Adult Confessions

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Did your date bring along an ex to your dinner? Was your date required to blow into a breathalyzer to start their vehicle? Did your date ask if you were in a "serious relationship" in under 15 minutes of meeting them? Did you hit the friends zone, without even taking the field? Did she have a machete hidden in her purse? Was your date fresh out of prison for murder? This is our category for confessing your real life cringe worthy dating disasters.

- Dating Disasters -
Straight Female / 21

Spring Break Mistake

Last spring break me and my best friend went to Daytona for a week. Getting laid was definitely on our list of things to do. One afternoon we were already pretty drunk at a beach bar. Two hot guys were buying us drinks. When they asked us to go to their hotel we said yes. But when we got there the surprise was, they only had one room, double beds. We looked at each other and said why not. We were both in the middle of getting fucked when the guy doing my friend yelled "switch". The guy I was fucking hopped off the bed and jumped on the bed with my friend. The other guy got on the bed with me. And we actually went along with it. The guy began fucking me and started squeezing my tits. He "out loud" said something about my tits being huge. The guy fucking my friend replied back with "yea but this bitch is tighter". We spent a couple of hours with the guys switching up with us. The whole time openly comparing our body parts and our sexual techniques. Basically we were treated like two pieces of fuck meat. It was obvious my tits are much larger than my friend, but apparently I give better head. On the flip side my friend apparently has a tighter pussy and both guys loved the fact my friend enjoys anal sex. Both were disappointed I don't do anal.
Interesting afternoon but we both felt a little strange about it.

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# 83064 - by Katy / October 27, 2026
    • - Dating Disasters -
    Straight Female / 20

    Lied To, Single And Knocked Up

    I’m 20 and work as a receptionist for a small company. About an year ago a very handsome middle aged (42) guy started calling on my boss and an after a couple of times he asked me to lunch. He didn’t try to hide the fact that he was married so I was comfortable since it just lunch a couple times to start.
    Then he invited me to have dinner one evening offering the fact that his wife was out of town visiting family.
    At dinner that evening he told me he was interested in seeing me more often. I really had begun enjoying his company so I told him I would consider seeing him occasionally. After that we had dinner a couple more times.
    When he invited me to take a weekend trip to Las Vegas a few weeks later I was hesitant knowing what would be expected but finally agreed.
    When the subject of becoming intimate came up on the trip he informed me he had had a vasectomy so there was no need to use condoms. It was my first time without one since that had always been my method of birth control and I thoroughly enjoyed the experience. That was in June and since we have been intimate a couple of times each month.
    When my period was due the middle of September I was late but of course wasn’t concerned. After a week I called him informing him I had missed my period. He then confessed he had lied about the vasectomy actually wanting to get me pregnant. He wants me to have the baby and give him time to work out the possibility of him getting a divorce.
    I have mixed emotions. I really like him very much but I don’t know if I can trust him to get a divorce leaving me a single mother. I don’t worry about him stepping up either way so I will just have to make a huge decision.

    4
    # 82976 - by Shannon / October 2, 2025
    - Dating Disasters -
    Lesbian Female / 37

    And Then A Man Is In My Life

    I have a lot of male traits, I'm bossy, assertive, single minded. Necessary traits to get my MBA and work in Private Equity. After a life with girlfriends I went to work for a big balls man who fucked me. It was unpleasant, but he pressed his advantage and I wilted. I don't recognize myself. Friends and family have a point telling me I went all pussy.

    I had to give up my job, I took a sabbatical. I'm in Costa Rica, waiting on him. A week on the beach. He comes tomorrow, I arrived yesterday. I'll be over my period, so he will have open season. After a week, I'll be ready for some me time, I'm going to my mother's. She 'understands' me. My father's just like him, takes a special woman to put up with them.

    1
    # 82942 - by Carmella / October 1, 2025
    • - Dating Disasters -
    Straight Female / 18

    My First Time

    I had a date for HOCO with a guy I’ve had a crush on since my sophomore year.
    After things were over we parked at a secluded spot kissing like I had done with other guys but he got me very excited doing things I’d never let anyone else do.
    I let things go too far letting him have sex with me. I didn’t want to break the mood so I let him nut in me.
    First thing this morning I slipped to the store and got a plan b hoping I won’t get pregnant. It was very exciting so I hope it works.

