Your most taboo/risky sex?

[MarknSusan]

Unfortunately neither one of us finished!

Sometimes that happens

[Jdotswift]

@snakem Did you manage to continue the friendship after that evening or was that the end of it?

[snakem2000]

Yes, we continued the friendship but there were no other events. We never discussed it but now wish I did. Later after I was married I found out from my wife that he tried to sleep with her but she turned him down. But he told her I did sleep with his wife before we we married.

[bltn1966]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

[hotfreaks]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

Holy shit!! Although nerve racking while going through it, but looking back...had to be one of the hottest things ever

[Floridian]

My wife got pregnant by the other guy, so I would say....BEING CARELESS

[MarknSusan]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

OMG! That is the best story ever! LOL!

[regular3]

Such a great topic. Awesome stories.

[noreaster]

This includes both taboo and risky. My wife had an ongoing thing with a close relative of mine. At the time he didn’t know I knew it was going on. He and a couple of his kids (younger) stayed the night at our house with his kids sleeping upstairs with ours. He slept on the couch. Our bedroom was downstairs and shared a thin wall with the living room.
Very early the next morning I convinced her to go visit him before I or the kids woke up. It took some convincing but she eventually got out of bed, went out the door and down the hall to the living room. After a minute I heard him moan then heard the couch creak as he moved and the sound of their voices for just a moment. Then all was quiet. I figured she was kneeling next to the couch sucking his cock.
It was only a few minutes when I heard footsteps upstairs, the bedroom door open and several feet coming down the stairs to the hallway. It happened so fast there was nothing I could do but hope they heard too. Luckily they did and she was able to sit in the recliner and he was able to cover up before the kids came into the room.
She came back into the bedroom a few minutes later and told me she was indeed sucking him when they heard the noise from upstairs and were able to recover before the kids came through. I could say the kids never got up that early but they did that day. It’s not a chance we took again.

[MarknSusan]

A little background before I tell about this experience. Susan’s first love was also a good friend of mine from high school. About three years after they broke up Susan and I began dating and before we got married she told me she had a confession which was she would always love him because “he got my cherry”. I told her if she ever wanted to have sex with him after we got married it was ok as long as she did not lie or cheat behind my back.

He ended up getting married about the time we did. So his new wife tolerated Susan but it was apparent that she did not like her because they were past lovers. Nonetheless we hung out together because they had two boys which were the same age as our boys.

One night they were over for dinner and his wife drank too much and passed out on the couch. So Susan, he and I went outback with another drink. Just after we sit down Susan gets up and goes inside for what seemed like 20 minutes. Just about the time he asks me where Susan went (I had no idea what she was up to) she comes walking out in a short summer dress. I later learned that she went inside, shaved her legs and pussy for him.

Within a minute or so Susan was all over him making out and when he ran his hands up her skirt he looked at me and said “she’s not wearing underwear,”. Then I got involved and he and I both played with her. Then he pulls off her dress and I am thinking the nieghbors might be watching us but if his wife wakes up and finds us we are in serious trouble!

When Susan began taking his pants off I stopped them and suggested we go next door to a nieghbor that was a snowbird and wasn’t living there at the time.

We ended up getting naked and went skinny dipping in the neighbors pool and they are all over each other again. We finally get out of the pool and he and I are taking turns with Susan until he begins fucking her doggy and she’s getting loud. At this point I’m worried his wife may hear us so I’m asking her to be quiet when all of a sudden he groans and cums inside her.

As bad as I wanted to finish in her next I was too worried so we all got dressed and made it back to our home without getting caught by his wife. However, I wonder to this day if any of our neighbors were watching us!

By the way. They got divorced and Susan continued her relationship with him for more than 30 years until he got into a new relationship and moved away.

[isinlarsa]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

How did she explain not having bought anything?

[Texas2Step]

Risky….Top floor of the Anatole hotel in Dallas, 3am, taking my wife from behind as she leaned over the rail looking down inside the atrium, immediately after a young buck had unloaded insider back in the room.

[bltn1966]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

How did she explain not having bought anything?

She came into the house with two shopping bags from when we went shopping the day before.

