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.

She Liked Me, I Liked Her Cousin

During my junior year in high school I worked at discount store (think Wally World or the store with the Bullseye. I was befriended by this mother who worked in the clothing department. She thought that I was a sweet guy and decided to set me up with her daughter who is also a junior.

I am shocked when the cutest red head arrives at my table & blushes. I have died and gone to heaven. Was Karen's picture of Erin outdated? This babe identified herself as Erin's cousin Katie (sophomore) and that Erin was in the restroom dealing with her period. What the flip flop? It was explained to me that since Erin & I never met before, Katie came along to make sure Erin was enjoying herself.

I so wanted to leave but I couldn't do that on my first date. Both girls were very nice. There was more chemistry between Katie & I. I had to be nice and respect them equally.

Right before I left, Erin pulled me aside crying saying she's sorry but she didn't think I liked her as much as she liked me. We hugged & I left.

The next night, Karen pulled me aside and ask me how the date was. I told her that it was a very good date but it wasn't going to work out with Erin. Karen told me that I should ask Katie out & I said I couldn't do that to Erin. Actually, the truth was I did not want to have Erin to go on a date with Katie and I.

A couple weeks later, Karen gives me Katie's number. The next afternoon, I called Katie to ask her out and she told me I was too late because she found another guy.

A year later,she ended up working in as a cashier. From time to time, we spoke. She told me one night that she had a question for me the next time we worked. How lame could I be? I asked Gail out the next day.

She was walking to my locker to apparently to me out but I was holding Gail's hand. Katie dumped a can of soda on my head.

Gail was a nice girl but with her older sister being a teen mom, she refused to kiss me. At prom. Gail broke up with me & told me I was too cautious and she was going to party with Andy who was her new BF. At that point, I had been gone from that employer for a month. 2 weeks later, I bumped into Katie and she asked me how things were going with Gail. I told her that Gail dumped me.

Katie nudged me and said we had bad timing since she had a BF.

I decided to bypass college by nearly 4 years. I walked up to meet my R.A. and Katie saw me & hugged me. 5 minutes later, Katie is knocking on my door. Fortunately, my roommate who I had yet to meet wasn't coming in until the next day. Katie wanted us to get to know each other more. I smiled and hugged her. Katie shocked me. "Mickey, I know that you'll probably shoot me down, but please kiss me and promise me you won't date another girl." I partially shot her down and told her that when we both were ready , we will have our first kiss together. The next day, I met a sexier redhead named Tracy. She invited me to her room to hookup. I respectfully shot her down & told her I already had a GF. She told me it was my loss.

10 minutes later, I ran into Katie. Katie says, "I heard you have a GF, care to tell me about her?" Before I could respond, she chuckles and then kisses me on the cheek. 2 days later, she asks me out. The next weekend when my roomie was gone, we got into a 69. We lasted for 14 months because I was not in a position to move to Japan with her nor did I want to hold her back. Katie & I kept in touch for a few years and I supported her when she came out as being bi. Sadly, I never saw her again because a drunk driver took her life.

  • Rest Room

    I met a guy on Tinder who was forthright and blunt. Within a couple of minutes I'd agreed to a meet. We met at a local beauty spot and as I pulled into the car park I saw he was already there. As soon as I got out of the car his hands were all over me. I objected but he called me a slut and I melted. I kissed him as he exposed my stocking clad legs and lace panty ass to whoever cared to look. He was groping my cock as a pair of hands squeezed my ass. I looked back, a stranger, he grabbed my head and tonged me. My date pulled down my panties and started sucking my clit and the other man decided I needed some dick. He dragged me into the woods and bred me doggy style as my date watched. There I was with this spent mans weight on my flank as his limp dick fell out of me and then his semen running down my thigh. He offered me his cock which I cleaned and he left. My date had left too so I went to the rest room to clean up. 'What have we here', one of a group of men barked. My skirt was lifted and the five men spit roasted me for the next hour or so

