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

[waafist1977]

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.

 

[waafist1977]

Pic for reference

Obviously this girl isn't her, but the body is her almost exactly.

http://images.shoprw.com/belliesinbloom/Cake-Lingerie-Sorbet-Wirefree-Bra_21426A.jpg

 

[newhere2learn]

She's hot... Two spring to mind

First, long term girlfriend was a nightmare when drunk, all over other guys. Anyway, like most 18 year old, we were on/off like a lightbulb.

Her then best friend was also a friend of mine, who was kinky as, and having a dry spell. So, I assisted for a while becoming FWB on the side.

One night, early evening we're having much fun, resulting in mutual climax by way of a very sensual 69 which too a while, but was amazing. I've just cum all down her throat, cock still wet, and my phone beeps. On/off GF wanting me round, for sex.

FWB doesn't miss a beat:

"Go now, fuck her hard, think of me"


I did. In under an hour, I was cumming for the second time, bareback with her on all fours... After she'd sucked me clean, probably tasting her friends saliva and juices. Then text FWB told her all about it, to which we mutually got off a couple of night later.





Second, former colleague, 15 years older. Both single, bumped into her in a pub.

End of the night, all 3 holes, bareback. Cum in each, before she left at dawn.

Big girl, zero self respect, but God she loved to fuck.

 

[Up_Up_Down_Down]

Years ago, became friendly with a young married colleague. Woman was kinda hot mess. High strung, married straight out of college, bought a big house they couldn't afford on their salaries (they both came from well-to-do families), being pressured to get pregnant but didn't want to until finances were more stable, high stress at work, etc. And, well, we were friends, but she really did it for me. Over 6' tall, brunette, athletic, long hair, very attractive with a great figure. I have a thing for tall woman.

One day, she has a meltdown in the office. Just a complete overstressed mess. As her friend, I'm trying to calm her down, and she decides she needs to take the afternoon off. I go with her. I'm thinking that she probably needs to be taken home and unwind with a couple drinks, but instead we end up at my townhouse.

We go in and just talk for awhile. Whole time, my head is spinning like I'm in a Bugs Bunny. cartoon. There's a little guy with angel's wings telling me to get her out of there, and his counterpart with devil's horns whispering that I should go with the flow and follow her lead.

Long story short, we end up in bed fucking like bunnies in a whole lot of positions and holes. She's not really that kinky or adventurous, but this day, she's willing to follow my lead. So I have every hole and we do some really interesting stuff.

At one point, she's riding me reverse cowgirl and catches a glimpse of herself in the mirror, starts crying. I immediately pull out and start comforting her. No, she tells me, the sex is what she needs. She's just remembering her screwed-up life and job. I definitely should have put an end to the festivities then, but instead, I flipped her over and fucked her harder, belly down/prone-style.

I was kin of a jerk about the whole thing and regret in now. But, damn, the sex was great. Her husband was out of town for the week, so she slept over for a day or two and we did it every chance we got. The standing doggy in the shower two mornings later was especially memorable, given her height.

We talked about it later, and she didn't feel like i took advantage, but i still feel kinda bad. The episode was kinda out of character for me. I don't really regret it, though. I figure everyone deserves a mulligan once in a while and the sex was about as good as I've ever had. That was probably the only opportunity I ever had with her, so I would have probably wondered about it ever since if I had shut it down early.

 

[soflabbwlvr]

I was home from college for the weekend. It was Saturday morning and everyone was at work. I had the stereo blasting at 11 and I was burning a fatty for breakfast. The song ends and I hear a violent pounding on the back door. I go to check it and find a skanky but cute redhead asking for my brother. She was wearing tiny cut off shorts and a white tank top that barely covered her ample tits.

