What is your biggest sexual regret, and why?

My biggest regret is not exploring my sexuality in my late teens early 20's, I am 30 years old now and very bisexual with not very much experience, I turned down a lot of chances to be with men when I lived in California but I turned them all down.

You still have lots of time. My forties were the best years of my life, sexually speaking. Get out there and live, my friend.
 
Two things, one as I was getting to move from NM a woman I had been pursuing for years came over to hang out "one last time". She suggested we get some ice cream before going back to my apartment. When we got there she said she always ate ice cream in her underwear so we stripped to our skivvies... and ate ice cream. It didn't dawn on me that she did not in fact eat ice cream in her underwear. That this gorgeous busty red headed woman was inches from me and nearly naked and I should jump on her. What a moron I was.

Second, I dated a verifiable certifiable nymph right after my divorce. She would do anything, try anything, do it anywhere I wanted... and I broke up with her after two weeks.
 
My biggest regret is two fold and tricky. I both regret something I got myself involved in and at the same time, sometimes I regret not allowing it to go further than it has. Like I said, it's a bit complicated, but there are certainly regrets.
 
I didn't have my epiphany sooner and the 25 yrs prior were not fun or enjoyable sexually. So now I enjoy every day and try to make up for those terrible years. I try to make my hubby happy and in doing so I'm really happy too. But I live every day to the fullest and enjoy my sexuality now no holds barred. :rose:

So you are 'making up' for those years. Have you ever thought, though, this reawakening would so great without those lean years?
 
I went to school with her.
She invited me to a party at the hotel where she worked as a bartender.
She was ready and willing..I was drunk and passed out on the floor.
The next day was the worst hangover I've ever known.
 
regrets I have a few

regrets I had no control over: being born with a cock that will never get over 4" hard and most of all having my foreskin cut off as a baby
regets I had cintrol over: never exploring the gay side of my personality earlier and also not having the courage or knowledge of women so I misse dseveral opportunities to fuck some nice women
 
regets

I regret not going through with my ultimate fantasy when i had the chance.
One thing guarranteed to turn my head is a guy in uniform. Just the thought of stripping them naked gets me all hot and bothered.
When i was 19 my then bf took me for a drive in the country. We got flagged down by a young soldier who wanted us to help him move a vehicle that had got stuck. To say i encouraged him to help was an understatement, when we got to where the vehicle was i noticed there were about 8 other soldiers and i joked to my bf that i could show them a few good things. He mentioned to the guy in charge what i had said and the guy replied that he would love to show me what his men were capable of.
My bf offered to leave me there with them for a few hours but i decided not to take them up on the offer.
Looking back i regret not staying and seeing what the British Army was capable of.x
 
For me, it was the fact that I was way too shy and feared rejection. Because of this, I was afraid to ask girls out or make a move when one presented itself. Looking back I can now see a number of situations where the girl was giving me all kinds of signals, but I was clueless at the time. I ended up a virgin until I was 23 years old.

Yeah. That. Admittedly, my expectation of rejection was justified since there was definitely a positive feedback loop between the prolonged virginity and the behavior that made me so undesirable. But even though I still couldn't tell you which those situations were, I'm sure there were a few I missed out on.
 
That I never let my Dad fuck me.
We did other stuff but I was so hung up on the "this is wrong in societies eyes" shit that I never let it go further.
 
My regret is that I've never been bold enough to be with another woman...or a threesome..I've always had both fantasies in my head..my regret is that I haven't been bold enough to go and get what I want...and I want it...
 
My regret is that I've never been bold enough to be with another woman...or a threesome..I've always had both fantasies in my head..my regret is that I haven't been bold enough to go and get what I want...and I want it...

Go and get it honey! You will love it. :)
 
I've had sex with 4 people and I've regretted 2 of them.
 
I'd have to say my biggest sexual (and relationship) regret would be not having went for a friends gorgeous sister who wanted me. I didn't want to upset my friend if he wasn't good an gravy with me and his sister dating/fucking. God she was a looker. 5'4 with deep auburn hair that when the sun hit it it was fiery. 32 D with curves an hourglass would be jealous of and an ass I had the pleasure of accidentally grabbing in a crowd. Firm but soft. She wanted me and my first clue was when I accidentally grabbed her ass. She gave me a coy look that hardened me good. I was fortunate to have slept with her once and it was amazing. We were drunk and it was at a Christmas party, she was 19 and I was 17 going on 18. We sneaked some of the spiked punch and jello shooters and ended up under the mistletoe. Before we knew it we were in her room making out. We had sex several times. Even moved into the basement where we ended up passing out and thank God woke up a bit later before anyone could come looking for us in the morning. I slept on the couch once everyone had gone home, best friend went to his room and she wanted me to come to her room but I was afraid her pa would catch us so I declined and she understood. In the morning when we could get alone I told her we couldn't because her brother and while she looked disappointed and hurt she understood. She went to college a while later having decided to pursue a law career. I really regret not having at least tried to talk to my friend and gotten his permission or something. She was a sweet girl and a nymph in the hay.
 
