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Crossing The Line, My First Time, Last Year At The Ripe Old Age Of 53

I am now in my fifties and have harbored a long desire to try gay sex with the right man. I have always been attracted to males, I say males because it has always been a same age thing. My first desire was with a boy in the fifth grade. But acting out on it is another story.

Let me say that my desire is manifested by wanting to kiss a man. Long before I get to the point of trying something more intimate, which I am totally open to now. It was that desire to kiss him that I felt all these times. Lately it is a man I know from a social circle thing, he is a carpenter and concentrates his activities on remodeling kitchens and particularly men's dens or man caves, That's how I spoke with him. Bringing my den into the 21st century. The desire to kiss him was so much that I had to curtail my contact with him.

I got a flyer in the mail, one of those personally addressed to 'occupant'. It was a flyer for a cruise company. I read it and tossed it out. I had never been on a cruise. I'm single so cruising seems so much of a family or couple's thing. I read a couple of blogs, one in particular about this lesbian woman who cruised because she said that more often than not she met a fellow female traveler and she hooked up with that female for the cruise. Mostly a friend's thing, but not always, many times it was a woman looking for some romantic fun as she was. It was on that blog posting that I read about gay friendly cruises.

I started to do some research and found this one cruise for a week in the Mediterranean, Barcelona, Ibiza, Palermo and Malta sort of thing. All places that I had read about but had never been. And it was gay friendly. I booked the trip, more money than I had ever spent on a week's vacation. I was determined and carried both anal lubricant that I use with a dildo from time to time, and condoms. A friend would be nice, but a romantic friend would be better. I was determined to cross the line and act out what I felt.

The first night was overwhelming, the clubs were filled with gay men mostly and some gay women dancing and getting drunk, Frankly to me they were over the top and to use the now favorite word, 'toxic'. What a turn off. I ended up at a bar up on the top deck sitting alone nursing a drink. The waiter was very talkative and he was pretty obviously gay and he asked me why I was alone. I said 'what the hell' and told him I thought this would be a good way to meet men my age. He laughed, a little. But it opened me up to being open about it and we talked and he was open about being gay himself and he suggested that I sign up for a table in the dining room with pot luck partners.

That's where I met Josee, from I don't know where. Like me he was more my age than those young snobs in the clubs and we got to talking. He was a licensed art dealer, I found that in Europe you have be licensed to do anything. We talked about art, I like it but I am no way a connoisseur of the stuff. He wasn't either, not really, he sold stuff that tourist like and he went on these cruises to get away from his small shop. We stayed after dinner with a drink and talked, then onto the deck for a drink in the moonlight. I was so attracted that I reached over and said 'I hope you don't mind' and I kissed his lips, my very first time.

He didn't mind and we ended up in my cabin and I played out what I had only read about and scene on the porn sites. But not porn like, mind you. He was very seductive, his hands were so smooth, a man who never touched a screwdriver, much less worked with his hands. He was thorough, he enjoyed every minute of it, and so did I. At last I told myself I'm doing it. He excused himself way after midnight and he disappeared of the ship. I didn't find him again. I was hurt, really hurt. Back to my friend at the bar. He told me that some men come on board for money, they are professionals, and I wasn't a paying customer. Don't take it personally.

That was my one night, the night that I crossed the line. The night that I truly kissed a man, the night I held the penis of another man, the night a man took my penis in his hand and then his mouth, the night I first had a penis in my mouth. I have to say that a very erect penis in your hand is a feeling that can't be replaced, a dildo won't do it. And a very erect penis in your mouth, well that's what it's all about. I never used my lubricant or condoms, not on that trip. That's a story for another time.

  • Panties For Step-dad

    I know that my step-dad has been sniffing my panties because I kept finding they had moved a bit - like I'd leave them on one side of the bathroom but they'd move a few inches.

    It's either him or my mom which would be ick but if it's him I don't mind. He's nice to me and mom and I find is quite flattering as I'm not cheerleader hot or anything.

    So I've been making sure the ones I leave for him to find smell nice.

    I don't want anything to go further and I move out in a couple of months but I'm toying with the idea on my last day letting him know that I'm ok with it? IDK maybe that's a dumb idea lol

    Ashamed That I Was A Sexually Aggressive Youth

    I accepted I was gay at a really young age. Single digit age. I didn't tell people or express this openly, but my thoughts and actions were all... complicated by this. Specifically I was obsessed with lude sexual acts at an age where my cognitive faculties were lacking and I was not equipped to make good choices.

