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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 / 75+

Today’s Female’s Are Very Fortunate

In 1957 I was a junior in high school. I didn’t date steady preferring to play the field. I had made the cheerleading squad which made a girl even more popular with the sports guys.

Casual sex wasn’t as excepted back then as it has become today due to the lack of means to prevent getting pregnant. If you did mess around it was with a rubber (what a condom was called back then) or the guy pulled out before cumming in you.

I had managed to avoid having sex mainly due to the fear of getting pregnant but also because once you did guys didn’t keep it a secret they had gotten it.

During basketball season I started seeing one of the players on a more regular basis so we began some heavy making out but still I wouldn’t go all the way.

One night we were parked making out then I got very aroused when he was fingering me.
When he said he had a rubber I gave in losing my virginity.

It was very exciting and pleasurable until the rubber broke just as he came. There was nothing you could do in those days but wait and pray for your period to come.

As my luck would be I got pregnant my very first time. That was a very embarrassing thing getting knocked up back then with no choice but to have the baby.

II had a beautiful baby boy but the guy who got me pregnant never had anything to do with us. His parents paid my medical expenses but I never got any support of any kind from him.

1
# 76465 - by Nancy / January 29, 2025
    • - Dating Disasters -
    Straight Female / 42

    Thought It Was Going To Be My First Time.

    I've been reading these dating disaster and kids stories. Took me back when I was 15. I had a few giggles and memories. Dad took mom out to celebrate their wedding anniversary. I've been seeing this guy from school. He was a year older. I thought about it gave him a call and invited him over. I dressed to be fucked. Gym shorts no underwear a school gym shirt, Wore one of those fancy front hooked bras for easy removal which I coped from my mom. We had an entertainment room in the basement. We started out there. On a couch and watching a movie. We started making out. About ten minutes later I told him there was a bedroom down the hallway. I smiled at him. And I led the way. We laid down and resumed the fourplay. Off went my shirt and bra. We're kissing and he's rubbing on both titties. Finally, he got brave and wanted to remove my gym shorts. I raised my lower body for easier removal. Felt his hand go between my legs. He found my opening and started rubbing. I got wet and there goes a finger inside and my nipples got hard. I even took time to play with both titties. I couldn't stand it anymore I looked up and said fuck me. I watched him stood up and watched him undress. I viewed my first guy hard on. I raised my legs and reached up for him. He took position between my fully spread legs. I then felt his dick at the entrance of my willing body. Then I heard a door open from upstairs. My mom is yelling anyone at home. we were scrambling to get dressed and get him out the basement door.

    2
    # 76456 - by Charlene / January 29, 2025
    - Dating Disasters -
    Straight Female / 21

    On The Date

    At a party with my bf I needed to go out for some air. All of a sudden a black guy came from nowhere, pushed me on to all fours, whipped down my knickers and bred me, It was as quick as that maybe a minute and a half. I felt him cum inside me before pulling out and then he was gone. I haven't told him but time is ticking you see I'm pregnant and life is sacred. I don't know what to do we're both white.

    5
    # 76295 - by Susan / January 23, 2025
    • - Dating Disasters -
    Straight Female / 23

