Adult Confessions

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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 / 28

Bad Decision, Now An Obsession

This story goes back 12 years. In todays high school world it is popular to be "trans or non binary". A few years back it was popular to be bisexual (I know from my niece). Well back 12 years ago in order to be popular or one of the cool girls you had to date or fuck black guys. In my parents house bringing home a black guy was not an option. But I wanted to be one of the cool girls. Didn't quite work out that way. I was 16 and dumb.
There was a stairwell in the back of the high school where all the really hard core black guys hung out, skipped class and smoked weed. Please don't take offense at my french here. These guys were "n*****s". Dressed the hip hop, thug part. One day I got up the nerve and went into the stairwell. I was immediately confronted by 2 boys. I was so nervous I decided to just walk by and head upstairs. One of them grabbed me by the arm and started feeling me up. He pulled me under the stairwell out of site and told the other boy to keep watch. He pushed me up against the wall and groped my tits as he kissed me. I tried to push him away be he wouldn't stop. He got the front of my jeans open and pushed me to the floor. I was on my hands and knees as he pulled my jeans down to expose my ass. As I felt his cock start pushing inside me I could tell it was much larger than the white boys I had been with. During this he kept yelling things back to the boy keeping watch. Things like how tight my white pussy was, how he was stretching my white pussy, how he was training this white bitch. I cried a little and felt ashamed. I was being used like a piece of meat. I began begging him not to cum inside me. He told me to "shut up bitch". When he came he yelled "this bitch is having a black baby". After he got up and walked off like nothing happened. I pulled up my jeans and spent the rest of the day with cum leaking out of me.
And yes, a few weeks later I missed my period. I wasn't one of the cool kids. My parents were less than happy I was pregnant, but went meltdown after i told them the baby was black. Went to a clinic and made it go away. We moved shortly after that.
Problem is no matter where we lived I kept fucking this exact type of guy over and over. Only difference was I was now on birth control. My relationship with my parents was crap. I left home after graduation.
I never married or even had a real long term boyfriend. Nice guys don't exactly like the fact I have this habit of fucking this type of men. But it meets my sexual needs.

3
# 69065 - by Girl / December 12, 2023
    • - Dating Disasters -
    Straight Male / 36

    Shaggy Dog Date

    I once went out with a woman who seemed extremely hot for me, and wanted to come to my home that very night. We made out a bit, she let me feel her up bottom and top, and even stripped off her underwear, but wouldn't let me fuck her, even though she said she really wanted to cum. I offered to go down on her, but she drew the line there too and left us both hanging.

    This strange behavior was puzzling. I couldn't make heads or tails of her.

    4
    # 68809 - by Harry / November 28, 2023
    - Dating Disasters -
    Bi-Sexual Male / 32

    A CONFESSION

    Here goes. I have a stroke buddy. I'm married and have been letting him stroke the gay out of me for 3 months. The other day he persuaded me to suck his cock whilst he pumped away at my dick. So what I hear you say. The fly in the ointment is that after he fed me his juicy fluid and he'd he'd brought me to another gay orgasm I noticed my wife watching through the patio doors, CAUGHT.

    5
    # 68776 - by BUDDY / November 26, 2023
    • - Dating Disasters -
    Straight Male / 65

    Well Endowed Blues

    Well Endowed Blues

    I’m 65 years young. When I went through puberty, my body went through big changes, the most noticeable of which was my penis.
    I became the locker room joke. I was six foot six inches tall but was mostly known for being well hung. A flaccid 6 inches in length gets you noticed with an erect girth of 6.5” and 9.5” inches long … let’s say, word gets around fast. In high school the girls wanted to date me just to see what I was packing. Of course back in the 70’s jeans were very tight and the side I favoured was very obvious. They were never disappointed until they actually had me attempt to penetrate them. “I’m sorry … it’s too painful” was a common complaint. As word got around, I even had two female teachers, one an art teacher and the other science, seduce me in their want to ride my pony. The art teacher was able to handle my mass with her and I getting it on a dozen times or so. The science teacher, try as she may, realized the physics of fit, did not work out. She loved to jack me off and she taught me how to eat pussy but penetration of more than 20 seconds was unbearable for her. I can’t tell you how many women I dated in my life, who when they cast their eyes on my erect unit, simply said, no.
    I’m writing this because young men who wish they were well hung should know the reality of what it, being well endowed is, not what they imagine it being. My girth alone cut out blow jobs for me altogether and 90% of vaginal penetration. Anal? Forget about it! I’m not gay but I’d say if I were, the problem would be the same or worse.
    Life is not what you see in porn. I’ve had a ridiculous amount of hand jobs in my life and was lucky enough to have found a beautiful bride who is 6ft tall and capable of taking all I can give. Believe me when I say, I would have given anything to be average.
    Just sayin…

