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Where is the most unusual or risky place you’ve masturbated or given/received a handjob or blowjob?

Laying next to each other in separate chase lounges. I stroked my friends cock on his porch during a sleepover. Seconds after he came his mom said through an open window, it was time to sleep. The curtains were closed, but she might have heard our whispering, perhaps more. I was surprised he could sleep after just making a big mess, lol.
 
Let's see... Had crazy sex in the library, fucked at the zoo, bj during a movie, fucked at a crowded nightclub, sex in many fitting rooms, and my favorite... fingered a girl at the police station. Oh, and fucked my bosses daughter on his desk at work.
 
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In my car while driving.
In the conference room at work in the middle of the day with over a dozen people in the office.
 
This is fun.... College campus midnight fuck under an evergreen bush 5 ft from a sidewalk....people walking along one couple stopped and watched for a bit through the branches of the old evergreen.... City park parking lot had girlfriend bent over next to the car she asked for it.... and i was happy to give it.
 
Once fisted my first ex while she sat in a big leather arm chair just inside the open patio doors of our ground floor room, about 10 feet from a hotel sidewalk.

Curtains were open, lights were off and it was late.
 
Sorry, this is not any of the above, but I thought it's worth posting.

Before my wife and I were married, we traveled to Europe together as part of a group. She was sharing a room with her sister who was very religious. One night we were together in their hotel room and messing around. We wound up fucking standing up while her sister was asleep on the bed right next to us. She was a sound sleeper - I think.
 
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Masturbation... from the mundane (behind some bush just off a freeway) to the slightly more risky (in a clearing in the woods, watching a couple going at it a few yards away, next to a stream, with the woman half-sitting on the leading edge of the car hood), to riskier (by myself, at a urinal at an arthouse-type cinema (2-3 of them, actually, to release that horniness my 18-year self felt 24/7) after seeing bare breasts or bush on-screen - those were the late 1960s, after all), to much riskier (at one of the crenellations in the structure in the picture, in the dead of winter) to the (riskiest? craziest?) late at night, standing right in the middle of a path in the open, in a park abroad).

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Handjob? That would be that night, when we were driving on a deserted street (more of a road in semi-rural surroundings), me with my hand inside my girlfriend's pants, fingering her, she jeking me like crazy, so much so that I felt we had to stop and park right there on the road shoulder to do it safely... That is, until a police cruiser stopped behind us, all lights flashing. We had to really control our movements to avoid giving hints as to what we were doing. Cop came next to the car, asked whether everything was OK, told me to drive on, away from this unlit stretch of road...
 
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wankerholic42 said:
There are many occasions I’ve indulged in such activity in risky circumstances. Two come to mind and both concern public transport.

First example: I once wanked a guy off on the back seat of the upper deck of a London Bus as we crawled up Regent Street during a busy lunchtime. When he came he shot all over the back of the seat in front. Needless to say this was in the pre-CCTV era!

The other occasion, also pre-CCTV, occurred when I was travelling home on a night bus. I lived close to the bus depot. Mine was the final stop. The young male conductor had collected my fare earlier and when not too far from my destination, he came upstairs again, probably to check if anyone was still on the upper deck. I was the only remaining passenger.

He came along the aisle to the rear seats where I was sitting and leaning against the back of the seat in front of me, asked if I’d been anywhere nice. I told him I’d been to a club. He asked which one and I told him Heaven which was a very popular gay venue at the time, but probably not known about by straight people. He obviously knew it as he asked: “Did you score?” then adjusted the front of his trousers. I replied “Not this time.” ”I’ve been there,” he said. “ Great place. Very hot.” He adjusted what appeared to be a slightly larger bulge.

”Boldly, I said “Do you want any help with that?” He replied ”Have to be quick as we’re getting close to the depot.” As he was saying that he unzipped and fished out his lovely fat cock, almost at full erection. I reached out and, spitting on my hand, grasped his cock and started wanking it. He leaned back, eyes closed and let out a sigh. “Go faster!” he moaned. I did, delving inside his fly with my other hand and gently pulling out a pair of ample balls. I cupped them in my hand as I jacked him off furiously. “Oh, fuck!” he gasped. I leaned forward and took his bell-end in my mouth as I finished him off down my throat.

