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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 / 25

My Reputation Is That I'm A Daddy's Girl Now

This is not funny. I went out with some girlfriends to celebrate a birthday. We ran into my boss from work and he was surprised at how I looked in civilian clothes out with the girls. He told me I had descent knockers, nice legs and a cute ass. I took it because we were in public. He asked me to dance, which was awkward, he is 44 and I'm 25. By the time I realized it he had me against a wall across from my friends. Looking me up and down he said he was totally prepared to take me home and show me a good time.

I didn't agree but he interpreted the silence as he was free to take me with him. He let me collect my purse and walked me right out the door to the parking lot and his car. He asked 'your bed or mine?', he was passed horny and he didn't want to waste any time. We went to my place, my roommates were out being Friday night. He barely pulled my panties off and he got his dick in me until he left his calling card. Only after sex did he undress me and appreciate me.

We got dressed, went out to another club, he took me to his house and 'showed me a good time'. We slept together and he took me to the beach to eat crabs for lunch, with white wine. He knocks and walks in, my roommates know that it's time to go for a walk when he takes me to my room. When they make references about that they say that Daddy was giving me a spanking. He takes me to his house and he wants me to cook, or we cook outside. More than once he's put an apron on me, with nothing underneath.

He likes dainty panties, short hair, push up bras. He calls me his fairy god daughter and likes parading me around his club to the guys. My weekends and holidays are taken up by him. My friend from the birthday night jokes with me that I got the birthday present, not her. It's a standing joke with my friends that I'm a Daddy's girl.

1
# 60943 - by Veronica / September 28, 2022
    • - Dating Disasters -
    Straight Male / 57

    What The Hell Happened

    A close friend rang and asked if I fancied a pint, hell yes and we met at the local. The beers flowed, he was more tactile than usual, but I thought nothing off it, we were a little tipsy after all. He invited me back for a night cap. Inside he asked how I thought our first date had gone then he was on me like a rash. I naturally pushed away, stumbled and that was when it happened. His hands on my head trapping it to the floor he used my mouth like a pussy, face fucking me ball deep which made me gag but not as much as when he ejaculated making me swallow, it was over. I used some expletives and left. Since then he keeps calling to apologise, he's my friend but can I trust him?

    3
    # 60867 - by Mark / September 25, 2022
    - Dating Disasters -
    Transsexual Female / 22

    My Worst Date

    I was 19, proud of my hormone induced growing buds on my chest. They were almost an A cup, puffy nipples, 1 inch wide areolae. They were very sensitive, my nipples would get hard at anything almost. The hormones made my already thin clit shorten up. It was about the size of my little finger and very easy to hide. I was at a resort known for being a sex retreat and also being LGBTQ and straight friendly. I wasn't prepared to go totally nude, though a transgirl did on most days. I went topless when I'd get to the beach. Todd was sitting next to me, and there were plenty of empty loungers. He was cute, and he seemed interested, when we started talking I told him about me right away that I was a transgirl and hadn't had bottom surgery.

    He talked to me like he would any girl he wanted to bed, i liked it, he was perfect. Six feet plus tall, 175 lbs, cut body, and wore tight swimwear showing a rather large and thick tube in his shorts and what looked like rather large balls. After a while he asked if he should go somewhere else and I told him I didn't mind talking with him at all. He said he was wanting to get some total sun and didn't want to take off his shorts if it wasn't OK with me. I was matter of fact, with my inner self drooling to see this adonis nude. He was indeed big, about 6 inches soft and while soft almost 2 inches thick. I immediately pushed it out of my mind as I was not experience in my backside, but had sucked before. I knew I couldn't take that large a cock for sex. I mentioned after about 15 minutes that he'd better put some lotion on or he'd burn in a place where no man wants to be sunburned. He said he didn't have any lotion so I gave him mine. He couldn't get it opened so I opened it for him, he asked me if I wanted to do it. I don't know why but I did rub on his butt, then rolled him over for his front. I jacked his cock till he came. I was embarrassed and wanted to leave but not before he asked me to dinner that night.

