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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 / 41

Injuries Anyone?

Will anyone admit they have had a "sexual injury" at some point in their lives? Not an STD, but an actual injury.

Say mine for example. I was young 20 something and made the mistake of cheating on my boyfriend. The reason I cheated was because of his dick.

Rumors around the workplace were that it was huge! And the rumors were accurate. He pinned my legs back behind my ears and tried to pound me through the mattress with a dick that should have had its own name and address. He bruised the hell out of my uterus! I had to take a couple of days off work and doctors visit. For real I was walking funny, slightly doubled over and holding my belly.

Also back in high school a friend of mine had an injury when she was 15 or 16. She let a 20 something guy fuck her in the ass. There was some tearing and bleeding. Try explaining that one to your parents and the doctor.

Anybody else?

5
# 73569 - by Me / September 18, 2024
    • - Dating Disasters -
    Straight Female / 34

    I Made My First Boyfriend Look Bad

    We were in the tenth grade and he asked me if I wanted a ride home on his bike. I was prohibited from riding a bike. Period. I had to say no, and line up for the bus. He followed the bus all the way to my bus stop, and rode beside me while I walked to my house. Before I went in he popped the question 'did I want to be his girlfriend?'

    He kissed my lips. I walked into my house and screamed. I was his girlfriend, I wasn't going to die virgin.

    My parents didn't agree. Certainly not my father. My mother reminded him of what he did when she was sixteen. Boyfriends are trouble. No. That was the consensus.

    The next day I let him give me a ride. We waited for the bus to get to my stop, then I walked home.

    Over the following weeks I disobeyed more and more, and I let him take my virginity. He betrayed me, told his friend. Seven weeks from the day he asked me to be his girlfriend. Not a record by any imagination, too long if you measured how long the other boys took to pop their girlfriend. Too long.

    That's what one of my friends told me, she hung out with an upper classman. Why didn't I think of him? Now he's a loser.

    0
    # 73481 - by Jean / September 13, 2024
    - Dating Disasters -
    Straight Female / 28

    Fitting In Ruined My Life

    The one time I tried to fit in ended in disaster. I was always very shy and backward. I failed miserably at college and dropped out after two years. My parents were furious.
    I got a job waiting tables at an Applebee's. I sucked at that as well because I couldn't be outgoing. The main bartender, Amy, was a beautiful and popular girl maybe a couple years older than me. I knew she had a boyfriend, he was in the restaurant often. He was black. Amy is white.
    One evening she nearly made me faint be really talking to me about stuff other than work. I was so excited when she asked me to come over to her house after closing. Amy said her boyfriend had a cute friend who would be into me.
    When i got there I was quite overwhelmed. Besides Amy's boyfriend there were three other black guys there. The music was loud, everyone was drinking and smoking marijuana. I had a drink but passed on the marijuana. As I watched and listened I got an even bigger shock. All four of the men lived there with Amy. And from the way they were talking to her, and touching her, it was obvious all the guys had access to her, sexual access.
    I was sandwiched on the couch between two of the guys as Amy sat on her boyfriends lap in a recliner. At one point Amy went to the kitchen. A minute later her boyfriend followed. They didn't come back for like 10 minutes and the guys were starting to get touchy feely. I got up and walked into the kitchen. I froze in the doorway. Amy was naked, on her knees sucking her boyfriends cock. When she noticed me she briefly stopped, giggled and told me to get another drink. She acted like it was nothing and went back to sucking him. I turned and had intentions of heading to the door. I nearly knocked down one of the guys. He grabbed me around the waist to keep me from falling. Quickly his hands found their way to my ass. I tried to push him away then I heard Amy's voice yelling at me to "relax". I calmed down and the guy led me back to the couch. Amy and her boyfriend were right behind us. Her boyfriend stripped down and sat back in the recliner. Amy got down between his legs and started sucking him again. At that point the guys were all over me. Being pulled in all directions as my clothes were removed. I wasn't very sexually experienced and definitely not ready for this. My legs were pulled apart as one of the guys got in place and started guiding his cock inside me. I panicked as I saw he wasn't wearing a condom. When I asked him to put one on it sounded like everyone in the room broke out laughing. I just kind of laid there as the guys took turns on me. The biggest surprise was when I looked up and Amy's boyfriend was kneeling between my legs. I looked around the room and realized Amy wasn't there. All four guys were concentrating on me. I didn't see her again the rest of the night. The four guys fucked me on the couch and floor in every position you can imagine. When they were finally done I was a mess. Cum in my hair, all over my body and unfortunately several times they didn't pull out. I wasn't on birth control.
    They let me gather my clothes and use the bathroom before I left.
    The next day Amy actually had the nerve to ask me if I had fun. Even told me the guys enjoyed themselves and wanted me to come back. I not only declined I quit my job. As a bonus humiliation my period didn't come a few weeks later. I was very pregnant and ashamed to admit to anyone it could be any one of the four guys.
    I now have an 8 yr old son, a black son. I love him dearly but my family didn't understand. Pretty much disowned me. I am now living on government assistance and never recovered from that night of trying to fit in.

    3
    # 73408 - by Girl / September 9, 2024
    • - Dating Disasters -
    Straight Female / 24

    He Doesn't Want To Get Married

    Why I accepted the free ride from Dallas to L.A. runs through my mind over and over. He drove, a man thing. Letting a woman drive was beneath him. So we drove 8 hours and we stopped to overnight at a Holiday Inn. He had his room, and I had mine. We went to get a burger, he went his way and I went mine.

    He called at three a.m. Did I want to sleep with him? I made a mistake, I said yes, and now I can't just walk away from it. He left his swimmers in me and one of them broke my egg's defenses down. Now I'm pregnant.

    And no, I don't use birth control, beyond keeping a man out from between my legs. Obviously failed the test,

    0
    # 73354 - by Vanessa / September 6, 2024
    - Dating Disasters -
    Straight Male / 31

    I Watched My Highschool Gf Get Spanked

    This was a long time ago but honestly I think about it all the time. My highschool gf was controlled by her step-dad. Like she would tell me stories and I wouldn't believe her. Looking back I should have told someone but I was just a dumb kid.

    Anyways, one night we came home from a football game late and he was waiting on the front porch of their trailer. He's drunk and starts yelling. I'm scared out of my mind. Next thing I know he's bending her over his lap, pulling up her cheerleader skirt and begins to spank the shit out of her.

    I literally run to my car like a coward to the sounds of her spanks and cries. We dated for a few months after that and broke up before the end of senior year. No idea where she is now.

    0
    # 72991 - by AverageJock / August 19, 2024
    • - Dating Disasters -
    Lesbian Female / 30

    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.

    2
    # 72261 - by Carmen / July 6, 2024
    - Dating Disasters -
    Straight Female / 24

    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.

    2
    # 72184 - by Deb / July 2, 2024
    - Dating Disasters -
    Straight Male / 52

    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.

    1
    # 72163 - by Jim / June 30, 2024
    - Dating Disasters -
    Straight Female / 25

    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.

    2
    # 72117 - by Lai / June 27, 2024
    • - Dating Disasters -
    Bi-Sexual Male / 33

    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.

    1
    # 72116 - by LuckGuyNumberFive / June 27, 2024
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