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.

Would You Date Me

So a few years before meeting Linh, the woman mentioned in another story here, I was in a different city walking down the street from a friend's house back to mine on a hot summer day, when a car full of African American women a few years younger than me drove by. They shouted at me and asked if I would date one of their number, a silent larger woman named Nelly. Presumably Nelly had been just saying that she couldn't find anyone to date, and they took her seriously by asking the first man they came across. I said I might, and soon exchanged numbers; I said I was heading home but they need to give me a few minutes before I could meet her (honestly, I needed the bathroom pretty bad). They barely gave me enough time before calling me, and soon I agreed to a movie date in my house with Nelly. I was an avid movie fan and watched 1-2 films a night on video when I could.

One girl came to the door with Nelly to scope out me and my place, but I made it clear she couldn't come in, she admonished me to "be good" to Nelly and said something to her about using her privacy to the fullest, then we came in and after getting her a little water and a snack we sat down to a movie. I tried to talk to her now and then but she was pretty quiet, and seemed embarrassed to be here with me, so it was hard to tell if she thought I was being serious with her, or just taking advantage of her, or perhaps only pretending to be interested to spare her feelings. At one stage in the movie--Woody Allen's "Mighty Aphrodite" Allen meets a black prostitute who gives great blowjobs, and I asked her about that afterwards, whether she gave blowjobs on dates. She smiled and said sometimes, and again seemed slightly embarrassed but I couldn't tell if it was because of my bold question or because she was just shy with men or still feared being teased. I said the movie got me excited so I just had to relieve some pressure, and pulled my hard cock out of my zipper. I said if you don't feel comfortable doing it she didn't have to, I just needed a little relief from the pressure, unsure if I would wait for the erection to subside or jerk off so as to take care of my need by myself. She watched me for a couple minutes and then sat down on the floor; she was so large she couldn't bend over to me on the couch so I stood up and she began to suck me. In less than five minutes I was cumming hard down her throat and screaming loudly before collapsing onto the couch again. She immediately got up and went to the bathroom, and after a few minutes came back through and said she should go home. A minute later she was out the door and I never heard from her again.

  • She Wanted It Without Pleasure

    In my early 30s I put a personal ad in a paper, and got only one answer, from a Vietnames-American woman, Linh, who lived in the suburbs. We spoke on the phone a little, though her English was halting so this didn't go very far. Still, I was in a dry dating spell so I agreed to meet up with her. I came to her split-level ranch house in an ordinary subdivision, where her two young kids (about 1 and 3) ran around the house while we talked in the living room. ordered pizza to eat in the nearly-empty house and I was there an hour or two. It was clear we had nothing in common, and I had no idea why she answered my ad. She was barely over 4 feet high, with short, dark, crinkly hair, and I learned she was separated from her husband and worked a retail job.

    Realizing this was going nowhere, I decided I had nothing to lose and got bold, asking her about kissing; she said that people in her culture rarely kissed. So probably they don't do much oral sex either, then? She didn't know what I meant, so I demonstrated by kneeling in front of her on the couch and explaining about licking the genitals, or sucking the penis if we reversed positions. Oh no, she said, we don't do that. Ok, well that was that then, and I soon went home.

    She called me again a few days later and asked if I could visit. I asked if she was open to trying oral sex, and she said yes. So 20 minutes later I was in her house again, and suggested we try it on the bed. I again first demonstrated by having her sit on the edge and me kneeling in front, but she had no interest in receiving so I asked her to reverse positions with me, after first sucking on her finger and thumb to show her what she should do. It was exciting seeing her kneeling in front of me, but before I went further I asked if she was really ok with doing this. She said yes, so I unzipped my jeans and in just a couple seconds had my hard cock pointing at her face. After a short hesitation she began sucking me, and with only modest instruction about the speed and technique, it was soon feeling fantastic, even though she was clearly inexperienced. She could barely get my penis in her mouth, and at first just sucked on the head, though eventually she could get about 2 inches in at most, but this was enough to feel hot and wonderful. She never looked up at me, and I found myself gazing around this strange situation, getting a blowjob from an Asian woman in a nondescript suburban home with kids in the next room with her estranged husband god knows where. This went on at least 20 minutes, and while it felt good there was no way she knew how to make me orgasm, so I got her on her back on bed so I could lean over her, alternating thrusting into her mouth with pulling out and rubbing my cock over her little face and jacking off towards her lips. I told her I was going to ejaculate but I'm not sure if she understood, she just passively followed my instructions and let me do what I wanted until I suddenly started spewing my white cum across her light brown skin. Her composure instantly turned to one of utter disgust and revulsion, and tried to turn away but couldn't go far with me on top of her, where I continued jerking off my semen onto her until I finished with a beautiful clump of cum streaks on her lips and cheeks.