Before I got off the bus we exchanged phone numbers and had many hot sessions in the safety of my flat afterwards.

Now it’s your turn, folks!
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Many. Where to start. A sister of a buddy I’ll call her Nay, Man she was something would not say cock or pussy. It was girl bottom or boy bottom. Ohh well. I was the first cock she sucked and first time didn’t finish sucking I fucked her. After a few years not seeing her she called one night and was managing a quick lube or something oil change place. You know glass doors and front. Office upstairs. Man what night. All over that place she sucked my cock. On the owner desk we fucked and she wanted to suck me. I lost count how many times she cum while she was riding me. I was sore the next day I think she bruised me at the base from pounding down while she rode. Absolutely amazing. This was one of those time she was hollering I want your cum. I love sucking your cock. There was even a police car the drove by and used his spot light in the building. LoL. Made me a lil nervous. There were many other times. Another lady Mary, in a computer room where they had large commercial laser printers for billing. I was working on one and she came around back where I was. Had one of the doors open. She kneeled down out of site pulled out my cock and started sucking my cock she was doing a great job. One of the operators walked up. She slowed and I answered their question. As soon as they walked away I filled her mouth and she swallowed all of it. Stood up and said thanks and that she was headed to the restroom to take her edge off. She visited in my office many times. Amazing.
 
aya_amano said:
I guess when I gave my fwb a blowjob in a parking spot at an adult toys store.
It was dark though but I could see the shadow of people walking past the car.

More recent was when I let my best friend suck my breasts with the curtains open.
Not sure if that counts as unusual though.
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Not so much the sucking, but perhaps the curtains?
 
My Uncle was a cop and had a house in the country with his family. I'd stay the weekend sometimes to visit my cousins.

Once when I was 19 and my cousin was 18, she jacked me off in the barn loft after asking to see my penis. My Uncle was working just below the loft and we had to be quiet. He was a giant of a man who would have kicked my ass severely.

I was terrified and loved it at the same time! I returned the favor years later, and we never played again.
 
I know you are not supposed to do younger on this site but that’s where it starts, and in mature reflection I think this was the most dangerous thing I ever did. Firstly because of my age and secondly because of my total naivety.


When I was about 14/15 or so. I had a strong sexual curiosity and fantasies around sex and especially giving oral sex.


My fantasies continued and developed into thoughts of having sex with a total stranger and sometimes more than one stranger.


This went on throughout my informative years. I was outwardly very shy and did not have a boyfriend or anything like that.


One afternoon I went to the cinema and after a little time a guy sat next to me although the cinema was quite empty.



After a few minutes he started talking to me, he was about thirty or so, and very soon he started to touch me with his hand, sort of around my knees and up my tea shirt, I did not resist to much and after a short time I got up and went to the toilet, where I took of my sports bra and made sure my tea shirt was out of my skirt, I thought for a minute and decided to take off my panties as well.


When I returned to my my seat, I passed him by and sat at the end of the row.


After a few minutes he moved up next to me and soon started to touch me up again, when he realised that I was not wearing any underwear he said well now that’s more than I expected from you.


He played with me for a short time and then put his jacket over his lap and gently moved my hand into his lap.


He then took out his manhood under the jacket and said give me a little cuddle with your hand, I responded and soon he was gently pressing on my shoulder and bringing my head down on him, I was scared that someone would see us and stop us, but he said Shhhh and just give me a little caress with your mouth.


This is something that I had been obsessing about for a long time, I took him in my mouth and it was more than I had ever imagined. After a short time he said I am getting close to cuming, I was not ready to stop so I sucked him a little more firmly, I felt the first gush of cum fill my mouth, then spurt after spurt as I tried to keep up swallowing with the continuous ejaculation.


After a few minutes he was spent and I was fulfilled, but hornier than I had ever been in my life.



