What's the biggest sexual related risk you've ever taken?

Having bareback sex in Russia

I fucked a very nice Russian milf without a preservative. It caused lots of HIV, gonorrhea and other funny tests when I returned home. Thank God, they were all negative. The only thing I got from her was HPV lesion in my tongue that was operated later.

I might have told this story before, can't recall. But when I showed up and she was wearing her cut-offs, it was on. We used to go into her room and she'd sit on the edge of her bed and pull the denim crotch of her shorts over to one side. I'd kneel between her spread thighs and raise myself up and into her. She'd slide off the edge and churn on it as I groped her awesome tits under her t-shirt. We had done this a couple of times but this time, just as I was falling head first (wink, wink) over the fence, we heard the steps of her mom coming up the stairs. I pulled out and it geysered and just wouldn't stop. By the time mom got in the room I was sitting next to her, cock covered by a backpack and we were both looking at our school books. When she left and we began to recover we noticed my protein was dripping from everywhere!

Having bareback sex in Russia

I fucked a very nice Russian milf without a preservative. It caused lots of HIV, gonorrhea and other funny tests when I returned home. Thank God, they were all negative. The only thing I got from her was HPV lesion in my tongue that was operated later.

Went commando in public not too long ago for the first time. I know it's not a big deal to some but for me I fear a wardrobe malfunction happening, even if I wear the right clothes like pants or long skirts.

risky

Not real risky but I've jerked off while riding my cycle.

Well, having read the whole thread, I conclude I must be pretty jaded. Well, okay, I already know I'm pretty jaded~ seems I've done a whole buncha the same stuff people have already listed.

Such as, fucked my sister with no protection. Scared me shitless but we were both so horny for it we went all the way on a few occasions. I always pulled out and firehosed cum everywhere, but some undoubtely stayed in her. I finally ended it (she didn't want to) because of the pregnancy risk, as well as the enormous guilt complex I was developing over it all. Also did lots of various and assorted girlfriend fucking with her parents in the house. Thinking back on it now they had to have known something was going on, but chose to ignore it.

The thing I would like to relate, however, happened much later. I mistakenly married my high-school sweetheart (the one mentioned in the above paragraph). Before we got married she'd flop down and fuck anytime, anywhere, but her sexual switch suddenly and permanently turned to "off" as soon as our honeymoom was over. I was brought up to believe that you stuck with a marriage through thick and thin, come what may. And I did, for 20 long years before finally kicking her to the curb.

Along about year #12, however, I began stopping by adult bookstores just to unload some horniness. Back then the booths took quarters, so I'd pump in two bucks, and proceed to furiously jack off. I could get off twice before the time ran out. Did that for years. The particular bookstore I frequented most had a large, freewheeling booth area in the back. I never loitered around at first, and never paid much attention to whatever else might be going on. Turns out this particular bookstore was very couple friendly, and there was a constant parade of couples through the back, picking up second or third or more guys. Once I finally figured it out, I began hanging around watching the dynamic. Took me a couple of years, but I finally took the plunge and began playing with those couples. I fucked many dozens of those women back in the booths as the years ticked by, never once using any protection. There was also a fairly constant stream of working girls flowing through. Hammered quite a few of them too, sometimes with protection, but mostly without.

I eventually got divorced and met my second wife about a year later. She'd been divorced for about two years, and was having a grand time slutting around pretty frequently. She estimates she had fucked about 15 or so guys between marriages. After we got married and gradually shared each other's history we got thoroughly tested. Unbelievably, neither one of us had ever contracted a single bug.

I had sex with my bf in his car and we were rocking his car and then we heard a BANG and he stopped I freaked a little then he laughed and said it was his antifreeze in the trunk...I was not happy!

Volunteering at Habitat for Humanity, I was distributing drinks and snacks to the guys, and this one young hottie that was remodeling the bathroom upstairs kept flirting with me- then pinned me to the wall and fucked me standing. Two other guys were in the next room, but had their loud electric saw things running. When both saws stopped, we did too, waiting for them to start again. I had cum running down my leg the rest of the day. Saturday, I plan to do it again.

I figure I'll add my own personal sex in public experience. The most recent one, and also the riskiest/most-likely-to-get-us-arrested one.

A few months back the woman I was dating and I decided that it would be a great idea to go to the Boston Public Library on a date. Mostly because we're both huge nerds and like to talk about books, but also because we figured there would be quiet corners to make out in if things headed in that direction.

As it happened, we mostly skipped the talking and went straight to the kissing and the touching. Unfortunately, there aren't nearly as many quiet corners in the library as we thought, so we had to keep moving as people wandered down the various aisles. Eventually we ended up in some corner of the library where we ended up alone, aside from the mumbling homeless guy around the corner, for a sustained period of time. Her blouse ended up pulled open so I could kiss her breasts, my hand was down her skirt fingering her very wet pussy, and her hand was down my pants stroking my equally hard cock.

It wasn't particularly risky up until that point. Then I noticed that she almost had my cock out of the top of my pants, so I figured I'd, uh, help her out by taking it out a bit more. As I did that, she leaned back against the bookshelf, then pulled her skirt up and her panties to the side. I pressed up against her, and slide my cock into her. I was inside of her for about 30 seconds when we heard the librarians cart coming towards us, and hastily tried to cover up. We looked clearly disheveled, for probably obvious reasons, but I'm pretty sure everything was covered up.

