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.

First Time Ever Getting Caught Jerking Myself Off

I’ve went all my teenage and adult life never getting caught jerking off. Lucky I guess but it saved me the embarrassment. Till now..

Last week I was at home as usual on a Saturday afternoon. I hadn’t done much all morning so by noon I was ready to jerk off then I had to go a few places.

So I’m sitting on my couch in just a shirt and underwear. I pull up some porn on my phone and pull my dick put the fly of my briefs.

It’s a cold day out in Colorado so my curtains were shut.

I’m playing around with my foreskin at first and once I’m fully hard I start to jerk off.

Mid ways into jerking I hear my back door open. And anyone who wears tighty whities knows you can’t just pull your hard dick back in through the fly quick.

So as I stand up with my hard dick out the fly of my briefs I made eye contact with my aunt! She ended up coming over earlier then expected and walked in on me masturbating

So I finally get my dick back in my briefs and push my foreskin back over my head. Lost for words I said I didn’t expect you so soon and in response she said I know I’m early and didn’t even think to knock

I told her I need to shower. So I went into my bedroom and blew a huge load all over my briefs

The rest of the day I felt really awkward

  • I Had No Idea

    I went out a Friday night with some buddies hit the bars around 5 a few weeks ago. After about an hour a group of guys and women walked in. One of the ladies there was our close friends mom. She is good looking married would never cheat but it would be fun to try. We joined them we flirted we had drinks and I got to talking to this one lady who had dark hair a hard body she was probably in her 40s. She was a looker for sure and as the night went on we talked more and more and I eventually convinced her to come home with me. Her phone was blowing up she was ignoring it she said she was divorced and it was her sister calling her. I found out her name was Liz. We got to my place and I got sucked off and eventually railed her a few times. It was skate and we ended up passing out. The next morning we woke up and before she left she wanted to shower and that turned into another 2 rounds. About 10 she is getting ready to leave her phone had died and we get a knock at the door. It’s my buddy whose mom we had run into the night before. I open the door he says bro wtf are you guys doing. Not sure what he means in walks Liz half dressed and my buddy says aunt Liz WTF. I was like what Aunt Liz ? Apparently she was in town for the week and her sister my buddies mom had planned for dinner and hanging out that night. Apparently I ruined those plans. She left and we saw each other a few more times while she was here for that week. When she left i honestly missed her and we kept touch and we agreed to visit each other. Her sister my buddies mom at first seemed a bit jealous since we always seems to flirt. I joked with her that I really wanted her and not her sister one time a short time after this went down. A day later she came by my place in an outfit that I had no idea she owned. I really tied to not get caught up in this but when a women says I enjoy anal can you help me with this plug. I caved and have been fucking my good friends mom and am visiting her sister this coming week. To be honest Liz is the better fuck but her sister is way dirtier with a nice fat ass. One is married the other is not. It’s just a fun fling so il roll with it

    Impulse

    I was at a swingers party about eight years ago. The atmosphere was electric and my arousal matching the atmosphere. The venue was a very large posh house in the country and somehow I got an invite. Curiosity lead me from room to room pausing to watch all manor of sexual activity. In one of the rooms there were two black guys fucking the hell out of a white married woman and on a chair her husband totally naked wanking. I felt total hedonism engulf my body. The guys were using her in every way but my gaze kept going back to the cuckold. His pace was increasing, his chest heaving and his cock was hard with his purple gland exposed. I was transfixed by his endurance but he was weakening and his hand a blur. I could see he was about to cum and then it happened. I rushed across the room dropped to my knees and before reason hit me I had a mouth full of cock, not any cock but an ejaculating cock. Spunk hit the back of my throat making me gag but I managed to swallow his load. I sucked hard as I pulled my mouth away removing any remaining jizz. I was stunned at what I'd done and humiliation was soon to follow as I realised everyone had stopped and was starring at me, the cock sucker. I got up and apologized leaving the room. I don't know why I did it I don't class myself gay it was just an impulse. There, it's out there I guess you can't unsuck a cock, it'll be with me for ever.

