Your most daring sexcapade

[wingonwing]

My late wife and I loved getting naked or semi-naked and playing with each other in all sorts of public settings -- from her wearing see-through tops sans bra to the usual stripping naked and masturbating in the car on trips and sailing naked. The more daring, the more exciting and fun. Have you done the same? What was your best experience?

[steelydon]

I wouldn't say it was my most daring sexcapade but I have sailed naked and masturbated a few times. Only once to the right true end when I shot my load in the general direction of the cockpit (lovely word that ) drains. Sadly these were single-handed adventures!

[oliviaanne]

I'm not sure about daring, but it's definitely the most voyeuristic thing I've ever done. About a year ago my boyfriend’s brother and sister in law invited us over for dinner. I'll call them Nick and Kristina. We had a lovely dinner with plenty of cocktails and a couple of bottles of wine. After Kristina and I finished cleaning up we joined the guys who were already in the hot tub.

Nick and Kristina were telling us about their honeymoon in Jamaica and how they had spent an afternoon on a nude beach. The guys started teasing and daring Kristina and I to take our tops off. Well, I guess I had just enough wine to make me say "fuck it, why not?" I untied my top and Kristina did the same. I was not at all expecting what happened next. Nick stood up and dropped his swimsuit exposing a raging hard on.

He stepped toward Kristina and she promptly took his cock in her mouth and started giving him head. Not to be out done my boyfriend did the same and the next thing I knew Kristina and I were side by side with the brothers cocks in our mouths. It all ended with Kristina and I bent over the edge of the hot tub getting fucked from behind. It was so hot looking at Kristina getting pounded. Her face was flushed from the heat of the hot tub and the hard pounding Nick was giving her.

It wasn't much longer until Nick pulled out and shot his load onto Kristina's lower back. Within just a few seconds of Nick cumming my boyfriend squeezed my hips and his cock pulsated inside me as he came. We ended up leaving the hot tub and all fucked again on their living room floor before going home. I'm sure the thought crossed everyone's mind to swap partners, but I'm glad we didn't.

[mushroomhead]

On the Kern River in middle California. Found a place next to the road to pull out. Went into the river and positioned a couple of rocks so as when I sat in the river and spread my legs, the water would flow over the rocks and fall directly on my cock. Got totally naked and let the water do its work, all while cars drove by, but they couldnt see me unless they pulled over in the same turnout and got out and looked down to the river. I sat that for about 45 minutes edging and enjoying. Pretty sure no one ever saw me, but ya never know. I actually hoped that someone would see me.

[goodniteswearer89]

My most daring sexcapade was a few years ago when I was dating this girl me and her would go to the park in town and sneak into one of the bathrooms either then men’s or woman’s and have sex in there. It was so exciting and daring cause I was a little afraid of getting caught luckily we never did cause the way we would do it was one of us would go into the bathroom first so it wasn’t obvious what we we doing and when we were done one of us would exit first then the other one a little while later.

[Sean1969]

Had my first sexcapade in the back of police station, when she was released. The best load ever!

[dlihret]

My most daring sexcapade occurred many years ago when I was a sales rep. One of my accounts was a very small company with only the owner and his secretary in the office. The secretary was a few years older than me, but loved to spend time in bed with me. (A story for another time)
I had made an appointment with the owner, but when I got there the secretary told me he had been called to a job site and wouldn’t be back for the rest of the day. Things progressed and soon she went over and locked the door to the office suite. (It was in a building with other offices along the hallway.)
We couldn’t figure out where to fuck, so she suggested her bosses big leather desk chair. I dropped my pants, had a raging hard-on, sat down and she got on top and ground her pussy onto my cock until we both had delightful orgasms.
She got off me and was dripping cum. She grabbed a Kleenex from her desk, jammed it between her legs, pulled her skirt down and waddled down the building hallway to the ladies room to clean herself up. She came back a few minutes later as I was finishing tucking in my shirt and straightening my tie.
We didn’t get caught, but every time I visited her boss in his office, we both smiled to ourselves, imagining him sitting in the chair we had fucked in!

