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

[CeasarBoobage]

It's kinda tame, but I got two for ya.

once the wife and I had sex in the apt complex swimming pool. There were about a dozen people around, and no one seemed to notice. We didn't move much, so it was hard to tell.

The risk factor was higher when we had sex on a picnic table. It was about 3am, but it was in the middle of a huge campground. We were surrounded by the tents housing about 20 people in our group. Our kids, the MIL, siblings, and good friends. We weren't subtle that time though. I don't think we got caught...

 

[badslutmommy]

Helped my sister blow her unsuspecting husband just inside the main gate st a major theme park. Finished cleaning everyone seconds before my husband returned with all the kids.

 

[TalkToMeInSB]

Helped my sister blow her unsuspecting husband just inside the main gate st a major theme park. Finished cleaning everyone seconds before my husband returned with all the kids.

Curious, how was your sister's husband unsuspecting? Blindfolded?

 

[badslutmommy]

Curious, how was your sister's husband unsuspecting? Blindfolded?

At the time he was never involved in any of our escapades. He just happened to be the only one smart enough to bring a jacket incase the weather turned cooler after dark, and kind enough to share with me and sis. As i snuggled up close on one side i asked if this was one of his fantasies? He said not really but it was one of his wife's. So when i saw sis feeling around under his jacket i put my hands there too and it just kind of spiraled from there.

 

[lawless_smurf]

At the time he was never involved in any of our escapades. He just happened to be the only one smart enough to bring a jacket incase the weather turned cooler after dark, and kind enough to share with me and sis. As i snuggled up close on one side i asked if this was one of his fantasies? He said not really but it was one of his wife's. So when i saw sis feeling around under his jacket i put my hands there too and it just kind of spiraled from there.

so thats how you got your name

 

[bill3901]

At the time he was never involved in any of our escapades. He just happened to be the only one smart enough to bring a jacket incase the weather turned cooler after dark, and kind enough to share with me and sis. As i snuggled up close on one side i asked if this was one of his fantasies? He said not really but it was one of his wife's. So when i saw sis feeling around under his jacket i put my hands there too and it just kind of spiraled from there.

my god that's hot

 

[john_johnson]

I think one of the biggest risks I have taken is helped a girl take another mans cock out of his pants to get our threesome going. That was the only time I have ever touched someone else's cock but it really got the threesome going.

 

[lawless_smurf]

Had sex with a with someones wife while she looked through the window making sure her husband doesnt come home

 

[Hans101]

Having unprotected sex with my sister.

Same here.

We were usually very good about using condoms, but went without a few times, which were especially hot.

 

[Beck31]

-----

 

[howdyaccount]

coming home from work with a co-workers pussy all over me and having sex demanded of me right as i got home - just bent her over and did her from behind hoping that she wouldn't smell the pussy and cum on me

 

[beingtrue2me]

Getting married. It did wonders for our sex life and that was not meant in a good way. He was always too tired or gone and because he seemed to lose interest in me I found a fwb and that sort of kicked the snowball down the mountain.

 

[TheLM]

I worked with and hit on/continually flirted with/brewed massive sexual tension with the daughter of a very famous wrestling star.

She was about 10 years older than I.

Her daddy could have folded me into origami!

 

[willyeddy2001]

sexual risk

well until a few yrs ago I didn't think the things I did with a girl I dated were that risky. when I met her I was kinda naïve about sex. back when I was a kid sex wasn't so openly talked about so I didn't know too much. the one girl I started going out with after the military showed me the ropes though. she taught me how to take care of her kinky needs which were mostly oral on her pussy and ass. we'd go parking in my car with the big back seat and get naked and she'd have me eat her pussy til she came a couple times then she'd get on all 4's and put her ass out for me to lick and tongue fuck. she'd have me finger fuck her pussy while I ate her ass and I never knew I could get sick from eating her ass. I know a couple times I got some of her crap on my tongue cause I could taste it but i'd just keep going til she came. i'd be so turned on and didn't know I could get sick and I never did. I've seen a couple threads that talk about how it's not something clean to do but I never got sick from doing oral sex on her and I could even taste dried pee on her full bush as I licked and sucked her pussy. sure she'd shower before I picked her up but we'd go out to eat or have a few drinks at a bar and she'd go pee a couple times so when I went down on her I knew she wasnt' perfectly clean. oh well live and learn. I guess I got lucky.

 

[soflabbwlvr]

I've already posted a few responses to this thread, but here's another one that qualifies. Several years ago I had an unusual relationship with an African-American woman where every time we saw each other, we fucked. I met her at a club and went home with her that night. The sex was great, but I didn't expect to see her again so I didn't bother to get her number. Over the next 2-3 years we ran into each other on about 7-8 random occasions, and we had sex every time.

