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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 / 34

Making Lemonade Out Of Lemons

As a freshman in college I got knocked up my first semester. He had another freshman girl pregnant from summer school.

She took me in, when her daughter was born I babysat for her while she went to school. When my daughter was born we scheduled classes so we sat for each other. We finished in four and half years. We moved after college, raising our daughters together. The girls are now 16, sisters from another mother.

Daddy buzzes around, he pays child support and steps up for the girls. His wife has welcomed them on visitation, and summer holidays.

We don't need a husband around, our little family is all we need.

0
# 48393 - by Mia and Bethany / December 10, 2020
    • - Dating Disasters -
    Bi-Sexual Female / 23

    The Truth Hurts

    I got a knock on my door. A well dressed girl asked if she could talk with me. I was in college then, she said she worked at a bank. The topic was a guy I was dating. She had dated him too. She warned me, he was going to break my heart. He was married to her.

    That's how our friendship began. Over a guy. Over time our friendship became personal, drowning our attachment to him with each other. Long afternoons in bed, talking, caressing, love making, promises of our true love. Nights, in bed with him, from flower to flower, in and out with her, in and out with me, intense sex with him, relief loving sex with her.

    She confessed to me last weekend during one of our afternoons that she had first seen me, she had first wanted me, she had sent him to seduce me, to compromise me by having sex with a married man, so she could seduce me. If I loved her like I said I did I would understand. I feel used, lied to. The fantasy is crushed.

    2
    # 48361 - by 3some / December 8, 2020
    - Dating Disasters -
    Straight Male / 27

    We Score With A Married Woman

    I've been trying to get with this hot new girl at work for a few months now, flirting through instant messaging and text and trying to make excuses for her and I to meet in the office if possible. Finally after a couple of weeks she agreed to meet at the office to go out to dinner.

    We went out to dinner but then I planned on us watching a movie back at my apartment...there wasn't much else we could do out right now, but I also assumed that if we hung out in my apartment I'd have a better chance of scoring.

    It worked great. She wore a mini skirt to dinner so when we got to my place she wanted to get under a blanket in front of the TV. That put us right next to each other under a blanket. To get comfortable she sat with her legs tot eh side on the couch and backed up to my side. My arm naturally landed over her lap with my hand on her thigh. She moved around a little to get comfortable and I think to give me ideas, and let her skirt ride up so my hand was on bare thigh and my forearm touched her thong in front. We didn't really kiss, but by rubbing her thigh and asking if she liked it, it didn't take long for me to pull her thong to the side and begin fingering her.

    We sat like this for a while until she said, "that feels so good." She twisted around so now my hand was on her ass and she went for my erect cock. Within a minute or two she was going down on me while I played with her pussy from behind.

    Just as we started, my roommate came home. He wasn't supposed to be there. He came in and said immediately, "She's fucking HOT!" My date pulled her head up and said "Thanks" then went right back down on me. Without asking, he walked around to the other side of the sofa to stand behind her. She stopped and looked back at him and said "Yes, please!" and went back to blowing me. He quickly dropped his pants and got on the sofa between her legs. He bumped my hand out of the way then re-positioned her thong so he could penetrate her.

    Her blow job got a little more rough and sloppy as she became more turned on by my roommate fucking her than giving me a blowjob. I wasn't all that far away from shooting my load so I held her head in place and began to blast semen in her mouth. She kept sucking me throughout my orgasm then continued kissing and sucking on me as I went down but my roommate kept fucking her. It went like this for another couple of minutes until he finally came in her and they both started screaming together.

    We all sat side-by-side on the sofa, me and my roommate with our dicks out while she slowly jerked us back to life, her still dressed in her skirt and thong. I don't know if he got harder faster or what, but she rolled onto his lap and faced him and put his dick up her pussy while she held her thong to the side. They didn't kiss, probably because she had my spunk in her mouth, but he held her first by her hips then pushed up her sweater and bra to play with her tits. They humped like this for about 10 minutes while I slowly stroked my own cock and watched them and the TV. She started moaning louder and going faster and my roommate started grunting as he shot another load in her.

