Your most taboo/risky sex?

[funkyfitter]

#1 Miss Sue fucked my sister's ex and his cousin.
#2 Miss Sue fucked my brother's sister in law's stepson.
#3 Miss Sue was flown down to the Keys by two guys that she fucked in New Orleans where her and another guys wife fucked them and their friends.

[MarknSusan]

I had a fair amount of risky sex over the years and here is another experience.

I fingered my gal pal on a couch at night while her boyfriend was about 3 feet away lying down on the same couch, talking to me (facing away)! Susan was already in bed and in the morning when I told her what I did she told me I was crazy to try that.

But my gal pal loved it!

[sw6]

I had been chatting with a lady who turns out hadn't moved to this country yet. Her hubby was here however. My (ex) HW spent some time with him, MFM with me as an introduction
We all went to dinner when she arrived
I dragged her into the bathroom at the restaurant, one in the back that was just being used for storage. It had a urinal that went to the floor which was part of my plan as I knew she was into pee
As i started to get her to give me a BJ my ex was blowing up my phone for pics, which I couldn't pay attention to. Her hubby was saying nothing would happen as she had never done something like that before (she had done a lot!)
She was saying "no we can't, we shouldn't" while letting me stuff my cock down her throat - I sensed she was up for it
The only thing was I didn't end up using her/the urinal, a later disappointment

[marine20]

years ago when i was still working in a warehouse , a woman that worked in the office there , would come by my car in the morning in the parking lot. i was finishing up my coffee before heading in to work. she always poked her head in my car to say hi , then she walked in to the office. i thought it would be funny to have my cock hanging out when she came by. she laughed , but also became turned on. so next morning i made my cock hard before she came. she loved it and stroked it for a few seconds. we did this every morning . then i put a hidden video camera in the car and taped her jacking me. it was great . i still have the tapes which came out great. funny part is , my wife got a job there and they became friends . this was a long time ago , and they are still close.

[Funcpl500]

Our most risky sex you can read about in the story in the library called ‘the breeding of Jill’, where her long term partner and Jill risked possible pregnancy.

[Jaylatino83]

I love risky sex as having sex with married women and the husbands don’t know. It’s very hot sex that way, and always seems to get dirty and vocal. I bust fat loads when I fuck taken women.

[aliefguy]

I use to fuck and cum inside a friend of mine in her garage while her family and husband were in the house.

I let my friend and his son (adult son) have sex with the wife. They take turns with her and always cum inside her.

[mfmfantasy50]

Prelude: This is a completely true story. On the surface it seems innocent enough; given the wild stuff that happens today. But, if the one third party character in this story had been so inclined, he could've revealed us and caused reputational damage, embarrassment and problems with our family, friends, and professional acquaintances, that would have very likely upset the delicate balance of our standing in our community. Then, in addition, we were then and still are potentially vulnerable to coercive behavior that could lead to expectations of certain other "favors" from us for his continued "silence." With all that in mind, here is the crazy true story of what we did...


The Painter Watches Us Fuck

We had a patio cover rebuilt after the old one blew down in a hurricane several years back.

We found carpenters and a painter through a close neighbor's references and made contracts for completion.

The finishing painter was a very close personal friend of the neighbors'. The painter was a former football player, quite large, very athletic, and very handsome. He was almost immediately very friendly with my wife, as she uncharacteristically remarked he was a "very attractive man" and that she liked big men. He proposed an afternoon appointment on the coming Saturday to paint the completed carpentry work to match our house trim colors and we accepted.

We had a "busy" Friday night with friends and after that welcomed the chance to sleep late on Saturday morning to recover before the repair work got underway. We were both sleeping very soundly “snuggled up” at 7AM, when we were startled awake by loud rattling and clattering of ladders being set up on the patio right outside the uncovered wall to wall windows that overlooking the patio and the swimming pool from our Master Bedroom!

My wife woke quite angrily expressing shock and dismay that the painter was there so damned early without giving us any warning; catching us in in bed and in our pajamas in our kingsized bed that was of course in full view from the huge uncovered windows!

I suggested we just get up quickly, rush into the bathroom and get dressed, while we still had a chance, and before the painter climbed up to his elevated position on the ladder; just a few feet away with a full birds-eye view of the entire master bedroom; kingsized bed and all.

I was laying on my back under the covers as my wife surprised me rolling over and declaring angrily “IT IS TOO DAMN LATE!”

