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.

Payback Is A *itch

So I met her on the internet and her photos were of an insanely beautiful woman two thirds my age who claimed to adore older men. I was thirty and she was twenty. I was an idiot to think such a hot looking twenty year old girl would actually go for an average balding thirty year old man. I showed her my photo first and was blown away when she sent hers.

We decided on a very expensive restaurant (her suggestion) for our first (and only) date. I got dressed in a nice suit and she work a please-fuck-me dress that was more ass than class. The first red flag should have been that with her looks she was willing to date me. The second red flag should have been the choice of restaurants. She was handed the menu and I looked over mine. The least expensive entre was $129. A 16 oz soft drink was $9.95. She ordered two different lobster entre's priced at $169 and $189 respectively. She also ordered the seafood medley for $159 and two different assorted snack trays at $49 each and three different sides at $19 each. She ordered the most expensive champagne AND another rare wine for dinner and some cafe concoction I never heard of totaling . Between the three the beverages were up to $1400. Then she ordered the entire desert cart which came to $750. Meanwhile I had a steak dinner for $89 and two diet soft drinks and no desert so my bill came to $109. She just kept ordering and ordering. What she did not know is that after she ordered her first expensive item I realized this was not going to end well for me so I excused myself to go to the rest room but in reality I spoke to our waiter who was also a friend of mine. We had both worked together at another restaurant and I told them this was going to be separate checks. I explained what I thought my date was doing and suggested he cut her off. He then told me that she was a regular and this was her M.O. and always stuck the date with a huge bill that they sometimes were not able to pay. My friend the waiter then told me that she was in reality loaded so I should just stick her with the whole check. I did not want to go that far but I was glad for his advice and assistance. So while she was busy eating her desert and guzzling $850 worth of champagne I excused myself and met up with my waiter friend and paid my own check and he then directed me to the back door of the place. I was home and deleting my account from that dating web site and had blocked her from calling me before my waiter friend called me to let me know her reaction. She asked the waiter to check on me in the men's room knowing I had left fifteen minutes prior. He spent ten minutes pretending to honor her request before returning to inform her I was no longer on the property. She became enraged and he handed her the check for her meal which exceeded $2000. He then witnessed her attempting to call me and then attempting to access my account on that web site to say bad things about me on my wall only to find my account deleted. Then against my waiter friend's advice she called the police on me. The police came and she told them what happened then the waiter told them what she tried to do to me then they arrested her for wasting their time. I of course never heard from her again and she never returned to that restaurant.

  • What An Embarrassing Situation

    First, my husband and I have been separated for almost two years but have not divorced. Our two teenagers live with me so I have not dated even though my husband does.

    Earlier this fall my best friend who is divorced asked me to go to Las Vegas with her for the week of Thanksgiving. I thought a break would be good so I made arrangements for the kids and planned for the trip.

    We arrived the Sunday before Thanksgiving then for the first couple of days went sightseeing and hitting the different casinos.

    On Tuesday evening we went to one of the lounges for drinks while listening to the band. While there we were joined by a couple of younger guys who treated us to drinks and great conversation.


    When we were ready to leave the guys I had talked to mostly asked me to dinner the next evening. My friend immediately stepped in telling me she would be fine and go enjoy myself so I accepted his invitation.

    The next evening as I was getting ready she said she had a little something for me tossing it on the bed. I looked and it was a box of spermicide suppositories and a package of condoms. She said knowing I wasn’t on birth control she had gotten them for me She told me we were out of town so I needed to enjoy myself and get laid.

    I had never given a thought to doing anything but to appease her I put them in my purse never expecting to need them.

    My “date” took me to a very fancy restaurant where we had a bottle of wine then afterwards we went dancing at a local club he was familiar with where we had several drinks.

    Later we left and he drove straight to the condo where he lived.

    He fixed us another drink while we watched TV casually kissing then things got serious. After unbuttoning my blouse playing with my tits he ran his hand up my skirt beginning foreplay quickly getting me very aroused.

    I excused myself going to the restroom. I inserted a suppository then started to get a condom. Then I remembered I had taken them out looking for something in my purse before leaving but forgot to put them back.

