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.

Pregnant At 16

We were new to town and hadn't made any friends. It was prom week and everyone was talking about who they were going to prom with. The son of one of my father's coworkers was graduating and he was told to take me to the prom. I got a dress and shoes and went to the hair salon. He picked me up, he had to talk with my Dad. The prom was at a hotel in town and my father told me not to go to any rooms.

Halfway through the prom he told me and some friends were thinking of going to the lake. Everyone was a senior except for me. I said I would go I did not want to go home. The drive was 45 minutes, I rode with him. On the way I started to think about losing my virginity that night. At least it was going to be with a senior and not some little kid. I thought about my period, at least I wasn't on my period. I would tell him to pull out. Problem solved.

At the lake there was lots of alcohol and other things. Couples were making out and he asked me if I wanted to. We made out, he felt me up pretty good. I could see out of the corner if my eye a couple having sex. That was going to be me. My pants were off, I pushed him back and told him he had to pull out. Sure, he told me he would. I took off my panties and laid down on the carpet with another girl by my side. I spread my legs, saw his hard dick, and closed my eyes.

He didn't pull out. S8rry, he forgot. I got scared, went to the bathroom and vomited. Another girl asked what happened, I told her, she told me she had a morning after medication at home and she would give it to me. Except she left with her date and I stayed because my date was drunk. I woke up with another girl, she asked who I was. I never saw the girl with morning after medication. I got pregnant at 16.

I never got an abortion, he told me he would marry me when he finished college. He never did. I changed schools, to a home school program till after the baby was born. I never returned to that high school, none of the girls at that party ever looked me up. Not until I was out of college. Then the girl with the morning after meds called me. Sorry.

My daughter is 9, I teach second grade. I gained a lot of weight. I have a guy, not a boyfriend, a guy who has sex with me. He works downtown and no one knows about him. It's sex. I met him at a party. One day I'll meet a guy to get married.

  • Still Technically A Virgin

    I am sick and tired of hearing about how women like big dicks. I have a very big dick. Bigger than even most of the porn stars I've seen. I am not bragging. I am complaining. I still have never fucked a woman. Not from lack of effort but every time we start getting down to business, once they see my dick, it's over. No way will that fit, or oh my God! That's way too big. I have eaten their pussy for long enough for them to cum multiple times and even then, it's usually, no way Jose'. One time a girl I dated tried with her on top but barely got past the head and said it hurt too much.

    I did let this guy blow me once in college but I was drunk out of my head and hardly want to go there again.

    I really don't know what to do. Is there somewhere you can go to find women with really loose pussies? Someone who can not only take, but enjoy a really big dick?

    Mine is just over 10" long and a bit fatter than a half liter soda bottle.

    I'm getting desperate. I'm afraid to date women my age as I'm tired of rejection.

    Catching My Man

    The difference with men and women is easy. Men have sex and walk away. Women have sex and they are hooked on him. Especially if she is young and he's older and mature. I was 19, he was 29. My life experience was limited to living at home, his life experience was Army Ranger, officer, stationed overseas, combat, Master's degree in Engineering. And heavily experienced in matters of the flesh. Woman flesh.

    How many women? I didn't care. How many men for me? Zero. All I know is that afterwards I was a woman. He didn't think so, but I knew so. I did what women in love have to do, I haunted him, when he looked up I intended to be there. As far as I was concerned no other woman would catch his eye again. Of course, in my mind. He had other women, I imagine some were like me, he was their first and in love, and others did those things for a living.

    I got up the nerve and went to him and asked him why he didn't call. It was just sex he said. Not to me, I said. A woman, I reminded him, doesn't play around. He looked at me, a girl would say something like that. I had a lot more work to do. I'll cut to the chase, it took me all of my sophomore, my junior, and senior years. By the time he saw the woman in me, I was an experienced woman. How many men for me? One. I won't say how many women for him, it's not becoming to be counting other women.

    I'm married, my idea not his, but perseverance has it's charm. I don't ask him where he's been, none of my business he says. I don't ask but I got him guilted into telling me. Ruined it for him. Sorry, a woman doesn't kiss and tell, and it turns out that him kissing and telling started to sound bad to him, like a kid bragging. So I can only conclude, he's down to one woman. And that's me. He's not bragging any more.

    I'm not bragging, it's true.

  • I Was Straight All Along

    My father is a police officer. Very dominant. When I was little he was very protective and loving. When I went through puberty he was controlling, dominant and abusive. It was so bad my mother sent me to live with her sister. A sweet lesbian with a dominant lawyer partner Christine.

    Chris always 'liked; me, I am her favorite. She cut my hair short, bought me boyish clothes, allowed only very subtle j*welry, talked about me meeting the right girl. She also shaved and waxed my privates, because when it came to that a nice compact smooth 'kitty' was what girls liked when it came to kissing. She also told me that if a girl didn't pay attention to her snatch not to go down on her.

    All during my teen years I was around lesbians, I was introduced to nice girls, only allowed to date girls, I had various sexual partners which Chris debriefed me on giving me best pointers on how to make a girl cum. I was sent to Chris' alma matter, a small school with a reputation for lesbians. I can't say I met an out straight girl there. When I went home I was treated to spa day, full Brazilian, new panties, always new panties. Chris was deeply interested in the girl I brought home. Be more assertive, let her know you will take her hand.

