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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 Male / 23

Gym Milf

I got what I wanted kind of, I’m 23 good looking guy hit the gym a lot so I’m really good shape. I have had plenty of luck with women specially at the gym. If I work out during the day it’s usually good looking milfs that I’m hitting on. If I work out in the evening it’s usually girls my age. So there was this tight little blond that I would talk to and pretty much hit on every time I would see her at the gym. We will call her Nanette. She was married with 2 kids her husband owns a business so he works non stop and she is a stay at home mommy. I hit on her all the time. She always said no but yet still ran next to me or would be around the same equipment I was at or close to. Always talking. One day as usual I hit on her and she says ok let’s go get lunch after our workout. Caught me off guard. Nanette is 34 short great body tight ass perfect on my eyes. We have lunch exchanged numbers and that was it.

This went on for a few weeks she was having a party and I got invited to her house. I went and brought a date she calls me out for bringing a date. She was a little jealous. I go home the next time we work out. We go out after our workout this time she rides with me in my truck. She gets in and I lean in and kiss her. I pulled around the building there was more parking and a field that was empty. Really quiet and we fuck. This goes on for a about half a year. We would work out then after we would fuck in my truck. I’d send her on her way. One day she comes to work out in the evening and I’m talking to another girl that I had been dating as well. She walks up and says we need to talk. I thought she was going to get pissed for talking to this hot chic who I also had been fucking. She tells me that she is pregnant. I asked her if her husband excited. She says no because he had been fixed after their last kid.

She was kicked out of their house and was told to go stay with the gym rat. I ask her if she is sure it’s mine. She made a scene at the gym yelling, "yeah you’re the only guy besides my husband who has been fucking me." That ruined it with the chic I was talking to. Now I’m living with a chic who’s going through a divorce and I’m fathering her baby. Sex is good but not sure how it will be after the kid comes up. She does suck my cock pretty much non stop. I think it’s to keep me around and happy ?

5
# 66622 - by Nick / July 18, 2023
    • - Dating Disasters -
    Bi-Sexual Female / 26

    The Slippery Slope Got Me And Now I'm Nursing His Baby

    I tried to explain to my mother how I got into this situation. I did not initiate it and I thought I had it under control. But things start long before you notice it, and that's how it started with me.

    I was twenty four, and I hung around with four other girls. We went dancing a lot, wearing pretty dresses and panties, and liked to swing and go round, our dress blowing up underneath us and giving all the other girls there a flash. Lots of girls flashed and one of the ways that you picked up a girl was to dance close to her and flash your panties and your ass. If she wanted to be with your she would grab an ass cheek and you would go off and dance and maybe find a quiet corner to kiss and make out. It was all innocent. Waking up with a girl happened but not once ever did I wake up with some butch woman.

    At work I was a 'people person' and I got called on to help with birthday parties and summer picnics. One day, nothing about it other than we walked across the street to get a salad, our boss tagged along. First having a man as old as our father and he wanted to herd us like sheep, and second that he forced me to hold his hand to cross the street. I want my girls safe, he told me. I held his hand when we returned to the office. What I thought no one noticed, was noticed by everyone. You are his favorite they told me, and when he put his cheek forward and told me that he wanted a kiss from his girl I knew I was in trouble.

    Holding his hand anytime we were on the street, kissing his cheek every morning and going to his office to kiss him goodbye before leaving the office. Holding my face to kiss my lips, grabbing my 'tit' in his hand and telling me he wanted me. None of it happened in one day, it was just a slippery slope and I couldn't hold myself back. My girlfriend, she is my true girlfriend. Many many times I have woken up with her, especially during college and now that we were out in the workforce. She told me I was in over my head. My friend at work called it comfort sex and she asked me if my babysitter knew about her. My babysitter, my boss. She got serious and told me I had better step forward and let my Daddy know that I had a girlfriend, one that kisses the very same thing he wanted from me.

