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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 / 46

Dating Profile Joke

My dating profile was not too exciting I guess because I was not getting many responses at all and a few were very honest with me saying I looked like their dad. So as a joke I took some different pics showing me doing different things I never do, said I was looking for single moms because I was done having children but loved having them around, went on saying would prefer someone very orally talented and wants to be a stay at home mom. I received like seven requests to meet, ended up getting a blow job on the first date from two out of five of them and am currently still seeing one woman with two kids from separate dads and she blows me every time we got out. I am going to tell her she can move in and we can be together if she is willing to sign a very lengthy pre-nup, part of which is going to include some sort of lack of sexual performance clause just to see if she will go for it. She has told me she does not want to get married because she will lose a percentage of the child support, I asked how much a month are you talking and tried to hold back laughing when she told me it would be like two hundred dollars but one of the fathers would probably take her back to court for more off of it. I need more time to think about whether she is worth a life change for, just based on her physical attributes and sexual abilities my answer is yes but, we all know sooner or later all that fades away. All of this because I put in my profile I was basically looking for a cock sucking slut to live with me.

2
# 77655 - by Paul / March 19, 2025
    • - Dating Disasters -
    Straight Male / 54

    Didn't Ask For It But Loved It

    About 20 years ago I was teaching at a community college, and one young student just kept her eyes on me most of the class time. Gina was just slightly plush, brown-haired, and had a permanent sort of embarrassed smile, at least around me. She followed me in the halls sometimes to talk longer, and several times stood extra long after class to talk, or apparently just to be around me. She did fine in class, but almost immediately after the semester was over came to my office again to talk a long time, and said she'd like to talk more. I gave her my phone number and the next weekend she called me, asking where we could meet. I suggested a walking trail by the local river, and we met up for a pleasant stroll. Again, I kept feeling she liked standing and walking very close to me. On the way back I went all the way to my house, which was just a block off the trail, and she asked if she could come inside. She looked around for a bit and complemented me on my arrangements--which was actually just a rough bachelor's house, not very well-organized or stylish, but perhaps displaying my geeky obsession with books and maps, and hence the general academic style she seemed to admire in me.

    Only a few days later, she called me again in the evening, and asked if she could visit. I said I was winding down for the evening but if she could if she was nearby. "OK, I'm right here" she said, and indeed knocked on my door 20 seconds later. She admitted that she had already gotten here and just wanted to make sure she was welcome to visit. It was after 8, and I was already in my bathrobe, but she said she didn't mind at all. We sat and talked for a while on the sofa, but eventually she leaned in closer to me, which made my penis visibly twitch under my robe. She saw that, and with a quick looking up at me, where I must have given a kind of longing look in reply, she practically engulfed my dick in her mouth in a single swoop. She acted like a hungry cat finally getting a meal, and I just responded with a few moans and a gentle hand on her back. "Nice...nice..." was about all I said while she bobbed up and down, and after just a few minutes I tensed and started ejaculating into her hot mouth. She almost stopped moving but I pushed her to indicate what I wanted, and she resumed sliding her mouth back and forth as she took in my cum.

    She soon left, but visited a couple times after that, finally asking if she could stay overnight, which I said she was welcome to do. She slept in her panties though, never letting me even go down on her, though she did let me feel her over and once under the panties. Blowjobs both at night and in the morning that time. I soon started to feel that we didn't have that much more to talk about though, she wasn't mature enough to engage with me, and she must've felt that too as she just stopped calling a week later. Nice while it lasted though.

    1
    # 77567 - by George / March 15, 2025
    - Dating Disasters -
    Straight Male / 31