I lay there for a few minutes just holding him in my mouth, then he said do you want to come home with me and continue there? He said I live quite near, I had arranged to meet my mother after the cinema, and thought for a moment if I should go with him or meet her as arranged, this was before mobile phones and social media, so I said I could meet him again the following Saturday if he wanted, he said ok and I went to meet my mother.


The following Saturday I went to the meeting point as agreed and waited for an hour or so but he did not turn up. I looked out for him, at the cinema and when I was in town, but didn’t see him around.


Several months passed and one day I read in the newspaper that Fredrick Deacon 35, had been charged with and convicted of the murder of two local schoolgirls it was quit a big case here and everyone was talking about it, as nothing like this had ever happened in our town before, there was an accompanying photograph after the conviction. “It was him” One he had killed a few months before meeting me and one soon after.


I think that was the most dangerous thing that I ever did even though I didn’t realise it at the time.
 
TaraTraynor's story, above, reminded me of an incident from my past, but without the dark turn at the end.

When I was 21 I found myself on a Greyhound bus traveling from Pensacola to Jacksonville a few days before Christmas. The bus was almost full. Around mid-afternoon the bus pulled into Tallahassee, Florida. Everyone was ordered off the bus while the driver took his dinner break. An hour we lined up to get back on, but with the new passengers the line was long and I was near the end, standing behind a sweet young black woman wearing designer jeans, gold-tipped cowboy boots, and a gorgeous smile. As the bus filled up I saw my chances of getting a seat rapidly diminishing.

At that moment a another driver walked up to the line and said his bus was following the same route, and we could ride that bus if we wanted. I did not have to think twice. I immediately volunteered to ride the second bus. A second later the young woman in front of me also volunteered for the second bus. We were joined by an old man who dragged himself behind us. When we got the bus, I helped the woman with get her suitcase onto the bus, and then entered behind her. She took a seat in the middle of the bus, and took the seat across the aisle from her. I think she was surprised -- the bus was empty but for the two of us and the old man who sat in the front row.

We talked while the bus traveled through the deep South. It stopped frequently, taking on more passengers that it let off at each stop. Before long the bus was getting full, so I asked her if she wanted to sit next to me so that we could continue our conversation unimpeded by other passengers. She immediately joined me. As our conversation continued our heads tilted closer together -- so we could speak softly and still hear each other over the din of the other passengers -- and we kissed. She rested her head on my shoulder. I thought she wanted to take a nap, so I spread my coat over both of us, covering us completely from our necks to our knees.

Almost as soon as we were covered by my coat, she got busy. She unfastened my belt and pulled down my zipper,reached into my underwear, and pulled out my cock. She slowly stroked me under the coat while we kissed each other above it. I reached under her blouse and caressed her tits, first above the bra and then beneath it. She continued slowly stroking my cock, so I went for her crotch also. Her jeans were tight, and I was having some difficulty getting my hand inside them, so she slumped in the seat, providing easier access.

Passengers continued to board the bus as night fell. She and I continued to play with each other beneath the coat. After a while I looked up and saw that we were entering Duvall County, which is where Jacksonville is located. She saw it too. She asked me to meet her in the restroom in the back of the bus. I looked around and saw that the bus was completely full. There was no way to do that discretely. I told her we can't do that, everyone would know what we were doing. She asked me, "why do you care, you'll never see these people again." I thought about it and decided she was right. She got up and walked to the restroom. I followed behind her a minute later. I locked the door behind us and we both pulled our pants and underwear to our ankles. She leaned back, spread her legs, and reached for my cock. She steered it into her soaked pussy. She felt wonderful --tight, hot and, and slick with juices. We fucked furiously -- we knew we trip was almost over -- and I asked her I could come inside her. She said she was on the pill, so I pumped with all I had until I erupted inside her, filling her with my cum.

I pulled out, pulled up my pants and returned to my seat. She followed behind me a minute later. The bus pulled into the station, and she asked me to let her exit first. We kissed one last time, and then she exited. I waited a minute, then got up and off the bus. I walked past her as she was greeting her parents. I smiled in her direction, but did not look back as I walked away. I never saw her again, but I think of her often.
 
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