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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 -
Bi-Sexual Male / 52

Crazy Women

I met a woman. we hit it off, and after a few days decided to go out. we got to the restaurant, ordered our food and drinks. about halfway through the meal, she told me she lived with her boyfriend, and just wanted a good time and a free meal. first I freaked out, wondering if he was stalking us. then I just blew it off and continued the date. we ordered more drinks and some dessert. I told her I needed to go to the restroom. I got up, and out the door I went, leaving her with the bill. I never heard from her again.

another time I went to a restaurant with a woman. we ordered our food and drinks. the server brought the drinks, and I took a sip. she says "you're not going to use a straw? people put the mouths on there!". I didn't say anything. the server brought our food, and she picked up her fork and started eating! I said "you're not going to ask for plasticware? people put those IN their mouth!". she got all bent out of shape, and stormed out. I never heard from her again either!

1
# 74642 - by Anonymous / November 13, 2024
    • - Dating Disasters -
    Straight Female / 29

    It's Not My Fault

    Not a slut, not a whore, I'm the lover of an older married man. I love him. If I could walk away I would.

    0
    # 74444 - by Riana / November 4, 2024
    - Dating Disasters -
    Straight Female / 55

    Only Blow Jobs

    Talked to a guy on chat line and we got along great. He was out of town on business and was close to me so I meant him for drinks and dinner. He was tall thining hair and kind of good looking. H 3 drinks each and a good dinner and had a great chat. Went to his hotel room with some wine and scotch with plans to party. Started to make out feeling each other's body helping each other get undressed. He was kissing me and had a finger in my pussy. I love giving blow jobs and sucked him off and swallowed. He started to cry and I will follow up.

    2
    # 74317 - by Sweetkate65 / October 28, 2024
    • - Dating Disasters -
    Straight Male / 25

    My Sponsor

    I f’up. DUI ended up getting me a suspended license, heavy fines, court costs and lawyers fees. Worst of all, small town Justice gave my Court Ordered Therapy.
    Not AA but group therapy with every type of social deviant and loser known to man. Meth heads, violent offenders, burglars you name it, all meeting in the basement of the local church with a police officer in the parking lot.
    Worst thing is that you have to pay a fee until you are released by the therapists, why release you when they are making money off you?

    That’s where I met Mousie. Not her real name but someone once decided she looked like a little brown mouse and the name stuck. She came to therapy as a teen who had shoplifting issues. After she graduated she stayed on as a volunteer and ended up as my mentor. I called her one night after a really rough day at work and I found myself needing to drink. She came over, talked me off the ledge and when I hugged her to thank her, well you know, it got physical.

    We ended up in my bed, things were going the way they are supposed to when she started talking to me, guiding me. I’m used to communicating but this was different. Mousie referred to her private parts in the third person! I’m busy licking her pussy, and she’s saying things like “ lick her up and down” and “ nibble her, bite her!” I thought that was a little weird. When I moved towards the box of rubbers in the night stand, she told me no and guided me into her. Again, she was saying things like “ pound her hard, make her do it!” When I started talking a little dirty to her, she froze up and told me to stop with that filth. When I got close, I asked if she wanted me to finish on her or what and she told me that was a sin and I should do as God planned. Then she kept saying, “ she’s gonna do it, push now! Do it! Make him do it with her. “
    I pulled out and actually slid my cock between her ass and the sheets and nutted there. Afterwards, we were laying there catch our breath and she asked me to be her boyfriend. I told her we would talk.
    I’m confused and afraid to go to group this Monday.

    0
    # 74248 - by Donnie / October 25, 2024
    - Dating Disasters -
    Straight Male / 24

    Girl Invites Me And My Friends Over To Gangbang When She Drinks.

    I know a girl who invites me and my roommates over to gangbang her EVERY time she gets drunk. One of the more recent times, she was dating a guy, but she got drunk and invited us all over while he was still in her apartment. She was so drunk she forgot he was there. Needless to say, they broke up.