    As soon as he was done filling her pussy, she came over to me and straddled my dick the same way and started grinding on me. I could only last maybe five minutes after jerking myself for how many minutes plus watching them have sex. When I came I came fast in quick squirts up her pussy while she was grinding down on my cock.

    When we were all finished she pulled her bra and sweater into place, pulled her thong back over her pussy and sat back down next to me and put her legs across my roommates lap. We sat for a while like that then she said she better get home. I said she could stay, then no shit she says back "I told my husband I'd be home soon so I better not be late." "Oh fuck!" my roommate goes as I say "You're married? You never said you're married." She laughed and said "You never asked. It doesn't matter, he's a loser anyhow." I asked how she'd sneak in and she tells us "Fuck that, he knows I'm out with you, so he'll just get some used pussy tonight." She giggled and got up to get her phone. She had a little wet stain on the ass of her light brown skirt from leaking our cum out of her thong but she didn't care at all. She got a ride to pick her up and left.

    My roommate and I were in shock...actually, we both still are. She had three loads in her pussy and was probably telling her husband she wanted more when she got home. Now we're talking about asking her back to the apartment again.

    3
    # 48237 - by Roommate / November 28, 2020
    • - Dating Disasters -
    Lesbian Female / 23

    Got Ambushed And Now I'm Pregnant

    In a tough spot. I am currently pregnant. I meet this girl, we spark, we date, we go to her place to get acquainted. In the middle of lovemaking her brother shows up and butts in. I'm not expecting this and I end up under him. Resulting in this pregnancy.

    1
    # 48228 - by Nicki / November 28, 2020
    - Dating Disasters -
    Straight Female / 37

    He Thinks I'm A Swan

    My secret.

    My life was ordinary up until I went through puberty. I was always an ugly duckling, puberty made it worse. Crooked teeth, freckles, ugly nose, no tits, hips and legs, shortsighted. And something worse. Between my legs I grew too. In a word ugly.

    I became self conscious and introverted.

    Life went on, I went to college got a degree in accounting and disappeared into the depths of the finance department working in internal audit. I agreed to go to an after work birthday happy hour for a coworker. I was 35 by the way. A male coworker from operations was there, he had too much to drink and it was dark and I lost my virginity. First kiss, first grope, first fuck.

    He had me change my hair, get contacts, different shoes, dresses, makeup, j*welry, forced to walk straight, invisalign, rhinoplasty, and worse of all have my 'pussy' cleaned up. He is six four, my five ten doesn't matter. He has this thing about buying me nice underwear.

    This man has a thing about having me with him. He likes travel. He likes the theatre. He doesn't like me working. He said that he wants a wife, not a coworker, take it or leave it, the ring. I took it. That was a year ago.

    3
    # 48168 - by Ugly Duckling / November 23, 2020
    • - Dating Disasters -
    Straight Female / 35

    Didn't Live Up To His Standards

    I know this guy who is a trust fund baby. Really rich. He is really rich, but very nice. I met him in college. I now work in the same town he lives in. We are both 35. I got close to him and made the mistake of going to bed with him. And just like that I'm good enough to fuck but not good enough for him.

    1
    # 48064 - by Pam / November 15, 2020
    - Dating Disasters -
    Straight Female / 22

    Being The Woman Sucks

    Lots of talk about women's rights and equality and independence and all that bull shit. I was more or less free when I went to college. But I got knocked up and had to get married and never thought you could get pregnant when your breastfeeding but now I have two kids, both in diapers, cooking, cleaning, waiting on my husband who wishes he never met me.

    He can't breast feed, or cook, or change diapers or bathe the babies. He does work and pays the rent, and plays poker with his work friends, and wants to know why he never has any money. I want to finish college but realistically I don't think I will ever go back, I am pregnant again but I haven't told my husband.

