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.

I Did It For The Lols

I think it’s hilarious when men say, “is this the biggest cock you’ve seen?” Or something dumb like that. That’s a big ol’no buddy 10-4?
They get all flustered you think it’s small. No buddy no I don’t think it’s small just because it ain’t the biggest I’ve seen. I’m on date with you for you not your dick. Though I’m hoping to ride it soon no that it’s made an appearance.
If I wanted just big I’d go get a giant toy or go back to the farm where there are stallions with cocks the size of my leg. One dude was so turned on by that he begged to hear more while he ate me put. What’s a girl to do when a skilled gentleman is literally begging to tongue fuck my pink box?!

  • Girlfriend's Mom

    I've been dating my current girlfriend for about 2 years now. We'd been friends since highschool started but only started dating about a couple of months before school ended.

    Even after being together for 6 months she wouldn't let me fuck her. We do oral both ways and she's really good at giving head. I love to eat her pussy too and wish I could fuck her but she's determined to be a virgin on her wedding night. She won't let me finger her even, and there's nothing going in her butt so forget anal.

    A little over a year ago I was really getting frustrated. I'm not ready to get married and she agrees that we both need to wait until after college. I was telling her that maybe we should see other people for a while just to be sure about us. (I really just wanted to get laid.) She started crying as if the world was coming to an end. I told her it was just a bad idea and went home.
    I got a text from her mom the next day saying we need to talk... In private!

    As you can imagine I was pretty nervous about having this talk with her mom. Her mom isn't bad looking for a woman in her 40s. She's kind of short, but thin with a nice butt and small tits. Blonde hair, kinda short cut, but nice.

    Anyhow I go over there and my girlfriend Chrissy isn't home, and I sit with her mom in the kitchen. She says Chrissy was crying all night so she had to dig it out of her what was bothering her. So Chrissy said you want to see other girls. Why? I tried to use the same line that I thought we both should be sure that we were the one for each other blah blah blah. She said right. Now tell me the truth. Isn't it because Chrissy won't have sex with you? I was kind of shocked and almost said well we do oral but then thought better of it. I said well, to be honest yes. It's hard not to make love to the girl you love after all, and I'm not sure I can take three more years of this. But I do love your daughter.
    She goes on about how I could lose her, or what if I catch something or knock someone up? I said I guess you're right. But I still don't know if I can last until our wedding night if we make it that far. The next thing out of her mouth floored me. Well then fuck me until then.

    Now I know most of you would think that I said hell yes, let's go! But I was intimidated or just unsure of myself at that time as I had little experience with sex. I had fucked a couple of girls in my life to that point. But looking back, I wasn't much good at it.

    I could hardly look at her when I said are you kidding me? You must be testing me or something. She said look, I understand a young man like you had needs. I also like you and hope you and my daughter end up married one day. I would rather have some control over what you do sexually before you start having sex with Chrissy do you don't bring anything nasty home to her, or get aids and ruin your life. Besides I'm sure I can teach you how to be a good lover for her.
    I said that would be a good idea I guess and she noticed the bulge in my pants and says, no time like the present to get started and took her top and bra off. She has really nice tits. Big pink nipples that looked great on her small round tits. I sucked on them right away and she seemed to like it.

    She helped me learn how to eat pussy better than I was. How to tease and get her to orgasm easily and powerfully. She taught me how to make her squirt which I fucking love. Then she taught me how to fuck for more than two minutes. It took a lot of practice. I loved practicing with her. After a couple of months I was pretty good at it all. She likes it all, oral, anal, vaginal. We even do DP with her using a dildo in her pussy while I pound her ass.

    Now as I got better at oral sex, Chrissy noticed my technique changed while eating her out. She asked me how come I do it different now? I said I read up on it and other things because I thought if I did it better she might give in and give up the pussy lol. She bought it. Whew!

