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

My wife is really game for anything when she is drinking, we went to a friend's apartment party and there was heavy drinking. We volunteered to stay and get our friend to bed and clean up. Our friend was really drunk, very beautiful with big tits. She went into her room as we were cleaning up and suddenly came running out totally naked and laughing. She almost fell so my wife puts her arm around her and she kisses my wife on the mouth, my wife kissed her back and the next thing she is rubbing her tits and sucking her nipples, our friend is woozy aand we help her into her bedroom, she pulls my wife onto the bed and feels her up, my wife strips off her clothes as do I, she is french kissing her and starts rubbing our friends clit when suddenly our friend leans over and pukes in her basket. We clean her up, my wife and i are naked, my wife is rubbing her own clit, I look at her and she starts rubbing our friends breasts and sucking on her nipples, I stupidly shake my head no, we put her under the covers, get dressed and get in the car, my wife pulls her pants down and jills off, I am hard, she passes out! I regret that I didn't let her go to town on our friend!!!
 
I was 22 at the time, and I spent a summer banging one of the girls working at the pizza place I was an assistant manager at.

She was 17 (age of consent was 16), and the first time I fucked her in the kitchen after close, I blew my load deep in her, and then we went to my house and fucked all night.

I always fucked her raw, always came inside, never cared about birth control, never asked.

Dumped her a few times to fuck the ex-GF, but she was in love with me and would always come over for more dick.

The last time I called her over, she came in, I pushed her down face first on the bed, blew my load in her, and sent her out the door back to her boyfriend.

I should have regretted treating her like that, but tbh, I did not at all.
 
hey...

My wife could never talk about sex. (she was sixteen when we met, she is 59 today...) She was never comfortable talking about sex-, even to this day. Anyway, we had just had a baby girl, her doctor was like "...ok everything is good but no sex 3 to 6 weeks, make sure everything heals up nicely." 6 MONTHS LATER---, still no sex, 8 months no sex, no talk no nothing, just fucking venom and hatred. Coming up on my daughters 1st birthday. Some guys I knew wanted me to front their garage band, because they knew I could sing and I wrote my own material. We found a place to practice and was steadily hitting it, well the owner of the garage had our one guitarist fucking her om the regular with his 11 inch cock. So we didn't have to pay rent, Unfortunately--- he wasn't supposed to be fucking any other pussy than hers, that's what got us kicked out.

I said all that to say this, the owner of the garage had a niece that would come over on the regular. She started sitting in on our practice and she started hitting me, me over a year now without sex, I held out for all of about ten minutes. After that we were in her aunts bedroom on the bed with me eating her out. Thankfully she had the presence of mind to lock the door. Because my wife came busting into the house, kicked open the front door and demanding SOMEONE TO MAKE ME APPEAR!!! She musta raged around that house for 15 minutes looking everywhere she was able to and I was steadily licking in the bedroom. Then after that girl was done spasming, I took a years worth of sexual frustration out on her until as I was flipping her over for one more 'go', she planted her foot in my chest and pushed me off the bed.
 
Well, here goes!

I was married for only about five months when this happened. My best friend, Jane invited me to a large family party at a local Legion. My husband was working an extra job that night, but gave his blessing for me to go and have a good time.

While at the party Jane and I hooked up with an older cousin of hers, (Rick) and sat at a table together. Rick was about five years older than us, vary handsome, charming, and a bit of a wild card. Jane busied herself drinking and Rick occupied his time trying to seduce me. I resisted nicely, reminding Rick I was married, but it only seemed to encourage him.

He served me Windsor and Coke to break me down as well as stroking my thighs under the table and putting an arm around me when the chance presented itself. I would gently remove his hand and politely again remind him of my marital status while secretly entertaining a fantasy in my mind.

I found myself disappointed thinking it may have ended when Jane passed out and Rick and I loaded her in my car to take her home, but once we got her in bed it escalated since we were now alone with only Jane awaking to worry about. I let Rick talk me into staying to have just a short drink before I left, (he decided he would sleep on the sofa). My mind raced wanting more attention, yet knowing I shouldn't sitting on the couch while Rick fixed drinks for us. I tried playing the good wife, but broke down when Rick slid over and kissed me then whispered, "Eati'n ain't cheati'n..." and gently nudged my head down.

