What's the hottest thing you should regret but don't?

[SAILOR954]

Good for you!

 

[BackwoodsMama]

Just before the pandemic hit, on New Years Eve to be exact, my mother inquired about coming to my New Years Eve party. I told her that the people invited were all involved in our swingers lifestyle group, four to five couples. She knew that and had previously not been too excited about my life choices, but she now wanted to see what it was all about. I was very apprehensive but I agreed she could come.
Well, I'll be damned if she wasn't the hit of the party!! She came dressed in a one piece and rather sheer body suit and heels, somewhat a little sexier than I had ever seen her dressed before.
I pretended not to keep an eye on her for the most part but twice I saw her slip off to the spare bedroom with other couples and spending quite a long time with each one.
While I was swinging with some of the others in the game/play room I couldn't help but wonder what she was doing and it actually excited me even more.
So, in a way I kind of regretted introducing here to my lifestyle, but afterwards when I realized she was wanting to try a life quite different from the past it seemed okay. Also dad has been in poor health and she deserved a break away from all of that. At 68, I think she did.

Wow!! What an interesting experience. Thanks for sharing.

 

[Ssbbw4u1974]

I should regret that I've sexually, in some way or another, been with 3 brothers from the same family...

 

[jakie69]

Having a very hot and passionate affair with my sister in law. Knowing it was wrong but unable to stop. We really were bad for each other as neither of us had limits or the will power to say no to each other, our fetishes and kinks or even other people.

 

[justforfun8288]

A good friend from college and I were each other’s date for a wedding. His wife was out of town on a girls trip. My bf (now husband) was working the overnight shift for inventory and couldn’t get it off. We always flirted hard, but took it too far that night and wound up fucking. We felt really guilty afterwards…but not enough to not fuck again the next morning totally sober. Lesson we learned - we wouldn’t be a good couple, but we play very well together. Every now and then we have a little fun. We’re both married and shouldn’t, but it’s so much fun.

 

[HoldYouDown]

Years ago I worked as a college advisor. One female senior had a crush on me but she had a boyfriend. They both were students in my department and I advised both. After they graduated she made herself more than available and I fucked her brains out. Continued banging her for months even though I would see both her and her boyfriend frequently at work, often together. At some point I wished I could undo it but the sex was wild at least. Not sure he ever found out for sure.

 

[canopy]

I was fucking this guy in college. I was his first which I found out much later. We didn't date but we fucked on the regular. Soon he met someone and I met my now husband and our fucking stopped for a while until their relationship became long distance. Once that happened we became regular again even after his gf moved back and even after they got married. Eventually I became good friends with his wife. One day she opened up to me that she suspected he was cheating. After that any time she thought he was out with some woman or come home after fucking, she would call me and tell me about it. Sometimes she was wrong but other times I had his cum still leaking from inside me when I was on phone with her. She never found out for sure but it kept bothering her to the point they started arguing

Eventually I suggested they should move that way she can get peace of mind. They did and now they are still together and happy. I'm still good friends with his wife and see them when I travel, which is about a week or so every month

Now here's the thing. When I found out that I was his first something made me think he was mine. Every time his wife would say stuff about this "other woman" I'd be sitting there thinking "bitch I was there first. I was on your husband's cock before you. You're having him because I'm letting you". Every time he'd come to me I get a feeling he's coming home. I'd get turned on by the thought. We are not so regular as we used to be but guess what, I'll always be his first

 

[nightowl75]

My first lover was a hot married coworker. I was 21 and she was 23 when she came onto me. It took me by surprise, but I resisted out of guilt. About a year later, she came over to my place and we had sex. I felt bad at first, but it continued for months. The sex was too good, and she insisted on bareback. I only came in her a few times, even though she said she was on the pill. You never forget your first.

 

[Stan_the_skin]

Fucking my best friends dad.

Lucky dad

 

[michael00kk]

I had been lusting after a guy for a whole summer. One day he invited me to his family’s cottage for a party. We went upstairs and finally fucked. Part way through he had me bent over the desk and I heard him take the condom off. Next thing I knew he was nudging his dick into my ass. I should have said no, because we didn’t have more lube and it hurt a bit and he took the condom off, but I was also super turned on and wanted him to like me so I let him do what he wanted. He ended up cumming in my ass.

Love it

 

[Whanmore]

I should regret that I've sexually, in some way or another, been with 3 brothers from the same family...

Thats just the Triple Crown.

For me
Started with just smoke sesh with my (f) Friend in college and this Guy she knew

(he actually knew her Dad. We all bought weed from her Dad but that's its own story)

Guy brought one of his little Floozys and we were supposed to smoke. Friend ended up getting a lttle too loose with Guy. (found out later he was paying her) But while Guy was distracted with Friend bouncing on his cock...