    The thing is, I'm totally into sex with her mom. We fuck so much, it's addicting. We have had weekends away together even. I usually have a few guys weekends every year so Chrissy doesn't suspect anything. She just thinks it's a shame when her mom goes to visit her grandparents at the same time when we could have alone time. Lol

    I'm not sure how this will all end. Two more years until graduation, so I'm going to enjoy this while it lasts. I keep pushing Chrissy once in a while for that sweet pussy, she still hasn't given it up. But she says more and more that maybe we can do it one day since she's sure we will be getting married. Maybe for our anniversary in January.
    If course I say, are you sure babe? I know I love you and I'm sure we will end up married anyhow.

    I ask myself if after I start fucking Chrissy will I have to stop fucking her mom? I guess I'll cross that bridge when I come to it. I'll be giving her mom a good pounding in about an hour from now when she stops by. Should I ask her how this will all unfold when Chrissy and I start having sex? Or should I just ride it out?

    Her Dad

    I need advice.

    I’ve been dating this beautiful bombshell brunette chick I met at school for almost a year now. Her name is Ashley and she’s around 5’4 fair skin, blue eyes, beautiful pink lips, gorgeous huge pair of tits that bounce everytime she walks, sexy legs and thicc jiggly ass.

    I met her after a wrestling tournament I participated in a while back and we hit it off pretty well after one of her friends mentioned she had a thing for wrestlers. Ashley lives alone with her single Dad who is this very fit and young looking 6 feet jiu jitsu coach. He is always around when Ashley is not out with her friends or I.

    Ashley is my first love, but when we met she briefly mentioned one day that she had already been with other guys. I have never dated anyone before but have also had my fair share of experience with girls and told her I was willing to make it work.

    Well one day at a beach party hosted by her friends in a rental, one girl told me they thought that Ashley might be seeing someone else. My heart sank but I did not want to wait days to find out. When everyone was drinking and playing games I quietly asked Ashley if we could talk privately outside and I confronted her. She broke down and confessed that she was not seeing another boy but that she has a deep sexual relationship with her father.

    I was completely broken and confused and had to wait a little to process and for her to calm down. She told me that her and her father had been having sex for a few years now and that it started one day when he came home drunk on the couch and fell asleep. She said she tried waking him to ask something but noticed he he had a huge cock poking through his shorts so the whole night she slept on his lap and couldn’t help but play with his cock.

    The day after her Dad had a talk with her and set up an appointment for her to be on the pill but Ashley couldn’t keep her mind off of how big her father was compared to the boys she had been with. Their relationship progressed and now she sleeps with her father in the same bed and makes love to her every week.

    She mentioned she tried keeping this a secret because she doesn’t want to lose her father but knows that no one would understand. I asked her if she truly loves me and she also said yes. She loves her father but she can’t have a social relationship with him like with me.

    Anyways, I’m confused, kinda turned on, conflicted, a little weirded out and now I can’t stop thinking of her fathers deep stroking and rough fucking my Ashley. Her and I have a lot of sex but now it seems like it may have been nothing special if she’s getting her back blown out by her father every week. Should I keep their secret or should I break things up?

  • Bigger Isn't Best

    So I've not had a a proper relationship in years I've had partners but eventually they leave me because of our sex lives being poor. I had one long term girlfriend but eventually she broke it off.
    I always thought having a big dick would be awesome, turns out porn lies lol. Soft my dick is 11inches 12 when hard and is quite thick.
    Whenever it comes to sex women seem excited at first but quickly change their minds complaining its to big. I've never managed to get deep into a woman which makes it hard to enjoy and blowjobs are never finished.
    Am I just not finding the right women or is this gonna keep happening

    Embarrassed The Way My Boyfriend Wants Me To Please Him

    Quite frankly it was embarrassing being fucked in the ass. I wasn't at all prepared for it and I shit when he pulled out. He made me clean up the bed, and put the sheets and mattress cover in the wash and hang around until the sheets were dry and make the bed. He let me put on a shirt but no pants or panties, he wanted my bush on display, My butt, bottom, started to hurt and he told me he would examine me, embarrassment number two having a me bend over like that. He said I had a small tear and he put some Neosporin on it and I had to apply it again if I went to the bathroom.