    When I went back we went to the bedroom resuming where we had left off. I had told him I was still married but not that I wasn’t on birth control so I told him I had used the suppository but would like him to use a condom too but he said he didn’t have one.

    Things had gone too far to let that stop me so before long we were having intercourse.
    Being young he had tremendous staying power taking his time to completely satisfy me with a massive orgasm as he came in me.

    I went back to our hotel telling my friend all the details thanking her for making it happen.

    I had lunch with him again on Friday before we return home on Saturday but we’re not intimate again.

    Everything returned to normalcy until this past Tuesday when my period didnt come. I waited until yesterday before taking a pregnancy test which confirmed I had gotten pregnant.

    I will need to have an abortion since my husband would use it against me in a divorce settlement.

    What Happened Last Night?

    I was out clubbing last night. This morning I woke in a strange bed. my eyes blurry I heard a voice. 'awake now sleepy?'. I rolled over to see someone in the doorway. Blinking to regain sight the figure said, 'I hope you don't mind me wearing your shirt'. There in front of me a pretty face with long dark hair, my eyes lowering to the breakfast she'd prepared and below that a fine pair of long smooth legs. I sat up with the tray on my lap her laying beside me excitedly blurting out how good the sex had been that night. It had to be said although I remembered nothing my cock was aching and strangely so was my bum. As she spoke I noticed something. 'Is that a cock', I blurted. She allowed my shirt to fall open. Bloody hell', I shouted as I leapt from the bed. She explained that I had no problems with it last night and if that was my attitude I'd better leave. 'I'll call Peter, he'll be more appreciative'. Why I don't know but jealousy over came me and I heard myself begging him not to. WHAT!!!! She said she'd made up her mind and as I dressed she was on the phone to him. 'Leave your number on your way out I may change my mind'. I scribbled it on a piece of paper and left, well kicked out. I'm sat at home recollecting the morning to you with my phone next to me. I can't believe I'm waiting for this man to ring me back, What happening to me? Oh goody the phone., got to go.

  • Bad Feeling

    I have been dating a few women off and on none of the ones have really interested me so I’m pretty much with them for sex. I have one girl named Christine who’s a good looking girl brunette 5 foot 3 maybe 140 lbs. stacked with tits and an ass but just talks after sex and I’m pretty much done at that point. Besides the really good sex we don’t have much in common. I have a feeling that she kind of knows that I’m on the verge of replacing her with someone else. What got me a little worried is the last couple of times we had sex which was yesterday and this past Sunday she initiated it and had me raw dog her. Going at it she does all these great things then has me lay back mounts me and rides me to an orgasm and I shoot my load. In the past she has pulled off and sucked it dry cleaning me up. Last couple of times she rode me to completion and had me fill her up. On top of that she stayed on me and grinned away until o got hard again and we did round two. Again I cum and she stays on me rubbing herself and her massive tits are hard not to play with. It wants until i mentioned this to my buddy that he sod she may be trying to trap me. I ignored her last few texts and now that all I can think about. Problem is she is good looking and if I’m not on the room with her I can ignore her. If she is with me I want so badly to be inside her and she as well. Kind of fucked up but needed to get that off my chest.

    Bus Ride And Bad Decision

    At the age of 16 I was a girl on top of the world. Youngest girl on the varsity cheerleading squad and very popular. Then came a Friday night bus ride...
    Long bus ride home after an away game. A cute senior star player asked me to sit with him. He and his buddy had one of the back seats. I sat on his lap for most of the ride. We made out some and his hands wandered but I didn't mind. I wasn't wearing a lot as I was still in my cheerleading uniform. Finally his hand got inside my panties and from there things went south. At least thats how it ended up. I have to admit I knew what I was doing and at the time, I enjoyed it.
    He kicked his buddy out of the seat, put me on my back and slid my panties off. He fucked me right there in a packed school bus. Of course a half dozen kids watching had their cell phones out taking video. By Monday morning half the kids in school had the videos. Suddenly I was the schools 16 year old porn sensation. It gets even worse. Teachers found out about the videos and I ended up in the principals office. The Police were called because I was 16 and it was considered c********n. Some kids and adults that shared the videos actually got in some real legal trouble. And as you can imagine my parents were not thrilled at my new found porn fame. Our relationship was never the same again.