    I soon went home and figured I'd never hear from her again--but I did! She kept calling me and asking me to visit, when I did when I felt like cumming. Sometimes she would feed me more pizza or some rice dish, always I would have some orgasm, where again she willingly accepted me into her mouth as if she was perfectly ok with it, though getting absolutely disgusted by the inevitable cum. I asked if she was ok with my doing this, and she said that I should do what I wanted to, "even if I say I don't want it." She clearly had a very submissive role in her culture, and I admit I was taking advantage of this.

    She did eventually ask me to put it "inside" and while I preferred blowjobs, I did this too, sometimes fucking her from behind in the living room, even though her children occasionally saw this. Another time I did the missionary position, but she was so small I found I could push her legs entirely over her body to support me, and they barely came to my shoulders while her head was well under my neck and I could only see the top of her hair. It felt to me like I was fucking a blow-up doll who just passively lay back as I thrust into her. She showed no signs of enjoying this at all, but I tried to delay cumming as much as I could to prolong my use of her wet pussy. Finally I ejaculated hard into her c**t, spurting several times before I did some more post-cum thrusting.

    She could never make me cum, but twice I was able to cum in her mouth by pumping her head. This occurred when she called me for a ride to or from work, and I agreed on the condition that she would suck me off in the car. The first time we parked in the far end of a Target lot, and she bent over my pelvis so I could pump her head up and down, then hold it in place while I ejaculated, which (fortunately for both of us) didn't take very long. She quickly opened the door to spit my disgusting cum out of her mouth before I took her home. Another time we stopped in a deserted lot in a city park, only this time a younger MF couple drove in to park as I was pumping Linh head up and down on my cock. She heard the car but I told her not to stop and pumped harder; my eyes met that of the couple, and they probably already guessed what was happening but parked on the other side of the small lot and started unloading their bicycles at the trail head there. Again I had the wonderful feeling of cumming in a woman's mouth while I held her head in place, moving it exactly the way I wanted it to during my intense pulsing, while she pushed away a little but not too hard. Finally I let her go and she sat up while I started the car. We only moved a short distance before she mumbled and pointed to her mouth, so I stopped at the lot exit and put the car in park so she could again open the door and spit my cum out on the ground. I'm not sure if the other couple saw us because I immediately kept going.

    This went on with variations for about 6 months, then less frequently over the next two years. Part of that time I had another American girlfriend, and felt guilty about seeing Linh while dating her, but during a time when my new gf wasn't into sex for a while and I felt frustrated I again went back to Linh for a blowjob or two. Finally she told me a couple times she didn't want to do this anymore so I left her alone.

    Years later I looked her up online, and found that she had gotten pregnant by another American male, but pretended she had been r**ed so she could get money from the county, and had just been convicted of fraud and child endangerment. This confirmed my suspicion that she was trying to get pregnant in order to get support from either me or the government. She never asked if I was fertile, and in fact had a vasectomy years before I met her, so I escaped this entrapment. I'm not proud of what I did with her, but it was also entirely consensual, at least if you can believe her words. Maybe I shouldn't have believed her, but in a sense we were both using each other when neither of us had any better options. She let me took several good pictures and even videos of her sucking me or with cum on her face, so I'll always remember this weird if only partially satisfying sexual experience.

    Wearing My Big Girl Panties

    On a night, when I should have gone home, a man took me to a bar, grabbed me by my pussy and told me I was a fine piece of ass. I tried to get his hand off but he was to big and strong, he had me against a wall, he kissed my face as I shook my head to avoid him kissing me on the mouth. He let go of my pussy, grabbed the small of my neck and walked me outside. I thought for a moment I could run away, but it was a wasted thought. Sex came fast and dirty, with a warning to put out and shut up.