[bltn1966]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

Holy shit!! Although nerve racking while going through it, but looking back...had to be one of the hottest things ever

It was extremely nerve racking on so many levels. At one time her mother wanted me to give her a tour of our Airbnb. She also kept saying she can’t believe her daughter would leave the house without her cellphone. I was also angry that my wife was taking so long to return from her shopping trip. She hilariously CLAIM that she wanted to end it early but the guy wouldn’t stop. Afterwards my wife told me her BF fucked her on the bedroom floor because the bed was making too much noise. It was also extremely awkward sitting there with the in-laws knowing their daughter (my wife) was upstairs getting her brains fucked out.

[hotfreaks]

My wife and I stayed in an Airbnb that was about a 45 minutes drive from her parents home. We didn’t plan on meeting anybody while we there. An old BF, that lived in that city, saw pics of my wife on social media. After a lot of texting back and forth my wife reluctantly let the guy visit us. Needless to say after a little reminiscing and drinking my wife and her BF went into an upstairs bedroom.

I planned on giving them a few minutes of privacy before I check on them. A few minutes later her parents knocked on the door. They drove to our Airbnb to surprise their daughter. I told them that my wife went shopping. My mother in law saw my wife’s phone on the coffee table. She said she can’t believe her daughter would go somewhere without her cell phone. She said well sit her and wait for her to get back from shopping. I got extremely nervous because I know my wife is very vocal when she’s getting hammered. I could hear the bed knocking against the wall. I was afraid her parents would hear what was going on upstairs and put two and two together.

I excused myself and made a beeline to my wife in the bedroom. My wife and the guy had just started when I barged in. Thank goodness o walked in when I did. The guy had just put her legs on his shoulders and he was about to some serious pounding. I told my wife about her parents being downstairs and they’re waiting on her to get back from shopping. I expected my wife to flip out and kick the guy off of her but she didn’t. We came up with a plan for her to use the outside stairs on the wooden deck to come downstairs. Then she’ll come onto the house as if she got back from shopping.

I went back downstairs to her parents and waited for my wife to return from “shopping”. I expected my wife come thru the front door after a few minutes. Boy, was I wrong. Then I faintly heard the bed knocking on the walls again. I was turned on a mad at the same time. Here I am calmly talking to my in-laws while their daughter is taking a serious pounding upstairs. I turned on the TV, with the volume up , so they could watch a football game. Finally, an hour later my wife finally came back from “shopping”. I saw her BF car driving away from the house as she walked thru the door. My wife gave me a devilish grin. She said “that was one of the best shopping trips I ever had”. “You should’ve been there”.

Holy shit!! Although nerve racking while going through it, but looking back...had to be one of the hottest things ever

It was extremely nerve racking on so many levels. At one time her mother wanted me to give her a tour of our Airbnb. She also kept saying she can’t believe her daughter would leave the house without her cellphone. I was also angry that my wife was taking so long to return from her shopping trip. She hilariously CLAIM that she wanted to end it early but the guy wouldn’t stop. Afterwards my wife told me her BF fucked her on the bedroom floor because the bed was making too much noise. It was also extremely awkward sitting there with the in-laws knowing their daughter (my wife) was upstairs getting her brains fucked out.

Oh I could imagine!! But looking back now....gotta be a hot memory

[PANTIES]

My wife got pregnant by the other guy, so I would say....BEING CARELESS

Mine did the same thing and had his baby August 11. We tell people she got pregnant rather than using IVF.it was less expensive thus way plus we were able to decide who would be the biological father.

sissy pauline

[re556]

I ended up cheating on my ex-bf and lost my virginity with another guy on a trip. On our second date, we had one of the most risky affairs I consider to date.

After my incredible first time with him, I found myself thinking about that day again and masturbating a lot for several nights remembering that wonderful cock. I was dying to have my second time. My ex sent me several messages wanting to get back together, but I knew that nothing would change and he wouldn't give me the sex life I wanted with his small cock. He realized that he lost a desired woman like me and he wasn't going to contain my fire now.

Since I exchanged contact details with the guy who had taken my virginity on that trip, we started talking more and became very close and decided to go out for dinner. I didn't set any expectations that we would have sex this time. I was still young, I was going to start the university and I couldn't spend the night out, much less have one of my friends cover for me in case something went wrong. I was ready to date a little and that was it.

The day arrived, a beautiful wednesday (I remember the date to this day), and I had gotten all dressed up to meet him. A little background about me: Tall, thin, dark hair, blue eyes and at the time I had more thighs than breasts. I put on a black dress and waited for him to pick me up.

