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.

In My Affair I Have To Keep The Wife Pleased Too

After working with my boss for a year I ended up going to bed with him. It was my first ever with a cheating husband. Over the next several weeks we had honeymoon sex. I was home, minding my own business, when his wife knocked on my door.

She wanted to know just what were my intentions. She told me how much she loved him and how she expected me to love him too if I insisted on staying in this affair.

Over the following weeks I kept myself away from him. She called, asked me to lunch, wanted to know why I had cut him off. I begged for her to explain something to me, Why did she come to me and guilt me about seeing him, and now guilting because I wasn't see him. She didn't want his feelings hurt.

I can't seem to please her, going home with him or not going home with him? She cleared it up, don't stop seeing him and keep her posted, she doesn't like being surprised.

  • I'm A Baby Lesbian With Training Wheels, And A Total Dick Virgin

    Circumstances put me in this position, 27 and still a virgin. First, I had a real nice boyfriend in high school, but we did not go all the way. Halfway through the 11th grade my family moved to Florida. I was out of the loop there and I didn't identify the Floridians (I was raised in Idaho).

    I go to college, fall for this guy, we are great friends, we hang out together but frankly never date. I tied pushing the door open, wore some less than flattering clothes, talked openly about sex. Nothing, Nada. I don't date anyone else, we were an item on campus. Then in the last semester of our senior year he comes out and tells me he's gay. That I'm the best friend he has and he 'loves', but sex is not what turns him on. He had cheated on me several times with a couple of guys that I also knew.

    I leave school, move all the way to Texas, try out a new life. It's busy, people from everywhere, many Hispanics and Blacks. I didn't realize how much I was turned off by them in real life. I work at a manufacturing company and get promoted rapidly a couple of positions and within a year I'm a Senior Analyst. I start to deal with the upper management types, and learn pretty quick it's an old boys network. I had gotten as far as I would go, so I took a job with a competitor. Same thing, old boy's network. Except much more open about it. One manager tells me that his experience in the Army taught him one thing, don't trust women.

    I try for my third job, except COVID hits, at least I'm not laid off. But I have to take a 15% pay cut. And working from home sucks, I have a roommate, she's a nurse for a pain doctor, so she works at the clinic, I have to drag out and set up my stuff, and close it down and put it away at the end of the day, she doesn't want the dining or living room looking like an office. When would I possibly have a time to date. Things between me and my roommate are getting tense, and she comes to my room and says I should sleep with her, just bite the bullet and sleep with her. She doesn't want another night listening to me toss and turn when she can be holding me and helping me get rid of my stress. After all she is a nurse.

    I asked her point blank, 'don't tell me your a lesbian'. She doesn't admit to it but she does restate she wants me to sleep with her, I needed to be loved and she wanted to love me. My first sexual experience turns out to be with a woman. And it's intense, she is putting me under her wing and needs to kiss me and 'mount' me. The bed is torn apart, the clothes all over the floor, she triggers several orgasms for me and puts my thumb on her clit and my tongue in her pussy and she goes off the charts yelling that she loves me.

    Laying there on my back I realize that I'm never going back to my bed. She is a lesbian and she's going to make me a lesbian too. I'm 27, not once has a male touched my boobs, my ass or my crotch, not once have I had a penis in my face, not once have I had a male's finger or a penis in my vagina. All I have is a knock down love session with my roommate. If I'm not being groomed to be gay, then what it is it?

    There's nothing but kisses and hugs and more kisses and more hugs. Heart emojis. I love you texts and so, so glad that we are both in love. Did I tell her I loved her? She stops at the cup cake factory and brings me a red velvet cup cake with I Love You on it. Whatever repressed feeling she's had are exploding. I can't bring myself to tell her that I don't think I'm lesbian. So I spend the rest of the working from home period playing house with her, washing her panties by hand.

    I'm back in the office with the misogynist management, I keep my mouth shut because if I mention anything I play into their hand. I have to talk, walk the man dating scene. All of it made up. I go home and my roommate listens to me and says that I can stay home, and look for another job. She has enough savings to cover the rent until I find work, When you love someone you support them, with whatever they need to do. Right? Yes, right, I typed up my resignation and let her read it and I told her I love her too. I hope I'm not lying.

