Your most taboo/risky sex?

[wantingfun]

Way back, there was a long-running topic discussing members' most taboo or risky sex. It was probably auto-pruned after a period of inactivity (at least, I cannot find it anymore). Let's hear your stories! But please, keep them legal and appropriate for this board (e.g. no posts about underage partners, etc.).

For me, it was when I met a married woman at a hotel for an afternoon romp. We had seen each other several times previously, so we were comfortable. But that day, she seemed nervous and rushed. We did the deed with intensity, but she said she had to leave to get back home. I asked her what was up. She said it was her 25th wedding anniversary! She wanted to be super nasty, so she fucked me and then went back to her husband. She did not have sex with him that day or for weeks afterward. She said it made her feel very powerful.

[Tank Turner]

Hi wantingfun,

Taboo sex and risky sex are two completely different concepts.

Taboo sex is subjective. What one considers taboo another might consider it normal. For instance, some people consider anal sex to be taboo sex. My wife believes anal sex is normal sex because it's so common.

Neither my wife nor I will consider degrading sex. Neither one of us would consider urine or feces as normal or even taboo. We consider urine and feces as dehumanizing sex. I'm sure a small percentage of people will consider both within their normal repertoire of sexual practices.

Risky sex is usually exciting sex. The risk of getting caught during public sex is exciting.

The married woman you banged is not unusual. A substantial percentage of women will seek sexual satisfaction beyond their marriages. I have friends whose wives have cheated on them. My wife knows women who are engaged in affairs. My guess is the dominant reason women cheat is feeling neglected and unappreciated by their husbands.

Years ago, while my wife and I were watching a show on infidelity, she told me that a woman could have sex with many men before her husband comes home from work, and he'd never know it.

[zorro]

Tank, perhaps one of the most common reasons for wives cheating is simply a desire for variety and novelty. It need not be that the husband is inadequate -- it's just that different is good for erotic desire.
True for many men, too.

[sw6]

The definition of what the OP has requested is besides the point
He is being voyeuristic on what others think - big deal
My most recent experience with this was my GF (sorry not a HWing story) telling me in bed she wanted me to do anything everything I wanted to her, and tell her what that was so she could do it.
I whiffed, thinking she wanted a story and went to Gang Bang - she said she knew that but wanted to do it right then and there
Unfortunately in the moment I couldn't come up with something tho I believed her and she can be quite the nasty skank
Blew my chance
I guess you have to be both in the right frame of mind at the time

[aztd]

Risky Sex
Getting a BJ from a cops wife under a tree next to the station about 15 yards for a busy street

[Restarting]

Sex from behind with my wife in the neighbor's pool, with our kids swimming on the other end was risky.
Sex against the window on the 37th floor of the Fairmont Hotel overlooking IH35 is probably more taboo.

[leggysman]

Sex against the window on the 37th floor ... is probably more taboo.

Maybe risky too, depending on the thickness of the glass. Great way to "check out" with flair, though!

[slenderfish]

Not a Hotwife story, but I was pretty seriously dating a woman who just oozed sexuality; we could go nowhere without guys hitting on her or otherwise approaching her (also women!).

She basically said she was down for any kind of sexual experience except 1) only the two of us and 2) no pain. She was provocative. My guy friends were always asking us to meet up with them, just so they could get an eyeful or two.

Her profession is a clinical therapist, specializing in anxiety disorders. Not sure if that plays into it, but she did have a troubled upbringing. I have concluded she got her Ph.D for the purpose of understanding and working through her issues. Probably a good play, that.

I ended up breaking up with her for several reasons but one prominent reason was I realized over time was her penchant for risky/public sex. One time, we had sex in an upscale bar/lounge, right in front of the deejay booth. She was wearing a fairly short skirt, and had excused herself to the ladies' room. Upon her return, she waved and the deejay and then quietly slipped her panties into my hand with a smile, and as she sat on my lap. She was leaning over to pick up her martini from the low table in front of us, from time to time, and in between had unzipped my pants and stroked my cock until hard, and then on one forward lean for the martini she slipped it in. Again, playing it cool, she sat unmoving until it was time to return her glass to the table and that was one stroke. It would be a stroke every minute or so, and she also turned a bit from side to side to look out the window (we were on the penthouse floor) or the crowd. She requested the bill from our server and used that as a cover for additional movement.

