Your most taboo/risky sex?

[LongTermHubby]

My wife and I had sex in her hospital bed where she was recovering after minor surgery.

[eb4cplslooking]

In a park area across the street from the US Capitol at night while a security guard walked by less than 50 feet away. We just laid low until he moved on.

[mrs_hotwifecplsa]

Were you already a hotwife when this happened?

Yes.

[isinlarsa]

Were you already a hotwife when this happened?

Yes.

I wonder if he had any idea you were in the lifestyle and might be receptive.

My girlfriend had a situation that was a little bit like yours, but it occurred at a sex club. She was given the guy she was with a blow job (she was my girlfriend, but she often went to sex parties with other men). He was laying on the ground, and she was on her knees between his legs sucking his cock with her ass sticking up. Some guy she didn't know came up behind her, and pushed his cock into her. She was lubricated enough from the blow job that he slide right in, and he grabbed her hips and started fucking her. As he fucked her, he told the guy she was blowing, "She's really tight." He fucked her until he came inside her; and she got the load from the other guy in her mouth about the same time.

After they disconnected from each other, the guy who fucked her introduced himself to her. He also introduced his wife to the blow job guy. Then he fucked my girlfriend again, while the blow job guy fucked his wife.

[mrs_hotwifecplsa]

Were you already a hotwife when this happened?

Yes.

I wonder if he had any idea you were in the lifestyle and might be receptive.

My girlfriend had a situation that was a little bit like yours, but it occurred at a sex club. She was given the guy she was with a blow job (she was my girlfriend, but she often went to sex parties with other men). He was laying on the ground, and she was on her knees between his legs sucking his cock with her ass sticking up. Some guy she didn't know came up behind her, and pushed his cock into her. She was lubricated enough from the blow job that he slide right in, and he grabbed her hips and started fucking her. As he fucked her, he told the guy she was blowing, "She's really tight." He fucked her until he came inside her; and she got the load from the other guy in her mouth about the same time.

After they disconnected from each other, the guy who fucked her introduced himself to her. He also introduced his wife to the blow job guy. Then he fucked my girlfriend again, while the blow job guy fucked his wife.

That's hot!

[mrs_hotwifecplsa]

Were you already a hotwife when this happened?

Yes.

I wonder if he had any idea you were in the lifestyle and might be receptive.

I often make eye contact and flirt with men who I find attractive, which I did that night before that dance, so it's possible that is what instigated it. Also my husband has been known to arrange situations for me behind my back.

[isinlarsa]

Were you already a hotwife when this happened?

Yes.

I wonder if he had any idea you were in the lifestyle and might be receptive.

My girlfriend had a situation that was a little bit like yours, but it occurred at a sex club. She was given the guy she was with a blow job (she was my girlfriend, but she often went to sex parties with other men). He was laying on the ground, and she was on her knees between his legs sucking his cock with her ass sticking up. Some guy she didn't know came up behind her, and pushed his cock into her. She was lubricated enough from the blow job that he slide right in, and he grabbed her hips and started fucking her. As he fucked her, he told the guy she was blowing, "She's really tight." He fucked her until he came inside her; and she got the load from the other guy in her mouth about the same time.

After they disconnected from each other, the guy who fucked her introduced himself to her. He also introduced his wife to the blow job guy. Then he fucked my girlfriend again, while the blow job guy fucked his wife.

That's hot!

When she told me about it, she was particularly proud that he found her cunt tight. She was rather inexperienced when we first got together, but she had some really hot experiences, some with me, some on her own that she told me about.

[isinlarsa]

Were you already a hotwife when this happened?

Yes.

I wonder if he had any idea you were in the lifestyle and might be receptive.

I often make eye contact and flirt with men who I find attractive, which I did that night before that dance, so it's possible that is what instigated it. Also my husband has been known to arrange situations for me behind my back.

Do you think he did in this case, since he went along with what was happening to you?

[mrs_hotwifecplsa]

I often make eye contact and flirt with men who I find attractive, which I did that night before that dance, so it's possible that is what instigated it. Also my husband has been known to arrange situations for me behind my back.

Do you think he did in this case, since he went along with what was happening to you?