[golfpro]

SO many but a few are, a park overlooking the Mississippi below a hill with people playing softball above us out of sight. A trail at Lake of the Ozarks state park campground, a young couple walking a trail we didn't know about catching us fucking on a blanket. Late night on a lonely country gravel road up against the car. In a brightly lit hotel room up high in the large window overlooking downtown. A bed and breakfast on 100 acres of land overlooking the MIssouri River out on the second floor deck with a barge passing by headed up river. My wife leaning over the deck rail facing the barge,...maybe 200 yards away, her tits flapping over the railing as I fuck her from behind. Easily seen by the deck hands on board, a few who came out with binoculars One of them got the money shot of me pulling out of her, getting her down on her knees in front and her jacking my load all over her face. When we were done we waved to them and they waved back as they headed out of sight.

[varvara]

I can't do that now. Unfortunately, life has its own conditions and barriers. In my experience, there are several such historical milestones. But the first, as it happens, is the most exciting and unforgettable. I have been going to this for a long time and gradually. More precisely, my older friend helped me. She introduced me to a group of completely unfamiliar people (her colleagues), where I could safely be completely naked, despite the fact that they were doing their usual business., of course, being dressed. It was an unforgettable experience.

[lestathunter]

Ok I was debating on posting this cause im still new here, but everyone seems really cool so im gonna go for it.

A while ago i was living on my own after my gf at the time left. We got lucky and got a nice long bungalow with lots of windows and two front doors. It was by no means expensive or luxurious, just old and made that way. Long story short when i shook the break up off I started doing things just to have fun. Listen to music loud, cook whatever i wanted, drink what i wanted and so on. One day i was out getting beers for the night and this woman was handing out her business cards for an alcohol delivery service she provides. She was full of life, passionate about what she did and very nice. She was black, about 5’8” and just filled out to the max. I found her soooo attractive! So i took her card and ordered her service from time to time to drop of beer at my house and i would pay her for the beer and her delivery fee. Well one day i was in a mood and called her with my usual order, i was watching porn all day and just in one of those moods and i wanted to do something drastic. So when she got to my place at the end of the long driveway, i started watching her from the door in the middle the of the house through the side light as she made her way to the door at the end of the house which is the one we always used. I couldn’t help myself, i was looking at her big tits and tight clothes and i had to pull my dick out and stroke it while i watched her walk up the driveway. She couldn’t see me and no idea what i was doing. I came so fast, washed my hands and went to the other door just as she got there.
She was so nice and i just played it cool and left her a big tip. Damn it was fun.

[spunkluvr]

I've wanked myself off in many public places but I supposed the daftest escapade was wanking naked on my neighbour's doorstep. I'd had a couple of drinks and my mates dared me - silly thing to do!

[fastesthandinthewest]

The best experience I have had so far was with these two amazing girls I met at Gatlinburg Strippers. Don't get me wrong, I didn't pay to have sex with them, they were not strippers I just met them there. How they explained it they were a couple and looking for some new experiences and I was lucky enough to make their acquaintance. Frankly I was worried because they were so hot and I would make an embarrassment of myself. Thankfully they were so nice and I felt so comfortable that I did very good and we all had a very good time.

[wankwank]

its got to be wanking off in front of my mother.

i grew up with my mum but stayed with my dad for a while. there was one incident when i was a kid that stayed in my mind. first time i purposely wanted her to see my rock hard cock with it skinned back it definitely shocked her. i discovered masturbation pretty early to me it was the beast thing ever and i wanted her to see me doing it. sunday mornings my mum would be doing house work i remember laying on the bed covers kicked off bedroom door wide open wanking mum walks in put some clothes on the side and says put those away when youre done walked out and closed the door behind her literally made me bust my nut!

i went to stay with my dads not long after that. but that memory stayed with me. when i was about 14 my mum took me on holiday it was like a private villa in spain with a private pool very secluded. i decided i was going to swim naked and my mom came out and lay on a lounger next to where i had left my towel and shots. so i got out of the pool by the time i got to my lounger i was rock hard. picked up my things and scuttled off.

this is the real dare next day she is laying on a lounger next to me and the thought of when i saw her look at my cock the day before came flooding into my head. im laying there rock hard tip of my cock popping out of the waistband of my shorts turning me on even more. daring myself to do it so i just whipped off my shorts and wanked off shot all over my chest grabbed a towel wiped myself off and then jumped in the pool got out and went about my day. my mother didnt say a single thing. i didnt look to see if she could see i just kept my eyes closed and concentrated on knocking one out. she must have heard me cum if she wasnt looking.

i think that was more about a woman seeing me cum though and she was the only woman i had access to at the time. because i then went on to wanking in front of girls trying to encourage them to wank and suck me off. cumming in front of someone was really exciting to me back in those days. but i have always kind of got off on things i know i shouldn't be doing

[rathb69]

My most daring sexcapades have been solo involving masturbating where I might be seen or intentionally getting caught stroking and shooting a load. In front of hotel room windows with the lights on (watched by a maid), laying on a ground floor motel bed with lights on and shades open, in a parked car with women walking by (seen a few times), while biking after removing my shorts (almost caught), on a late commuter train with other riders nearby, and many more.

