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.

Gag Reflex

Had a dream date last week that didn't quite go so well. Guy in my office a little older than me (I am 23). He is so hot, built and rumor was he is well equipped downstairs. Well the rumor was right. We got back to his place and things got hot. He was the biggest I had ever seen. Problem was he was quite the dominant type. I was on my knees sucking his cock. He had 2 hands full of my hair and shoved his cock down my throat. I just didn't gag or cough. I threw up all over his cock. It was on him, me and the carpet. It was disgusting. We cleaned up and I went home embarrassed. Needless to say, no second date.

  • His Wife His Fault

    My buddy who I have known for a while was always talking as of him and his wife’s Ricky Rochelle is her real name but she goes as Ricky. She is stacked short big fake tits large ass curvy hips. I always thought she would make an amazing stripper or porn star and had told him that before while drinking. I stay in shape and he always had this thing that he wanted to swing. I’m single but date and had asked if I knew any women that we could swap. I told him yeah a few. I also asked him are you sure you want to do this. He said yes and she was up for it. I knew this slutty hairdresser named Brittany who would do anything. I am single so it’s not like I’m married or anything like that.
    I would never make moves on my buddy’s wife either but she wanted and he wanted to do this.
    I tell Britney on the way there what’s up and she says it sounds like fun. Of course she does figured she would.

    We arrive and Britney introduces herself my buddy is excited walk over and he says are you sure she is ok she is hot. I told her yes. I tell him I don’t want to fuck in front of you. We have some drinks Ricki is in this short skirt and blouse barley containing her massive tits.
    We go to the living room and they head to the bedroom. We start making out then she says let’s go to the extra bedroom. So we do we walk in I tell her leave the skirt on and loose the blouse. Tits are out I’m sucking away I’m licking her ass and pussy she starts to tense up and after some licking and fingering she squirts a little. We spent the next few hours fucking. We fell asleep and I woke up to her giving me morning head. Britney came and while she was giving me head and said she had to go and had called an Uber. Ricky continued to give me head while I spoke to Britney. I asked how did was last night. She said he shot his load fast twice then fell asleep and she went and slept on the couch. I told her I call her later this week. All this while Ricky is blowing me.

    She climbed on top and rode me for a while longer. My Buddy finally came in and saw Ricky riding me and he says that he is hungry and what should he do. Ricky tells him let me get off a couple more times and il make something then she stops him and says run to the drive thru and get us some breakfast burritos. I’m like this is weird.

    We hear him leave then Ricky cums. After she cums she gets on all 4s and says fuck my butt. I was like hell yeah last night it was a no so I jump at the chance. She lube it’s up and I’m start slow and bottom out she takes over from there and it feels amazing. Nice tight ass and I know I’m not going to last and she starts to really start pumping I’m gripping her hips and I take my phone and hit record and am filming. I set the phone down on the nightstand so it can record what I think will never happen again.
    I tell her I’m going to blast it in your ass as so do she was playing with her clit and my balls i shot my load and she lets out this scream. I thought the neighbors might call the cops.
    I grab my phone snap a couple of pictures and more video of her on her tummy her giant ass spread open with cum leaking from her pussy and ass.
    She said that her husband had made her promise not to let me fuck her ass. She got we got in the shower cleaned up fucked in the shower. He got back we ate and she ran to the store around noon to get ready for the week ahead. I gave her a kiss and said our good byes.

    She told me to text or call her when I left. Wanted to see what her husband was going to say. He asked me what we did and I told him. He asked me did you tap that ass. I told him she wouldn’t let me go near her ass. All he said was man to bad. I said maybe next time. He said yeah we will see.
    I called Ricky told her what she said and that was it. Later that afternoon she came over and fucked me again. This has been happening at least a few times a week. Always end up with me butt fucking her.
    She says that her husband is going to ask if we can do this again. About a month later I brought Britney back and we did it all over again. What he doesn’t know is that Ricky and I have fucked a lot between our sex sessions. Not sure what to do we know it’s wrong but he keeps wanting to swap