    I know none of this sounds sexy. It isn't. He wanted it 'all', my throat, my vagina and my ass. My throat didn't work, I gagged, of course my vagina was fine and he finished inside of me, He wants all his sperm inside of me, he won't finish outside of me. And my ass, well I was complaining and he said ok missy and turned me over and fucked me right then and then everything became a mess and I had to clean it all up (it's a lot worse than you think).

    I hate that he likes looking at my bush and I have to walk around without my pants. And I don't dare bend over or get up without being very careful, it's embarrassing enough without having him look up my vagina every time I stand up.

    That's all really. It's just that he is so intrigued by my pussy. He didn't have sisters or even girl cousins. I don't go asking him to show me his dick all the time. I have three brothers and dicks are not a mystery to me. Sure I like his dick, in a non sexual way, it's nice. But I'm not hung up on it like he is with my pussy.

  • Pregnant At 16

    We were new to town and hadn't made any friends. It was prom week and everyone was talking about who they were going to prom with. The son of one of my father's coworkers was graduating and he was told to take me to the prom. I got a dress and shoes and went to the hair salon. He picked me up, he had to talk with my Dad. The prom was at a hotel in town and my father told me not to go to any rooms.

    Halfway through the prom he told me and some friends were thinking of going to the lake. Everyone was a senior except for me. I said I would go I did not want to go home. The drive was 45 minutes, I rode with him. On the way I started to think about losing my virginity that night. At least it was going to be with a senior and not some little kid. I thought about my period, at least I wasn't on my period. I would tell him to pull out. Problem solved.

    At the lake there was lots of alcohol and other things. Couples were making out and he asked me if I wanted to. We made out, he felt me up pretty good. I could see out of the corner if my eye a couple having sex. That was going to be me. My pants were off, I pushed him back and told him he had to pull out. Sure, he told me he would. I took off my panties and laid down on the carpet with another girl by my side. I spread my legs, saw his hard dick, and closed my eyes.

    He didn't pull out. S8rry, he forgot. I got scared, went to the bathroom and vomited. Another girl asked what happened, I told her, she told me she had a morning after medication at home and she would give it to me. Except she left with her date and I stayed because my date was drunk. I woke up with another girl, she asked who I was. I never saw the girl with morning after medication. I got pregnant at 16.

    I never got an abortion, he told me he would marry me when he finished college. He never did. I changed schools, to a home school program till after the baby was born. I never returned to that high school, none of the girls at that party ever looked me up. Not until I was out of college. Then the girl with the morning after meds called me. Sorry.

    My daughter is 9, I teach second grade. I gained a lot of weight. I have a guy, not a boyfriend, a guy who has sex with me. He works downtown and no one knows about him. It's sex. I met him at a party. One day I'll meet a guy to get married.

    Still Technically A Virgin

    I am sick and tired of hearing about how women like big dicks. I have a very big dick. Bigger than even most of the porn stars I've seen. I am not bragging. I am complaining. I still have never fucked a woman. Not from lack of effort but every time we start getting down to business, once they see my dick, it's over. No way will that fit, or oh my God! That's way too big. I have eaten their pussy for long enough for them to cum multiple times and even then, it's usually, no way Jose'. One time a girl I dated tried with her on top but barely got past the head and said it hurt too much.

    I did let this guy blow me once in college but I was drunk out of my head and hardly want to go there again.

    I really don't know what to do. Is there somewhere you can go to find women with really loose pussies? Someone who can not only take, but enjoy a really big dick?

    Mine is just over 10" long and a bit fatter than a half liter soda bottle.

    I'm getting desperate. I'm afraid to date women my age as I'm tired of rejection.

    Catching My Man

    The difference with men and women is easy. Men have sex and walk away. Women have sex and they are hooked on him. Especially if she is young and he's older and mature. I was 19, he was 29. My life experience was limited to living at home, his life experience was Army Ranger, officer, stationed overseas, combat, Master's degree in Engineering. And heavily experienced in matters of the flesh. Woman flesh.

