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.

Problematic Truth Or Dare Game

I attended what was supposed to be a "girl's sleepover" hosted by my best friend. There were four of us in the group, all female and 15 years old.

I enter best friend's home and was greeted by two of them. All we had to do now is wait for the last person. Little did I know, the group agreed to inviting a few more classmates for the night (three males, also 15). One of them happened to be my boyfriend, but no one was aware of the fact at the time. We've been dating for only 2 months.

Hours later, everyone voted on playing truth or dare. The game started off as friendly, but evolved to more inappropriate questions and dares (do you touch yourself, do you read nsfw, and more). I could tell that everybody was in the mood. My boyfriend was next and chose dare instead of truth. Someone from the group dares him to unzip his pants in front of the group, so he stands up and follows their request. We were all giggling and making comments on how big his dick could be. For some reason, I wasn't uncomfortable or upset. I found it pleasing seeing my boyfriend like that.

After taking turns, the game mainly focused on taking off articles of clothing. My boyfriend kept taking dares, undressing until he was (the only one) naked down there. He was rock hard from the exposure. My best friend suggests that he picks someone to go down on him. He points at me, all of our friends reacting with shock and excitement. He drags me to the bathroom and shoves my head closer to his member. I began by licking the tip and teasing him. Afterwards, I was sucking his cock down while using my other hand to play with my clit. I could hear my friends listening from behind the door, so I began sucking harder. I wanted to show them that he was mine and only mine. He pumped his seed inside my mouth, calling me a good girl. We continued kissing near the sink and suddenly heard knocking. Friend tells us that best friend's older sister was on her way here. My boyfriend and I jumped and put back our clothes on. We left the bathroom, still horny and sweating from the experience.

My best friend's older sister arrives and checks on us in the bedroom. Tried to block my boyfriend's shirt, which was slightly covered with white stains. Older sister looks outside the room and we all realised that the bathroom lights were still open. Everybody in the group responds nervously, saying that best friend was simply brushing her teeth and forgot to close the lights. Older sister didn't think much of it and leaves to her bedroom. One of our friends had to leave early and we continued the sleepover normally.

Days later, my best friend sits next to me in the cafeteria to discuss the crazy sleepover we had. She tells me that her older sister went up to her and questions the strange goo she found in the toilet seat. She also discovered tissues we used to wipe ourselves. Best friend's sister got the hint that we were doing inappropriate things when she was gone. I look at my best friend stunned, praying that they don't tell this suspicion to anyone else. Told my boyfriend about it, luckily nobody never brought it up. It was awkward when my best friend would invite me to her house, having to face her older sister.

My boyfriend and I have broken up, but we are still in touch and are friends til this day. It's enjoyable looking back to that memory, hope to experience it again.

  • My Little Story

    I was fucking with a guy from my summer job at the pool. It was Thanksgiving time in my senior year, we went to some friends' house to watch tv. Things got hot, some boobie kissing, some finger action, we went back to a room, he rolled on a condom and we got to fucking. He came, I slipped his condom off like I always did to lick him clean. The condom was leaking from a big tear in it. It was only a moment but I knew he had spermed me, and it was the worst time of the month for that.

    I licked him clean like I always did. I didn't say anything about the condom, if something happened I would take care of it. Big girls always knew the drill.

    When the time came, my best friend Beth went with me. The nurse told me I had to think about it and come back in two weeks. She told me that being a mother was the most important thing in my life. Embrace your baby she said. We had gone to an pregnancy assistance center, not an abortion clinic. It didn't matter, that nurse got to me. I got sick at the stomach thinking I had almost aborted my baby.

    My mother noticed I was nervous and stayed home not going out. When she sat me down I broke down begging her to let me keep my baby. She hugged me and told me all babies are welcome and we cried together.

    Well my baby is seven, she is going to second grade. I'm a teacher now, my parents bought me a house last year. And a car. I haven't dated since that night I got pregnant. School, motherhood have been my thing. That nurse, yes that nurse saved my baby's life. I volunteer at the pregnancy assistance center.

    Am I regretful of how I behaved in high school? I'm terrified that one day my daughter may find out. My baby daddy isn't much of a daddy. I haven't wanted sex from that day.

    Getting Fucked In Brazil

    Expat living in Southern Brazil, had two beautiful girls to play with. Now they are both pregnant asking for money, my vasectomy notwithstanding. Be careful out there. Vasectomy notwithstanding the women's claim is enough.

  • Dating

    I had started dating this women and things were great. She was only a couple of years younger than me, good job and with only one kid who was a daughter that was away at college.

