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.

She Heard Wrong

I met this chick at a bar, she asks me what I do, I say waiter, she hears writer. We fuck all night. She wants to read some of my writings, I have none. She finally realizes, waiter. End of the relationship.

  • I Won My Wife In A Lottery Of Sorts

    During my college years a group of friends and I decided to go skiing in Utah. We drove, four to a car and rented a couple of rooms at this motel. The idea when we left was that the girls would take one room and the guys the other but when we got there we decided it was time to pair up, all four of the double beds would have a boy and a girl and the girls were picked at random assigned to a given bed. The guys then got to pick the bed. For the girls tough luck, if they could horse trade out of the bed with another girl it was up to them.

    Her name was Paula and she was a nice girl from Corpus Christi Texas. She refused to admit she was a virgin but it was pretty obvious to me. She held her legs together as tight as she could and I had to break them apart by stiff legging her with my knee. That and a slap on the thigh. Once I was inside, and I was as hard as I had ever been, I was giving it to her as hard and fast as I could when she asked me to please not get her pregnant. I lost control at that moment and she got the full treatment, every last ounce of it. The rest of the night she was quiet and reserved.

    For the next three days all I got from her was her backside, which to me was new I had never done anal, but it was all I could get so that's what I had to settle on. She gave me a couple of reluctant blow jobs and she let me eat her out reluctantly too. I fucked her tits and got her face wet, she just didn't cooperate the way I wanted her to. Out on the ski slopes I kept her close and she let me teach her a thing or two and for meals and hanging around she did stay close to me. The three other couples did the same, except for the nighttime activities where they got it on while I had to spread her cheeks and go up her from behind.

    All the way back to college she sat up front beside me, by then she was a couple whether she wanted to be or not. When we got back I told her to get some clothes she was going to be sleeping with me at my apartment. I guess she had given up by then so she let me get to her right between her legs and fuck her the right way. We never did do anal again.

    Of course her worst fears came true, she was pregnant and we got married before the baby was born. She let herself get pregnant a couple of more times, and after about five years she came to bed and let herself without putting up any resistance. It took that long to break her in right and she was a good wife after that.

    We made it to our 25th this last year and we had a small get together and she had to recount how we met, keeping the bed assignment part out of the story. Now that our kids are in their twenties and God knows what they are doing and with whom, we behave like love crossed college kids for their benefit. She reminds the girls, doing it has consequences, they learned how to count a long time ago and know their mother was seven months along when she got married. The trip to Utah is not for an open discussion, it's just between us, and she will not talk about doing anal. It did not happen, as far as she is concerned.

    Keep Your Eyes On The Prize And Never Give Up

    I met this girl at a friends house. She was his cousin from across town. She filled my mind and I couldn't get over her. My friend told me where she went to school so I went there to wait for her to walk home. She was surprised to see me and told me she didn't have permission for a boy to walk her home. I asked my friend to tell her she needed to let me see her.

    Her mother told her that until she was older she wasn't to talk to boys, especially boys with a motorbike. And she wasn't ever to ride on a motorbike. My heart was torn out of me, I couldn't sleep, my friend told me to give up, she wasn't ever going to get permission to go out with the likes of me. Fishin' in the wrong pond boy, that's what my friend told me his father had said.

    I cleaned up, wore my best jeans, my sister cut my hair and she went with me to talk with her mother and get permission. My sister promised that she would be in the same room and that I wasn't bad like some of the other boys of my school. The answer was for me to stick to the girls of my side of town, this girl was too good for me.

    I wrote her a letter and told her I was going to college when I finished high school, just wait and see. To get to college I first had to join the Army to get the GI Bill. And she had no choice but to wait. I did my four years, two of them in Germany and when I got out I went to college and got a business degree. I married my sweetheart when I graduated and we are married today.

    And that's the way you do it. Boys from my side of the track never took no for an answer.

  • The Nurse

    A few years ago, I was on Plenty of Fish and went on a date with this good looking girl. I picked her up, we went to a restaurant and I drove her back home. She was a nurse - divorced - really nice looking and fun - but she wasn't my type and I don't think that I was her type either. We kind of agreed to this by the end of the date. To my suprise when I got to her home, she invited me to come in and I agreed.

    It was a hot summer night - three Gin & Tonics later we are kissing in her kitchen. Eventually the clothe flies off and we had sex in the living room, in the shower and in her bedroom. This girl seemed really sexually frustrated and we had sex for a good 3 hours. The next morning I woke up with her tongue delicately licking my balls - I was hard as a rock - she sucked me to perfection.

    She made me a coffee and after an awkward half-an-hour of small talk I left. We never contacted each other again.

