horses and Katia had told her about how one of her jobs was to wash the penis of the horses. Really? Could she be telling the truth?

    Well one day she said she would take us out to the horse barn and there were seven large stallions in their individual stalls, she said they were all breeding stallions and the College would rent them out for stud. She opened the door to one of the stalls and patted the horse and talked to him and then she ran her hands down his flank and under his belly and started to rub his sheath and the stallion let out his penis and she kneeled down and massaged its full length back and forth with both hands and the stallion stood there enjoying the moment. I had never cum in my pants but I did that day.

    Katia never told us whether or not she did more than make love to the horse penis, but she did show her affection for Sandra one day and when Sandra rejected her she got upset and left. It was many weeks before Sandra convinced her that she didn't reject her personally it is just that she had not expected to be kissed by her. Katia kissed Sandra, and Katia caressed Sandra, and Katia got in bed with Sandra, Katia showed Sandra how one girl could make another girl call out her name, Katia showed Sandra that loving a penis and loving with a girl were not mutually exclusive. Katia took Sandra to heights she had never thought she would experience. Katia could eat pussy and take a dick at the same time. Katia wanted both, and lots of it, she couldn't keep her hands off Sandra and she wanted to be fucked often. And Sandra learned or came about to the point where she liked making out with Katia and took a dick when she had to, but she really never turned it down.

    We finished college and had to move on, I got a job at a manufacturing outfit and Sandra taught at the elementary school, Katia stayed to finish her Vet program and moved down after she was done. Those hot days of college subsided to long nights side by side, the girls in each other's arms but if I got to wanting some pussy they always obliged. It was hard for me to recognize one day that I was the odd man out, this was about them, they had gone from experimental lovers to full on lesbians who did their best to please me. Katia has never lost her phallic obsession, collecting phallic objects from around the world, Sandra taught Elementary school all her career and I started and ran my metal working shop. Try as they might they just could never get back to where I was the center of their attention, I was the one that kept them in good stead providing them with financial security, I was the man, but they were about each other. It is still sometimes hard to wait in bed as they walk around with their naked breasts about to come to lay beside me, knowing that after they help me settle down they turn to each other and I am relegated to a pillow in my arms thinking about those wet days when I had nothing but a rifle to hug.

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    # 43599 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 51

    I guess in a way we all want to have that one experience where we are not in control. Well it happened to me. At the time I was into traveling to far off places. On that trip I went to Peru. Once in Peru I heard that you could take one of the supply boats that went up and down the rivers as a paying passenger so I flew to Iquitos and found this boat that was went up river to supply the mining and oilfield camps. The fee was nothing really and I got on at dawn and I was assigned to this small room with two bunks. In the other bunk was an Englishman who was going upstream to one of the camps.

    We chugged, because that is all the boat did, it chugged at about two miles an hour upstream, after a while we had left civilization and we just kept on chugging. I found a spot on deck where I could read and I sat down to read the same book I had brought with me. The crew was basically a captain who was the owner of the boat, a crew hand and the man's woman who cooked and cleaned. Sleeping on the bunk was hard, it was stuffy inside so I stayed outdoors on deck just watching the rainforest slide by. Late evening after dark and all hell broke loose. There was yelling in the local dialect, the woman was screaming and the captain had the Englishman against the wall of the deckhouse with a machete.

    Between the deckhand and the captain the Englishman was tied to the railing and the woman took a large knife and she cut off his penis and threw it into the river and then the captain took a pair of pliers and pulled his tongue out and she cut off his tongue and threw it into the river. He was bleeding profusely and they left him tied to the rail. I took some of his clothes to try to stop the bleeding, he passed out and fell as far forward as the bindings allowed. In the morning he was dead.

    His body was thrown onto the ground of the next village that the boat came to in the morning, there were a couple of army people and that was that. The boat continued up river and I got off at my destination late that evening.

    Move forward all these years. I am now an old man, well old enough to have severe problems with getting an erection, and if I do it lasts a minute or two. I get frustrated because it is obvious that you can't have a woman and keep her happy in that way, but mostly you can't keep yourself happy because even without a boner you want to fuck. I have spent my life active, hiking and biking and this boner problem plagues my mind. Until I remember that Englishman who had his penis cut off, at least I still what's left of mine, useless as it is.

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    # 43579 - by Anonymous
    • - Masculine Misadventures -
    Bi-Sexual Male / 48

    hi everyone I want everyone to know who i am my name is Cassie H. i live in lakeland fl i am a crossdresser on hormone therapy male to female and i love it i have sex with men i suck cock and swallow cum i take in my ass and love when the men exploded in side me i like get spanked when we make love not into rough stuff or condoms love to have a men put his cock inside me and stroke me slow and easy and very long time i love when they are very thick i love to be stretched to my limits i have more womens clothes and heels makeup i love to go out in public i get all kinds of looks but i dont care what other people think i am who i am i feel more feminine everyday and more like a women you all may think thier is something wrong with me there isnt i am just a women trap in a man body but the women is coming out more everyday and i love it i wish this was public i would put my email on here so maybe men would want to contact me i love what i do and who i am i am Cassie Harsh a crossdresser from lakeland fl.