    1
    # 47711 - by Melissa / October 16, 2020
    - Dating Disasters -
    Straight Male / 24

    I Met The Hottest Girl But

    I was 22 at the time and I met this hottie. She was 20 and could have easily been one of the prettiest girls I have ever seen, she had blonde hair and was about 5’4 or 5’5 tall. I met her at a college society and was immediately drawn to her. She had a great personality too. She was cheerful and nice not bitchy like some other girls I know. She was a bit shy which was cute but for some reason also seemed lack confidence despite being so pretty.

    Long story short she already had a boyfriend but the worst part was that her boyfriend was some ugly looking guy who was overweight and in his 50s.

    1
    # 47636 - by College / October 8, 2020
    - Dating Disasters -
    Straight Female / 27

    A Sad Story, A Huge Mistake

    After college, without a job, I returned home until I got my stuff together. My mom got me a job at a daycare. Surprisingly I liked it a lot more than anyone thought. I got attached to a little girl whose mother had died in a drowning on a camping trip. Her father worked at the bank.

    Things went along, I started dating her father, we got married and I had my own baby. All was well, except I knew I had made a huge mistake. I was not in love with him, my feelings for my now stepdaughter had clouded my judgement. My husband was very controlling, he had definite idea of a woman's place, he was not affectionate at all.

    In time I put 2 and 2 together, he had a 'friend', and they rode motorcycles together. Somehow I figured out my husband was gay. He is gay, but realizing that was a bombshell. Sure I got divorced, I have custody of both children. He has child support garnished and I am back with my parents.

    I can't ever know what really happened to his first wife.

    0
    # 47604 - by CT / October 6, 2020
    • - Dating Disasters -
    Straight Male / 55

    Not What I Was Expecting

    So about 5 or 6 years ago I was chatting with a tgirl from craigslist when they used to have sex ads. This girl said she was a petite crossdresser and had some sexy outfits and liked being really nasty and submissive when she was dressed.
    Me and my wife were up for a bit of fun and something out of the ordinary. I was hot to watch her doing a kind of lezzie session with the tgirl and wanted to watch my wife suck some cock too.
    So we go to the motel where this person is staying in town on business and the first turn off is when we get there the room is full of cigarette smoke. The supposed to be petite crossdresser is about my size, 5' 10" but is taller in heels. Has a pretty noticeable 5 o'clock shadow too.
    Pretty decent ass and a little stiff dickie.
    So we go in and he or she goes to lie on the bed and has my wife get on the bed too. They start making out and my wife is OK with it and is tongue kissing and squirming around looking sexy and turned on.
    I would've expected to get excited myself and maybe join them. Figured I would kiss and pet my wife and let the CD suck my dick or something. But I wasn't at all turned on and didn't get a hard on or anything.
    Watched them groping and fingering each other a bit and was trying to rub myself hard, figured maybe I'd just drop a load on them. The CD said she liked being facialed and taking guys loads on her. She liked being used and even wanted to be pissed on.
    Anyway, after maybe an hour or so of them doing some soft core kind of stuff I was still not getting into it or getting hard and finally just figured we should cut our losses and go home for some private sex before it got too late.
    We had traveled like an hour to get there and it felt like a waste of time, but shit happens.
    My wife said she wasn't getting turned on much either but was trying to be a good sport and see if things would get better. She'd have done whatever I asked her to do or whatever the CD asked her to do, but she was just going through the motions too.
    So in the end we were kind of frustrated and were on the way home when we spotted a couple of sexy looking girls hanging out on a corner. They looked like hookers and I went around the block to check them out again.
    Confirmed that they were whores and stopped to talk to them for a minute while my wife went to get some stuff at the convenience store on the corner.
    Made a deal with the prettiest whore to sit in the back seat and make out with my wife while I watched and this time I got hard right away.
    My wife was sucking the whores tits and she was fingering my wife and both of them were moaning and the car smelled like pussy.
    I had my dick out and was stroking when the two girls started to blow me together.
    That was real hot to have my wife suck my cock and a whore lick my balls.
    Wife was turned on to be doing this shit on a quiet city street around the corner from where we picked up the tart. There was probably other guys parked on the block getting laid or getting blowjobs from other whores too.

    0
    # 47595 - by TedT / October 5, 2020
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