One morning while I was driving to work I stopped at a traffic light. I looked around, and there she was sitting on a bench at a bus stop. It was a hot summer day, so I honked my horn and waved her over. She got in the car, and the conversation immediately turned to sex. There wasn't any place convenient for us to go, so she directed me to a local park. It wasn't really much of a park, more like a big open field with a few trees. I parked under a huge shade tree about 50 yards from a very busy road during morning rush hour. I went down on her, and then she went down on me, and then we got ready to fuck. We got into the doggy position but she complained that my car was too cramped. She opened the door and walked completely naked to the front of the car. I tried to convince her to get back in the car, but she refused. Instead, she bent herself over the hood and told me to come and fuck her. What could I do? I got out of the car, walked up behind her, and penetrated her. The car was visible from the road, we were in the deep shade of the giant tree, but anyone looking from the road and making an effort could have seen us. We fucked for about 15 minutes before I shot my load and got back into the car. She took her time getting dressed, but after a minute or two she followed and we drove off.

 

[TomBoner]

I was having sex with a girl I was having an affair with. I was married and she was engaged to be married in a couple of months. We worked with each other and over the course of a couple of months the sexual attraction we both felt was just undeniable. Finally just couldn't resist the temptation. One night when we both worked late we finally gave in and locked ourselves into the conference room and made mad passionate love to each other. The next day I was in a meeting in that room and had to hide a pubic hair of hers that was on the table.

The last time we had sex was at her apartment on an afternoon about two weeks before she was going to get married. We were both butt naked and 69'ing on her bed when her fiance entered the apartment. I jumped up and hid in the closet while she threw on a robe and ran and told him she was getting ready to take a shower. He actually walked into the bedroom and stood in front of the closet for about 5 minutes. My heart was beating to fast I was afraid he was going to hear it. Anyway, long story short he finally left, she came back to the closet and saw I still had a hard-on, smiled, dropped to her knee's, and hungrily swallowed one of the biggest orgasms I'd ever had. God I loved how that girl could suck.

 

[kilkennycpl]

scribing for later

 

[aluv]

having sex while driving in traffic. I was 18 and she was 16

 

[lovingfingers]

I was having sex with a girl I was having an affair with. I was married and she was engaged to be married in a couple of months. We worked with each other and over the course of a couple of months the sexual attraction we both felt was just undeniable. Finally just couldn't resist the temptation. One night when we both worked late we finally gave in and locked ourselves into the conference room and made mad passionate love to each other. The next day I was in a meeting in that room and had to hide a pubic hair of hers that was on the table.

The last time we had sex was at her apartment on an afternoon about two weeks before she was going to get married. We were both butt naked and 69'ing on her bed when her fiance entered the apartment. I jumped up and hid in the closet while she threw on a robe and ran and told him she was getting ready to take a shower. He actually walked into the bedroom and stood in front of the closet for about 5 minutes. My heart was beating to fast I was afraid he was going to hear it. Anyway, long story short he finally left, she came back to the closet and saw I still had a hard-on, smiled, dropped to her knee's, and hungrily swallowed one of the biggest orgasms I'd ever had. God I loved how that girl could suck.

Luckeeeeee!

 

[deyv]

In college, had a girlfriend who would invite me home a lot of weekends. Her parents didn't seem to mind.

I was given the guest bedroom that was right next to the parents - she shared her room wiht her sister.... but was downstairs.

So after everyone had gone to bed she'd sneak up to the guest room and we'd fuck with her sleeping parents just down the hall.

I know it wasn't that risky but still - I can only imagine the fallout if we'd gotten caught.

 

[texasm31]

After HS and the first few years of college, I was dating a girl and we had a rather active sex life. For our ages and the time frame (mid to late 80s), we pushed a few limits. Her parents were quite trusting and open, so we'd spend time fooling around in the house with her parents awake in the other room. Usually we kept it mostly clean until they were asleep or we'd go outside or in her room or basement when things got going. But one night we were fooling around on the couch in her living room and she starts giving me head. At one point she looks up and says "just keep an eye on the stairs and if you see feet, let me know that someone is coming downstairs." Fortunately I never saw feet and I'm not quite sure what we could have done if I had, as the stairway was open to the room from about half way down. There would have been no chance for her to get off her knees let alone time for me to "get presentable" as in get my cock back in my pants. Ahh to be young and carefree.

 

[markymark2004]

Sitting watching TV on the sofa with my ex's folks in the room had my hand down the back of her panties sliding a finger slowly in and out and massaging her clit. She got so horny the minute they went out of the room got me to rub her off to a very quick orgasm.

 

[2981notrohrm]

Having anonymous gay bareback sex with a stranger in a bathhouse. Honestly, it was fucking hot.

 

[albertaboy]

Having anonymous gay bareback sex with a stranger in a bathhouse. Honestly, it was fucking hot.

Doesn't get much more high risk than that, you win.

 

[Runr4Life]

The latest, while fucking this woman in the shower at her house, her husband walks in drunk into the bathroom, takes a piss then leaves. We finish up then I left.