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 / 30

Guy I Met Onlinr Was A Totally Mess...

I had a very weird experience with a guy I met online we called each other like for a month and video call before we met in real life because I was out of town and during we chatted he was really cute always calling me and looked that he was interested in me and when we actually met it was on Valentines Day and he wasn't at all what I expected. First of all I am 30 years old and he was 40 and he acted really imature he talked like a chatterbox for the entire date, we met at a coffee shop and he didn't look to be that interested in me anymore always checking his phone snd looked distracted like I wasn't even there. He was really short too he lied he was over 1.80m but didn't have that height and he looked kinda gay. I am really disappointed I don't think I will meet again a guy from the internet.
I was scared at first that he will try to flirt and try to seduce me to have sex with me at the first date but I must confess I was really relieved that he didn't have any of these thoughts. He lied about his job too and I was completely honest about everything.
I can't believe that these kind of people exist amongs us.

1
# 49789 - by Alicia / February 23, 2021
    • - Dating Disasters -
    Straight Female / 26

    Wrong Guy. Right Guy.

    For a while I lusted after a guy who was handsome, muscular and always played it cool.
    He was my dream guy. Someone my pussy would become wet to when I saw him. And a guy who I'd mastubated to, imagining him fucking me.
    When we finally got together through a geeky friend of his, I was so excited. We ended up after two dates back at his place, and boy what a let down he was.
    First of all he was a terrible kisser. Then when we got naked, his penis was so small (Not that's bad, but he so bragged about having a huge cock). He didn't like cunnilingus, and I ended up masturbating to get myself off, after he fucked me so badly like a wild man.
    Lastly and weirdly he told me, I'd had the best sex I'd ever experience with anyone. He was just so full of himself.
    A few weeks later I got chatting to his friend, who it turned out wasn't exactly his 'friend' but someone he kind of knew to ask me out.
    He was and is such a nice guy. We got on so well and I found myself intrigued and turned on by him.
    We dated four times before I asked him back to my parents. They were out a football game, so I knew I had hours to enjoy the date.
    Kyle couldn't have been more different. Subtle, funny and sexually amazing.
    He was so attentive to and with me. His cock was so big I had trouble giving him a blow job. Yet he was so gentle and understanding when he first entered my pussy.
    Only when I was comfortable and asked him to fuck me, did Kyle thrust deeper and harder.
    We had sex for nearly an hour, with his mouth, tongue and cock making me climax multiple times.
    It was a thrilling, exhilarating experience and I found myself so sexually alive with him.
    We dated for nearly two years before he proposed to me on Valentines day. And we married a year ago this coming week.
    I love Kyle so much and now wonder, if I hadn't had such a bad date, would I now be with the love if my life.

    2
    # 49609 - by Jess / February 14, 2021
    - Dating Disasters -
    Straight Male / 52

    Massages Went Awry

    I emotionally connected to my young female massage therapist. She was very revealing with private life and even made a point of saying she was single. I was looking forward to seeing her and asking her out (even if meant I wasn't her client anymore). The next time I went to see her she immediately said she felt uncomfortable about what I said during the last session. I was flabbergasted as I didn't think I revealed anything more personal (actually less) than her. It was an awkward massage. I think I'll quit going to the place. Mind fuck tease.

    3
    # 49458 - by Mr E / February 5, 2021
    • - Dating Disasters -
    Straight Male / 64

    I Ruined A Real Princess In High School, Being Sorry Didn't Help

    My father was posted to Latin America during my high school years. I attended a private school which had both expat kids and kids from upper income families. The normal social structure didn't involve expats dating locals. But at a class field trip to the top of a volcano Anabela, the prettiest, nicest local girl sat beside me on the bus, and she politely talked to me.

    At the top, off the bus, I escorted her. She was mine. When we stopped for lunch on the way down the mountain she had to sit by me. I got stares from several of the other local girls, and a couple of the local guys. But Anabela didn't ask for help, so I was able to monopolize her. That day, and afterwards at school, and parties. Like it or not she was my girlfriend as far as the class was concerned.

    She never introduced me to her family, I never went to her house. Her father was a big time lawyer, a plantation owner, and owner of several factories. At a party of one of our classmates I caught her and found a bedroom and nature took its course. I felt like I was king of the mountain, I had gotten the school princess and broke her hymen. She was hurt, embarrassed, ruined. But no one told me. She didn't return to school.

    A couple of weeks later this car with four guys came to my house, when they were done with me I spent a couple of days in the hospital. My father was visited by her father. We left the country. We were gone in a day. From what I found out many years later she was sent to Switzerland for a year, when she came back she went to a small Catholic school. She never married, neither did I. I never spoke to her again.