    NOT WHAT I EXPECTED

    I met up with the most beautiful woman I'd ever seen and wasn't long before we made our way to a local hotel. She ticked all the boxes and was sexually very open expressing her desire for good sex. Well as you can imagine I thought all my birthdays had come at once. Inside the room a double bed. She stripped me off and tied my wrists to the posts and disappeared into the bathroom. So there I was tied face down waiting for the main event. You could imagine my suprise when she emerged wearing a strapon. This real feel penis was offered to me for sucking and as I'm always up for a bit of foreplay I eagerly played along. She was verbal things like ,'So you like cock you little slut' and the like. Eventually I pulled away saying, 'I've eaten enough cock'. 'As you wish', she said playfully. Between my legs she grabbed my hip raising me up. Panic set in as I was at her mercy and I knew her desire was to fuck me. Awhhhh as she feed her dick into my virgin ass. Once inserted it wasn't so bad and soon she got a steady rhythm going and I didn't want her to hurt me so let her (not that I had much choice). At one point I was on my side being bred whilst she wanked my shaft and as I shot my seed onto the bedding I remember thinking that wasted semen was supposed to be for her pussy. I was suprised to see my cock was still hard, a point not unnoticed by this woman. She untied my wrists and still impailed I was walked to the window where she roughly fucked me whilst more than one passerby saw my plight. The evening came to an end when with an audience encouraging her on I announce I was about to cum at which point she grabbed my throat pulling me back exposing me to the strangers and just to put icing on the cake she said, 'Put a good show on for then and next time I'll see if I can arrange a real cock'. I couldn't help myself and shoot a heavy load all over the pane which she made me lick of and swallow as the voyeurs clapped and cheered. I never thought I'd enjoy something like that but I did. She's texted me a couple of times since even saying she'd found an eager cock. What should I do?

  • No Matter How You Frame It She Can't Get Me The Baby I Want

    A blast from the past upset my life in ways I never imagined. She and I were in college at the time, a regretful moment when I lost my self control and got into a competition with another two girls to see who could bring the other girl to orgasm. This was during Spring Break in South Padre. Unfortunately it was filmed by another girl who was there. I was labeled a lesbian, the film did the rounds on campus, she 'came out' in FB naming me as her forever girlfriend.

    Ten years later I remained unmarried, this reputation follows me. It's worse because 'Elaine' continues to haunt me. Unfortunately she's in my friends group and she's over affectionate. Which keeps all potential suitors at arm's length.

    A certain man who was not married commiserated with me, he has a past transgression from college, busted by the DEA. He 'served' five years and was still on probation. I asked him to get me pregnant. Something Elaine can never do. Once pregnant I married him secretly behind Elaine's back, in another state where people run away to elope.

    Elaine went ape shit on me. She can't get me pregnant, I don't care how affectionate she is. And I don't want my child to be born 'out of wedlock'. Elaine's problem is she doesn't want to grow up. Maybe a felon isn't a great fit, but he is a he, not a she, and eloping with a man is a hundred times more acceptable than eloping with Elaine. Ask anybody, I've got the baby inside of me to prove it.

    I hate picking lesbian, I hate that I'm a lesbian. It's not my fault. I wish I wasn't. No matter how angry you get, lesbians can't get pregnant together, they just can't.

    Just Need To Vent

    When me and my wife first started dating after about a month she fell on hard times and needed money asap, I told her at the time to call the people she owed and request 2 days then when I was paid I'd give her the money plus extra so she had enough for extras.
    The next day when I went to see her she was sat on the floor crying surrounded by tissues and started repeatedly saying she was sorry and begging me to forgive her.

    I asked what was up and she explained that she went to see her mum and dad to borrow the money and they said no but the landlord next door over heard and asked her in. He said if she would do a sexy dance for him then suck his dick she could have the money and because she was desperate she agreed but when she did it he offered her extra saying it would be lots more.
    She said how she did as he asked and had a massive stack of money so she trusted him. By the time they were done she'd danced, sucked and been fucked and she was treated like trash throughout the whole thing then he gave her the original money she needed. I asked her about the extra and she said he told her she was an ungrateful whore and she should learn to smile if she wanted more customers, she said that he then put £2 inside her cum filled pussy and told her to get out and get a happy meal so she could cheer up.

