Riskiest Handjob You've Ever Given Or Recieved.

dude had been teasing my crotch all night and he found me on the dancefloor where he kinda took me to the corner, lowered my jeans and boxers and wanked me off. it was packed so nobody really noticed me stood there moaning in pleasure shooting cum. he licked it all off his hand and later on took me down an alley and sucked me off
 
On a NJ transit bus in the middle of the day. An older guy I always saw on the bus going to the peep show places in Time Square. Always had a huge hard on and his dick was really long. I sat next to him after moving my chair and made him cum in about 5-10 minutes before we got into the Lincoln Tunnel. He actually stayed hard after he came. He wanted me to keep jerking him off. We had to get off the bus soon so I moved back to my seat. Had cum on my hand and the back of the seat we sat by
 
I woke up in my window seet flying back from Europe to find the married man beside me (his wife and kids were the row in front of us) had thrown a blanket over my crotch and was rubbing me off through my pants.

we had literally exchanged zero words before this.

Apparently I threw a chub in my sleep and I was his 'daddy type' and he couldn't help himself.

So I unzipped to make it easier and he even leaned over for a few licks
 
Got jacked off in the back row of a theater by my then girlfriend. My current girlfriend sucked me off in the woods at a park. I have jacked myself off in more places than I can list.
 
It was in my teenage years. I had two girls that were good friends, one said the other liked me and as we all talked and got to know one another, they invited me over to their house where one was sleeping over.
So late at night just before the parents were going to sleep they snuck me in through a bedroom window.

One thing led to another, and it turns out both girls had a thing for me. Or at least no one was angry about it. They stripped me down to my underwear and I appropriately requested they do as well. So here we are almost naked and I’m lying in the middle of the bed with these two girls, where I let their curiosities run free exploring me.

So after a bit, I’ve got one of the girls jerking my cock and another is watching it grow as I play with her huge tits. Then a knock at the door! It’s the parents! I make a mad dash for the closet with nothing but underwear on. They shove my clothes under the bed and answer the door to find Mom saying goodnight etc. i could see the room light in in the crack of the closet. All I could picture was them opening it up, me standing there with a hard on sticking out of my underwear and that instant we all lock eyes. I was prepared to say Hi and wave and bolt out the window regardless of clothes or the keys to my car, but fortunately, it didn’t happen. Mom left, the door shut and lock once again and they opened the closet giggling. I’m sure it’s the closest I could have came facing a shotgun or revolver. Though we all were roughly the same age, no parent wants this happening to their kid or in their house.

After all the excitement, we picked up where we left off. But this time, no interruptions. One girl begins stroking me again, then slowly goes down on me while the other and I made out and sucked her tits. Eventually, we all were heated, wet and naked. The dimly lit room and the raised level of music to drown the sounds but not wake Mom and Dad we shifted around on the bed. Now I had my big titted friend position her pussy above my face as she sat on it for me to taste her wetness. Meanwhile, her truly slutty friend went from sucking my cock to sliding her wet slit up and down my rigid dick as she pushed her friends ass onto my face. These seemingly shy girls suddenly turned into freaky, lustful animals. I slurped and sucked her pussy as she slowly grinded my face moaning softly as she played with her nipples while her friend feverishly slid up and down my cock rubbing her lips as her wetness and my precum began to make a sloshing noise.

We all were moaning with pleasure as my slutty friend told her big titted friend to come suck his dick so she could watch. She said she has never sucked a cock before. She apparently was the shy one, because her friend seemed to know her way around a naked guy. Her friend get between my legs and her friend pushes her head down onto my cock saying open your mouth and suck! As I could immediately tell the difference in head, it by no way didn’t feel good. She was much slower at her pace which was good for me, because I knew I’d blow my load soon. As her friend watched and coached her girlfriend in pleasing my dick, I fingered the coach’s wet pussy keeping her in the mix. She was super wet and I managed to get two fingers in her before she began to hump my hand in pleasure and begin to cum. She put her face in the blanket moaning as I jabbed my finger into her and flicked the tips. Her friend watching my hand push deep into her friend as she kept slowly taking my cock in her mouth.

After my little slut finished her orgasm, she said to her friend you should let him rub his dick in your pussy, it feels great! She seemed hesitant as if she thought we were going to fuck, but I told her, I won’t put it in you, I promise. I got off the bed, and she moved to the side so I could spread her legs and place them on my chest. As I stood next to the side of the bed, I bent my knees so I could lower my hard dick to her swollen wet pussy. She was a natural blonde and this was in the 80s, so she had full bush in effect! I felt the warmth of her lips and began sliding my dick up and down her labia. She was watching me and I asked does it feel good? She said yes! I slowly kept my rhythm and her slutty friend truly enjoyed being a voyeur as she watched the action rubbing herself next to her friend. I couldn’t believe, what I expected to be a night of perhaps making out with one girl feeling some boobs, turned into my first 3-some without penetration.

