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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 / 20

I'm Confused

Just a bit of context.

Firstly, I'm a girl and I play online games. I pretend to be a guy online to avoid guys hitting on me and all that stuff and only my friends who I know in high school know about this. This actually works great! I (mostly) don't get guys trying to hit on me anymore except a couple of times but I'll explain that later. The only problem is now I can't use voice, so all I can do is listen and type which is a trade-off I'm willing to take.

Anyway, my friends and I join a public server to play an mmorpg on and eventually I find a guy I like. He's super nice and we've typed to each other for a while now. I accidentally tell him that I like him while I was drunk and he tells me that he likes me too. So now I'm thinking that he's into other guys and feeling pretty disappointed.

But here comes the most shocking news. He later tells me that he's a girl pretending to be a guy. After hearing this I also come clean.

So now here we are. We're both girls pretending to be guys. And we're both straight.
We're still friends, but we both know each other's secrets. We've also finally talked with each other on voice chat now. Mostly when there's no one else around. Anyway, unfortunately someone hopped on at 3am in the morning and joined our voice chat as we were chatting and he found that I'm a girl. I later told him that I was my girlfriend. That sounds weird pretending to be the girlfriend to myself, but that was only after he told other people about me and I'm pretty sure half of them didn't buy it since I guess it was a bit strange I never use voice.

I later invited her to a private discord I have with friends that I use voice chat with so we could chat without worry of being discovered.

We're still good friends, but now I'm confused about my feelings. What should I do?

2
# 47418 - by GuyGirl / September 21, 2020
    • - Dating Disasters -
    Straight Male / 26

    I Thought I Could Stop Myself

    I (26 M) have been letting guys (21 in total) fuck my mouth at my job behind my gfs back and how I was going to stop it because its wrong.

    I couldnt stop, i couldnt resist. I thought to myself, well, I'll just download grindr and look around, thats all. Not even going to upload a pic or profile, just gonna see what i see. A couple hours pass and I'm still looking around at all these guys on grindr looking for head. I was about to get off from work and was just killing time browsing and I told myself that once I got off, I would uninstall it. I thought since I was just looking, it would be fun if I teased. I wasn't getting much attention with just a blank profile.

    I uploaded a pic of me on my knees in my security uniform, mouth shaped like an O with my eyes cropped out. My profile said I was going for a dick to be shoved down my throat until he cums down my throat. Oh boy did my profile do a whole 180. In less than 20 minutes, over 100 guys had viewed me and about 30-40 guys were asking to come use my throat. Damn it had me hard as fuck at work, precumming in my pants like crazy looking at all the dick pics sent to me, imagining myself gagging on each one.

    It was time for me to get off work. And so many guys were hitting me up. I couldn't help myself. I couldn't resist. At first I told myself, it would just be one guy, it would just be real quick and fun. I messaged one guy while I was in my car about to leave when another guy with this beautiful dick messaged me. I told him to come over too if he was okay with having me suck both of or he could wait and watch. I reached out to the other guy and told him the same and they both said they were down. I started scrolling through my previous messages and looking at all the nice dicks. I messaged another 4 guys, 2 of them said they were down. I gave all 4 guys my address, gate code, and told them the door was unlocked.

    All 4 of them were Hispanic guys, all of them had some thick chubby latino dicks. The biggest guy was like 6'2" and 280lbs or something and my lord he had a huge dick. It wasn't as big as the bbc I've had but it was so surprising and plump. I loved it. They all absolutely dominated and abused me and fuck it felt so good. They took turns with me, tossing me around, literally shoving me to each other and then they would grab the back of my head and force their dick down my throat. I couldnt even breathe honestly, it was so much, just one dick after another. I could feel myself trying not to throw up so bad and my dick was so incredibly hard, I could see the precum coming through my security pants.

