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.

First Date

I met this woman at a coffee shop and we started talking. We found out we were both single and she actually asked me out. The next we went out to dinner and back to her place. She mentioned she likes to know what a man likes before she has any sexual relations with him. She told me the best way to find out was to watch him masturbate and tells me to do it for her. I dropped my pants and started stroking but told me to fully undress and show my body off first. I stood in front of her showing myself off. She then told me to start masturbating again. This was actually the first time anyone had watched me do this. I was a little embarrassed at first but as I continued that feeling went away. I finished blowing my load on her coffee table like she had instructed me to do. I cleaned up and she told me to stay undressed.

A half hour had passed and she said she wanted to see if I could do it again. It took longer for me to do it but I did cum again. At this point she told me it was getting late and we ended our night.

I received a call from her the next day asking for $500. I asked why and was told to keep things private. I told her I didn't know what she meant and I don't hand out money like that. She said fine and I would find out why soon enough and we ended our call. She texted me a link and said others would get it too if I didn't give her what she asked for. I wasn't going to give in and said she was getting nothing and we were through.

I went to the coffee shop to possibly see she her again and talk to her but she wasn't there. One of the barista's mentioned my girlfriend was in earlier and said I was too much of a pervert to date. She then tells me the video she showed her shows it. She mentioned the other baristas think so too. I tried to explain she was blackmailing me for money. A guy in the line was overhearing our conversation and just asked what this woman looked like. I started to describer her and then he added some things to the description mentioning we might have both been taken advantage of by the same woman. We compared our descriptions and it was the same woman. He said he went to the police and logged a complaint but they said they couldn't do much. He asked much money she got off of me and I told him I refused to pay. He said he lost a $1000 to her and even though he paid she still posted his pictures.

We had a coffee together and discussed things further. He said she send links to the video to his company and family so quite a few people have seen it now. He said his company and family understand but it doesn't change the fact that they have seen him doing what he was doing. When I asked how bad and embarrassing his video was he pulled out his phone and showed me. His was a lot more graphic and more out there than I would ever do. He asked me to show him mine. He said he was part of a support group and they told him the best way to get over it is to start accepting it happened. I showed him the video and he said I should join his support group. I declined at first and then went.

I went to this support group and there were 8 of us. They each spoke and I spoke last. They had me explain everything that happened and then had me show the video. It was weird to say the least but once they finished watching the video they wanted me to reenact what I was doing. There were 4 of us guys in the group and they said they would do it with me. I thought this was a joke a but the 3 other guys began undressing. I was in shock and they came over and began undressing me. They started stroking themselves and when they saw I wasn't they came over and began stroking me. At the end of this they had made me cum and they didn't themselves. They got dressed while i was still in shock. They began to say that this was my first step to accepting what that woman had done to me. I put on my clothes and left and never came back.

I felt I was violated a second time but this time may have been worse. This time I was undressed by 3 other men and then they literally took matters in thier hands.

  • I Can't Believe It,

    I went to a party for a coworker, met a guy and woke up in bed with him. I'm pregnant.

    AFTERWARDS

    My buddy and I met two sisters at a club in town. It was going well until their bf's turned up and threatend to give us a good hiding so graciously we retreated. We went back to his place liking our wounds. I was lying in bed and heard something so got up and followed the sounds. upon opening the door I was confronted by my buddy having a wank, the suprise tipped him over the edge and I stood there watching as he shot his sperm over his thigh. He looked up at me with that I've been caught look on his face. I told him not to worry, we all do it. 'But do we all lick it up? because I'd like you to'. It was my turn to be shocked. 'Come here', he said assertively. I found myself kneeling on the floor by his bed inches from his liquid. I took a long look at his limp cock and his coated thigh. I could smell him, his scent, and then I lapped up the first of his spent seed. The taste intoxicating, so much I went for seconds, then thirds, then the rest until there was no trace left. My brain was fuddled I had to suck and clean that cock which I did until he became erect again. My head against the bed he proceeded to face fuck me then I was bent over the bed and I allowed myself to used and climax inside me. I was taken to his bed and used many times like a cheap whore that night and again next morning. We haven't spoken of it since but I have the feeling he'll want to use me as a bottom again

  • My Best Friend Dared Me To Post Something On This Site

    Yep, I had to get married. An unexpected pregnancy. I was seventeen, a senior in high school. An A student, Miss Manners. Who fucked me? It went through school like wild fire.

    I got married in a small private ceremony in my parents' home, out by the pool. My husband went back to college after our wedding night at the Holiday Inn.

    Our little one, a bouncing baby boy, took everyone in my house by storm. Mom, Dad, Grandma, Elise, even my cousin Kate. I went to school until the blessed event. After that I finished on line.

    Daddy did not change diapers, or bathe the baby. Since I nursed he didn't have to prepare bottles, or wash bottles, or feed the baby. Just sit back and be the proud Papa. Look what I did! He bragged to his friends.

    I'm going to college next year, this year is my gap year, taking care of the baby.

