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.

Somethings Missing And I Don't Know What

I've been wholly lesbian for fifteen years. My thirtieth birthday was on the 4th. I went out to a favorite ladies' bar, and went home with a woman I met there. We were in the heat of the moment, my face between her legs. She locked my head between her legs and a man r**ed me. I was knocked out and woke up half dressed on a street in the harbor part of town.

No one knows who she is. No one remembers her. The videos don't show anything. No one remembers me at the bar. All I know is I got picked up and r**ed. I woke up on the street, eking out his cum.

  • I'm Running On Empty

    Fast and Furious. We saw the movie, my date decided he was as good a driver. We hit a railing and flipped over. I woke up in a cast up to my ass, and a neck brace. I had a hospital gown on with nothing underneath. The nurse helped positioning the bed pan, wiping my butt. If it wasn't for the pain meds I could not have gone through it.

    I moved, dropped out, left that college town. I drove west until I ran out of gas and money. I got a job as a housekeeper at a motel, and a room. In one room I found a man, injured very bad, his family left him there while they went to visit relatives. I helped get him comfortable, use a coffee can to pee in. I asked him what he needed, to see if I could help him.

    He was blunt, he wanted a hand job, better still a blowjob. I was stunned. But I said a hand job, no blowjob. While I was working on him he grabbed my neck pushing my head down. I opened my mouth and he came in my mouth.

    I never saw him again, I quit that job, made it as far as Reno. That's where I am. No hand Jobs, no blowjobs, no spreading my legs. I'm off the market.

    She Just Didn't Care

    About 25 years ago I met a woman in an internet chatroom, honestly I don't even remember her name but let's call her Julie. She was about 5 years younger than me and from a poor part of town. We met in a sex chatroom so we knew we were interested in sexual talk or more, but from the moment we met it was clear we weren't really very attracted to each other. She was very slightly plump, but it was more that she was just plain, while I in turn clearly wasn't her type. Still, we hung out and walked around a park on a cloudy day, then sat a while on a picnic table. I remember her telling me a story about her and two girlfriends having sex with a guy they knew as a treat to him, she didn't reveal many details but it definitely turned me on. I got behind her on top of the table to rub her shoulders, she neither responded nor told me to stop, and after a while I asked her if this was ok. She said she didn't care, and that "when I'm not into something I can just ignore it." I asked if she did that on dates often, and she said she did, it's easier to just let someone touch her than stop it.

    I said I didn't want to offend her and wanted to know what her limits were, and she just said her clothes have to stay on, but otherwise she didn't care. I confirmed that this could go as far as a guy getting himself off, and she said that happened and it's just "what they do" in her words. I took that as an ok, and started fondling her boobs and like she said, she just ignored me but didn't tell me to stop, she just kept looking out at the trees around us. No one was around and it was getting slightly darker, so I took a greater risk and pulled out my hardening dick, sliding it against her face. She didn't move at all, so I kept stroking and sliding more, while my other hand held the other side of her face. "Turn here" I said as I shifted her head slightly more to the right where my cock was pressing into her cheek, and she just let me move her head without resistance. The angle was still awkward but I was getting close so I stood up on the seat, feet either side of her hips, and held my dick right in front of her face, pumping into her tightly closed lips. She wasn't giving me any action, but the sight was incredible and I quickly started cuming over her face, barely able to keep my balance standing as I coated her face with white ropes of semen.

    I sat down and rested, and she still just sat there expressionless. I thanked her, again without response. I finally asked if she wanted a ride home, though she had walked there and said she was less than 5 blocks away from the end of the trail, which wasn't far. She shook her head no, and got up. She walked passed my car, I said good night, she kept going. Never heard from her again.

  • My Mentor

    There is poor, and then there was us. Abandoned by our father, we were in a government facility for women and their children. No toothpaste, no toilet paper. I was given someone else's clothes. I was embarrassed.

    A man, who heard about our 'predicament' at his church sent some clothes and bathroom supplies. He sent each of us new shoes. He sent money for food. Everyone in the facility had to provide for themselves, the facility provided a roof. We were the chosen ones for this man, he never met us.

    My mother got a job at the high school as a janitor or 'cleaning lady'. We were embarrassed. When we got old enough we got small after school jobs, until we were able to rent an apartment. Once we left the facility the man's money ended, went to some other woman still there.

    I worked as a waitress in a Chili's and made decent tips. I finished high school and went to work at a business looking for a clerk. I was tested there, and was put into a development program. Eventually earning a college degree. With my salary our lives were better, but not good enough for my mother to quit her job.

    As a professional I saw a different world. One day a woman there asked me if it was luck, or if I was Mr. T's special one. It was then that I learned my mother's job, the good luck of the apartment, the job, the scholarship, all of it was him.

    She Whispered Her Body Count The Moment I Entered Her

    So, I'd been chatting on a dating site with this weird woman. She's older than me at 38 and divorced. Anyways, we're on our first date and it's going really well and on our way to the parking lot we start making out and she invites me over to her place.

    I follow her back to her place and she's naked the instant we walk through the front door. I mean like ripping her own shirt off and everything. We end up in the bedroom and I have her hanging off the bed and spread her legs wide and then slip on a condom she hands me.