    One night I am at her apartment and we started making out on her living room couch. Our clothes are off, I am on my back and she is on top of me. She then slides my cock into her and we begin fucking. Just after we started I heard a sound and her apartment door opens. In walks her daughter who immediately sees us and says she will come back later. My date tells hers to stay and after a little convincing by her mother does. Next thing that happens is her daughter sits on the arm chair right across from us and the two of them start having a casual conversation. I didn't know what to think or do so I did nothing. Her mother is still riding me but moving slowly up and down. Then at one point she tells her daughter to hold on. She begins to ride me faster and then shortly after we both reached climax. Right after she tells her daughter to hold on again while she leaves the room to go and clean up.

    I am left naked in front of her daughter and the one part of me that was somewhat hidden by her mother was fully exposed. I was still very hard and it was very noticeable. Her daughter apologized for walking in on me and told me it wasn't the first time seeing her mothers dates naked but it was the first time seeing one make love to her. She then added it appeared her mother seemed to enjoy it as did I.

    Her mother came back dressed and told me to the same. I left the room and as I walked away I heard her daughter say " he has a large cock". I cleaned up, got dressed and came back. Her daughter said she needed a shower and left. She came back a few minutes later to get her bag which she left by the door which normally would be no big deal but she was naked. I mentioned it to my date that her daughter seemed very comfortable with being nude. The reply I got was that she danced in a strip club so she has to be. I was then told that the 2 of them spend most of their time naked and that I should join them that way too. She tells me what I already overheard earlier that her daughter thinks I have a large cock, She then tells me that the two of them talked about sharing a man in the past and that the 3 of us should have some fun together before she goes back to college.

    The night started off a little rough but things smoothed themselves out. I was never naked in front of a date's daughter before. I was never watched having sex before, I never saw a date's daughter naked before. I never had a threesome before and would never have thought that it would have been with a mother and daughter.

    Dating Woman With Asberger's

    Last year I found Marnie on a dating site who seemed very intellectual and hence my match, but when I met her I immediately found her behavior rather strange in a way I couldn't quite describe to myself. But it wasn't long before she openly told me that she was on the Asberger's-autism spectrum, which explained a lot. She often didn't understand things with shades of meaning, but was extremely blunt about almost everything she talked about. Our first date was at an art gallery, and while she certainly enjoyed some of it our tastes seemed rather different, so there wasn't a lot to talk about there. She was thin, more dainty than cute but certainly not bad looking, and felt like she had a lot of energy, but only rarely displayed it.

    Afterwards went out on a balcony to talk outside a while. She had a music degree and did individual lessons for a living, but lived with her parents still in her late 20's. It also turned out that the place she lived in Chicago where she studied was a mile from where I once lived, though at a different and shorter time. I told her about some of my studies in history and literature, but she didn't seem very interested in it, though I think what her lack of expression really meant was that she hadn't studied those areas. Her knowledge was pretty narrowly focused on music and parts of psychology, and often kept coming back to those in the conversation, almost as if she didn't know what else to talk about.

    She suggested we go to my car, and we sat there a while longer, talking about dating experience. She soon admitted that she didn't like very much physical touch, and wasn't into kissing or sex, but had many dates with guys in Chicago where she usually either gave them a handjob, or watched them jerk off. I said that of course my experience was wider, but I enjoyed a good handjob. I mentioned I got hard talking about this and she asked to see, so I unzipped and showed her my erection. Soon she had her right hand gripped tightly around it, with surprising strength, and pumped me solidly with an earnest look on her face, very steadily for several minutes until I started to spasm and ejaculated all over her hand and my pants. She laughed a bit, and then asked if I had something to wipe up with, unfortunately I had nothing to spare but it wasn't that cold yet in the year so I took off my shirt, throwing it in the backseat after we used it to clean off as best we could. I thanked her and took her back to her car.

    I thought that might be it, since she said she often just had dates with guys once in Chicago and never saw them again. But we did get together several more times. Once I gave her directions to my house, but she was totally confused by the street directions and called me when she was lost; she gave the street corner and I realized she was just 6 blocks away, so I walked over there and guided her in the rest of the way. At my tiny house we again talked a while, this time more about her family and how she liked them but also liked to get away when she could without telling anyone to live her own life. Again, this ended in a nice handjob, this time with me on the bed and her in a chair so she could direct my cum onto a towel. The lighting was much better this time and she seemed to get a delicious kick out of watching me lose control and spew my cum.

    At a third date, she met me at a library I worked at in the evening very near where she sometimes gave lessons, and I took a break so we could go into the empty back room where she jerked me off into a wastebasket. On our fourth and last date, she invited me to her house while her parents were on vacation, a largish split-level in the outer suburbs. This time she let me watch her naked in a bath and even take a picture with her face covered so I can remember her nude body. She wanted me to stay over, I knew we couldn't cuddle overnight but she did let me touch her a little bit more this time, and then again jerked me off both before bedtime and in the morning before I left. But frankly it was harder and harder dealing with her strange mannerisms, and doubtless for her to deal with my lack of understanding of how to relate to her, so when I said something about that she simply said, "OK," and closed the door on this brief, strange, but "with benefits" relationship.