    I meant to tell him but I couldn't. It felt like I was telling him I was cheating. That same day I was wearing pink panties and I crossed my leg under me without even thinking. He could see strait up to my crotch and my panties. He got up and came over to me and leaned down and grabbed my 'tit', his new favorite thing to do with me, and asked if I wanted "Daddy to fuck me". I had to say something and all I could do is agree with him that I wanted him to fuck me. I had to call him Daddy after that, in private and when I was having sex with him. And one time I just called out "do you love your baby?"

    I confessed to my girlfriend and she told me that I should suck his dick and maintain eye contact, and let him know unconditionally that I was his baby and he was my Daddy. Sleep with him, and get pregnant, she told me.

    It wasn't that I stopped taking birth control behind his back, I told him. He told me I was playing with fire, but if that's what I wanted he would gladly fuck me day in and day out and get my pretty ass pregnant. And that's what happened, the whole affair went into overdrive and he fucked me until I did get pregnant. And that's why I was talking to my mother.

    How did it happen, the long story I've just told you, the short story is that when a girl falls in love with her Daddy she gets taken over by a need to get pregnant. I know some don't want to believe me, but I had to get pregnant, it wasn't an option. I got rid of my birth control and had sex twenty four seven. I had to have a baby on my tit.

    0
    # 66507 - by K / July 13, 2023
    - Dating Disasters -
    Straight Male / 34

    Shortest Date In History

    When I was in HS I was inbetween episodes with my 6’ long legged long time gf. So I thought I’d play around. There was a girl I had known for awhile as friends. She was popular and leader of a large girls club at school. I played football and wasnt really into the social scene but knew lots of people and asked her out.

    Day came, I was excited. Went to her house to pick her up. Made small talk with her mom for a few minutes. We leave to go out and eat, get in the car and start to back out of the driveway. I look over and she has this incredible scowl on her face. Like I jammed her face full of lemons. We start to pull away and then I realize…

    I didnt open the car door for her.

    We drive in silence. I circle the block. Pull back in the driveway. She gets out in silence. I drive away in silence.

    Yes I should have done it. Plenty of other dates when I didnt do it with other girls and it was no big deal to them. First I was upset. Then I drove off thinking, if that pisses her off this much, what would she be like day to day?

    She ended up marrying a friend of mine. After being married for many years, they got divorced. He remarried like within 4 months. Shes still alone. For me, no regrets. Better him than me. He must have opened her car door, lol.

    0
    # 66496 - by BigRich / July 12, 2023
    • - Dating Disasters -
    Straight Female / 24

    I Don't Want To Be An Adult Yet

    My rant. If I were a lesbian I would be more happy. But I wasn't blessed to be one. I didn't ask to be 'hetero' and I don't understand how I 'let' you. I'm pregnant because you can't keep your dick out of me.

    I don't like how you control me. I don't like being under you. I don't like being held down. I don't like your incessant kissing, what's that all about. I don't like you seeing me naked, worse still pregnant. I don't like seeing you naked.

    I am not your daughter, I don't like having to call you Daddy. If it's a Southern thing it needs to end. My name isn't Baby. I'm married, that doesn't mean you own me. I can't cook, no one taught me.

    I resent being reminded I can't support myself. I don't agree that I have to breast feed for a year or until I'm pregnant again. I wasn't 'born' to be a housewife. I'm too young to wear an apron. I do want a vacation, but it isn't the beach and being very pregnant. I want my own money, not an allowance.

    I am this generation. I don't cook and clean, and do laundry.

    I'm frustrated that I can't make enough to support myself. But I didn't marry you for your money. I married you because you got me pregnant. I lost my head, and woke up beside you. That's not called chasing you, I didn't even know your name. And yes, I was a virgin to you. I'm pretty sure you had never fucked a virgin or you would have been nicer to me. I can't help it if I love you, I don't understand it. It must be a nature thing. I'm too young to be enslaved to you. I am relieved you love me, and you married me and you want and can support me.