I willingly slid to the floor and crawled between his legs while he undid his jeans and said something like, "Yeah, that's a good girl! A nice blow-job between friends never hurt anybody!". When he pulled his cock out I was amazed! I think it was over eight inches long, very thick, and dripping precum! I put my hand around it and stroked it a few times before sliding my mouth down over it. I had never had a cock that big before, but I was determined to suck it like I did on a regular basis.

As I slipped my lips over the head and my tongue orbited it Rick groaned, "Ahhh, that's a good girl! You like sucking cocks?"

"Uh-huh!" I moaned enjoying every bit of it, putting my husband out of mind for the moment! I worked my tongue and lips on his thick heavy cock with pleasure, even working my way down the shaft to his balls, kissing them and licking them while he stroked and petted my hair complimenting me on being a well trained cock-sucker before going back to the head of his cock to finish him.

After swallowing his cum and nursing his cock a bit he got up and refreshed our drinks telling me my husband would expect to taste a drink when he kissed me, but may be upset with another man's sperm on my lips. We talked a little finishing our drinks and he even hinted at having me over to his place in the future. We did meet again a few times, but it was always in the company of others and we never did anything sexual again, but it's always been one of my favorite fantasies.

Ashamed? Yes, a little...Regret it? Nope! I enjoyed it completely!
 
dirtycarol said:
Well, here goes!

I was married for only about five months when this happened. My best friend, Jane invited me to a large family party at a local Legion. My husband was working an extra job that night, but gave his blessing for me to go and have a good time.

While at the party Jane and I hooked up with an older cousin of hers, (Rick) and sat at a table together. Rick was about five years older than us, vary handsome, charming, and a bit of a wild card. Jane busied herself drinking and Rick occupied his time trying to seduce me. I resisted nicely, reminding Rick I was married, but it only seemed to encourage him.

He served me Windsor and Coke to break me down as well as stroking my thighs under the table and putting an arm around me when the chance presented itself. I would gently remove his hand and politely again remind him of my marital status while secretly entertaining a fantasy in my mind.

I found myself disappointed thinking it may have ended when Jane passed out and Rick and I loaded her in my car to take her home, but once we got her in bed it escalated since we were now alone with only Jane awaking to worry about. I let Rick talk me into staying to have just a short drink before I left, (he decided he would sleep on the sofa). My mind raced wanting more attention, yet knowing I shouldn't sitting on the couch while Rick fixed drinks for us. I tried playing the good wife, but broke down when Rick slid over and kissed me then whispered, "Eati'n ain't cheati'n..." and gently nudged my head down.

I willingly slid to the floor and crawled between his legs while he undid his jeans and said something like, "Yeah, that's a good girl! A nice blow-job between friends never hurt anybody!". When he pulled his cock out I was amazed! I think it was over eight inches long, very thick, and dripping precum! I put my hand around it and stroked it a few times before sliding my mouth down over it. I had never had a cock that big before, but I was determined to suck it like I did on a regular basis.

As I slipped my lips over the head and my tongue orbited it Rick groaned, "Ahhh, that's a good girl! You like sucking cocks?"

"Uh-huh!" I moaned enjoying every bit of it, putting my husband out of mind for the moment! I worked my tongue and lips on his thick heavy cock with pleasure, even working my way down the shaft to his balls, kissing them and licking them while he stroked and petted my hair complimenting me on being a well trained cock-sucker before going back to the head of his cock to finish him.

After swallowing his cum and nursing his cock a bit he got up and refreshed our drinks telling me my husband would expect to taste a drink when he kissed me, but may be upset with another man's sperm on my lips. We talked a little finishing our drinks and he even hinted at having me over to his place in the future. We did meet again a few times, but it was always in the company of others and we never did anything sexual again, but it's always been one of my favorite fantasies.

Ashamed? Yes, a little...Regret it? Nope! I enjoyed it completely!
Click to expand...