As she ducked completely under the covers facing my side, with her back turned towards the uncovered windows, I could see the painter had climbed up to his working perch seeming to act as if he didn't know we were even there.

My wife was still fiercely angry at what she perceived was the painter’s rude interruption of our privacy and so she defiantly announced she was not going to let him “…RUIN OUR SATURDAY MORNING!”

Before I could ask what she meant by that, my wife moved her hand caressingly up and down my stomach before settling it on my cock and balls under the covers. I stared straight into the eyes of the painter, who was now smiling down upon us from atop the ladder just outside our bedroom window!

My wife's caresses caused me to catch my breath as my wife squeezed my balls firmly in my gym shorts.

I stuttered, “Ah-ah ooh David is watching!” My wife responded emphatically and loudly, “I DON’T CARE! I'M GONNA MAKE HIM WATCH!”

I saw another broad smirk on the painter’s face as he watched down on us, while pretending to ignore us and apply caulk to the fresh woodwork.

My wife kept working fully under cover and grasped my left hand to force it towards her nether region; causing me to roll over facing her and the now-grinning painter, who was no longer focused on the caulking work.

Though I couldn't see whether he had a bulge in his trousers, I suspected he did and that he wouldn’t be able to hide his obvious reaction to our “playful sexual” activities.

My wife was making us steamy under the covers. So, she shed her blouse and shorts tossing them out and onto the floor. I began touching her nakedness and felt her tugging my shorts down and taking my t-shirt off.

In an instant, she had us both completely naked under the covers a few feet away from the now widening eyes of a painter we knew; only because he was very close friends with our neighbors?!? Fuck, he was even breathing heavily through his slightly open mouth!

Having addressed to heat under the cover for the time being, my wife turned her attention back to the “FOREPLAY!”

As she rolled and tumbled up against me keeping us BOTH VERY AROUSED, the placement of the bed covers were under stress and got pulled around a bunch!!! The cool air was now rushing in from the sides of covers and from the top edge; feeling very refreshing, and my wife seemed unconcerned that her naked shoulders and back were now on display to the painter’s gaze!

Besides that, she was really getting overly aroused?!?! Her pussy was drooling juices all over my naked legs and I was easily able to push three fingers into her slippery gash!!!

I was very aroused, too, of course, as she tugged on my cock and balls quite aggressively; making pearls of precum form on my cock head only to be pressed into the progressively dampening sheets.

This was our increasingly erotic condition as my wife tugged my cock and balls towards her trimmed pussy mound; giving the signal that she wanted me to fuck her!!!

But, I was very cognizant that getting into the “MISSIONARY” position was going to cause the covers to come down much further all around our naked bodies…

Anyway, as I feared my enthusiastic wife would pull my balls OFF, if I didn’t follow orders, I reluctantly make adjustments to be able assume the missionary position when needed! So, as she rolled onto her back and spread her legs outside the covers, I lifted my left leg over her lower body and maneuvered to be straddling her legs and waist with my upper body lifted to expose her breasts. At that point I felt her grasp my hard cock and begin to guide the stiff drooling shaft of six inches towards her sloppy wet loose pussy lips!!!

I glanced down between us and saw my wife’s naked breasts and erect nipples fully exposed in the several inches we were separated. Moving into a missionary position had set up a sort of sheet-slide that was working its way down my back pretty quickly! So, the painter was getting a better and better side view of my wife’s beautiful perky tits and hard nipples, as the covers slid more quickly down my back towards our compressed naked hips!

I tried penetrating her vagina from the position straddling my wife’s hips, but my six inch cock wasn’t long enough to reach her hole. So, I lifted up higher, again, pushed my wife’s legs as far apart as they would go, and got down between them, raising my torso and pushing my cock up between her legs, which got me inside her extremely aroused pussy causing her to moan really loudly.

I flinched at my wife's loud moaning; though I don't know why. After all, all pretenses of being discrete were gone, now. It was becoming impossible for us to hide from his gaze??

I should've been more concerned about the bed covers that got forced down to my ass by the last maneuver; because they left us both totally exposed from our heads to below our ass cheeks. What a delicious sight we must’ve presented for the likely horny painter?

At that point my wife lifted both legs and dropped them outside and on top of the covers; exposing her gorgeous long legs and full nakedness from head to toe. Only my feet were still slightly under the covers and I just gave up and used my feet to kick off the final thread of covers.

There we were; naked from head to toe and bound in a loose and exposed MISSIONARY FUCK!!!

