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 Male / 31

Girlfriend Birthday

I started dating this girl and she was really difficult. We had been together for 9 months or so and I had plan a nice dinner and got presents for her birthday. The g*fts were wrapped and the cake was in the fridge. I was planning on making filet mignon on the BBQ and I had bought a nice red wine that we both like.

She shows up at my work in the afternoon and tells me that she is not expecting anything from me on her birthday and that she was having a get-together with her family and that I was not invited. I try to negotiate with her but to no avail - I was really hurt.

_______

It was a hot July Friday evening so I decided that I would not stay home and sulk. I went downtown to a martini bar and I started chatting with a nice looking girl. She was expecting to meet a guy on a blind date but he stood her up - we both laughed about it and started chatting. We ended up walking over to an italian restaurant and we had a really nice supper with a nice bottle of red Amarone.

We ended up walking to her condo for more conversation and drinks. After a while she handed me a toothbrush and told me that I could sleep on the couch. I did not really believe the "couch part" but I went along - after I stepped out of the shower she told me that I could sleep in her bed.

We made love all night and it was awesome ! The sex was really great !!! I woke-up the next day naked in another bed on my girlfriend's birthday - it was a bit confusing.

I went back home and that afternoon the girl texted me that she wanted to see me again - she had really enjoyed our evening together. I invited her to my place - I served her the filet mignon, the red wine and she even had a piece of cake (birthday cake) for dessert. In the evening we had a nude hot tub and we went up to my room and had more sex all night in my large king size bed.

________

The next day my girlfriend called me and she was upset that I had ignored her on her birthday. What a psycho - I drove to her place, picked up my things and told her to take a hike.

I now have a new girlfriend and it makes me realize how fucked up the other one was and how I stayed in that relationship for no reason.

2
# 56643 - by Luke / February 7, 2022
    • - Dating Disasters -
    Straight Male / 19

    I Let Her Go

    I recently met with a girl who liked me very much and I also liked her very much. She made it clear that she was interested in me by giving me lots of signals and always flirting with me. I don't fucking know why I never made a move. I had never been in a relationship and maybe because of that, I was hesitant. Or perhaps I'm just a coward.

    We were both at a party and it had been months since we met. She kept flirting with me but I never reciprocated even then. There was another guy who always competed with me in everything and would always try to assert his dominance over me. He was hitting on her even though he clearly knew that she liked me.

    Even when she was getting all the attention from him, she was focused on me only. She told me to meet her in private and confessed to me. But I rejected her even though I was as much attracted to her as she was to me. We went back and soon she was receptive to the other guy now and was flirting back with him.

    When the party ended, she went back with him. I heard her clearly mention booking a motel room with him. I'm sure they had sex that night. I went home and masturbated to the thought of it even though I was cursing myself.

    A few days later I saw them sitting together outside the boy's dormitory. When the guy saw me he started fondling her breasts. She giggled and tried to stop him but when she saw me, she kissed him with all her passion and grabbed his hand and put it in her skirt.

    I keep thinking about why I let this happen to me but I can't stop masturbating to the thought of her giving her love and her body to him. What is wrong with me?

    1
    # 56577 - by I hate myself / February 4, 2022
    - Dating Disasters -
    Straight Female / 28

    Post-Breakup Hookup Disaster

    I was feeling like shit after he dumped me and decided to get picked up at a club and possibly get fucked. Met a few guys and thought a threesome might not be such a bad idea. We talked and I got super drunk. They took me to an alley and fucked me there. I remember riding one of them while sucking the other but not whether they were wearing any protection or not.

    Apparently, I passed out and they left me there. I woke up in the middle of the night to a junkie or old bum humping my pussy. I didn't even come to my senses until he finished inside after which I screamed and pushed him off, flailing my legs and probably landing on his jaw and balls. I was too terrified and ran off without looking for my clothes. Just got my purse. My phone and all my money were gone but I still had my keys.

    The whole journey, I had to cover my tits with my hands and occasionally my purse which was too small. I had nothing but a ripped mini skirt on and everyone seemed to enjoy my public walk of shame. I was too shaken to even ask for help and no one even offered anyway.

    I thought I would at least be lucky to get home without anyone noticing me but unfortunately, the creep-neighbor saw me. He stuck around for my hand to slip and to get a peak. He got a good view while I was unlocking the door but fortunately, he didn't do anything.

    I think I need therapy. I'm never going to drink again.

    2
    # 56562 - by Terrifying Experience / February 3, 2022
    • - Dating Disasters -
    Straight Male / 49

    My Obsessed Assistant

    I used to be a professor at a college a few hours away, where I would have a different teaching assistant every semester. One of the assistants and I had sexual relations that I put an end to after a few months.

