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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 Male / 23

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!

0
# 71594 - by Not_Shy / May 24, 2024
    • - Dating Disasters -
    Straight Male / 37

    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.

    0
    # 71530 - by Me / May 20, 2024
    - Dating Disasters -
    Straight Male / 22

    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.

    0
    # 71527 - by Bob / May 20, 2024
    • - Dating Disasters -
    Straight Female / 18

    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.

    0
    # 71247 - by Not Anonymous / May 2, 2024
    - Dating Disasters -
    Straight Female / 67

    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.

    2
    # 71098 - by Glenda R.N. / April 20, 2024
    • - Dating Disasters -
    Straight Female / 24

    Fantasies Suck

    I spent Saturday morning driving to a nearby town where I wouldn't be recognized and buying one of those Plan-B Pregnancy Prevention kits. Heres why...

    Getting married in 2 weeks. I intend to be faithful to my husband once married. But I have been thinking I am young and haven't had many adventures (of the sexual kind). So a few weeks ago I made up my mind I would try and make 3 sexual fantasies come true before getting married.

    1. Sex with another girl
    2. A "BIG" cock - all the boys and men I have been with were average to small
    3. A 3-Some

    The sex with a girl was easy. It maybe took 15 minutes on a hook up app to find a cute girl. We met and got as hotel room. I had a lot of fun that night. One down.

    Then I turned my attention to finding a guy with a big cock. Took me a week but I finally made a date with an attractive guy. We met face to face in a hotel bar 2 days ago (Friday). I was a bit nervous because he was black. Yes I am white. I am not racist but I had never had sex with a black man before. His pics were impressive and claimed the huge cock hanging between his legs was 10 inches long. We got a room and it was off to the races. As we undressed I was impressed, he didn't exaggerate. His cock was so big and thick I barely got 4 inches in my mouth and my jaws were stretching. When it came time to fuck I insisted he put on a condom. He didn't have any but I had thought ahead. I opened a "magnum" condom and tried to put it on his cock. We both kind of laughed. It looked like a hat on that big thing. I finally agreed to let him fuck me bare if he would pull out. SILLY GIRL! We used a ton of lube and finally maybe 15 minutes later he had worked all of his cock inside me. I made him take it easy at first. We went through several positions and eventually he was pounding my little pussy. My favorite was missionary. Every time he slammed into me his balls slapped against my asshole! I was amazed at his stamina. We fucked for over an hour. He was laying on the bed and I was bouncing up and down on his cock when he reached up, grabbed me and pulled me down for a kiss. During the kiss I felt his cum unloading inside me. I panicked and tried to get off him, he grabbed my hips and held his cock inside me.

    Now you understand my problem. If he were white I could take the chance, but if I pushed out a black baby I wouldn't have an explanation.

    I think I will skip the 3-some.

    4
    # 70832 - by SillyGirl / March 31, 2024
    - Dating Disasters -
    Straight Female / 25

    Maybe Some Other Girl Will Read This And Keep Her Pants On

    As a junior in high school I was at a lake party I didn't have permission to go to. I was supposed to be spending the night with a friend, but we had always intended to go to the party. I got screwed that night, loss of virginity, and got pregnant. The boy was a college student, and he was very upset that I was pregnant. We both knew that the consequences were going to be severe.

    We were married without much ceremony, there wasn't a party. The ceremony was at the church with the pastor and our parents, we came, we got married, and we left. He had to go back to school and I had to finish the 11th grade. In our school pregnant girls were sent to another school for troubled teens. Because I was married and because my parents intervened I was allowed to finish the 11th grade, but really because I would be done before I really started to show.

    The 12th grade I did remote under a program for students who were to ill to attend. I had the baby in November and my mother placed all the responsibility on me, except for the bills. It was hard, I tried breastfeeding for several months, but quit after four months. I felt really bad about it, but i couldn't keep up with it.

    My husband graduated from college and I finished high school. He went to work and I stayed home with the baby. I wanted to go to college so the following year I started taking courses at the community college to get some hours. I was still living at home, and my husband lived in an apartment complex. A friend of mine told me that he was seeing her sister on the side. We got divorced.

    As long as I was taking at least nine hours a semester I didn't have to work. My mother took care of my son while I was in school. Nine hours a semester was going to be a very long time before I could get a degree. I talked my parents into going full time, and use the child support to pay for a sitter.

    I finished my degree, got a full time job, tried living alone with my son, but I ended up back at home. I couldn't make it alone. I heard that my ex had broken up with that girl and I asked him to let us live with him. We didn't have to be married, just let us live there. One week is all it lasted before I was back in bed with him getting pregnant again. We got married again.