    2
    # 82852 - by Addi / September 28, 2025
    - Dating Disasters -
    Straight Male / 38

    Thought I Was Gay

    When I was 16 I was confused and thought I was gay. Way worried about being outed at school so I went online and found an older male. He was 30 and like the fact I was young. For a couple of weeks I let him pick me up, drive me to a secluded spot, and I gave him blow jobs. He had a nice 8 inch cock and I really liked sucking it. After I got him off I would be so horny I would jack myself off as he touched and kissed me.
    The day came when he wanted to fuck me. We got in the back seat of his SUV. We stripped down and I sucked him hard as he fingered lube in my butt hole. He put me face down, gripped my shoulders as he mounted me. G-D it hurt as he pushed inside me! To describe it, he reamed my asshole! 8 inches fucking me hard. The more I screamed and squirmed, the harder he fucked and seemed to enjoy it. He finally creamed me and let me up. I was sore for days. Pretty much decided gay was not for me.

    2
    # 82737 - by Was confused / September 24, 2025
    • - Dating Disasters -
    Straight Female / 27

    Size Queen (what To Do)

    I need advice. I am a very proud size queen. I can't help it. I was late to the sexual world. As a senior in high school my first sexual experience was with a college boy I dated for over a year. He broke me in with 9 very thick inches. I got that big dick constantly for a year and a half.
    After that my dating world had restrictions. I guy has to have a big dick in order to ring my bell. I simply do not enjoy sex with a small one.
    Now to the problem. I really like a guy I work with. We started going out and I very much enjoy spending time with him. Problem is, the night finally came and my expectations crashed. As I made a big deal of getting on my knees, erotically pulling down his boxers, I was face to crotch with a very small dick. Even after he got excited, only 4 thin inches.
    I really like him but I cannot have a sex life with him.
    What am I supposed to do???

    5
    # 82549 - by Confused / September 18, 2025
    - Dating Disasters -
    Straight Male / 22

    Dodged A Bullet, I HOPE!

    22 yr old horny college guy. Beginning of summer me and some buds were hanging out at the beach on a nearby lake. I hit the jackpot and had a SUPER HOT girl talking and flirting with me. Best description would be to say she looks like one of those beach volleyball players you see on TV. Tall, 5-10, toned athletic body, small but perky tits and just beautiful. Like WOW!
    Anyway I made progress and we grabbed our beach towels and went for a walk. Trail around the point and found a secluded spot. She put her arms around my neck and kissed me. I slipped her bikini bottoms off her hips and the fell to he ankles. O-M-G the prettiest little shaved pussy EVER! In a minute I had her on all 4's fucking her doggy. Not my best performance because I didn't last long. But I made up for it in round 2.
    We walked back to the beach and exchanged cell numbers. When I offered to walk her to her car, she told me she didn't drive. When I questioned why I quickly wished I had not asked. She replied "I'm only 14" and said her mom would be there soon.
    Lets just say I was in panic mode! I just had sex with a very underage girl and she had my name and cell number. THANK G-D I pulled out both times and shot on her back and stomach. But even pulling out there is a chance.
    First couple of times she called I made excuses not to meet up. Then started avoiding the calls. I haven't had a call in nearly a month. Please let this pass over.

    2
    # 82499 - by Me / September 16, 2025
    - Dating Disasters -
    Straight Female / 41

    Not An Actual Date But A Real Disaster

    In 1995 I had just started the seventh grade. My family was visiting my aunt and uncle in another state for a weekend.
    My cousin was 16 and had just gotten his drivers licenses so we asked if we could go to a movie on Saturday evening.
    After the movie we went to get something to eat. The whole evening I felt he had kinda flirted with me and it flattered me because I thought he was cute. After we ate he asked if I’d like to park and talk for a while so I told him yes.
    We talked for a while then he leaned over kissing me on the cheek but it didn’t take long for us to start kissing for real which was new for me.
    When he started running his hand up my skirt I started to say something but he quickly touched what he was interested in then kissed me at the same time going in my panties.
    It didn’t take him long to have me so excited that when he eased me down in the seat of the truck I just relaxed and enjoyed letting him have sex with me once he told me he would use a condom.
    I went home the next day thinking about how much I had enjoyed what we had done for the next couple of weeks.
    I had only been having my period for a short time never thinking about it until it came each month.
    Then one day I noticed that my tiny boobs were so sore I could hardly stand my blouse. Then at school I got dizzy and felt queasy. Finally I realized it was way past time for a period so I told my mother it was late but not that I had had sex. She took me for a checkup which showed I had gotten pregnant. Boy was that a shock for everyone involved. We all weighed the options and I made the decision that I wanted to have the baby.
    My daughter is now grown and the apple of mine, my cousins and our families eyes.