    We met at night, he was again the perfect gentlemen, we slow danced, talked, ate and at the end he suggested we take a walk on the beach in the moonlight. I was swooning, his arm around my waist on the beach, and he slipped it down to my butt, squeezing, and I told him I couldn't do that. After a while he asked why and I told him I was totally inexperienced back there. He asked about my mouth, and I admitted I'd done that with 2 boys, one for over a year, that and my hand. We ventured into the palm trees and we got quite far away from everyone else, he was very matter of fact, he said "Pull your panties down and bend over that fallen tree". I was in shock to say the least, I just looked at him and he repeated himself and said not to make him say it again or he'd hurt me. Hesitating, he slapped me twice really hard in the face and pulled down my dress to see my boobies, pushed me over the tree and yanked down my panties, ripping them in the process. I was just thinking that they were $40 panties and he ripped them when I felt the lubed head of his cock at my hole. "You're going to be my little slut you cocktease" he said and he pushed it in all the way and grabbed me over my mouth to muffle my screams. He held it in me firmly and told me not to say anything, I couldnt' anyway I was crying too much. He held it I kept contracting my muscles to ease the pain. Eventually he started his fucking me. He reached around with both hands and played with my little puffies and fucked for at least 15 minutes before he shot it all inside me.

    He immediately pulled out and I turned around and saw his erect cock before it went down, it was so big, and my butt hurt so much, it was like everything was shoved deep back inside me I actually felt bloated. "Now baby, you can play as much of that hot little tease you want, but you've been had, you've been fucked and you're going to get more unless you want me to hurt you some more". He announced that I was his as much as he wanted and there was nothing a little bitch like me could do about it. He made me smile and hold his hand when we walked back up to the hotel and into the elevator. I stayed the next four days with him in his room, at the beach with him we were both nude. I was sucking at least once a day and got fucked a minimum of twice a day. At the end of his stay, he took me back to my room, fucked me and left.

    I ended my trip a week early and went home. I had been forced to be his sex partner and there was nothing I could do about it, he never left me alone for a minute. I was hit a few times and he threatened to push his whole hand inside me if I gave anyone any indication I wasn't with him of my own accord.

    It's been two and a half years, I am a natural hormone B cup now, I finally let another man into my life. I decided I never want bottom surgery, I guess it's bad enough having two places for a man to insert, I don't want three. My boyfriend is fine with it. I might tell him about my experience one day.

    0
    # 60783 - by Dina / September 21, 2022
    • - Dating Disasters -
    Straight Male / 32

    Disaster, Then Cold Offer

    About 5 years ago I got an online match with a woman a few years older than me and from a rural town a far drive from mine. Barb was not very attractive, but I thought maybe we had a few things in common. Got together for dinner and there was just no connection at all, she was dull as a rock and didn't seem too bright or have much motivation for doing anything interesting with her life, at least as I would define it. Bad politics too, didn't think much about it but was vaguely bigoted.

    So that was it, until I got a call from her a month later out of the blue. Her car had broken down in an even more distant town and she didn't have any money, she hadn't been in the area that long and didn't have anyone else she could call. It was late, I wasn't sure about this, and she jumped in with "look you can fuck me if you want to." I was a little hesitant but she was reassuring, it was no big deal for her and would help her out a lot. So I jumped in my car and went to pick her up. My town was basically half way between hers and where I had to get her, so she jumped in and as we planned, I took her to my place first. The drive was pretty quiet, she talked a little about her problems with the car and work and I was noncommittal in reply. We went up to my apartment, she had to go to the bathroom, then came out and asked "couch or bed?" I indicated the bed, and without hesitation she pulled off her pants and sat back on it, legs open. I stood in front of her and unzipped in front of her hairy pussy, pulled out my engorged dick and pointed it at her vagina. "Go ahead" she said, and I did, sticking it straight in. I've never had such a mechanical fuck in my life. She stared at the ceiling, the door, anything other than me. At once point I put my hand down to her clitoris and she abruptly pushed it away with "don't even bother." She was completely unresponsive to anything I was doing. Her modest tits were under her shirt, and there was just nothing sexy about her except for her exposed pussy, which was pretty juicy and warm. I kept thrusting over and over as she laid back, obviously bored.

