Embarrassing Masturbation Moments

This first story could've happened to anyone but what really makes it embarrassing is that it happened to me on two separate occasions.

I think I was 17 or 18 at the time and during the summers I always had the house to myself on the weekdays, which meant I was almost always naked and usually went out by the pool first thing in the morning to jerk off. But on this day it had been raining pretty heavily in the morning so I had gone out into the yard about mid afternoon, once the sun had come out. I laid down on a lounge chair and started stroking myself. I stopped for a moment to put on some sunscreen. Being the middle of summer and the fact that I was almost always naked when I was outside meant that I went through a lot of sunscreen so of course the bottle happened to be empty. I knew I had more sunscreen in my bedroom so I went back into the house, casually stroking my dick to keep myself hard. Here comes the embarrassing part: the stairs to get up to the second floor where my bedroom was were directly in front of the front door, not normally an issue because the door would be closed. However because it had been raining that day it wasn't really warm enough to need the air conditioner so I had opened the door and some of the windows and forgotten about it. Entering the house from the backyard through the kitchen, I had to go through a small hallway to get to the front where the stairs are. Unfortunately you can't see the door until you make it all the way through the hallway and as I stepped through the hallway, casually stroking my dick, stepping right in front of the open the door, I came face-to-face with the mailman. He laughed and said it wasn't the first time he's seen something like that and most likely wouldn't be the last.

The second time this happened to me I was 24. Myself and two friends that happened to also be jerk off buddies of mine had rented a house together. Unfortunately there was no swimming pool but it did have a very secluded backyard with a hot tub which is what we were hoping for. It was a Saturday in early summer. My roommates and I had been working on the yard, getting it ready for us to have fun. They both left to run some errands while I finished cleaning up. I was covered in sweat and dirt only wearing a pair of cargo shorts so I went straight down into the basement, where the laundry was. I took my shorts off and threw them right into the washer. At that point I was naked and had gotten hard from thinking about how my friends and I were going to be enjoying our newly landscaped backyard and hot tub, jerking each other off out there. As I walked back up the stairs naked lightly stroking my dick I saw the mailman. He was leaving a package on the screened in porch, the door to which I had left open, the door that was facing the very same basement stairs I was walking up.

This was a total misunderstanding but turned out to be one of the most embarrassing moments of my life.

My family took a vacation when I was 13 and I met a bunch of guys at the beach. Most were my age, a couple were a year or two older. They were all super hot and it was the beach so obviously they were just wearing bathing suits, so I was pretty turned on. They invited me back to one of their places for a barbecue. I went and there were a lot more shirtless hot guys there there was no way I wasn't going to pop a wood in front of everyone. I excused myself to the bathroom, dropped my swim shorts and started jerking off, staring at the shirtless guys out the window. I was getting ready to cum but I didn't want to stop looking out the window and if I went to the toilet or the sink I would've had to so I grabbed something out of the hamper to cum in without looking to see what it was. I had no way of knowing the lock on the bathroom door was broken. One of the guys that had invited me came to check on me because I'd been gone so long and he heard me grunting so he opened the door just in time to see me spilling my cum into his underwear.

A number of years ago I guess I would've been 23 or 24, I met a guy named Derek online. Derek was straight but had an interest in trying out a jerk off buddy.

Derek was an extremely large muscular man. He was 40 years old, just under 6'4" with black wavy hair, piercing blue eyes, an extremely furry chest and I'm never going to forget his 10 3/4 inch uncut cock.

Derek and I talked online for about three weeks and even had a few over the phone jerk off sessions before we decided to meet up. He was extremely nervous and we spent about an hour talking to each other before we got down to business. It was a surprisingly sensual experience considering it was his first time having any sort of interaction with another guy. We undressed each other pretty slowly and just stared into each others' eyes as we stripped each others' dicks; we ended up coming all over each other so we took a shower together where we washed each other off and jerked each other off again.

The embarrassing part happened a week later when we met up again. We were naked and jerking off when he wanted to try kissing me so he sat down on his couch and I sat in his lap and we started kissing while he jerked me off. We had gotten pretty into it so we weren't really aware of anything that was happening around us. Just as I was coming, shooting my load in his hand and up onto his chest, the door opened with a full view of us and in walked his sister and his girlfriend, stopping in after going shopping together.

About three years ago my roommate was dating a deaf woman. His computer was in for repairs so I was letting him use my laptop to video call her. He would normally take my laptop into his room or into the kitchen but the battery was low so he had it plugged in at my desk in my bedroom. I had been in the shower and they were speaking in sign language so I had no idea that my roommate was in my room. The water in the shower was a bit cold so I didn't want to jerk off in there. I walked into my room from the bathroom completely naked, hard and stroking my dick in full view of the laptop camera.

Something else embarrassing happened at around the same time. My roommate had made a video of himself jerking off for his girlfriend and left it on my laptop by accident. I found it got turned on and decided to jerk off to it. I put headphones on so I could hear the sounds he was making in the video and he wouldn't be able to hear what I was watching if you walked by my room. Unfortunately because I was wearing headphones I didn't hear him when he knocked on the door so he didn't think I was in my room and came into borrow my laptop again. He wound up with a full view of me spread out naked on my bed and jerking off at full force. Fortunately he couldn't see my computer screen and to this day has no clue I've ever seen the video or that I jerked off to it.

This was not only embarrassing but could have potentially gotten me fired, if my boss wasn't an occasional jerk off buddy. This happened just a few months ago. Because of the current circumstances of the world a lot of the usual fun that I have with friends has taken a turn to the digital. Some friends and I have been either jerking off and live camming with each other or recording videos and sending them to each other. I made a video of myself jerking off. It was pretty hot  and there may or may not have been toys involved but I accidentally sent it to my friend using a new work email that we were using for a special project. Because of that special project, every email I send from that account is automatically forwarded to my boss. What really embarrassed me about this incident was that I was dumb enough to use the wrong email. But it actually worked out pretty well as ever since this happened, my boss and I have been exchanging videos at least once a week.