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.

I Can't Get Her Out Of My Mind And I Can't Move On Either

Her name I am making up. For this I will call her Cathy. I met her in college, she was getting her masters in social services and dreamed of helping out with the inner city poor. She came from an nice home or she would not have been at our college. She was pretty in a midwestern way, tallish, blue eyes, blonde long legs. I got involved with her that semester, she was an aggressive girl when it came to sex, I had my first body on body orgasm with her. She was moody too, and she had a chip on her shoulder and her whole issue was the poor and how bad they were treated.

I never fell for her, it was physical, a sex thing. But she fell for me and she was obsessive about it and I had a hard time keeping her at a distance. I went on to date another girl and after graduation she and I became entwined in a long term relationship.

After my LTR ended I made a trip to Chicago and I looked up Cathy. She was living in a rat hole of an apartment, making 28 thousand a year as a social services counselor. I thought by then she would be out but she wasn't, she kept it bottled up inside. That night at her ratty apartment I ate her, ate her with a vengeance, not typical of me, but I was hungry for her and when she wouldn't eat me right I slapped her face.

I took a selfie of her and me kissing and I sent it to her mother to let her know what kind of daughter she had. I wrote a sign and put it on her apartment door that read 'c**t eater'. I had more pictures of her and me when we were in college and when I got back home I sent those to her mother as well. Her mother already knew, as a matter of fact the people she worked with knew and the apartment neighbors were not surprised that she was a c**t eater.

I felt bad and went to see a psychologist about my behavior, she attributed it to pent up frustration with Cathy and unresolved issues, like I was really hung up on her and I hadn't moved on. She suggested I apologize all around, but no one really cared. I went to see Cathy and she let me in, I told her I wanted to eat her but the right way and show her that I could be nice. She took off her shorts and panties and sat on the couch and put her heels on the armrests so I got on my knees and ate her until she had an orgasm.

Cathy needs to be slapped around, she needs to be 'fucked', she needs to be shoved down and held down. I found a pair of binding ropes on the internet and tied her to the bedpost. She peed on her bed but didn't ask me to let her go. I am not a dom, I can pretend but it is not natural to me. But she needs a dom. Maybe not the high heel boots and the whip, but a dom.

We parted company for the last time and I have tried to stay distant from her, but she is in my blood and I can't forget her. She doesn't have anyone, she does her job, lives in her ratty apartment. I don't have anyone either, except 'Cathy' but I am trying not to go there.

  • Bi-Polar Crazy, But..Hot Body

    I have a cute, hot, petite blonde FWB who I get together with every so often. Problem is, she's also a raging, stumbling, embarrassing alcoholic, who starts drinking before I even arrive to take her out for dinner, an appetizer, etc. It happens every time without fail. If we go out, she will either be cut off at one drink because they'll see the condition she's in, or, if I know the staff or bartender, they'll tell me "Get her to ease up, or get her out of here before we have to kick her out".

    Thing is, too, that she has a fit, petite, hot as hell body, great, shapely ass, and is very fuck-doll sexy. The pure guy part of me can't ignore that. We started up a little bit at her apartment last night even though I knew she'd had a few at home, and I was getting hard just handling her body and kissing her. I wanted to throw her down as she did her makeup and shook her tight little ass in a short sundress that really highlighted her body. My brain goes from "Careful tonight, she's already half in the bag", to "Look at that ass..I'm going to fuck the hell out of her", which I usually do anyway.

    I've had to carry her out of places too many times, and go back, embarrassed, apologizing and adding more cash to my already high from guilt, tip. I know the deal with her and it hasn't changed. She's a raging drunk, bi-polar, embarrasses me around people I know, and I shouldn't spend any time with her. BUT..That body is just so hot, she's great in bed, and she's so easy to fuck, that I give in too often. I've never seen a woman wear dresses or sundresses like she does, perfectly tight and accenting her every curve. I can look at her and get hard. Even knowing she's nuts.

    There Should Be A Regret Category

    I married my coworker after a two year affair that ended his marriage to his wife. She and he have three kids and after the divorce she rented a two bedroom apartment in a complex not far from my house. The divorce provides for him to have the kids three days a week and she has the rest of the week, and they trade off weekends. My house, which I inherited from my parents has four bedrooms and a pool. The kids are at home here and I am at home with them. I would rather a hundred times that they are here than at an apartment, they will home school with me this semester. I don't pretend that I didn't know about the baggage.

    My husband and his wife are divorced but not unmarried. My husband hurts day and night because she is not with him. The children are here because of the apartment living, but his ex is in an apartment complex. I would like to convert the office den into a mother in law suite and convert the guest bathroom and laundry into an on suite. The third garage can be repurposed for the laundry, and guest bath and a small office for my husband. It will be later if and when we can update the kitchen and the master bath.

