Adult Confessions

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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 / 29

Been There, Don't Fall In Love With A Bad Man

All the warnings don't help if you can only 'see' him. Or her. He was a man who overstayed his visitor visa and was working as a night manager of a fast food restaurant. No one understood him, everyone was against him. I was the only one who was on his side. I married him in secret in another state in an in and out wedding, legal but didn't feel like I was married.

It took years for me to accept that I was convenient, he had a life outside of my heartless marriage. Including illegal activities which I didn't know about. Never reported on the tax returns. When he got 'busted' it was a tip from a woman who he had left hanging.

I'm now recovering, he is in jail. My credit score is non existent, my job barely pays rent. My kids live with my mother, I can't support them. My father cosigned for me. I met a man who is not a good fit, but I'm powerless to say no to him.

I went to a therapist, nothing positive came from it. It's Valentine's, finding love with bad suitors.

Sorry for the downer, love is in the air, pick better, don't be like me picking total losers.

0
# 70089 - by Valentina / February 14, 2024
    • - Dating Disasters -
    Bi-Sexual Female / 21

    Last Nights Encounter With The Ripped Guy

    Ben was hot as hell. Great looking, incredible body, really ripped but not a gym rat, he works out but naturally has a muscled body. He is tall too and after our second date, we were making out and I kept rubbing his crotch. He told me he would cum in his pants if I didn't stop. So I wanted to pull down his pants on my couch, and he said that I had to take my skirt and panties off first. Well, I don't wear panties if I don't have my period, so off came the skirt then I pulled off his jeans. Then his underwear and then I saw it!

    I haven't see a cock that small since my younger brother was about 8 years old. It was thicker than my brothers but honestly not as long. The head was pulled into his sack and to be honest I had trouble with the low light telling where it was. He reached down and pulled the sack back and I could see the little head. With my finger and thumb I grabbed it and started pulling on it. Hoping it gets much bigger, but when it was at least long enough I could put it in my mouth it was only about 2 inches long and probably only as thick as my thumb. I had to suck him and had to suck him till he shot off in my mouth, it was the only way I could keep from laughing at it. Now, I'm not a size queen by any means, but I do need something I can feel. Honestly; I'm not sure he could actually get that little thing into me past my outer lips. I sucked it like I was sucking my thumb, because evertime I tried to suck it like I suck cock as I bobbed up it would come out. So I just kept it in my mouth and sucked on it, occasionally moving my finger on it. Then he said it, he was about to "blast" his "load". I honestly knew he couldn't blast anything much less have a "load". It came out, hard and fast, about 4 spurts and his little cock with marble sized balls was finished.

    I asked if was good for him and he was soaring, and thanked me, complimented my skills. Then he said he wanted to return the favor. He wanted to eat me. I told him not to, but he was so down about it, I told him I get off better if a man rubs me down there. So he put his hand outside my outer lips and I closed my legs and told him to move his hand up and down really fast. I had to pretend, I started breathing harder and harder, and almost screamed for him to hold it still and push. He pushed his hand on my pussy and I moaned and screamed I was cumming. All in all he had his hand on my pussy for about 3 minutes. I faked it all. He wanted to spend the night but I had to get him out of there.

    After he left I didn't even masturbate, I just laid in my bed stunned. Mr. Perfect, and he has a baby sized cock. I didn't answer his calls for about 5 days, then went out with him for dinner, back at his place, I drove, I told him my ex fiance came back and we wanted to try to make it work. He made me swear that if it didn't work out I'd call him.

    NOT! I hate to be that way, but I know I'd never have an orgasm with him and to get properly sexed up I'd need to cheat. I wouldn't want to live like that. He calls about once a week.