    I am now older and wiser and I believe I'm a good wife and a good mother. I know my husband goes out with his friends and sometimes they go looking for girls to pick up. He tells me it's a guy thing. He never really had a wild time, well I didn't either. Him picking up a girl at the dance hall isn't what bothers me, it's having sex with him afterwards. He says he takes precautions, but the worry is still there.

    I turned 25 last week, I feel like I'm 45. My son is going to be eight and our daughter is going to be two years old.

    2
    # 70797 - by Susan / March 29, 2024
    - Dating Disasters -
    Straight Male / 32

    It Always End The Same

    I was born with a tiny cock, perfectly formed but only 40 mm long. I have no problem picking up girls however when they see it they start laughing. Some just make an excuse and leave, some give me a pity wank but the worst are the ones who tell their friends who just want a look. I met this girl who decided to humiliate me, taking photo's and posting them. She gave me a pity wank which was ruined and scooped up my cum and made me swallow it. I spent a coupe of dates on the end of her strapon, she said I ort to be caged but didn't think they made them that small. On one of the dates she brought her friend who thought it would be fun to knee me in the nuts repeatedly whilst I took the strapon up my ass. They left me broken and upset. Maybe that's as good as it gets for me and it's ten times better than girls dropping my pants to look at the smallest penis they're every likely to see, making derogotry remarks and laughing at me.

    1
    # 70496 - by ??? / March 8, 2024
    - Dating Disasters -
    Straight Male / 32

    Used Ex Returns

    My girlfriend and I having been dating for over 5 years now but a few months ago we decided to separate, and we also did so on good terms. We had no contact with eachother for 3 months and it felt good to finally move on! I even started talking to a few other women. About a month ago she came back into my life and we’ve been seeing eachother casually ever since. We’ve been open and honest with one another about our time apart, and it turns out she was seeing another man just 2 weeks after we separated, which I found strange considering I hadn’t moved on for at least a month or more.

    She initially described him to be a mistake and rebound, and that she was glad to have me back in her life. We’re on track now to possibly get back together, but recently she described the nature of their relationship together.

    She mentioned previously mentioned he was “inconsistent” but upon elaboration it turns out he was actually just seeing her for sex and only sex. Legitimately the only times he would message her would be to come fuck her, or to take her on a date and then fuck her in his car. Apparently he was “selfish” and upon elaboration that was because on longer drives he would want her to give him road head, which she apparently obliged each time. When she described him to be “disrespectful” it turns out it was because he stopped returning her calls after she complained about not being in a relationship with him.

    As I reflect on this I can’t help but think I’ve been played, as she’s been fucked, used and dumped like a cheap slut, yet I’m the one stuck with potentially wifing her up. Like I mentioned we’re in a pretty solid track towards marriage now and I’m not sure how to think or react. I love her but to me, her value as a woman, wife and life partner has plummeted beyond saving.

    4
    # 70449 - by Dilly / March 5, 2024
    • - Dating Disasters -
    Straight Female / 19

    My Dream Guy

    I met my dream guy about a month ago. He is hunky, muscled but not overly so, very firm, fit body, gorgeous face too. Not too hairy but still very masculine. On our second date he was feeling my bare tits under my blouse and bra, on the third date I let him rub me off as i took off my panties, his hand up my skirt which he followed by giving me the best oral I've ever had. I agreed to a date at his place the next evening. He had food brought in and after we ate, I went into the bath and stripped, coming out totally naked. I have a nice body, middle tall 5ft. 7in, I have only B cups and a small b at that, I have been told my legs and ass are very nice too. I came out with my trimmed brown haired bush and little tits, we kissed, I straddled his lap and grinding on him, then basically gave him a lapdance. I pulled off his pants then his underwear and . . . I was stunned. I could barely see his cock in amongst his trimmed hair. Only the head was protruding and it was tiny, very thin. I tried to play with it, and got it "hard". That was only a little over 2 inches long. He was very thin.

    I was disappointed and I think it showed. He was apologizing and I just said nothing. I took it in my mouth, sucked him, he came ( a lot too, not sure how that happened with his tiny little balls) and I swallowed it. I kissed him, pushed his head to my V and he began taking me to the edge again. After I came a couple of times, I saw his little thing was hard again, and I pulled him up between my legs. He put it in, and pumped and to be honest I felt nothing. He shot his cum basically all over my inner lips, though I was sure some got in me.

    For some reason I repeated this with him about 5 dates. My friends were all asking how big he was and I wouldn't tell them. I can't have sex with someone who can't penetrate me. I wanted to date him but couldn't bring myself to not have sex as I didn't want to humiliate him. by the way he's never even said anything about his being so small.

    Turns out, I'm pregnant. I've not been with anyone else in over 4 months. I cannot marry him. I can't even think about going through my life with that little one I can't even feel, pounding away at me.

    2
    # 70286 - by Nikki / February 26, 2024
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