It was hot and I was hooked! Until some of the shenanigans in public made me realize it was only a matter of time until we got in trouble with law enforcement, etc.

Also, I'd met and started dating SW at that time, and at some point it was time to become exclusive, etc.

[Tank Turner]

Tank, perhaps one of the most common reasons for wives cheating is simply a desire for variety and novelty. It need not be that the husband is inadequate -- it's just that different is good for erotic desire.
True for many men, too.

Hi zorro,

You're probably right. Magazine articles and TV programs are far from factual.

My wife is the most sexually enlightened woman I have ever been with. She can be monogamous when we can't evade our nosy and inquisitive adolescent kids. She loves excitement of stranger sex. She wants a black dude experience. Within a narrowly defined category of men, she enjoys variety. Her preference is masculine men who are respectfully sexually aggressive, the complement to her sexually submissiveness.

[wordlover2000]

Good points about "taboo" and "risky" being separate concepts.

Risky: My wife and I regularly swapped with another couple who lived about half an hour from us. One time when we were visiting them they pulled out the sleeper sofa in the living room and we all climbed on. They lived in a typical suburb, a neighborhood of houses. It was night, and they deliberately left the curtains wide open and the lights blazing while we all blissfully fucked. Their front lawn had a severe upslope, and it's 50-50 whether anyone walking or driving past was able to see us. BUT...the houses across the street without a doubt had a clear view. These people were hardcore exhibitionists (obviously) and from comments it sounds as if their lifestyle wasn't exactly a secret from the neighbors. Evidently the wife had had her share of the men from the neighborhood visit their bedroom.

Taboo: A blowjob from my sister-in-law that stayed our secret for years (per her wishes). She lived for sucking and was a true oral artist. She went slowly and thoroughly and drove me quite insane until I exploded down her throat. It was deliciously naughty and wonderful.

[kellycuckoldsmark]

Ours would fall in the risky category I think. Definitely the most risky - by accident - we have ever done.

When Kelly and I first went beyond our marriage it was usually swapping with couples. A little girl on girl and then often same room swap. It was watching Kelly that made me realize my cuckold tendencies. Anyway, 20 years ago we were using AFF. We didn't show faces but everything else and honest descriptions, etc. We met a few couples and all was good. Then a more mature couple contacted us. I liked women older than - at the time I ws early 30's and Kelly early 20's and this couple we were in their early 50's so more Kelly's parents age. We had met with a 55yo guy and watching Kelly with an older guy was a real turn on for me and she liked his 'experience'

So we emailed with this couple and agreed to meet. Yes, this all sounds very naive but we were 20+ years ago and also there was no FaceTime or WhatsApp back then. So we were in this sports bar waiting for them to turn up when Kelly says, 'Oh no, Emily's mom and dad just walked in'. Emily was her best friend since Sunday School and it would be awkward to have our mature couple turn up and have them in the bar. But, knowing this audience you have guessed what had happened. As experienced swingers they had figured out who we were........

So we were now having drinks with not only her best friends parents but also the couple who were really close friends with Kelly's parents. They had obviously planned this all out so weren't as freaked as we were. The mom was an older version of her very hot daughter so I was in but I could see Kelly wondering what this all meant and we talked about relationships, if this was going to be awkward, etc. and we asked for some time alone.

Turns out Kelly was actually really turned on by the idea but scared they would tell her parents. I assured that telling her parents would out them as well so very unlikely. In the end the horniness overcame any sensible concerns and we agreed to go back to their place. Kelly wasn't ready to make out with the mother but after a glass of wine we separated. Kelly really wanted to have her best friend's dad in her best friends old bedroom. I went with the mom to their marital bedroom. After round one, Kelly and the husband joined us in the marital bed and Kelly kissed and made out a little with the mom.

We saw them several times over the course of the next 12-18 months both intimately and at family/friend circle events which included Emily's wedding.

Certainly not taboo although did make us wonder if Kelly's parents were swingers but for us certainly risky in those early days of the lifetyle.