She liked it risky

One of the sexually riskiest adventures I experienced was playing with a couple I'd known for a few months. Met them through an underground newspaper in the days before the web. She was a cute little thing..five foot five...a body like a ymnast. She'd even had been featured in the centerfold of Biker Magazine back in the 80's as her hubby was big into Harleys. Her thing was making it in semi public places. It was the thrill of almost being caught. Elevators. Stairwells. Restrooms. Then one night she wanted it on the hood of her car..in the woods..behind the barracks of the State Police. She liked it risky!

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Went to a class reunion at my very small high school. Met up with 3 of my ole high school fuck buddies. We took off early and rode around in a convertible, drinking, and giving each other BJ's. Sometime over ing the early morning, we ended up parked on the city square with me laying over the back seat onto the trunk while my bros took turns fucking my willing ass....I was in heaven!

My submission

While my wife and I have done some daring things. Yes we have done the driving BJ etc. two of my favorites are the strip UNO, where the loser of the game had to strip down and ride home on the freeway totally nude, thank god I won that game. The other is when my wife and I had sex on an Fire Engine. I still think about that. good Times.

I got a blowjob from a coworker in a very public parking lot after a company outing. We both had more than our share to drink and as we were hugging goodbye she felt my cock and just came right out and said she wanted it in her mouth. She was an older, MILFy style woman who loved to stay fit. It was one of the hottest experiences I've ever had. The oddest part is I barely knew her, had only spoken to her at work maybe 5-6 times.

- Fucked my girlfriend in her room while her younger sister and another female friend slept (or didn't) in a bed three feet away.

- Fingered a girl while she picked up a call from her boyfriend and talked to him.

- Fucked a girl in the office, my boss actually.

- After getting done fucking a girl, her phone rang. It was her boyfriend calling to tell her he knew she was cheating on him with me. Lucky for me he was at work.

Hmmm, where to start?

Second time I ever had sex was unprotected. My period was nearly a week late; that was the longest week of my life!

Gave my lover a BJ in the car. We were in town traffic so low speeds. We pulled up at some traffic lights next to a van and the van driver was apparently enjoying watching us (I had to take my lover's word for that since I had my head buried in his lap with his cock down my throat).

Bouncing happily up and down on my lover's cock in the front seat of his (parked) car when a police officer knocked on the window! I jumped so far and so fast I ended up in the back seat! Luckily for us he just gave us a stern talking to.

Been fucked on my boss's desk, and not by my boss. Was having sex in a storage cupboard at work at the same company when someone knocked on the door. Thankfully I'd remembered to lock the door from the inside before bending over and spreading my legs.

At the same company - there was a corridor between two offices with a tea/coffee point halfway along it. There was no door, just a small recess with an l-shaped counter off the corridor. Anyone walking along the corridor could turn off into the recess, it was literally two steps. I was making myself a coffee when the guy I was fucking came in, walked up behind me at the counter, pushed my skirt up over my hips and slid his cock inside me from behind. (I rarely wore panties as I liked to give him easy access.) We proceeded to have utterly silent but incredibly hot sex. Every time we heard footsteps in the corridor we froze, still with his cock buried in my cunt. If anyone had turned off into the tea point we would have been fired - he would barely have had time to pull out, never mind make our clothing decent. Luckily the thrill of the risk was so exciting he shot his load inside me within a couple of minutes and I walked off with my coffee leaving little drops of his cum all along the corridor.

First time I fucked a man who said he'd had a vasectomy felt risky...I wasn't on the Pill so if he had been lying to get inside my pants...

Had sex in so many places outdoors/in public I've lost count...a church doorway, numerous car parks including a couple overlooked by a railway line, in the public gardens of two different stately homes, on a hotel balcony overlooking a golf course, on a train, up against trees while out for a walk, in various public toilets, alleyways, pub doorways, on a picnic table...I like alfresco sex. I've ended up being watched a few times, and once we deliberately parked in the line of a CCTV camera on an industrial estate and had sex over the bonnet of the car.

Not sure how risky this is but it's a thrill: I regularly go without underwear and I love to flash. Petrol stations are great for this, I've flashed my pussy at guys many times accidentally-on-purpose while getting out of the car and if it's a lone male attendant in the shop I sometimes go in to pay with one nipple just peeking over the edge of my low-cut top. I also love to drive with my tits out. Quite often nobody notices, but recently on a long journey a car with four young men in did spot me. We had great fun over the next 40-50 mile stretch of dual carriageway taking it in turns to overtake each other so they could get plenty of opportunities to look at my naked tits. Every time we passed each other I licked my finger and rubbed it on my nipple so they knew I was getting off on it. Somewhere there are some blurry mobile phone photos of a dark-haired woman behind the wheel of a car with her tits on show!

And of course I'm currently playing with fire with my male friend, as mentioned on other threads, at the risk of both of our marriages. If it does end up going all the way, he wouldn't be the first married man I've slept with.

It's odd, I'm very risk averse in life generally, but when it comes to sex, the riskier the better.

Visited a gloryhole, swallowed about 10 loads then went home and fucked my husband. He didn't know.

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I surpose the latest risk was having bareback sex with no protection with a person i dont really know well

I was part of a 25-man gangbang a few years ago. None of us used protection and we all shot off into her. It was so hot I'd do it again.

Spent an afternoon giving head to all cummers at the local cruising area.

I've had unprotected sex with guys I've just met so many times, including one when I was cheating on my boyfriend.

Coza said:

Sounds like you just love a hot creampie.

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I do!

biggest sexual risk?

Playing with my niece's pussy during a family reunion

fasolati23 said:

Playing with my niece's pussy during a family reunion

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i was on vacation...standing in the balcony of a theater with boyfiriend taking me doggy style. just knowing someone could walk in at any moment was so hott.