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

Asking a guy to cum in me knowing he wasnt wearing a condom and I wasnt on birth control.
 
Probably going to adult theaters some years ago and servicing men through glory holes. While my hubby was always present an I never allowed a man to cum in my mouth or pussy it was still risky in a variety of ways. Still some hot memories though:kiss:
 
Our risk . . .

I asked my wife upon returning to me from our overnight-staying dinner guest and close friend's bed in our guestroom, to astonish me with having done some really risky/daring adventure of her own choosing. After waiting anxiously for more than an hour, she returned, climbed up on the bed and passed his cum from her mouth to mine, but then later shyly, proudly confessed she had invited him to have his first climax inside her womb.

Another time, while I listened from outside, my wife spent at least two hours in a car with 4 teenage boys after they had seen her dancing nude under a full moon in a small neighborhood park in North Bay, Marin County, San Francisco. She sucked and masturbated the four to 2 or 3 climaxes each. She returned with me to our car naked, sticky and happy.
 
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Hot, straightforward . . .

HOT! Your expression, ". . . firehosed cum everywhere" says it all!!! Before my wife and I got married, she once said, after I had just sprayed her belly, breasts and face, "I like to be looking right at it, up close, right at the big moment."

Leviticus59 said:
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.
Click to expand...
 
When I was young, single and foolish (not to mention more than a little drunk) I was persuaded to go back to the hotel of a group of lads on a stag do. Just me and seven guys. Yikes.
 
Having sex with two sisters who didn't know about the sex with the other, on the same day within a couple of hours of each other...
 
My first wife and I were swingers, mainly MFM 3'sums.

My wife enjoyed her extra guys but wasn't so much into couples, so in order that i not miss out she had very kindly agreed to me seeing other's, women, couples and men, by myself. She just didn't want the details.

Once I arranged for one of the couples I was seeing to reply to an advert my wife and I placed in a swingers magazine. We eventually met as couples and swapped. My wife never knew that this couple was one of my extras. She would not have agreed to the meet if she had known. I remember how difficult it was to maintain the fiction that we did not know each other.
 
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Highest risk experience for me was

Getting fucked by a guy who had just sucked me off. Then later, after he left, finding the condom he used with a split in the end and his semen coating both sides. Because the guy left so fast, I had no idea if his condom broke as he put it on or as he took it off.

Then going to the health department for STD testing, giving them a phoney name. And then finding out that the person doing the anal swab, urethral swab, and blood testing knew me (so much for anonymous testing). Fortunately I tested negative for clap and HIV (including on a later test), but otherwise, what a "fucking disaster"! I've been more careful and more selective ever since.
 
Felt the risk . . .

The first thing that comes to mind when I want to identify the biggest, riskiest thing I've ever done is easily the phone call I made to a friend who'd wanted my wife ever since meeting her. I told him when I'd be away from home and when she'd be most vulnerable, bought miniature cameras and all the equipment to hook them up, with sound, to my upstairs study computer screen. The cameras I installed in 4 locations in the kitchen, where I knew they'd be. I told the friend that I demanded two conditions of him if he wanted to continue being a friend and if he wanted to ever see my wife a second time. They were, that he couldn't ever let on to her about my involvement, and that he had to tell me all about it afterward. It took some doing to get him to feel comfortable with the proposal, with me, and finally reveal that he was for sure eager to do it. I told my wife nothing. Neither knew I would be witness to whatever happened in the kitchen. For me, it was the hottest thing I'd ever done in our relationship, and the riskiest.
 
I was raised a good girl. Very good childhood, good supportive family. I went to a good college and went right into a good career.

I dated....the guys good girls dated. Yuppie types, "good catches" the kind you could take home to the folks...duds.

Then I went to a bar with a friend to watch her boyfriend play in a dart tournament. I was with a guy I had dated a few times, but nothing too serious. Had sex once...he was more full of himself than I was full of him:rolleyes:

At the bar there's this guy....heavily tattooed, bad attitude, drinking hard, talking trash and ripping through my friend's team. Asshole was saying "Bullseye" before he threw and then hit it every time.

Total ass...but oh goddamn....something about him. He sees me looking and give sme this cocky ass smirk that should have turned me off.

He comes over and says "Hey, green eyes how about a drink?"

My "boyfriend" was sitting next to me, but yapping away like he had been all night paying no mind.

I said, "I'm with someone." he says "Does he know that?" and wanders off, but all night just stared at me like I was dessert after a meal, I"d never had anyone look at me like that God he had me hot

I played hard to get for a bit. Dumped the dud and would show up at the bar and sit and have a drink with him but always back down when he asked for a date he was much nicer when it was the two of us, actually kind of sweet, but he had that aura...he oozed fuck you and he felt like a coiled srping.

I finally say yes, we do dinner and then dancing and of course the fucker can dance we go back to my place I invite him in and swear I'm going to be good, take my time, he's a bad boy and ....

Five minutes in the door my panties are off skirt over my hips and he is fucking em against the wall....

We dated and my family....hated him, he was good to me and fine with them, but I got "what are you thinking, look at him listen to him you're making a mistake. My mother said. "dating him is risky."

Married that bastard:D
 
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