    Protecting Your Teen Is Useless

    I asked my parents for permission to go to a New Year's party (back when I was a junior in high school). OK, but I had to wear a pad. Just in case some jerk got his hand down my pants. At midnight I got kissed, and his hand went across my behind and then up my shirt and pinched my boob and he grabbed me hard and shoved his erection against me and asked me if I wanted to fuck.

    All I could do was babble, sure I want to fuck, but where. We went outside and to his car and he told me to get in the back and take my pants off. He saw that I had a pad in my underwear and I told him it was my mother's idea. Not sure about what to do next he told me to turn over and he got on me from behind and ground his dick in until he got in my ass and I got my first ever butt fucking in the back of his car. Sure it hurt, but it felt good. I liked it.

    I went home that night with a sore hole, and wet cheeks from him leaking out.

    First of all when my daughters started menstruating I put them on the pill. When my daughters went out I told them to keep their legs together and their heads clear and if a boy asked them to fuck to give them the finger. Which method worked best I don't know, but the pad in your pants just gets you butt fucked.

  • In Trouble And I Have To Get Married

    During my last two years of college I got into a sexual relationship with another girl and we moved in together. I suppose sex gets old, certainly we went from sex all the time to sex once or twice a month. Much better sex, very sensual and emotional. Then one night a guy grabbed me at a party and the heat got to me and I cheated on her.

    She forgave me, barely. We went our separate ways after college but it was too much. Six months later we were living together, had the best sex ever and swore forevers. But my button gets pushed by the guy from college, he comes to town and I end up going home with a belly full of cum. I don't confess this time.

    But life kicks you in the ass. I'm pregnant. He is all for it, he accomplished his male goal. I want the baby, I'm four months now. I accomplished my female goal. The baby messes up the calculus. If I didn't cheat I wouldn't be pregnant, I cheated and got pregnant. She has given me an ultimatum, get married 'now' to her. He gives me an ultimatum, get married to him.

    It's nice to be wanted, but I'm going to marry the one I love.

    Knocked Up Like A High School Cheerleader

    I gravitated into this job, journalism degree, Hispanic, pretty face and camera friendly, and the girl on the side of an influential man. I was an on camera reporter on a midsized television market before my current high profile position. My relationship is a secret and I have had to be very careful. But now I'm pregnant. I had to get off my birth control and detox. He was sympathetic but his desire overwhelmed his judgement and he tossed my concerns aside.

    I am taking a leave of absence and going into hiding. I just cannot go the termination route and I cannot go the adoption route. I can't get married, he is married. I am not 16, I'm 37, a little late in the game to have an illegitimate child. As I let my mother know, I got knocked up.

    Dangerous Date

    I was on a dating site and this guy started chatting with me - it was a Saturday night and I was alone drinking a glass of red wine and looking for fun. He invited me over his place and this was a mistake but I went along anyways. His house was on a dark country road at least 1,000 feet from the main road.

    I got there and the guy was very different then his photo - his photo he had sent me was at least 10 years old. He was not as sweet looking and somehow he was trashy. I had brought a bottle of wine so we opened it.

    His place was a total mess and he looked like a meth user. He started telling me that he had recently got out of state prison and that he was horny as hell. He had two large guard dogs that he eventually tied outside by my car. I started looking around realising that I had to get out of there.

    He locked the door, shut all the lights downstairs and he grabbed me and told me that we should go upstairs - so I went along as to not rattle him. I noticed a large knife on the night dresser. The bedroom was a total utterly mess. He got totally naked except for his boxer shorts - he was actually a very fit guy - he pulled down his boxers - I noticed that he had a really nice cut cock - nicely trimmed - so I decided to calm him that I would give him a blowjob. I started sucking him for a good 5 minutes and this gave me time to think - but he got upset as he could not get hard. I was scared but trying not to show it.

    He asks me if I would do a few line of cocaine with him - he told me that he would perform better - I just smiled and said sure - he picked up his cel phone and called his pusher for some coc.

    The pusher was on his way over, now I really had to get out of there. He was naked and I was not - he started dressing up - this was my window to get away - I told him that I would go downstairs and turn the lights on for his friend (the pusher) - I leaned over and kissed him and I asked him if his friend had good stuff - he replied the best - this was to establish trust - I ran down quickly but not looking like anything was wrong - I turned on the lights - unlocked the door (which had two deadbolts for some reason) and ran towards my car.

    Thank god the dogs ran towards the house (prob as I had turned on the lights and they wanted in) and only started barking and running viciously towards me once I pressed my unlock button and the headlights of my car came on - but by that time I was too far and I jumped into my mustang.

    I started the car - put it in reverse and backed up the long country driveway - as I did not want to turn around in case he came out and try to stop me - once I got to the road I stopped and calmed down - took a second to catch my breath - I reversed into the dark country road and took off and headed home.

    I did a bit of research on the guy as I had his cel phone no. - turns out he works at a used car lot - scary to think that women go there and buy a car from this douchebag.