    I sat with her for a while trying to help her calm down and process what she'd told me and was doing good until she tried using sex as a way to say sorry. I was genuinely turned off and aroused at the same time. I wanted to spit in her face call her a prostitute and make her feel shitty but at the same time I wanted to fuck her and do whatever i wanted to her but feeling all mixed emotions I just walked out and said nothing to her for a few days.
    I went to see her after I'd cleared my head and thought it over and we moved on even getting married eventually and it's now been 20 years.

    I only decided to share on here as a way to vent as every little thing I do is met with extreme blow outs by her and even got kicked out once for daring to talk with an anonymous person online and this always gets dragged back up, but not once have I ever used this against her only once coming close by saying she's done dumb stuff in the past but was knocked back by her saying get over it it's in the past.
    Anyway if you read this thanks for sticking till the end.

  • Handicapped Date

    25 years ago I had just turned 30 as I moved to a new city with no relationships in sight. Feeling a bit down, I tried a dating phone line and very quickly got connected with a woman in her mid-20s with a sweet voice who wanted to talk to me indefinitely. The time on the line was limited unless you paid more, so we exchanged numbers and called back to talk some more. She sounded very open and wanted to meet me tonight, but then said she had a confession: she had her right eye removed because of cancer and her socket was covered with skin. This understandably made her self-conscious and unable to date easily. She asked if I was ok with this, and I said I was so she soon gave me the address of the friend she was staying at and I drove on over.

    Her older friend greeted me at the door of her apartment, she also had a male visitor who I gathered was a truck driver. She seemed very protective of her young friend, but also wanted to give her space for her own, so soon she and I went into the spare bedroom to hang out. We soon did some kissing and necking, and I got her shirt off to suck her nipples. We agreed not to have intercourse on our first date, but I asked what she thought of oral sex, and she said she was fine with giving it but "I don't like it when guys come in my mouth." I admitted that this was my favorite activity, but would respect her limits. I instead stripped her naked on the edge of the bed and kneeled in front to go down on her, which made her moan in pleasure and appreciation. After she came once I kept licking and she she didn't push me away, clearly wanting more. But soon she started asking if I could go inside her. I asked if that didn't violate our earlier agreement, but she pleaded with me saying she wanted it so much now, and finally said "I'll do whatever you want if you just put it in for a minute." I again asked if she was sure and she said she was, so I stood up and quickly slid in my hard cock, checking my watch to time it for a minute. She stared at me with her one eye and kept saying "thank you thank you thank you" over and over, "it feels so good, so good." She was clutching me any way she could but I held her to her word and pulled out 60 seconds later, giving her a couple extra thrusts and seconds for good measure. She asked what I wanted her to do, and I told her she already knew, so we switched places and she kneeled in front of me to take my cock in her mouth. Soon I was gripping her head to pull her down harder, she grimaced but stayed there while I started squirting into her mouth. She went "ugk!" but let me hold her down until I finished. She spat out onto some clothing on the floor and wiped her mouth, then after I wiped my cock clean asked her to suck some more, which she did for another five minutes or so.

    I soon went home, and wondered if I was taking advantage of her desperation for sex to do something she didn't want. I called her later and apologized, though she said it was ok. I never saw her again but always wondered what became of her, and hoped she was one day able to get a glass eye to improve her appearance and have a better social life.