    My instincts go one way, not to mention all my relatives and friends, but my feelings don't follow my instincts. I hate the apartment complex, she is there because of me. Her children are here with me, her ex wants her here with us, I cannot imagine how she can stand being abandoned. If is my fault, and his a bit, but my fault for having an affair with him. Preparing meals for her children is one of my high points in the day, when she is here we prepare the meal together and look after them. We put them to bed together, and then she has to leave and I hurt so bad.

    I am so sorry that I brought this on her, all I can do now is work to correct it.

  • Finally

    I found out my fiancé was cheating on me and broke of our engagement. I was heartbroken but, through some friends encouragement, I finally got it through my head that I’m a young, 31, fit and attractive little blonde girl that men covet and it was time to put myself out there. I went on a few dates but they weren’t interesting at all. In fact, one guy was cute and I’d decided to sleep with him because I’d gone so long with out sex and just needed to scratch that itch. He turned out to be so lame and such a whiny millennial that I just lost interest and cut the date short. So fast forward to a month ago. I went out after work with a couple of single girlfriends and we were having fun, laughing and being silly when a guy started talking to one of my friends. She ambled off with him and my other friend excused herself to go outside and make a call.

    So, now sitting by myself I suddenly felt like a fool and was getting my things together to leave when a tall, good looking dark haired guy walked up and asked how the prettiest girl got left alone. I smiled and said it was just my luck. He asked if he could get me a drink and I thought “Well he’s cute enough” and said sure. We walked over to the bar and ordered two beers, for which he paid, and we began chatting. It started well enough and he seemed fairly smart. Soon though it became clear he was kind of douchey because he kept looking at himself in the mirror and at one point asked me if I was looking to play tonight or a relationship.

    I was a little surprised at his directness but said probably a relationship. He then said “Good to know, I have to honest, you are sexy as shit and your body is rock hard but if we went home and fucked tonight I know exactly what would happen”. I said”Ok, goofball I’ll bite. What would happen?” He said “ you’d fall madly in love with my cock and I’d never get rid of you without a bunch of crying” I laughed out loud And said “ Worst line ever. You are the king of the douchebags”

    Things work out the way they do and about an hour later I was naked in his bed kissing him. I was so horny I just decided to hell with it and his idiot charm won me over. He had gotten pretty drunk and while we were kissing I wrapped my hand around his cock and it was indeed very, very big but not very hard. I was afraid he was going to be too drunk to perform but he slid down between my legs and began earnestly licking my pussy. I was a bit embarrassed and I don’t think he even noticed that I came almost immediately. I had been so long since I’d been touched and when his tongue circled my clit I just let go. He finally rose up and kissed me without wiping his face and I could taste myself all over his mouth. It turned me on somewhat but not nearly as much as when he pushed his now rock hard monstrous dick inside of me. I gasped and before I could stop myself said “ Oh god”. He said “it’s a good dick isn’t it baby? Damn your pussy is tight and juicy” He began gently but after a couple of moments he began biting a5 my left nipple and pounding me harder. For several seconds every time he thrust his huge dick inside of me I lost my breath and I was afraid I was going to pass out. My ex wasn’t small but nothing like this guys. He finally let my nipple go and put his mouth right by my ear and repeated over and over “ Fuck baby your pussy is so good”. I got into rhythm and felt like I was enjoying it but the I began to think he was going to be drunk to cum and I’d wouldn’t be able to take this kind of pounding all night. I whispered in his ear “Cum on my belly for me baby”. He moaned loudly and just started hammering into me. My legs were spread as wide as they would go and I could hear the suction of his huge dick pulling in and then thrusting back inside of me and his balls slamming into my ass. This went on for a long time until he finally said quietly in my ear “I need this nut so bad baby”. He then slid his right hand under my ass and began pulling it into him as he thrust deep, deep inside of me. Suddenly his middle finger slid partially into my asshole and I gasped but the felt an incredible sensation and before I even realized what was happening I began screaming and cumming so hard that I lost control of my bladder and began peeing which felt like total release and my orgasm peaked while I was screaming and begging. Rather than grossing him out he seemed to ge5 more excited and roared “Take my nut, take my nut you fucking hot c**t” and I felt his dick just explode warm goo at the base of my vaginal wall deep inside me. I felt three distant hard squirts of his cum inside of me while he was buried fully and screaming “ Oh fuck” over and over. He then pulled out of me squeezing his dick hard and put it on my lips. By this time I was just so completely depleted I just let him and opened my mouth and began sucking on his huge cock head. Incredibly enough he just kept cumming and as I had no room to let it dribble out I just started swallowing and he said “ Oh my god” and I must have swallowed four full mouthfuls of his cum. He pulled out and I gasped for air and we both started laughing. He said “Ok, all bullshit aside that was my favorite fuck ever. Tell me you’ve had better? I admitted it was pretty awesome. He grabbed me and pulled me into him which, though I was gooey,sweaty and stinky felt very good. I stayed there until he started snoring and I got up on very wobbly legs and peed. I considered staying the night with him but while I was in his bathroom I heard him fart loudly and when I went back in the room it stank badly. Nota big deal in a relationship but all in all I decided it was time to leave as I began to feel a bit whorrish.