I'm willing to bet you have some incredible blowjob skills
 
The thing I should regret the most was cheating on my chubby Latina ex gf by sucking off random men off Craigslist behind her back, one was a chubby white gentleman who enjoyed cumming on my tongue knowing I had a gf. I ended up coming clean to her about it, I didn’t have to. She was horrified and on the point of having a nervous breakdown, we had a kid together and I was helping her raise 4 others. Me doing this destroyed our home and I should feel bad but I don’t.
 
OlFiddleMan said:
I'm willing to bet you have some incredible blowjob skills
Click to expand...

Since learning the proper mouth/cock technique and practicing it prior to getting married, I've only had one complaint, and I think that was out of frustration more than anything. An older guy that I had sex with 14 years prior got a part time job where I work and would pester me for a repeat performance almost every time he saw me, and every time I declined. One time he said, "You suck dick too hard anyway!" and left the area. He was upset, but maybe he had a point. He was uncut and someone said those are more sensitive...
 
Banging one of my sister in laws ( more than several times) before and after I married her sister. Last time was just a few months ago when she was in town for a writing workshop. My wife is very fun in bed. But Her sister fucks me like my dick has personally insulted her children.

She can be open and very free with me and no judgment. She was a bit of a party girl in college and husband is very uptight about it and is uncomfortable with anything he sees as beyond “normal” I’ve been in her ass with my tongue, fingers and dick, which the hubby flat out won’t do. she loves light domination, mostly name calling ( slut, etc) some light spanking and face fucking. she also loves getting her nipples fairly roughly twisted which he won’t do. He won’t even let her use a vibrator or dildo during sex. As far as I’m concerned nothing sexier than a pussy or ass or both filled with either one.

its only once every year or two but it’s very enjoyable.
 
When I was 20, I was dating an older married woman who had an 18 yo daughter. The mom and I would go out and fuck every chance we had. The daughter would hang around the house quite a bit, and it would damper our chances sometimes. The daughter found out about us (another story), and would be a thorn in our side some nights. Finally the mom told her she needed to get a man and get out of the house. Fast forward a few days, waiting on the mom to get home, daughter was there and I asked her didn’t her mom tell her to get a man, she says yeah but do what. I told her she needed to go, next thing I knew we were in the room and I was balls deep in her. I spent that afternoon and a few others fucking the daughter. Few months later the mom and I stopped seeing each other. Never told the mom, neither did the daughter, and 30 years later still don’t regret it.
 
Okay, this one is super weird. There was a time in my 30’s when I think my mother had discovered I was masochistic and liked female domination. She must have found something on my computer.

Here’s where it gets forbidden: She began to behave more domineering toward me like she was going to help me fulfill my fantasies. She started to make snide comments accusing me of being a gay bottom for men, asking me if I had gotten pregnant yet, etc.

I never defended myself when she spoke this way because I found it so shocking and HOT. So I had entered into a type of verbal domme/sub relationship with my own mother and I do not regret letting it happen.
 
waafist1977 said:
Hi, I'm new to the forum. Sorry for the long first post. I was on earlier reading a bunch of threads, and one that I can't find now about everyone on the forum turning each other on with their stories and such. It got me really horny and nostalgic about the best sex I've ever had.

I had been dating/married to my ex for 11 years, sex stopped after 8. It was a shame because she had a nice firm semi muscular body, a really nice tight wet pussy that was great the short time she was on birth control and didn't make me wear a rubber. And she had these awesome little A cup tits with eraser head nipples that stood up even more when you got her aroused. She had an inner freak that was into role play and light bondage, and she liked to be fucked hard, but she had severe hangups about exploring that and worrying about what her family would think if they knew. When I was game to do those things with her it just freaked her out more and over time poof, the sex was gone. So after 8 years of infrequent sex and 3 of no sex we got divorced. I was like a man dying of thirst in the desert.

Well, the ink wasn't even dry and I dove into the world of online dating, on a real site, not a hookup one, and the first girl I met was a fucking phenomenal lay. This girl was an emotional trainwreck from a breakup a few months before but we hit it off, seemed to connect emotionally, and were very open about our pasts. We met and went out a few times and things starting getting a little serious. On our 3rd date we made out on the couch, but she didn't want to have sex yet. She was a curvy girl, which is more of what I'm into, nice thick booty, pale skin, light brown hair and the second biggest pair of tits I've ever had the pleasure of having my hands on, about 40 GGG. Looking back I can tell you it was one of those things where just being around her made me rock hard like an 18 yr old, I was just turned on all of the time.