That I never let my Dad fuck me.
We did other stuff but I was so hung up on the "this is wrong in societies eyes" shit that I never let it go further.

I have the same deal but with my sister..im 42 and she"s 45...If we could do it we would..Ps..I would have given her my baby seed as well...
 
I wish that I had waited

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
 
two regrets....

Have two...

First is that I disn't accompany my female (three sisters) cousins and their friends on their camping trip one summer when I knew they'd be skinny dipping much of the time. I helped them settle in, but went back to the cottage since I was too cowatdly to push to stay.

Second was not taking up summer students on their sexual offers before I got married. (Not a complaint about marriage, just wishful thinking.) No longer work at the place, though they hired dozens of interns each summer.

Could have better stories if I was not so timid!!!
 
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

At least you have a term of comparison to state that your husband is a good lover for you ... imagine if it were the other way around ;)
 
My biggest sexual regret was I never explored my sexuality in my teenage years and in my twenties. I was a very quiet person and I didn't get asked out a lot by guys plus I was too shy to ask anyone out anyway.

If I had the chance to do it all over again, I would do things differently.

Very much the same for me, how hitting 40 has changed how I feel and act!
 
I wish it hadn't taken me until my 30's to find out what it's like to have a lover who looks so good that I want to stare all the time.

In my life, I've been involved with people who looked a little awkward, okay, or even pretty nice, and I've been happy to see them naked in my bed in large part because I really, really liked them. Only recently have I discovered how nice it is to be with someone I really really like and who I also find really, really physically attractive. I used to want to roll my eyes whenever a guy told me that he sometimes liked to watch me sleep, because I found sleeping people pretty dull. Now I understand the appeal.

I'm not planning to suddenly become shallow and exceedingly picky about appearance, but it sure is nice when things turn out this way. I wish they'd turned out this way sometime before now.
 
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I firmly believe that one day as you lay alone in your final days, your greatest regret will be:

NOT living out your fantasies.
 
Biggest regret? Hmmm....I'm not sure I can regret something that hasn't happened, but I do suffer some....knowing that I'll likely never be with him in the flesh.

I think I'd give just about anything for that experience. To know his touch, his taste, his scent...those vital pieces of HIM that my mind and body crave. It aches deep inside to know all I can give are words when there's so much more, just for him.
 
I wish it hadn't taken me until my 30's to find out what it's like to have a lover who looks so good that I want to stare all the time.

In my life, I've been involved with people who looked a little awkward, okay, or even pretty nice, and I've been happy to see them naked in my bed in large part because I really, really liked them. Only recently have I discovered how nice it is to be with someone I really really like and who I also find really, really physically attractive. I used to want to roll my eyes whenever a guy told me that he sometimes liked to watch me sleep, because I found sleeping people pretty dull. Now I understand the appeal.

I'm not planning to suddenly become shallow and exceedingly picky about appearance, but it sure is nice when things turn out this way. I wish they'd turned out this way sometime before now.

That is lovely, I suppose experience has made you appreciative ?
 
Well it is kind of my fault, since I knew what I was getting into, my friend warned me, but I went through with it anyway, but still, thanks for saying that. Yeah, I feel pretty disgusting everytime I think about it, and no, my friends and I don't really talk about 'feelings', and I don't have a therapist or anything like that, I'm just hoping that I'll stop looking at it as such a big deal, I guess I'm just sensitive.
(Assuming you were talking to me anyway, if you weren't just ignore this hah, and sorry for being such a downer haha)
Fault has nothing to do with it. No one has a right to treat you that way. That's abusive and wrong. That's the same "blame the victim" thinking that so many people use. You did not deserve to be treated that way. You are a worthwhile human being,and the only thing that I can suggest for the future is to try to seek out someone who makes you feel good....who makes you feel safe and cared for, and then you can experiment sexually with them after you feel comfortable. You deserve better. Just my two cents.
 
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