    And I have to admit, that excited me a little. She wasn't judging my performance at all; obviously I had already lost here in her eyes. But that meant there was nothing more to lose. As long as she didn't make me stop, I could just keep pumping into her and use her pussy to make myself cum. So I pumped and pumped into her like she was a big fleshlight with a head, and tried to hurry it up so I didn't lose my chance to cum. In a couple more minutes I started ejaculating inside her, and felt a little animalistic pleasure at filling her pussy with my semen. She looked up at me and said, "Ok, are we done then?" I pulled out, wiped my dick off, and she dressed and off we went. Dropped her off and never heard from her again.

    1
    # 60745 - by S / September 19, 2022
    - Dating Disasters -
    Straight Female / 36

    Tired Of Ships Passing Thru The Night, I'm Desperate To Get Married

    I am not some wallflower. I have a career. I support myself. I have lots of friends. But I just can't get a man to commit to me. Take me out, buy me dinner, go back, give him a blow job, let him fuck. That seems to be the routine, but no commitment.

    I'm getting to the age that where he clock ticks louder and louder. I don't want to leave this earth never having had a child, children really. Now at 36 I wish I had been one of those girls who got pregnant early and had four kids. Not be that woman who was independent and went to college and have a career, but at the price of an empty womb.

    There's a man I know. He's fucked me a dozen times. He's old school and all. Every time he fucks me I have to go through it all over again. That feeling that somehow he's marking me or something. He's not from here, I mean the USA. He's a foreigner, but he's been here forever. It's the attitude really. Believe me, he fucks to own, not for fun.

    But he likes me well enough. He had a family back in his country so many years ago but they are all gone and he is alone. Like I said he is from one of those countries where one night his family was wiped out. He has proposed marriage to me.

    I haven't accepted because of culture, religion, age difference. But he is the only man who has even hinted at marriage. And so here I am, 36. Single and without a better prospect anywhere, dying of thirst for a man in an ocean of men, but not one of them is open to a commitment to me and to give me what I most want, a home and children. Not an apartment.

    And I have to say this, so please don't be harsh. This man who fucks me, he's not Caucasian. He's not a black man either. But if I marry him and I have children they will be mixed. So there it is, do I marry this man and have the children I want, and a house that I can make a home? And accept that I will have to change and accept his world views of men and women. Or do I stay the way I am hoping some man I don't have to support shows up who wants a woman my age.

    6
    # 60502 - by Jamie / September 4, 2022
    • - Dating Disasters -
    Straight Male / 46

    Public Service Announcement

    I enjoy reading these confessions and creative writing essays here. I read many about men wanting to share their wives or watch other men fuck them. Well here's a couple of stories I know about what happened in real life to some people I know.

    An acquaintance of mine for years tried talking his wife into swinging. He thought it would be cool to watch his wife get fucked while he was fucking someone else's wife. After many years of constantly bringing it up she finally relented and they joined a website and got into swinging. Well the wife who was very reluctant started getting into it way more than he had planned. She was taking on 2, 3, and even more guys at a time. She was very popular and eventually had her a stable of young hung guys who brought her more pleasure than her husband ever could. They ended up divorced. She's still very popular and gets a lot of dick. He's miserable and alone and can't get laid.

    Another guy I know was always trying to get his wife to have a threesome with him and another woman. Again, she initially had no interest but for whatever reason finally have in. They put ads on craigslist back when you could do personal ads on there and met her now wife. Yep she found out she really liked pussy more than dick, and left him for her. I can't say I blame her, her wife is a tall thin redhead, who I'd give my left nut to fuck just once. What's even more funny to me is that he's now taking it up the ass from his boyfriend and whoever else he can find.

    I know I'm probably in the minority on this site but I think if you have a great marriage and a great sex life with that person you committed to, you should just be happy with what you have. The grass isn't always greener on the other side. It may look real nice but...