  • The Hunter And His Prey And How He Caught Me

    The male in this story was known to me. He exhibited sexual desire around me. I fended him off again and again, repeatedly telling him I was not interested. However, we were at a swimming pool party when I got too close and he struck. Half second timing, I was in his grasp. And he wasn't going to release me. I struggled as he held me tight against him. His hand moved down my back and grabbed my ass cheek as he started kissing me. Then to my complete surprise he got his hand inside my bikini. With a strong kiss his middle finger found my butthole.

    Now I'll be honest that was embarrassing.

    But, once your butts been fingered your all his. And that is my confession.

    Wedgies Get Me

    When I was younger, my older sister and her friend used to mess with me pretty bad. One time they gave me an atomic wedgie over a door and left me hanging for maybe 10 minutes. A couple years ago flashbacks of it kept going through my mind for some reason, and it made me want to recreate the scene to see if it would make me feel young again or give me closure or something…idk , what I was looking for.

    I set up a chair and a rig over my bedroom door to give myself a self wedgie, I slowly hung down and then kicked the chair out of the way so I was dangling just by my boxer briefs, but this time it felt different. While waiting for my underwear to rip, I started getting turned on and it kinda confused me , so I squirmed to help them rip faster but I ended up ejaculating right then and there into my underwear. Embarrassed as hell, I finally got the underwear to rip and ran to the bathroom to take a shower…as embarrassing as it was, I sorta liked it.

    Another month or so later, I was taking a nap and I woke up with a hard on, so I hurried to set up the rig, and before I could even kick the chair out of the way completely I was cumming in my briefs again. This time I tried not to move so I’d stay up on the door in my cum filled underwear, trying to see if I could get hard and cum again. After a while I got down (without ripping the underwear too much) so I pulled my underwear out to see the mess I made and then gave myself a standing self wedgie until I got hard again. This time I squat down into the wedgie and came again, filling my underwear even more, and the whole front of them was wet and sticky.

    I haven’t nut in a wedgie in a while but writing this is making me want to do it again…maybe in panties this time?

  • Dermatology Visit

    Since turning 50, I've taken extra precautions regarding my health. I have been going to the gym 3 or 4 days a for 18 years, so physically I'm in great shape. Recently I decided to have a dermatology scan to make sure none of my sun damaged skin. I just randomly picked on dermatology in a nearby city.

    When the assistant came in, she was a little bit overweight, but very attractive . I explained that i just wanted checked for any sun damage. She directed.me to leave my shorts on, and tske everyrhing else off. I did. When the nurse practitioner came in she was about mod 30s, very attractive. She started looking me over, and she took both hands and rubbed my chest and down my abs. It seemed more like I'd expect my wife to rub me, but whatever. She looked at my arms and shoulders and said "You look great." And then she asked me to stand on the step up to the table and turn to let her see my back. "Do care if I check your backside?" And i said "no" and she asked me to pull my shorts down. So I did, and she also grabbed them and pulled them down further - to the point my cock flipped completely out of my shorts. She couldn't see it but her assistant sure could (and did). I was thinking "Is this a head to toe visit? Why would she want to see my backside, it isn't exposed to the sun ever?"

    Then she said, "Can I get you to face me?" I turned around with my cock fully exposed. She pulled my shorts down another 3 or 4 inches exposing my balls. Her face was literally 3 feet away. Shw looked me over for a minute, then told me I could get dressed and she didn't see anything to worry about. She then noticed my ball cap had a football team name. The school her kids go to hired the coach from the team logo on my ball cap. We had a 5 minute conversation about the football coach.

    Sister In Law Caught Me.

    I have a gorgeous wife and her younger sister Keli is equally gorgeous. I've always wanted to see her naked because she has come amazing tits. But I never expected she would see me.

    One morning my wife texted me that Keli was going to stop by the house to borrow a dress. She didn't say what time she'd be by and I had to drop off my truck at a friend's house that does mechanic work . I figured I'd be gone for several hours and thought I'd miss her, so my wife had told her where the hidden key was to our back door. The truck was going to need parts that had to be shipped, so i had to leave my truck and my friend brought me home.

