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

Probably fucking a girl I met 20 mins ago in my parents' bed, without a condom of course.
 
Hmm Let me think

Had sex with a woman in a hotel room while her daughter was sleeping in the other bed, then went to the washroom once we were done in the bed for round two.

Had the same woman giving me a hand job under a blanket while she had friends over and we were trying to have a discussion.

Sex with the wife in her old bedroom while her dad was in the living room. That was almost too hot. She had to go to the washroom to clean up after. :)
 
I remember fucking a gf in the ass as she spoke to her mother on the phone. Strangely, it made the whole thing a bigger turn on, I hoped she was going to cum whilst on the phone but she controlled herself and ended the call quickly.

Another time, I was fucking her in her parents' lounge - she was kneeling in front of the sofa and I was fucking her doggy style. It was a quick 'skirt up, panties down' sort of thing

We heard their car pull into the drive but I carried on and quickly came in her pussy. Once I'd done this we quickly pulled up our respective underwear and sat down.

The gf had a hard time sitting there talking to her mum with my cum dripping out of her and soaking her panties.
 
Do you still have sex with your sister Hans ?

Thnaks for sharing deep secrets guys .. Keep it coming :)

Made love to my sister and came inside her without any kind of birth control.

Only happened a few times, and then only because we didn't have condoms but just couldn't stop ourselves.
 
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the biggest sexual related risk I've ever taken???

the 1970's...
 
I once fucked my wife on the roof with traffic going by. Anyone could see us if the looked up our way.
She loved the fact that we were being watched and came super hard all over my balls.
 
Sex in my bedroom with my dad in the next room. Sister almost caught us but we threw a blanket over our lower bodies just in time.

Sex in my bf's room while his mom was just on the other side of the door.

Showing off our new boobies and kissing in yard between the houses. Anyone looking out of either could have seen us.

I let someone cut me and lap at the blood - it was oddly sexual.
 
I did something very risky and stupid.

Met a couple of guys in 7/11. Then we went behind the building and they fucked and came in me. Didn't know either of them and never got their names.
 
One that comes to mind...

Ex-wife and I at her aunt & uncle's house, on their family room couch under a blanket while her aunt, uncle and cousin were literally on the other side of the wall in the kitchen.

Might add some others another time...
 
Lots of public sex and showing off and unprotected sex. Sigh -- the danger is what causes the rush.
 
I know this is terrible, but my boyfriend and i (when i was in my last relationship with my ex), had anal sex in my ex's bed while he was away and we accidentally fell asleep afterwards. Woke up to my ex standing next to the bed. Luckily before falling asleep we got dressed and were laying on outside of the covers so told him we fell asleep after work watching a movie.
 
I has sex with a guy, then he went out and i shagged his brother in his bed. he came home and slept in that bed with his brothers scent in it
 
My wife has given me many memorable blow jobs but there are three that stand out in my mind.
Driving on the 400 Hwy. north of Toronto on a Saturday afternoon with traffic all around us.
Driving through the Florida Everglades on the Alligator expressway.
After dropping a load at the dump, She sucked another load out of me.

Ahhh ... memories
 
dad watched his daughter getting some

While swimming in an above ground pool my gf and I were having a conversation with both her parents who were sitting 30 feet away. I got behind her and casually slipped my cock past her suit and into her pussy. She tried to push me away but didn't want to make a scene. I fucked her slowly for several minutes.
 
Licked my girlfriends pussy while she had a conversation with her parents. They were in the living room we were in the kitchen about 10 feet away!!
 
Let me know if this doesn't fully count:

During a college fling I had with a separated & soon-to-be-divorced older woman, she drove me to "this house" for a nice weekend alone together. It turned out to be her old, and husband's current, house. We fucked all over the place, hottest was on the back porch (bent her over the railing) and she wasn't quiet at all. Pretty sure the the kids nextdoor got their first XXX scene shot.