    2
    # 66489 - by Lesley / July 12, 2023
    - Dating Disasters -
    Straight Male / 53

    Christmas Tree Cover

    Back in the late 90's I was having an affair with a friends wife. She was an amazing lay. We always met at hotels, car, friends house. She was always scared to come to my house fearing we would get caught. Then one day out of the blue she invited me to her house and said her husband (my friend) was definitely out of town. They had a small child and I figured she made sitting arrangements.
    We didn't make it past the living room couch. I was naked sitting on the couch. She was wearing only a t-shirt and naked from the waist down. As I laid back and enjoyed she was on her knees sucking my cock. Then suddenly a voice surprised us both. I looked up to see her 4 year old standing a few feet from us saying "mommy, what are you doing"? I jumped up and ran behind the Christmas tree and she shuffled the kid back to his room.
    She came back and didn't seem worried about it. We had a quickie and I got out of there.

    1
    # 66424 - by Anon / July 9, 2023
    • - Dating Disasters -
    Straight Male / 50

    Hot Librarian

    The worst sexual experience I ever had was so disappointing. At the time I was 27 and she was 25. And to this day she was the hottest girl I ever landed. I can only describe her as perfect. 5-4, 110#, perfect C tits and gorgeous. I mean super model pretty.
    At the time I had a field job that required a lot of paperwork. In the afternoons I would stop by a local library to do paperwork. She was the assistant librarian. I got to know her and we flirted a little. I was married and so was she so i didn't think anything would happen. One day it was closing time and she headed toward the door to lock it. As I stood up to head out she stopped me and said "it's OK you can stay". I sat back down and she came over and stood beside me. As we talked I thought its now or never. I reached out and began rubbing her thigh as my hand worked its way up between her legs. She spread her legs a little to give me better access. At that point I stood up and we began making out. I got her half naked and intended on doing her right there in the library. Suddenly she stopped things and was afraid her boss would pop in.
    She told me her husband was out of town the next day and I could come to her house. I got there at noon the next day. We went to the bedroom, started making out and slowly removing each others clothes. I was even more impressed with her naked body and shaved little pussy. She was just amazing. I went down on her and ate her to an orgasm. At that point I wanted inside her little pussy. I moved up and went for the mouth so she could get me hard. She pushed me away and said "I don't do that". I was not happy! So I went back down on her pussy and started cranking my dick like I was trying to pull it off. Finally I got up to half mast and got between her legs. I worked my dick in her and started fucking. I thought I was going to have to check her pulse. She was a completely dead fuck. It was so boring I started going soft again. I pulled out, got up, grabbed my clothes and told her I had to leave.
    I never went back to the library again. It was such a disappointment because she was SOOO HOT!

    2
    # 66419 - by Me / July 9, 2023
    - Dating Disasters -
    Straight Male / 50

    Step Brother Took My Girls Friend Virginity

    I double-dated with my older stepbrother, and my girlfriend ( Now Wife ) had the backseat. My stepbrother and his girlfriend had the front. We were at a drive-in movie, and his girlfriend asked me to take her to get popcorn and candy. She walked slowly and kept talking to me. She went to the bathroom and took a long time. When he finally returned to the car, my stepbrother was fucking my future wife. She had been a virgin. My girlfriend looked like she had been crying, but her legs were wide open, her top was pulled up, and her tits were exposed. His girlfriend told me to get in the front with her so that we could watch. My girlfriend, breathing hard, told us he had forced himself on her and was r****g her. His girlfriend was rubbing me and asking my girlfriend, "He's a good fuck isn't he?" She told my girlfriend my dick was hard watching her get fucked.. My stepbrother came in her and then had her suck him to get him hard again. He told me she's new at this but will learn. When my Stepbrother got hard, my girlfriend got all the way naked. We played with her tits as she was getting fucked again. My girlfriend orgasmed for the first time. After they finished fucking, my girlfriend asked if I needed to cum. My stepbrother's girlfriend mounted me, and it was my first time. My stepbrother and my future wife watched us fuck. After this, my girlfriend got birth control. We would swap after this.