[zorro]

Risky: Several years ago while in Anchorage in AK, we stayed in a nice B&B overlooking Cook's Inlet. The window to our room faced the window of a lawyer's office in the building next door. We felt frisky and began making out naked in bed with our curtains open. We looked up to see an attractive young (perhaps 30s) woman with prominent boobs in a tight but thick sweater looking at us, all the while holding a coffee cup in her hands and sipping from it. We decided to be naughty and went for it, fucking on the bed with her looking down at our socially inappropriate ardent behavior. She continued to intently watch us for perhaps half an hour (our ardor was enduring), all the while sipping what must have become cold coffee.

We wondered fleetingly if as part of a law office she would call the cops on us -- but she didn't, thank God. Being put in the slammer for indecent exposure would not have greatly embellished our vacation time. Probably the fantasy that she would want to come downstairs to join us overcame social anxiety, but she was just going to be our voyeur.

[Shantideva]

Ours would fall in the risky category I think. Definitely the most risky - by accident - we have ever done.

When Kelly and I first went beyond our marriage it was usually swapping with couples. A little girl on girl and then often same room swap. It was watching Kelly that made me realize my cuckold tendencies. Anyway, 20 years ago we were using AFF. We didn't show faces but everything else and honest descriptions, etc. We met a few couples and all was good. Then a more mature couple contacted us. I liked women older than - at the time I ws early 30's and Kelly early 20's and this couple we were in their early 50's so more Kelly's parents age. We had met with a 55yo guy and watching Kelly with an older guy was a real turn on for me and she liked his 'experience'

So we emailed with this couple and agreed to meet. Yes, this all sounds very naive but we were 20+ years ago and also there was no FaceTime or WhatsApp back then. So we were in this sports bar waiting for them to turn up when Kelly says, 'Oh no, Emily's mom and dad just walked in'. Emily was her best friend since Sunday School and it would be awkward to have our mature couple turn up and have them in the bar. But, knowing this audience you have guessed what had happened. As experienced swingers they had figured out who we were........

So we were now having drinks with not only her best friends parents but also the couple who were really close friends with Kelly's parents. They had obviously planned this all out so weren't as freaked as we were. The mom was an older version of her very hot daughter so I was in but I could see Kelly wondering what this all meant and we talked about relationships, if this was going to be awkward, etc. and we asked for some time alone.

Turns out Kelly was actually really turned on by the idea but scared they would tell her parents. I assured that telling her parents would out them as well so very unlikely. In the end the horniness overcame any sensible concerns and we agreed to go back to their place. Kelly wasn't ready to make out with the mother but after a glass of wine we separated. Kelly really wanted to have her best friend's dad in her best friends old bedroom. I went with the mom to their marital bedroom. After round one, Kelly and the husband joined us in the marital bed and Kelly kissed and made out a little with the mom.

We saw them several times over the course of the next 12-18 months both intimately and at family/friend circle events which included Emily's wedding.

Certainly not taboo although did make us wonder if Kelly's parents were swingers but for us certainly risky in those early days of the lifetyle.

This story is HOT. Wow.

[Greg_N_Shelley]

Aside from other guys emptying their balls inside Shelley, I think most of the riskier things I did were before we were married…

Sex with a girlfriend on the hood of my car parked in the driveway at 1:00am. Anyone could have witnessed that.

Sex with a married woman (not a hotwife) in her house during the daytime when there was a possibility of her husband coming home. It’s not exactly something I’m proud of today, but I flirted with that risk more than a few times.

Getting it on with a woman I just met hours earlier under a blanket while on a USAF KC10 flight from Frankfurt to McGuire Air Force Base. It still blows my mind no one else on the plane knew what was going on. Or at least didn’t give a shit.

Dating the base Command Sergeant Major’s daughter and eventually discovering she was not only his daughter, but 17 years old. Pop smoke and run fast!!!

[MarknSusan]

My wife and I have had several risky encounters over the years, but these two below were near the top of our list.

Most risky for me was fucking a friend with benefits in my bedroom when her new boyfriend was sitting out back having a conversation with my wife.

Most risky for my wife at a neighbors party, when she went upstairs and had sex with a guy while his wife was downstairs.