    Crazy Ex Bex

    Many years ago when I was younger I used to have a girlfriend maybe 3 years older than me and when we first got together we decided it wasn't gonna be serious straight out the gate instead we'd just have fun with it and we did after our first date we were making out in a little green sitting area with trees and she was topless letting me enjoy her wonderful D cups and by the end of the week she was getting a facial behind her garden shed because there was no privacy in her house.
    Within the month she'd gone out drinking twice and twice she'd cheated but it was meant to be fun not serious so I was cool with it and after talking to her sister who was only a year older ended up fucking her.
    tina was a lot like her sister except a bit shorter with lighter hair she still had the magnificent tits and a fit ass, prettier though. She didn't like how bex treated me so I think this was her attempt to sweep in.
    Back to it though, Tina heard what happened said bex was out and asked if I could help her with something as everyone else was out so I said yeah and she took me upstairs, she left the room and came back naked and I just went for it finishing just before bex came through the front door and she was oblivious despite Tina being all Rosie cheeked and having shakey legs.
    By the second month bex was talking about having kids, getting married, getting a home and became very possessive like crazy possessive. But I was getting all the sex I wanted so decided to roll with it cautiously luckily. I took her out for lunch at Maccies the one day as I needed some recovery time and the guy said no charge for me which was awesome so I asked why, turned out she'd sucked him off before he started and he felt bad. She got crazy after seeing us talk and actually bitch slapped another woman accusing her of making eyes at me.
    This was the call I needed to say end time on what we had so we had one last fuck and afterwards she started saying how she thought the condom ripped , luckily I'd used mine not hers.
    I talked to her and suggested the split and she wasn't having it so I had to think of a new plan, 2 weeks on and I'd still failed and she was now trying to actively get pregnant so I started thinking outside the box.
    I suggested maybe we go to our hidden spot and she could do some naked sunbathing which she loved doing and we went, we fucked and then I excused myself saying I had to pee, jumped straight on texting people and said to walk by and happen to see then come up.
    The lads were good, 5 minutes and they were there and bex didn't flinch or even try to cover herself. I said I'd run to the shop for some drinks went off for 5 came back because I'd forgot my wallet and she had one in each hole a one in her hand. She didn't stop till she was done and they'd finished then tried telling me they'd forced her but I had my man behind a tree watching with camera for their safety and he showed me. I told her we were done and the chatter around town must be true and we left. She told everyone I was a one pump chump so she had to get rid of me but I didn't care.
    I had a secret relationship with Tina and it was amazing and when it did eventually end we did it as friends.
    I moved away and lost contact with her but saw her a few years back and found out bex fucked a guy for a job, got pregnant them he left town and wasn't even the manager he just knew her type and now she's living in a shit hole and their parents are raising the kid.

    I really dodged a bullet there

    Fancy Dress Mishap

    I took my husband to a costume party where we pretended to be other people so we could try wife swapping with another couple and after a while we found a couple willing to try it.
    All 4 of us kept our costumes on so I got fucked hard by star Lord with mask and he fucked spider gwen. It was only by chance as me and the other woman were getting cleaned up I noticed a tattoo on her wrist as we decided to play with each others cum filled pussys and I realised it was my sister in law.
    We left the hotel room after and I haven't said anything to my husband about knowing who they were. Now everytime they visit I can't help but think how his brother in law is a lot smaller than him and how he fucked and creampied his sister.
    Should I tell him or his sister or just keep it to myself as a dirty sexy secret?

    Deal Breaker

    I recently broke off a short term relationship. Problem is I can't tell him why.
    Back in college I had an affair with a married, older professor. It lasted nearly a year. Well the guy I have been dating for a few months invited me to attend a backyard BBQ at his families house. To my shock his dad is the college professor I had the affair with! When we came face to face with his wife standing beside him, we both nearly fainted. I can't tell the guy I fucked his dad!

  • Exploded On My Date

    First date with a girl i just met at work, things are getting frisky. I should confess at this point that I'm a fast cummer. Always finish in seconds with a new girl, but oral can help me last a couple of minutes. She unzips my pants and starts to lick and suck me. Bliss. Then...i feel it...that tickle...I can't believe it, i'm going to be premature. I try to stop her head from going up and down, hoping maybe I can hold it.. then all of a sudden...she stops. Looks up at me. She asks, "are you wearing cuh...cologne??" Her nose begins to twitch and she just starts having a sneezing fit at my dick. And then I explode all over her face. While she's sneezing. After what seems like forever she finally stops and stares at me, my load all over her face. No, we haven't gone out again.