    I also had my own computer, high speed internet, and a door that locked when I was MUCH too young for all of those things. I got really addicted to internet porn (especially cartoons, go figure) before junior high.

    I wasn't conflicted about being gay, which I knew was fine. I was conflicted about being kind of a perv. I was super preoccupied with boys with big asses. I was a relatively bright youth (good grades, advanced classes, talented and g*fted program TAG) - but I really didn't have empathy or emotional intelligence yet. Cleverness without a conscience and a very mature sexual appetite was a bad mix. I came up with ways to barter for sex with other boys while managing to 1) Not get caught 2) Not even necessarily let them think I'm gay 3) Convince them they wanted it too. Now, I'm not defending this behavior, but do understand all these instances were consensual in the moment and while we were too young, we were all around the same age.

    "uh oh I like boys, maybe I wanna kiss one someday." Is a normal struggle for a gay preteen. My struggle was, "I want to lick that dude's stanky asshole."

    Of course I also asked myself "WTF is wrong with me? Do you have any idea how gross that is? Maybe gays are evil and gross." Granted, I didn't know that 10 years later ass-eating would be hella in style. I just thought I was the one demented faggot who wanted this, maybe due to a rare mental disorder?

    But I wanted some man ass so bad that I took small risks to find out if and when it could be attained. Over the years, a few boys just outright agreed to the idea of sex. One of them I think was gay and he was almost too eager, another was straight and frankly kind of a little psycho who just wanted to hump some ass cheeks. I remember hating him but liking the idea, "Oh, now I'm the one being pursued." However, there were others who shockingly didn't jump right on the butt stuff bandwagon I proposed.

    This is where my behavior was regrettable. At the time, it did not occur to me that I was basically tricking these guys into what could be a lot of emotional turmoil later. Most of them were straight but willing to "trade" for it and that seemed like a perfectly reasonable transaction to me. I first got the brilliant idea of basically introducing prostitution to my peers the day I got a really rare pokemon card in one of those random packs. I didn't like pokemon (I know, that's almost worse than the sexual deviant thing) but this other boy who definitely wasn't interested in letting me go to town on his rump wanted that card a lot. There was a lot of negotiating and I firmly remember arguing for a certain amount of time for the sex. Like, "It's gotta be at least 10 minutes." Well, when it actually happened I was so overwhelmed that I sure as fuck didn't last 10 minutes. Our friendship vanished immediately afterward, too. Neither of us could look at each other and this is what usually happened.

    Pokemon cards were a common one. I don't remember how many times I traded those. I also gave one kid a really nice bike that I had saved up for the better part of a year in advance with the idea I might get to fuck a particular bike-needing individual. I did. It lasted a couple minutes and immediately destroyed the otherwise innocent friendship and left me with a lot of shame and confusion. However, as soon as the urge was back, I was masturbating to the memory of eating his ass in the woods around our neighborhood. I really started to hate myself because I knew I would be unhappy wanting it and I'd be unhappy if I got it.

    I also pawned a sizeable anime collection to another boy I knew was straight but sexually charged enough that he could mentally cope with the arrangement. 4 anime series in return for as much sex as I wanted that night - which became a ridiculous roller coaster for both of us, changing our minds numerous times each. We first exchanged oral sex. Both finished, which was unusual. Both disgusted, and he has to take the anime and get out of my sight. But an hour later I wanted it again and our contract was still running. I snuck over to his house in the middle of the night and we had sex a few more times.

    Finally, and worst of all, I once convinced a classmate that I had a gay demon controlling me, that gay sex would get it out of me, and if he helped me I would be cured and would finally go to this youth worship thing on Saturdays as he wanted. We went into a sport shed by the track and I got cum all over his shirt. It was bad. He freaked out, started crying. I had to sneak him a shirt from the Lost and Found... and I never went to his church thing. I am so ashamed. Never really told any of this.

  • Just Confessing About An Important Aspect Of My Life

    I've been exposed to porn from a young age so i more or less understood really early what sex and all of that stuff meant...so before i even turned 13 i was completely aware of sex, pregnancy, contraceptives and that i really shouldn't let a guy fuck me until i'm older because of all the pregnancy stories that scared me lol. But...... i also became pretty addicted to porn and have always touched myself too much. Now that this detail is out of the way, i am a muslim girl but not a very religious one so what that means is that all the boyfriends and a fwb i've had i let them have sex with me but only oral and anal. Sooo yeah up until now i've always had anal sex and kept my vaginal virginity somehow (for my future husband). Weird time to confess this but it is what it is hahaha

    Wanting A Cock For First Time

    I am a happily married man to a wonderful wife. I don’t know why I want another man’s cock. I want to stroke it run my tongue up and down the thick shaft. I jack off thinking about sucking cock and having another man shoot hot cum down my throat. I wish I could be on my hands and knees and have a big cock buried deep in my ass and just fuck me hard. I want to feel the hot cum squirting in my ass. Like I said I don’t know why never have done anything like this but I sure want to try.