My dear husband is a submissive cuckold, he'd go along with it even if he didn't arrange it so long as he saw me enjoying it, which I definitely was

[mrs_hotwifecplsa]

That's hot!

When she told me about it, she was particularly proud that he found her cunt tight. She was rather inexperienced when we first got together, but she had some really hot experiences, some with me, some on her own that she told me about.

My husband says I'm loose, like fucking a mayonnaise jar.. but all my Bulls all say I'm tight!!

[Long Lurker 34]

In a park area across the street from the US Capitol at night while a security guard walked by less than 50 feet away. We just laid low until he moved on.

E4CL -

[isinlarsa]

That's hot!

When she told me about it, she was particularly proud that he found her cunt tight. She was rather inexperienced when we first got together, but she had some really hot experiences, some with me, some on her own that she told me about.

My husband says I'm loose, like fucking a mayonnaise jar.. but all my Bulls all say I'm tight!!

LOL. That's how my wife let me know that her young black studmuffin was really big. When I asked her how it was to be fucked by him, she answered: "I was really tight."

[elina]

That's hot!

When she told me about it, she was particularly proud that he found her cunt tight. She was rather inexperienced when we first got together, but she had some really hot experiences, some with me, some on her own that she told me about.

My husband says I'm loose, like fucking a mayonnaise jar.. but all my Bulls all say I'm tight!!

Have you asked your submissive loving cuck to explain why this is so?

Sincerely
elina

[atl0707]

When I was young around 7 or 8, my babysitter would suck me. It was great. She also let me fuck her, though it didn't work that well. As I got older, the most taboo experience was sleeping with a 55 yo when I was 20. The age gap was something else, but she knew what she was doing. I would fuck anything back then. These days, I don't get to do much that's taboo, but my wife certainly does.

[atl0707]

When I was young around 7 or 8, my babysitter would suck me. It was great. She also let me fuck her, though it didn't work that well. As I got older, the most taboo experience was sleeping with a 55 yo when I was 20. The age gap was something else, but she knew what she was doing. I would fuck anything back then. These days, I don't get to do much that's taboo, but my wife certainly does.

[isinlarsa]

When I was young around 7 or 8, my babysitter would suck me. It was great. She also let me fuck her, though it didn't work that well. As I got older, the most taboo experience was sleeping with a 55 yo when I was 20. The age gap was something else, but she knew what she was doing. I would fuck anything back then. These days, I don't get to do much that's taboo, but my wife certainly does.

What taboo sex does your wife do?

[mrs_hotwifecplsa]

When I was young around 7 or 8, my babysitter would suck me. It was great. She also let me fuck her, though it didn't work that well. As I got older, the most taboo experience was sleeping with a 55 yo when I was 20. The age gap was something else, but she knew what she was doing. I would fuck anything back then. These days, I don't get to do much that's taboo, but my wife certainly does.

She took a huge risk, and it's hot to hear. My husband says when a girl or woman does that to a younger kid, the kid is crazy to "tell" on her.

[superb101]

Another tabu:
I was seeing/fucking a doctor. Our sex was very D/s and he knew I was a hotwife with a cuck hubby. He asked me if I'd be interested in taking his son's virginity and teaching him to do sex right. I agreed.

How old was his son? How old were you?

I was purposefully vague. He was a couple years after puberty.

If you would, please tell us more. Did you just go to his home? Hotel? Had you met him at an earlier time? Details, please!

[Luv2SucknSwallowFEM]

Taboo is subjective... I don't consider it the same as risky.
I tend to think of taboo being "Outside of accepted society norms" ie, something that might be illegal. or potentially leading to being ostracized. I guess that would include, family, younger sex, rape, beastiality, prostitution etc. In other words - society says "You can't do that".
We all have our secrets though.
I honestly don't think I can tell most of my taboo secrets here, but will touch on one.
I have prostituted.
Initially it was a necessity for money (long time ago when I left home) but there have been a few encounters I have played out simply because of the taboo nature of it and the fantasy. Being paid for sex became an actual turn on. There is a power aspect to it and a degradation aspect that is extremely exciting. I am very turned on by objectification - being seen and used as a source of pleasure by men and women... so it fulfills a need inside me.