    All these years later I think of that night, the night I was taken by this man. I have asked myself, discussed with more than one therapist, why I am unable to forget it. I have given up, in that sense he owns me, and always will. A woman's place I guess. It comes with the territory. Make lemonade, accept what is real. It's the one way to move on. I want children and a home, with this man.

    Taboo Sex

    My father and mother never married, I was born out of an office romance. My mother was a secretary, my father the boss. For most all of my life I have been a secret to his formal daughters. Two years ago the story got out when my father had a heart attack and both women were at his bedside. It was then that I met my half sisters.

    I won't say I'm a true lesbian, it's just that I like doing it with a girl. My half sister is a lesbian and from the moment we met at the hospital the chemistry was there. We fought it but during the Pandemic we hooked up. It's not like you are doing it with your sister, and we aren't even from the same mother. We knew but did not feel we were crossing the line.

    We have decided to stay firm and we stopped having sex. But I'm missing it. I've never fallen for a girl, but now I have and she is my sister.

    Guy I Met Onlinr Was A Totally Mess...

    I had a very weird experience with a guy I met online we called each other like for a month and video call before we met in real life because I was out of town and during we chatted he was really cute always calling me and looked that he was interested in me and when we actually met it was on Valentines Day and he wasn't at all what I expected. First of all I am 30 years old and he was 40 and he acted really imature he talked like a chatterbox for the entire date, we met at a coffee shop and he didn't look to be that interested in me anymore always checking his phone snd looked distracted like I wasn't even there. He was really short too he lied he was over 1.80m but didn't have that height and he looked kinda gay. I am really disappointed I don't think I will meet again a guy from the internet.
    I was scared at first that he will try to flirt and try to seduce me to have sex with me at the first date but I must confess I was really relieved that he didn't have any of these thoughts. He lied about his job too and I was completely honest about everything.
    I can't believe that these kind of people exist amongs us.

    Wrong Guy. Right Guy.

    For a while I lusted after a guy who was handsome, muscular and always played it cool.
    He was my dream guy. Someone my pussy would become wet to when I saw him. And a guy who I'd mastubated to, imagining him fucking me.
    When we finally got together through a geeky friend of his, I was so excited. We ended up after two dates back at his place, and boy what a let down he was.
    First of all he was a terrible kisser. Then when we got naked, his penis was so small (Not that's bad, but he so bragged about having a huge cock). He didn't like cunnilingus, and I ended up masturbating to get myself off, after he fucked me so badly like a wild man.
    Lastly and weirdly he told me, I'd had the best sex I'd ever experience with anyone. He was just so full of himself.
    A few weeks later I got chatting to his friend, who it turned out wasn't exactly his 'friend' but someone he kind of knew to ask me out.
    He was and is such a nice guy. We got on so well and I found myself intrigued and turned on by him.
    We dated four times before I asked him back to my parents. They were out a football game, so I knew I had hours to enjoy the date.
    Kyle couldn't have been more different. Subtle, funny and sexually amazing.
    He was so attentive to and with me. His cock was so big I had trouble giving him a blow job. Yet he was so gentle and understanding when he first entered my pussy.
    Only when I was comfortable and asked him to fuck me, did Kyle thrust deeper and harder.
    We had sex for nearly an hour, with his mouth, tongue and cock making me climax multiple times.
    It was a thrilling, exhilarating experience and I found myself so sexually alive with him.
    We dated for nearly two years before he proposed to me on Valentines day. And we married a year ago this coming week.
    I love Kyle so much and now wonder, if I hadn't had such a bad date, would I now be with the love if my life.

    Massages Went Awry

    I emotionally connected to my young female massage therapist. She was very revealing with private life and even made a point of saying she was single. I was looking forward to seeing her and asking her out (even if meant I wasn't her client anymore). The next time I went to see her she immediately said she felt uncomfortable about what I said during the last session. I was flabbergasted as I didn't think I revealed anything more personal (actually less) than her. It was an awkward massage. I think I'll quit going to the place. Mind fuck tease.