    3
    # 68750 - by Big Jake / November 24, 2023
    - Dating Disasters -
    Straight Male / 22

    Hard To Take Seriously

    I just recently came into a situation that I find weird. My best friend has started to date exclusively a girl named Anita. I know her and my best friend know her. The thing is in high school and college we all remained friends with benefits. Yes I fucked her he fucked her and another one of our friends fucked her. We would literally just kind of past her around. She is hot taller 5 foot 7 small tits thick thighs large bubble but. We have took her to spring break and we did her that week sometimes me on one end and him on the other.
    I have been in every one of her holes and I am sure lots of guys have as well.
    We all met together at a bar last night and he showed up with her. I didn’t think anything of it. A few of us went back to my place and by the end of the night I had her bent over on a lounge pumping away and then she let another one of my friends mouth pump her. My best friend was inside kind of drunk. After a while we went back in and she went right over to him. I didn’t find it weird I figured she was going to fuck him to. That’s when he said we should get going and he mentioned to us that they had started dating. My other buddy and I looked at each other and then at Anita and we were like WTF. She excused herself to use the restroom and I followed behind. She stopped me when we where out of sight and said that yes they where dating but that would not change anything between her and I. I told her that’s not dating. I told her that her and I could not hook up anymore and I wouldn’t have fucked her earlier if I had known. She confessed that she had a thing for me and my buddy and that’s why she did anything we wanted for us. I was totally confused she begged me to keep everything that same and started to rub my cock. It felt good and I made her blow me in the bathroom before I pulled her up and spun her around. I was rough with her but and pounded her hard. I blew my load in her but and made her not clean up and walk out. Before she walked away I told her that she would be staying the night. She nodded and stayed. I used her holes last night and left a few minutes ago. She said that she would be back around 3 to pick me up for thanksgiving. I will be going with her to her parents home. We had a conversation and basically told her that I would be the one pumping her from know on. She agreed and said that she would talk with my buddy later this morning. She mentioned that he kind of knew what her feelings where for me so it would. It be that difficult of a situation. I’m not sure what kind of relationship I have with Anita but I know I like to fuck her and she like me to as well. I do like to see her get fucked so maybe this will all work out.

    2
    # 68734 - by Bobby / November 23, 2023
    • - Dating Disasters -
    Straight Male / 41

    I Am In So Much Trouble

    I fucked my buddies 17 yr old daughter. I can't say I regret that. Wow it was the tightest little pussy I ever had. At a ballgame the other night she caught me in the parking lot and asked to hitch a ride home. Next thing I know we are in the backseat, her legs in the air and a tight little pussy with a death grip on my cock. I looked down at her and told her I was about to cum. I was gonna shoot a big load on her tummy but I got a surprise. She grabbed me around the neck, pulled me down and wrapped her legs around my back. I was shooting my load in her pussy as she milked every last drop out of my cock. I felt GREAT but she isn't on birth control. I am not a religious guy but I am definitely praying now...

    2
    # 68696 - by Me / November 19, 2023
    - Dating Disasters -
    Straight Female / 24

    One Night Stand In Miami

    One night, I was out with friends. Some guys came on to us, we drank tequila. One guy put his arm around me and walked me off to one side. My purse was on the couch so I tried to go back to it, but I was on the street, in a parking lot, in a car, at an apartment. What I did I don't know, what he did I had semen in both my vagina and my anus. I woke up in a field by the freeway.

    The lady doctor at the ER who examined me told me I was another one that night, did I want to talk to the police. Could I identify him? No. Could I tell them where the apartment was? No. What kind of car? No. My memory was up to when they hit on us. Video inconclusive, ball caps, dark glasses, kept his back to the camera. On the street one more of a hundred people, half drunk walking around, getting in and out of cars. No video of the car I was in.

    Embarrassed? Angry? Not really. It was Saturday night. A one night stand.