    Thanks and good night,

    It's Complicated

    As the title says it's complicated.

    I interviewed for a job in customer support, I didn't have any relevant experience. I wanted to get into tech and out of food service. I do have a college degree, but as my father says, much ado about nothing. I got along well with the human resources girl and she recommended me for the position. Totally entry level, I was assigned to an older girl to train me. I was sure the hr girl was gay and so was the girl training me.

    I spent my free time with my family, I still lived at home with my parents. My dating life was non existent, I had a couple of same sex relationships at college. One day the hr girl, I lunched with her two or three times a week, we got Subway and went to eat at the court outside the building. She tapped my hand and asked 'do you love me?' It caught me off guard, and she continued 'I can tell, well I'm in love with you too'.

    We traded a small kiss before going back to work. My training girl asked me if B had talked to me. She went on to tell me 'she's married to her old boss and he isn't going to let her go', she had been there. It turned out to be true, but he let her explore her lesbian tendencies. My first reaction was to hate him, that he did 'that' to her.

    I rebounded into the arms of my training girl, who ripped right through me. A silent killer girl, she liked it kinki. B, the hr girl told me, she will make you do things you are not comfortable with. I rebounded back to her, and her husband's permissions. I showed my anxiety at hone and my parents picked up on it.

    24 and I was into something I couldn't deal with. My parents told me to quit and look for another job. I'm back in food service, still putting my experience in perspective. I'm dating or something like it, a girl who works with me, she lives with her parents and is part time student. Talking about little sisters and home chores and adulting. We're kissing. Maybe more later.

  • Membership

    California is kind of a Mecca for gay males. I moved there specifically for the sexual freedom in the gay community. I joined a gym that was promoted as being "gay friendly". It was a private membership thing. Nudity there was common and although there were a few signs up that stated "sexual conduct will not be tolerated", there was pretty much a nod, nod, wink, wink attitude. Sex openly happened in the showers, locker room and sauna areas. As long as it wasn't out on the main floor management looked the other way.
    I had several enjoyable hook ups . But two weeks ago something happened that has several of the men at the gym treating me differently.
    I was in the sauna and open to some fun. Me and a couple of guys were nude, talking and some touching. A new guy walked in I had never seen before. He was black and huge. Like 6-4, 300 pounds. To compare I am very small, 5-6 and 130 pounds. I guess he just sensed something because he walked straight over to me and dropped his towel. His cock was big, proportional to his body size. I would say 9 inches. Honestly I expected bigger. I was eager, grabbed his cock and guided it into my mouth. I was enjoying servicing him when things took a wrong turn. He grabbed me and pushed me face down on the bench. He held me there and shot some spit on my asshole. Then he started shoving his cock in me. It was definitely not enough lube and it hurt like hell. I was screaming for him to stop. I mean I would have gladly fucked him under the proper circumstances. Like plenty of lube and taking the time to work him inside me. But he held me down and shoved inside me hard with only a little spit. I was in agony. I guess the other guys were afraid to say anything to him because they just sat there and watched. With all the noise even a few more guys came in to watch. I laid there with tears running down my face. He reamed my ass for about 10 minutes and finally emptied his balls inside me. He just stood up, picked up his towel and walked out. I laid there for a minute until I could get up and walk out.
    Now to how things have changed. I waited about a week to go back. As I stood in front of my locker 2 of the men who watched what happened to me walked in. They came straight over to me and one of them grabbed me and kissed me on the lips. I tried to pull away. Both of them then grabbed me and bent me over a bench. They pulled my shorts down and poured lube in my ass crack. One of them got in front and shoved his cock in my mouth and the other fucked my ass. When they finished with me another man stepped up and ordered me to bend over. He fucked me roughly.
    I have become known as the little sissy boy who will let anybody do anything to me. Basically I have been r**ed twice in 2 weeks.

    My Obsession

    I have a sexual fetish (or obsession) that keeps ruining my relationships. I love anal sex. With women of course. To the point I can rarely achieve orgasm from vaginal sex. I just haven't been able to find a girl into anal sex as much as I am. I get super sexually frustrated when I can't fuck my partner in the ass frequently. Vaginal sex and blowjobs just don't satisfy me.
    Now to how this sexual fetich came to exist. When I was 16 years old my family moved and I had to switch schools. I made a few friends quickly, but a guy named Billy became my new best friend. Shortly after we started hanging out constantly he let me in on a secret. Billy had a little sister. She was only 11. She was cute, skinny with really long brown hair. Anyway, one day Billy's parents were not home. He led me down the hall to his sisters room. The door was open and Billy walked in and told her to "get ready". I was stunned when she stood up and began taking her clothes off. Not to mention Billy took his clothes off too. Billy got in a drawer, pulled out a jar of Vaseline. His sister got on her hands and knees as Billy began sticking his fingers in her ass. The he rubbed some Vaseline on his hard cock and shoved it in her ass. I watched as he fucked her. When he finished he told me to take a turn. Billy didn't know one fact. I was a virgin. From watching I was rock hard so I stripped and got behind her. Billy stopped me for a brief moment and gave me instruction to "only fuck her in the ass". As I began pushing in her ass Billy said " we can't get her pregnant, we would get busted". I fucked her ass and it was amazing! I instantly loved it. Billy let me fuck her ass any time I wanted. And i wanted it a lot! This went on for 3 years. When she turned 14 she began dating and wanted to stop sex with us in order to have boyfriends.
    Now its my problem. I got addicted to her tight little ass. I have not been able to find anyone like her.