    3
    # 74140 - by Just a friend / October 20, 2024
    • - Dating Disasters -
    Straight Female / 66

    Long Ago But Seems Like Just Yesterday

    When I was a senior in high school two of my friends and I along with a teacher chaperone attended a journalism conference in April at a college in Virginia.
    The last full day we had a free afternoon and three college guys invited us to go swimming at a local river near the campus.
    At first our chaperone said no but after some pleading she agreed to let us go with a strict curfew time to return.
    Once we got to the river we swam for a while then ended up on the river bank with the guys on blankets sunbathing with some casual kissing.
    After a while the guy I was with asked if I’d like to take a walk. I got up then he gathered up our blanket so I had an idea what he had in mind but went along. We walked quite a ways then found a nice place along the river and spread the blanket.
    Things started with casual kissing but soon got very passionate.
    I had on a one piece swimsuit which tied around my neck so he untied it unzipped the back dropping the top exposing my tits and began playing with them as we kissed. I had let guys do that before but only in my blouse not exposed.
    That was as far as I had ever gone but when he unzipped my suit the rest of the way I knew where things were heading so I asked if he had (as we called them back then) a rubber.
    He had come prepared so off came my swimsuit. He then removed his trunks so there we were totally naked in the outdoors.
    Getting totally naked with a guy made it exciting so I quickly got extremely horny. Being my first time having intercourse I was very nervous but soon relaxed as the sex became very intense.Then when it was obvious he was coming I had an unbelievable orgasm. When we finished I looked to make sure it was in the rubber which it was.
    Once we got dressed we returned to where the others were and went back to campus before our curfew.
    The next day we returned home and back to school.
    Two weeks later I missed my period. I had gotten pregnant at 17 two weeks before turning 18 despite using protection .
    It was a big deal back then when a girl got knocked up so I was the talk of the school since I had gotten knocked up by a college guy on a school trip and had no idea who he was or how to get in touch with him.
    The following January I had a beautiful little girl who has become a very successful young lady who I am very proud of. I guess everything happens for a reason.

    1
    # 73975 - by Renee / October 12, 2024
    - Dating Disasters -
    Straight Female / 66

    Long Ago But Seems Like Just Yesterday

    When I was a senior in high school two of my friends and I along with a teacher chaperone attended a journalism conference in April at a college in Virginia.
    The last full day we had a free afternoon and three college guys invited us to go swimming at a local river near the campus.
    At first our chaperone said no but after some pleading she agreed to let us go with a strict curfew time to return.
    Once we got to the river we swam for a while then ended up on the river bank with the guys on blankets sunbathing along with some casual kissing.
    After a while the guy I was with asked if I’d like to take a walk. I got up then he gathered up our blanket so I had an idea what he had in mind but went along.
    We walked quite a ways then found a nice place along the river and spread the blanket.
    Things started with just casual kissing but soon got very passionate.
    I had on a one piece swimsuit which tied around my neck so he untied it unzipped the back dropping the top exposing my tits and began playing with them as we kissed.
    When he unzipped my suit the rest of the way I knew where things were heading so I asked if he had (as we called them back then) a rubber.
    He had come prepared so off came my swimsuit. Then he removed his trunks so there we were totally naked in the outdoors.
    It was so exciting that I got extremely horny and the sex was very intense and satisfying.
    Once things were over we returned to where the others were then returned to campus before our curfew.
    The next day we returned home and back to school.
    Two weeks later I missed my period. I had gotten pregnant despite.using protection.
    It was a big deal back then when someone got knocked up so mine was especially bad since I was knocked up by a college guy I had no idea how to find.
    The following January I had a beautiful daughter who grew up to be a very successful young lady that I very proud of.

    0
    # 73960 - by Renee / October 11, 2024
    - Dating Disasters -
    Straight Male / 20

    What Do I Do? Confused About My Feelings And Situation.

    Hey, I (20M) could really use some advice on a situation involving two friends, and I’m not sure how to move forward.

    I was best friends with a girl named Maya (21F). Over time, we became incredibly close, and she knew almost everything about me, including who I liked and how I felt about different things. She was someone I trusted deeply and shared a lot with.

    Then, through a college club, we became friends with another girl named Riya (20F), who was very introverted at first. But as we spent more time together, she opened up, and we all became good friends. Eventually, I started developing feelings for Riya. I was drawn to her personality and the side of her that only a few people get to see. I asked Maya for help in getting to know Riya better, since they lived in the same hostel and had grown close. Maya supported me and helped me understand Riya more, since I really valued the connection we were building.

    At one point, Riya mentioned that she was tired of guys proposing to her and only wanted friends, not a boyfriend. I respected that and decided to keep my feelings to myself, staying close as a friend instead. But things changed when Riya found out about my feelings through my WhatsApp messages with Maya. After that, both Riya and Maya stopped talking to me, and I felt completely confused and hurt.