    Met A Guy From Online In Person For A Date

    I had met Brian online after a pretty bad breakup. I'd been in a relationship with a guy I thought I'd marry and I was so upset when he broke up with me. I was frustrated snd angry and had agreeed to go out with the first guy who asked even though I didn't know him. We met in person at a bar and he bought me a few drinks, he wasn't really my type but I was so confused about losing my ex I just agreed when he asked if I wanted to go back to his apartment. He told me he had roommates and when we arrived there were four guys playing video games. I remember sitting with Brian and him fixing me another drink and then encouraging me to take a few shots. I am petite and didn't usually drink like that and I got really wasted. Brian got me to take another shot and he asked if I was ok and put his arms around me and pulling me closer. He was talking in my ear telling me I was getting him excited and how glad he was we met. His hands were moving to my chest and he started grabbing my small breast through my top right there in front of all his friends. He started to squeeze and was telling me he didn't usually go for petite but that I was turning him on. I'd never ever been touched like that in front of anyone and it felt so offensive and personal but I just froze up and could see the other guys watching. He starts kissing my neck and I got so nervous and wasn't sure about any of it but he was using both hands and before I could react his hands were under my shirt and directly on my small bra. I felt my heart racing and it felt so dirty and wrong and was nothing I'd ever done but he was telling me I was ok and to just relax and was trying to pull my top up and off of me. It just happened so fast and I was so nervous and scared but I just froze up. My shirt came off and Brian started to reach behind me to unfasten my bra and one of his friends got up and walked over to us. I could feel my face burning when he took my bra off, I am barely a B cup and wasn't confident or used to being exposed like that at all. My nipples are tiny and pink but so so sensitive and he had his mouth on one, sucking it then biting it. It felt so dirty and wrong and just sinful but I didn't stop him or say anything. Brian had his hand on my thigh then up under my skirt, rubbing the front of my panties. He reached under my panties and started to touch my clit and I grabbed his hand. He was asking if I was a little tease and that I shouldn't be like that. He asked if I needed him to kiss me, did I want him to lie to me and say I was beautiful and special. He started to finger me and I let him, he was telling me I knew what I was and why I was there. That I wasn't even that pretty and should be happy they even wanted me. He started to finger me and was telling me how wet I was, asking if I wanted him to stop or was I ok. I've never felt as dirty as when I said ok and arched my hips up to let him remove my panties in front of his friends. It didn't even seem like it was me but Brian was pulling his jeans down and getting in the floor in front of me. He put my legs up over his shoulders and I stared down watching him rub his dick against me then push it inside my vagina. I was so scared and just so confused, I'd only been with boys who I'd dated and never ever done anything sexual with people watching but I was on some dirty couch with my legs open and some guy I'd just met fucking me in front of his friends. Guys I'd dated had treated me like I was delicate and fragile and like some princess but this was so different. He was starting to just pound me and I could hear him saying things, insulting me so everyone could hear him. Nobody had ever done anything but flatter or compliment me so when I heard him call me a whore it was so erotic. Brian was moving his hips and fucking me, starting to move faster and was cursing at me. I remember one of his friends walking over to me and put his cock in my face like it was expected or normal or I don't know. He was telling me to just do it, to open my mouth and I don't know why but I did. I'd seen it in porn but never imagined I'd be doing it, getting fucked by one guy and have another in my mouth like some bitch in heat. It's so personal but I started sucking him like he was my ex, getting into it while that strange cock was up inside me with my legs up. I could hear him groan right before he started to cum, shocking me that he was doing it deep inside me. I couldn't even catch my breath before the guy I'd been sucking pushed me on my back and got on top of me, I was getting fucked by a second guy with Brian's cum still leaking out. It's embarrassing but I started to orgasm with the second guy and was calling out when he was calling me filthy names. They ended up taking turns with me and getting so rough and nasty. It wasn't romantic or anything like I ever experienced, it had some consequences after but it was the dirtiest thing I've ever gotten into before

    3
    # 76189 - by Michelle / January 19, 2025
    - Dating Disasters -
    Straight Female / 18

    Very Much An Accident

    I’ve been dating my boyfriend since we were sophomores and we’re now seniors in high school.
    We make out a lot but have never gone all the way although he has gotten close several times.
    A few weeks ago we were messing around in my room. He took my panties off and was rubbing his penis on my stomach when he came. It ran down between my legs so I ran to the bathroom and cleaned it up as quick as I could.
    I didn’t think any more about it because I was sure none of it got close to my clit.
    I must have been wrong because when my period was supposed to come it didn’t. I thought maybe I was just late but after a week I took a pregnancy test and I was pregnant
    It was very much an accident since we didn’t have intercourse. We haven’t told anyone still trying to decide what we want to do.

    4
    # 76158 - by Brenda / January 18, 2025
    • - Dating Disasters -
    Straight Female / 18

