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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.

- Dating Disasters -
Straight Female / 18

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,

4
# 68396 - by Samantha / October 31, 2023
    • - Dating Disasters -
    Lesbian Female / 24

    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.

    0
    # 68319 - by Lesbi / October 27, 2023
    - Dating Disasters -
    Gay Male / 22

    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.

    1
    # 68287 - by Sissy / October 25, 2023
    • - Dating Disasters -
    Straight Male / 31

    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.

    2
    # 68095 - by Me / October 13, 2023
    - Dating Disasters -
    Bi-Sexual Male / 22

    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.

    2
    # 67896 - by WhySoSerious / October 1, 2023
    • - Dating Disasters -
    Straight Female / 37

    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.

    2
    # 67805 - by Nicki / September 25, 2023
    - Dating Disasters -
    Straight Female / 24

    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!

    4
    # 67707 - by Girl / September 19, 2023
    - Dating Disasters -
    Straight Female / 25

    He Tore Me Up

    I am in the adult sex industry. A couple of weeks ago I found myself on the bottom end of an extremely big cock. When we met, he kept telling me that he was huge. I wasn’t afraid. I have had every size cock in every one of my holes.

    We get to the room and he is a big guy. Again, nothing I cannot handle. As I kneel down and pull his cock out of his shorts the thought crossed my mind: holy shit, this guy is huge. Huge was not even remotely the right word. He was 13” of thick, long cock. The head was almost bigger than my fist. I started stroking it with one hand and then two. He asked me if I was okay…I guess I was?

    I tried to suck it but the head barely fit in my mouth. I knew it would not fit in my ass, so I spit all over it, lubed up my pussy and told him to fuck me. When the head slapped my clit, I nearly panicked. Slowly, inch by inch, he buried his huge cock inside of me. He grabbed my hair, keeping perfect control over me and found his way in….so fucking deep is all I could think and say. I wanted to see if I could handle more, but he was already taking more of me.

    I lasted 10 minutes and he left me gaped and stretched. He eventually had me suck his head and worship his cock until he jerked off on my face and in my mouth.

    As he went semi soft, I could only imagine doing that again?

    4
    # 67611 - by Safire / September 13, 2023
    - Dating Disasters -
    Straight Male / 33

    She Messed Me Up

    My ex was sweet and loving but also manipulative and vindictive. We dated right after high school and I lost my virginity to her. She was not a virgin though. I was young and dumb and believed that putting up with someone's bullshit proved how much you love them so when she cheated on me, I forgave her... again and again. When I threatened to leave her, she'd turn on the manipulation skills and convince me to stay and of course, I gave in.

    When she told me she wanted to do porn, it broke my heart. We fought and fought over it but she got her way and moved to FL. From what I know, she had a few interviews but never managed to film anything that got published for whatever reason but I DO know when slept around quite a bit while in FL.

    We have since broken up but it left me with all sorts of trust and intimacy issues. It's really difficult for me to even get hard unless my wife tells me about her past sexual experiences or tells me stories about cheating on me (even though she doesn't) part of me thinks it would be really sexy to watch my wife fuck someone else but then my trust issues and jealousy kick in and it makes me angry and sad.

    My ex really fucked me up but I'm the idiot who let it happen.

    1
    # 67530 - by Isidro / September 8, 2023
    • - Dating Disasters -
    Straight Male / 25

    Walk Of Shame

    So I have been buddies with this dud Manny for a while. Not close friends but we knew each other in school and hung out with other friends together. After high school I went away to school had lots of fun came back home and worked for my dad at his and his friends Company as an electrical engineer.
    While back i purchased a home and my buddies would hit the bar restaurant for happy hour. We met all kinds of girls and women there young and some older women. I struck up a conversation with an older dirty blond long hair nice tits hard body with hips and an ass for days.
    I thought she was in her mid 30s she was tanned and had a slight accent. Her name was Judith went as Judy for short. We are talking it’s getting late and she says that she is going to head out and asked if I could walk her to her car. The bar was packed so nobody noticed I left. We get to her car and she says it was getting loud and had to get out of there. She also says that she wasn’t ready to call it a night so I invited her back to my place. To make it short we got back to my place and we fucked almost in every room. It was a sex marathon she even lost her panties and had to leave while going commando.
    So we hook up a few times every time she comes over and it’s a total fuck fest.

    So one Friday I have her over after work and I’m balls deep and I get a text from my buddies. They say he we are bar hopping and will come by and pick you up around 9 tonight. I had my phone and took a video of Judy on all 4s while my dick slides in and out of her butt. I also saw that it’s 7 plenty of time to full and have her on her way. I finally finished and blew my load on her face. She starts to clean up and I hop in the shower. She comes in and gets in with me. Now I wanted to get shower and get ready to go out and she knew this but she walk up gets in the shower and she has a little bit of cum in her
    hair standing there she looked amazing. I get hard and start to pound her in the shower. So now I’m pumping away and she bent over on the shower I grab on to her hips and am puny away. I blow my load and cover the insides of her Vag with my cum. My buddy knows they can come in through the garage that evening I was the last to get picked up because I had a date. So they let themselves out n which I did not care Just heard the noisy guys downstairs and was going to quickly slip out. She comes over as I’m gettin dressed gives me a kiss and grabs my cock. Says can I come over tomorrow mid morning so I can relieve some stress. I say of course. Now when she came over she wore a little yellow sun dress that shows the bottom of her ass cheeks. She had a matching yellow g string and bra. The dress was meant for me to see her goods. It was not meant to be used in public. I was starting to get hard while she was talking to me. I give her a kiss and smack her ass tell her to come over whenever tomorrow morning. She heads out and I hear silence then I hear voices and figured my buddies were giving her a hard time. It got louder and i hear yelling. I’m ready to go and head downstairs and see that Manny is one of the guys going out with us and he and Judy are yelling at each other.
    Judy was walking out as I was coming down. Manny left right behind her. I asked my other buddies WTF is is going on. They tell me that milf you have been nailing is Manny’s mom. I told them I had no idea it was his mom. They said no one did. None of them had ever met his mom. She came down the stairs and we all looked at her and she was wearing her little slutty dress when Manny hopped up and said mom WTF. We went out I didn’t text anyone had a few beers and went home. It ruined the night for sure. I figured I’d never see either of them again. I was up having coffee when Judy text me and asked if o didn’t want her to come over. I said come over she text back that she was in my driveway. I let her in and she was in yoga pants and a tank top. She said that she didn’t mean to break up a friendship I stopped her and said that nobody knew. She said that Manny was upset and it bothered her him being her son.
    That was 6 months ago Manny doesn’t hangout with us anymore he and his mom made up and she told him she would stop seeing me.

    What he doesn’t know is that she still comes over and I still use her as a fuck doll. What I did not know is that his dad owns the restaurant we met at. His parents are divorced but she still owns half the business. The age difference doesn’t matter to me. She is great in bed and very adventurous. She blew me on the freeway as we headed to pick up her car from the dealership once. We sat parked in the lot while she finished sucking me off. She pretty much lives with me and my dick is in one of her holes 50 percent of the time we are alone. She helped me write this and i rambled on but it’s because she has been blowing me while writing this. Damn Judy

    2
    # 67520 - by My bad / September 8, 2023
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