    The biggest guy came first, someone pushed me over to him and I fell on my arms and knees. He stood in front of me and told me to get up and suck on daddy's dick like a good boygt. I did, I started sucking on it like crazy, it was so big it was stretching my mouth. I could hear the other guys jerking off or making noises in the background and it was so fucking hot. He grabbed my head with both his hands and started to thrust deep down my throat and asked me if I was hungry for daddy's cum. I mumbled and moaned with his dick stuffed down my throat and he started getting really loud yelling out fuck that feels so good and some other shit in spanish, it made the rest of the guys start laughing.

    He had his dick deep deep down my throat when he came, I could feel the cum traveling down his hole as it squirted against the back of my throat. It tasted amazing, it was stuck in the back of my throat. He took it out real slow and the he walked away. Before I could even catch my breath and rest, another guy stepped in front of me and was jerking his dick off viciously. He stood in front of me and started cumming almost immediately, a strand of it shot right onto my face but I instinctively placed my mouth right over the head and let the rest of it squirt into my mouth. I sucked on his head like crazy while he moaned out, he had a lot more cum than the 1st guy.

    While I was still sucking on the 2nd guy, 3rd guy came up from behind me and started to cum right on my face while guy 2's dick was still in my mouth. Some of his cum got on my hair, my eyes, my nose, and some of it got on guy 2's dick but I made sure to suck it clean. Guy 4 was no joke, he was a bit shorter than everyone but he had a mean curved fat dick. And he wasn't trying to cum real quick, he stepped up to me still on my knees covered in cum. I was so tired and exhausted by that point, I was pretty much slumped over by that point.

    He picked me up back onto my knees and straight away started fucking my mouth hard. All the way in, all the way out, making me gag on it. He was fucking my face hard like a pussy, slamming into my lips and nose over and over making a whack whack noise and me choking and gagging on him. A couple of guys left after like 5 minutes of him now having pushed me up against the wall and fucking my face. I could hear them talking to each other and the door opening and closing. He kept telling me things like, youre such a good slut, you're such a good little fgt, you're such a little bitch, take this dick bitch come on etc etc. I was so tired, i honestly wanted him to stop but I couldn't do anything, I just kept thinking oh god just let him use you, he's going to cum eventually.

    After some more really intense gagging and throating, guy 4 came all over my face even though I asked him to cum down my throat. He said he gets to decide where it goes lol whatever, I was so tired by that point, I didn't care. Guy 2 came back over to me, he never left, he was jerking his dick off again watching me and guy 4. He motioned me to come over to him on the couch while he was jerking off his dick. Guy 4 told me to be a good boy and go suck up guy 2's cum again. I was so tired but I listened. I crawled on my knees and hands to guy 2 as he jerked off faster and faster. I told him please please daddy sir please feed me, I want it so bad, im so hungry for daddy's cum. He yelled out really loud and blasted in my mouth again. He shoved it down my throat, pushing me down into his pubes as he came.

    I fell back after he sort of shoved me off of him. I was laying on my tile floor on my back just panting, exhausted with all this cum in my throat and on my head and face. Guy 4 walked over me and said something in spanish and laughed as he left. Guy 2 didn't say anything, he just put his gym shorts back on and walked out. They all left and I was just laying there, covered in cum. It was roughly 2:45 at that point so I only had 25 minutes before my girlfriend would come home.

    I laid there for about 15 minutes before I finally got up. All the cum was dried on me and I could still taste it in my mouth. I cleaned up the living room where they all used me and spray some febreeze. I brushed my teeth and used mouth wash before hopping in the shower. Girlfriend came home and asked me why the door was unlocked. My heart skipped for a second but I knew she didn't really know anything. I explained to her I simply forgot to lock it, whoops. She kissed me while I was in the shower and told me to not do that, its unsafe.

    I made tilapia and brown rice for dinner for us that night. While I was in the kitchen, I could feel my face and thighs were so sore ..(continue confession)

    0
    # 47386 - by Slutforbj / September 18, 2020
    - Dating Disasters -
    Straight Male / 26

    I Thought I Would Stop At 21. I Was Wrong

    I posted a confession here last week about how I have been letting guys (21 in total) fuck my mouth at my job behind my gfs back and how I was going to stop it because its wrong.

