What is your biggest sexual regret, and why?

I had sex with one guy before I got married to my husband. I wish that I had waited for my husband. I wish that he was the only man to know my body that well. My husband is ready, willing and eager for sex any time and as often as I want it. He's creative, generous and it's always good.

I wish I hadn't wasted my first couple of times on bad sex that meant nothing and only left me feeling cheated.

Atleast the sex I get every day is amazing! Thinking of that leaves a better taste in my mouth. ;P

Having sex before your marriage could also be a positive for you.
The pre marriage sex guy was a bad lay, and you know your husband is a good lay, because of that experience.

If you didn't have the pre marriage bad lay period, and only had sex with your husband, you could wonder, then, how other lays would be.
 
It would take me 20 years..

just to whittle down my regrets to just one. And I don't have 20 years left.
 
My biggest regret is allowing my marriage to become a sexless, empty shell, not working harder to make it better. Now so many years have passed, so much space has be made between the two of us ... and while I am only in my 30s, I am pretty sure I will never know true intimacy, passion and lovemaking. I read alot and live vicariously through others.
 
Back in college I initiated an intense, very pleasurable sexual encounter with a guy in my dorm. I pretty much jumped his bones, getting him off orally before having him give me head until he was hard again, and then he vigorously fucked me until we both came. Sounds great, right? Well, thanks to too many wine coolers, darkness, lack of communication, and general carelessness, it turned out (as I discovered to my genuine horror the next day) that the guy involved was not the guy I thought it was. It was a friend of mine who was also the eventual fiance of one of my best friends. I was sick with guilt about this. Once I mustered up the confidence to say anything to him, I made him swear that he'd never say a word to anyone about what happened. To the best of my knowledge, he never did. I even went to their wedding a couple of years later, shaking hands and hugging on the receiving line with both of us maintaining the complete air of innocence that we got good at. The memories of that tryst are still maddeningly vivid, though.
 
Having sex before your marriage could also be a positive for you.
The pre marriage sex guy was a bad lay, and you know your husband is a good lay, because of that experience.

If you didn't have the pre marriage bad lay period, and only had sex with your husband, you could wonder, then, how other lays would be.

I wonder. Not that I'm dissatisfied with our sex life, don't get me wrong. I just have nothing to compare it to. I guess that's my regret.
 
I have many regrets, but one that comes to mind involves my mother-in-law, at their home, with a house full of family, etc. We were all drinking, playing loud music and dancing. My mother-in-law asked me to dance, and immediately thrust her pussy into my groin, and of course I immediately became hard. Instead of pushing back into her, and making things happen, I pulled, away, had to put my back to everyone who I thought could see, until my hard-on subsided. I would have fucked her in a heart beat, just didn't seize the opportunity of the moment.

I have fantasized many times about that how that scenario could have played out, usually while jacking off. Now she is out of my life, it is not to be...
 
My sexual regret isn't a sexual act that I pursued, or did not pursue. However, I regret taking out my hood piercing for my now husband. I got it a few months after we started dating and it kind of weird-ed him out a bit. He wasn't going down as often and i asked him why, he was intimidated by the piercing. I assured him that it enhanced anything that he does but he was still hesitant. So I took it out. I'm still mad at myself for giving in so easily and not trying to convince him otherwise.
 
not realising my bi-sexual tendencies until late in life ... so many missed opportunities
 
Worrying too much about the opinions of others and not experiencing the things I always wanted to experience before I got engaged.
If for some reason we dont end up getting married, I'm going on a 10 year tear.
 
Never getting the courage to out myself to my wife. Who knows she might like the freedom it brings me. Might never know.
 
Never acting on my bi urges. I wish I had the courage to hook up with another guy and see what it is like to suck a cock and have him cum in my mouth, feel a cock going in my ass and seeing if can feel it when he cums inside your ass.
 
Regrets;
various girls I could have fucked but didn't.. not fucking my first long term girlfriend in the ass when i knew darn well she would have liked it, but was to embarrassed to ask me...
 
haunted

Once at a party in college I found myself in a bedroom sprawled on top of a bed covered with coats. I was buzzed and crushing hard on my friend's guy pal visiting from home. He was so hot but so off limits because I knew she was kinda half in love with him. Anyway, as I'm laying there in the dark I hear the door open and in slips my crush. He flops down beside me and we start talking about music. At some point he starts running his fingers over the skin peeking between the bottom of my shirt and the top of my jeans. I'm holding my breath. He kisses me and I don't stop him. We're seriously making out and it feels fantastic but my heart is pounding because we could be caught any second. I can feel his erection pressed against my leg and I want it. He's got his hands down my jeans, working his fingers into my soaked panties, and his lips on the sensitive skin of my neck behind my ear. I'm about to come when someone slams into the door scaring me back to reality. I pull away, telling him that we have to stop. It would hurt our friend. He lays his head on my stomach, I run my fingers through his hair and we just breathe for awhile. Then he starts kissing my belly. He looks up at me, my fingers still in his hair, and says so sincerely it freaking hurt "Just let me go down on you? Please?"

