We've all had them - those truly hateful embarrassing moments, caught with your finger up your nose, or snooping through a medicine cabinet, sneezing snot all over a fellow passenger, or realizing you forgot to set the parking brake after your car rolls into a gully, or needing to wrap your jacket around your waist when your period unexpectedly started when you were wearing white pants. This is the place to chronicle those most embarrassing moments so we can laugh at it together. Let the whole world know your bad habits and when you got caught committing them.

Worst Day Ever

When I was a 14 yr old boy I lived in a very rural place. Only a few of us kids lived out this far and the bus ride was long and early. There was a girl my age and we liked each other. We started playing around a little. One morning on the bus there were only like 4 kids. Me and her were sitting in a seat together in the back. She unzipped her pants and let me finger her. I unzipped my pants and took out my dick. She started giving me a handjob. I couldn't help it I started cumming. I shot my cum straight up, all the way up to my neck and all over my shirt. I had cum all over me. And in a few minutes the bus was going to start picking up more kids. I had nothing to clean myself up with. Trying to wipe it of only smeared it. I caught hell all day long!

  • Riding Bareback With My Cousin

    My grandparents had a farm in the foothills of the Blue Ridge in Virginia. It was a paradise for city kids to spend summer vacations. Horseback riding, fishing and canoeing. Almost like a summer camp all to our selves.

    When I was 14 my cousin Celeste, who was in her first year of college came to stay a week or so with the grandparents. One morning she was getting her horse out of the stall. I went out to hang around and check her out. To me, she was about the hottest girl I knew and I used to follow her around like a puppy. She was a tall, slim blonde, played sports and had pointy boobs and never wore a bra around the farm.

    We made small talk for a moment and she asked me if I wanted to ride up into the forest with her. I jumped at the chance. We were riding bareback and I had my arms on her hips. As the horse walked along slowly and we rocked back and forth, I started getting a boner as my young cock was bumping against her butt. When we went down to cross a ditch, she told me to hold on and I wrapped my arms around her waist.

    When the horse went back up the bank and the trail leveled out, I kept my arms around her waist. I couldn't holdout and longer and I buried my forehead in her back and twitched several times as I shot a load of cum in my cut off jeans

    When we stopped at a spring to let the horse drink she noticed the big wet spot in my shorts. "Is that what I think it is" she laughed. Then she said " I thought I could feel something going on behind me" as she smiled at me.

    To my shock and surprised, she took off her T shirt and dipped it in the water exposing those boobs I had been dying to see. She was wiping her face and chest with the cool wet shirt and her nipples got rock hard. She said I should clean myself up before we got back and Grandma saw the stain in my shorts.

    "Just pull them down and dip them in the water, Now don't tell me you're bashful or something" she grinned. I slid my shorts off, dipped them in the water and began to wipe myself off. I had my back turned slightly and she told me to turn around. She wanted to know if it was as big as it felt. As I wiped my cock and balls with the wet shorts. I began to get hard again.

    She took my cock in her hand and smiled as she said " Look at you Tony, all grown up and everything" as she stroked my hard cock, jiggling it around. "How old are you now"? she grinned. She kept playing with my cock and I fondled her boobs until I tensed up and shot another load of cum.

    Two days later after breakfast Granny asked Celeste what she had planned and she told Granny she was gonna go for another ride up to the spring. Then very causally, she asked me if I wanted to tag along. I got my first piece of pussy that day, riding it bareback. Tony.

    Unexpected

    I was in my early 20's at the time and over at my girlfriend's mother's home. My girlfriend was working late and her mother and I were chatting in the kitchen preparing some snacks for her when she came home. I had been over often and enjoyed her mom's hospitality. Her mother accidentally spilled some chocolate sauce over the crotch of my pants. She felt bad and without thinking started using a wet cloth to wipe off the stain. Her wiping gave me an erection which I tried to hide by wriggling away in embarrassment. She was a blonde big breasted 50 yr old and feeling her so close made it feel so intimate. She then suggested I take off my pants so she could wash them. I was so flustered I pulled them down and my hard cock popped out of my underwear. She gasped and said poor boy what have I done ? She then went down on her knees and took my cock in her mouth. I was so aroused a few sucks on my cock and I exploded in her mouth. She took it all and gulped it down. She smiled at me and said everything is better now as she took my pants to the wash. I ended up wearing a spare pair of jogging pants I had left there previously.