    I couldnt stop, i couldnt resist. I thought to myself, well, I'll just download grindr and look around, thats all. Not even going to upload a pic or profile, just gonna see what i see. A couple hours pass and I'm still looking around at all these guys on grindr looking for head. I was about to get off from work and was just killing time browsing and I told myself that once I got off, I would uninstall it. I thought since I was just looking, it would be fun if I teased. I wasn't getting much attention with just a blank profile.

    I uploaded a pic of me on my knees in my security uniform, mouth shaped like an O with my eyes cropped out. My profile said I was going for a dick to be shoved down my throat until he cums down my throat. Oh boy did my profile do a whole 180. In less than 20 minutes, over 100 guys had viewed me and about 30-40 guys were asking to come use my throat. Damn it had me hard as fuck at work, precumming in my pants like crazy looking at all the dick pics sent to me, imagining myself gagging on each one.

    It was time for me to get off work. And so many guys were hitting me up. I couldn't help myself. I couldn't resist. At first I told myself, it would just be one guy, it would just be real quick and fun. I messaged one guy while I was in my car about to leave when another guy with this beautiful dick messaged me. I told him to come over too if he was okay with having me suck both of or he could wait and watch. I reached out to the other guy and told him the same and they both said they were down. I started scrolling through my previous messages and looking at all the nice dicks. I messaged another 4 guys, 2 of them said they were down. I gave all 4 guys my address, gate code, and told them the door was unlocked.

    All 4 of them were Hispanic guys, all of them had some thick chubby latino dicks. The biggest guy was like 6'2" and 280lbs or something and my lord he had a huge dick. It wasn't as big as the bbc I've had but it was so surprising and plump. I loved it. They all absolutely dominated and abused me and fuck it felt so good. They took turns with me, tossing me around, literally shoving me to each other and then they would grab the back of my head and force their dick down my throat. I couldnt even breathe honestly, it was so much, just one dick after another. I could feel myself trying not to throw up so bad and my dick was so incredibly hard, I could see the precum coming through my security pants.

    The biggest guy came first, someone pushed me over to him and I fell on my arms and knees. He stood in front of me and told me to get up and suck on daddy's dick like a good faggot. I did, I started sucking on it like crazy, it was so big it was stretching my mouth. I could hear the other guys jerking off or making noises in the background and it was so fucking hot. He grabbed my head with both his hands and started to thrust deep down my throat and asked me if I was hungry for daddy's cum. I mumbled and moaned with his dick stuffed down my throat and he started getting really loud yelling out fuck that feels so good and some other shit in spanish, it made the rest of the guys start laughing.

    He had his dick deep deep down my throat when he came, I could feel the cum traveling down his hole as it squirted against the back of my throat. It tasted amazing, it was stuck in the back of my throat. He took it out real slow and the he walked away. Before I could even catch my breath and rest, another guy stepped in front of me and was jerking his dick off viciously. He stood in front of me and started cumming almost immediately, a strand of it shot right onto my face but I instinctively placed my mouth right over the head and let the rest of it squirt into my mouth. I sucked on his head like crazy while he moaned out, he had a lot more cum than the 1st guy.

    While I was still sucking on the 2nd guy, 3rd guy came up from behind me and started to cum right on my face while guy 2's dick was still in my mouth. Some of his cum got on my hair, my eyes, my nose, and some of it got on guy 2's dick but I made sure to suck it clean. Guy 4 was no joke, he was a bit shorter than everyone but he had a mean curved fat dick. And he wasn't trying to cum real quick, he stepped up to me still on my knees covered in cum. I was so tired and exhausted by that point, I was pretty much slumped over by that point.

    He picked me up back onto my knees and straight away started fucking my mouth hard. All the way in, all the way out, making me gag on it. He was fucking my face hard like a pussy, slamming into my lips and nose over and over making a whack whack noise and me choking and gagging on him. A couple of guys left after like 5 minutes of him now having pushed me up against the wall and fucking my face. I could hear them talking to each other and the door opening and closing. He kept telling me things like, youre such a good slut, you're such a good little faggot, you're such a little bitch, take this dick bitch come on etc etc. I was so tired, i honestly wanted him to stop but I couldn't do anything, I just kept thinking oh god just let him use you, he's going to cum eventually.