    I Ruined A Real Princess In High School, Being Sorry Didn't Help

    My father was posted to Latin America during my high school years. I attended a private school which had both expat kids and kids from upper income families. The normal social structure didn't involve expats dating locals. But at a class field trip to the top of a volcano Anabela, the prettiest, nicest local girl sat beside me on the bus, and she politely talked to me.

    At the top, off the bus, I escorted her. She was mine. When we stopped for lunch on the way down the mountain she had to sit by me. I got stares from several of the other local girls, and a couple of the local guys. But Anabela didn't ask for help, so I was able to monopolize her. That day, and afterwards at school, and parties. Like it or not she was my girlfriend as far as the class was concerned.

    She never introduced me to her family, I never went to her house. Her father was a big time lawyer, a plantation owner, and owner of several factories. At a party of one of our classmates I caught her and found a bedroom and nature took its course. I felt like I was king of the mountain, I had gotten the school princess and broke her hymen. She was hurt, embarrassed, ruined. But no one told me. She didn't return to school.

    A couple of weeks later this car with four guys came to my house, when they were done with me I spent a couple of days in the hospital. My father was visited by her father. We left the country. We were gone in a day. From what I found out many years later she was sent to Switzerland for a year, when she came back she went to a small Catholic school. She never married, neither did I. I never spoke to her again.

    Not "Heebert", It's "Aybear"

    While I was living in California I met and got into a relationship with a Japanese American girl from San Mateo, California. Leave aside her politics, I am from Louisiana, she had the California attitudes that made her both sexually adventurous and sexually prude at the same time. Everything was about her, how did she feel afterwards. In Louisiana we have nice girls and they are more into making sure that the guy is taken care of, and they understand that cooking means cooking. This Japanese girl, her idea of lunch was going out.

    I'm not saying that sex with her was bad, it wasn't. It was the focus on herself that drove me away. I literally handed her a mirror and told her to have fun. I'm back in Monroe and I have a nice Cajun girl who talks about kids. Refreshing.

  • Mama's Boy & Clueless

    So I'm not used to sharing stories like these but most people I tell this story to just go, "There's no way that happened. No date can be that bad." But I assure you... It did...

    To start, I get a date with this guy in my class who I thought was pretty cute, seemed pretty funny, so I was pretty happy to go on this date. He says, "Sure I'll setup where we're going. Just dress fancy."

    The day of the date comes, looking great in my open top just in case he gets any ideas, my mom drops me off at his place and drives off. I knock on the door, he opens up looking... fairly casual but whatever. Turns away yelling out, "Okay mommy my date is here, I'm leaving" So right there that was pretty weird but maybe it's some kind of inside joke so I don't think anything of it. The car ride was pretty basic nothing too much to note. We get to the restaurant and the place is pretty hard to get into especially since COVID. Now keep in mind this place NEEDS reservations before anything. We go inside and sit down because no one was at the booth and in my mind I'm thinking he set one up. 30 minutes go by and waiter after waiter walks by and I ask, "Hey, did you happen to get a reservation?" He goes, "Reservations?" So at this point I'm pretty much done with him and before I could text my mom to pick me up he goes "Well there is a Wendy's not too far away we could just go there." Now I'm in a open top dress so I'm just thinking there is NO WAY I'm sitting down in a Wendy's with thing so I suggest just to go through the drive thru. He goes, "Nah, they always get it wrong" So now I'm stuck looking like some kind of hoe in a Wendy's. As we're eating he gets a call, he picks up saying "Yes mommy?" So now I'm really creeped out cause clearly now it isn't a joke. In this time I text my mom to pick me up and after he hangs up we talk for a bit longer. He asks me if I wanted to go back home with him and me holding back laughter I tell him my mom is almost here and to not worry about it. Out of no where he just blurts out, "But I thought you wanted to fuck tonight?" Never once did I mention that I wanted to fuck him in out texts. So now the whole Wendy's is looking at me like I'm some kind of whore. So I just run out and wait for my mom holding back tears.

    But yeah, he texted me the next morning asking me what's wrong... Yeah talk about clueless