We went to a great restaurant and he was wonderful to be with. Since we had made our reservations early, we agreed to go see a movie at a nearby mall. The mall is one of those where the parking lot starts on the top floor of the building and goes down, and he ended up parking on the top floor, where it was open to the air. It wasn't full, since it was a reasonably quiet day.

We looked for an emergency staircase so we could go down one floor and get to an elevator and we noticed that the door was a little stuck. He forced it a little and we managed to get into the staircase, which seemed to be normal since it was all lit up. We went down one floor and the door wouldn't open at all. We thought it was strange and went down another floor and nothing. It was locked from the outside. We even heard someone trying to open the door from the outside to access the stairs, and they were also unsuccessful. We realized that the emergency staircase was probably out of order, even though it was all lit up, and that was why the penthouse door was stuck.

We went up another floor and before we got to the penthouse floor to go to another staircase, I noticed that he was looking in every corner and I noticed that he was actually looking for a camera. I noticed the malice in his intentions and I confess that I doubted if he would dare to do it right there.

He grabbed me by the arm, pulled me in and immediately started kissing me madly. It wasn't long before we were against the wall and he put his hand and smoothed my body under my dress. I was already getting wet with his huge hand smoothing me all over. He started to pull down my panties and when I saw that they were already all on the floor, I quickly lifted my left foot so I could put the panties aside with my right foot and be freer.

He started playing with my pussy right there and then started fingering me. I was so wet that his fingers got soaked. I couldn't believe I was being fingered in the emergency stairwell of a shopping mall. Luckily, the doors to the floors were locked and if someone came from the top floor we would be able to hear and get ready.

I didn't want to be left behind and I quickly opened his belt and unbuttoned his pants and took out that huge cock. Finally. I was touching that cock that took my virginity and kept me awake at night thinking about it. I started jerking him off right there while he fingered me. I didn't want to take too long and soon got on my knees and started sucking him. I started sucking the huge head of his cock and tried to put his whole cock in my mouth, which I obviously didn't manage, but I definitely got his cock all wet. But I was really dying to give it to him.

I got up and started kissing him again until he realized it was time. He led me towards the railing of the stairs and made me sit on the railing, using the wall as support for my back and he spread my legs. We were at the perfect height for him to put his cock inside me. I noticed that he hadn't even thought about putting on a condom and should probably be in the car but I didn't care, there was no way I could leave that place without losing the mood.

He finally put that dick inside me. How delicious. I spent days wanting him. He started pumping slowly and gradually accelerated, pressing his body. I was sandwiched between his body rubbing against me and the wall supporting me. With his warm body pressed against mine as he pumped. I moaned with pleasure in his ear and was careful because even if the door was locked, anyone on the other side would hear.

I was there, giving it to a guy on the emergency stairs of a shopping mall and could be caught at any moment. I had come thinking about it.

He stopped to make me stand up, with my back to him with my arms stretched out using the wall as support and he started fucking me again, pumping hard from behind while slapping my ass. That huge cock opening up my tight, beginner pussy.

I felt him start thrusting harder, his cock throbbing and he was close to cumming. I had my second orgasm with the intensity with which he was tearing me apart. I soon thought about fulfilling another wish my friends had been talking about: getting cum on my face. Before he even said he was going to cum, I told him to cum on my mouth. I was finally going to taste cum for the first time. Hearing my friends talk about it made me want to try it, and my ex wouldn't even give it to me. These were first-time desires.

He quickly pulled his dick out of my pussy and started jerking off, waiting for me to bend over to cum. I admit I was a little nervous he would cum hard and splash it all over my hair, so I opened my mouth wide and stuck my tongue out. It didn't take long for him to put the head of his dick on my tongue and I could feel his dick throbbing and in seconds I felt that jet of cum entering my mouth. His jet was so strong that it ended up leaking out of the corner of my mouth and started to run down. I finally got my first cum on my face. As soon as I felt the blasts stop, I swallowed all that warm cum and started to clean his cock with my tongue, and I went crazy listening to him moan with desire.

That was it. I had just had my second time in the emergency staircase of a shopping mall where I took cum in my mouth like a slutty. I imagine what it would be like if someone had caught us doing that there. It was a risky case.

He picked up my panties that were thrown on the floor and I quickly put them on. In the end? We had already missed the movie we wanted to watch and it was much better. I can't help but think that going into that disabled staircase was a sign that it was supposed to happen right there.