    After some more really intense gagging and throating, guy 4 came all over my face even though I asked him to cum down my throat. He said he gets to decide where it goes lol whatever, I was so tired by that point, I didn't care. Guy 2 came back over to me, he never left, he was jerking his dick off again watching me and guy 4. He motioned me to come over to him on the couch while he was jerking off his dick. Guy 4 told me to be a good boy and go suck up guy 2's cum again. I was so tired but I listened. I crawled on my knees and hands to guy 2 as he jerked off faster and faster. I told him please please daddy sir please feed me, I want it so bad, im so hungry for daddy's cum. He yelled out really loud and blasted in my mouth again. He shoved it down my throat, pushing me down into his pubes as he came.

    I fell back after he sort of shoved me off of him. I was laying on my tile floor on my back just panting, exhausted with all this cum in my throat and on my head and face. Guy 4 walked over me and said something in spanish and laughed as he left. Guy 2 didn't say anything, he just put his gym shorts back on and walked out. They all left and I was just laying there, covered in cum. It was roughly 2:45 at that point so I only had 25 minutes before my girlfriend would come home.

    I laid there for about 15 minutes before I finally got up. All the cum was dried on me and I could still taste it in my mouth. I cleaned up the living room where they all used me and spray some febreeze. I brushed my teeth and used mouth wash before hopping in the shower. Girlfriend came home and asked me why the door was unlocked. My heart skipped for a second but I knew she didn't really know anything. I explained to her I simply forgot to lock it, whoops. She kissed me while I was in the shower and told me to not do that, its unsafe.

    I made tilapia and brown rice for dinner for us that night. While I was in the kitchen, I could ..(continue confession)

    0
    # 47384 - by Slutforlatinocock / September 18, 2020
    • - Dating Disasters -
    Lesbian Female / 29

    I Am Afraid I Screwed Up An Unscrewing It Will Make It Worse

    I think I sent her the wrong signal. I know she is gay and we are friends with benefits. Her lease was coming up for renewal, I asked if she wanted to cut her rent expense she could room with me. It was purely a way to cut costs for her. She is upset that I showed her my second room, she guilted me into sharing the master with me, she is my friend and we play around, but the intent of my invitation never meant to be a commitment proposal.

    0
    # 47343 - by Leslie / September 14, 2020
    - Dating Disasters -
    Straight Male / 25

    This Stops Today. Probably.

    I've sucked off and swallowed 21 different guys while I've been with my girlfriend. Most of them came to my job where I work security at and met me in the stairwell where they would fuck my face until they came down my throat or they would jerk off and then stuff it in my mouth at the last minute. So many different types of dicks, uncut, cut, dark skin, light skin, black guys, white guys, Latino guys, Indian guys, Asian guys. Thick dick, long dick, small dick, average dick, bent dick, old dick, 18 year old dick, bbc dick. Tranny dick too. Each one of them I've swallowed. And I was an extra good boy every time, I loved every single drop of cum that was given to me. I'm still such a good boy I promise I want all the daddies and tgirls to use me but I am in a relationship and it's supposed to be exclusive. Im breaking these rules and its unfair and cruel to my partner. 21 different dicks. That's enough man. That's plenty enough. There's literally no need to keep hurting her like this. Stop now. You've had plenty. Ease up a bit and stop trying to be such a slut.


