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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 / 39

Protecting Your Teen Is Useless

I asked my parents for permission to go to a New Year's party (back when I was a junior in high school). OK, but I had to wear a pad. Just in case some jerk got his hand down my pants. At midnight I got kissed, and his hand went across my behind and then up my shirt and pinched my boob and he grabbed me hard and shoved his erection against me and asked me if I wanted to fuck.

All I could do was babble, sure I want to fuck, but where. We went outside and to his car and he told me to get in the back and take my pants off. He saw that I had a pad in my underwear and I told him it was my mother's idea. Not sure about what to do next he told me to turn over and he got on me from behind and ground his dick in until he got in my ass and I got my first ever butt fucking in the back of his car. Sure it hurt, but it felt good. I liked it.

I went home that night with a sore hole, and wet cheeks from him leaking out.

First of all when my daughters started menstruating I put them on the pill. When my daughters went out I told them to keep their legs together and their heads clear and if a boy asked them to fuck to give them the finger. Which method worked best I don't know, but the pad in your pants just gets you butt fucked.

1
# 55818 - by Ellen / January 2, 2022
    • - Dating Disasters -
    Bi-Sexual Female / 23

    In Trouble And I Have To Get Married

    During my last two years of college I got into a sexual relationship with another girl and we moved in together. I suppose sex gets old, certainly we went from sex all the time to sex once or twice a month. Much better sex, very sensual and emotional. Then one night a guy grabbed me at a party and the heat got to me and I cheated on her.

    She forgave me, barely. We went our separate ways after college but it was too much. Six months later we were living together, had the best sex ever and swore forevers. But my button gets pushed by the guy from college, he comes to town and I end up going home with a belly full of cum. I don't confess this time.

    But life kicks you in the ass. I'm pregnant. He is all for it, he accomplished his male goal. I want the baby, I'm four months now. I accomplished my female goal. The baby messes up the calculus. If I didn't cheat I wouldn't be pregnant, I cheated and got pregnant. She has given me an ultimatum, get married 'now' to her. He gives me an ultimatum, get married to him.

    It's nice to be wanted, but I'm going to marry the one I love.

    1
    # 55581 - by Reba / December 20, 2021
    - Dating Disasters -
    Straight Female / 37

    Knocked Up Like A High School Cheerleader

    I gravitated into this job, journalism degree, Hispanic, pretty face and camera friendly, and the girl on the side of an influential man. I was an on camera reporter on a midsized television market before my current high profile position. My relationship is a secret and I have had to be very careful. But now I'm pregnant. I had to get off my birth control and detox. He was sympathetic but his desire overwhelmed his judgement and he tossed my concerns aside.

    I am taking a leave of absence and going into hiding. I just cannot go the termination route and I cannot go the adoption route. I can't get married, he is married. I am not 16, I'm 37, a little late in the game to have an illegitimate child. As I let my mother know, I got knocked up.

    0
    # 55373 - by Viviana / December 10, 2021
    • - Dating Disasters -
    Straight Female / 41

    Dangerous Date

    I was on a dating site and this guy started chatting with me - it was a Saturday night and I was alone drinking a glass of red wine and looking for fun. He invited me over his place and this was a mistake but I went along anyways. His house was on a dark country road at least 1,000 feet from the main road.

    I got there and the guy was very different then his photo - his photo he had sent me was at least 10 years old. He was not as sweet looking and somehow he was trashy. I had brought a bottle of wine so we opened it.

    His place was a total mess and he looked like a meth user. He started telling me that he had recently got out of state prison and that he was horny as hell. He had two large guard dogs that he eventually tied outside by my car. I started looking around realising that I had to get out of there.

    He locked the door, shut all the lights downstairs and he grabbed me and told me that we should go upstairs - so I went along as to not rattle him. I noticed a large knife on the night dresser. The bedroom was a total utterly mess. He got totally naked except for his boxer shorts - he was actually a very fit guy - he pulled down his boxers - I noticed that he had a really nice cut cock - nicely trimmed - so I decided to calm him that I would give him a blowjob. I started sucking him for a good 5 minutes and this gave me time to think - but he got upset as he could not get hard. I was scared but trying not to show it.

    He asks me if I would do a few line of cocaine with him - he told me that he would perform better - I just smiled and said sure - he picked up his cel phone and called his pusher for some coc.