    1
    # 69975 - by Cher / February 7, 2024
    - Dating Disasters -
    Straight Male / 42

    Bookish Facial

    A few years ago I met a slightly younger lady at a book club. She seemed interested in something I said and followed me around a bit to talk to me. I actually didn't think we had much in common, and thought her rather plain looking, though not ugly. She had dark hair, was quite tall with angular features, and a lot of freckles. But she seemed interested in knowing how I spent my time, so I invited her over for some movies I was planning to watch. She soon wanted to hold my hand, and let me feel her up while she sat in front of me, even to to point of letting me reach under her pants and massage her clitoris to orgasm. She asked if I wanted a handjob, and I quickly accepted. She knelt in front of me and released my cock through my zipper, stroking in earnest while looking up at me with curiosity and interest.

    After a while I asked if she ever gave blowjobs, she said she did but didn't like cum in her mouth. I asked if she would take it on her face instead, and she said she had never done that, and seemed surprised by the suggestion. She asked me if I did that much, and said it was an exciting ending. This seemed to obsess her, and she kept asking me about my interest in it and what it was like. I told her I was sorry if it offended her, but she just said it seemed strange and she was curious about it. Talking about it turned me on, even if she didn't seem to relish it, so I asked if I could try it. She said "I suppose so," and so once she got me fairly excited I stood up and started stroking my cock into her face. She never did suck on me, though I rubbed my cock into her lips a few times. Thinking about cumming on her lips was very exciting, so soon I was squirting hard, and pulled back just an inch so I could cover more of her face. She just sat completely still, staring at what I was doing, and I made sure to go under her eyes so she didn't have to close them. I rubbed my cockhead on her cheek to get off the last few drops, then laid back down. She sat up next to me on the couch and stared right at me, asking if this made me happy. I said I loved cumming on her face, and thanked her for giving it a try. She kept asking what I thought of seeing my cum on her face; I said I liked it, and she just gave this look like she found this hard to understand. But she didn't wipe off the cum or do anything about it for several minutes, while some of it dripped onto her shirt.

    Her attitude changed, and I felt I had offended her, though she never said so directly. After another minute she went to the sink to wash off, then excused herself to leave. I thought I'd never hear from her again, but she called me up a few days later and invited me to her place. Again, I made her cum with my hands, and this time she followed up with a blowjob for a few minutes, again ending in a facial. But we never had intercourse, and soon I started dating someone else, and didn't hear from her again.

    0
    # 69974 - by Sam / February 7, 2024
    • - Dating Disasters -
    Straight Female / 19

    I Cheated On My Bf With A Stranger

    I'm using a new account to post this because I he knows my username.

    He is a very shy guy and not very muscular. A bit on the skinny side. I agreed to date him because I'd known him for a long time (our families are friends). I hadn't had sex in a long time and needed it. So I decided to do it with him. During the weekend, we went out. The whole time, I kept dropping hints by touching him and kissing him often. But he just smiled. I told him I was ready for it but he kept talking about something else. We went back to his place and I kissed him aggressively. He responded to it but then he got a call from someone and left me there. It was so frustrating.

    A few days later, I was sitting at a park, calming myself by looking at the sceneries. Some guy sitting nearby said hi to me. He looked like the jerk type and had a smug smile. But since I was bored, I accepted his company and actually he was quite funny. He invited me to his place for some drinks and since I was having fun, I agreed. We drank and talked a bit. After a while, we were on the bed with him on top, pounding into me. After feeling horny the whole week, it felt so good. I was so wet and sensitive down there. He fucked me relentlessly. When I orgasmed, I remembered my boyfriend. He seemed so pathetic compared to the stranger on top of me. I gave him all the opportunity while being so sexually frustrated. But it was all relieved by this guy who I had just met.

    My body wanted to let him come inside me, but I managed to force myself to push him off and let him shoot on my face. It was good sex but soon I realized what I had done and left in a hurry. I kind of feel bad for cheating. Should I tell him?