    1. Fat black guy 1 thick fat cock, visiting houston, fucked my face in his car until he came.
    2. Fat black guy 2 avg dick, real bumpy feeling, laid me flat out on the stairs and humped the shit of my face until he came down my throat deep. His big ol belly was suffocating me the whole time he was Cumming, I thought i was gonna pass out
    3. Fat black guy 3 dreads and nice dick, also fucked my face in his car until he came
    4. Fat black guy 4 thick head, thick dick but short, fucked my face on his bed in his room while watching Netflix. First he let me suck on the head and balls for like 15 minutes while I dry humped his bed. Then I convinced him to get up and fuck my face. He did it while his roommates and landlord was home, he was really noisy. He grabbed me by the back of my head and fucked my throat hard, his belly was suffocating me like the other fat guy I sucked. He came a whole bunch, it took me 3 swallows with his dick in my mouth. He let me jerk off and cum all over my uniform while he was fycking my mouth too.
    5. Fat black guy 5 dreads avg dick, uncut, sat down and let me suck him off in the stairwell, used hand and mouth combo. Yummy cum.
    6. Indian guy avg dick, kind of small, fucked my throat in his nice car until he came.
    7. Hispanic uncut guy (glasses), thick dick, very pinkish head, thick foreskin. Fucked my face in the stairwell, only forced like half of it and took it out, jerked off fast and then stick it back in until he came. Huge load. Got up my nose. Let his heavy dick rest on top of my face while telling him thank you.
    8. Hispanic poppers guy, lives at arlo next door, super bottom slut, skinny long dick, he just felt like getting his dick sucked while getting the mail lol
    9. Hispanic dark skin skinny guy, avg dick, finished sucking him, he wanted me to cum too so he fucked my face until I jerked off
    10. White older guy, fucked my face super hard, made my lips sore and my nose hurt like someone beat me up. Thick uncut dick, avg size. Fucked my throat until he came, he did half on my face, glasses, and shirt. Came over a 2nd time and he told me he had just finished creaming his wife before he fucked my face really hard again, wasn't as hard as the 1st and I could taste his wife's pussy. Came all down my throat the second time. I let his heavy thick dick rest on my face while i told him thank you sir over and over again.. He hosted me in his garage while his wife was home. I came in my pants the first time and went home and jerked off thinking about it like 3 more times within an hour.
    11. White dude used to work here, shorter foreign guy, really nice, avg dick, came very quickly for me while I was on my knees, I swallowed him up nice
    12. Hispanic guy bent dick, parked at Millennium tower first by accident, almost got caught by Jim. Had him come back by later and he fucked my throat in his car at first but his dick was angled weird so we went to the stairwell instead. He really came deep deep like his dick was all the way in, I was breathing in his public hair and I could feel his dick pulsing down my throat.
    13. 18 year old Hispanic guy, huge long dick, uncut, filmed me jerking him off and attempting to suck it but it was waaay too big for me. Couldn't make him cum.
    14. Fit good smile black guy, sucked him while another black guy watched, he was so handsome and had such a nice smile, he fucked my face with my hand there too, he came but it was quick and wasn't a whole lot.
    15. Chubby but not fat black guy dick got soft, he was first out of 2 guys, he had a nice chubby dick but couldn't keep it hard for whatever reason, maybe pressure
    16. Fit older black guy dick got soft, almost got caught by Jim again, started sucking him but he got soft a few minutes into it so we stopped early.
    17. Latina tranny, went to her apartment, paid her 70 to fuck my face until she came. She had a long dark skin dick, thick but not too thick. Super thick accent, super thick ass, jerked herself off until I swallowed her cum.
    18. Old short small Asian guy, almost got caught by Jim and Mr Hight! Came back a couple of hours later, fucked my face and hand with his tiny little dick and came a lot, tasted really really not good, got all in my teeth too. He was extra happy lol
    19. Older Fat black guy, retired marine, super fat stubby dick, really pink head. He liked grabbing my asshole a lot even though it was smelly. He jerked off until he came in my mouth.
    20. Fat black guy 7 came over to my place from the metro stop, fucked my face for a little bit in the living room, then laid down on my bed and let me finish him with my hand mouth combo. Avg dick, nothing special.
    21. Muscular black BBC guy with Tina, invited me over to his hotel room at the Marriott, level 12. He smoked Tina naked with his huge massive BBC hanging out. He laid down on the bed and started to get it hard and then I sucked on it for a while. It was huge like at least 10 or 11 inches and THICK like insanely thick. Couldn't close my hand around it, thats how thick. I asked him to stand up on the bed and fuck my face but he wasn't really into it. At one point, I almost threw up and he said he felt bad lol. We laid back down and jerked each other off. He came like an eruption and just ropes of cum. He came like 3 or 4 different ropes of cum all over my arm and stomach, it was so sticky gooey and warm. I immediately went to lick it all up and put it in my mouth. As soon as I finished cleaning him off, he started jerking me off until I came a bunch too. It was 1 huge big burst of cum that got all on my chest and stomach. He went and licked it all off me too. He really seemed to enjoy it.