  • Birthday Party

    I have a really close friend from work who is in his early 40s. We met at work and found out we have a lot in common. He has a family wide very nice and 2 kids 12 and 16. The 16 year old had just turned 16 and had a sweet 16 birthday celebration. I didn’t realize how big this is. She was dressed in a huge dress crown rented a hall food lots of booze I mean it was like a wedding. I was amazed of how big this was. I’m single and was hanging out at the bar with other friends I knew and some I didn’t. I had a few women walk pass and make eye contact we chatted and then had one hot shower brunette in a very tight black dress. She had small tits but a very large ass and a skinny waist. I had seen her earlier and every single guy and some married had tried to hit and talk to her. We chatted at the bar I asked to buy her a drink she said she would take a water she was hot from dancing. Her name was Erica she was beautiful. Big browns eyes tight body and lips that would look perfectly around my cock. We talked and flirted she asked went and danced and we made eye contact with me over and over. She gave me the I’m hot wave and made her way back to me before she got to me I had got her a water. She thanked me and by this time it was dark the music was blasting and it was very hot. She asked me to step outside with her since it was hot. The parking lot was full we walked around and I showed her my truck. I went in and gave her a kiss and she kissed me back. It was nice and this went on for a bit. I asked her if she wanted to get into my truck or walk back inside. We ended up in my truck and from kissing to feeling each other up eventually ended up in my back seat. Her skirt was hiked up I gave her pussy a lick and she sucked on me for a bit. I was hard as a rock and ended up having her lay back down and my dick head was at her pussy lips. I did not have condom and was not going to let this stop me. I stared kissing her neck and her and slid past her lips. She let out a loud moan and I stated fucking her. When I pulled out she was lifting back with me she was tight. I felt her start to tense up and shake a bit she bit my shoulder and let out a little moan and I shortly after unloaded deep inside her. We kissed and got dressed when her phone lit up. She answered and said I’m in the bathroom il be there when I’m done and hung up. First thing I said was don’t have a boyfriend she said no it was my dad asking where I had gone. I said oh that’s nice and left it at that. We exchanged phone numbers and kissed and the kissing led to round 2 and another load. In the middle of everything she had lost her panties so she went commando back into the party and said for me to wait a bit before I came back in. She would meet me at the bar in 20 minutes. I did that I found the panties decided to take a whiff and kept them. Made my way back inside to a beer. The birthday girl was walking around saying thank you and talking to everyone. She had a group of friends with her. Erica was with them the birthday girl came up to me and introduced her best friends older sister to me. Apparently she is 17 and her beat friend is 15. The girl I had just fucked was only 17. Not sore of this is a good idea but she ended up leaving with me again and had round 3. I dropped her off at home and this morning am wondering what to do. Normally I would be stopping but the sex is amazing and she is a couple of months from 18 and all I can think about is i did not use a rubber.

    What Started Out On The Wrong Side Of The Law

    In college I met this girl at a party. She told me she was a freshman and was 18. She was very attractive and affectionate. We went to my apartment and woke up with her. She was upset and very anxious the next day and asked me to take her to this neighborhood and drop her off at a gas station.

    I was contacted several weeks later, by the police. Statutory r**e, perversion of a minor, she turned out to be a recent 16 year old. She did get pregnant although she had told me she was on the p!ll. I was offered a plea deal. Marry her, support her, and keep my mouth shut. I took her to live with me when she was 19 once I had graduated.

    That was in my college days. I felt trapped, my life derailed, an accusation that wouldn't die. She went to college while I worked. We found this lady to care for the child while she was in school. Little by little I accepted my predicament, actually beginning to like her, enough that she moved into my room. As the years passed she matured and was most definitely a woman when she let me know she wanted to grow our family.

    Now, and it's a quarter century later, nothing but immaturity was ahead for me. This girl, who pretended to be a woman, became a woman you can't believe. It's because of her that I'm standing here today, a gainfully employed, husband and father. I told her many times but it rolls off her back.