Risky sex is about getting caught or taking extreme chances that can have consequences in my opinion. Cheating, unprotected sex, public sex, dangerous sex etc. I admit I have pretty much done all of that LOL.
There is one that comes to mind... . Risky because it was no condoms... it was public.... obviously dangerous because it was with two strangers.... and it does stand out as one of my top three (or five ) dirtiest encounters.

I had anal sex with two guys in a dance club when they tag teamed me in a bathroom stall.

The whole encounter happened on a dare really.
Was at the club with friends, met these guys, danced with them, hung-out... and we were talking dirty, trying to show-off, brag or impress them. We were sitting at a booth and I told them "I fucking love anal sex"!!! - just to get a reaction.
This isn't something that was a habit, I was just in that headspace. Now there was a lot of alcohol involve... some coke and I was definitely on the Molly that night, so my whole head and body was just wired and floating.
At some point I was making out with one of them on the dance floor and I was rubbing his cock through his pants... he started fingering me. I was wearing the obligatory sexy black dress - body tight, no bra.... pink thong underneath. While he had his fingers up my pussy the other guy came over and they sort of sandwiched me. I was sooooo fucking horny that when the other guy started kissing me I just went with it. I was going back and forth making out with them, letting them clutch and grab at me. It went to another level of horniness for me when I had both their tongues in my mouth at the same time and they were even kissing each other.
"Holy fuck.... that's hot as balls" I said. I was totally lost in it all. Bi guys have always been a weakness. I watch a lot of gay porn.
They sort of half pulled - half guided me towards the washroom and I said "You gonna fuck me in there"... looking as coy and as dirty as I could. I flicked my tongue across his lips as I said it.
The first guy said "You wanna fuck baby...?"
I whispered in his ear "I wanna fuck..."
He then said "Fuck your ass?"
I laughed and they started in with "C'mon baby.... show us what your made of... you said you love anal... prove it... show us".
SO it was on. I was like "Ok, I'll show you guys".
My heart was racing... and my pussy was just dripping.

They pulled me into the bathroom, there was a bunch of guys in there smoking pot. When they saw me come in led by the two of them there was like a cheer that went through them all.
They took me to the last stall and started pulling off my panties. I just stepped out of them and kicked them into the corner. I had the guys tongue in my mouth and his cock in my hand... felt it drip all over my fingers... I fucking love pre-cum so I licked them and tasted it.
I was definitely in slut mode. For any of the Ladies who are reading this you know what I mean. You just reach that point of no-return and all you want is cock.
I got turned around and pushed against the wall and I felt his cock poking between my butt-cheeks.
I said "Wait... wait".... and spat in my hand, reached back to smear spit on my anus.
I had my hand up on his chest to steady him and let him know I needed to control the penetration.... once he was there and I could feel the head of his cock pressed against my hole I just said "Ok... Do it".
The other guy was standing behind us, He had closed the door so nobody could see in but there were guys hoisting themselves up to peer over the stall. He was stroking his cock.
He pressed forward... I guided it and as I pushed back he pushed forward and the resistance hung him up for about a second then his dick slid up my ass the moment he broke the seal.
I let out an almighty gasp and he practically screamed.
Hand on the wall and my other hand clutching the paper dispenser to give me some leverage.
I think he only got a dozen strokes in before he said "O fuck I'm gonna cum".
I remember the extreme disappointment when he finished so fast. I was like "WTF was that... all that bragging and he couldn't live up to the hype LOL". Yeah well the next guy made up for that.