    Even after I moved away with my wife and son however, this assistant has continued to call me and text me, asking to come down and have sex.


    I told her I have no interest in fucking her myself, and would be more amused to see her fuck the students from the college. For the past 5 weeks she’s been sending me hundreds of pics and videos of her sucking off and fucking the men on campus.


    The best part about all this? My wife jerks me off while we watch her videos :)

    0
    # 56340 - by Mr. Dom / January 26, 2022
    - Dating Disasters -
    Straight Female / 33

    I Ended Up With A Man Like The Men I Grew Up With

    I went to college to be able to support myself and to do a job I liked. In my hometown women lost their virginity young and had children young and the man they had children with never married them. I'm talking about a steel town, the east end, and if anyone is from that type of town you understand why I went to college.

    I won't say I was innocent when I went to college, I lost my virginity at 14 to an older cousin and he loaned me to his friends. I escaped getting pregnant because my other cousin, a girl, got me on birth control because I was sexually active. I had brains, that's what got me to graduate and into college.

    In my freshman year, two weeks there I was taken into a room and made to perform oral and vaginal sex with this guy, the following morning anal sex. He had all my holes and that made me his girlfriend, his as in his. He liked me in my underwear, watching me vacuum, That's the kind of guys from where I grew up.

    I got out of college and I got a job working for big company downtown and then got transferred to the home office out of state. I had a new life there, no one knew about me or about how the girls are from where I grew up. I watched tv and read magazines and asked the ladies at the department stores how I should dress. I practiced my talking, I took lessons in speech so I wouldn't sound like I was from the other side of tracks. I bought a nice purse and a pair of fake diamond studs. I did not suck cock and I did not fuck. I kept this to myself.

    A man from work started to pay attention to me and he was nice, we went out on dates, I met his friends and when his parents were in town he took me to dinner with them. I told my friend about my family but never let him meet them for obvious reasons. After a year of dating him I let him have sex and I oopsed myself into being pregnant so he would marry me.

    Only after I got married did he meet my brother and they did not get along. My brother thought he was a sissy and my husband thought my brother was criminal. My brother got drunk the night before he left and he screwed my husband right up the ass and made him suck his cock. Turns out my husband was a sissy, it took my brother to prove it to him.

    I was on my own again, with a child. I got child support and all but I was still alone. I met this man at a birthday party for a little friend of my son's in day care. He looked familiar. He wasn't polite or nice, he took me by the neck and lorded it over me. After he screwed me he asked me if I knew who he was. He was from my hometown, one of the guys in my high school and he always wanted a piece of me and now he had it. I had to like it, he had me and wasn't giving me up.

    He makes fun of my ex husband and calls him a sissy. He is the one who takes my son to ball practice and is at all his games. He eats what I cook and doesn't complain. In return he gets me and I do his housework just like the girls in my hometown are taught growing up. He works for an exterminator company and I have a job that pays more than he earns so we live in a nice enough house. I never tell anyone that I earn more than he does. When he went into the Marines he got himself a vasectomy so my son is the only son he is going to have. And he is my son's real dad, his biodad is not into sports or any masculine activities now that he is an open sissy.

    1
    # 56319 - by Marion / January 25, 2022
    • - Dating Disasters -
    Straight Female / 19

    I Didn't Say No

    Well long story short, I was dating this guy for awhile when he suggested we go on a hike. We found a secluded spot and started making out. Nothing out of the ordinary. That's when he moved to unzip his pants and let his cock out. I was shocked, there was nothing to suggest that I was ready for this. "C'mon just your hand, I really need this, I'm so hard for you," he said.

    I didn't want to make things awkward, so we continued to make out while I jerked him off. It was taking some time, my hand was getting tired, so he was like, "Well maybe if you use your mouth, it'll be faster." I just wanted to get it over with, so I knelt down in front of him and started sucking him. He was moaning like mad, so I thought it'd be over quick. Then he pushes me off which made me confused.

    He brings me up and pushes me right up against a fallen tree. He pulled my tights and panties down so fast then had me bent over. I could barely protest before he shoves himself inside me. His groans of pleasure was the loudest thing around us. He wasn't a good fuck. There wasn't any rhythm, it was definitely just him using me as his cock sleeve.

    He pulls out, cums all over my ass, then leaves me bent over the fallen tree while he cleaned himself up. Once he zips up again, he outrageously says, "C'mon hurry up, sun's about to set."

    3
    # 56249 - by Rey / January 23, 2022
    - Dating Disasters -
    Straight Male / 29

    She Heard Wrong

    I met this chick at a bar, she asks me what I do, I say waiter, she hears writer. We fuck all night. She wants to read some of my writings, I have none. She finally realizes, waiter. End of the relationship.