    So I’ve talked to him a couple of times on the phone and it appears like my vagina is actually causing the attachment although I will admit masterbating thinking about that big cock a couple times. My girlfriends tease my that I got “dick down” very well. I’d never even heard that but does describe what happened pretty well.

    Why was this date a disaster. Well, because I have been on three dates and fucked one guy since my ex moved out. Admittedly a great fuck but today I found out for certain that big “dick down” I got impregnated me. One fuck and I’m pregnant. WTF. Of course studly wants to marry me and start a family. God. Though maybe not the worst to have that dick to come home to every night. Big eye roll.

    Let Down

    The guy was a long time friend and we had planned for me to come over, smoke and chill. He was confident and boasting about his sex game so I had to try it out. He put me in doggy and lasted 5 minutes! I let it slide cause it was his first try in this gorilla grip pussy.
    I asked for round two since I was not satisfied where he excitingly agreed. After saying I wanted to be on top he still wanted to do doggy.... my man lasted two minutes. That shit was actually embarrassing.
    Then I went for round 3 and he had the audacity to say “nah I’m too tired” after telling me on ft he could go atleast 5 rounds.

    As a female, I’m disappointed. We “chilled” in silence for a couple hours too since he was being so hostile.... didn’t even give cuddles. I’m his second body and he was mine but lemme say... WHAT A WASTE OF TIME!

  • Bottom Line, Keep Your Bottom To Yourself

    I met him the night I had sex with him. It happened in my apartment around two in the morning, on the couch because my roommate was asleep in our room. Sex was all over the place, including pressed down on my stomach and him trying to fuck me in the ass. That's when I started to complain, telling him to get off of me. That's when my roommate came out, she hit him with a baseball bat we kept in our room and broke his head open.

    He was totally naked, so was I. My roommate was shocked at me, obviously I had gotten naked with him. I had also already been screwed conventionally, if you call being screwed on a couch conventional. But right then we had to deal with him, I got dressed, he was badly dazed and it was hard to get him dressed. We took him to the hospital, it was three thirty when we got into the E.R.

    He had a concussion, and he needed stitches. I told the E.R. he was my boyfriend but I didn't know anything about him, not even how he spelled his name. We told them he tripped and hit his head on the coffee table, which meant he had to have fallen backwards, and the E.R. doctor knew he had been hit with something, a lovers quarrel? In the end we got him back to our apartment at nine the next morning, on the couch and we had to look after him.

    Ten days later after he was cleared by the doctor I told him I was ready to give him what he wanted that night. I went with my roommate to an adult store and we bought anal lube, recommended by the girl at the counter. I told her I was giving it to him first time so she was into giving me all the advice, lube, lube, lube and I was going to regret it so be aware. On the way out she told me to avoid it, it just wasn't worth it.

    I lubed myself up, until I could get a finger in, I lubed his dick too. I knelt on the couch and bent over the back of the couch and opened my legs and waited. My naked butt out in the open, the lube ice cold in the air conditioning. My roommate went into the room so she didn't have to watch. It did hurt, it was uncomfortable, it was worse than your first gyno exam. He took a long time, it never ended, he blamed the lube. But he would not quit, finally he ejaculated and pulled out.

    The next day I went to the adult store and told the clerk she was right, not worth it, not sex, and I regretted it. Once, never to happen again. The baseball bat was the right answer, don't fuck with your ass even if he wants it really bad.

    Good Date, Bad Sex

    A little while ago, I went on a date with a really hot guy that I met online. We went out for a drink and had a really good time. I decided that he wasn’t really my type for dating purposes and so I wasn’t going to see him again, but that if he wanted it I was 100% going to hook up with him that night. It started getting late and he invited me for one more drink at his place, so I knew the hook up was on.