    First Time Went Very Wrong

    I started my senior year of high school in late August. I’ve never really gone steady with a guy since I play sports and cheer.
    For homecoming the middle of October I invited my brother’s college roommate for my date.
    After homecoming we parked at a local hangout used by kids from school doing some light making out.
    I had let guys play with my little tits but nothing else so when he ran his hand down my prom dress top I didn’t say anything but for some reason, which I now know why, it quickly got me excited.
    When I felt his hand going up my dress I told him I couldn’t do anything because I was a virgin he didn’t stop running his hand in my panties.
    It didn’t take long for him to have me totally confused as to what I wanted to do but when he started working my dress up I just raised up so he could then spread my legs for him.
    He got his penis out telling me he didn’t have a condom so I pushed him back hesitantly but he promised not to cum in me pulling my panties to the side entering me.
    The feeling was amazing so I got in a slow rhythm with him reminding him several times to be sure to pull out before he did anything.
    All of a sudden he slowed down so I yelled for him to pull out but he said it was too late at the same time my body reacted to it with an orgasm.
    Once he had finished he pulled out putting my panties back apologizing for not stopping in time. Then I could feel it running out of me which caused me lots of concern.
    When I got home I realized how much he had done because my panties were a mess.
    A couple of weeks later I realized why I had gotten so aroused when we were making out when I missed my period. A pregnancy test confirmed he had gotten me pregnant.
    After much consideration I decided to have the baby. I’m 13 weeks along with it due around July 14th,

    4
    # 75952 - by Cassie / January 10, 2025
    - Dating Disasters -
    Straight Male / 26

    First GF And Small Dick

    A few years ago I started dating a young girl. I was her first boyfriend. She was a truly virgin. I always had a huge desire for her, but there was a problem: my cock is small. Since we had to see each other in secret most of the time, we didn't have a place to explore our relationship and get to the penetration. In fact, I was always afraid of getting to penetration because of my small dick. I always played with her pussy but I didn't let her touch my dick out of embarrassment.

    She was very naughty, we played in public places like emergency stairs and she always got very wet. I even asked her what her desires were and she said she felt like having sex with two people one day. We dated for about 3 years and, believe it or not, we never got to penetration. I took advantage of her body during oral sex but I only let her touch my dick a few times, most close to the end of our relation. Not even a blowjob. We tried penetration once but because I was nervous about getting caught I couldn't continue.

    At the time she was already a hottie, everyone wanted her. Skinny, white, dark hair, delicious breasts, a angel face but deep down a real slut. We broke up and I couldn't fuck her. My biggest regret. If you could see how wet she got just from kissing...
    To this day I have a huge desire for her and after I found out she started dating again I started masturbating myself imagining her having a real big dick fucking her, doing everything she couldn't do in the 3 years we were together, ridiculing the fact that she dated a guy for all that time without even having fucked her. Everytime I see a photo of her in a party or with some guy I already start to jerk a lot. How I wish to get her again only to tell her I need to see she fucking big guys.

    4
    # 75950 - by Tributeb20 / January 10, 2025
    - Dating Disasters -
    Straight Female / 18

    New Year’s Eve Will Always Be A Terrible Memory

    I and one of my best friends were invited to a New Year’s Eve party at another friends home. He has just started college so some of his new friends were there too. His parents were out of town so there were no adults.

    As the evening went along one of the guys from his school and I kinda started hanging together.

    I excused myself to go to the bathroom which was on the second floor. When I came out he was waiting pulling me down the hall into a bedroom.

    I told him I wasn’t interested in anymore than casual kissing but he pushed me down on the bed. At first he just kissed me but then unbuttoned my blouse playing my boobs.

    I had gone that far before but when he started his hand up my skirt I told him I didn’t want to go any further but he went ahead.

    He rolled over on top of me and I realized he was getting his penis out with his other hand so I told him we needed to stop.

    When I felt him pulling my panties to the side I asked him to please stop that I was a virgin.
    I guess that just just encouraged him more so he shoved his penis in me.

    Being too late to save my virginity I asked him to at least put a condom on so I couldn’t get pregnant but again he didn’t stop.

    I had no choice but to try relaxing as he had his way then asking him why he had done that to me as I could tell he was coming inside me.

    When he was finished I ran back to the bathroom cleaning up then going back to the party..

    I found my friend telling her we needed to go. She could tell I was upset so we left. Once we were in the car I told her what had happened so she took me home.

    I was so embarrassed I had let it happen that I just didn’t do anything because my period was due in six days. Fortunately it came right on time on this past Monday.

    4
    # 75898 - by Amy / January 8, 2025
    - Dating Disasters -
    Straight Female / 42

    At This Point, All I Can Do Is Pray

    I’m 42 and divorced after being married for 20 years. My divorce was final last March but I didn’t start dating again until August. Until October I had met no one I really found that interesting.