    0
    # 49382 - by Dumb Ass / February 1, 2021
    - Dating Disasters -
    Straight Male / 34

    Not "Heebert", It's "Aybear"

    While I was living in California I met and got into a relationship with a Japanese American girl from San Mateo, California. Leave aside her politics, I am from Louisiana, she had the California attitudes that made her both sexually adventurous and sexually prude at the same time. Everything was about her, how did she feel afterwards. In Louisiana we have nice girls and they are more into making sure that the guy is taken care of, and they understand that cooking means cooking. This Japanese girl, her idea of lunch was going out.

    I'm not saying that sex with her was bad, it wasn't. It was the focus on herself that drove me away. I literally handed her a mirror and told her to have fun. I'm back in Monroe and I have a nice Cajun girl who talks about kids. Refreshing.

    0
    # 49273 - by Hebert / January 27, 2021
    • - Dating Disasters -
    Bi-Sexual Female / 20

    Mama's Boy & Clueless

    So I'm not used to sharing stories like these but most people I tell this story to just go, "There's no way that happened. No date can be that bad." But I assure you... It did...

    To start, I get a date with this guy in my class who I thought was pretty cute, seemed pretty funny, so I was pretty happy to go on this date. He says, "Sure I'll setup where we're going. Just dress fancy."

    The day of the date comes, looking great in my open top just in case he gets any ideas, my mom drops me off at his place and drives off. I knock on the door, he opens up looking... fairly casual but whatever. Turns away yelling out, "Okay mommy my date is here, I'm leaving" So right there that was pretty weird but maybe it's some kind of inside joke so I don't think anything of it. The car ride was pretty basic nothing too much to note. We get to the restaurant and the place is pretty hard to get into especially since COVID. Now keep in mind this place NEEDS reservations before anything. We go inside and sit down because no one was at the booth and in my mind I'm thinking he set one up. 30 minutes go by and waiter after waiter walks by and I ask, "Hey, did you happen to get a reservation?" He goes, "Reservations?" So at this point I'm pretty much done with him and before I could text my mom to pick me up he goes "Well there is a Wendy's not too far away we could just go there." Now I'm in a open top dress so I'm just thinking there is NO WAY I'm sitting down in a Wendy's with thing so I suggest just to go through the drive thru. He goes, "Nah, they always get it wrong" So now I'm stuck looking like some kind of hoe in a Wendy's. As we're eating he gets a call, he picks up saying "Yes mommy?" So now I'm really creeped out cause clearly now it isn't a joke. In this time I text my mom to pick me up and after he hangs up we talk for a bit longer. He asks me if I wanted to go back home with him and me holding back laughter I tell him my mom is almost here and to not worry about it. Out of no where he just blurts out, "But I thought you wanted to fuck tonight?" Never once did I mention that I wanted to fuck him in out texts. So now the whole Wendy's is looking at me like I'm some kind of whore. So I just run out and wait for my mom holding back tears.

    But yeah, he texted me the next morning asking me what's wrong... Yeah talk about clueless

    1
    # 49221 - by Girl4Fun / January 25, 2021
    - Dating Disasters -
    Straight Female / 22

    Blind Date

    I have had a thing for older men. Especially older men who are still in shape and have that air of confidence experience.
    I set up a profile on tinder.
    I came across a handsome older man who looked very familiar but i didn't care all that much.
    I got excited met the gentle man and fuck its my step dad.
    George and i are both weirded out we both know we are there to meet each other.
    So it turns out he and my mom like having an open relationship. After a creepy conversation and ice cream i at least knew my step dad was not a cheating pos and not being a creeper.
    I tell him the odd thing is i always thought you where hot growing up. We end up at my house have a few beers. We talk about him and my moms relationship and i shocked at how open they are.
    Then he really fucks my shit up he texts my mom Tabitha is my tinder date how odd right.
    Well thats hot she texts back let me know how it goes.
    Im dressed up in cosplay high heeled boots. fishnets blue hair short plad black and gray skirt see through nylon shirt corset on.
    I look down notice a pretty big bulge in his jeans.
    I feel like im wearing lingerie for my step dad. I kinda feel like we are in that pre fuck stage listening to music on my phone and speaker. Drinking beers talking and enjoying his company.
    Imma go put on something less lets fuck george say and something more cuddle. I blush.
    If you where not my step dad i say to him and i lick the air. On the way by and around him he puts my hand on his crotch. This crafty bastard has his dick put in his lap. Im already struggling with my desire and urges to fuck him and have been since sixteen.
    All that comes out of my mouth is okay well then there is that.
    We sit on the couch hang out drink the rest of the six pack watching rick and morty while he gives me a foot massage.
    Now before i know it George has eaten my pussy and my ass i love anal i have a last minute thought that fades away as a new thought enters my mind... From old thought to god damn George has big dick. And he dose have a huge dick i get fuck in missionary for a good couple of orgasms then i ride him ome my god yes then he puts me on my hands and knees the whole time he is fingering my asshole im cumming so hard. George cums he stays in me.
    Half way soft he puts it in my ass. My first real anal it hurt and burned as he got inside of me it felt good as well though. Before i knee it im lays face down white he rubbs my pussy and fucks my as i admit it feels amazing and im cumming from anal like my pussy was orgasming from George fucking my asshole. He cum in my ass . we fall asleep together and wake up together. When we wake we had some more sex in my pussy it felt incredibly good. He got dressed and left.