    I’m A Nervous Wreck

    Over the weekend I had a date with a guy I’ve had a major crush on for some time.
    I let him go further than I’d ever gone with a guy getting me very excited.
    I decided to let him take my virginity then he didn’t have a condom but he promised not to cum in me so I trusted him.
    The sex was unbelievable then he said “get ready” shoving it deep inside me.
    I yelled “No for him to stop” but he came.
    I got the morning after pill the next day but it said if you’d already ovulated it may not work.
    My period is due this coming weekend so I had probably ovulated and I worried he may have gotten me pregnant because I was enjoying it so much.

    Torn Between Him And Her, I'm At A Loss Moving Forward

    One weekend I lost my virginity to the roommate of a guy who had dated my sister. The next day my best friend while comforting me came out declaring her love for me. You can well imagine, the weekend was emotional windsheer. I truly cared fir my best friend, I loved her. But did I want 'her' like that? How about having had virginity ending sex with a guy.

    Because she and I had a ling standing personal relationship morph into an intimate relationship. For some reason, physical intimacy with a woman was not as difficult as the same with a guy. Lots of reasons given, but I slipped into being with her, and loving her was natural.

    As we went out into the real world, buying a house together, and then getting married, the pull on me to have a home like my parents, children around the Christmas tree, new bikes, dolls and books to read. I wanted to live the life I did as a child. We investigated the adoption route, the donor route, the personal sex route, but none of those gave me a father at the table.

    Sex had become standard, a couple of times a month. Our social circle was one hundred percent women, some obnoxious, some near and dear. But no man at the table. If I wanted a home with a man and father I had to go that route.

    After a year I met the man for whom I wanted to carry. We had to divorce in order to get married, or have my children out of wedlock. Getting pregnant pushed the issue onto the front burner.

    Divorced, and married, two children and a house in the suburbs, I left my husband for my exwife. I can't please myself, my ex or my husband. I'm overthinking, and torn from my husband's presence. My table has no head, my children need their father. My home is not what I dreamed of. It's me, I can't leave them, not my home, not my children, not my wife, not my husband.

  • Big Mistake

    For the next month I am going to have the same words running through my head constantly. "It's OK honey, he doesn't want one". It's going to haunt me, I know it!
    It's my fault I admit it. I wanted to see it and she gave it to me. I have dated the same girl (Trish) for several years and we are engaged to be married. We have always been open about our sexual fantasies. Finally we took the step of joining a swinger website. Like a lot of white guys I have fantasized about seeing Trish taking a large black cock. Well we arranged it.
    There I was sitting in a chair, in a hotel room, watching my naked fiancé making out with a black guy. Sucking his very thick 9 inch cock. Finally she was laying on her back with her legs spread wide. The guy was rubbing his cock on her pussy as she asked him if he had a condom. I stood up and offered to get one. As I was going through our bag I heard Trish say "it's ok honey, he doesn't want one". I was freaking out as I looked back to see the guy pushing his raw cock in her pussy. Trish is not on birth control! I don't even get to fuck her raw, we use condoms.
    I watched as the guy pounded her pussy like he was trying to ruin it. Trish was screaming like an animal. Maybe 10 minutes the guy loudly announced he was cumming. Instead of making him pull out Trish begged him to cum in her pussy. The guy didn't miss a stroke. He kept fucking even harder after he came. Cum was being pushed out around his cock and both of them were a creamy mess. Finally he pulled out and rolled over beside her. Trish kept her legs spread wide and had a huge smile on her face.
    I wish I could say that was the end, it wasn't. Trish asked the guy to spend the night! I watched as they kept fucking until around 2am. He unloaded in Trish's pussy 3 times. Luckily it was a king bed. Trish slept in the middle. At 7am I was woke up by the bed moving. I rolled over to see Trish on top riding the guy. After she milked one last load of cum out of him, he dressed and left. Trish didn't even clean up. She did offer to let me fuck her but I was in no mood.
    Now I have to live with a month of being scared to death she is pregnant. Not to mention if she is it is 100% certain its not mine.
    "It's ok honey, he doesn't want one". Can't get it out of my head!