My wife in a loud primal growl commanded me, “FUCK ME!” I’m sure the painter heard her assertive directive through the glass!!!

I followed orders pushing and pulling and lifting off her torso to look down as my cock went in and out of her beautiful slippery shining pussy. Her right hand snaked between us to claw angrily at her clitoris and we pounded repeatedly for several minutes with her legs gradually lifting to unsuccessfully try to wrap around my ass; until she suddenly screamed out and began the continuous kicking violent most incredibly physical orgasm I've ever seen her enjoy….

I was only a split second behind her; totally hypnotized by the taboo nature of our shared indiscretion. After a few more penetrations, I held my cock as deep as my six inches would allow and filled her pussy with a HOT load sending jets of cum to overflowing, before feeling it flooding back out of her contracting and clinching pussy….

Then, we both collapsed and she began to come down from the uncontrollable quivering and whimpering…

We laid there naked for quite a few minutes, perhaps even napping a bit and then I began to slowly pull the covers back over us.

Through the whole session, the painter never once stepped down from the ladder to give us any privacy…. And not once did he avert his gaze from our naked bodies locked in passionate fucking.

More importantly, though my wife is normally a very modest dresser and very cautious about showing skin, throughout this entire sexual exhibition, she never once took action to hide her precious beautiful nakedness nor our very private raw sex from the watchful painter.

There ends the drama of the story...

But, given we had never before nor have we since performed such an exhibition for anyone else, I’d love to hear the readers' ideas on what you think contributed to this over-the-top sexual show on this particular occasion?

Another thing…. I would ask the readers to speculate on what if anything you think the painter told his friends and our close neighbors, after what he saw?

When I went out later in the morning, I was a bit shy, as I politely greeted the painter to discuss completion of the painting. This big man had a HUGE “shit-eating grin” painted across his handsome face…. So, I admit I was a very intimidated and quite flustered by his apparent confidence and open celebration of what he probably thought we did for his singular enjoyment and entertainment earlier that morning.

I should note, I took no action that would have caused a scene, accelerated his departure or obtained any satisfaction for his perceived transgressions as they experienced by my wife.

FIN

[rnmiller96]

Insertive vaginal sex while driving a car.

[sema]

We’ve only just got into this ‘hot wife’ thing and I really don’t know what else is in store. Even so, there’s already been quite a dramatic turn of events in this short space of time.

My girlfriend Lisa, who’s in her twenties, blonde, slim and very pretty, had a teacher at school whom everyone had a crush on. She’s now seduced him, or perhaps he seduced her, and as far as I know, the fact that he was once her teacher plays a big part for the two of them.

Not only that, but this teacher, with whom she has sex from time to time, because they simply don’t see each other that often, is currently also having an affair with my aunt, my mum’s younger sister. As a child, I spent a lot of time with my aunt when my mum was back at work. So I’m very close to my aunt.

In other words, my girlfriend Lisa is sleeping with the same man with whom my married aunt is having a secret affair.

[Natatude]

For years, I would have sex with my lover and never wore a condom, I’ve been with him nearly 31 years. Hubby and I have one daughter she was 6 back then when we started. He would be at our house frequently having 3somes, of course when our daughter wasn’t home during the sex, however we had cookouts and what not and always invited him. So she knew him as uncle Paul and he treated her like she was his! my whole family knew him and thought he was just my best friend, if they knew we have sex, they would call me disgusting and disown me. I never got pregnant anymore. Wasn’t on any type of birth control. I am now post menopausal, our daughter is 37 now and married and has 2 kids 12 and 10 and they also know and love uncle Paul. And he spoils them. It was and still is a huge risk.

[Natatude]

In other words, my girlfriend Lisa is sleeping with the same man with whom my married aunt is having a secret affair.

Does your wife know, that you know that? And does she know he’s also having sex with your aunt?

[Michael0001]

Natatude, I really liked your post. It is interesting how long-term lovers become integrated into our daily lives--heart-warming really.

[MarknSusan]

For years, I would have sex with my lover and never wore a condom, I’ve been with him nearly 31 years. Hubby and I have one daughter she was 6 back then when we started. He would be at our house frequently having 3somes, of course when our daughter wasn’t home during the sex, however we had cookouts and what not and always invited him. So she knew him as uncle Paul and he treated her like she was his! my whole family knew him and thought he was just my best friend, if they knew we have sex, they would call me disgusting and disown me. I never got pregnant anymore. Wasn’t on any type of birth control. I am now post menopausal, our daughter is 37 now and married and has 2 kids 12 and 10 and they also know and love uncle Paul. And he spoils them. It was and still is a huge risk.