    0
    # 56222 - by Nelson / January 21, 2022
    - Dating Disasters -
    Straight Male / 47

    I Won My Wife In A Lottery Of Sorts

    During my college years a group of friends and I decided to go skiing in Utah. We drove, four to a car and rented a couple of rooms at this motel. The idea when we left was that the girls would take one room and the guys the other but when we got there we decided it was time to pair up, all four of the double beds would have a boy and a girl and the girls were picked at random assigned to a given bed. The guys then got to pick the bed. For the girls tough luck, if they could horse trade out of the bed with another girl it was up to them.

    Her name was Paula and she was a nice girl from Corpus Christi Texas. She refused to admit she was a virgin but it was pretty obvious to me. She held her legs together as tight as she could and I had to break them apart by stiff legging her with my knee. That and a slap on the thigh. Once I was inside, and I was as hard as I had ever been, I was giving it to her as hard and fast as I could when she asked me to please not get her pregnant. I lost control at that moment and she got the full treatment, every last ounce of it. The rest of the night she was quiet and reserved.

    For the next three days all I got from her was her backside, which to me was new I had never done anal, but it was all I could get so that's what I had to settle on. She gave me a couple of reluctant blow jobs and she let me eat her out reluctantly too. I fucked her tits and got her face wet, she just didn't cooperate the way I wanted her to. Out on the ski slopes I kept her close and she let me teach her a thing or two and for meals and hanging around she did stay close to me. The three other couples did the same, except for the nighttime activities where they got it on while I had to spread her cheeks and go up her from behind.

    All the way back to college she sat up front beside me, by then she was a couple whether she wanted to be or not. When we got back I told her to get some clothes she was going to be sleeping with me at my apartment. I guess she had given up by then so she let me get to her right between her legs and fuck her the right way. We never did do anal again.

    Of course her worst fears came true, she was pregnant and we got married before the baby was born. She let herself get pregnant a couple of more times, and after about five years she came to bed and let herself without putting up any resistance. It took that long to break her in right and she was a good wife after that.

    We made it to our 25th this last year and we had a small get together and she had to recount how we met, keeping the bed assignment part out of the story. Now that our kids are in their twenties and God knows what they are doing and with whom, we behave like love crossed college kids for their benefit. She reminds the girls, doing it has consequences, they learned how to count a long time ago and know their mother was seven months along when she got married. The trip to Utah is not for an open discussion, it's just between us, and she will not talk about doing anal. It did not happen, as far as she is concerned.

    3
    # 56051 - by Steven / January 13, 2022
    - Dating Disasters -
    Straight Male / 63

    Keep Your Eyes On The Prize And Never Give Up

    I met this girl at a friends house. She was his cousin from across town. She filled my mind and I couldn't get over her. My friend told me where she went to school so I went there to wait for her to walk home. She was surprised to see me and told me she didn't have permission for a boy to walk her home. I asked my friend to tell her she needed to let me see her.

    Her mother told her that until she was older she wasn't to talk to boys, especially boys with a motorbike. And she wasn't ever to ride on a motorbike. My heart was torn out of me, I couldn't sleep, my friend told me to give up, she wasn't ever going to get permission to go out with the likes of me. Fishin' in the wrong pond boy, that's what my friend told me his father had said.

    I cleaned up, wore my best jeans, my sister cut my hair and she went with me to talk with her mother and get permission. My sister promised that she would be in the same room and that I wasn't bad like some of the other boys of my school. The answer was for me to stick to the girls of my side of town, this girl was too good for me.

    I wrote her a letter and told her I was going to college when I finished high school, just wait and see. To get to college I first had to join the Army to get the GI Bill. And she had no choice but to wait. I did my four years, two of them in Germany and when I got out I went to college and got a business degree. I married my sweetheart when I graduated and we are married today.

    And that's the way you do it. Boys from my side of the track never took no for an answer.

    1
    # 56029 - by Joseph / January 12, 2022
    • - Dating Disasters -
    Straight Male / 34

    The Nurse

    A few years ago, I was on Plenty of Fish and went on a date with this good looking girl. I picked her up, we went to a restaurant and I drove her back home. She was a nurse - divorced - really nice looking and fun - but she wasn't my type and I don't think that I was her type either. We kind of agreed to this by the end of the date. To my suprise when I got to her home, she invited me to come in and I agreed.

    It was a hot summer night - three Gin & Tonics later we are kissing in her kitchen. Eventually the clothe flies off and we had sex in the living room, in the shower and in her bedroom. This girl seemed really sexually frustrated and we had sex for a good 3 hours. The next morning I woke up with her tongue delicately licking my balls - I was hard as a rock - she sucked me to perfection.

    She made me a coffee and after an awkward half-an-hour of small talk I left. We never contacted each other again.

    0
    # 55987 - by Luc / January 10, 2022
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