    When I went to work after college, before law school, I met a man, mid thirties, assertive, masculine, strong, and he tore through me like a hot knife through butter. I babbled, became a five year old, wore a dress, and the beautiful earrings he gave me. I went from tomboy to fem.

    Chris was sick about him. She was downright ugly to him. He wasn't phased at all which pissed her off. I 'blossomed' with him and fell hard for him, my first unabashed love interest.

    I have close girlfriends, I grew up around lesbians and can navigate the 'parties'. I don't ask Frank to join me, he is turned off by so much estrogen. I have since going straight but remain intimate with one girl. Like me she gets visited by a boyfriend. We escape, and enjoy, but when he whistles we run home.

    Just Another Girl

    People don't realize that it's not easy to find a partner when you're pretty. They also make assumptions like I'm dumb because I happen to be a pretty blonde. Even after finishing my computer science degree there are people out there who make excuses like I got a higher mark just because I'm pretty.

    I'm just another human and I can do the same job as you so why do I get treated so differently. I want to he treated the same as everybody else. I don't like it when men open doors, stand up to give me a seat, or help me up when I trip, but not do the same for another person just because I'm pretty and they are not. I want to find someone who can treat me just like another person, and like and accept me for who I am and not for my looks.

    I'm not outgoing or an extrovert like people think. I like wearing cute dresses and slightly revealing clothes, but that doesn't mean I'm an extrovert. I actually wear it for myself. I'm actually quite shy and introverted. It's a bit hypocritical of me to say this but, sometimes I wish some of the nice and introverted guys would have the confidence to come up and talk to me and get to know me without taking my looks into account.

  • When My "Daddy" And I Got Caught

    Basically I got into an affair with one of the Execs at work. Twenty plus year difference in age, and several million difference in money. From the beginning he asked me 'whos your Daddy?', and I answered 'do you love your baby?' Childish but when your pressed together with his dick in you you get childish.

    He was across the world in Singapore and I texted him 'whos your baby?', I didn't know his wife was with him and she saw the text hit his phone. The whole thread lit up, he had me on his phone with a pseudonym and his 'baby' and my 'daddy' texts were out there for his wife to read.

    When they were back there was a lot to answer for, form him to her. From me she got 100 promises I couldn't keep, the one she asked over and over, no daddy, no baby. But he's my Daddy and I'm his Baby and now my nickname is Sally, which was the pseudonym he used on his phone.

    I Had To Make A Career Change

    Needing money while in college I agreed to see men for money. My first client did not take me seriously. I'm not saying he laughed but his response was humiliating, here I was willing to have sex for money with a man who had called for an escort and nothing. I had to leave, no sex, no money. I became a nurse working in the NICU.

    Didn't Do So Good

    Karma. Good luck. 17, I borrowed my grandmother's Pontiac Bonneville and went to the drive in. I talked to this girl who worked at the drive in. She said she was going to junior college and it was a part time job. She wanted to know if I was going steady, I said no. She invited me over, she lived in the trailer park down by the fabrication plant. She showed me around, she lived with her sister who worked at a club and wouldn't be home until after she got off at two. She sat back let her legs open, wanted to be sure I wasn't going steady.

    She called me to get closer and held my belt buckle, I don't know what she said. She had my dick in her hand and started to suck me. She pulled my pants down, and leaned back on her bed and took her pants off. I couldn't take my eyes off her snatch, that's what we called it. She pulled me forward by my dick and I fell on top of her. My dick went limp, she got mad and told me to grow up.

    Karma. Bad luck. I crashed my grandmother's Bonneville on the way home.

    I Sleep With Him Because I Love Him

    I have been in an inappropriate relationship for the last three years. With a married man. Friends with benefits. Sex.

    It started in the office, a touch, a pat on the back, a pat on the bottom. After the pat on the bottom a kiss on the lips. And then, he touched me between my legs. That's when I grabbed his dick in his pants, and he grabbed my breast, and that night after work I joined him in a cheap motel by the freeway.

    And now three years later, through the pandemic, in motels for a while, then my apartment after my roommate moved out. Friends with benefits. Right? Wrong. I'm in love with him and I dream of finding a way of being his wife. I don't resent his wife, I just want to say that, it's just unfair. I would be a great wife, if I had the chance. Instead it's friends with benefits.

  • My Blind Date Was A Foot Sniffer

    I was on a Blind Date and went to this nice restaurant and the Waiter told me my Date was in the restroom.

    So I sprayed perfume on my neck and put lipstick on my lips as the bathroom door opened and I was completely horrified.

    A man wearing nothing but a pink thong and he was barefoot walked out of the restroom and said "Hey Baby" to me as he placed his hands on his head and swiveled his hips and then licked his fingers and rubbed his nipples.

    I was completely grossed out but then the Blind Date from Hell picked up his bare foot and started smelling his feet in the restaurant as I screamed in horror, ran out the door, into my car, and drove away.

    I will never go on another Blind Date ever again.