Natatude, IMO, this is a wonderful story. Thank you for sharing.

With respect to your comment about “disgusting and being disowned”. We had a somewhat similar relationship with Susan’s first love. He was also a very good friend of mine and the three of us hung out, did sports together and also traveled together. Susan and he continued to have sex off and on (off when he was in a monogamous relationship) for more than 40 years.

In our experience, people do observe other’s relationships and can often sense when there’s something else going on in relationships. For years many of our close friends and our three boys asked us probing questions and at one point we both came out of the closet and told certain friends and our family that we are non monogamous.

Almost everyone we told responded with a comment like “we knew it!” Some even mentioned that they were envious that we had a relationship like this. Our good friends and family all know it accept us for who we are. We have a loving relationship, are respected in our community and in the business world and to the extent we know we have never lost a friendship because of our lifestyle. If we have, we don’t care. We are who we are, we love each other and love our family and friends.

IMO, you should feel no shame whatsoever having a relationship where you shared love with someone else, in an honest and open non cheating relationship.

[Long Lurker 34]

For years, I would have sex with my lover and never wore a condom, I’ve been with him nearly 31 years. Hubby and I have one daughter she was 6 back then when we started. He would be at our house frequently having 3somes, of course when our daughter wasn’t home during the sex, however we had cookouts and what not and always invited him. So she knew him as uncle Paul and he treated her like she was his! my whole family knew him and thought he was just my best friend, if they knew we have sex, they would call me disgusting and disown me. I never got pregnant anymore. Wasn’t on any type of birth control. I am now post menopausal, our daughter is 37 now and married and has 2 kids 12 and 10 and they also know and love uncle Paul. And he spoils them. It was and still is a huge risk.

Natatude, IMO, this is a wonderful story. Thank you for sharing.

With respect to your comment about “disgusting and being disowned”. We had a somewhat similar relationship with Susan’s first love. He was also a very good friend of mine and the three of us hung out, did sports together and also traveled together. Susan and he continued to have sex off and on (off when he was in a monogamous relationship) for more than 40 years.

In our experience, people do observe other’s relationships and can often sense when there’s something else going on in relationships. For years many of our close friends and our three boys asked us probing questions and at one point we both came out of the closet and told certain friends and our family that we are non monogamous.

Almost everyone we told responded with a comment like “we knew it!” Some even mentioned that they were envious that we had a relationship like this. Our good friends and family all know it accept us for who we are. We have a loving relationship, are respected in our community and in the business world and to the extent we know we have never lost a friendship because of our lifestyle. If we have, we don’t care. We are who we are, we love each other and love our family and friends.

IMO, you should feel no shame whatsoever having a relationship where you shared love with someone else, in an honest and open non cheating relationship.

M&S
- That was me. Well even to this day still wondering. A buddy of mine had close neighbours. The husband was a part owner of a firm and extremely frequently 'Steve', one of his employees, would also be at their house. Like stay entire weekends regularly, some times even when 'Ted' was away. And this was something that went on for decades. Arsino Hall moment - HHHmmmmmm!!

[sema]

In other words, my girlfriend Lisa is sleeping with the same man with whom my married aunt is having a secret affair.

Does your wife know, that you know that? And does she know he’s also having sex with your aunt?

I`m not married. My girlfriend is sleeping with her teacher crush.

[CleanUpGuy]

I worked with a woman who was the same age as me, late 20's, and we teased a lot. My wife was very wary of her and told her to stay clear of me. Well, over ten years later, at age 40 we met up for a weekend of intense sex. She had the most fantastic looking pussy I've ever seen, it was tight and made me come in waves. That was over 30 years ago and it is still a secret, it is my only encounter with a woman that my wife would be very unhappy with. I occasionally talk to this woman, no heat there anymore but we both still remember it.

[Thebestdays1]

My now, ex wife's ongoing incestuous relationship with her sisters and her nephew has to be top of the list of the taboo things she's done.

As far as risky; she was coming home on a train with a boyfriend late one night and they were trying to have sex but the train stopped at every station so they had to stop in case someone got into their carriage. By the time they reached our home station they were both feeling a little frustrated so when the train left the platform he bent her over a bench by the ticket office and fucked her like that until they both came. A week or two later she and I boarded a train and sat down opposite the ticket office and I nudged her and pointed to a security camera pointing towards the door and bench. This was new so I don't know if it was there when she was being fucked but I like to think so.