    The pusher was on his way over, now I really had to get out of there. He was naked and I was not - he started dressing up - this was my window to get away - I told him that I would go downstairs and turn the lights on for his friend (the pusher) - I leaned over and kissed him and I asked him if his friend had good stuff - he replied the best - this was to establish trust - I ran down quickly but not looking like anything was wrong - I turned on the lights - unlocked the door (which had two deadbolts for some reason) and ran towards my car.

    Thank god the dogs ran towards the house (prob as I had turned on the lights and they wanted in) and only started barking and running viciously towards me once I pressed my unlock button and the headlights of my car came on - but by that time I was too far and I jumped into my mustang.

    I started the car - put it in reverse and backed up the long country driveway - as I did not want to turn around in case he came out and try to stop me - once I got to the road I stopped and calmed down - took a second to catch my breath - I reversed into the dark country road and took off and headed home.

    I did a bit of research on the guy as I had his cel phone no. - turns out he works at a used car lot - scary to think that women go there and buy a car from this douchebag.

    5
    # 55352 - by Karen / December 9, 2021
    - Dating Disasters -
    Straight Female / 18

    He Stole My Virginity

    Hold on, before you judge, everything was consensual, I think there was just a misunderstanding. I'm not too shaken up about it anymore, just wanted to get this off my mind because I've been thinking about it lately. I'll admit that I made some mistakes too.

    I was 16 and messing around on Tinder. Boring summer, parents always worked, and friends were away on summer vacay. There was this 24 year old guy who caught my eye, we matched, and began chatting. He was real good with his words. I was hooked immediately, we even began sexting. He always thought I was 18 and living with my parents while working a part time job.

    One day he asks when would be a good time to meet me. I don't know, I just kept following my lie about a part time job and said that today was a good day. He drives up to my house with some pizza and a 6 pack. We Netflix and chill for a bit, but soon enough, we're making out. His hands got up my skirt and wow they worked magic on my clit. I came so hard that it was my first time shaking.

    I asked if I could return the favor, so he unzips his pants. His cock sprang out and it was impressive for a skinny guy! I got on my knees in front of him to suck him off. He wasn't my first cock to suck... I've already sucked off my swim coach to make varsity (maybe a story for another time). He soon pops his load in my mouth while pressing my head down with his hand to make sure I take it all. I try to get up to spit, but he keeps me down saying that I need to swallow. Even though I tapped a few times, he wouldn't let up, so I swallowed his load.

    This continued for awhile, I was just addicted to him. Some days I told him I had "work" but all I could do is sit all hot and bothered until the next day. We soon started giving each other erotic massages in my bedroom. I would lie naked so that he can massage me all over, ending with a nice fingering or oral. Then I would do him, usually finishing him off with some oral.

    One day, we were doing our usual thing when he asked if he could take it to the next level. I thought he meant the massage because he didn't add the oil yet. I said mhmm then I felt him climb on top of me. Instead of feeling the drops of oil, I feel something press up against me down there. I was a bit confused and said, "Wait what?" but he answered by plunging his cock deep into me.

    I bolt upright, grinding my teeth and groaning, but he took it as an invitation to grab my neck and whisper in my ear, "Fuck you're so tight for a White girl." He starts fucking me. I couldn't help but grip the sheets while I adjusted to him. Eventually, it began to feel nice until he quit early to cum on my ass. Then he had the audacity to say, "Wow you're so tight that you bled from a light fuck."

    I ghosted him after that. Thankfully he was normal so that he just forgot about me after awhile, didn't harass me or whatever. When the guy I had a crush on got back from vacation, I hit him up to see if he wanted to hang. I always hesitated before because all the girls say he hangs with girls only to fuck them, but I wanted my virginity to be special. We got burgers then chilled in his parent's basement late at night. He had so much pent up horniness that we ended up fucking a few times that night. He gagged me with my shirt because I was making way too much noise. But yeah, at least I got to enjoy fucking my crush after all that.

    3
    # 55349 - by Kate / December 8, 2021
    • - Dating Disasters -
    Straight Male / 26

    Mother And Daughter

    For about eight months I was fucking an older married neighbor.
    She's very attractive and extremely sexual. So when her husband, who works away a lot, wasn't home, I was fucking her.

    You name it, we were doing it. Oral, fucking, anal, ass to mouth, some fisting, toys.
    After a few months of fucking my neighbors wife, I began dating a girl my age. Someone I worked with.
    I'd always stay at her place, as it was close to work and we'd fuck a lot.
    Even so I was still screwing my married neighbor.

