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

After my first divorce, I was still pretty young, and just gotten over the whole thing. I got invited to a party of one of my ex's friends, and learned he was going through a tough break-up. I was drinking all night long, as was he, and I decided to have "mercy" sex. Not only for him, but that it might get back to my ex husband of what I did. He was a great man in bed, and we fucked all night long. A couple of times we snuck off to the bedroom during the party. He said he always wondered what it would be like to fuck me, so there wasn't a whole lot I didn't let him do. I knew it would get back to my ex husband of how he fucked me, this guy could never keep a secret.

Many, many more stories, but this one made me smile thinking about it again.

Tifani
 
Oh Tifani............if I'm having a bed day, you'll just to come here and cheer me up!!
 
Sex with my female boss at the office in the middle of the day, with people in the hallway. (Door closed though.)

Fingering a FB while she took a phone call from her live-in boyfriend, at their house.

I also slept with an engaged woman for several weeks, though I didn't know the risk at the time because she did not tell me until later. (Her fiance lived in the UK.)

Something about "off-limits" women - they always find me. :devil:
 
military days..

I was a straight up whore when i was in the marine corps...

I would go around base housing fuckin wives of fellow marines. Most of them loved having me cum inside them they would get a rush from it saying that they were gonna have their MSN fuck them with my load still inside them..

I think back on it and was lucky i didn't get shot. We're a crazy bunch of fucks
 
Junior year abroad

When I was 20 I went on a junior year abroad to the UK. Soon after I arrived I met this British guy and he was my boyfriend for all the time I was there. He was really nice, but very inexperienced. Actually, he was a virgin and I told him I was one too, although I had been with about ten guys by then. He believed me too for some reason or other.

Anyway, all the time I was there I yearned for being really fucked properly. So I would cheat on him all the time,mostly with complete strangers. For the eight or nine months I was gone I probably did it with an additional ten guys.

I'd usually go to a pub and let myself get picked up and then go to the guy's car and fuck. One night these two brothers took me to their apartment and they both had me. I never saw any of these guys again.

Then the next day I would be sweet and demure for my boyfriend. I really look like the girl-next-door type and no one ever guessed what a slut I was in London.
 
hot!

When I was 20 I went on a junior year abroad to the UK. Soon after I arrived I met this British guy and he was my boyfriend for all the time I was there. He was really nice, but very inexperienced. Actually, he was a virgin and I told him I was one too, although I had been with about ten guys by then. He believed me too for some reason or other.

Anyway, all the time I was there I yearned for being really fucked properly. So I would cheat on him all the time,mostly with complete strangers. For the eight or nine months I was gone I probably did it with an additional ten guys.

I'd usually go to a pub and let myself get picked up and then go to the guy's car and fuck. One night these two brothers took me to their apartment and they both had me. I never saw any of these guys again.

Then the next day I would be sweet and demure for my boyfriend. I really look like the girl-next-door type and no one ever guessed what a slut I was in London.

Are u still a slut now?
 
That would be when I was fucking the wife of a student of mine.
 
caught with gf

I went with my gf at the time to her family lake house. Her mom caught us totally getting it on. She told my gf to dress and leave and I was there totally naked with a wet boner. She made me finish it off while she watched and then had me do the same thing every day until we left so she could be sure I wasn't running around with a hard on constantly trying to screw her daughter. Backfired. made me twice as horny!
 
I was a guest at a house dinner party. The wife of the host and I fucked in the master bathroom 3 times that night. Her husband told me later he knew what was happening, and wanted to approach me about a threesome. Worked out great! I just didn't know it while I was fucking her......
 
I agree with the freedoms of not wearing anything condom etc. Beautiful feeling to be one with someone without anything separating you, even a thin piece of latex.

Risky....12 yrs ago, on the beach at night under a deck with people above but could not see as the deck boards were tight but still felt like you were being watched. Other was on a dock, again in my twenties, at a lake with a pretty older lady (22 yrs older) i met a night before, had some drinks so long blowjob and sex, who knows if anyone watched did not care was having fun and tipsy too. And of course a couple married women, I did not know at the time but where beautiful lovers, so if I knew I still would have gotten inside them.
 
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Met a guy from Lit, in his hotel room. We fucked. Without condoms.

Risk was outweighed by fucking awesomeness :heart:
 
I've engaged in a lot of risky behaviors--too many to count. But I would say the riskiest was having sex while driving. I was young and stupid, and my girlfriend and I had sex every chance we could. One night we were driving home from a drive-in theater. She was naked and laying across the front seat of the car. I was driving and sliding a dildo in and out of her pussy. She got so horny that she pulled down my shorts, climbed onto my lap, and slid down my pole. I could barely see over her shoulder while she bounced up and down on my cock. After about two minutes I came, and she finally crawled off me. I was doing 20 mph on the interstate at that point. Luckily, we were the only car on the road and there were no cops in the vicinity.