[MarknSusan]

For years, I would have sex with my lover and never wore a condom, I’ve been with him nearly 31 years. Hubby and I have one daughter she was 6 back then when we started. He would be at our house frequently having 3somes, of course when our daughter wasn’t home during the sex, however we had cookouts and what not and always invited him. So she knew him as uncle Paul and he treated her like she was his! my whole family knew him and thought he was just my best friend, if they knew we have sex, they would call me disgusting and disown me. I never got pregnant anymore. Wasn’t on any type of birth control. I am now post menopausal, our daughter is 37 now and married and has 2 kids 12 and 10 and they also know and love uncle Paul. And he spoils them. It was and still is a huge risk.

Natatude, IMO, this is a wonderful story. Thank you for sharing.

With respect to your comment about “disgusting and being disowned”. We had a somewhat similar relationship with Susan’s first love. He was also a very good friend of mine and the three of us hung out, did sports together and also traveled together. Susan and he continued to have sex off and on (off when he was in a monogamous relationship) for more than 40 years.

In our experience, people do observe other’s relationships and can often sense when there’s something else going on in relationships. For years many of our close friends and our three boys asked us probing questions and at one point we both came out of the closet and told certain friends and our family that we are non monogamous.

Almost everyone we told responded with a comment like “we knew it!” Some even mentioned that they were envious that we had a relationship like this. Our good friends and family all know it accept us for who we are. We have a loving relationship, are respected in our community and in the business world and to the extent we know we have never lost a friendship because of our lifestyle. If we have, we don’t care. We are who we are, we love each other and love our family and friends.

IMO, you should feel no shame whatsoever having a relationship where you shared love with someone else, in an honest and open non cheating relationship.

M&S
- That was me. Well even to this day still wondering. A buddy of mine had close neighbours. The husband was a part owner of a firm and extremely frequently 'Steve', one of his employees, would also be at their house. Like stay entire weekends regularly, some times even when 'Ted' was away. And this was something that went on for decades. Arsino Hall moment - HHHmmmmmm!!

No surprise here. And I don’t think you need to wonder…down deep your senses are likely on target!

These type of relationships have been going on for many years. We are all wired different, but the non monogamous people have the ability enjoy a lifestyle that many just don’t understand.

[Natatude]

For years, I would have sex with my lover and never wore a condom, I’ve been with him nearly 31 years. Hubby and I have one daughter she was 6 back then when we started. He would be at our house frequently having 3somes, of course when our daughter wasn’t home during the sex, however we had cookouts and what not and always invited him. So she knew him as uncle Paul and he treated her like she was his! my whole family knew him and thought he was just my best friend, if they knew we have sex, they would call me disgusting and disown me. I never got pregnant anymore. Wasn’t on any type of birth control. I am now post menopausal, our daughter is 37 now and married and has 2 kids 12 and 10 and they also know and love uncle Paul. And he spoils them. It was and still is a huge risk.

Natatude, IMO, this is a wonderful story. Thank you for sharing.

With respect to your comment about “disgusting and being disowned”. We had a somewhat similar relationship with Susan’s first love. He was also a very good friend of mine and the three of us hung out, did sports together and also traveled together. Susan and he continued to have sex off and on (off when he was in a monogamous relationship) for more than 40 years.

In our experience, people do observe other’s relationships and can often sense when there’s something else going on in relationships. For years many of our close friends and our three boys asked us probing questions and at one point we both came out of the closet and told certain friends and our family that we are non monogamous.

Almost everyone we told responded with a comment like “we knew it!” Some even mentioned that they were envious that we had a relationship like this. Our good friends and family all know it accept us for who we are. We have a loving relationship, are respected in our community and in the business world and to the extent we know we have never lost a friendship because of our lifestyle. If we have, we don’t care. We are who we are, we love each other and love our family and friends.

IMO, you should feel no shame whatsoever having a relationship where you shared love with someone else, in an honest and open non cheating relationship.

I don’t really feel any shame, if someone figures it out, then so be it. I’m so lucky to have 2 wonderfully almost perfect men, that bend over backwards for me anywhere anytime. We live in a rural country area, there have been a couple people we have know over the years that have had risqué lives, and the folks around just talk about how awful it is and shame on them and blah blah blah! There are mostly elderly folks around here. So we just keep to ourselves and what goes on behind our closed doors is our business and no
One else’s!