    Did She Loose Her Virginity

    So, I'm dating this girl who claims to be a virgin, but I'm not so sure this counts. She dated her high school bf for 4 years and said they never had sex. She said for the longest time that she used to just ride him but never ever went in.

    I didn't understand what she meant so one day when things were hot and heavy she showed me. Neither of us was wearing pants, and I laid back on the bed. She took my dick and laid it flat on my stomach and then sat on it. She was dripping wet and proceeded to slide her pussy up and down on my dick with my dick in between the lips of her pussy.

    She actually orgamsed doing this and so did I. My cum was all over my chest and she got some tissues and actually cleaned it up for me afterwards.

    I thought this was fine and considered her a virgin after understanding what she had been doing all those years with her bf. However, she did mention that it kinda slid in a few times, but it was just the tip and it really hurt. That nothing ever really fully went in.

    Anyways, what do you guys think? Does this count as loosing her virginity? It's a big deal to her, but honestly I could care less if she was or wasn't a virgin.

    I've Been His Lover For Ten Years And He Wants To Get Married

    I got into an office romance when I was 27, I'm 37 now and this romance doesn't end. I was very, and I mean very, inexperienced and he was very, and I mean very, experienced. The playing field was anything but even. He had all the tools and I had zero tools for my own defense. As a girl in high school I took the covenant with my church to remain virgin until married. No one before him had ever seen me naked after I was old enough to dress myself, man or woman. I did not go to the woman doctor, I didn't need to. I was healthy and in good shape and ate well and exercised. My social life was complete, I volunteered with my church and had several good friends, all women. His penis was the first penis I saw live and when he got an erection I fainted (well almost) thinking he was going to stick that in me.

    He gave me the round the world treatment the first time, in and out each hole in my body, asking me which one I liked better. I did not like anal and I told him, plus I felt that was worse than just dirty, but he took me anyways just to show me. I don't like oral sex that much, not at all really. I'm more comfortable, if you can call it that, on my back and he does everything. I don't like him looking at me naked and I don't like showering with him and having to wash his penis and having him wash up my butt crack. To him nothing is sacred, it's all for him anyway.

    But he doesn't care. He sits in the easy chair he bought for my living room, which doesn't go with anything, and I have to undress garment by garment until I'm totally naked and I have to stand there while he 'gazes' on me, from the tip of my nose to the my knees. Spending more than a little time on my breasts and between my legs. I don't understand why he likes to see my butt naked, and why he insists that I wear a shirt without anything else, so he can see my butt cheeks when I walk and my nipples rubbing up against the fabric. It must be a guy thing, because it does nothing for me. I've had to adopt the position, laying across the dining table with my legs open and letting him have his oyster, what a name to call it. I don't think it looks like an oyster at all.

    I run errands for him, not so much because I have to, I run his errands because I want to. I don't know why it gives me a good feeling to pick up his shirts and go to the CVS for him. I like to cook, I always did and I cook fresh meals for him daily. Which means that going out to eat is a once in a great while thing, he wants me to cook his dinner for him. I've learned to 'wear' things that make my boobs stand out, and panties that are way too small so he can see my vulva when its all wet and swollen. Again, ask me, I don't have any idea why that's supposed to be sexy.

    I have been with him to look at rings and I have been with him to talk to the church. But I can't 'pull the trigger', I'm scared to get married. I can't imagine myself in a wedding gown and no panties, because I'm sure that's going to be one of the things he is going to ask for. His honeymoon vision is for me to lay over the balcony railing while he pushes my wedding gown over my behind and 'enjoys' himself with me. It's not funny really, and now that Hawaii is not the place to go for a honeymoon, I don't know what to do about getting married.

    There is one more thing, he is 47 and he wants to get married so that I go ahead and have children, plural. To me getting married is the same as getting pregnant. I'm scared, I'm already 37, I should have just gotten pregnant when I was 27.

  • Not 50 Shades

    Met a guy recently and things got to the point of us having sex. Quickly found out he was into bondage and kinky sex. But I was up for the challenge. Problem is, once her got me tied up and in a vulnerable position we did a few things I probably won't do again. A lot of it was fun and the sex was good.
    After he had his orgasm I was still tied down on the floor. He straddled my face and looked down at me. He lowered himself and had me lick his ass. Suddenly he stood up and as I looked up at him he aimed his cock and my face and PISSED on me. I tried to say stop but I got piss in my mouth. I couldn't get away I had to close my eyes and mouth until he finished. I felt so nasty!