    Daughters Boyfriend

    A few years back, I was dating a single mother named Carrie with a girl named Jordan. She was around 32 but recently divorced at the time, thin and beautiful brunette 115lbs 5’4”. Her daughter was early teens with blonde hair and was always energetic. We had to keep her involved in school activities because she hated staying at home. Her daughter and I got along well and I presume this strengthened my relationship with her mother. I’m a runner so I’m thin myself just a bit taller than her mother. For a while we took on gym activities together and got into strength training to encourage her daughters activities. We began to fell out of our routines when Jordan started dating a kid she met in the neighborhood. He was older and a problem I did not want around but blew it off as jealousy as the kid was still a teenager and relatively nice. Her mother would calm me down when we slept together and usually ended with me forgetting after a good blowjob and passionate sex. A year later Jordan and her bf had hit a growth spurt and it looked as if her bf was in college and Jordan was a full teenager and had filled out more than her mom. I always found them kissing every now and then more often in our home and it was rubbing me the wrong way. But her mother assured me it was better to have them close than running off. That is until one day when Jordan was throwing a pool party with her friends I noticed how her bf could not keep his hands and eyes off of her. Everytime he got out of the pool how excited he was and hung. Carrie noticed my frustration and mentioned I should grab some pizza orders from the nearest shop and fill up on gas to settle down. When I came home I placed the food in the kitchen and noticed Jordan was still outside with her friends but her boyfriend was gone and had felt relieved until I caught him balls deep in Carrie in our room. Carrie was arched over looking out her window while Jordan’s bf balls were slapping up against her c**t. I backed away from the door to not get caught when I heard Carrie say “Okay hurry, I think they might come inside for food soon, cum in my mouth quick”, “fuck thank you Mrs.Carr- shhh”. *mmm, sniffle* “gawk, gawk, gawk”. I walked away when I heard grunting and went to the fridge to grab a beer and sit in our living room. When he came down I greeted him but didn’t say much. Didn’t last long with that family to say the least

  • Feeling Very Confused

    Fucking tinder date sucking on my balls getting a taste of my cock when out of nowhere bitch done shoved her finger right up my ass and hard. I jumped up and said nah bitch you gotta go.

    Now i be like was it really that bad?? She sucked a good cock...damn

    The Guy That Has Been With Everyone.

    Everybody knows THAT guy or is that guy. You know that guy from high school that just somehow has been with everyone or has fucked all the girls you ever liked and your like....how??? For me, it was a guy named Pete. I hated this mf. We went to high school together and were kinda in the same circle of friends but he was a friend of a friend of friend. Anyways, if I had a crush on someone, this guy had already been with her or I'd see them holding hands. He wasn't even....that great looking. Girls just liked him. He had every girl I liked, already as a friend on Facebook. The worst memory I have is we were at a party together. There was a girl there I was trying to link up with. We did have a moment where we sat on the couch and talked for hours. The nights ending. She disappeared. I can't find her. I decided to leave. The next morning me and my friends and Pete all meet at IHOP for breakfast. My friends like so what did you do last night to Pete. He said he went home with her and they totally fucked. The worst part was he went into detail while all my friends laughed and high fived him. He was telling them how she would be riding it and then when she got to the tip of it, she would slowly go down but in a waving motion. Then she would get off and blow him. He ended with cumming in her mouth on her face. All my friends were like "yeah!! Hell yeah bro". I was like...this mf. The thing was, girls only wanted to fuck him, not be with him. We still are around the same friends and he's totally different now. He gained hella weight, hit puberty like a mf and works at a gas station. But I hated that guy in high school.

  • I Feel Used And Abused

    Started a new relationship with this guy and things were going great. He took me out on so many dates, showered me with g*fts, like everything to win a girl's heart.

    We were hanging out one night on his bed watching Rings of Power. He turned to me, we started making out, he touched me all over. I just froze, I wasn't ready for it. He started to undress me, then asked, "What's wrong?" I told him I wasn't ready for that next step of the relationship and he got angry. He said I must be in it just for the g*fts and free food, I'm just leading him on. I kept telling him no that's not it, but he was not having it. I caved and offered to give him a blowjob. He replied, "That's a good start," and undid his pants.

    I awkwardly took his cock in my hand, gave it a few rubs. I slowly lowered my head, opened my mouth, and let the tip of his cock into my mouth. He said, "God you're fucking slow," and pushed my head down until his cock jabbed at my throat. He then continued to facefuck me until he came, he shot everything into my mouth. I wasn't ready and gagged, it forced the cum out of my nose. He told me to go clean up. After I washed up, we continued to watch Rings of Power while cuddling, but I couldn't focus.

    It's been a few weeks now and after every date, he facefucks me. I'm just mentally preparing for when he does fuck me...

    Prom Night Is Sacred, Pick Carefully

    I was going to my senior prom. It was going to be the first time I bought a gown. My mother gave me a strict budget, that had to account for the gown, the shoes, my hair and nails. And I couldn't spend a penny of it unless I had a date lined up. As prom approached I was still without a date so I asked this friend from class, Nate. He said he didn't go to those things and I had to bribe him. I told him that it was customary for girls to lose their virginities on prom night, and if he took me to prom he could have my virginity, but not before prom.

    Nate was not anyone's dream date. He was a band nerd, kept to himself and rumor had it that he beat off every night, because he had never had a girl. My mother was surprised, in the negative way, that I had accepted a date with Nate. She went so far as to tell me that the only reason boys like him took girl's to prom was get sex. I told my mom I knew that, but all the boys took the girls to prom to get sex, so why was Nate any different. And my mom told me she knew that, but it was about picking a high value boy not settling for the runt of the litter.

