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.

He Turned Me To A Whore

When I was 16 yrs old at school there was a guy started. to flirt with me and we started to talk and loved each other and he asked me for nudes and i sent him then one day he invited me to his house because his parents are out of the country I went to him stayed with him for whole week I let him take my virginity and he convinced me to try anal then he started to show me porn scenes and we try to copy and thing started to get more rough and kinky he wanted to throat fuck me till i puked on his dick , slapped me , spanking , hurting my nipples and clit with his hands and paper clips. for the whole week he kept using me and he was always taking photos for while he is fucking me or iam blowing him and I was ok because we are in love and he already have nudes for me. After that week he stopped answering my texts. after weekend I went to school all my friends didn’t want to talk to me the whole school staring at me and some guys started to say dirty things to me and i started to receive texts from guys want to fuck me and sending me pics of me that he used to take for me. The whole school was treating me as a whore. I Left school went to my home went to my mom to change my school but she refused because silly reasons that she is busy and other schools are far and we are in mid of the year. I skipped a week of school and i went to his home to know why he did that to me his answer was he sent to one of his friends and that guy shared it to others and its not his mistake and he can’t continue to be my bf. He made me really angry and i started to answer the msgs of the guys who wanted to fuck me and i started to ask for money by end of the year i had fucked around 40 guys.I thought I was revenging from him and my selfish mom. And Now Iam working as escort

  • Left Out

    First year of college I had been dating an 18 year old filipina girl with a huge rack and gorgeous young face. We had been dating for around a month and I had caught feelings for her.

    She lived in some dorms that had around 20 floors and shared her dorm with another freshman Asian girl on two separate full bunk beds. Her dorm was visible from the 4th floor from one of the parking lots facing the outskirts of campus which was mostly private buildings and empty factories. The dorms were small and two people could barely fit on each Bed. Each bunk bed had a separate window that you could see from the parking lot that were behind the bunk beds headrest. These head rests were two rows of wood planks that covered some of the window but were spaced out enough that you could see a persons head through them if there were no pillows to cover.

    One night after partying a bit we went back to her dorm to crash and found her roommate and her tall boyfriend sleeping together. A bummer to me because she had been teasing me with, some two piece white lingerie set with leggings suspenders she bought at the mall. We made out a little bit and I quietly got a few strokes in her wet pussy but fell asleep after I blew my load on her ass. I had to wake up early for work so we didn’t bother continuing and fell asleep.

    When I woke up it was still dark out and I quietly turned on a small desk lamp so that I could change and head out. I noticed that my date was still wearing her lingerie set and her ass was hanging out of the covers with all the dried cum I dumped on her. I didn’t think much of it and didn’t want to bother waking her up so I gathered my things and headed down to my car in the lot.

    While I was in my car about to start the engine I looked up and noticed that I had left the lamp on in her dorm and was immediately horrified when I saw a tall figure crawl into her bunk bed. I was thinking maybe I had been seeing things or looking at the wrong window and kept watch. The figure came back up and I could clearly make out it was a tall guy with huge arms. I could also notice that his head kept looking towards where the other bunk was, also visible through a window but darker as not much light was hitting that part of the dorm. Shortly after getting up I saw two hands grip the lower plank of the headrest and a gorgeous light skin ass in white lingerie suspenders slowly coming into view above the headrest. The guy was now caressing her pussy with his seemingly girthy cock which would occasionally pop into my field of view. He slipped inside of her while pulling on her suspenders and shifting her panties to the side.

    I couldn’t believe it, I was shocked and frozen. I thought about going back up but realized that I had no access to the building. I decided to keep watching and slowly I witnessed my dates ass cheeks pressing back and forth onto this huge figure. I pulled out my cock and began wanking to their movement.

    A few minutes had gone by and i was now witnessing her legs being spread out and could make out her white leggings. Her legs shaking a little. For the next 15 minutes I would witness her lock lips and tear into his back, and slowly switch position to suck him off with her panties facing the window. It was tough at times to make out how they were having sex but there were some pretty obvious signs especially when I would see the back of her head bob back and forth against the headrest.