    Ugly Girl I Used

    When I was about 30 I had a date with a woman a few years older than me. She wasn't very good looking, and constantly had a sour look on her face. Wasn't much of a talker either, and we didn't have much in common. But she must have been lonely because she asked me to stay and watch a movie. I half wanted her to throw me out, so I mentioned that I was horny, she said she wasn't going to have sex but I would do "whatever" and she wouldn't care. So we started up some movie, which also didn't interest me much. She was lying on the floor with a pillow propping her up to see the TV, and I sat behind her. About half way through I unzipped and started stroking myself just inches from her head, at first I wasn't sure if she noticed but eventually it was clear that she knew what I was doing and was just ignoring me. I eventually just barely touched her face with my hard cock, and then started jacking really hard while she just watched the movie and ignored me. Finally I shot about 3 gobs of cum onto her face, all landing perfectly across her cheek and lips. She still completely ignored me while I ejaculated, finished my stroking, and wiped another drop of cum onto her chin. She even ignored that for a while as we continued the movie, though occasionally reached up to wipe her face as the cum started to run. When it was ending I found that seeing her cum-soaked face made me horny again, so I jacked off again, added a few more drops onto her face as she silently stared off into the distance. I zipped up again and said "thanks for the movie." "Glad you liked it." She saw me to the door with a sullen look on her face, cum still hanging onto her face.

  • The Package Looked Good, The Gift A Disappointment

    Pre covid we hired a temp for a couple of weeks. Her claim to fame was that she 'modeled' for Victoria Secret. The opportunity arose and she shared herself in the sac. A looker for sure, but not worth the effort. Goes down as one of my more disappointing opportunities in the sac.

    The Price You Pay Losing Your Virginity, It Cannot Be Regained

    I spent a week at a church retreat. Other girls there went because they were going to regain their virginity. It really messed up my mind. How could girls that young lose their virginity, but I had heard of some girls experimenting. But, how is it possible to reverse that? I believe in God, but miracles require some miracle event.

    Later, when the day came that I lost my virginity I thought, I can always get it reversed. But, nothing reverses that. I had to settle by getting married. A high price to pay for losing your virginity. I did love my husband, but I was 19 with all the burdens of a house and wife.

    So now that I've been married, a mother, older, I don't believe you can regain your virginity, it's a one time only thing to lose. A previous thing really, the boy or man could care less, getting a virgin girl is another feather in their cap. That's why I caution girls and encourage them to wait. That and you can get pregnant,

  • Fucking An Asian Ragdoll For Months

    Over 10 year ago I met an Asian woman through a personals ad (these hardly exist anymore, having been replaced by apps). She lived way out in the suburbs, with two young kids, and we clearly had nothing in common; she could barely even speak English. But she invited me to her house repeatedly and kept calling me to ask when I could come over again. She couldn't get out on dates because she had her kids at home and just worked a retail job which must've just barely covered the bills. She was very small, maybe only 4'6, with only slightly brown skin and jet black hair. I didn't know what she saw in me but eventually asked her when she last had sex, which she said had been over two years ago when her husband left her. I asked if she missed it, and she just said without enthusiasm "you can do that."

    We went into the bedroom and I asked her if she was sure, she said yes so I pulled off her sweatpants and panties and laid her back on the bed. She had jet black hair below too, completely unshaven. I just unzipped and took out my dick, rubbing it against her clitoris for a minute, which seemed to not move or interest her at all. She said "put it inside" and so I did, sliding deep into her wet snatch. She simply laid back like a passive rag doll while I fucked her for several minutes. Her head only came up to my chest so when I leaned forward I was basically just staring at a pillow and the wall. I almost felt embarrassed when I finally came because she didn't seem to get any pleasure out of it and I was just whimpering away like a baby, but it was very fun. I asked if she could suck me but the cum disgusted her so that was a no-go.