    0
    # 60282 - by A E Newman / August 22, 2022
    - Dating Disasters -
    Straight Male / 34

    Date With An Asexual

    Earlier this summer I started dating a nice, slightly overweight lady, and we soon started watching movies together at my place once a week or so. When I started hinting that I was physically attracted to her, she admitted that she was on the asexual spectrum, but really enjoyed cuddling and spooning. I was up for that, and we did that a little on the couch after one movie. She then asked if she could stay over, and I really wanted to be with her, but after we got in bed, underwear on, I told her I couldn't help but have a huge erection, and wasn't going to sleep unless I had an orgasm. She then shocked me by saying she would watch me do that, and I could cum in her mouth if I wanted to. Huh? But then she explained that while she didn't feel comfortable with sexual penetration of any kind, she wanted her partner to feel happy, and guys had in the past jerked off onto her face or mouth, but the latter less messy and she didn't mind the taste if she swallowed it quickly. This was a big surprised, but I quickly obliged, stripping down and beating off over her face, occasionally rubbing her skin with my cockhead. She just watched for a while but when I got close she opened her mouth wide and I aimed right at her tongue as I started spewing my white cum into her mouth. The first two pulses went way back, then a couple landed on the front part of her tongue in a wet glob. I wiped another drop on the inside of her lips, and then she swallowed and came back to suck just a little more off of me. We slept wonderfully, and in the morning she let me do this again. We've gotten together almost every week since then.

    I may one day want more than this, and in fact am still on the dating market, but for now I could do worse than to keep cumming in her mouth. She's good-looking, fun to be with, and even though we've never kissed or done anything more, she helps satisfy my needs and feel good in intimate moments.

    4
    # 60218 - by Craig / August 18, 2022
    - Dating Disasters -
    Straight Female / 32

    Would This Turn You On?

    I'm a single mum which makes it hard to date, I'm white and my ex-husband was black so that makes things even harder as my child is dark-skinned. I dated someone for a few months but he started to get jealous that my ex had some "massive black cock" and that I wasn't satisfied with him. Not all black guys have huge cocks, he was bigger than my ex but refused to believe it no matter how many times I told him. In the end I just sent him a video I had of my ex husband fucking the shit out of me for an hour straight and told him we were over.

    He responded to say he was sorry, he acknowledges he was wrong but the video turned him on and he still wanted to be in a relationship. He'd just watched another man fuck me and he was still interested in a relationship?

    6
    # 60127 - by Rosa / August 13, 2022
    - Dating Disasters -
    Transsexual Male / 31

    2005 Fuckery Poem

    flag me, shag me,
    I will ride all night on this limo
    don't you go lag me
    your my hunter nimmo

    trust me don't bust me
    let catch that rove
    don't sacrifice this love

    sleeping with a loaded gun
    is like making love on the run

    fast track my heart and dance a little here
    lets chance away every maidens fear.

    to fabian there is no baby in.

    1
    # 59917 - by Velofello / August 4, 2022
    • - Dating Disasters -
    Straight Female / 27

    Number 2 Girl, I'm Upset Right Now And Want To Feel Like Number 1 Girl

    My boss decided that I needed to get some time away from the office. Forced vacation. The reason an investigation into misappropriation of funds and he didn't want anywhere close. He hid me away in his lake house. The place was country comfortable as far as that went, but boring being alone. I called him on a private phone he set up for me. I started to cry and couldn't stop. He promised to drive out, which is 3 hours from town. I waited for him and ran to him when he showed up. All I wanted right then were his arms around me.

    He is a big time CEO and having a lover at work right then was a problem, conflicts of interest. For me being hidden from sight hurt beyond anything I could bare. I begged to go home and not be left alone in the boonies. He spent the night and told me to sit tight, he would come up with something. He moved me in with Ruthie, his ex mistress of fifteen years. She does anything he says and I have no doubts that she is there for him when he needs her with her legs around him.

    For three weeks I lived at Ruthie's. The investigation was over, the guilty parties discovered and fired, one of them was my immediate supervisor. The decision was to have me resign, and live with Ruthie. At least until he could place me with a friend. Or until he decided to keep me at Ruthies. My life is upside down, Ruthie thinks she's my mother, waiting for him to come see us and be the father in the house. He kisses Ruthie, kisses me, pulls me by the wrist into the bedroom and releases his day's frustration, then I go help Ruthie with dinner. After dinner I help clean up and he sleeps with Ruthie and I sleep on the sofa bed in the living room.

    1
    # 59663 - by Sarah / July 21, 2022
    500 of 75,765 Confessions Displayed.

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