Oh kill me, getting up and walking away from that was one of the hardest things I ever did. I didnt have much willpower in college. I dont know where I found it that night. I still hear his voice in my head sometimes almost 10 years later. I left school that year and didn't stay in touch with the friend I was so worried about hurting.

I should have done it but if I had maybe that would be my biggest regret too.

I've toyed with asking my husband to say those words to me but I'm afraid he'll want to know why. I don't want him to think I imagine another man with his face between my legs.
 
I have2…one was actually taking a girl who just wanted sex out on a date. I tried to hit it after that she was not interested because she thought I would want a relationship and she was not interested in that. The other was sleeping with my best friend (We were 19) at the time’s sister. He said it was ok but I still feel a little bad about that.
 
My regret of missed encounters is this An ex girlfriend with whom I had shared most of my fantasies invited me to visit her and her boyfriend to let me try out my bi desires. The idea of sucking him was great but was scared of being overwhelmed with jealously by her having sex with the BF so I could clean her up that I never made the trip. I also had the opportunity to fuck her on her wedding eve, but do not regret passing on that because the hubby (different guy) was not aware.
 
Missed Opportunity

This is just one of them. Back when I when to art school. I was visiting a friend of mine who's roommate happen to be my roommates girlfriend. One of the reason's I was there was to tell my roommates girlfriend that he couldn't that night. I'm not sure what the reason was, but it was a lie. He was really seeing another girl in our apartment at the time.

His girlfriend and I wound up alone late that night talking on the couch. She had a blanket over her and we laid under the blanket on opposite ends of the couch facing each other. In the middle of our conversation I felt her foot slide up between my legs and she started feeling my cock though my jeans. Not to be left out on the fun, I did the same to her. Kneading my toes into her pussy. She started moaning and she said she was so wet and horny.

I moved on top of her and we started kissing and grinding. She asked me if I had a condom. Luck would have it I didn't. I told her I could get one, but she didn't want me to leave. I asked her what did she want me to do, since I didn't have one. She said we could do "other things".

At the time I had no idea what she was talking about when she said "other things". I was 18 and I only had sex with one person before her. I knew what oral sex was but I had never done it before and going down on her never crossed my mind.

I wound up kissing her and grinding my fingers against her jeans. She got so wet that her jeans where soaking wet and she came. She fell asleep in my arms on the couch and we kissed goodby in the morning.

She would always smile at me when she came to see my roommate and it would bring back the memories of what we had did. I wanted more and I later realized that what she wanted was oral sex. I felt like such an idiot.

Much later she found out that my roommate had been cheating on her and I don't know if she knew I was covering for him that night.

I never got the opportunity to hook-up with her again. I did make sure that the next girlfriend I had I performed oral sex on her. Ever since then I have loved performing oral sex and love making a woman cum that way.

I only wonder if I could have done the same with my roommates girlfriend that night.
 
A few years after college I was living on my own in NYC. I met a woman at a club one night, and it was instant chemistry. We didn't have a passionate love affair, but we had a lot of fun and great sex. I'd dallied with a few women before, but she truly taught me how to be a good lover for another woman.

She was in med school, and her schedule was absolutely crazy. Many times she would invite me over, and she would end up falling asleep during what was meant to be foreplay. We always made it up to each other the following morning. :)

Anyway, my regret was letting her get away. We split up by mutual agreement because she knew her schedule was becoming more difficult and felt that I deserved more of an actual relationship. That would have been nice, of course, but I enjoyed the times that we did have. Sadly, the concept of 'friends with benefits' just didn't feel right to her. I should have been more persuasive.
 
Biggest regret?

Being too unsure of myself to say "You're hot, I like you, can we keep talking?" to the one who helped me start my journey of self-discovery. Always too much in the shadows, or afraid of being a pest. Wanting to say so much more, but never disclosing enough. Finally growing enough confidence to start sharing just in time to be told he's found another.
 
Stalled?

I seem to have killed the thread. Just never mind me guys, go ahead and return to your normally scheduled programming...
:rose:
 
I seem to have killed the thread. Just never mind me guys, go ahead and return to your normally scheduled programming...
:rose:

You haven't killed this thread, it sometime takes a little bump to get things flowing back again. :)
 
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