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.

Am I Dumb Or...?

I was at the local bar the other day when a guy approached me. Got to know each other over a few drinks, he was younger than me but looked great and had a great personality. Long story short, I invited him to my place for the night because I've been a bit lonely.

I give him a little head, he eats me out a little, everything's going great until he's about to push in. I ask if he has a condom and he says no, so I push him back a little and say maybe we shouldn't. He tells me not to worry, he's figured out a way to hold his cum in so that there's nothing to worry about. I was surprised because no other guy has told me that before. It was just something about how confident he was that made me believe him.

So yeah, we had awesome sex, I'll admit that. It had been awhile since a guy could make me cum on his cock. I finished him off with my mouth and let him give me a facial, but it was kind of disappointing. Oh well, I had my fun... or so I thought.

He packs up and leaves while I lay relaxed in bed, said something about going to work. I get up to use the bathroom, that's when I feel the cum dripping down my leg. Then I realize that I never got his number or anything. Am I dumb?? I felt so dumb after that... maybe I'll never hook up ever again.

  • Rough Date

    This short and sweet,

    I'm 26 and love sucking cock. I like some porn stuff kinda and I'm on Tinder. I don't always need to get off so i like to please the men a lot. Met this black guy on Tinder agreed to hook up he just wanted a blowjob and i obviously wanted a cock in my mouth. While sucking his dick which was large to say the least and before he was about to cum he asked if he could come on my face i said no he said ok how about a throatpie i said what is that he said i just cum in your mouth kinda i said sure. He then grabbed head head forcing his cock down my throat like balls deep then blowing his load in my throat making me gag, choke and and shoot cum out my nose. never done that. kinda gross but i liked it at the same time.

    An Old Suitor Came To Town, Now He's More Than A Suitor

    I am not a prude but sex is personal, having a stranger sticking his penis in you is pretty personal. I've known him for a long time, so not a stranger. Older by 10 years, used to flirt with me when I was in high school. He was back in town for his mother's funeral (not COVID). he asked me out, so we went out for pizza and a beer. He looked at me and told me he loved me back when I was in high school and seeing me again rekindled his feelings fir me.

    He has a good job, unmarried, owns his place, grew up two houses down, basically the proverbial good catch. I lost my head, fell for his line, he took me to his mother's house to show me what was there and to see if I could help him sell the contents and list and sell the house, I'm a realtor now. In the bedroom he pushed me gently and I sat on his mother's bed. Then he told me he had been conceived on that bed and wouldn't it be great if I conceived his son on that bed.

    Talk about a head spinner, his hand on my forehead he pushed me over on my back. I couldn't even stop his hands as he undressed me, and then undressed himself and asked if I was ready to conceive. No words came out of my mouth, his penis penetrated and then he ejaculated asking me if I was ready to be a Mom.

  • Lost My Head At The Bar On Friday Night

    Sure it's inappropriate, but who cares. Joe Not His Name asked me to let him see my panties. Joe is in a position of authority and in my chain of supervisors. It wasn't at work, it was at a bar after hours and drinks were involved. I had a dress on and I pulled my dress up far enough for him to see my panties, laughed and he smiled at me and told me he wanted to go home with my panties in his pocket.

    We were in a booth and I did slip my panties off under the table and he did put the panties in his pocket, but not begore rubbing the back of his hand along my bush. Maybe it was his arm around my shoulder, or his hand on my breast, or sitting commando, but his kiss was answered with a kiss and pressing his hand against my breast. My head said no, stop now, but that's not what my between the legs feelings said, all I could hear was 'more'.

    We went outside, to the alley behind the bar, holding on to the street sign, and he lifted my dress and struck home. It was all bad, from a work point of view, he crossed the line, I crossed the line, but that fuck was worth it. Afterwards I sat quietly under his arm in the booth in the bar, my girl parts still wet and sticky so I kept my legs crossed thinking of all the dumb things I've done. Fucking the big boss behind the bar has to be the dumbest of them all.

    Fake ID

    I've been dating this guy who is like 25 for three months now. He thinks I'm 21 because I have a fake ID that I used to get into the club we met at. I've been able to keep up the facade that I'm 21 but it's so stressful. He wants to take me on a vacation but there's no way my parents will let me go away for a week.
    I don't know what to do. I am totally sure he will be pissed when he finds out I'm only 16. I really like him a lot and he's really good at sex. But I know I need to tell him the truth. I'm just too scared to.

  • Knocked Off My Feet, In Love At First Sight

    I finished my Cardiology residency June of 2020 and joined a practice with a large client base. I was assigned a patient, a 36 year old woman with congenital heart issue. She was there for her annual checkup. When I walked into the examining room I lost a breath. Her blue eyes went through me, her handshake was too long, her smile transfixed me. In my life experience no one had made my heart miss a beat.