    After about 20 minutes most of the activity had settled and witnessed this tall figure get up once more on his knees. I noticed a smaller feminine figure hop into the bunk bed with what looked like a teal silky night gown. There was some shuffling and I could see this guy was now laying down with his erect cock in the air. I can only assume it was his partner and my date who were now both giving him head.

    Im not sure what made them want to turn of the lights but soon after, the dorm room went dark and the last thing I could make out was my date taking it doggy style while this guy violently smacked and groped her ass. He leaned over her body and held her down, I could clearly see his arm muscles flexing.

    The day after I messaged her roommate asking if she was dating anyone and was responded back with a no.
    For a while I was sad but I mustered up courage to continue dating her for a bit, but ultimately did not last because I never felt the same sexual intensity from her since that night.

    Cherry Popped Roughly

    I logged to Grindr, I was browsing through profiles, I was quite horny that day, one guy about age of 25 invited me to his house, nobody was at his place. I told him that I am 50 years of age and he was okay with it.
    I went with the flow, picked up some condoms along the way. We didn't plan anything. I reached his place.
    We didn't waste much time in getting naked. I saw his member, though bisexual I hadn't bottomed to anyone. But I couldn't help myself and sucked him good, I sensed him applying some jelly kind of thing to my butt hole, but I was too horny to object.
    He turned me, took the condom packet, which I intentionally bought for myself.
    He spit on my butthole and I was on my way to my first anal experience. Needless to say, it was painful, and he was quite big for me. He turned the TV volume up so that my moans and screams don't go out of room. He rammed me good and mercilessly. He fucked me doggy style, missionary, and cared less for my pain. Unexpectedly he came all over my face and body.
    We had bath together. I felt my anal entrance wide open. We met two three more times at his place after that incident. And even in market place while I was shopping with my wife!

  • I May Have Been Young, I'm The Real Adult

    16 I played a freshman in college. I ended up pregnant and had to grow up. I also ended up married to the one time guy. He was 24 and he was threatened with statutory r**e. I lived with my parents until I was 26. Then I moved in with my husband of ten years. When he feels I don't show him enough affection he calls my mother and complains he was cheated. He's the mama's boy, I'm the adult in the room.