    Regretting It

    I have had a close friend that I have known for years. He has always had a wild side to him so when he got married all of our friends were surprised but supportive. He married a cute girl named Juiie. She was a fake blond shirt and kind of thick very nice set of tits. At times she looked a little frumpy but In skimpy clothes you could see she had some curves. I was in there wedding and after the wedding we carried on hanging out whenever we could. My buddy always seemed to check girls out when we were out as I did I got to go and got on them and he would flirt. 8 months into there marriage he brings up wanting to try new things. A few beers later he mentions that he and Julie would like to try and swap or share something. The more beers he has the more he is sharing. He shows me pics and short clips of he and Julie having sex and sends me nudes a few its just Julie with a dildo one had a cucumber shoved in her. My favorite one she is on all 4s and she has a fake cock in her mouth and another up her back side. It’s a 30 second clip and with sound she is really going at herself. I’m a man and anyone would ask what they wanted from me. Exactly what I did was ask how can I help. He says that she wants to be spit roasted and watched that type of porn. Ok il help why not 45 minutes later we are at there place and he is talking with Julie. To my surprise she is really into it. At first we where kissing then i started to undress. It was supposed to be a spit roast but to my surprise
    My buddy was just sitting back watching. At one point i am sitting on the couch no pants cock out with Julie slurping up and down on my cock. All she kept saying to herself was I knew it would be nice and big this is going to be fun. Looked into me eyes and whispered to me that she wanted me to own her. I said sure because I was close and a few moments later I held her head down and pumped streams into her mouth. Julie swallowed almost all and stood dropped her jeans and stood in front of me in her thong. Nice big tits hanging ass cheeks split by the thong. I smacked her ass a few times she came and laid on my lap. I played and fingered her ass finally put her on all 4s and licked away. Pussy ass she directed my tongue she knew where and what she wanted me to do. All the while my buddy still watching we both look over and he fell asleep. A little too much booze. Julie looked at me and said I guess you’re the only one fucking me. I hammered her pulled her hair stuck it in her ass rose her doggy style and her ass was beat red from the slapping. She enjoyed the fuck and I was rewarded with a soaking since she squirted all over us. We where both a sweaty sticky mess. We showered and she ducked me off in the shower. I pat out in the soare bedroom and woke up with Julie next to me. I woke Julie up with a stiff cock sliding into her she instantly started bucking back at me. I blew my sticky load inside her. I cleaned up and was headed out she walked me out and gave me a kiss and said we would do this again soon. My buddy was MIA for about a week when he came over and asked what happened that night. I didn’t hide anything told him what had happened. He was a kind of mad but said that it was his idea and left it at that. He has been standoffish since then. I know he was a bit upset but again his idea. A few weeks after I’m at my place and Julie shows up in a over sized sweater socks and sneakers. She walks in she asked me if her husband had been in contact. I tell her what I told her and he has tried to bring another guy in instead of me. I was a bit disappointed I thought we where cool and I even had offered to bring in a girl for him of that was what he wanted. She goes on to tell me that she hasn’t agreed and has shot him down every time he brings it up. He got mad when she said she wanted to only fuck me. They argued and wt about there business. She finished telling me the situation steps back and the sweater comes off and she is in sneakers socks and a g string. I could not control myself and i fucked her for the next few hours. We both cum at the same are sexual chemistry is on point. As she puts it you stick it in and I forget about everything. I make her squirt cum and want more. She squirted forms rough anal pounding. Soaked my coach with her juices. She has spent the night avoiding his calls. She makes her way to my work around lunchtime and blows me in the car in my parking garage. She has begged me to not let her go. I kept telling her what ever she wanted to hear to keep those ass cheeks open.

    1
    # 77531 - by Anonymous / March 14, 2025
    • - Dating Disasters -
    Straight Female / 18

    Hoping We’re Not In Trouble

    Last Saturday night my boyfriend, my little sister and I went to a Blake Shelton concert in NC.
    We spent the night at a motel after the concert and I let my little sister have a threesome with my boyfriend and I.
    I’m on birth control but it was her first time so he was using a condom with her but it broke when he came.
    Her period was due Wednesday but she still doesn’t have any signs that it’s coming so we’re afraid he may have gotten her pregnant. I’m hoping she’s just late but if he did we’ll be in big trouble.

    6
    # 77382 - by Abby / March 7, 2025
    - Dating Disasters -
    Straight Male / 38

    Don't Sleep With Your Stepdaughter

    We'd gotten so attracted to each other that we couldn't resist. Her mom was working late and we had the house to ourselves.

    We had just had our first orgasms. We were drenched in sweat, panting, holding each other as our hearts quieted. I told her I loved her.

    Then, the door opened and my wife caught us, in the bed I share with my wife. She hadn't had to stay at work as long as she had expected.

    Naturally, the marriage was over. She gave her daughter a choice: her or me. So, I lost my relationship with my stepdaughter, too.

    Nine months later, my stepdaughter gave birth. I never got to see my child-grandchild.

    Sleeping with your stepdaughter might sound hot in the moment, but it's just not worth the risk.

    6
    # 77286 - by Ringo / March 2, 2025
    • - Dating Disasters -
    Straight Male / 53

    Power Exchange

    Went to the power exchange in San Francisco about 24 years ago. Went with a gay friend of mine.

    This is a BDSM oriented sex club. We arrived and we striped down to just our shoes and had a towel we wrapped around our waist. They gave us condoms.

    He headed off to the gay area and I went to the straight area. It was awesome to see all of the debauchery. A bitch in a swing gettting her c**t fisted, a guy getting dommed by a woman shocking him with a taser, several couples fucking on these rubber beds, a Trans guy on his knees with several dicks circle jerking to his face with several loads on it.

    Lots of other horny straight guys like me but no other single straight women there. You either need to go as a couple or meet an arranged date there.

    I'm keeping my distance stroking my cock to the couples fucking and in walks 5 Asian Tranies. All but one were obvious with slight beards and overweight with skirts. It was funny but one was totally passable and hot. Hate to admit it it but heshe was hot.

    The 5 were flirty with all the fellas giving back rubs and attempting to grab all the
    straight guys crotches. The fellas were passing it off and moving away. All except me.with the hot one. Heshe was probably 5'8" 140 lbs, tight body with a tight fit mini dress and high heels.