    I start to enter her pussy and she says "slow, slow, slow, slow, slow". She's wet but freaking tight. I take my time and the moment I'm all the way inside her she says "33". I knew instantly what she was talking about but I asked her anyways.

    She smiles and says "your my 33rd". I laugh and we have some of the best sex ever. When we finish she tells me to see myself out and she will text me later.

    What a freak! Can't wait to fuck her again.

  • Double Standards

    Had a date from Tinder, she was a real hot DTF biracial beauty. I met Tiffany ( I thought it was a stage name) at a local restaurant at the bar. We had some drinks and app and after she came back from the bathroom she was all over me. We ended up at my apartment, and went straight into the bedroom. In a flash we were naked and I had my face between her legs, licking for all I was worth. As I licked up and down as I got close to her butthole, she moved up and I kept licking both her holes. After a few I was eating that ass and she was loving it. She told me to fuck her. I rolled one on and started slamming back shots hard and slipped my thumb in her butt. She was a screamer, and I pushed her face into the pillow to shut her up, because of my neighbors. I didn’t nut when I pulled out so I took the rubber off and asked her for some top. She went down on me and when I was getting close I told her and she pulled away. I told her to take it and she said “ that’s disgusting, no man is cumming in my mouth”.

    I was so pissed, I jerked onto her clothes and threw her out. Fuck, I can eat your ass but you won’t finish a hummer? Fucking double standards!

    Please Don't Tell Anyone!!!

    O-M-G Sunday may embarrass me to death! It wasn't a date, but it was a disaster. We had a family outing at the lake. I caught a ride home with my brother and his family. I am just a 37 yr old guy and I couldn't help it.

    My brother has an extended cab pickup. He and his wife were in the 2 front seats. I had to share the backseat with his 3 kids. Two boys and his 13 yr old daughter. We couldn't all fit and daughter didn't want to sit on her brothers lap. She was wet in a tiny bikini and a towel wrapped around her. She was sitting on my lap. I tried to think of anything else but it happened. She was bouncing around and grinding on my crotch. I wanted to jump out of the truck as I started getting hard. As my dick got hard she noticed and turned around at me with a grin on her face. Maybe it was me but it seemed like she started intentionally moving her tiny ass and grinding on my dick. By the time we got to my house I was super hard. I used my bag and towel to hide it as I got out of the truck. I think she had fun doing this to me! I pray she doesn't say anything.

    Sucker For The Ones That Cry

    I was at this bar when I saw a girl sobbing so I went over. She looked up tears streaming down her cheeks. Well to cut a long story short I took her home. As we walked her hand kept grabbing my ass, I'm in here I thought. Inside her flat she was all over me, fondling my cock her tong down my throat. She was really strong and aggressive and soon exposed my cock and gave fantastic head too. I was allowed to place my hand between her legs, this girl was a dude. In panic I tried to get free but she was to strong. She held my hands above my head as my shirt was ripped open and her teeth bit my nipples one then the other. She moved up sitting on my chest. I watched as she got her dick out and slapped my face with it then ran the tip across my lips smearing pre-cum on them. 'lick your lips lover boy', she demanded. I had always been curious and instinctively did so, my resistance wilting. Her cock was again introduced to my mouth and then I was a first time cock sucker. She was loving it, well that and the dominance. My hands were free and as I pleasured her she removed my pants and lubed my ass. I was assertively coaxed into the doggy position and she got behind me, grabbing my hair and slapped my arse. My cherry was popped and after the initial pressure, in her cock went and I was being fucked. She smacked my bum again and announced she was going to pump a baby into me {a little opptomistic}. She gave it a good go anyway and I orgasmed as I felt her semen decorate me, each jet taking away my masculinity. For about a minute I was there her entire weight bearing down on me then I felt her cock fall from my ass and the she got off. I stayed the night and was woken numerous times to be fucked each time as her whore or as she exclaimed her cock sleeve.

    She's Beautiful To This Mother's Eyes

    Why me? I'm sure I'm not the first one, or the last one. Pregnant. I went to the abortion center, there were four women ahead of me. I hope I didn't look like them. After my interview I was asked to sign papers. An X would do for a signature. Anonymous was the given name.

    I am not anonymous, neither is my baby. Like I said, why me? I'm not old enough to have a baby, much less be her mother.

  • Uneventful Life

    I was a junior in college when the boy I was in love with told me he was gay and moving to New York. I was thirty seven, a nurse when a doctor getting a divorce fucked me and left me pregnant and reconciled with his wife. I decided to keep the baby and raise it. Whatever it was. It was a girl and I named her Christine.

    When Christine was ten I let her go to spend the week with her father and his wife. The most anxious thing I had done. They went on a cruise and she went too, she and her half brother and half sister. I stayed and felt sorry for myself. I went out to eat, and then for the first time since before Christine was born, I went to a club. Met a man at the bar and he came home with me and I had sex again.

    I am now 67, I went on a cruise with a woman friend who is divorced and I let myself be enamored by a man. I went to his cabin. He took his time until he developed an erection and we had sex. His erection didn't come completely down so we had sex again. Then I went to the cabin I was sharing with my friend.

    We arrive tomorrow and go back to my lonely life. I'm glad I decided to keep Christine. It is the only smart thing I have done in my life.