Why does everyone think this is risky? It happens everyday all over the world, i have done it thousands of times, and have never even had a close call. I have never heard of a verifiable case of anyone being hurt this way. I do personaly know a guy who was killed by a couple kissing while driving.
 
Why does everyone think this is risky? It happens everyday all over the world, i have done it thousands of times, and have never even had a close call. I have never heard of a verifiable case of anyone being hurt this way. I do personaly know a guy who was killed by a couple kissing while driving.

Once was enough for me. Road head -- no problem. Road fucking -- never again. (It's not really a genuine issue any more. I couldn't squeeze a grown woman between my body and the steering wheel like I could when I was 18).
 
Risky behavior

According to these posts i have also done too many risky ones to count. My son just asked me an unrelated question that reminded me of one that could have gone wrong and caused a bit of commotion though.
My family and my sisters family went to Magic Mountain, a theme park in southern california for those who don't know.
As the evening was drawing to an end and the night was becoming cold, we decided it was time to round up the children and head for the cars.
As my husband headed back to the ride the kids were rideing over and over, sis her husband and i sat on a bench near the front gate. Being southern calli beach babes we were not dressed for the cooler mountain night air, so her husband; a pretty big guy took off his jacket and the three of us snuggled together under each of his arms.
Sis and i have an undeclared competion at times to be the more adventurous faux exibitionist, so she soon unzipped his pants under the jacket. I caught a glimps of something going on under the jacket but knew for sure when i overheard him whisper;"you better be careful", then, "yes but your sister might not want to see him right now!". When he told her, "you wake him up and you are going to put him back to sleep"; i knew she had his cock out.
I began to feel around under the jacket to see if i was right and imediately felt two small hands and a large cock. Naturally when she felt my hand and knew i knew she decided to show off and stuck her head under the jacket. As i was feeling her lips between my fingers trying to suck in the head of his penis, he looked at me shook his head chuckling and said, "she is just showing off for you."
That is when i decided to get even and dove under the jact and putting my cheek against hers pushed her off and began an ernest attempt to deep throat him. After what seemed like seconds but actually was a bit over 30 minutes , he came a big load that she could not contain, and spilled on all of us. To add a bonus i slurped the cum off her and was licking it off his pants and her hands when he spotted my husband and the kids approaching.
I explained to my husband i had dropped my keys and was trying to recover them without anyone having to leave the warmth of the jacket.
 
According to these posts i have also done too many risky ones to count. My son just asked me an unrelated question that reminded me of one that could have gone wrong and caused a bit of commotion though.
My family and my sisters family went to Magic Mountain, a theme park in southern california for those who don't know.
As the evening was drawing to an end and the night was becoming cold, we decided it was time to round up the children and head for the cars.
As my husband headed back to the ride the kids were rideing over and over, sis her husband and i sat on a bench near the front gate. Being southern calli beach babes we were not dressed for the cooler mountain night air, so her husband; a pretty big guy took off his jacket and the three of us snuggled together under each of his arms.
Sis and i have an undeclared competion at times to be the more adventurous faux exibitionist, so she soon unzipped his pants under the jacket. I caught a glimps of something going on under the jacket but knew for sure when i overheard him whisper;"you better be careful", then, "yes but your sister might not want to see him right now!". When he told her, "you wake him up and you are going to put him back to sleep"; i knew she had his cock out.
I began to feel around under the jacket to see if i was right and imediately felt two small hands and a large cock. Naturally when she felt my hand and knew i knew she decided to show off and stuck her head under the jacket. As i was feeling her lips between my fingers trying to suck in the head of his penis, he looked at me shook his head chuckling and said, "she is just showing off for you."
That is when i decided to get even and dove under the jact and putting my cheek against hers pushed her off and began an ernest attempt to deep throat him. After what seemed like seconds but actually was a bit over 30 minutes , he came a big load that she could not contain, and spilled on all of us. To add a bonus i slurped the cum off her and was licking it off his pants and her hands when he spotted my husband and the kids approaching.
I explained to my husband i had dropped my keys and was trying to recover them without anyone having to leave the warmth of the jacket.

Competition between sisters is a good thing :devil:
 
Just thought I'd post to say this thread was a great read - and has encouraged my partner and I to perhaps trying some different things in the future ;) I unfortunately have no interesting stories to tell..nothing risky or dangerous in my sex life history as far! :eek:
 
In my twenties I worked for a small family owned business, ended up having a affair with the wife and we would fuck on the second floor stock room while her husband and family worked below!
 
I have 2 like others have posted I'm sure. I didn't read the whole thread completely.
Did a then gf in the kitchen while her grandparents were in the living room about 15 feet away. Did her doggy style on a chair.
Other time was doing another gf in my room while my parents were asleep in the other room next to mine. Walls were thing but never got questioned about it.
 
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