    Later, I found out from a mutual friend that Maya actually had feelings for me all along. I had no idea when I asked her for help with Riya, and I realize now how difficult that must have been for her. When I first found out, I was angry and confused, but knowing about Maya’s feelings made me feel awful for putting her in that situation without knowing.

    Now, I can’t stop thinking about Riya. I know she’s not interested in me romantically, and she hasn’t replied to any of my messages. But I can’t seem to move on. I don’t even care about a romantic relationship anymore—I just want to be part of her life, even in a small way. I want to be someone she can trust and talk to, someone she can turn to when she needs support. I miss hearing about her day, teasing her, and just being someone she confides in.

    I’ve been sending a text apologizing every day, hoping she’ll eventually forgive me, but so far, nothing. It’s hard to focus on myself because she’s on my mind all the time—when I’m out walking, eating, or even just going about my day, everything reminds me of her. I just don’t know what to do anymore.

    What would you do if you were in my situation?

    2
    # 73841 - by Loidyor / October 5, 2024
    - Dating Disasters -
    Straight Female / 29

    Today's Woman Is Screwed, College Men Our Age Are Pussies

    This is not political, but it does have political overtones. I did go to college, but not one of those you think of. My college experience was working part time as a cashier at the Albertson. My beef, is that the college boys are sissies. The 'men' I meet are all blue collar.

    I don't want to be earning more than the man of the house. But I will not tie myself to a sissified know it all. The engineers I can go for are all older, a generation older. I can even go for a wimpy accountant of the prior generation. But not some mealy mouthed progressive.

    Sorry to mouth off here, but the only 'good' sex I can get is from a married older man, or a union pipefitter. I'm just not marrying a man without an education.

    3
    # 73822 - by Alexandra / October 4, 2024
    • - Dating Disasters -
    Straight Male / 61

    I'll Always Remember

    This is a true story. About 20 years ago I was dating a highly sexed woman, she was 15 years my junior and very adventurous. We had many memorable adventures but one has always stayed with me. We pulled into a layby and quickly undressed, she was laying on the back seat and I was fucking her when a face appeared at the side window. A man was peering in which didn't phase us as it had happened on a few occasions. My gf decided to open the window a crack as they were steaming up so his view wasn't impeded . I was putting on a good show but was well aware it was my gf's body he was interested in. Suddenly she decided to fully open the window which made me uneasy. His hands were groping her tits and then he lent in and kissed her. I was still fucking her when he opened the door and before I could object he had offered her his cock which she started to suck. I remember feeling jealousy and arousal in equal measures. His hand made it's way down her body squeezing her tits, over her stomach to rest on her engorged clitoris and with circular motions and my cock thrusting in and out of her she had a extremely strong orgasm. He was kissing her again when she whispered something to him. I watch as his fingers headed back towards her clit but instead of resting there he flicked my shaft from her c**t and gave me a bj. Now this did shock me as we'd only had threesomes with girls and I wasn't prepared for it. The excitement was to much and I jizzed in his mouth and I remember confusion as I watched him swallow. My gf loved it however and managed to wriggle free and was on her hands and knees helping him clean me up with her tong. No sooner had I got my head around a gay bj when I realised he was behind my woman with his cock inside her. A steady rhythm had developed as he fucked her, her hand squeezing my balls as she looked up as me saying, 'ohhhh that some good cock'. Again I felt jealousy but this time with mixed emotions as I watched him pleasure her. He slapped her arse which instinctively made her turn over laying on her back. I looked on as his shaft disappeared from view as he lent forward and he gave me another bj. My gf was loving the gay scene and came again, this time I didn't cum mainly because he withdrew. He was really going for it and I asked him not to cum in her 'only if you lick my cum from her belly'. What could I do I didn't want her pregnant by another guy so agreed. He started to throb and then pulled out and sprayed her stomach with white pearl streaks. My gf sucked on my knob as I lapped up his spunk from her belly, mound and then the sight of sperm dripping from her fanny. That sight broke me and as the sadness engulfed me I felt the tip of his dick push against my anus. I just let it happen as my gf goaded him on. When he had enough he just pushed my ass away. He was in my gf's vagina again kissing her as he bred her a second time. Upon completion he offered his glistening cock to me and I not only cleaned him up but gave an enthusiastic bj to boot. As I struggled to swallow I watched as he again mounted my gf kissing her tenderly, this was the last time before he walked away whistling.

    0
    # 73770 - by Bren / October 1, 2024
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