    5
    # 68688 - by NoName4Me / November 18, 2023
    - Dating Disasters -
    Straight Male / 31

    First Date

    I met this woman at a coffee shop and we started talking. We found out we were both single and she actually asked me out. The next we went out to dinner and back to her place. She mentioned she likes to know what a man likes before she has any sexual relations with him. She told me the best way to find out was to watch him masturbate and tells me to do it for her. I dropped my pants and started stroking but told me to fully undress and show my body off first. I stood in front of her showing myself off. She then told me to start masturbating again. This was actually the first time anyone had watched me do this. I was a little embarrassed at first but as I continued that feeling went away. I finished blowing my load on her coffee table like she had instructed me to do. I cleaned up and she told me to stay undressed.

    A half hour had passed and she said she wanted to see if I could do it again. It took longer for me to do it but I did cum again. At this point she told me it was getting late and we ended our night.

    I received a call from her the next day asking for $500. I asked why and was told to keep things private. I told her I didn't know what she meant and I don't hand out money like that. She said fine and I would find out why soon enough and we ended our call. She texted me a link and said others would get it too if I didn't give her what she asked for. I wasn't going to give in and said she was getting nothing and we were through.

    I went to the coffee shop to possibly see she her again and talk to her but she wasn't there. One of the barista's mentioned my girlfriend was in earlier and said I was too much of a pervert to date. She then tells me the video she showed her shows it. She mentioned the other baristas think so too. I tried to explain she was blackmailing me for money. A guy in the line was overhearing our conversation and just asked what this woman looked like. I started to describer her and then he added some things to the description mentioning we might have both been taken advantage of by the same woman. We compared our descriptions and it was the same woman. He said he went to the police and logged a complaint but they said they couldn't do much. He asked much money she got off of me and I told him I refused to pay. He said he lost a $1000 to her and even though he paid she still posted his pictures.

    We had a coffee together and discussed things further. He said she send links to the video to his company and family so quite a few people have seen it now. He said his company and family understand but it doesn't change the fact that they have seen him doing what he was doing. When I asked how bad and embarrassing his video was he pulled out his phone and showed me. His was a lot more graphic and more out there than I would ever do. He asked me to show him mine. He said he was part of a support group and they told him the best way to get over it is to start accepting it happened. I showed him the video and he said I should join his support group. I declined at first and then went.

    I went to this support group and there were 8 of us. They each spoke and I spoke last. They had me explain everything that happened and then had me show the video. It was weird to say the least but once they finished watching the video they wanted me to reenact what I was doing. There were 4 of us guys in the group and they said they would do it with me. I thought this was a joke a but the 3 other guys began undressing. I was in shock and they came over and began undressing me. They started stroking themselves and when they saw I wasn't they came over and began stroking me. At the end of this they had made me cum and they didn't themselves. They got dressed while i was still in shock. They began to say that this was my first step to accepting what that woman had done to me. I put on my clothes and left and never came back.

    I felt I was violated a second time but this time may have been worse. This time I was undressed by 3 other men and then they literally took matters in thier hands.

    3
    # 68645 - by Bob / November 15, 2023
    - Dating Disasters -
    Lesbian Female / 39

    I Can't Believe It,

    I went to a party for a coworker, met a guy and woke up in bed with him. I'm pregnant.

    3
    # 68633 - by Michelle / November 14, 2023
    • - Dating Disasters -
    Straight Male / 18

    AFTERWARDS

    My buddy and I met two sisters at a club in town. It was going well until their bf's turned up and threatend to give us a good hiding so graciously we retreated. We went back to his place liking our wounds. I was lying in bed and heard something so got up and followed the sounds. upon opening the door I was confronted by my buddy having a wank, the suprise tipped him over the edge and I stood there watching as he shot his sperm over his thigh. He looked up at me with that I've been caught look on his face. I told him not to worry, we all do it. 'But do we all lick it up? because I'd like you to'. It was my turn to be shocked. 'Come here', he said assertively. I found myself kneeling on the floor by his bed inches from his liquid. I took a long look at his limp cock and his coated thigh. I could smell him, his scent, and then I lapped up the first of his spent seed. The taste intoxicating, so much I went for seconds, then thirds, then the rest until there was no trace left. My brain was fuddled I had to suck and clean that cock which I did until he became erect again. My head against the bed he proceeded to face fuck me then I was bent over the bed and I allowed myself to used and climax inside me. I was taken to his bed and used many times like a cheap whore that night and again next morning. We haven't spoken of it since but I have the feeling he'll want to use me as a bottom again

    0
    # 68570 - by Buddy / November 10, 2023
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