  • Boating Fun

    I was invited out this weekend on a friend of a friends boat. I’m a small petite girl C cup boobs and a fit tight ass. Plain and simple I got a little wasted and ended up letting 2 guys not at the same time fuck me. One when we got to our camp site and the other on his boat late at night. The fucked up part was as i was getting fucked on the boat the first guy caught us and told people at the camp site. There I am on all 3s on the bow getting absolutely plowed when lights where out on us and a crowd of like 20 people where cheering us on. I was so embarrassed because I was in the middle of an intense orgasm getting absolutely drilled and the guy that was plowing me did not stop. I sat there getting plowed for what seemed like forever while he finished. When he did he shot the up my back hitting the back of my head. I was completely naked fucked with cum on the back of my head. I was so embarrassed i jumped in the lake to wash off came up and a friend gave me a towel. I spent the next couple of days trying to keep people off me. I did not drink the rest of the weekend mostly because every guy there was constantly trying to fuck me. I left a day early as it was clear that I was fair game.

    Walked In On The Grandparents.

    My Mom gave me a bag of clothes to drop off at my grandparents' house for a church rummage sale. When I went in, the house was quiet and as I walked down the hall I heard the grandparents in their bedroom. Grandpa was saying " don't stop, don't stop".

    I was shocked but knew what was going on. I stood still and peeked around the corner, grandpa was laying back and grandma was sucking his dick. When she pulled his dick out of her mouth, it was a thick but stubby thing ,maybe only 4 inches long ! She was stroking it using only two fingers before going down on him again. I couldn't believe my eyes, they were both in their 70s.

    I slipped back out and left the bag of clothes on the front porch. I giggled all the way home.

  • My Cousin And I Had Our First Live Sex Show When We Were 13

    Me and my cousin were thirteen at the time. We lived in a small farming town and every year the fair came to town and it was the summer event. That year we got permission to go alone, but be home before dark. We rode every ride, talked to friends, ate hot dogs. When it was time to go home we decided to walk across the vacant lot to our street. We caught this couple having sex in the grass.

    My cousin first saw them, his naked ass rising and falling, and we snuck up quietly and there was a girl under him. We watched and it was the girl that worked at the bank. Her legs open, and she was naked under him, when he pushed up her boobs were visible and when he went up and down we could see his dick when he pulled it out and pushed it back in. We were as quiet as a church mouse, completely enthralled by the scene being acted out in front of us.

    This man crawled down between us, he was the town part time policeman and he taught school at the high school. He whispered, 'What may I ask are you two girls doing here?' You can't really understand just how embarrassed we were. He had us crawl back quietly and disappear and go home. Nothing to see there,

    It was bedtime and my mother came in to ask me how it had gone at the fair. Was everything all right? Sure, I told her who we saw and that we had a hot dog. 'No that's not what I'm talking about'. What had I seen. It took about a minute before she told me that she had received a call from Mr. Thompson, and he had suggested it was time for her and me to talk about the birds and the bees. Now, just what had I seen.

    I didn't sleep that night, I was sure I was going to hell. I had to agree to confess and I was sure that I was going to get more than a Hail Mary. My cousin told me pretty much the same thing, except her mother went into detail about what a girl did in those instances, and not to be surprised if she liked it. As to the girl, not to mention her name anywhere, those secrets had to be kept. The guy we guessed worked with the carnival.

    It would be many years later before I lay naked with my legs around a guy, who wanted 'tits' when he had sex with me. But I remembered that girl, out there in the grass, I still remember her and all these years we have kept her name a secret.

    Caught Self Pleasuring Front And Back.

    This was back in 2020. I was staying at my parents house because my dad was in the hospital and my mom needed someone to watch the dog during the day when she was at work.

    I’m able to remote work so it worked out perfect. But sadly my girlfriend couldn’t remote work so she couldn’t tag along. That meant no sex for a few weeks.

    So obviously no sex had me really horny. I like to masturbate so I was fine rubbing a load out in the afternoon or before bed.

    At the time my girlfriend was big into pegging. I let her try it on me and after a few times I actually enjoyed doing it. So when I packed some stuff to stay at my parents my girlfriend put a dildo in my bag as a joke.

    After 5 days at my parents house I actually kinda started to miss getting pegged. Never thought as a straight guy I’d enjoy getting my butt fucked by my girlfriend but I did.

    So I got naked. Laid a towel on my bed. Put on some porn on my iPad and put my AirPods in. My mom wasn’t home. I lubed up and stuck the dildo in my butt. First time I had ever done that myself so it was fun.

    I was fucking my butt with the dildo. My dick was very hard and leaking precum. Next thing I know my mom is looking right at me. I didn’t know she had gotten home and she was a bit confused at what she was seeing till it dawned on her I was masturbating with a dildo in my butt.

    She walked away real quick.

    Unexpected, Unplanned, And Now I'm Pregnant

    Following a night out with the girls I got home a bit drunk. I fell asleep and didn't hear him come in. I had given him a key, but forgot about it. Waking me up like that gave me a heart attack.