I didn't change my position when the other guy stepped behind me with his cock. Dude #1 just fell back against the wall and watched.
#2 went in a lot smoother (of course) and just sank into me like butter. I could feel a squish around his cock and my hole as the other guys cum just oozed and bubbled. It felt so dirty.
The moment he fully penetrated me we stood there and just moaned together. My eyes rolled into the back of my head and I whimpered half crying "Yyyyeeeeessssssss.... oh fuck.... please".
My legs were shaking and he really started fucking me. I remember the rhythm we had was in sync with the pulse of the music from the club.... since it was an industrial dance club (Nine Inch Nails, Ministry etc) the beat was pretty hard and fast and I absolutely zoned into it.
I came within about the first minute, came so fucking hard I lost all ability to hold myself up. The first guy grabbed me and helped guide me over to the toilet where I was draped over it while his buddy just fucking hammered me. I think we fucked for a good 10 mins. I would look up in an orgasmic daze and see guys cheering him on.
I was a mental mess at that point. Utterly gone.
There was cum running down the inside of my thigh and I was rubbing my pussy while he pumped... I was soaked... and it just went on and on LOL.
When he was close - and I could tell... I can always feel when a guy is about to cum (unless it's so quick it's just a surprise). The way their body changes, the determination, sound of their moaning.... bearing down just a little harder.... making sounds like they are going to die haha...
So I told him as seductively and slutty as I could "Cum in in me baby... I want you to cum in me too"... and he just exploded.
I came again at the same time and we just collapsed over the back of the toilet.
Guys were banging on the walls of the stall and I remember feeling both proud of myself and a total slut.... although I don't think any of them realized this was anal, they just thought I was getting blasted from behind.
We cleaned up and sort of leaned against the stall looking at each other. Awkward laughing and repeats of "Holy fuck girl.... Damn.... you're amazing.... that was incredible". They were dumbstruck I did that. Honestly, I wasn't. I had this smug look of "Told ya... fuck you for calling me out".
Maybe it's weird thing to remember (and say here) but I strangely recall getting the paper from the dispenser, wiping myself up a few times and us laughing that it wouldn't stop dripping out.
"What the fuck guys.... you shoot a beer bottle in me or what".
I'm so fucked up.
Then we left.

I had a lot of guys buy me drinks after that though LOL. A few tried to see if I was up for more with them, but I was pretty fucked out at that point, To high as well to really do anything.
My friends looked at me wide eyed when I came back - on my own.
"Where the fuck were you". I didn't tell all of them, but did tell my bestie "I just got tag-teamed in the guys washroom".
She loved it.

... and that's how you spend your 22nd birthday.

So yeah, risky, dirty, nasty.

[mrs_hotwifecplsa]

... and that's how you spend your 22nd birthday.

So yeah, risky, dirty, nasty.

That's hot!

[sandy691196]

When I was young around 7 or 8, my babysitter would suck me. It was great. She also let me fuck her, though it didn't work that well. As I got older, the most taboo experience was sleeping with a 55 yo when I was 20. The age gap was something else, but she knew what she was doing. I would fuck anything back then. These days, I don't get to do much that's taboo, but my wife certainly does.

She took a huge risk, and it's hot to hear. My husband says when a girl or woman does that to a younger kid, the kid is crazy to "tell" on her.

When I was 7 to 9, I used to play with other kids around my age. Obviously it came down to genital play. But refinements like oral and stuff never came up. It would be weird at that stage. When I was 9, a girl my age (P), while feeling each other's naughty bits, stood up (on our terrace).. parted her vulva (can it be termed pussy at that age? Such an innocent, cute thing?) and asked me to put my innocent little cock in that gap. I had no idea about the map of a female genital then.. Didn't know clit, labia minora, vagina.. what is what. It just seemed strange to me - her desire that I put my thing in that gap!
I made a face and asked - "what for?" She pulled her drawers up and asked- "then why even fondle it? What for?" That was the end of it!

Maybe innocence is a real thing? Maybe there is a time for things? But it would have been jolly good if an older woman did me, in my 13-14 yr stage. I had a perpetual hard on (am kinda thick) and my school uniform shorts fought hard to hold the erection in. My undies couldn't cover the cock at such times. I went around the whole day like that. Once our (lady) language teacher (I was in Cl IX) stared at my crotch in a trance, the whole time it took me to walk up to the front of our classroom from the back seat.. on my way to the wash room.
Man! Have I fantasised all my adult life- what may have happened if Mrs S had called me home sometime for extra classes!

[Luv2SucknSwallowFEM]

In the Taboo vein I guess my early experiences would qualify. I'd be more inclined to discuss the sexual details privately.