  • My Husbands New Camera

    I never allowed it before, but my husband has always had a problem with me not being as willing and sexual as he is. I really try to change and do whatever he wants. He got a new camera and quite unwillingly on my part I posed for pictures nude. That was one thing, but now he's going further and further. He takes pics of me when his cock is in me, my vag or mouth, even in my butt. I try to hide my face when I can. He makes me spread my legs, then reach down and spread my lips down there so the picture is of every part of my pussy. He even takes pictures of me with cum leaking out of me, and on my face, or boobs, even in my butt. My butt sort of gapes open after he is done for a while, and he took pictures of it that way, with his cum resting inside me back there.

    I had no idea how loose it looks. I look like a whore in these pictures. Now worse, my sister asked if I'd posed for him, then showed me some wife sites where men post naked pictures of their wives. I'm all over these places, and so many men make vile comments, and he writes back telling them everything I will do sexually.

    I'm at my wits end, but don't want a divorce, but I'm not a whore, except what I thought was in private for him

    Saving My Cousin Toni From A Lifetime Of Sin With That Girl El

    My cousin Toni was a year older than me. But being the two that were closest we hung out a lot. I got into her pants and popped her cherry when she was sixteen. It was always something that she held over me. She didn't date much, she mostly went out with groups, movies and stuff. But once in a while I took her out, when she wanted to be somewhere without all the other kids hanging out. Mostly movies she wanted to watch, girly movies with tears and Kleenex. If I didn't want to go she reminded me that I owed her big time for letting me pop her cherry in the ninth grade.

    She was the rich one between us both. Her family had several electronics stores, sold TVs and stereos and Radios and fixed electronic things, toasters and washing machines. I spent a couple of summers there learning how to pull a toaster apart. We were the poor ones, my parents were both teachers so you can imagine we were poor but not destitute. Not like my cousin Toni who got a car when she turned seventeen.

    Throughout high school she was the one I went to when I needed relief. Mostly she gave me hand jobs, but a blowjob played in once in a while. Sex, outright intercourse, happened seldom, but it did happen. She said she couldn't understand what I liked about it. She went to college to this small liberal arts school to study art. I went into the service, fallowing in my family's footsteps. Spend a couple of years in the service and then the GI Bill and you get your college out of the way. I was in the service when Toni showed up with a girl named Elvira, El for short.

    Elvira was from one of those families in Connecticut, rich. Her father owned a bank. El was tallish, taller than Toni my cousin. Blonde with deep blue eyes, she said that her folks came from Norway. Toni like me was a little bit darker, we had Italian roots. Let me comment on El's tits. She had big tits. Not like Toni who followed the women in our family, small but nice tits. Just enough to get a handful, but not hanging there like a couple of jugs. El had big tits and that was her nickname that time she came to visit 'Big Tits'.

    Like I said, I was in the service that time El showed up. I was on leave and I was hard up. The Service doesn't provide much opportunity to get some warm pussy, it's mostly you and your five fingered friend Manuel. I wanted Toni to give me relief. I needed Toni to give me relief. Toni refused to give me relief. Something about El. She and El were good friends she told me and she thought it inappropriate for her to behave like that with me when El was there. Fuck El, I told her, fuck EL. I need to get off, I need you. And I did, being turned down made me mad.

    But Toni kept insisting that El didn't think it was right for her to be close like that with her cousin. It also slipped out that El was more than a friend, Toni told me that they had been playing around, and she liked it. That's when I put my foot in my mouth, I mean put my foot down. Fuck El, I need you to be nice to me right now, I yelled at her. She did, but not nice about it at all. It was only after we were pulling up our pants that she told me that she and El were an item. Like an ITEM, they were messing around together. El was a lesbian and El told Toni that Toni was also a lesbian. I'll be honest. I had heard of queers and gays and homos. But I had never heard someone actually use the word lesbian, much less claim to be one.