Divorce went final that following Monday
 
When my wife was visiting her sister in Florida, a guy that I have been giving blowjobs came to my house and brought one of his friends with him. My wife picked that moment to telephone me while I was on my knees sucking both their cocks and I kept up an extended conversation with her as I continued giving them blowjobs. I told her that I was eating a banana to explain the sounds I was making with the cocks in my mouth. One of them even came in my mouth and I swallowed as she was talking to me. The two guys were biting their fingers to keep from breaking up.
 
My wife has given me many memorable blow jobs but there are three that stand out in my mind.
Driving on the 400 Hwy. north of Toronto on a Saturday afternoon with traffic all around us.
Driving through the Florida Everglades on the Alligator expressway.
After dropping a load at the dump, She sucked another load out of me.

Ahhh ... memories


Too funny!!!

We were taking our motorhome up the 400 to our place in Muskoka to use as overflow guest accommodations for an upcoming family event there, the wife got horny and it was a warm holiday weekend Friday night, lots of traffic, so she peeled of all her clothes and started rubbing her pussy. That got her even hornier so she sucked me hard and then impaled herself on my throbbing cock as we crept along at about 40 km/h.

I suspect I wasn't keeping the straightest line because an OPP officer (female too boot!!!) puled me over to ask if everything was ok, or if I'd been drinking. The motorhome is sofar up she couldn't see anything so my wife dropped down and while I was talking to the cop she was kneeling over my cock and sucking me for all she was worth while stroking her pussy desperate to get off, she'd been really close when the cop pulled me over.

Her pussy was so wet and she was slurping my cock so loud I was sure the cop could hear what was going on, but she bought my story of grooves in the road from transport trucks causing the motorhome to wander a bit and left.

Before we pulled away I bent her over the arm of the sofa and pumped a huge load into her with 100's of cars a minute rolling past.
 
Besides having a few pregnancy scares when I was young, before I started the Pill. My husband and I dated for 10 years before we got married (met when I was in HS), there were lots of times of him fucking me while my parents slept in the next room.

Once, probably about 6 years ago, it was the middle of the day so I thought no one was home. We started doing role-play of one of his fantasies of non-consensual sex. So I was being very vocal and loud. About an hour after we finished, I heard my brother come up the stairs from the basement and leave to go to work. I was mortified! There is no way he couldn't have not hear us, but never said anything about it.

But I would love to try more risky things. Maybe a threesome with my hubby or some "accidental" public flashing. My libido is really messed up right now, probably from medications. I want to be "in the mood" more often.
 
My wife has given me many memorable blow jobs but there are three that stand out in my mind.
Driving on the 400 Hwy. north of Toronto on a Saturday afternoon with traffic all around us.
Driving through the Florida Everglades on the Alligator expressway.
After dropping a load at the dump, She sucked another load out of me.

Ahhh ... memories

Was that YOU on the 400????
;)
 
Circle skirts, remember them??

At my gf's house in the late 70's, she used to wear a large black circle skirt, loads of fabric and pleats. She returned from the bathroom and gave me her soaking panties, opened my flies and worked my cock hard (not that it needed much work by then) and sat over me as I sat on the couch. Parents in the next room and as she started to hump me the door opened. She stilled and we looked like a couple, her sat on my lap, as her mum went through into the kitchen, made tea, all the time my cock is stuffed into her daughters wet pussy. Tea finally made, cock sliding out a little before g/f started to tease and move to get it hard again and I finally came in her whilst the parents were in the other room watching tv..... Mmm, wonder where she is now, would like to try that one again!
 
Most recent thing with a lover. She dared me to wear stockings under my work clothes, no socks. Promise of anything I like if I could do so and prove it - so duly purchased hold-ups and wore on a train, and into an office. Sitting down it would be clear that the black fabric around my ankles was not socks. No underwear either, was quite an arousing day, even went out to the shops, really enjoyed the sensations and the riskiness.

Reward? Mmm, we both enjoyed her first facial, but that was in private!
 
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