    1
    # 66284 - by Surry1972 / July 2, 2023
    - Dating Disasters -
    Straight Male / 25

    Finally Got It Right

    My wife Ashleigh and I met several years ago when we were both teens. Problem was, I was infatuated with her older sister, Carolyn a frigging beautiful blonde who happened to be on the school's swim team. At 5' 11" and slender, she could have dated anyone in her school. They lived with their Mom on the affluent side of town and although Carolyn was a few months older than me, we started seeing each other.
    I guess I was the bad boy type to her and by graduation we ( at least I was) were getting a little serious. The issue was as inexperienced as I was, she was downright prudish. Makeout in the car or basement, maybe some dry humping, but she wasn't giving in. I had met her Mom, but the first time I met Ash, she was in their pool around 8pm. I came around back and she introduced herself and told me Carolyn wasn't going to be home from work until late, there was an issue. So, I sat in one of the pool chairs to wait. I was surprised that Ashleigh, although very pretty, was nothing like her sister. Maybe 5'4", she was definitely " curvy". A Redhead ( she said strawberry blonde) with piercing greenish gray eyes , she was swimming in a Tshirt and bathing suit bottoms, cranking some vintage heavy metal. As I lit up a cigarette ( trying to be the tough guy) she told me that it was bad for me and to put it out. Then, she started splashing water at me. I told her a few times to stop, but she was giggling and kept at it. Finally, I put my wallet and phone next to my cigarettes' and lighter and jumped in to dunk her.
    As you might expect, we struggled and splashed and tried to drown each other until we were tired. Then, as we were just floating around, we ended up kind of hugging as we bobbed up and down. I could feel her boobs floating and bouncing against me and I knew I was getting hard, so I swam to the side to get away, afraid to get out because she'd see my bulge. She swam over, and asked why I didn't get out and before I could answer she kissed me. I don't think I fought too hard, although I thought I did. So, I popped of the pool and let my legs dangle in. While I was taking my t shirt off, Ash grabbed my junk. I told her to stop and she just laughed and said that I wasn't getting anything of Carolyn. She undid my button and started stroking me and told me to lie back. Ash took me in her mouth, still stroking with her hand and I was in heaven. It only took a minute or two and I told her to stop. She asked why, and I swear, when I started nutting, she kind of jumped a little, then her eyes kind of rolled and she started swallowing each shot. When I was done, she climbed out of the pool and threw me her towel and headed to the poolhouse.
    Over the next few weeks, Ash and I hooked up a lot. I was delivering auto parts for my fathers store, and anytime I was in the area, I'd stop over. We'd fuck, or go down on each other and never told anyone. At night, I'd go out with Carolyn and get frustrated, but knew Ashleigh was willing.
    College came, and I left town, Carolyn went to University in the next state, and I'd leave my Community college and drive to see her. After a while, I found out she was getting nailed by some Frat guy and everything ended.
    Well, my Dad passed just before I was set to graduate. Ashleigh showed up at the service, and she lost some weight and looked great, we chatted and I promised to call her. We met one night for drinks, and she was wearing her favorite Pantera shirt, we went back to my place and yeah, we hooked up. I felt like I was home. All I remember was her stopping me from pushing, telling me " Deep and slow". Then she took the top and I just stared at those huge jugs as she ground on me until she was there. She whispered, " now, with me. Now!" And I came. Oh, did I cum. Ash rolled off me, had her head sort of in my armpit as we hugged, and I felt wetness. As tears rolled out, I asked if I had hurt her. Then it just exploded. She slapped my chest and started. " You asshole, I loved you. You were my first everything. I did anything you wanted, you never took me out, anywhere. You'd screw me 3 times in a day and I couldn't walk. I had to dispose of all the rubbers you left in the garbage can. I even let you do butt stuff before you left for school, but all you did was follow Carolyn like a puppy!"
    Well, I felt like shit. I didn't know what to say, I thought she knew more than me. So, I asked " What now?"
    She said, " well, now you're going to make up for it"
    To this day, we still fuck every chance we get. We got married a year ago. I run the parts store, Ash makes sure Im happy. Oh, and Carolyn? Her and Ashleigh don't really talk, but she's been sleeping her way to the top of that communications firm.