    How many women? I didn't care. How many men for me? Zero. All I know is that afterwards I was a woman. He didn't think so, but I knew so. I did what women in love have to do, I haunted him, when he looked up I intended to be there. As far as I was concerned no other woman would catch his eye again. Of course, in my mind. He had other women, I imagine some were like me, he was their first and in love, and others did those things for a living.

    I got up the nerve and went to him and asked him why he didn't call. It was just sex he said. Not to me, I said. A woman, I reminded him, doesn't play around. He looked at me, a girl would say something like that. I had a lot more work to do. I'll cut to the chase, it took me all of my sophomore, my junior, and senior years. By the time he saw the woman in me, I was an experienced woman. How many men for me? One. I won't say how many women for him, it's not becoming to be counting other women.

    I'm married, my idea not his, but perseverance has it's charm. I don't ask him where he's been, none of my business he says. I don't ask but I got him guilted into telling me. Ruined it for him. Sorry, a woman doesn't kiss and tell, and it turns out that him kissing and telling started to sound bad to him, like a kid bragging. So I can only conclude, he's down to one woman. And that's me. He's not bragging any more.

    I'm not bragging, it's true.

    I Was Straight All Along

    My father is a police officer. Very dominant. When I was little he was very protective and loving. When I went through puberty he was controlling, dominant and abusive. It was so bad my mother sent me to live with her sister. A sweet lesbian with a dominant lawyer partner Christine.

    Chris always 'liked; me, I am her favorite. She cut my hair short, bought me boyish clothes, allowed only very subtle j*welry, talked about me meeting the right girl. She also shaved and waxed my privates, because when it came to that a nice compact smooth 'kitty' was what girls liked when it came to kissing. She also told me that if a girl didn't pay attention to her snatch not to go down on her.

    All during my teen years I was around lesbians, I was introduced to nice girls, only allowed to date girls, I had various sexual partners which Chris debriefed me on giving me best pointers on how to make a girl cum. I was sent to Chris' alma matter, a small school with a reputation for lesbians. I can't say I met an out straight girl there. When I went home I was treated to spa day, full Brazilian, new panties, always new panties. Chris was deeply interested in the girl I brought home. Be more assertive, let her know you will take her hand.

    When I went to work after college, before law school, I met a man, mid thirties, assertive, masculine, strong, and he tore through me like a hot knife through butter. I babbled, became a five year old, wore a dress, and the beautiful earrings he gave me. I went from tomboy to fem.

    Chris was sick about him. She was downright ugly to him. He wasn't phased at all which pissed her off. I 'blossomed' with him and fell hard for him, my first unabashed love interest.

    I have close girlfriends, I grew up around lesbians and can navigate the 'parties'. I don't ask Frank to join me, he is turned off by so much estrogen. I have since going straight but remain intimate with one girl. Like me she gets visited by a boyfriend. We escape, and enjoy, but when he whistles we run home.

  • Just Another Girl

    People don't realize that it's not easy to find a partner when you're pretty. They also make assumptions like I'm dumb because I happen to be a pretty blonde. Even after finishing my computer science degree there are people out there who make excuses like I got a higher mark just because I'm pretty.

    I'm just another human and I can do the same job as you so why do I get treated so differently. I want to he treated the same as everybody else. I don't like it when men open doors, stand up to give me a seat, or help me up when I trip, but not do the same for another person just because I'm pretty and they are not. I want to find someone who can treat me just like another person, and like and accept me for who I am and not for my looks.

    I'm not outgoing or an extrovert like people think. I like wearing cute dresses and slightly revealing clothes, but that doesn't mean I'm an extrovert. I actually wear it for myself. I'm actually quite shy and introverted. It's a bit hypocritical of me to say this but, sometimes I wish some of the nice and introverted guys would have the confidence to come up and talk to me and get to know me without taking my looks into account.