    Through a mutual friend I met a younger guy (27) who had lots of common interests so we had several dates.

    Early December he invited me to take a ski trip the week of New Years so I decided to accept the invitation.

    I have not been on birth control for over 15 years since my Ex had a vasectomy after our last child. Even though we had not had any discussions about sex and expecting we would probably be intimate I bought condoms in case he didn’t since I didn’t have time to get on the pill

    We arrived at the ski lodge Monday before New Year’s and as expected we were intimate that evening with me letting him know I wasn’t on birth control needing him to use protection.

    We had a wonderful New Year’s Eve then brought in the New Year with the most amazing foreplay and intercourse I had ever had. Unfortunately, the condom broke just as he came so I got a full load at the same time having a very intense orgasm.
    We tried to find the morning after pill the next day but no one had them.

    We were intimate every day through Saturday before returning home on late Sunday using condoms the rest of the time.

    I took the morning after pill today hoping it will still work. My period is due on the 14th so all I can do is pray I didn’t get pregnant.

    2
    # 75854 - by Denise / January 6, 2025
    • - Dating Disasters -
    Straight Male / 39

    I Got Cougared With An Audience But The Kitty Wouldn't Purr

    Tammy was an older coworker, 30 to my 18, who had made it clear that she was attracted to me from the first time we met. I was flattered, but I not only had a girlfriend at the time, I wasn't really attracted to her. She wasn't ugly. She just also wasn't pretty.

    I didn't tell her the second part, of course, but she respected the girlfriend part and everything was cool.

    Fast forward a year. I'm 19. She's 31. I am fresh from a breakup. Tammy approaches me and is being very flattering and openly sexual as well as sweet. She is expertly stroking my ego and I don't have a reason to not give her a chance anymore. Not then, anyway. At 19 I was not the type to be able to just say, "Look, your nice. You just don't make my dick want to come out and play."

    So, I go out with Tammy. Naive me figures if we go out, she will realize that our age gap is too big and we have nothing in common.

    That should have been true. I did not, however, at 19 have a grasp on how little a woman cares about anything when she is horny and has a chance to put the cause of horny inside herself.

    So, our date is boring as Hell. It ends and I am shocked when she asks me inside. Again, I don't know how to say no, so I go. I'm confused and not really excited about getting laid for the first time ever, but I was 19. Excited didn't matter I could have fucked extra wet mud and come back for round two.

    We get up to her apartment and go in. Inside it reminds me of my grandma's place a little. There were those doily things and candy dishes and stuff. Not exactly a den of erotic pleasure, but whatever.

    Tammy takes my jacket and, without pretense, leads me to the bedroom. She opens the bedroom door and inside are shelves and shelves of Doughboys. The laughing ones you poke in the tummy.

    There are statues and stuffies and action figures and everything. All sizes of Doughboy. Probably close to 150 or 200 of them. Each and every one positioned facing the bed. Each and every one with that smile.

    I tried to ignore it and perform, but it was super weird. No matter where I looked there was a Doughboy looking back and watching me try to fuck this plain looking, no personality having chick.

    I'm still not sure how I was doing with my performance that day either. Not really. Like everything else, it was weird.

    Tammy has been undressed and we have been playing around for way to long, but for obvious reasons, I'm not fully ready and despite her urgent pant removal and open legs body language, Tammy doesn't seem all fired up either. She isn't really doing much of anything or reacting.

    Well, finally, I manage to fantasize my way into being hard and decide to get on with it. I get on top and start. At 19 I wasn't the most experienced, but I had done a few things and had earned some confidence. With Tammy, it all went down the drain.

    No matter what I did, all she did was lay there. She didn't make a single sound or move a single muscle except to maintain eye contact which was actually worse. Different speeds, angles, depths, harder, softer. Nothing. And she didn't even feel good. At one point I distinctly remember thinking that I could have jerked off it would have been faster and better.

    Eventually, I am able to make myself cum which I'm only happy about because it means its over. I was confused and felt like I failed and just wanted to leave. Which I did soon after, but as I was, Tammy asked with all sincerity if we could do it again soon.

    2
    # 75682 - by LaughingJarl / December 30, 2024
    500 of 75,765 Confessions Displayed.

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