    When I was discharged from my two year commitment I went straight up to that college, where Toni was a senior, and I put Toni in the car and drove her home. I was full on 20 at the time and I had to put my foot down, and told Toni that it was either grow up and get married or else. Marrying your cousin was not necessarily against the law, as long as you had different last names no one asked. We got married at the Justice of the Peace, just the two of us and the witnesses at the court house. Basically we eloped. And that in a nutshell is how I saved Toni from a lifetime of sin with that girl El.

    Love Giving Bjs

    Ever since I gave my first bj in high school I’ve been addicted to them. I love sucking on a guys dick.

    I’m not really sure why. It just feels kinda powerful to me that I can take a guys dick in my mouth and make him cum in less then five minutes. I always swallow too

    Won’t say how many dicks I’ve sucked but they were all different sizes. Different cut status and the hairiness varied by the guy. Love holding a guys balls as I suck him.

    Since I was 20 I’ve secretly been sucking my dad’s friend. I honestly don’t know how I ended up giving him the bj the first time. Pure luck I guess but it’s definitely our secret. He’s got a big uncut dick in his pants. He used to have a bush but started shaving it off when regular head became a thing. I have no intentions of fucking him only sucking him

    3 to 4 days a week I’m usually giving head to someone

    My First Wax

    I was on the school swim team throughout middle and high school. I was in really good shape from swimming and obviously a good swimmer because of it

    All guys had to wear a speedo. Took some getting used to but eventually it was like second skin. Girls at first thought they were funny but ended up liking them. We still felt so exposed because there was no hiding our bulges

    As puberty took over pubic hair became an issue. Some of use just shaved the hair that poked out. Pretty much a bikini line shave. While others fully shaved all their pubes off

    I kept my pubes squared off. I shaved every other day. My bush was shaped so that it didn’t poke out the sides. But then I was going to state competition. Instead of shaving my mom suggested I get waxed. A local salon was offering to wax all of us in preparation for the state meet

    Plus my mom got waxed there so she asked when she went if they’d wax me.

    So I went there a week before the state meet. Walked back into the room Wgwre waxing wax done. I was instructed to take off my pants and underwear then lay on the table.

    So I hung my pants on the hook on the wall then hung my briefs on the hook next to it and there I was all exposed. I got the biggest boner! I felt so embarrassed!

    But she started the wax telling me it’s fine. But boy was I not ready for the wax!

    But afterwards I always got waxed I haven’t had pubes since high school and dont think I ever will, I get waxed every 8 weeks. I’m always bare down there

  • Sucked My Way To A Better Grade

    When I was at school doing my AS level coursework, I needed at least a B grade on this one piece of work to pass, but my teacher gave me a C so I hatched a plan that I'd guilt him into changing it by flirting with him loads and basically chancing my luck that he'd do it just to stop me flirting.

    Mr Jones was mid 40's, a bit chunky but not like fat fat, and he was always friendly to the girls, so I passed him a note asking him to ask me to stay behind after class, which he did. So after everyone else had gone he asked me if it was to do with the grade and I said yeah, and we talked about it and I was laying the flirting on thick, bent over his desk with a skirt on showing my legs, getting super close to him and he was getting super uncomfortable. So I asked him if there was anything we could do to change the grade and he declined, so I got closer and asked again and he declined again, but I could tell he was catching on to what I was saying. So I was saying how I was so looking forward to getting a B and undid my shirt slowly.

    He told me to stop it and that he didn't want to see me, but I was kinda evil and asked if he was calling me ugly and didnt he like my boobs. He was stammering all the excuses so I walked around his desk and slipped my leg across his lap, straddling him. I leant in and whispered that maybe we could work something out and I felt his hands slide under my skirt to my bum.

    I asked him whether he'd change my grade and he said after and crushed his face into my chest, scooping out my boob to suck on. I like never expected it to go this far but I had flirted myself horny and having Mr Jones sucking on my boobs made me even more.

    Do you want me to suck your dick, Mr Jones, I asked as he shakingly undid his belt and pulled his trousers down. He had a nice dick - not big, but clean and it smelled nice, so I sucked him until he came in my mouth, his hand on my ponytail.

    When I looked up I could see the terror in his eyes as he realised what he'd done. I'd never meant it to go that far but we'd both got caught up in the moment. He hurriedly pulled his pants up and was stammering and everything about not telling anyone, so I was like I held up my end of the deal, do I get my B and he changed it on the system in front of me. So I chanced my luck again and said that I hated homework and that I didn't think I should do any more this year and he agreed straight away.

    So that's how I sucked my way to a better grade and no homework for a year.