    I soon left, but got invited back many times for months. Sometimes she would suck me to get hard, but then wanted PIV over and over again. It threatened to get boring, except that she would let me fuck her in any room of the house, in any position I wanted; I even got her to do it in the garage once, which was empty since she couldn't afford a car (she asked me for rides to and from work at times, though usually she took the bus or carpooled with co-workers). I usually asked for missionary position or fucking from behind as she laid down on her belly so her small curvy ass stuck up toward me. Only occasionally did we try something different; I once asked to fuck her modest tits, which ended with me jacking off on her face, which she found revolting until she rand to the bathroom to clean it off. But she kept inviting me back again. A couple times when I picked her up from work I managed to even stop in a park and fuck her on the grass in the dark, but this was usually too risky. I slept over a few times, but the majority of my visits were 10-15 minutes of me coming in, pulling her pants down, bending her over or laying her on a couch or bed, and slamming her pussy until I ejaculated, then leaving.

    After a few months it dawned on me that she was trying to get pregnant with me, perhaps to trap me into a relationship. But she never asked, and I didn't tell her, that this couldn't happen because I had a vasectomy. I kept fucking her for the better part of a year, then she stopped inviting me over. I found out years later that she did get pregnant by another man but I don't know how that worked out for her. I was glad to use her while she thought she was going to use me.

    I'm Going Straight,

    During my years in the service I became involved with another female officer. Not my first affair but my strongest. After I left the service I vowed to go straight. I met a man who fucked me and put me in my place and pointing to me he told my ass belonged to him. I went along, did what I was told, got the ring and the wedding gown, and laid down to get pregnant.

    Two years later, under pandemic rules I fell for a girl who was babysitting my daughter. The affair became very serious, and my husband found out. He didn't yell or scream, he spanked me instead giving clear instructions, orders, to stay away from the girl.

    Going straight has it's price, I can manage it. Maybe I'm lucky, my husband knows how to keep me from going back. I know that. That's why I married him.

    Vapid Sucker

    A few years ago I was in graduate school but hanging out at times with some undergraduates in a student group. One very young woman, Laura, seemed immediately drawn to me for some reason, and obsessively sat near me and wanted to talk with me alone as much as possible. I humored her, but honestly didn't find her very attractive and she seemed rather shallow to me. I don't think she was objectively ugly--she was thin with dark hair, white, somewhat angular and maybe a little awkward but otherwise somewhat average looking. I think it was more her personality and her obsessive desire to talk about everything that came into her head that turned me off. Still, it felt good to get some attention, and so when she asked if we could watch a movie together, I was fine with that.

    She came to my house with a DVD, and we sat through a decent film she had picked out, some romantic comedy whose name I don't recall. We sat on the couch just barely touching most of the time, but I could feel some vibes between us, she definitely wanted something to happen. Eventually I held her hand and she began to lean on me a little bit. Feeling any woman that young that close was certainly turning me on, and about 10 minutes later her hand wandered across my legs and felt my rigid bulge, which she began to gingerly brush against. I stopped the movie with the remote and said that this felt good. Soon she turned her mouth right up to my ear and asked "do you want me to give you a blowjob?" I said I wasn't expecting that, but didn't want to turn her down. She slipped lower on the couch and I assisted my cock out of the zipper so she could start bobbing her head up and down my shaft. It was the first blowjob I had gotten in my new place and it felt very strange to look around at my familiar setting at the same time I was getting this unasked for pleasure. I only gently caressed her back, half-expecting her to stop and give up or ask for something else, but she just kept sucking and in less than five minutes I suddenly let go into her mouth. She swallowed my cum, then sat up and leaned against me again. We finished the last half hour of the movie, hardly saying anything about what we had just done. I turned to her and admitted that felt good, and she again caressed my legs and discovered I was hardening again. So I got a second blowjob! This one took much longer, and I actually got a text message in the middle of it and picked up my phone to answer it, this didn't seem to bother Laura at all and she just kept sucking me like she didn't have anything better to do. I realized at some point that I was actually somewhat bored, and wasn't sure if I wanted to have her around anymore, but I was curious how this would end so I let her stay at it. I even got soft briefly but she kept sucking slowly and soon I was again rigid. At least a half hour passed silently, during which time I again picked up my phone a couple times to do something online. This was out of her sight as she was firmly in my crouch from the side, but could probably tell what I was doing if she was paying attention to my movements. In the middle of looking at something on wikipedia I could feel I was going to cum again and stopped for a minute to just stare at the wall ahead of me while I ejaculated into her mouth.