I continued to rub my sick on her pussy, stopping at times to slap it on her clit. She and her friend would just smile at me me as this horny guy with his hard dong sticking out plays with their curious nature. I felt myself getting close to cumming and indicated I would cum soon. My slutty friend said to cum on her friends big tits. She was the one I was told who liked me so I imagined that’s why she got all the attention. So when I was close, I climbed in the bed and jerked my dick over her tits. When the point of no return came, I leaned my head back and let loose! My first few shots, being a young virile guy, totally missed her tits and shot onto the slutty girl on the other side of her. I hit her face and chest some and when I realized it, focused my cock downward to her big tits. As ropes of cum spewed from my dick. The slutty girl was wiping cum from her and putting her fingers in her mouth. The other girl just watched as I painted her big tits with my load.

When I was done. I looked down at my creation with drops of cum oozing from my dick still. My slutty friend grabbed my cock and milked the last of my onto her friend as she began rubbing my cock head on her tits. She said, wow, you cum a lot! I told her it was because this was sooo fucking hot! They giggled and we touched and rubbed each other slowly as the heat subsided and cum began to become sticky and dry.

One of the girls (the slutty one) grabbed a wet cloth and washed my dick for me, but kept putting me back into her mouth. She said she couldn’t get enough of me. I told her, whenever you guys want my cock, I’m there. She cleaned her friends tits off and I dressed and we chatted a bit before I crawled out the window to my car and went home. Re-running the night over in my head again and again!

We all kept in touch, though the big titted girl and I never really dated, the slutty girl always kept calling me up on the side to pick her up so we could park and she could suck and ride my dick. She said not to tell her friend. I didn’t care. We both were getting off. We find a secluded spot n my car and sometimes she’d blow me and other times I’d put a condom in and we’d fuck! One time, I didn’t have any condoms and she wanted to duck so bad, that I fucked her ass. She screamed it hurt so bad, but she wanted to feel my dick in her so much she begged for me to fuck her ass. It was my first time too and no sooner had I pushed my way in did I begin to cum. I squirted inside her as I pulled out and squirted under ass and pussy and in my car. It was a mess. But what I loved about this girl is she always cleaned my dick off. She really had a thing for my cock. She used her panties to wiped my dick and the cum from it. She always cleaned up the car and always wanted one last touch or one more taste of my dick. She truly was insatiable. Wish I had stayed in touch as we grew older and wiser in the sex world. She would have truly been a great sex partner and I think a bit of a submissive slut too. She always wanted dick and would do anything for it!
 
On a coach/long distance bus at night coming back from an event in London as a student with a girl I was dating at that time (I was 21, she was 18). It was a bit cold so we had a hoodie on our laps as a sort of blanket. My hands were a bit dry, so she put some lotion on her hands and started rubbing it in my hands. She then started touching my crotch, unbuttoned my jeans, slid her hands in my boxers and gave me a nicely oiled up wank. I had to stop her before I was about to cum as I didn’t want to make a mess. We fucked the very next morning at her house and it was glorious.
 
I don't know that this was particularly risky as it was before the age of drones.

Wife once gave me a handjob while we were floating on a two-person raft on a private lake. I was naked and she apparently couldn't resist jerking me to orgasm.

Ah, the great outdoors.
 
Have received and given hand jobs on airplanes, especially late night / redeye international flights when nearly or all of the other passengers are sleeping, sometimes under a blanket or openly if no one else is awake. Have received 'jobs in movie theatres, quite a few when I was younger and the occasional one now and then, have also received them in private screening rooms. Also in public bathrooms, gyms which appears to be very common. More exciting when there's possibility of someone catching you in the act.
 
My then girlfriend, her gay friend and I got really drunk one night some months ago, and all passed out on the same bed. My then gf being drunker than both of us was out cold. Long story short, I gave her gay friend a hand job (technically, blowjob) while we were all still on the bed. The rush was intense. Every so often she would wriggle a bit or make noise, while his cock was in my mouth and I wound literally freeze in terror haha. 10 mins later,
cum running down my throat. One of the hottest nights of my life
 
This one wasn't me but someone I talked to. He was standing in line for a ferris wheel with his bf while freeballing in some tightish shorts. He pushed his bulge into his bfs hand and he started stroking him through his shorts. After a little bit he got closer and eventually began unloading in his shorts. Said the sensation of the fabric really amplified the orgasm and had to hug his bf to keep from basically convulsing he came so hard. Had to walk around the park with a load in his shorts. Luckily they were black.
 
I woke up in my window seet flying back from Europe to find the married man beside me (his wife and kids were the row in front of us) had thrown a blanket over my crotch and was rubbing me off through my pants.

we had literally exchanged zero words before this.

Apparently I threw a chub in my sleep and I was his 'daddy type' and he couldn't help himself.

So I unzipped to make it easier and he even leaned over for a few licks
Wow wow that hot
 
Riskiest place was probably when I jacked off the guy I was seeing. It was a quiet cinema and we were at the back. I could tell he was nervous and a little horny so I thought I would give him something to remember me by.