  • Shocked To Find Out What Was Between Her Legs

    After college working as a barmaid and then as a cross training sales associate, I went to an office job for the benefits. The HR lady, she came across as butch to me, was interested in my work out routines and invited me to go with her to her gym. She helped me get settled, offered to take me to lunch and give me the onboarding orientation. I went with her and there was no question she was making a move on me.

    I decided to throw the curtain back and asked her what her favorite sex was with her partner, and added, and what do you like her doing with you. She never missed a beat, definitely a butch answer and she wanted her partner to kiss and make love to her kitty. I asked her how she liked her girls.

    From there we went down all sorts of avenues, and she complimented me on being in shape and she liked her girls firm and tight. She was 29 to my 25, and I accepted going out with her on Saturday night.

    We went dancing, I wore a small tight dress for her, very tiny thong, no bra. She couldn't keep her hands to herself and we made love with our eyes. We went back to her apartment, were totally undressed by the time we hit the bed. I keep myself totally smooth down there and she went down the minute we got in bed.

    We kissed and I reached down below and she kept my hand away. But I'm strong, stronger than I look, and when I grabbed I was shocked to find a penis between 'her' legs. In a second I went cold, 'she' tried to soften the news. She called herself a tranny, and had no intentions of giving up that thing between her legs.

    I figured my job was no longer available and didn't show the next day. I'm working at the cross training club selling memberships to girls that want to look good. I'm not ashamed to ask them to prove it to me. These girls don't mind, I prove to them I'm a girl too.

    Too Loose To Date?

    I'm a single mom of 4 grown children. All are out of the house and have their own places now. I have had the house to myself for a couple of years now. Been divorced for over 4 years. After the initial few months of being depressed I started feeling better about myself. I'm in decent shape. I'm 5'5" 146 lbs red hair 34C. I have always loved sex ever since I started in my teens. I married my HS sweetheart at 21and thought we would be together forever. Unfortunately he left me for his young girlfriend. It was pretty hard on me. I had sworn off men forever! I started buying all kinds of sex toys because I was still horny all the time. In the first year after my divorce I spent nearly $2000 on sec toys including a fucking machine from Ken's twisted minds. And I have 11 dildos that attach to it. I kept buying bigger and bigger ones. The feeling of getting stretched and pounded as hard and fast as I want for as long as I want was-is amazing. But just like anything else, over time I've started missing things like sucking cock and getting eaten out, or he'll, even just kissing. So for the last year or so I went on a few of the popular free dating sites and apps. Never had a problem getting a date. I still look good I think. But of the 6 men I have had sex with it always seems like a one and done. I finally asked the last guy if he just dated me until he got some pussy then went on to his next conquest. He said I think you're really pretty and you're very nice and you give great head. But please don't be upset because this is as honest I can be, you are just too loose. Fucking your pussy feels ok for a minute or two then I really can't feel a thing. You don't do anal and it's really hard for me to cum from just a blowjob.

    I was floored. I thought my pussy snapped back into shape like after having a kid. But apparently I've ruined it. I turn between getting rid of the toys and letting it tighten up, or even getting surgery to tighten it up. But quite honestly I can't. I love being stuffed. I closed all my dating accounts and I think I'll just keep doing myself. I have considered finding a hung black man but I'm afraid he'll tell me the same thing. After all one of the guys I dated was pretty big.

    But I miss the intimacy between a man and a woman too. Ahhhhhhhhh!!!! I'm stuck between a rock and a hard place!

    Choices

    After years of making sure that all of my partners wore condoms Or going on the pill during relationships I let my guard down with one person I thought I could trust and it bit me. About six months ago I met a guy named Dave whom I really liked and thought I had a future with. He has been trying to extricate himself from a prior relationship that got pretty complicated so I backed away. Wehad kept in touch and I kept some hope but I am an attractive small Latina Woman who often gets attention and I’m 30 years old so I’m not waiting around forever.

    I also have a friend of about 10 years named Carl. Carl has been a good friend and he’s very sweet I know that he has had a crush on me for most of that time but I am not being attracted to him really and I have just enjoyed our friendship. He always seem to respect that and we have spent a lot of time together going to concerts and hanging When I am not in a relationship. He just has always seem to be there.

    So some mutual friends of ours were having a big wedding and I had hoped DAVID would be able to escort me as has happened too many times he could not get away. Carl asked me to go with him several times him and I agreed.