    1
    # 69971 - by Stacy / February 7, 2024
    - Dating Disasters -
    Straight Male / 21

    Oh Man Now What

    I met this women at the gym named Denise. Tall brunette fake tits tight ass married with 2 kids. I hit on her over and over any chance I could get. Even a little handsy sometimes feeling on her tight little ass. She would let it slide. She was in her early 30s was a stay at home mom i knew every thing about her and her hubby. What she didn’t like etc.. it was just a matter of time before I got her I could just tell. Her husband owns his own business works a lot. I finally got her to go get lunch which we did we flirted and went as far as heavy kissing I got to feel on her booty and she got to feel ok my dick. I’m half Mexican and had African American. I’m light skinned and have a nice thick dick from what I have been told. We did this a few more times and she finally went down on me. Her bj skills were not so good but hey practice makes perfect. I got a lot of head from her before she let me finger her while she gave me head. I knew that once I was fingering her it was a matter of time. Finally one day after our workout we went to the park instead of lunch she started to blow me and her tiny shorts where slid off and I knew what she wanted. It was hot and I was rock hard with her panties pulled to the side I put my dick right at her entrance and I struggled a little to get it to fit. She moaned loudly trying to take it. When I hit bottom I pumped a few times and her legs started to shake and her body tensed up. Oh she was saying was OH Oh OH OH and FUCK FUCK FUCK. But loud in lean loud, luckily there was nobody at the park. As I picked up the pace she told me don’t cum in me. I told her that she didn’t have a choice and continued to fuck away. I had my finger in her ass to which she stuck her tight little ass in the air for me to make it easier. She shook a few more times before I emptied my balls in her. We have been doing this a few months and she tells me the last time as I’m balls deep that she is pregnant and she has not had sex wit her husband in months. That was a few weeks ago and I’m still pumping away. She fucked her husband after finding out she was pregnant. Only thing is he will probably know when the baby is born I’m guessing? Mean time I’m still pumping her and she has learned to like anal. Wish us luck

    5
    # 69642 - by Nick / January 17, 2024
    • - Dating Disasters -
    Straight Male / 24

    The Refugee

    Hii everyone I'm sharing my confessions to you so basically I'm from Ukraine and you know there is war going on here from a year now has finally stopped so in the middle of September 2022 the Russian invades kyiv in that time I'm a freelancer doing my job there on September kyvi where I live or work getting attack and my place where I live is not getting any collateral damage so government seek to find place for refugees and I also did help in that time I so there is a woman comes to she's around 38 and she have a daughter age of 10 and her husband dies in war so she started live with me and from then we live together in my apartment but we both lost our jobs and so after that we both stated onlyfans togather for in seek of money and now it almost a year we doing this and she's becoming my mother
    This is my story ☺️

    2
    # 69639 - by Lucky / January 17, 2024
    - Dating Disasters -
    Straight Female / 27

    My Life Changed On A Dime,

    I went to his room without really thinking much of it. As soon as we were alone I got chills and wanted to go back to the party. He sat on the bed and pulled me to him, pulling my pants down. I lost my virginity, and got a baby out of it.

    I was 17, at my older sister's wedding. He was the groom's older brother.

    I have four kids now and we always have Christmas at my sister's house, with her brood and husband.

    I don't know why I'm telling you this, I guess I just wanted to talk about it.

    0
    # 69289 - by Sharon / December 27, 2023
    - Dating Disasters -
    Straight Female / 25

    Strange Guy...

    I am a normal sexually active 25 yr old girl. I date frequently and if I am attracted will have sex without long term dating or commitments.
    Early in my sexual experiences as a teen I learned that I enjoy anal sex. OK, more than enjoy. I love it and even prefer it to vaginal sex. To this point it has never been a problem. I never met a guy who was disappointed that I like being fucked in the ass. Guys usually break out in sheer joy when I tell them. Never had a problem getting a guy to fuck me in the ass until now.
    Met a guy a few weeks ago. We went out a couple of times and he made a move. We went back to my apartment with intentions of having sex. We were naked, fooling around and he had a major stiffy. When I told him I wanted him to fuck me in the ass I expected the usual bi time yes! Instead he immediately lost his erection and interest in having sex period. I tried and even offered him my pussy but he was completely turned off.
    First guy I ever met like this? Can any guys explain???

