r/CruelCheatingStories

So there we were,sitting around the table half naked with our wives was fucking amazing. When they came back to the table Lisa sat beside me and Arron beside my wife. "So how far are we going and if there are rules what are they" my wife asked. "Me and Arron have no problem and no rules." Lisa replied. "Were comfortable around you guys" Arron said. "Well lets go out to the patio" my wife says as she grabs Arron by the hand. Lisa looked at me and grabbed my hand sitting on the opposite couch. Lisa asked me if i would give her a back rub and i said i sure would as long as you don't mind me getting out of these boxers.I was hard and pre cumming when i pulled them down. "Ill take that as she leaned over and sucked me dry. I massaged her back and she asked me to do it from the front so she could throatfuck me. I rushed over to do what she asked and there was the wife getting pounded by Arrons huge cock. We went over and fucked each other for hours.

When my wife asked me if we could go away for the weekend with our best friends i was in. We have been friends since highschool and we are in our 50's now.

Lisa and Arron were our best friends and we were very close. Lisa was 42, with huge tits and very flirty. Arron was 45 with a huge dick and loved to party. We never had sex with each other but have seen each other nude and we

fucked our partners on the same bed. Never touched either.

We decided to go to the cottage. My wife and i went the night before to clean and get things ready.

We were sitting around that night having a drink and sitting by the fire."You be ok if i wear what i usually do when our friends are here" the wife asks. "For sure but they may feel weird" i replied. Well to get an idea tonight she wore a bra and panties that looked awesome. She was on her phone with Lisa and asked her also. Lisa hesitated answering and then asked" Can i wear what i want too". Jen replies back" Absolutely". I could feel myself getting hard,and Jen started rubbing her pussy through her panties. I sent Arron a pic of Jen playing with her pussy and asked "Buddy. We are having fun tomorrow. Arron messages back "Hell ya".

Lisa and Arron arrived around noon the next day and when they arrived we helped them unpack. Arron looked at Jen and said"You look great jen". She was wearing a bra and thong . Just then Lisa says to me" You like this". She took off her sundress wearing a bra and thong also. If you want more of this sex filled weekend upvote.

A couple of years ago I was hooking up with this married woman from a consulting company that did some contract work for my business mostly at hotels and a couple times in the back seats of our cars. She was wild and open to try anything. We tried novel positions, throat fucking, deep throating until she would gag and puke, breath play, hanging her head over the bed and face fucking, anal plugs, anal, all while being hog tied, bound, you name it we tried it.
This one day after work we met in a plaza at the back of a parking lot and she got into the back seat of my car. She was nervous and said she was certain her husband had figured out that something was going on, she felt like he was on to her and tracking her whereabouts, and this was the last time we could meet.
Not going to lie hearing that turned me on even more and I pounded her hard until she came. I asked if I could come inside and she said no I’ll finish you with off quickly by going down on you.
she got dressed and i pulled my pants half way up and she positioned herself over my lap.
She started going to town on my dick aggressively bobbing up and down, slurping and slopping.
Now my windows are tinted, but if the light is coming in a certain direction you can still see inside.
As I was getting close I see this car rolling through the lot slowly and heading in our direction.
As the car gets closer , I am getting closer to cumming and I look through window and this guy who looks distraught is staring right at me. I put my hand on the back of her head to keep her out of sight and she moans and goes deep. I can feel my dick hitting her throat. the moment i look back out my window I make direct eye contact with this dude and blow my load in her mouth and down her throat.
I tell her to stay down as the car slowly rolls past my car.
She swallows everything and asks whats going on. I point at this car slowly rolling throw the lot and she looks out the window. She was like oh shit thats my husband’s car. The car eventually parks next to her car on the other side of the lot. She starts freaking out and I tell her to relax and I will driver her around the other side of the plaza and drop her off out of sight.
We drove around and she went into the grocery store to play it off as a grocery run.
The last communication I got from her was a 👍 later that night.

My ex-wife and I have been divorced for over 20 years - it was acrimonious at first, but over the years we worked into a good coparenting arrangement and have a convivial, stress-free relationship. She married her current husband a few years after our divorce-he’s a little older and has developed some chronic health problems.

Last year we were at a destination wedding, and with no prior escalation we ended up sneaking away and having a quick fuck during the reception. We hooked up a few times after that, and I suggested that we do all the crazy, kinky things that she wishes she could do but would never bring up to her husband. She jumped at the idea and we’ve had several incredible adventures since then.

I’ve been considering posting here for a while now. This is my first of 5 or 6 stories that I want to share about my current relationship. All very real, and all with varying degrees of cheating. I have mixed feelings about each story, but mostly they’ve become a part of our sex life.

So here it goes…

It was May of 2015. My wife (then girlfriend) and I had started dating within the past year. I had just turned 19 a couple months earlier. She is 4 years older than I am, so at the time she would have been 23.

We were in the infatuation stage. We weren’t super serious, but we both liked each other and we were definitely officially dating by this time.

Anyway, she decided to go to a day-long music festival with a friend of hers that would take place on a Saturday. I don’t really remember thinking much of her going at the time. I don’t even remember her telling me. I wasn’t really that concerned, though, which is unusual for me in hindsight. I chalk it up to the newness of relationship or me being busy with friends at the time - but looking back on it, maybe I should’ve been more inquisitive.

They drove up Friday night, stayed overnight in a hotel nearby, then spent all day going to shows on Saturday.

Saturday, after the shows, when the two were heading out for a beer run, her friend bumped into another vehicle. I don’t know if it was my wife’s luck or mine, but inside said vehicle was 4 guys that had been at the festival.

There was no apparent vehicle damage, but the 4 guys, my wife, and her friend all got to talking, and… well… the guys ended up revealing that they needed a place to stay for the night.

My then-girlfriend had a hotel room in her name, and invited the guys back to have some beers. This is where the story gets a little fuzzy, and I think this is where it undeniably crosses over into cheating territory, regardless of what exactly ended up happening next…

Which brings me to this part of this story:

She maintains to this day that there was no fucking — no penis-in-vagina sex whatsoever. According to her, two or three of the guys slept in bed with her and her friend. She admits that she was very drunk, and that she has trouble remembering all of the details. After all, this was 11 years ago at this point. She did say that she was in her panties and a t-shirt by the end of the night, and that she ended up grinding on one of the guys enough to get herself wet.

I genuinely don’t see how she would’ve made it through the night without getting fucked. With that said, I continue giving her the opportunity to tell me, and she no longer has any reason to lie.

With all of that said, that’s how we started off our relationship. I didn’t know about it until about 3-4 years ago. When it came out that I got off on her being a slut, this story surfaced. I couldn’t believe that she slept with two other guys. Grinding on a complete stranger (possibly two) was never something I pictured her doing. Now I think about it almost everyday.