    0
    # 47310 - by Slutforbj / September 11, 2020
    • - Dating Disasters -
    Straight Female / 23

    Sorority Party

    Party Bus. The end of the school year, time for fun. The bus was to basically just ride up and down the freeways while kids got drunk. Some girls took their tops off, other girls had their tops torn off. Scores were given, A+ to D, I got a D. Pants were pulled down, some pulled their pants down. Lean forward across the back of the seat in front of you with a blindfold and a guy's dick is shoved up your vagina if your lucky, up you're ass if you're not.

    Next morning you have a hang over, puked in the bed. Wondering who fucked you last night.

    0
    # 47242 - by Flat Chested / September 7, 2020
    - Dating Disasters -
    Bi-Sexual Female / 28

    He Is Boring Us

    I am bored. For the last two years I have shared a flat with my boyfriend's ex. A money thing, three's a party, hot sex with her, she opened me up to sharing is caring, and two hot mamas are even better. The thing he is boring now.

    Our day, crawl in bed after breakfast, make love, take a shower, clean the flat, agree on lunch, go for a walk, nap together, make love some more, do a crossword, fix dinner, go to bed, make love.

    Or he calls, comes over, takes his pick, walks her back to the bed, fucks her till he is done, sends her out to get a hot towel, gets dressed, leaves. Boring useless sex, no party time, just a hole to masturbate in.

    0
    # 47129 - by Sarah / August 29, 2020
    - Dating Disasters -
    Straight Female / 19

    I Just Got Let Down

    Hi my name is Kathy, I live in a small town in rural upstate New York. I am one of seven children, the oldest, two boys and five girls. We live in the farm house of my great grandparents, two upstairs bedrooms, one indoor bathroom. My father is the custodian of the junior high school, my mother with seven children doesn't work outside the home. By any measures we are poor.

    I left home after high school and got a job in Syracuse at a Hilton hotel. I met a man, he is 34 with a trust fund, he doesn't need to work and he took me on a holiday to Orlando and Disney World after I told him I had always wanted to go. The sex was blah.

    I don't have experience, there is nowhere to go in my town and everyone knows everyone. I was so disappointed, I always fantasized on heavy metal music and fireworks. My first time was so disappointing.

    That's my confession.

    1
    # 47088 - by Kathy / August 26, 2020
    - Dating Disasters -
    Straight Female / 45

    Looking To Move On As Usual

    I need sex. I am so fed up trying to find the right partner and things not working out. I have to keep trying to find one that is right. It takes time and work. It means also a willingness to leave the past ones behind you, which I am doing. Just preferring new romantic goals and men in my life and letting go of the past ones is not that hard.

    2
    # 47054 - by Can only see future only / August 24, 2020
    • - Dating Disasters -
    Straight Female / 21

    Confused About My Feelings

    Still not over 2019 Spring Break in Cabo. I am a senior at Arizona State this fall, online, at home until I can go to campus. I met a guy in Cabo from the University of Michigan. Things went down the loosing your self respect road and I had sex with him and another girl. I regret having sex with him, I insisted on a condom but he took it off. I got an abortion, never told him about it, went on with my life, keeping in touch with Ellen who was the girl that night.

    She is pretty level headed, held my hand during the abortion thing, and is now my best friend. She is asking me to transfer to her school. I only had sex with her that one time, my only experience like that. She claims to be bi, but says for me she will stay far away from any guy. I don't want to toy with her, I just don't know if one drunk night is a commitment.

    Am I, or am I am not?

    1
    # 47007 - by Tory / August 20, 2020
    500 of 75,765 Confessions Displayed.

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