    We went to the wedding which was in a very exclusive hotel so Carl and I shared a room to save money. It was not the first time that we had slept in the same place as we have camp together and traveled so I wasn’t at all uncomfortable. The wedding was beautiful and we had a great time dancing, sneaking outside to smoke a little weed and generally just having a lot of fun. Carl Got pretty drunk was having fun. In fact he was dancing with the same girl for quite a while and I thought they were hitting it off. Late in the evening I just found myself exhausted and sweating from all of the dancing and I found Carl and told him I was going to the room to get some rest. He was sweet and offered to go with me but I told him he should stay and see how it went with the girl.

    So I’m going up to the room and despite being barely able to keep my eyes open I decided I would sleep better if I took a shower. So I took a luxurious shower in the spa like bathroom. When I came out Carl was still not back and I looked around in my luggage for a nightgown but I guess I either forgot to pack it or was just too tired to find it. I remember thinking I would just sleep in a T-shirt but then I lay down in the huge comfy bed and when I put the covers over me I was out like a light.

    Sometime later, and I didn’t even hear him come in the door, I thought Carl laid down beside me and hugged me over the covers. I let him hug me for several seconds but then realized I was nude under the covers and told him that the hug was nice but he should sleep in his own bed. He said OK I just wanted to give me a big hug so I kissed him on the forehead and told him to get some rest. I heard him go into the bathroom, pee and Brush his teeth. I heard him get under his covers on his bed and almost told him to turn the bathroom light off but I guess I was just still exhausted and I fell back asleep.
    Just a short time later I woke back up and realized I needed to pee and also realized that I was going to have to go into the lit bathroom naked. But, I heard Carl snoring and I thought I was safe so I tiptoed into the bathroom and peed. I turn the bathroom light off before I walked out but as I walked by Carl’s bed he grabbed my arm and pulled me down beside him. He’s a big guy and when he told me he pulled me right under the covers with him and I could tell that he was completely nude and also very aroused As I could feel his hard penis against my thigh. I asked what he was doing and he just said that I was so beautiful he needed to feel me one time. He kissed me hard on the lips and I was very hesitant when he Immediately slid a finger inside of me. I was in full ovulation so my vagina was already very sensitive and wet. I am Moaned despite myself at his touch and when I did he slid his tongue in my mouth and I just kissed him back.

    I put my hand on his fairly large belly and tried to create some space to give me some time to think but he was having none of that. He moved over between my legs and mounted me and I could feel his very large penis head against my vagina lips. I finally separated my mouth and said Carl we can do this one time but you can absolutely not come inside of me. As soon as I got the words out he pushed him some fully inside of me and I gasped at his size. It did feel good despite his body weight nearly crushing me as he began to pick up the pace and fuck me harder. He was grunting loudly and telling me how sexy and beautiful and tight I was. I let myself get into it I thought I was going to come rather quickly when suddenly Carl stiffened , Lifted his head and howled. I thought to myself oh shit but I couldn’t push him off me and I felt his cock just explode.

    First & Last One Night Stand

    Let me just say that dating in your mid 30s is easy thanks to the internet. I've been divorced for a couple years and I get more dates now than I did in college.

    Anyways, I drive an hour to meet a guy. We have a nice dinner and he's in great shape. Really not very smart, but has a great body. I know it's not going anywhere, but I have a few to drink and he takes me back to his place leaving my car at the restaurant.

    We are full on making out in the parking lot and I kinda remember stroking his dick through his jeans on the ride back to his place. After that I don't remember too much. Just that his placed smelled like a dog and we had a lot of sex.

    I woke up sore and naked with a major headache. At the time he was in the shower. While looking for my underwear I found a used condom in the sheets and his cellphone. A message on the screen said, "that's a big ass, tear that shit up for me".

    Obviously I open his phone, and to my very frustrated surprise I find he'd been snap chatting his friends naked pictures of me. I find over a dozen pics of him fucking me. Mostly from behind with my ass in the air, but a few of me asleep and naked.

    In the chat, he's texting his friends that I'm passed out but he's going to fuck me again before getting in the shower. A few minutes later, he texts a close up of my vagina with a used condom hanging out...

    Anyways, I delete the pictures, clean myself off with a dishcloth from his kitchen and get dressed. I play it nice with him when he gets out of the shower because I still need a ride back to my car. All this to say I learned my lesson. No more one night stands and if a guy wants a piece he's going to have to leave his phone in the car or something...

  • AFTER THE PARTY

    They'd all left, just me and two other guys remained. 'Let him fuck you', one said. 'What'. 'You heard', he barked as his buddy undid my pants. Holding my head he forced his cock into my mouth followed by his friend up my arse, spit roasting me and wanking my cock. It was over within a couple of minutes their lust satisfied and me a cum dump.