    I figured Keli had come and gone gone by the time I got home. I had a few hours and decided to look at a little porn and pleasure myself. I had a full erection with some lub and enjoying myself. I'm not overly huge or anything, but I am about 7 inches fully hard. I was completely shocked when Keli came walking through our bedroom door. Probably not near as shocked as she was!!!

    "OH MY GOSH! What are you doing? Are you crazy?" She just stood there looking at me for about 10 seconds. I was frozen. I didn't know what to say. She walked out and said "Im sorry. I Just came to borrow a dress! Just let me know when you're finished and I can come back in."

    I said "okay" and got up to grab my shorts. The second my feet hit the floor, she stuck her head back in and said "I didn't mean to inurruot you!" She was looking at my cock and I realized she just wanted to get a better look.

    "I'm not telling Cindy or Barry (our spouses). They'd both flip out. " She started fanning herself with her had and said "kind of like I am right now. If you want to finish, I'll step out." She walked out a second time. My cock became as.hard as.it has ever been, so I laid back down and knew it wouldn't take long. It was hot knowing she'd seen me and seemed okay. And having the door open with her just outside made it even more hot. It wasn't probably 3 or 4 minutes and I felt like I'd explode. She was listening and stuck her head back in and watched me until I came. I shot my load and it seemed like it went 3 feet high before landinf on my stomach.. "I've never watched a guy have an orgasim. Dang. I'm not going to be able to pick a dress now."

    I got up and wiped off. We spent the next hour talking about masterbastion, how often I did it, how often she did, what we thought about when we do it, has our spouses watched, etc.

    Before she left she admitted she would be doing it when she got home, but swore to never tell another soul. I told her she owed me one and she said "We'll see."

    Walked Right In And Caught Us

    I was at a Halloween party Saturday night with buddies. There was a shit ton of people. Almost all women where in there super slutty costumes. Looking hot has hell there was this little shorty Latina dancing with her friends. I followed then until she was off the floor and we ended up talking while grabbing some drinks. She was in this little pirates outfit black top tits popping out short skirt that covered almost nothing. We both had a few and had been talking for a while. Her friends would come by and try and get her to come dance but she was talking to me. I was dressed as Romes Cesar. I’m in good shape and like to show off my body seems to help when we have parties like this. She was short maybe 5 foot 2 nice rack but I couldn’t help notice her ass and how big it was for her size. Tiny waist big hips and ass I was obsessed with her. We danced a bit and I was able to grab onto her hips and she would rub her ass on me. More drinks come from buddies and now she is really grinding away. My really close friend threw the party so I knew the layout of the house. There’s a game room that was off limits so I slowly pulled her towards that easy and once we got inside the room i immediately started to kiss her and she kissed back. I had her up against the pool table and in an instant I had my cock out and she was bent over the pool table barely being able to stay on the ground because of how short she was. She had on a tiny red g string that covered nothing. I had no rubbers so Bare back I went it felt good i pounded away and squeezed her ass cheeks she lifted up to kiss me and kept doing so all the while keeping my cock inside her. I slid my finger in her ass and she said nothing so I pulled out and pushed in and it was a little slow going at first and by the time she realized where I was I had bottomed out and she had her hand on her puss rubbing it as I now pounded her ass. It was very tight and I was close to blowing my load. She lifted herself up and we where kissing and she was close to my face and as she started to cum the door to the game room opened she starts to cum I’m blowing my load as well and I hear Sophia what the fuck are you doing. We looked up as some dude had his hands in the air and storms out with a bunch of people with him. Apparently Sophia is her name and she is still letting me finish cumming. She adjusted her panties gave me a kiss and handed me her phone and put your number in it. I did so she called my phone and said that’s mine. I might come find you I might have to leave is all she said. I and and cleaned my cock up then found my buddy. I grabbed a drink and got filled in to where they went. Thought hey had left about an hour later he comes Sophia apologized and hung with me for the rest of the night. She ended up telling me that it was her soon to be ex husband. Apparently she had found out he was cheating and she wanted payback. I was the luck guy she went with. She was actually very chill and ended up spending the night together. We have seen each other a few times since then and we are constantly texting and talking. As a matter of fact she will be going to the Yankees game with me tonight. We shall see how this works out lol

    The Halloween Party From Hell Part 2

    Then the Ecto-One siren could be heard and the Ecto One arrived and The Ghostbusters theme played and Steven came charging at them yelling for both Finn Wolfhard and Logan Kim to come out and fight.