    1
    # 43569 - by Anonymous
    - Masculine Misadventures -
    Straight Male / 37

    Personally I don't think women really get it when a man has an erection. We don't care what you are saying, how you are saying, what you think you are saying, we want to fuck you and that is all there is to it. To paraphrase Tarzan You pussy, Me dick. Enough said.

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    # 43541 - by Anonymous
    • - Masculine Misadventures -
    Gay Male / 21

    I'm a predominantly gay male. How I know it is just like a straight guy, you're the orientation of that gender you can feel romantic & want a lasting relationship. Sex acts don't always mean I orientation. I had two different BFs since I was 15. First was at 15 then when I was 16 & that one lasted 2 yrs. I was a good kid. I never got in trouble or did any type drug. I never had hookups either not that's bad. I realized early what I had going for me & all the things against me. I had a lot against me. My family was lower mid class no college. Money was always hard but no one ever took welfare. They'd live on a street before that. Both parents worked long hrs. My dad did construction 60 hr weeks outdoors in hot or cold. I did terrible in school. I have a slight learning disability & math comes hard. My spelling is bad. I tried hard at times but I'm not college material. My IQ actually scored 130 when my parents took me in to find out what was wrong but this learning disability seems to drain any IQ but I come up with great ideas others don't so it's all strange. Anyhow, on a positive side, I have well above avg looks. I'm the tall guy with the good looks & I have a big penis. Looks won't last forever & after 40 or 50, I hear, there is ED or other problems that start for a lot of guys so it's now or never imo. This is why I started escorting. I was told I might get good pay in modeling but it was going to take time & I wasn't going to do porn videos. Too much of that is all free anyhow. I learned fast at 18 that in porn, guys get paid a lot to do with other guys but in escorting, it's often opposite.





    My first escorting date was a 55 year old woman. She looks very good for her age. She has a LOT of money as in tens of millions. She didn't want to go alone to parties or places to eat but she wanted a hot guy with a background screen who isn't on something or anyone arrested. She also wanted STI status. Place I worked with is harsh in screening but that's good. She liked me instantly. I liked her too. I got many callbacks from her but it was NEVER sex. Just go out to parties or where she eats at expensive restaurants etc. I was to be as 21 at parties then order a coke or something elsewhere but play as 21. She knew I was 18. She'd done that with other guys but she really liked me most. I found other women similar to her who wanted about the same thing up all night at glam parties as the date but it wasn't sexual other than a kiss, dancing & holding in front of people. I was making BIG money. More in a night than my dad made in two weeks. I was happy with that. I was having fun & although I didn't think I'd ever want to do it with a female, a few did rub it through my pants making it hard. I think any guy gets hard no matter if gay rubs straight or whatever unless you're like really old 90 or something. My work went like this over a year. No sex. I was too busy working to date any guy but I saw lots of very hot other guys when I was working. I could tell some were gay. Others, I wasn't sure. I did & do want that forever relationship of romance, love & total commitment with some good sex but I figure it can wait a few years while I work while I can. I'm very good at what I do so there is no learning disability about that. I'm an honest type person not criminal type so it's just who I am & that comes off well imo. I don't try to scam anyone. I'd not do that. I know what being hurt is. I'd not harm anyone. Just last year on my job which does say NO FULL SEXUAL ACTIVITY. That means no penetration & also to get them to not go for any sex. That changed one night. I was on a date with a lady who was 62. She can pass for 42. She can put most 22 yr old to shame. She has massive money. Her husband divorced her & he's famous per acting. She got a lot. I was hired 600 for the night just to party some & out to eat etc. Yes, that is $600.00 for a date with no sex! It can last up to 12 hrs. She got me drinks from server at table then at the party she had me drink. I could feel it. She rubbed my penis under table. It got hard from that. She told me after date, she wanted me to make love to her! I told her I can't per the contract with place & what if I was gay? She said I'd not be on their hrs & any such things as gay, bi, straight. It's humanity & we are all sexual creatures. I never thought of it like that.




    That night, I went to her mansion. I ended up sleeping a while because her servant aka assistant who tends to house gave me more drinks. I woke up in her bed with my pants down. She was in bed smiling & telling me things of how I looked & she held my penis. It got hard. I ended up doing it. It went three times inside her over an hr of it. It felt good but she was in love. She gave me $4000.00 in cash as I left & wanted me back four days later to go out! I got paid from my agency too. She pays them & they pay me. I know, that's prostitution but she told me marriage means legal prostitution & for me to take a look at Trump & his wife then ask if his wife is a prostitute or loves him for his age & looks etc. Of course, we all know answer to that one so I guess, marriage is often legal ways of what I'm doing. I've been doing it with this woman for six months & now she wants to make it LEGAL through marriage.




    I'll be giving up a relationship based on my orientation & the love that comes from it but I do love this lady in another way & am having fun so I'm getting married in May! She knows I want a life of money. I haven't lied about that.

















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    # 43507 - by Anonymous
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