    5
    # 69168 - by Me / December 19, 2023
    - Dating Disasters -
    Straight Male / 23

    Who’s The Winner

    My buddy Mike and his wife Audra or Addi as she goes by are expecting there first child. They where married 3 years ago and I met Mike through work. Mike is an outdoorsy type camping type. Likes to hike like miles and miles camping where ever. So last spring I was invited to go with them and another couple. I am single so it was me and 4 other people. Every one is super nice and the women’s in there shorts and tight tops make it worth while. The day we went the other couple had come down with Covid.

    It was Mike Atti and I, so we continued with our trip. We got to our location and it was beautiful I’m not a nature guy but am willing to try it. We hiked the first day what seems forever.

    Mike proceeded to tell us that the trail was 28 miles long. I gave it a hard pass and said that I would stay at this site and we could meet up with them on there way back. Atti was also not feeling it and Mike and her argued a bit and I told them both it was cool I had booze I had a lake water food I was ok for a couple of days if that’s what it took. They decided to stay at my site and Mike would go for the day hiking. I got up made breakfast Atti got up and let me tell you Atti is a red head curly hair nice perky tits and a fat ass. She looks like she should be in porn or music videos. She is hot is all I can say. Mike is skinny white guy looks like Vanilla Ice.

    I’m half white half black but look more black then white. Just a little lighter with the black characteristics. Tall 6 foot 2 muscle on top of muscle is what most people say about me and I have never compared myself to another guy but women seem to like my main muscle is you know what I mean. It’s a solid 8” and thick. Very proud of my little guy.

    Atti was prancing around in a tight short no bra and skimpy ass shorts. It’s 10:30 in the morning and I’m like her baby girl let’s start day drinking made us some drinks more drinks and she had a little smoke as well. By 1 she was feeling really good when I got up to take a piss. Just being both of us she was a little clingy so when I went to take a piss I told her if you come with me you’re going to hold it. She giggled and followed me. I walked up to a tree and whipped it out I grabbed her hand and guided it to my cock. Her face said it all I let go of her hand and she held it for me pointing it and making swirly’s with my piss on a free. I found out that when she is high she is annoying as fuck. I finished taking a leak and she said now what still holding my dick. At this point my little guy was awake and her hands nice and warm were welcoming to it. I jokingly said you have to clean the tip. Lean over and lick the opening please. She looked and me and said really I said yes. So she did and after a few licks I pushed her head down and had her blowing me in the woods. As it got bigger she could barely keep it in her mouth. I stood her up and moved us away from the piss tree pulled her top up so I could see them titties and yanked her shorts off. I laid her down and she asked me to go slow. I could feel her breath as my dick split them lips. It took a bit for her to get used to it and then I went to town. Started out missionary then she rode me then doggie. Doggie was her favorite she came the hardest from it. I did not pull out and sent a few streams of cum inside her. We where camping for a week and when ever Mike was gone I was inside her. She did a little smoke to relax her and we tried anal. That’s a work in progress she took it but didn’t enjoy it. I told her that she will learn to enjoy it. She walked funny the rest of the day. Each day she asked Mike if he wanted her to go and each day he would say no it’s ok. Each day she would go into her tent and come out dressed. We would wait for a bit then go down by the lake and had her start to playing with herself. She would caress my dick and say how in love she was with it. Whatever is what I said I’d be balls deep soon enough. The week was over I hadn’t seen her in a few weeks when she reached out to fuck. This was about 7 months ago. Soon after the trip she found out she was prego. Last time I fucked her she had a belly bump. All she said is what if it’s yours.

    We shall cross the road when it’s time. In the mean time we still fuck doggie is still her favorite

    0
    # 69167 - by Tone / December 19, 2023
    • - Dating Disasters -
    Straight Male / 22

    What Do I Do

    A new girl started at my work recently and we hit it off. Been flirting and chatting and stuff but then I found out she is bi and has a girlfriend already.
    I can't get this girl out of my mind. Her instagram is super sexy too so I always see pics pop up on there.
    What do I do to get over this?

    3
    # 69087 - by Jay / December 13, 2023
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