    On a Sunday afternoon with her husband working in Europe I was fucking my neighbor. My cock was deep up her pussy and she had me fucking her asshole with a dildo from behind.
    She'd just started to orgasm when her lounge door opened.
    We both looked to the right, to see her daughter, the girl I was dating from work, stood in the doorway.

    What's crazy, is her mom continued to orgasm on my cock as my girlfriend began to shout at us both.
    Obviously we stopped, but I was still horny as fuck and my dick was so erect.
    All I could think about was fucking them both, but unfortunately it didn't turn out like that.

    My girlfriend dumped me and moved jobs. However even though she promised her daughter she would, her mother didn't stop fucking with me.

    It was a disaster for a while, but as things calmed down and my ex girlfriend didn't tell her father, I figured when I saw my ex out in a bar with some of her girlfriends, I'd go and talk to her.
    She told me I wasn't the first guy her mother had fucked behind her dad's back. And suspected her dad knew and accepted his wife fucking other guys. She even suggested he might like the idea.

    That night I went back to her place and we had such amazing sex. It was if her inhibitions had been lifted and we got into some really dirty sexual experiences.

    We're now kind of back together, but we only see each other a couple of times a week due to work. But the sex continues to be awesome.
    She knows I haven't stopped fucking her mom, but we don't mention it.
    I'd love to fuck them both together and did recently suggest us all getting together over the festive period.
    She didn't say yes, but she didn't say no either. What she did say was "We'll see".

    0
    # 55272 - by Carl / December 5, 2021
    - Dating Disasters -
    Straight Female / 31

    We Were College Era Roommates But Are Now Closer Than Sister

    In 2015 I was 24 and at a new job. I went out with a group from the office and one of the men kissed me. It was a lot more than a kiss, he groped me and immobilized me, kissing me and grabbing my butt. He told me he wanted to fuck me and if I had a place where we could go. We went to my apartment, my roommate was already in bed and he outright fucked me, just forced my pants down and got his dick in me and fucked me.

    He passed out and after a while I fell asleep too. I woke up and my roommate was beside me, she was naked and holding onto me. I woke her up because I needed to go to the bathroom and she came with me asking me who the guy was. She told me he came to her room and fucked her and spanked her and told her to get in bed with me. We decided to get back in bed with him because we felt he would spank us if we didn't.

    My bed is too small for three people so my roommate got in my arms and I spooned her. Something came over me, holding her like that. I hugged her real tight and cupped her boobs. We talked, he was passed out, we talked about both of us having his sperm in us and what it would be like if we both ended up pregnant. Right then, we talked about doing it, getting pregnant. We would be sisters for life.

    In the morning he was hung over and we fixed coffee and he asked us to be naked for him. He looked us up and down and poked his finger in our slits looking for our clits. He spanked our behinds and sent us to bed and followed and fucked me again. Then we slept until mid afternoon.

    Nine months later we gave birth to a boy and a girl. If we weren't pregnant from our first time with him, we got pregnant from having him continue to fuck us until we missed our periods. He has child support and other obligations and we have custody. For him it was a very expensive night and having the glory of having two women to fuck. We never told him we were impregnable at the time and it came as a complete surprise to him, but tough luck.

    He hangs around, we give him enough to keep him from running off. We don't need a man but seeing as he is around we have to keep him coming back. Our kids started the first grade this fall. They have two mothers and most people see us as a lesbian couple although we consider ourselves straight with a twist. From the very beginning, after that night when he first came over, we sleep together, we still spoon and share a pillow. The tighter the spoon the better. We are both boob girls but have gotten down and dirty between the legs when he isn't around to bother us. I love holding her against my breasts and cupping her boobs, it's a thing with us. Maybe there is a little lesbo between us.

    2
    # 55216 - by BBB / December 1, 2021
    - Dating Disasters -
    Straight Female / 26

    I Am Now Lesbian Free And Straight

    I am a recovering lesbian. I've heard it all, so spare me. I was athletic in high school, played soccer and lacrosse, and had my first sexual experience with my assistant coach. She was deliberate and took me from a novice to an experienced sex partner. She had other girlfriends and broke my heart.

    I stayed in the lesbian lane for all of my high school and college life. Always with the same group of girls. I got a job with a private school and got involved with one of my students. The school was not aware but her parents were and I agreed to resign and go to therapy. During therapy I found out that it was my teen experience that lesbianized me.