I did begin exploring myself young, masturbating, touching myself and insertion.
Around that age I would take boys behind the house or somewhere alone by the park or creek and make-out with them. John and Charles were the two I did this with most often. Charles could french kiss well... John and I would lay down and he would get on top and hump.
I was extremely curious and I loved the touching and warm, tingly feelings all over, especially "down there".
I was a humper and grinder. The corner of a table, my bed, a bedpost. I would hump until I got that feeling like I was peeing and my body would shiver. Sometimes I did this so much I rubbed myself a little raw.
I got in trouble in school because I was caught making out with a boy at school. We thought nobody could see us, there was nobody around, but a Teacher in one of the portables saw us through the window in the door. It was reported to my parents. My Mom flipped out. She was very snobbish, a prude, controlling and her and I always had a difficult relationship. In my teens that would escalate to rebellious sexual activity. I consciously fucked guys with my mothers outrage in mind. I was doing it to spite her at times.

I had a large family and I was the first born girl. My Dad had 5 brothers and a sister. He was the oldest, my Aunt was 2nd to him and she had a son as a teen. She was shunned and ostracized as a result, but eventually she was brought back into the family so I got to know my older cousin.
Growing up as the oldest girl and the sole niece for about 12 yrs I was spoiled and dotted on by all my Uncles. I think this made me very comfortable around men and I was always drawn to them. Jumping up in a mans lap, holding their hand, hugging etc. I was affectionate and learned the power a female has over a man. I loved the attention.
The whole family started having 3 week summer vacations at resorts in Quebec and New York. There were more cousins now, but they were all under age 5 and me older I had a crush on my older male cousin.... yeah, things sort of played out into exploring a lot more.
We would run off somewhere private or hide in the bathroom, basement, anywhere we could and make-out. He would reach down into my pants and rub me.... he gave me my first full orgasm. I had little climaxes before when I masturbated, but nothing like this. I wanted him to do it ALL THE TIME!!! I would take his hand and push it between my legs to let him know "DO it again". I loved it.
He was also the first cock I saw fully erect. I was utterly fascinated with it. Holding it, playing with it. I loved the balls and his soft scrotum that was still smooth. He had hair around his penis but not fully. I loved the way it made me feel to touch his penis. Made me content and safe.

After that vacation I took the new things I learned and started trying to do them with other boys, but they weren't like my cousin. I went through a lot of confusing frustration.
Ultimately my incessant curiosity and needs led to me getting involved with a friends older brother. He actually popped my cherry by fingering me with his thumb. I just remember the shocking jolt of pain and some blood.
But after that everything was good and I started a phase of making out with guys and letting them finger bang me.
I had a lot of guys coming around when that information got out, LOL.
I was having fun.
I lost my virginity fully that same year. It was a much older man. I'll just leave it at that.

[BT2]

The above post from sandy691196 reminded me when I was about the same age, 7 or 8. We lived in a small village in Ontario. A bunch of us kids, both boys and girls, used to play with a kid on a farm at the edge of the village. One afternoon we were playing and we decided to play "farm". We all undressed. In our innocence (pre internet) we knew that cows were female, but the girls (our age) didn't have any parts for the "calves" to suck on. So the boys were assigned the parts of cows and the girls were the calves. We boys got on our hands and knees and the calves (girls) would suck us (our penises). Even at that tender age it sure felt good.

But alas, a couple of the little girls eventually got worried that what they were doing was wrong - not sucking on us, but being naked in front of boys. I remember being then being scared myself that one of the girls would tell her parents. So we stopped playing "farm". Nobody squealed, but we never played that game again.

Hardly a hotwife story, but it did qualify as "taboo/risky sex".

[hotfreaks]

At one point in the lifestyle, my wife got off on fucking her sisters ex- boyfriends. She needed to hear that her pussy and head was better than her sisters. The result was about 5 guys fucking her and cumming in her pussy

[sw6]

My GF is a very wild child, especially if you add whiskey

I knew she liked outdoor sex, didn't think it was necessarily about exposure or being seen/caught

One night during one of our more active episodes all over her house, she said something about going outside, it must have been midnight. I said "here, now?"

She grabbed my hand (both naked) and took me out into the driveway (just enough room to park your car, car being present) - and basically in front of the car went at it. People driving by could see us, neighbors, anybody. I still have the video I took for her and she sent me of a BJ