So a few days after the 3rd date she has the day off and I'm at work, we're supposed to go out later that night. She texts me to see if I can come over early, so I make my excuses to my boss and leave, I think I said something about it being Friday and I was going to go get laid. I get over to her place, we talk for a bit and start making out with her on my lap. I'm touching her everywhere, and get her shirt off. I slid my hands up under the cup of her bra to free her breasts and she reaches up and unhooks it so fast I think she was thinking it was about time. I remember telling her that her jeans were in the way too, and when she stood up to take them off I just took her by the hand and took her back to her bedroom.

I like taking my time in bed, building the anticipation, feeling over clothes when I'm touching someone new. I loved hearing her breath catch as she touched my hard cock through my jeans, knowing that we'd be getting a lot more familiar in minutes. My clothes came off and she turned herself around to play with the precum on my swollen head while I pulled down her wet panties to see a freshly shaved pussy. I slid my finger in and it was enough to make her cum. It wasn't loud, and her convulsions weren't very noticeable, but it felt like she was grabbing my finger and wouldn't let go. When she finished she asked if I thought I could make her do that again. Of course! She moved her body to position herself over me and rubbed my cock against her lips. She asked "is this ok?". I thought it was a weird question until I realized later she meant without a condom. In all honesty, my answer would still be the same even to this day. That's the thing I should regret but don't, if I could have somehow made this work I wouldn't be writing this, I'd be in her now and as frequently as I could. She rode me until she came again. She rolled over onto her side as she basked in her orgasm again and I didn't let her rest. I slid into her from behind, fucking her slow for a few minutes and made her cum another time. She told me she wanted me to finish and got on her hands and knees. I don't know where this stamina came from, in the past I would have ejaculated with her riding me, but I fucked her hard, fast, and long enough to make her legs shake under her as she climaxed two more times. She rolled over onto her back and pulled me into her, wrapping her legs around mine as I moved in and out. Finally she whispered in my ear "come on baby". Years of sexual and emotional neglect came to the head of my cock, because her saying that, making me feel like I was the thing she wanted most in the world made me explode in the best orgasm I've ever had in my life, more mind blowing that the first one I ever had as a teenager, and everytime I was with her I remember it being the same powerful orgasms. A few days later after she gave me a blowjob she made a comment on how much cum I put out, with her it was easily 3x as much cum as I normally have.

This relationship didn't last very long, maybe it was because we stopped doing anything else and fucked all of the time, which is normal in a new relationship. She definitely instigated it frequently, and felt the same insatiable horniness I felt. I remember her telling me once that she didn't know why she was so constantly turned on or why she was cumming so easily, but she loved that she could reach for me and I was always at least semi hard. We were like each other's viagra. In the end I think she ended it because it made her remember being in her previous relationship, I was apparently a lot like the ex-boyfriend that had dumped her, and she had been in love with him. But over the next couple of weeks she and I fucked at least 15 times before she abruptly ended it, and no sex I've ever had even holds a candle to any of those times.

So, unprotected sex and cumming inside a girl I hardly knew was dumb as shit, and if I knew what it was that turned me into Superman I'd find it with my current wife so I please her more and so I could cum that hard and that often again. I think I'm going to go wake her up now to give it a try.
Click to expand...
Yeah, it's awesome, I met a married last & she's been starved for years. We bang & kink at every opportunity we get. I especially luv that she hasn't done alot so everythang she's read about, but never had, thus we're ticking those boxes quite a few at a tym. No protection needed evr & she's ab absolute thrill evrytym we meet. I should, but nevr regret meeting her
 
There was a brief period when I was breaking up with one girlfriend and starting up with a new one. There may have been a day or two when I had sex with each one in the same day. It was what I've always wanted my life to be like, but it wasn't right.
 
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.
 
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.
 
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