    She was pretty good at fellatio, but frankly boring to talk to, and I felt I could never live with this woman, so I didn't encourage a relationship. She soon drifted off without animosity and I hope she found someone who she matched with better.

    I Am Hurting, Ignored And Unwanted, And Alone

    I started getting urges. They became more and more intense and my mind couldn't leave them alone. My life with my wife became more and more difficult and she offered divorce as a solution. These urges became so strong that at one social outing while out of town I met a man and I acted on these urges. The encounter, I'll call it that, was sexual, aggressively sexual and I found out that in a test of dominance I failed.

    These urges come on without warning. I can't resist them and I find men for my sexual outlet. I find these men on the internet. Meeting in motels and other places. Sex, it's just sex I tell myself, then why do I want it so bad. I met a man, a man who had been a career naval officer, it took me a second to realize that with that man there would be no contest on who was dominant. He took away any illusions that I may have had. I found out what homosexual sex was, when you don't hold any cards. I can't let go of it, I can't stop from thinking about it, I reach out to him but he ignores me.

    I haven't tried to find anyone else since that night, I am depressed and sullen. I tell myself it is sex, just sex, isn't it? But it's not. My gay sex email won't ping, there is only silence. The internet is there, but it no longer interests me. I feel alone. I wish that I hadn't divorced my wife.

  • Stay Away From Crazy Girls

    So I was hooking up with this chick I met on Tinder. She was decent-looking. Tan, blond, nice ass but small boobs. It was going all right at first. We were making out at my place, and out of nowhere, she asked me if I would buy her something she wants. What she wanted was a new iPhone. I first made sure that she wasn't joking then told her that she was being ridiculous.

    The argument that followed was like this
    Me: We only met a few hours ago and you want a new phone????

    Her: That's only fair, you want sex from me right?

    Me: I'm sure sex with you is not worth a new iPhone.

    Her: Wow. You got some nerve to say that. Dude, you're not even 6 feet tall but I still agreed to meet you. You should be thankful that you even got a chance to kiss me.

    Me: I'm sorry what???

    Her: You heard me. If a girl is willing to kiss you then you should spend some money on her to make her feel important.

    Me: First of all I don't have that kind of money lying around to spend on a girl I just met. And if you want to feel important by getting free money and g*fts then go and start your OF.

    Her: I can do that if I want and I'll make more money than you could ever

    Me: Good. Go and become an online whore for perves if that makes you feel important.

    Her: How dare you call me a whore? God, you have such small dick energy.

    Me: Oh you believe in energy as well. Why am I not surprised?

    Her: Shut up. The only reason I met you was that you looked rich. Otherwise, I wouldn't even have looked at you twice let alone have sex with you. I'm sure you got a small 2-inch white dick and can't even get hard. I'm gonna go and find myself a nice tall black guy and then I'm going to ride his 10-inch long black dick while you stay home and keep jerking your small dick to some whiteboy porn.

    Me: Haha, You think you can be like one of those girls in those videos? Those girls are drop-dead gorgeous not basic like you. You barely got any tits. The only dick you are meant to ride belongs to nasty-ass hobos living under a bridge.

    She got mad and started throwing my pillows at me. Then she kicked my table lamp which broke and then she ran away.

    Crazy entitled bitch.