Riskiest Handjob You've Ever Given Or Recieved.

Girlfriend wanked me under a blanket while on a sofa watching tv. Her sister was in the room watching tv as well. My gf suddenly stood up and the blanket fell away. Her sis got a look at my pathetic little erection while I tried to retrieve the blanket. She laughed and told my gf how her bf was way bigger.
 
My ex girlfriend Sarah's family had a cottage on the Bay. The water was always cold and you had to go out far to get deep. Her parents were in the cottage while we were in the water. Sarah's ass looked like two muffins squished together. I was standing in an intertube and she was sitting in it. I vividly remember her pulling my shorts down and stroking me off with both hands while the intertube and my back blocked the view from the shore. Man, it felt great. It continued in the boat house.
 
When my wife and I were dating, a group of friends and us rented a villa for a weeks getaway. One afternoon we were all sitting on couches around the fire watching a movie. The pair of us had a blanket over us and our friends had no idea she was jerking me off while I was fingering her. It was so hot, I have no idea how we managed to not get caught out. She got up and went to her room, a few moments later I went to “the restroom” but actually went to her room where she got down on her knees sucked me off and I blew my load all over her tits. I think about that experience often, it really was so hot!

There were many other occasions of handjobs in the car in various locations, almost got caught by the police but I managed to get my cock zipped back up before they got to the car, and one time at the movies, blew my load everywhere, that was fun!
 
A new girlfriend and I went to a pool party at her friend's house, and there was a cabana next to the pool. After saying hello to everyone, we went into the cabana to change into our swimsuits. People were literally standing a few feet away on the other side of the door.

Since the relationship was quite new, I instantly starting getting hard as soon as our clothes started coming off. She noticed, and reached out to stroke me a few times, then dropped to her knees and started sucking me. She made sure I was rock hard before standing up and putting on her suit. I put on my trunks, but there was a very obvious tent in front! There was some light-hearted comments from just outside the door asking "Why are you guys taking so long?!" She left first, as I had to calm down enough to not have an obvious raging hard-on when I joined the group!
 
Sat on a small hill by a popular lake at dawn on a warm day in spring and smoked a cigarette, watching people having barbecues and chilling. Out of nowhere, this jacked guy in his late 40s stood next to me, apparently he came from the side not facing the hill. I look up at him, he turns around and starts walking back down the hill. Immediately, I get this excited feeling in my groin, get up and follow him. He’s waiting for me a couple of meters down the hill, so we are out of people’s sight. I ask him how he’s doing. He just smirks and says nothing. At this point I’m so turned on by his attitude but also second guessing if I misread the whole situation. Then he says that he needs to pee, pulls down his pants, takes out his huge dick and starts pissing.
I just stand there, observing him. Once he’s done, he turns towards me and just stands there, dick hanging out. I take a step closer and take it in my hands. He moans and I really start going for it. I jerk his fat cock for a couple of minutes, playing with his nipples, when he says ‘I want you to cum on it’. He grabs into my pants, massaging my dick. I open them, now we stand there, jerking each other off with our pants pulled down, hearing people laughing and having fun on the other side of the hill.
I cum in like 3 minutes, covering his dick and lower abs with my cum. Shortly after, he starts moaning so fucking loudly, which makes me go faster and harder on his cock. He shoots a massive load. I’m starting to get nervous people might have heard him and pull up my pants. He looks down on his cock and says ‘you made a mess’ and starts collecting my cum with his fingers and eats almost all of it. Then, he just walks away.
 
My girlfriend and I were on my bed, I had 2 fingers in her and she was jackin' me when my female cousin (her best friend at the time) walked in. Whoops! This was MANY, MANY years ago. Funtime interruptus!
 
Not sure if this would qualify as risky happening as it did on a gay nudist beach, but I'll offer it anyway. It was last summer, on one of my visits to Climping beach dunes. I'm stretched out naked on a towel, glistening with a good coating of factor 30, cock nicely throbbing and dribbling precum. A passer-by stops and watches me for a few minutes. I squint a look in the bright sun and see his outline. He approaches and kneels, running his fingertips around my nipples, as if testing the water. I stretch out and show my approval, no words are needed. He grasps my shaft and starts stroking me, slowly at first, gradually increasing. I keep my eyes closed but am aware there's at least one other watching from the next dune. My stroker is determined, he's clearly not there to edge me, his speed making it impossible to hold off. Within minutes I'm approaching orgasm and let out a groan. I have to grab his hand to stop his action as I shoot several thick ropes of cum up towards my chest. He eases his grip from me and I feel his finger run through the cum. I'm not sure if he tasted it or just rubbed it into my oily skin, as my eyes stayed closed. Then he tapped my thigh a few times, got up and left.
 
Had a gf who loved being risky. One example is we went on vacation with her parents and her dad insisted we all drive together instead of me driving my car with my gf. She threw a blanket over our laps and started rubbing my dick through my shorts. She unzips me and starts jerking me off and I was trying not to make a sound. So she took the blanket away exposing my dick and I hurried to cover myself and she started laughing. She's pumping away and I mouthed the words I'm going to cum. So she starts stroking faster and I didnt want to cum and make a mess, but too late and I blasted into the blanket and some dribbled out onto the floor. That was a mess to clean up, wiping cum from between the grooves of the floor mat. It was so hard not to make a sound as I came because it was a big load and felt amazing her stroking me.