    2
    # 82411 - by Brenda / September 13, 2025
    - Dating Disasters -
    Straight Female / 31

    Bad Catholic

    Thought I was a nice Catholic girl. Married, mother of one. Now I am in so much trouble. I am pregnant, baby is not my husbands, and biggest problem is the baby is black.
    I didn't mean for this to happen. A few months ago my office hired a guy for public relations. He was like some kind of local sports hero a couple of years back. He is younger (early 20's) and VERY black.
    A short time after he started there rumors started that a couple of the girls in the building has slept with him. One day I overheard a small group of 3 girls semi whispering. It was obvious they were talking about him, and even more obvious all 3 had slept with him. What really got me was all 3 talked about the size of his penis. I got the impression it was very large.
    Shortly after I had an occasion to interact with him. He was very flirty, but all I could do was think about his penis and if it was true. A few days later he openly asked me out. I politely declined and told him I was married. It guess it only turned him on more because he kept coming back.
    One day I agreed to go around the corner to a deli and have lunch. Somehow I ended up in the parking garage in the back seat of his SUV. And "YES" it was big. So big I actually asked him how big it was. He laughed and said "little over 10 inches". I had only been with 3 men before and none over 6 inches. I insisted on a condom. I actually rolled it on his cock and we both kinda laughed. It looked funny, way too small and looked like a hat. I got on my knees, he got behind me, pulled up my skirt and pulled my panties to the side. G-D I had 2 huge orgasms in the first 5 minutes. I was so stretched and full I felt like I couldn't breathe. Finally he grabbed my hips and went balls deep. Suddenly I felt the warm feeling of his cum inside me, I freaked and tried to pull away but he held my hips and kept his cock inside me. When he finally pulled out I turned around. Cum was dripping all over the seat and I saw the condom on the floor. BASTARD TOOK IT OFF WHEN I TURNED AROUND!
    Now I'm pregnant. No good options. If I have the baby husband will leave, family will disown me. Can't pass off a black baby as my husbands. Being Catholic abortion is not an option.

    3
    # 82318 - by Me / September 11, 2025
    • - Dating Disasters -
    Straight Male / 45

    How I Got Into Voyeurism

    She’s younger than me her name is Stacy a very sexy blonde lady who had recently been divorced. She stated their relationship was too vanilla .I’m much older and we met at an upscale bar. She knew what I wanted and i knew what she wanted. She knew I was crazy about her curvy sexy body. I told her what I wanted in bed during sex. She loved what I would say. I had many fantasies i could never live out with my wife. We usually meet up at a bar nearby where my loft is walking distance. I won’t sit here and lie but she was the one who told me she loved hard deep pounding sex. I knew I wasn’t the guy. I told her what i could do for her and she loved the idea. Together we would scroll through the ads looking for the perfect guy. There were too many she would say for me to surprise her. This was the beginning of my getting to love sex in a wild way more than anything. She assured me no woman wants a guy who can’t last like her ex husband. I knew i could last but I lacked size. She had no idea the night i would surprise her. It turned out to be exactly everything she imagined and more. She got everything she wanted needed and sexually fulfilled. I would sit back jacking off slowly to her deep moaning and grunting her thanking me timelessly for giving her the worlds greatest pleasure experience. He was young but knew how to use it and good and long. We would lay in bed right after discussing how she would like to get it like that all the time. She was slowly falling deeply in love with me. I was only thinking of myself. I wanted to watch her with two guys to see if she could take it. She would and it turned out to be one of her fantasies she would later admit that night after. She was worn out from two straight hours of sex and she would tell me why couldn’t we be a couple. Almost ten years apart she was so sexy looking and always attracted men. She had the body every guy desires. No matter what Stacy wore she attracted men. I had to watch her facial expressions during the time she was getting pounded it turned me on extremely. She would lose control use profanity but in a sexual way which turned me on. I wanted to see her turn into a true whore and they made her accomplish it. More g*fts for her all she had to do was continue to let me live out my fantasies. Over six different guys now and I didn’t want to stop. Neither did she and she admitted it was addictive. She called me crying she couldn’t do it no more she truly loved me. Not even my wife would tell me that. My wife had become spoiled and tried to control me but the sex was too simple. Stacy would explain and admit my size was perfect and she just wanted me and the way I let her have her sexual freedom to rid frustration was over. It was something she wanted from her husband but he couldn’t do it and I let her and now she’s totally done. I eventually understood and during sex would she ever bring up anyone else. She would make love to me kiss me hold me and say everything right. I was ten years older and it sort of bothered her even though i looked great for my age. I made a tough decision and left the marriage and she didn’t even show emotion. It was all about value she wanted my money. Me and Stacy moved away living in Texas and are very very happy.

    0
    # 82072 - by Frank / September 3, 2025
    500 of 75,765 Confessions Displayed.

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