    Today i remembered what i ment to say before me and George had sex. four weeks later it pops in my head as im at work throwing up in the toilet. Yeah im not on birth control until my health insurance kicks in. Im praying its the flu and not morning sickness

    1
    # 48877 - by Tabby / January 9, 2021
    - Dating Disasters -
    Straight Female / 27

    Out Of My Comfort Zone But I'm Having Trouble Breaking It Off

    I worked out every day before work. This girl about my age started working out during the same time slot. We showered together, she was a whole lot more casual about it than me. She stared me down, washing her kitty, her boobs. She caught me putting my bra on and told me it was a shame to have to hide my puppies. She sat on the bench drying her feet, her legs crossed showing her full womanhood. She took my brush out of my hand and insisted I let her comb my hair. She asked if I liked her rack, she told me it was all natural and I could touch if I didn't believe her. Day after day it was one thing or another, always pushing her tits or kitty on me. One of the trainers told me she was a dyke and she had told her she was going to get me in the sack.

    So why did I wait for her, shower with her, stare at her tits, her kitty lips. Why did I sit there and let her see me naked, admire my rack, my kitty, my eyes. Let her touch me. I wasn't able to resist, I went out with her, and she took me straight to bed and I complied with everything she wanted to do. I know what happened but I don't understand what happened. I've been dating her for over a year, and I still don't understand why. I told myself I am going to stop seeing her, it's my 2021 resolution. But why do I feel so bad.

    0
    # 48745 - by Lina / January 2, 2021
    - Dating Disasters -
    Straight Female / 18

    Kinky Or No?

    is it vanilla to want to be called a slut or a dumbass and be fucked until i cry or am i not vanilla idk someone tell me

    3
    # 48621 - by Anonymois / December 27, 2020
    • - Dating Disasters -
    Bi-Sexual Female / 29

    Life Is Very Complicated For Me Right Now

    I work for a large company and my team was having an after work birthday party for one of the girls in our team and I had agreed to go. I got caught with some extra work and I was late. On the elevator, on another floor this girl got on and we said hello and she asked if I had plans and I told her and she told me that those parties were not for good girls. That only bad girls went to those.

    When we got to the first floor and were walking to exit the building she asked if it wouldn't be better if I passed on the party, if I wanted we could go get something to eat at this restaurant near by. She introduced herself, she worked in HR, she was single and obviously didn't have anything for Friday night. She refused to come to the party and guilted me into going to dinner with her.

    We talked a lot, and after dinner she told me she lived in a high rise about two blocks away and I should come over. She had picked me up and at her apartment she got me into bed with her and after holding hands for thirty minutes she suggested we make love. And just like that I spent the night with her.

    The next day she asked me to go with her to see her daughter who lived with her sister and brother in law. The girl was four and she was excited to see her mom and we spent lunch there. On the way out her sister pulled me aside and asked me not to break her heart.

    I had a boyfriend, pretty serious, he wasn't amused by me spending the weekend with her. He insisted on me breaking it off. I couldn't and didn't so my three year relationship with him ended. After we got told to stay in I moved in with her and when my lease expired I let it lapse. We have her daughter for weekends, sometimes we go out to pick her up and sometimes her brother in law drops her off.

    I feel at times that sex is not complete, I miss having my boyfriend cum in me. I miss it a lot. He is not interested in sharing a relationship, he wants a formal commitment and me to agree to start a family with him. I find myself laying beside her and telling her that I love her although I don't know how I really feel. I have not been able to do more than see my boyfriend during the day and escape to his apartment to have sex. My girlfriend does not want me sleeping with her when I am full of cum, so we sleep back to back. Since I started living with her I have not missed a night with her, anything with my boyfriend is during the day but I am at home for the night.

    I have asked her to give in, understand that I need to have sex with my boyfriend, I need it badly and she should not give me the shoulder when I seen him. I want her to eat me when I come home from seeing him, I have this impulse to have her eat me with his cum in me. It's stupid I know but I really want her to do it, not that she will.

    When her daughter is around we are very careful and respectful, my boyfriend is very nice to her and he is respectful not to show undo affection to me and lets her mother and I be affectionate. This situation has made things more difficult, we are working from home, I go into the office once very two weeks to have a meeting with my team in a large conference room. It is on those days that I see my boyfriend at his apartment.

    What else can I say, it is complicated.

    2
    # 48422 - by In the Middle / December 13, 2020
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