I slid into Floozy raw and came in her. Pissed all three of them off and they kicked me out while they finished their evening together. Ahh well *shrug*

 

[Jaws82]

Fucking my best friends dad.

did you tell her?

 

[WantonOneWanted]

that woman from the hotel at that when we got back to room begged me to fuck her, and in a way I did, I rolled her over and fucked her ass

 

[live4thebj]

Getting a blowjob while her son was in the room.

 

[SarahHunt]

I had a sex with my neighbours 19 year old multiple times

 

[JimDi23]

I had a sex with my neighbours 19 year old multiple times

Such good neighbors

 

[mollylonglegs2020]

I had a sex with my neighbours 19 year old multiple times

I bet he thought he was the cat that got the cream!

 

[BiWifeMyrtleBeach]

I would say the hottest thing I should regret but don't are two specific occasions of my husband and I having threesomes with married women without their husbands knowledge or consent. I also had encounters with them alone with no men present.

 

[Christy2Cum]

It's hard for me to pick just one, but when my ex and I were still married we swapped with his brother and his brother's wife.
His brother always admitted he had a thing for me because I was a "tall, busty blonde" and his wife had smaller breasts.
I had sex with his brother more than he knew and since we split, I still have sex with my ex-BIL and my ex-SIL, sometimes together sometimes separately.
A couple months back I thought he knocked me up, I should regret it, but the brother I didn't marry is amazing in bed, and the living room, and the kitchen and the garage...

 

[WendyTrilby]

Summer before going off to college, my boyfriend Marty and I spent the night together at his friend Brendan's house. Brendan's family was out of town, so we were in his sister's bedroom. Brendan and his GF were in his parents' room. My BF had to leave super early as his family came to pick him up for a road trip to Maine. When they left, I got in the shower. Brendan came into the bathroom to pee. I was horny and opened the shower curtain so he could watch me lather up. When I started to clean my kitty, he got into the shower and did me violently from behind. I came hard. We dried off, no words. Brendan returned to the bed with his sleeping GF, and I went home.

I don't like cheating, but Goddamn, that was an amazing fuck. Fast, furious, and very wet. I don't regret it and often replay it in my mind. Brendan and I never spoke of it and never tried it again.

 

[BongoGal]

Summer before going off to college, my boyfriend Marty and I spent the night together at his friend Brendan's house. Brendan's family was out of town, so we were in his sister's bedroom. Brendan and his GF were in his parents' room. My BF had to leave super early as his family came to pick him up for a road trip to Maine. When they left, I got in the shower. Brendan came into the bathroom to pee. I was horny and opened the shower curtain so he could watch me lather up. When I started to clean my kitty, he got into the shower and did me violently from behind. I came hard. We dried off, no words. Brendan returned to the bed with his sleeping GF, and I went home.

I don't like cheating, but Goddamn, that was an amazing fuck. Fast, furious, and very wet. I don't regret it and often replay it in my mind. Brendan and I never spoke of it and new tried it again.

The hottest part about this for me is the 'no words'.

 

[Cloebishaved]

playing drunk truth or dare with cousins after a family wedding and making some poor choices lol

 

[Dcharger]

Just before the pandemic hit, on New Years Eve to be exact, my mother inquired about coming to my New Years Eve party. I told her that the people invited were all involved in our swingers lifestyle group, four to five couples. She knew that and had previously not been too excited about my life choices, but she now wanted to see what it was all about. I was very apprehensive but I agreed she could come.
Well, I'll be damned if she wasn't the hit of the party!! She came dressed in a one piece and rather sheer body suit and heels, somewhat a little sexier than I had ever seen her dressed before.
I pretended not to keep an eye on her for the most part but twice I saw her slip off to the spare bedroom with other couples and spending quite a long time with each one.
While I was swinging with some of the others in the game/play room I couldn't help but wonder what she was doing and it actually excited me even more.
So, in a way I kind of regretted introducing here to my lifestyle, but afterwards when I realized she was wanting to try a life quite different from the past it seemed okay. Also dad has been in poor health and she deserved a break away from all of that. At 68, I think she did.

That's freaken awesome. I got the exciting chills reading this little story. Too bad there isn't pictures to go w/ seeing mom and daughter having a good NYE party.

 

[AchtungNight]

Over twenty five years of off and on polyamory with a former college girlfriend. She’s into a lot of kinks I’m not and my family wouldn’t accept her as my wife, so we’re not married. But we do still enjoy seeing each other on occasion. Should I regret knowing her and being part of her swinging lifestyle? Some might say so. But I don’t.

 

[Katch123]

I've posted a few times in various threads, how I'd like to give my sister the fucking of her lifetime for all the times she teased me with her body growing up.
I've probably wasted half a gallon of cum masturbating to that fantasy over the years. That's a lot of cum that could have been deposited in other women, so just for that fact alone I should regret it but I dont.