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.

Crazy Story About Friend And His Wife.

My friend and his wife had been going through a rough patch and decided to go to couples counseling. They were religious (or atleast tried to pretend to be) so they went to a priest for counseling. After a few sessions their counseling had apparently turned into my friend and the priest spitroasting his wife. My friend said after the first couple times it was strangely helping and they both got much more open with eachother.

Apparently the priest claimed to have had a vasectomy and always would cum in his wife. After a few months of these weekly spitroast counseling sessions, she divorced my friend and is now with the former priest who has been excommunicated. His ex wife is also pregnant with the preist's baby and based on the timeline of the pregnancy, it either happened during 'counseling' or they were hooking up more behind his back.

  • Teaching Her To Be Public School, She's Not At St. Anne's

    In the 11th grade we had a new girl in school. She was punished for having flunked the year and had to attend public school instead of her snobtown private school. She just needed to get her head adjusted, she wasn't a queen B, not anymore, she was fresh pussy in school, and that's all she was.

    The first home game and I asked her out. She looked at me like I was the hunchback of Notre
    Dame. But we had a rule, first one out of the mark got the date, no one else was going to ask for. The rule works, if she doesn't want to go 8ut she sits at home. By the end of the week she understood, and accepted that she was my date on Friday night.

    When you go on a date, you hold hands, you give a kiss, you go to second base. She wasn't a prude, she didn't want to be touched. I had to get the message across, she wasn't at St. Anne's anymore, she was pussy on the block, and I asked her out first.

    We won the game, the parties were everywhere. I took her to my cousin's house, where the beer is free. When the team wins, your date gives in. That's the rule. She was stiff as a board, I had to knee her open, cram my dick in her, she didn't like putting out. My cousin took care of letting it known, this bitch was mine and I was going to have to break her in.

    She complained, she should have paid attention, not flunk out of St. Anne's. She was a public school girl now, and she was no longer on the market. When our team won, I won. She was my date, she was mine. Dating a rich girl is a lot more trouble than you think. But she learned, she walks on the left, she holds my hand, she gets the beer. Public school girl. That's what she is.

    On Your Knees Now

    Degrading is putting it lightly...

    My gf is the kind of girl you can tell gives good head from just looking at her. Her big juicy lips, her extra pounds, and her almost cross-eyed look just screams oral. And she's so submissive that I can really indulge my urges.

    That's why I keep her on her knees when we're intimate. Much better experience.

    Occasionally I'll finger her during head but I don't want to ruin the bj by distracting her. Better to just smack her pussy to make her tighten up.

    Early on she asked me why I never fuck her. I said "idk what you're talking about, I fuck your throat everyday." She just goes along.

    I always liked bjs but I rarely got them from my ex's. This girl will do whatever I say so of course I say deepthroat!

    With this bitch her throat is the prefect c**t. She got those warm, buttery lips and round soft cheeks that I slide down so smooth and bust through her throat barrier with a quick thrust. I'll make it last as long as possible. Ideal time is two hours before I'll let her swallow my load down her throat. When I get really rough with the throat fucking her eyes

  • You Just Can't Cheat And Get Away With It

    We hired Felipe as a warehouse clerk. Felipe is a thin young man, beautiful honey colored skin, smooth, fine featured, nice penis, nice round buns. And kissable, affectionate, tight, a real pleasure to fuck. But Felipe didn't understand the rule. No other lover.

    My friend George, who goes to places I don't go, finds Felipe making out with a guy. He takes a picture, the tattoo on his hand leaves no doubt. I had to fire Felipe, he can't be trusted. And he hurt my feelings.

    Licking The Lesbian

    This sort of starts as a dating disaster but leads to something other than a disaster, though not a complete success either. In college in the 80s, I moved into a housing cooperative which was very liberal, there were many gay students living there and a very relaxed attitude to sex. Public nudity in the house was not unheard of, though not common. I was very sexually inexperienced though, so when a couple of the young women in the house invited me to what turned into a small orgy, I felt embarrassed because my repertoire was so limited. I couldn't have intercourse because I was scared of diseases and pregnancy (we didn't have condoms, or at least I didn't ask for any), and while I really wanted oral sex, I didn't know how to go down on a woman, and knew I would get any myself (or would feel guilty if I did) without reciprocating.

    Throughout that year I became good friends with Sarah, a large, dark-haired older lesbian student, whose frank talk about sexuality and feminism was often refreshing and encouraging. One evening shortly after the above debacle I confided in her my nervousness about lack of skill in cunnilingus. She gave me a few verbal tips, then boldly opened her robe to show me her labia and clitoris, talking about different ways to stimulate them with a tongue, emphasizing that you had to learn each woman's distinct needs and that what worked for one may not for another. I asked if I could actually practice on her, and she said I could but made it very clear that this was not part of a relationship, and she was never going to reciprocate in any way, I couldn't even take any clothes off. I agreed, and tentatively began to lick around her nubby clit. She gave verbal instruction and feedback which I found very helpful, and she forgave an occasional error on my part as part of the learning process. I very much felt she was doing this for me--and for my future female partners--not just for herself. Indeed, I she made it clear that she didn't enjoy it as much as receiving this from a woman, though she also said she more often gave head than received it from her partners.

    We did this for several nights over the course of the next few weeks, and finally after four or five sessions (hah, I almost wrote "sexxions" there!) I was able to make her cum. She said she had once received oral sex from a man, but I was already better than that partner, so my practice was paying off.