    I am currently with an experienced man who is helping me learn how to be straight. It has been difficult, sex was difficult, but I have slowly learned how to participate sexually. Emotionally I'm further along and have chosen to commit myself to him. He has two other previously lesbian women who I share living quarters with. He is very experienced at breaking lesbian behavior.

    I am ready to prove myself straight. I have chosen to give up women sexually. With my certificate I will have met my promise to that young women's parents. I have done all I can apologizing and I have asked her to go through delesbianizing. You can't do this alone and you have to commit yourself to a man. He has room for one more former lesbian in his life, she is young but either she uses this chance or she will drown in lesbianism.

    2
    # 55074 - by Sandra / November 23, 2021
    - Dating Disasters -
    Straight Female / 33

    Not Fun

    After a lot of discussion and dirty talk in the bedroom, my husband and I decided to try a threesome. We spent time on forums talking to different guys to find someone to join us. Our excitement and dirty talk is probably what led us to setting it up with the guy we did. The choice was based almost completely on the size of his dick. After watching so much threesome porn we figured if we are going to do it we might as well get a porn sized dick to do it with.

    The guy was about as cocky as you could expect someone with a huge dick and that was about to fuck a married woman could be. When we got into it and his pants came off, he wasn’t lying. It was ridiculously big and incredibly intimidating. He wasted no time getting to business and after some effort to get it inside me he just started pounding. He fucked hard and just non stop. His stamina really was incredible and he was flipping me in all kinds of positions. Sounds like a porn scene and that it would be so hot.

    The reality is I felt someone was ramming a baseball bat into my pussy as hard as they could with no interest in how it felt for me. My pussy was sore from being stretched around him for so long and he kept jamming his dick against my cervix which also was not fun. After what seemed like forever he finally came and then when he pulled out he looked at me and said he loved seeing how his dick ruins pussies.

    My husband fucked me after him which I could barely feel because I was so sore from the pounding I took from the other guy. But then when my husband was done big guy fucked me again. Same thing where he just jammed it into me hard. When he left he made jokes about how loose he made me and that if I wanted to get “wrecked again” to give him a call.

    So for me, big dicks are not fun. My pussy was sore for over a week. I felt like a whore and I felt used.

    6
    # 55002 - by Plates / November 19, 2021
    • - Dating Disasters -
    Straight Male / 30

    Caught My High School Crush

    This is the definition of having your heart broken. A worst scenario type of thing. It's kinda my fault too.

    There was this girl I had huge crush on in high school. I was totally obsessed with her. We lived within a block of each other. We actually by random got hired at the same job. It was like a dream come true. I started to talk to her. Got to know her. I got her number. Eventually I told her I really liked her. She kept telling me, that I was a better person than her and that she was this broken girl that had a shitty life. It just looks perfect on Instagram etc. I felt like she was making excuses. We did hang out a lot. She was one of those girls that likes older men. So when she was 18, she'd date like 25, almost 30 year olds. I was 17 at the time.

    So this is when it happened. She had her own apartment. We used to hang out a lot there. We never had sex though. Only kissed a few times. I texted her that I wanted to come over. She didn't respond right away and I was already almost there. It was normal to just show up. So I figured she's probably busy.

    I get there. I knock. It's like a 5 minute wait. She eventually comes to the door and she's wearing pajamas still and a big t shirt. I said hey and she said, you should have called me. I said I texted you. She was standing at the door like she didn't want me to come in. I can see her hallway in the background where her room is and right across from her room is the bathroom.

    I shit you not, a naked dude, like straight up butt ass naked, walks out of her room, and he sees me and is like, oh shit and casually goes into the bathroom. Like butt naked, and he wasn't even trying to cover it up. He walked out, and I could see his dick was hard and he just strolls into the bathroom.

    I was like um....and she just looked down in disappointment because we both saw him. So we kinda stood there. And then she was like, let me text you. So I left not sure what just happened. She texted me saying, that was just a guy staying there. But then she eventually told me, they were just fucking. Not dating.

    If I was a detective, I should have saw this earlier because a few days earlier, we were sexting a bit and she sent me some photos. Well she wasn't holding the phone. I never thought to ask who took the pictures.

    I went home and cried for hours. I just kept imagining what was going on in that room. I'm sure they continued even after I left. When I was knocking on the door, I was wondering what they were doing. This dude literally did everything I wanted to do with my dream girl. It just broke me. We never spoke again.

    Anyways that's my sob story.

    4
    # 54899 - by Singleandlonely / November 15, 2021
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