    0
    # 66133 - by Anonymous / June 24, 2023
    - Dating Disasters -
    Straight Female / 26

    Size Queen With A Problem

    When it comes to sex and penis size I have to have large to enjoy the experience. I admit it and I do not apologize for it. My first sexual experience at age 16 was with an 18 yr old boy and he was nicely endowed. As a virgin I was broken in by 9 thick inches.
    In high school and early college I dated several boys and had much more sexual experience. Simply put, I did NOT enjoy sex with small men. In between dating I have used the internet to meet endowed men who are seeking casual sex. I have invested in a collection of large toys to satisfy my appetite.
    Now my problem... I developed an attraction to a man I work with. It was mutual. We went on a couple of dates and knew my feelings were real, possibly even love for the first time in my life.
    We had sex a couple of weeks ago. My heart dropped when he undressed. He had a very small penis. I faked things to hide my disappointment. I am so depressed. I really care for him but I do not want to have sex with him. At some point he will know I am not satisfied and do not enjoy the sex.
    What should I do???

    5
    # 66111 - by Queenie / June 23, 2023
    • - Dating Disasters -
    Straight Male / 52

    The Hooker Wanted To Date

    This was back when I was 28. I was in Florida in a hotel and alone. I called an escort service they sent over a really nice looking, tall, blonde with DD cup tits that stood out firm, a great ass and blonde hair on her pussy too. She had beautiful legs and a beautiful face. She didn't mind spending extra time, we talked a while, naked though and after she got her money. Then she sucked me hard I was fucking her trimmed blonde haired pussy and she was getting really wet. She let me suck her tits and knowing hookers don't usually let johns kiss them I did and she accepted. I told her she had the prettiest ass I'd seen in years and asked if she did anal. She said she did it a couple of times with her ex husband in the shower and it hurt her, but she'd try.

    During our talk while fucking her, she mentioned she'd not mind seeing me on a personal level. This persisted while I buttfucked her. She didn't charge extra for the buttfuck, and gave me her real name and personal number. I agreed to call her for a date. The first date we had to push off a couple of hours as she met me at the restaurant after she went on a call.

    As she said, unknown if it was true or not, I got her on her first day as a prostitute and was only her second. I asked if any of the guys she was with during the two days before we met up again had done anal. NO was the answer, followed by "that's only for you". We talked, I got her history, married, divorced, fucked by 5 guys before her husband and he let 3 others fuck her during their marriage. They had two kids, a son and daughter, 10 and 11. She was 34. After I dropped her off at her house, she offered for me to come in and I didn't go. Two days later, it was a repeat only I was genuinely interested in what the johns did to her and she to them, I got a full explanation. The end of the night I kissed her and rubbed her butt while doing it in front of her house, and closed the door behind her.

    The next morning she called and asked if I didn't want to have sex with her because she was an escort. She said that she didn't expect to be paid as we were dating. I told her I assumed that was the case, and like most dates after we got to know each other and like each other we could have sex. She said she liked me and asked me the same. I did like her, so it was established that I'd have sex with her after our date that night.

    We had sex, over and over again, I especially liked her telling me about her outcalls when she was naked in bed with me. She was a great sex partner, loved all the things I did, swallowed, offered her pussy anywhere I wanted, her ass was totally mine. Then the weird things started happening. At least weird to me. When her kids were around she didn't close the bedroom door, didn't close bathroom doors, she and even they at times would walk through the house naked at times. One time the kids were watching a show on TV, she and I were lying on the couch naked, I got aroused and wanted to go to the bedroom to fuck, and she pulled me on top of her there. She wanted me to fuck her in front of the kids. She explained that she and her ex did it all the time. With them glued to the screen I fucked her. Then a few days later I was buttfucking her on the living room floor, and her daughter stood next to us and watched, asking her mom if that hurt her, asking if I was in her "booty, or her cooch"

    That was the last straw. I couldn't take it. I really felt that no kids should see their mother sucking, fucking and buttfucking out in the open. I left and came back to my home base and found a sane girl who didn't have kids, wasn't divorced, and wasn't a prostitute. Married now with kids, she and I have a great sex life, in the privacy of our bedroom when the kids are around.

    4
    # 66085 - by Nick / June 22, 2023
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