    Losing Control On My Date

    My boyfriend and myself have been in a long term relationship. For nearly three years ive been dating brad.
    Goofy funy nerdy in good shape amazing personality and smart. Cute handsome man i have fallen for him head over heels.
    Normally you share your fantasies or fetishes with your partner. Brad and i started dating at twenty.
    I had just turned twenty three two weeks earlier. A friend of Brad from his work went out with us.
    Cool guy chill athletic fun and funny. I enjoyed the night out at a local bar. We headed home Mark Brad friend from work came with us to the apartment.
    We played cards against humanity it was hilarious. We had a few more drinks.
    Before i know it they have me on the futon. Both taking turns eating my pussy my curvy slightly chubby body exposed and nude.
    Both using my hangers as fun bags. Then im sucking a dick while being fucked by Brad.
    Brad is good size six and a half inches but he is also thick.
    I swallowed Mark cum and felt Brad cum inside of me.
    We swapped and im cleaning off Brads cock in my mouth.
    I feel Mark between my legs and he had a longer not as thick as Brad but longer dick he fucked me as Brad encouraged him.
    They tag teamed me for little under a hour and a half.
    I was embarrassed shocked i felt incredible but shameful at the same time mostly because i really liked it.
    I felt cheap and like a slut.
    Mark left Brad jouned me in our room and he cleaned my pussy eating me out.
    We talked it was a fantasy of his to share me with another man.
    We sat up a few play dates and had a few random unexpected plays.
    I like other women im bisexual so i have invited a few girls into play. But mostly its other men i play with.
    Half the time its me and Brad together and it was always us together up front. Me getting switch hit or tag teamed.
    After awhile a year of us playing Brad encouraged me to pick men up and let him watch.
    I was shy and nervous about it but kinda liked the idea.
    It was fun after awhile. I got into fucking other men while Brad watched. Brad favorite was watching me dressed up pick up another man.
    It was the ice cream the cherry on top was watching me suck the guy and watching me get fucked like a cheap slut.
    Six months later Brad encouraged me to pick up other men and do solo dates.
    A few months of this and im bringing him home creampies.
    I found a couple while i was out by myself well was supposed to meet two coworkers that had to cancel i was already at the bar we picked.
    I had a drink played a game of pool with a light skin beauty ebony woman.
    We played a few games talking she stunning beautiful about my build. Sexy body and beautiful face. Brenda is fun to talk to.
    Some how the topic of our husbands come up. As well i spill the beans on me and my now husband sex life and our extras. She admits her and her husband share other women. She tells me normally she would never of been okay sharing her man. Even though she finds other women extremely attractive.
    But she needs a break from time to time from her mans dick.
    She decribes it and im sure i looked spellbound.
    Im trying to picture a dick as thick as she described or as long as she says.
    Its a little odd when her husband joins us.
    Martin he is four years older then me tall six one ish athletic handsome in a different type way. Ive never been attracted to a black man before and was still very unsure and nervous.
    Not that i want to fuck him i want to fuck his wife with my husband but thats not happening.
    Now i want to just get a peek at his dick see if what she said is true.
    I end up out in the parking lot with them and agree to follow them to there house a few blocks away.
    Im not dressed for a play date.
    Ive got on a black white and blue summer dress that stops at my knee a pair of flip flop wedges and a bra.
    We get there and i head in with them im nervous.
    Brenda is petite mayby one thirty.
    Im a size six five foot five red hair average looking but cute. Self confidence compared to Brenda has me nervous.
    Im a little chubby huge hangers and a thick butt Brenda called me a pawg and i blushed.
    We have a drink sit and talk .
    Martin is charming funny and handsome his wife has my pussy in need.
    We sit and martin rolls up some weed.
    I smoke with them.
    After Brenda opened my legs and i could not believe it.
    She ate my pussy like she was trying to steal my soul.
    It was incredible she made me cum so much i was shocked.
    Getting me completely naled
    Martin just watched the whole time.
    Then i noticed him standing nude next to us.
    I could not believe it he was huge.
    First wow just wow thicker then my husband. It was like a fat babies arm just dangling. Behind that a huge sack.
    Im nervous but want to watch him fuck his wife like ive watched Brad fuck afew of my friends.
    I watch him get hard.
    Thick long veiny huge bulbous head shaped like a bell.
    I dont know why but i want him to fuck me. Its not what i wanted at all originally.
    It dose not take long and i get what i want.
    Brenda sits down in a chair and rolls her self a blunt.
    Be careful Martin she is not on birth control her and her husband want a baby.
    Bet is all he says looking down at me with a coy grin.
    Lucky me im not at my most fertile.
    He manipulates and moves my body like a rag doll.
    Soon i feel him forcing my pussy stretching me open.
    I notice Brenda filming us.
    Getting up close on Martin horse cock sliding inside of me.
    Firstly after penetration i go fuzzy. All i know is im in pure ecstasy with a huge man on top of me with a monster cock fucking me.
    I blank out for a minute forgetting about everything. He fucked me into a state of zen bliss. I went blank.
    By time i notice the world around me its my own moaning that snaps me back into the world.
    Im cumming to hard to care what happens.
    Thats how i end up begging him to cum in me.
    That happened
    Then its round two of martin fucking me.
    Again creampie.
    Then his wife eats my pussy.
    We have a legit three some and i love Brenda pussy so tasty and juicy. I ate her pussy the entire time he fucked me doggy.
    This time i made him cum in Brenda so i could eat it out.
    It was delicious.
    I got dressed we smoked one.
    I had her email me our sex video and shared it with Brad.
    Me and Brad fucked he reclaimed me lol almost better then when martin took my pussy.
    Lucky im not pregnant yet dodged that bullet but here i am a few weeks after twenty five ant not sure if i should keep having extra sex with other men.

  • 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.