Late at night or early in the morning, I have walked around without shorts (mostly while camping). Jacking off without the safety of clothes nearby is a rush...

Openly masturbating in a peek show booth, porn theater or Adult Book Store arcade is hot and certainly feels daring, but since the other patrons are there to do the same thing or expect to see men jacking off, it doesn't quite qualify, but it feels daring to let other men watch me stroke my cock.

Recently, I while using a public urinal at an active highway rest stop, as I was peeing I decided to look down at the man standing next to me. I watched him pee and didn't take my eyes off his penis. He noticed and did the same. After I was done, I pulled my cock and balls completely out and and began to stroke (jacking off at a public urinal has been a fantasy of mine, so I decided to go for it). He did the same and we were both hard. We continued to stroke even with another man at the sink on the other side of a partition. I wanted to cum for him, but we were interrupted by another man coming to pee. That broke the spell and I left...

[lestathunter]

spunkluvr wrote:
> I've wanked myself off in many public places but I supposed the daftest
> escapade was wanking naked on my neighbour's doorstep. I'd had a couple of
> drinks and my mates dared me - silly thing to do!

Nice!!

[love2squirt]

I had a guy jack me off as we and his sister all talked in the same room. We were on bed and she on another. I exploded when I came but had to stay quiet and not move too much. It was great !

[ezwriter2000]

Ex wife loved to show in public. Short dress with no panties. Show titties on the highway. Fucked a guy from work in first floor hotel room. Etc. Fun times had by all.

[iamnaked]

Walking out of the forest naked and getting an erection in plain site of dozens of people. And before I could get clear of them ejaculating without touching myself. Then doing the walk of shame walking to my car,
That I purposely parked as far away as possible.

[iamnaked]

Along time ago, I was in the middle of fucking thus woman. Her husband knew she was at my apartment and knew she liked fucking me. He lived in the next building.
He didn’t care, she said he was tired or bored with sex in general.
It wasn’t her fault, she was an in shape flat stomach six foot tall blond.
He knocks on the door,
She picks up the pace,
He hollers through the door, “Honey, I’m going fishing for the weekend, I’m leaving the apartment key under this floor mat,”
I say, “fishing for the weekend my ass, he’s got a side squeeze”
She really starts fucking me harder and I know my dick is gonna get a weekend long workout.
I said,”Get up and go say goodbye naked then come right back.”
She did, after a minute or two I walked up next to her at my open door, both of us naked, I’m hard as a rock.
Her husband said, “Wow no wonder you like this guy, that’s a nice dick.”
He left and we fucked harder than ever.

[iamnaked]

An older couple lived across a canal from my grandparents house. I was 15 and they both were in their sixties. They often saw me playing naked along the canal. I spent my summers with my grandparents and they tolerated my constant nudity and did not make me get dressed if they had visitors. My grandmother would make me put on shorts and shoes if I went to town with her. My grandfather would ignore my nudity but make me stay in the car on town trips to the grocery or hardware store.
One summer my grandparents had to go out of state for a funeral and the couple across the canal said I could stay with them.
My grand parents would be gone for five days.
They left early one morning and I walked around the canal with about ten homes on each side that were almost always empty. Most didn’t live here full time.
Of course I walked around that morning naked with only tennis shoes on. The couple was having breakfast and invited me right in and made me a plate.
The man asked if I was always nude at home with my mom. I said yes.
Then I noticed his penis was hanging out if his shorts and half hard.
That got me rock hard. His wife noticed and said, “I think both you two need release” she proceeded to suck her husband off and then move right over to me.
I lasted maybe ten seconds, if that.
That old lady sucked me off three times that day. The next morning after breakfast she left and went to town with her friends and he sucked me off.
For the five days my grandparents were gone I didn’t have to jack off once. Each day one or both would drain me.
It was a good week.