    Then some people wearing Ghostbusters Jumpsuits and Slimer Masks ppeared as Steven attempted to hit them with VHS Tapes but the Ghostbusters dodged every attack.

    Meanwhile I heard my phone rang and it ws Ghostface asking what my feet smell like.

    I told Fred to get out of my bathroom and then he has me turn on the tv and in the tv there's shit exploded all over the bathroom as well as pudding and I went inside the bathroom and it was like a nuclear explosion of shit and puding all over the bathroom.

    Then Ghostface puts his nasty bare foot in my face and I start running towards the stairs as I threw a vase at him, than a bicycle, than my mother, and finally pushed a piano down the stairs causing Ghostface to run down the stairs and the Piano hit the Ecto One.

    Finn and Logan got distracted and The Videomaster hit both Finn Wolfhard and Logan Kim in the head with VHS Tapes and shouted He HIT THEM WITH VIDEOS, HE HIT THEM WITH VIDEOS.

    Fred returned to the party wearing a american flg doo raga t***p thong, and red white and blue feather boas and began to sing the lyrics to Hulk Hogan's Real American theme

    Then he picked pu his feet and started smelling them and then started hulking up because whatcha gonna do when Feetamania runs wild on you?

    I then hit Drunk Hogan in the head with a VHS Tape and yelled HE HIT HIM WITH A VIDEO HE HIT HIM WITH A VIDEO as Fred fell into the Pudding pool and before you know it a food fight broke out along woth pudding and turds were thrown.

    Also some weirdo took both Finn Wolfhard and Logan Kim shoes off and sniffed their socks while they were uncoscious after they both got hit unconsious with VHS Tapes and then he ran off with thir shoes leaving Finn and Logan to leave the party in their socks.

    NightWolf stood on top of the Table to say Flawless Victory before Scorpion pulled hiis spear and yelled GET OVER HERE and pulled Nightwolf and hit him with an Uppercut and then Sub-Zero showed up as the two engaged in a live action Mortal Kombat Fight in my Living Room until the VideoMaster peforme his Fatality of hitting the 3 of them with VHS Tapes yelling HE HIT HIM WITH A VIDEO.

    The VideoMaster than got inside the Ecto One and drove off with it leaving chaos in the wake making this The Halloween Party from Hell or you can call it Helloween.

  • It Can't Be Real?

    I am a young female teacher in an "alternative" classroom. That means I teach students in the evening that have been kicked out of regular classrooms. A disruptive bunch to say the least. The worst kid is a black teenage boy named "Deshawn". He has made it nearly impossible to get anything done.
    But... Monday evening I got a surprise. I walked into the classroom and Deshawn was sitting in the front row instead of his usual back of the class. The class started off great and Deshawn was very well behaved. He quietly sat there smiling at me. Then suddenly I noticed something and
    O-M-G!! Deshawn was wearing a t-shirt and gym type shorts. Like I said he was up front and his legs were kind of spread wide. And I finally saw it!
    Hanging down out of the leg of his shorts against his thigh was the head of his cock! Probably 2-3 inches of a huge black cock hanging out of his shorts. And he knew the exact moment I noticed it. His smile got bigger than ever. The entire class time I couldn't stop looking. I kept thinking about how long his cock must be to hang down that far. I mean it was so big I wondered if it could have been fake. If it was real it literally had to be nearly a foot long!
    As the class ended He reached down and tucked it inside his shorts before standing up and walking out.
    So far every day this week he has done the same thing. And he knows I can't stop looking! Now I can't stop thinking about it. What do I do?