She was pissed off when she got there, and even more irate when I told her my brother wasn't home. I let her in so she could see for herself that he wasn't there. Finally convinced, she turned her attention to me. I rolled another and burned it with her, and then led her to the bedroom. I dropped my shorts, nudged her to the floor, and had my cock in her mouth a few seconds later. When it started to feel good, I helped her to the bed, pulled off her shorts and panties, pushed her knees up to her shoulders, and entered her. I fucked her hard for several minutes, then flipped her over onto her hands and knees. We fucked doggy style for a while, and then I felt my orgasm building. I asked her if she was on the pill and she said "no." I pulled out and shot my load all over her back. Her tank top was soaked with jizz. It was a huge load. I stood up, got dressed, and sent her out the door wearing her cum-soaked shirt.

I should feel bad for the way I treated her, but I never did. I have felt far worse on occasions where I treated women much less terribly than her, but I always felt that she got what she deserved.

 

[newhere2learn]

I should feel bad for the way I treated her, but I never did. I have felt far worse on occasions where I treated women much less terribly than her, but I always felt that she got what she deserved.

A theory I wholly subscribe to.

My wife had a phase some years ago, put me through hell for months on end. Even filed for divorce, and made false claims to the police.

Anyway, reconciliation sex was had. Filthy, dirty, hate-fuck sex.


For several weeks, each night she was left with cum (which she hates) all over her or leaking out of the holes she doesn't want it in.

Zero fucks given.

Ironically, deep down she must have liked it, as in a decade, it's still the hottest sex we've ever had.

 

[thespiceoflife]

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.

great first post

 

[UnderMyKilt]

Obviously this girl isn't her, but the body is her almost exactly.

http://images.shoprw.com/belliesinbloom/Cake-Lingerie-Sorbet-Wirefree-Bra_21426A.jpg

Twenty years ago, that was my wife...and she's still damned sexy.

 

[Erlikkhan]

My story is much shorter. I fucked my wife's best friend. She was married to a guy we both knew but that I didn't like much. We had sex over a two month period. Several times we did it in another room with my wife at home and one time at her place with her husband home. Apparently I wasn't the only guy fucking her. Her husband caught her but never found out about me (nor did my wife) but that ended our trysts.

I have no regrets.

 

[Lost_Yonder]

I was home from college for the weekend. It was Saturday morning and everyone was at work. I had the stereo blasting at 11 and I was burning a fatty for breakfast. The song ends and I hear a violent pounding on the back door. I go to check it and find a skanky but cute redhead asking for my brother. She was wearing tiny cut off shorts and a white tank top that barely covered her ample tits.

She was pissed off when she got there, and even more irate when I told her my brother wasn't home. I let her in so she could see for herself that he wasn't there. Finally convinced, she turned her attention to me. I rolled another and burned it with her, and then led her to the bedroom. I dropped my shorts, nudged her to the floor, and had my cock in her mouth a few seconds later. When it started to feel good, I helped her to the bed, pulled off her shorts and panties, pushed her knees up to her shoulders, and entered her. I fucked her hard for several minutes, then flipped her over onto her hands and knees. We fucked doggy style for a while, and then I felt my orgasm building. I asked her if she was on the pill and she said "no." I pulled out and shot my load all over her back. Her tank top was soaked with jizz. It was a huge load. I stood up, got dressed, and sent her out the door wearing her cum-soaked shirt.

I should feel bad for the way I treated her, but I never did. I have felt far worse on occasions where I treated women much less terribly than her, but I always felt that she got what she deserved.

For whatever reason, but that story is so fucking hot! Both in how angry she was about your brother and in sending her off with her cum covered shirt!

Shameful! Shameful!

 

[curl4ever]

A year-long “girl friend experience” relationship with a call girl because my wife wouldn’t have sex with me. I always brought champagne.

- curl

 

[JJElsee]

Having an affair with my sister in law, I know I should regret it but the sex was amazing, intense and it was pure uninhibited lust. She is a sandwich short of a picnic and almost a stalker but even now I have trouble keeping my hands to myself when she’s around.

 

[screwher]

I guess I should regret not dumping my wife the first time she cheated on me.

(But I didn't. In fact her tryst started to arouse me. I secretly wished she'd do it again)

Once a cheater, always a cheater. I should regret not leaving her ass the second time she cheated.