    Since there was no action going and I was horny ass fuck to all of the debauchery going on I let heshe rub my back. I asked for a blowjob and heshe kneeled before me, started to unwrap a condom and I said NO condom. Heshe asked if I was clean and I replied YES. Heshe then took my hard cock in their mouth and sucked me so good. When I was about to nut I told heshe to swallow, in which they did.

    One.of the best blow jobs ever, but I felt horrible after knowing I got sucked by a dude. My gay friend came to get me as it was time to go. He told me about all his escapades in the gay area. Made me wish that straight people could have all of that sexual freedom with each other.

    I told him about my experience and how shitty I felt about it. He said, who cares, it felt good didn't it. Tis true but never did it again.

    Got married and tried to talk my wife into going there, no dice. Now with a GF and she isn't into it either. I want to go back. I feel the need to be both a voyeur and an exhibitionist sexaully.

    Don't think I could be with a tranny again, but who knows if I am horny and the mood strikes.......

    3
    # 77205 - by Anonymous / February 27, 2025
    - Dating Disasters -
    Straight Female / 18

    Honestly, I Didn't Know

    Three weeks ago, I dated a guy after a family wedding. Mom was showing photographs from the wedding. She is picking out people. I apparently fucked moms second cousin's son.

    8
    # 76924 - by Katie / February 16, 2025
    - Dating Disasters -
    Straight Female / 23

    I Didn't Know He Was Married

    He could never invite me over to his place because he had roommates. Indeed. A wife and 4 young children!

    He always wanted to take me out for dinner and then fuck me back at my place. He said he couldn't spend the night because he had trouble sleeping and it was better in his own bed.

    I really don't know what to do now. We are in love. We realized during the first week we were dating that we are soulmates. It's stronger than his marriage and it's not something we can end.

    He says he stays with his wife only for the kids. He has promised to tell her and start the divorce. I want to message her on Facebook and tell her, in a kind and nonjudgmental way, that he's now engaged to me.

    He doesn't want me to date other men, and truth be told, I don't want to, either. His is the biggest Penis I've ever had. He touches a magic spot inside me like no one else.

    We are slowly making long-term plans. I'm not interested in having kids or parenting another woman's kids, so he plans to just give his wife full custody. If she doesn't want custody or can't manage, he'll argue for putting the kids up for adoption.

    We want a destination wedding in Cancún.

    7
    # 76707 - by Lucy / February 9, 2025
    - Dating Disasters -
    Straight Female / 75+

    Today’s Female’s Are Very Fortunate

    In 1957 I was a junior in high school. I didn’t date steady preferring to play the field. I had made the cheerleading squad which made a girl even more popular with the sports guys.

    Casual sex wasn’t as excepted back then as it has become today due to the lack of means to prevent getting pregnant. If you did mess around it was with a rubber (what a condom was called back then) or the guy pulled out before cumming in you.

    I had managed to avoid having sex mainly due to the fear of getting pregnant but also because once you did guys didn’t keep it a secret they had gotten it.

    During basketball season I started seeing one of the players on a more regular basis so we began some heavy making out but still I wouldn’t go all the way.

    One night we were parked making out then I got very aroused when he was fingering me.
    When he said he had a rubber I gave in losing my virginity.

    It was very exciting and pleasurable until the rubber broke just as he came. There was nothing you could do in those days but wait and pray for your period to come.

    As my luck would be I got pregnant my very first time. That was a very embarrassing thing getting knocked up back then with no choice but to have the baby.

    II had a beautiful baby boy but the guy who got me pregnant never had anything to do with us. His parents paid my medical expenses but I never got any support of any kind from him.

    1
    # 76465 - by Nancy / January 29, 2025
    • - Dating Disasters -
    Straight Female / 42

    Thought It Was Going To Be My First Time.

    I've been reading these dating disaster and kids stories. Took me back when I was 15. I had a few giggles and memories. Dad took mom out to celebrate their wedding anniversary. I've been seeing this guy from school. He was a year older. I thought about it gave him a call and invited him over. I dressed to be fucked. Gym shorts no underwear a school gym shirt, Wore one of those fancy front hooked bras for easy removal which I coped from my mom. We had an entertainment room in the basement. We started out there. On a couch and watching a movie. We started making out. About ten minutes later I told him there was a bedroom down the hallway. I smiled at him. And I led the way. We laid down and resumed the fourplay. Off went my shirt and bra. We're kissing and he's rubbing on both titties. Finally, he got brave and wanted to remove my gym shorts. I raised my lower body for easier removal. Felt his hand go between my legs. He found my opening and started rubbing. I got wet and there goes a finger inside and my nipples got hard. I even took time to play with both titties. I couldn't stand it anymore I looked up and said fuck me. I watched him stood up and watched him undress. I viewed my first guy hard on. I raised my legs and reached up for him. He took position between my fully spread legs. I then felt his dick at the entrance of my willing body. Then I heard a door open from upstairs. My mom is yelling anyone at home. we were scrambling to get dressed and get him out the basement door.

    2
    # 76456 - by Charlene / January 29, 2025
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