    I got my gown. Not at JC Penney's either. I wanted something another girl wouldn't be wearing so I went to this seamstress and had her make me a gown. I found the shoes at Macy's and I had enough left over for my hair and nails. If anything I was raised to be frugal and pay attention to money. Nate reluctantly agreed to wear a tux. I went with him to rent it, so that I could make sure it was the right kind of tux and that he looked good in it, for the pictures. The week before prom, I took Nate to get his hair cut. I didn't want anything to ruin that night for me.

    The night before Prom I went to Nate's house. His room was a mess and his bathroom worse. This boy was going to need a lot of work. But my mission was to make sure Nate was going to be up the task on prom night. I sucked his dick, made sure he could get hard, I showed him what he was going to get on prom night, a little tits and ass. I even pointed out to him where he had to stick it. This was about the perfect prom night, don't fuck it up. I was going to lose my virginity. I left him some condoms I bought at the Walgreens. I'm sure I wasn't the only girl buying condoms the week before prom.

    I made my big mistake then. I even thought why was was I doing that? But I did it out of instinct. I had him get me fresh sheets from the and I made his bed and told him not to beat off. I never made it out of the room. Nate came alive in a way I had never seen him. He didn't outright fuck me, what he did was a lot worse. It was Rape clear as day. I yelled at him to stop, he didn't have on a condom, get off of me and all that, but Nate was going to get his pussy right then, come hell or high water, and he got it when he got me over the edge of the bed and ran his dick in me from behind, bent over grabbing at the pillow.

    There wasn't any ceremony, nothing like that. He whispered in my ear that he was fed up and he wasn't going to prom. He didn't even help me stand up. I pulled my pants on and I straightened out the bed and wiped the tears away with my hand. I wasn't crying because of what he just did, I was crying because he wasn't going to take me to prom.

    Prom night came and I sat home alone in my room. It was after one when Nate showed up and got everyone up knocking on the front door. He was in his tux and he told my mother I had promised him sex if he wore the tux. There wasn't any stopping him, he took me hard by the arm, I was in my night shirt and panties and he gave me a choice, he could take me downstairs, or he could take me in my room. My mom stood by as he marched me up to my room and gave me a royal fucking. What I called a royal fucking, whatever that really means. What I remember most was his dick wet and dripping. I got fucked on prom night.

    After that night I was Nate's woman. Girls keep their mouth shut about being fucked but guys tell it to their friends. By the end of October everyone in school knew who lost their virginity and which guy did it. Everyone knew who was Nate's woman. There are duties and responsibilities and I did every one of them, a right of passage of sorts once you have a man to take care of. I took Nate's tux back to the rental shop, but only after we got dressed up for pictures. My gown would have to wait until I was in college for the freshman dance.

    When you do get married, after college, everyone says you make a great couple. Nate got his degree in applied mathematics and I got mine in elementary education. There has never been a question as to who makes the bed and who does the fucking. And not once, ever has Nate worn a condom. I suppose in my mother's words I picked him and now I have to make my bed and live with it. For Nate things changed after prom, he didn't have to beat off, he had a woman.

    I Got Rolled On Vacation In Viña Del Mar In Chile

    In my late twenties I went on vacation to Chile. I met a girl named Ramona, a college student. We went out to a bar and drank and ate. I remember going back to my hotel. We had sex. In the morning she was gone, my wallet with my credit cards, my passport, all my cash, my watch. The most expensive hooker of my life.

    Watching

    Years ago I had just split from my long time girlfriend . I was 17 years old a virgin . A buddy and his girlfriend asked to take me out to cheat me up. After a great evening in the pub we all ended up back at his place . It was now about 12.30 am . In fell asleep on his bedroom floor at the bottom of his bed. He only had a mattress on the floor. I was woken up by a foot hitting me hard on my back. Suddenly I realised the foot was hers and she was sucking his cock. I did not move ,I just laid there with her feet pushing me in a gentle rhythm of sex. The room was lit by a dim table lamp I decided to move away from the bed just a bit .
    She stopped working her mouth on his cock looked at me rolling on the floor and laughed . At this point she stood up and stated that she needs to get another drink. She was wearing a short tee shirt and nothing more . I could she it all . After she left the room my mate said to me would I like to see her get a fucking.
    Then she came back in the room and said to her boyfriend (my best mate) are we all good . He said sure are. I wached her get cock in every way that night. And at the end she said your turn . 2 weeks later they split up . I ended up with her for about a year . She was a dirty fuck .

  • Failure To Launch, This Guy Was A Dud

    Regretful morning. I took a class and met a guy. That night he stayed with me. Sex was 9retty bad, he had too much to drink and he wasn't able to finish with a bang. The morning after regret is pretty big. The only choice for me was to drop the class and not see him again.