(But I didn't. In fact I confessed to her my secret desires for other men having sex with her. Now we're in an awesome hotwife relationship!)

 

[LekaSveta]

Having a sexual relationship with my high school English teacher (I was 18 when it started) I was the only out lesbian in my tiny little school district (83 people in my graduating class) and she was deeply closeted. She gave me a ride home one day after a Creative Writing workshop, during the ride she asked me a lot about what coming out was like for me and confessed she was attracted to other women too, but never had the courage to be open about it and it had been years since she was intimate with anyone, even he husband. She was fairly young and quite pretty so I put my hand on hers and moved her hand to my thigh and up my dress, she drove right past my house We were lovers for about two years until she finally got the courage to divorce her husband and come out, the school promptly fired her and she moved away.

 

[Lucien_Al]

Wife's best friend

In a way, I regret what I did but the pleasure almost made it worthwhile.

My wife's best friend's husband was away on business and she came to a party at our house. We all ended up in the pool and I was perving hard and could see that she was enjoying it and starting to flirt back.

We were going through a very dry spell and I was as horny as fuck.

My wife went to bed early and we ended up sitting alone at the bar once everyone had left. After a while, we were sitting facing each other and our hands were on each other's upper thighs. At this point, it was clear that she was just as keen to progress this as I was. She had intended to stay over rather than drive after a few drinks and we ended up in the spare room.

She started by sucking me off and then we progressed to a hot 69 for a while. SHe made it clear that I could not fuck her as her husband was snipped and she wasn't on birth control. After she had cum a few times she sucked me like a pro. The best BJ I have ever had and she swallowed every drop. I slipped back to our room and the wife was still fast asleep and unaware. The next morning I found out that she was on her period when I had been eating her pussy.

I did have a few issues with her later as she felt guilty about cheating on her mate and at one stage she suggested we tell the wife. Thankfully I was able to dissuade her.

On the pro side, she was the most beautiful woman I have ever been with a true dancers body. She was the most skilled BJ giver I have ever come across. She had the most beautiful looking pussy.

On the negative side, her guilt ruined the friendship with my wife and the risk I took was just dumb.

The fact that she was on her period while I was eating her didn't bother me as much as I thought it would have.

 

[AficionadoAngel]

Having sex with one of my ex-boyfriend's friends after we broke up and telling him about it. I divulged what a machine this guy was and how he did me did me five times in one night. I thought it was a turn-on for him, and maybe it was, but afterwards I realized that a part of me was being cruel.

 

[19jimbo99]

So years ago in my twenties I fucked my girlfriend's mom and then she found out about it .it made a mess of the whole trust issue between her and her mom and trust issue between her and I .I felt like shitt but I still don't regret it mom was awesome..

 

[LauraWilling]

I've had a few lovers and Dom's who pushed me willingly "out of bounds" a few times and I knew I should have tried to stop it but always after the fact. One will remain my secret, but exhibited in compromising, degrading ways. Multiple partners, Shared by my husband with friends and sometimes strangers.
Some I loved, some were fun, but take it or leave it and a few I would rather not be placed in again. But over all I would say I do not regret most of them and glad I at least tried them.

 

[HoldYouDown]

Some really good stories on here. I'm trying to remember if I have any. I guess it would be fucking various girls who had serious boyfriends. But that doesn't seem to measure up to what I've been reading on here...

 

[Cindy69love]

My sister's wedding

I actually had sex with her new husband at their wedding reception...

 

[19jimbo99]

I actually had sex with her new husband at their wedding reception...

Wtf..winner winner chicken dinner!!!

 

[Cindy69love]

Wtf..winner winner chicken dinner!!!

I got a bit drunk... and did a bit more with a few of his wedding party.

 

[Dreamer110]

I got a bit drunk... and did a bit more with a few of his wedding party.

Definitely in love.

 

[Cindy69love]

Definitely in love.

Scary thing was my husband was still at the reception.

 

[Dreamer110]

Scary thing was my husband was still at the reception.

Hope he got some nice sloppy fourths