    He Stole My Virginity

    Hold on, before you judge, everything was consensual, I think there was just a misunderstanding. I'm not too shaken up about it anymore, just wanted to get this off my mind because I've been thinking about it lately. I'll admit that I made some mistakes too.

    I was 16 and messing around on Tinder. Boring summer, parents always worked, and friends were away on summer vacay. There was this 24 year old guy who caught my eye, we matched, and began chatting. He was real good with his words. I was hooked immediately, we even began sexting. He always thought I was 18 and living with my parents while working a part time job.

    One day he asks when would be a good time to meet me. I don't know, I just kept following my lie about a part time job and said that today was a good day. He drives up to my house with some pizza and a 6 pack. We Netflix and chill for a bit, but soon enough, we're making out. His hands got up my skirt and wow they worked magic on my clit. I came so hard that it was my first time shaking.

    I asked if I could return the favor, so he unzips his pants. His cock sprang out and it was impressive for a skinny guy! I got on my knees in front of him to suck him off. He wasn't my first cock to suck... I've already sucked off my swim coach to make varsity (maybe a story for another time). He soon pops his load in my mouth while pressing my head down with his hand to make sure I take it all. I try to get up to spit, but he keeps me down saying that I need to swallow. Even though I tapped a few times, he wouldn't let up, so I swallowed his load.

    This continued for awhile, I was just addicted to him. Some days I told him I had "work" but all I could do is sit all hot and bothered until the next day. We soon started giving each other erotic massages in my bedroom. I would lie naked so that he can massage me all over, ending with a nice fingering or oral. Then I would do him, usually finishing him off with some oral.

    One day, we were doing our usual thing when he asked if he could take it to the next level. I thought he meant the massage because he didn't add the oil yet. I said mhmm then I felt him climb on top of me. Instead of feeling the drops of oil, I feel something press up against me down there. I was a bit confused and said, "Wait what?" but he answered by plunging his cock deep into me.

    I bolt upright, grinding my teeth and groaning, but he took it as an invitation to grab my neck and whisper in my ear, "Fuck you're so tight for a White girl." He starts fucking me. I couldn't help but grip the sheets while I adjusted to him. Eventually, it began to feel nice until he quit early to cum on my ass. Then he had the audacity to say, "Wow you're so tight that you bled from a light fuck."

    I ghosted him after that. Thankfully he was normal so that he just forgot about me after awhile, didn't harass me or whatever. When the guy I had a crush on got back from vacation, I hit him up to see if he wanted to hang. I always hesitated before because all the girls say he hangs with girls only to fuck them, but I wanted my virginity to be special. We got burgers then chilled in his parent's basement late at night. He had so much pent up horniness that we ended up fucking a few times that night. He gagged me with my shirt because I was making way too much noise. But yeah, at least I got to enjoy fucking my crush after all that.

  • Mother And Daughter

    For about eight months I was fucking an older married neighbor.
    She's very attractive and extremely sexual. So when her husband, who works away a lot, wasn't home, I was fucking her.

    You name it, we were doing it. Oral, fucking, anal, ass to mouth, some fisting, toys.
    After a few months of fucking my neighbors wife, I began dating a girl my age. Someone I worked with.
    I'd always stay at her place, as it was close to work and we'd fuck a lot.
    Even so I was still screwing my married neighbor.

    On a Sunday afternoon with her husband working in Europe I was fucking my neighbor. My cock was deep up her pussy and she had me fucking her asshole with a dildo from behind.
    She'd just started to orgasm when her lounge door opened.
    We both looked to the right, to see her daughter, the girl I was dating from work, stood in the doorway.

    What's crazy, is her mom continued to orgasm on my cock as my girlfriend began to shout at us both.
    Obviously we stopped, but I was still horny as fuck and my dick was so erect.
    All I could think about was fucking them both, but unfortunately it didn't turn out like that.

    My girlfriend dumped me and moved jobs. However even though she promised her daughter she would, her mother didn't stop fucking with me.

    It was a disaster for a while, but as things calmed down and my ex girlfriend didn't tell her father, I figured when I saw my ex out in a bar with some of her girlfriends, I'd go and talk to her.
    She told me I wasn't the first guy her mother had fucked behind her dad's back. And suspected her dad knew and accepted his wife fucking other guys. She even suggested he might like the idea.

    That night I went back to her place and we had such amazing sex. It was if her inhibitions had been lifted and we got into some really dirty sexual experiences.

    We're now kind of back together, but we only see each other a couple of times a week due to work. But the sex continues to be awesome.
    She knows I haven't stopped fucking her mom, but we don't mention it.
    I'd love to fuck them both together and did recently suggest us all getting together over the festive period.
    She didn't say yes, but she didn't say no either. What she did say was "We'll see".