    We kept our trysts secret, no one else needed to know about this, and didn't let on that we were doing anything special. Occasionally we would talk about books or movies and invite each other to our rooms, which didn't always lead to practice sessions but sometimes did. These weren't just covers for our oral sex sessions, but real parts of our friendship which the cunnilingus just enhanced.

    There was still no doubt that Sarah enjoyed oral sex with her female partners more than with me, I was just the wrong body type, and smell, and so forth. But she did enjoy it, and at least once did come to me with her own desire rather than just agreeing to meet for my sake, and I did make her cum again that time.

    I often sat on the floor in front of her, but she also taught me to do it while she sat on my face, and increasingly got off that way.

    Late in the year she invited me to join her at a girlfriend's apartment, and revealed that she had confided in her about my training. The girlfriend, a skinny black woman, was interested in being another subject for me, and they talked about their differences in how they liked to be stimulated (Sarah liked more direct clitoral licking, the girlfriend more indirect). I decided I could learn from the variety, and was soon lapping between her legs while Sarah watched and occasionally kissed her. I couldn't quite make her cum though, and still wasn't able to fully translate my skills to a new person with different needs, so Sarah eventually took over and I watched her gradually bring her friend to a soft orgasm. We had dinner, and then an hour later I tried again, and this time did make her cum.

    During some of these sessions I would get a hard-on, but kept it in my pants, just occasionally letting it outside my underwear so it wasn't poking uncomfortably. When I went back to my room after seeing Sarah I would jerk off like crazy, and sometimes this made me feel lonely, though it probably wouldn't have been any better if it hadn't begin with my servicing her. At least I learned something from it, even though it wasn't fully satisfactory. After a year I graduated and moved on, never seeing anyone from the co-op again, but I was more confident in my future trysts and was glad about what I learned from my willing lesbian teachers.

  • Is This What It's Like...?

    Yesterday I had a male friend hit me up AGGRESSIVELY on social media basically telling me how much he wished I had an OnlyFans account and how he'd pay me directly for a dick pic. And how long he's wanted to see it and how long he's been crushing on me.

    This whole conversation came up in response to me offering to help take a look at his resume for jobs he might apply for in the near future. He knows I'm happily married (to a woman) and I mentioned my wife several times casually. He kept saying he wasn't trying to cross any boundaries but was just curious about me and what it would be like. I kind of felt like he wasn't listening, maybe I was too nice and didn't respond explosively enough to stop the behavior. He tried to contact me the next day and I made up an excuse to avoid talking to him.

    Is this what women go through with us males? Something seemingly unsexual suddenly turning weird like this and you left feeling confused and wondering what happened and how the conversation went south?

    I am so sorry, experiencing it firsthand like this was frustrating and eye-opening. My fellow males, read the room!

    Should I Sleep With Him?

    I posted couple days ago that I am a 22 year old virgin who is dating a 35 year old guy, he doesn't know I am a virgin.
    We met on facebook and he liked my photos and I think he dated me because he liked me and wanted to sleep with me and that's all. He texted at first that he want to know me in person to see if we like each other and if we get along we should start a relationship.
    But after our first 2 dates he didn't text me anything, I am the one who is looking for him and text him, I think I would even sleep with him but he doesn't asks me out anymore, I know it's too soon but I am intoo him he looks hot, I don't know what to do to get his attention, I thought about asking him to come to my place, is it wrong to do that, what will he think about this?
    Please help with some advices.

    Get Horny Easily, Ruin Dates

    So I'm really bad at dating.

    I've met a lot of girls that were really sweet and beautiful and I would always fuck it up by accidentally getting too horny while I was with them. I just wanted to fuck them all. One time I was with this girl in her car. We parked at a city park and just began talking. It was nice. I noticed she had huge breasts sticking out. We kissed once. Then I started making out with her. She noticed that I had a huge boner. She laughed a bit. Then she said wow, that was easy. I said, sorry.

    Then we kissed more and she looked down and I took it out while we were kissing. Then I slowly grabbed her hand and she jerked me off a bit. She made me cum. After that, she never spoke to me again. Happens every time. I cant help it. One time, this girl was giving me a hand job and I accidentally came on her dash. We didn't have anything to clean it with so she said she would clean it when she got home. Never spoke to me again. I've ruined a lot of dates with beautiful women because I couldn't control myself. Maybe 3 out of ten times, we went home and had sex. Still after, never spoke to me again.

    Wtf. I'm legitimately trying to find someone to be with, it's just the first or second dates always go bad.

    Still Scratching My Head

    I'm picked up by Mr. Niceguy at a wedding reception. dinner and the theatre, ride along the coast line with the shimmering moon on the calm ocean waters. It's time for the move, he takes me ------ to meet his exwife.

  • Extra Duties As The Maid Of Honor

    Don't judge.

    My older sister, then 19, got married to a man she met at work. As the date got closer she got cold feet. I was the Maid of Honor, and her younger sister. She was married on a Valium given to her by my mother. After the reception, where many people thought she was drunk, I took her upstairs to her honeymoon suite. She was trembling, hysterical at the thought of having sex. Petrified.

    We were brought up to be proper, sex in our house was reserved for marriage. But no one ever spoke of sex being anything other than a burden and a terrible one at that. My new brother in law is a very dominant man. When he walked in and found her crying, frozen in fear he went ballistic. He wasn't going to be denied and he took me instead.

    They went on their cruise honeymoon and my sister wasn't able to avoid the inevitable. Nine months later my sister and I gave birth five days apart, me first her second. We had to adapt to our realities, my sister to this day has a difficult time with sex, my BIL has looked to me to fill in for my sister. It's an all in the family sort of thing.