    I want to remind you, if you give a guy a key, make sure you set boundaries. It is not for his use when he wants. At least from my perspective. I was not prepared, he didn't use a condom, I am now sitting with the confirmation from the clinic.

    Multiple Fingers Up My Butt.

    Recently I went to my doctor whose practice is at a teaching hospital in Gainesville. During my physical, the doctor did a DRE, (digital rectal exam) checking for an enlarged prostate. I had that exam done before maybe 5 years earlier and I knew what to expect.

    Only this time the doctor had two medical students with him, one young man and a young woman. He asked me if I was ok with him demonstrating and explaining the technique to the students. I had known my doctor for years and I consented.

    The doctor lubed up his gloved finger and inserted it all the while talking to the students and telling them what to feel for. He was in there a long time before then asking the male student to try it. The guy did the same thing inserting his lubed finger and feeling around.

    After the guy went, the young woman did the procedure, She was in there a long time too, massaging around. The doctor kept asking her if she felt the prostate and she told him she had found it.

    When they finished, my doctor thanked me for my cooperation and patted me on the shoulder and told me to get dressed. It was all I could do to hide my swelling cock poking out under the gown. Best physical ever !

  • Man I Hope He Doesn’t Say Anything

    So I have been teaching 6th grade at a school for about two years. Im Hispanic short lang dark hair small boobs b cup but have very curvy hips and a nice plump ass. Nothing crazy has ever happened at school I hear a few of the boys make comments to each other about my rear end. I let it go no since it’s not dirty or directed at me.
    I have had some dads make comments and even ask me out but I never accepted there advances until one dad in particular was super friendly. His son was in my class and was recently divorced. I actually met both parents and he was nice and his ex was a total rag. It was an open house and he spent a lot of time chatting me up.
    Fast forward a few weeks and a few of the other teachers wanted to grab a drink after school on a Friday at a brewery that is 5 minutes from the school. We had been there a bit again I am not seeing anyone in particular when we where about to leave an in comes this dad. Stops after seeing me and we talk a bit. He buys me a drink without me saying anything and I start talking about him and myself we are really getting into each other. It really helped that he was a tall dark handsome type muscular guy. Well we talked for a bit and i did something that I don’t normally do and left my car there and hitched a ride with him. We went back to place where well I got fucked like a rag doll. Completely fucked well fucked roughly fucked. He licked me in my rear and my pussy I sucked and swallowed he pounded me into his bed like he owned me. Truth be told I felt like he owned me as whatever he wanted to do to me I went with it. I had only tried anal a couple of times and to be honest I had never really let anyone do more then a few pumps before stopping them. Nope not this guy he put me on all 4s put some lube on his fingers and proceeded to rub my tight little hole slipping his fingers into my pussy and ass. I then felt him grab my hips he was slapping my ass really hard I got into it as he kept asking me who was a bad girl and still smacking my ass to the point that his hand print was on my ass cheek. He gripped my hips and pushed his head pass my tight ring and with a little more oil he went to town. He had me toy my clit as he reeked my ass it went from pain to a good pain to a sudden urge to pushing and and all of sudden with him deep in my ass I squirted all over the bed. Never missing a beat he pounded me again into the bed. I fell on my stomach and he had me spread my cheeks as he fucked me like a piece of meat.
    We finally passed out and the next thing I remember was looking around to see where I was at. I was sleeping well I was sore the sheets where till wet and I could see where there had been someone else sleeping in the bed. I went into the bathroom and looked at my self in the mirror. I was a mess I was extremely sore but felt good. I washed my face I had dry something on the edges of my mouth could have been cum. My pussy hairs were also crusty as well as my undies. I put on my jeans put the panties in my purse did the best to fix my makeup and I headed down stairs. As I came down I should have just left and no one would have seen me. But I felt I needed to say goodbye and walked into the kitchen no really thinking this through there was the man that had just fucked me like a cave man and was talking to his son my 6th grader. Totally awkward quite I said good bye and see you Monday I turned to walk out when he caught me in the drive way I was so red and embarrassed. He said that he let me sleep in it was near 11 and his ex dropped off his son at around 10:30. He let me sleep and was going to wake me shortly but I had beat him downstairs. His son was heading over to baseball practice and left shortly while we talked in the driveway.
    We hooked up a few more times but he was just to rough and it was really weird to see his son in my class after that morning. The remarks got bolder and some got handsy. I left the school after that year. I have done my best to avoid dads but sometimes it’s very hard. If anything good came from this is I really learned to enjoy anal. I found that I like my hair pulled and my ass slammed at the same time.