[hotfreaks]

We were contacted on a swinger site we used to be on by a single male. A lil back and forth emails, and he asked if we would be willing to meet him that night. My wife was feeling horny, and found him attractive. We told him we would meet him. He got a room at a motel, and off we went. Met him at the room, exchanged a few pleasantries, and withing about 5 minutes my wife was on her knees sucking his cock. He was very large and thick. My wife had worn a denim skirt, no panties and a tank top. After sucking his cock for a few minutes, he pulled her up, stripped her naked and placed her on the bed to eat her pussy. She came hard and demanded he fucked her. He put on a condom ( which she would have proffered he didn't, however we didn't know him from a hole in a wall and although we are kinky....we aren't reckless) He ended up fucking my wife really good in numerous positions all while I just watched. He finished missionary...removing the condom and cumming all over her tits and stomach.

All said and done...it lasted about an hour. We didn't even know his name. But my wife was thoroughly pleased. On the way home my wife said it was thrilling that we didn't know his name...nor did he know ours, and she felt like a call girl and I, her pimp...and it turned her on immensely. We never saw or heard from him again.

[Tank Turner]

My wife's riskiest sex was sneaking former boyfriends in her bedroom and fucking them when her parents were home, She looks back at that and thinks it was more stupid than risky. Her sister did the same thing with her boyfriends.

[BrunetteLover]

Her walking around a bachelor party (10+ guys) stark naked except for 4 inch hooker shoes.

Turning guys on with crotch-rubbing, tit-groping dance.

Me peering into a bedroom and seeing her leaned over a bed with a cock sliding in and out.

[DavaoMike]

I will always remember a time in college when a girlfriend and I were studying at the campus library. We went into one of those study cubicles, with a little window on the door, and fucked on the floor. I was a bit worried that the librarian would peek into the cubicle and see what we were doing. Fortunately, no one caught us, so we finished then went back to studying. It was hard to concentrate knowing that my girlfriend was sitting there studying with my cum inside her.

[best_friend]

what is risky or taboo is strongly conceted to the society you live in.

for me, as a bull (i don't like that name, but i don't have a better word), it was the incredible pleasure of having sex with pregnant hotwives over the past. it is this schizophrenic, being a wanton slut while also becoming a mother. i liked that. it's probably the hormones or what else, these women were just incredible and the sex with these beautiful bodies was indescribable.

i guess, it is taboo for a pregnant wife to have sex with another man. but that is the fun, isn`t it?

[hotfreaks]

My wife and I have been in this lifestyle for over 20 years....started a few months after we started dating. Years back, my wife had a fetish of seeking out her step sisters ex's and fucking them. Not while they were dating her step sisters, but after. It happened with a few guys early on in the lifestyle and we both found it very taboo and hot.

[Dream Weaver]

what is risky or taboo is strongly conceted to the society you live in.

for me, as a bull (i don't like that name, but i don't have a better word), it was the incredible pleasure of having sex with pregnant hotwives over the past. it is this schizophrenic, being a wanton slut while also becoming a mother. i liked that. it's probably the hormones or what else, these women were just incredible and the sex with these beautiful bodies was indescribable.

i guess, it is taboo for a pregnant wife to have sex with another man. but that is the fun, isn`t it?

I also hate that name. It's strangely demeaning to all involved. Beau would have been a much better word. Even something like knight.

[aglee]

Most taboo was with a relative.

Most risky--a few might qualify. One turned out very bad.

[MarknSusan]

Most taboo was with a relative.

Most risky--a few might qualify. One turned out very bad.

Well do not just leave us hanging..tell us about that vey bad experience!

[isinlarsa]

what is risky or taboo is strongly conceted to the society you live in.

for me, as a bull (i don't like that name, but i don't have a better word), it was the incredible pleasure of having sex with pregnant hotwives over the past. it is this schizophrenic, being a wanton slut while also becoming a mother. i liked that. it's probably the hormones or what else, these women were just incredible and the sex with these beautiful bodies was indescribable.

i guess, it is taboo for a pregnant wife to have sex with another man. but that is the fun, isn`t it?

I also hate that name. It's strangely demeaning to all involved. Beau would have been a much better word. Even something like knight.

I agree with finding "bull" a very unsatisfactory name. Let's all work on coming up with a replacement word. Is there a word somewhere between beau and stud?