    I went over her history, her current condition and health status. I examined her and had her lay down. While I listened to her heart I had to unbutton her shirt and fit the stethoscope under her bra. She looked into my eyes, and asked 'may I?' and put her hand under my breast. I lost bladder control and wet my pants. Her hand on my breast caused my voice to break telling her it was inappropriate, but I did not remove her hand.

    I composed myself and stood back, telling her she couldn't be my patient and I had to excuse myself. She sat up and told me she wanted me to be her doctor, not somebody who didn't care. I told her she was fine, to come back in six months and I would find another doctor for her case. And I went to change my pants.

    That evening I got a phone message asking me to meet her for lunch the next day. I decided to go, to end this completely. Her eyes took KY resolve away, she told me she was married, but he was a man. That she wanted me to meet him. She wanted a start over, she knew more than ever I was the one she had been looking for. I had no choice, no backbone, I agreed to meet her on Saturday, her and her husband. She walked me back to the clinic kissing me on the lips.

    Saturday. Three days after I first set eyes on her. Her husband is a big man, 50 something, very manly, very firm handshake, took over the conversation, interrogated me, told me his wife was not to be hurt, questioned my intentions, asked if I walked on both sides of the street or stayed in my lane. I couldn't answer, except to shake my head. He gave us permission to get to know each other.

    Sleeping with her was private, being taken by him was three's company. I rushed at the end of the day to see her. I had to admit to myself I had never had a crush like this, never made love like this, never before had I let a man have me, but it made her happy. If only I could wake up with her every day.

    I don't now, or since I learned of my propensity, deny I am a lesbian. She is a lesbian. My heart, grain, feelings, emotions right now are overwhelmed. I can't explain allowing her husband to have me, to play three's company with them. I thought getting my medical degree was the hardest test in my life, it's not. Figuring out this relationship mix is.

    Taboo Sex And I'm Not Sure What I Should Do

    I met this guy at a party. After a couple of bad dates we had a decent date, which ended with me sleeping with him. His sister, who is still in college came to spend the weekend with him before school starts. The three of us went out, and later back to his apartment. After a sex session I fell asleep only to wake up to him fucking his sister. She was all into it, obvious as hell. I got out of the bed and just stood and watched (which I'm ashamed of) while he pulled her fully under him and finished fucking her.

    Not new, she wasn't at all apologetic or bothered about it. She was his first and visa versa. It's their thing. She says it isn't romantic but she has no desire or intention to find a man. I am on the fence, part of me says who cares, they are both over 21, but part of me says what the fuck. I'm fluid enough but no threeway sex with her is going to happen.

    Why Do Some Women Fuck Easily

    Why do some women let guys get between their legs so easily?
    Before I got married, some girls and women would only let me touch their tits and no more.
    But my wife to be let me fuck her and and spunk her on the second date.
    Later our marriage she admitted that she had been fucked a lot before me, most of them were one night stands.
    Why did she fuck so quickly when others wouldn’t ?

    Fucked For A Ride Home

    Talking to my wife of a few years, she opened up about when she was in her early twenties before she met me.
    She agreed to go to a college dance with a guy who was boarding there.
    He was a few years younger than her.
    During the dance they went back to his room where he tried it on.
    But she said no... but he said that if she wanted a lift home she ... should let him have sex!
    I would have thought that she would have said get stuffed... but she just lay there on his bed while he pushed her dress up, pulled her panties and tights off.. then dropped his jeans and underpants.. rolled on a condom and fucked her!!
    When he had had her...they got dressed and went back to the dance as if nothing had happened although his mates did smile a bit??
    He took her home... and wanted to see her again but she said no!
    She said she felt that she had got the upper hand because he didn’t see her naked!
    But I said he had got what he wanted anyway???
    She didn’t agree because he hadn’t seen her naked!!
    but surely she only did what most women in her situation would do ?
    Do you agree?

  • I'm Not An Ice Queen, I Wanted Him To Earn It

    This is dumb but here goes. My roommate, we are college friends, claims she is a lesbian. She had a thing with this other woman for a long while. It burned out and now she's single. I have a coworker that is hot for me. Too hot. I kept him at a distance. He showed up at a party my roommate and I went to, mutual friends. He pressed me until I gave in to a kiss and feel.

    He drove us back to our apartment. He pushed his way in and wanted a drink. He went for me, I pushed back. He turned to my roommate and just like that he had her on her back giving her dick. Afterwards, he stared at me and told me I lost out.

    My roommate, the lesbian, sleeps with him. He makes a point of shoving it in my face. The door to her bedroom is never closed so I hear everything, every groan, every dirty word, every sigh. I'm going crazy, he won't touch me because I was a slab of ice to him. He just rubs it in, giving her all of his attention.

    Yeah, I'm jealous. I was going to let him in, but he had to earn it. I'm not an ice queen, if he gave me the chance I'll prove it.