    Anyway, to cut a long story short, I had sex with him, and he was really not good in bed. He had a good time, but he didn’t last long and he did nothing to make sure I had a good time too. He fell asleep right after he finished. I was really horny and I was not satisfied! I went to his bathroom, sat on the toilet and started masturbating. It turned out I didn’t think to lock the door. He woke up and walked in on me butt naked, pleasuring myself on his toilet.

    He got really pissed at me for masturbating, asking wasn’t he enough to satisfy me? I got pissed back and told him no, he wasn’t , and that he didn’t even try to make me come, so I was going to do it myself, and then I yelled at him to get out! He was so surprised that he just went. So I finished myself off, had an orgasm right there in his bathroom, got dressed and left. He didn’t say another word to me - I think he was pretty embarrassed!

    The Big Date

    I met a girl through our circle of friends and after several weeks we decided to start dating. We did group dates for awhile as we had pretty much the same circle of friends.

    Things seemed to go well and we were getting pretty hot and heavy.

    She had given me several hand jobs and I had finger her but that was pretty much it.

    I had just turned 21 and she was 19. At the time we both still lived with our parents when not away at college.

    Things were getting to the point that I knew she wanted to have sex and it just so happened that my parents would be out of town all weekend so I planned a date.

    We went to dinner and a movie. The theater was practically empty so we sat in the back. We kissed and I unbuttoned her pants and slipped my hand in. She was wet . I spent most of the movie fingering her to just the point of orgasm then stop just short.

    She would open her eyes and give e me a look like... "you bastard".

    When the movie ended I told her that my parents were out of town and asked her if shed like to come over. Of course being totally aroused she said yes.

    We got to my place and she said she had to use the bathroom. She was in there awhile and I was concerned but she said she was fine.
    I grabbed her hand and led her to my bedroom where we undressed each other.

    Oh my god she was gorgeous!

    Up to that point we had not seen each other fully naked.

    She worked my penis with her hand until it was hard and then gave me a blow job as I leaned back on the bed. I had to contain myself so I wouldnt prematurely shoot my load.

    After a few minutes she climbed on top of me and lowered herself onto my erection. She rocked her hips and moaned but then stopped. She looked at me and said that her stomach wasnt feeling very good.

    Then she vomited all over my chest.

    Talk about mood killer!!

    We went into the bathroom and showered off. Each time she vomited I would hold her hair back for her.
    I left her slumped over on the bathroom floor next to the toilet naked with only a large beach towel over her and went into the bedroom to pull the sheets and make the bed.

    I carried her to my bed and slipped her panties on her and then pulled the covers over her. She must have said sorry a thousand times and cried that she ruined our special evening. Shit happens.

    I spent the rest of the night and the next day taking care of her.

    You might think that would be enough to scare a guy off but you'd be wrong.

    We had a whirlwind engagement and were married 6 months later.

    We've been married 26 years now and have 2 adult children.

    She has more than made up for that night a million times over and if need be, I still hold her hair when she pukes.

    Housewife And Mother

    My best friend starts dating a black man. He introduces me to his friend. Because of my best friend I go out with them. My brotherly boss hears about this and brings me into his office and tells me to stop seeing this black man. No offense but 'do not let his dick fuck you'.

    My best friend pushes me to date her boyfriend's friend. I go with them to an art fair. My brotherly boss shows up, takes me by the hand and gives me an ultimatum. If I don't stop seeing that black man I won't be worthy of his children. Go home with him now, or forever be pushed aside. Now or never, go home with him and be prepared to become pregnant.

    I tell my best friend I have no choice, I go home with my brotherly boss. He takes no time in putting me under him, in a short time following he impregnates me. From then on I become his housewife, sentenced to home and hearth, motherhood and wife.

    My best friend marries the black man she was dating. She works. She is not a housewife, a mother.

  • Unwanted Surprise

    My neighbor was forced to retire a couple of years ago. After I retired a year ago we started hanging out together. My wife made fun of us, I was his shadow. What my wife didn't know is that Joe invited me and taught me to suck cock. For as long as I remember I have been attracted to cock, in swim class, junior high gym, college dorm parties, golf showers.

    In spite of admiring cock I never actually held, touched or sucked on a cock. Joe offered, I accepted. Joe was a guy who had friends, friends who got together, nude pool parties, and more exciting, every one got a number, you matched up with your party buddy and you got action going on in the pool, in the den, in the bedrooms.

    For one party we all chipped in and brought some Chippendale dancers to the party, three dancers were auctioned off and I was high bidder on one of the dancers. I was expecting a huge cock, what I got was less than average, what I got was a droopy cock, what I got was a good looking guy who couldn't get it up. He offered his butt to fuck, but I want cock, I am not a top, hard, large, big cock guys. After winning the bid I got the veneer but not the wood.