Your biggest regret sexually

[wnjcwjkk]

A missed opportunity, perhaps?

I may just have everybody on here beat, but you never know.

I was a late bloomer, had a smaller than average cock for a long time. Even after it developed, I still had a negative body image and major insecurity. Ever since the first dick I saw, this guy pulled out a huge two hander dick, mine didn't even go halfway up my palm, it made me feel inadequate and insecure.

I'm a pretty good looking guy in the face. I changed schools to a really small Catholic School, where a new face was a big deal. ALL the girls were interested. A group of girls even came up to my sister in the mall to tell her "Your brother's hot!"

These two hot girls three way called me one time. I kid you NOT, when I saw this photo on The Chive I wondered if this was Jessica, it's not but the resemblance is uncanny.

"Do you think about us when you jack off? How big is your dick?" Is exactly what Jenna said. "So, when are you gonna suck his dick?" She asked her friend.

"Whenever he wants me to, I guess." Said the friend. And she was dead serious! They were sexually active, talked about guys with Big Dicks, which was intimidating, I didn't know how to handle it.

When I think about the list of girls I had a chance with and blew it, it makes me wanna punch myself in the face lol. I was so shy, had no game, had social anxiety disorder BAD, and was afraid to show my dick, my worst fear was for it to get around I was "tiny" (like I said, my dick was much smaller at once).

One time, I was drunk on whiskey with this hot raven haired chick, we made out for a while, Ididn't know how to seal the deal, got scared, she lightly grazed her hand across my lap, touching my head, making my hard cock go down, and the panic alarm went off. God, I was so stupid.

I wish I could show photos from FB of the chicks, but that's not cool, but there's a list I run through in my head sometimes and think "You stupid son of a bitch!" Haha

I lost my virginity at age 23 and then realized my dick had developed right under my nose (or belt) that it was actually bigger than average, something I never thought I'd actually have.

I made up for my mistakes with a couple girls from my past that I reconnected with on Facebook, even got to send them some pics and have them tell me how big I was "Why didn't you tell me back then?" And I'd think "Cause it was small back then..." Haha

 

[thomrisson]

Not a special incident but more like a phase I had. Try to keep it as short as possible to give the whole picture:
I had my first girl-friend when I was 14, we got serious pretty fast, I ended it after 2 years, had two other girl-friends after her, got back together with my first girl-friend at age 19 (I thought I made the biggest mistake of my life splitting up the first time), I was happy, but she cheated and she split up just before I turned 21.
I fell in a hole. I was cynical about relations and love, even women in general. Thought I was worth nothing, didn't even make moves on other women, actually I felt sexually not interested at all in anyone. It was all just people. Of course I masturbated a lot but didn't reflect the whole thing in any ways. At that time it never bothered me, but now it sort of does
I was just about to turn 25 (so the phase was 4 years) when I ended up with in bed with one of my ex'es sister (one of the other two girl-friends I had) accidentally. Like really, really accidentally. We were sharing a bed after a party, I was still in this cynical mood I just described, she approached me and it just happened. I really didn't expect it to happen. Anyways, I drove her home next morning, we had a quick chat on how to deal with it and agreed on keeping it a secret, but she told me, that her sister told her, that I was pretty good in bed, and that she can confirm on this. Something I never considered or was told before. I deflowered all my girl-friends, so they had no comparison. But it was the ego-boost I needed.
That happened just before I went to the UK for 9 months for studying. So I was there, foreign country, nobody knew me, and I really went on preying women. I consider myself not too attractive, but I realized, it doesn't matter (too much) if you bring the right attitude and deliver afterwards. No offense, I still find UK women easier to hook with than german women, plus there were a lot of female international students who had the same approach, just enjoy whatever comes up, cause back home nobody will ever know.
Long story short, it's been almost 4 years since I got my "mojo" back and I really enjoy it. I'm exploring myself, my needs, kinky stuff, I'm open minded about a lot of things, sexually curious, etc.
So I basically regret those 4 years in my early twenties. Lucky me, I have good stamina and women enjoy being with me, so I hope I've not missed out too much, but yeah, from nowadays perspective, lost years

 

[Hothrod]

I'm not one for long posts (I'd rather blog) but I regret not loosing my virginity until what would be considered 'late' or even 'very late' in life by today's modern standards.. 33!
I rationalize it by the strict conservative middle class upbringing I had in the pre AIDS days... yes, I'm that old... lol... and the fact that I considered myself ugly as heck because of serious acne condition..
Anyway, I'm too old for acne now, so its no longer a curse!

 

[Hothrod]

Damm, pitty we can't edit our posts... but I'll add to my above post that during the rise of AIDS, i was paranoid about anyone's body fluids coming anywhere near me... at least that was the community's understanding of how AIDS could be transmitted back in the 1980's.. little did we know about it then..

 

[bigbucky]

always wanted to bed a particular lady when I was younger. we were friends. hung out some together, but not on the same social level. I let her know a couple times that I wanted to be more than just her friend. now many, many years later, she realizes that she should have given me a chance. I'm a far better person than most guys she has dated and lived with and certainly better than her 2 ex-husbands.

 

[lapdog2001]

My response from a very similar thread in this same forum:
http://www.lpsg.com/threads/wish-you-had-before.426066/#post-5660362

 

[wnjcwjkk]

Not a special incident but more like a phase I had. Try to keep it as short as possible to give the whole picture:
I had my first girl-friend when I was 14, we got serious pretty fast, I ended it after 2 years, had two other girl-friends after her, got back together with my first girl-friend at age 19 (I thought I made the biggest mistake of my life splitting up the first time), I was happy, but she cheated and she split up just before I turned 21.
I fell in a hole. I was cynical about relations and love, even women in general. Thought I was worth nothing, didn't even make moves on other women, actually I felt sexually not interested at all in anyone. It was all just people. Of course I masturbated a lot but didn't reflect the whole thing in any ways. At that time it never bothered me, but now it sort of does
I was just about to turn 25 (so the phase was 4 years) when I ended up with in bed with one of my ex'es sister (one of the other two girl-friends I had) accidentally. Like really, really accidentally. We were sharing a bed after a party, I was still in this cynical mood I just described, she approached me and it just happened. I really didn't expect it to happen. Anyways, I drove her home next morning, we had a quick chat on how to deal with it and agreed on keeping it a secret, but she told me, that her sister told her, that I was pretty good in bed, and that she can confirm on this. Something I never considered or was told before. I deflowered all my girl-friends, so they had no comparison. But it was the ego-boost I needed.
That happened just before I went to the UK for 9 months for studying. So I was there, foreign country, nobody knew me, and I really went on preying women. I consider myself not too attractive, but I realized, it doesn't matter (too much) if you bring the right attitude and deliver afterwards. No offense, I still find UK women easier to hook with than german women, plus there were a lot of female international students who had the same approach, just enjoy whatever comes up, cause back home nobody will ever know.
Long story short, it's been almost 4 years since I got my "mojo" back and I really enjoy it. I'm exploring myself, my needs, kinky stuff, I'm open minded about a lot of things, sexually curious, etc.
So I basically regret those 4 years in my early twenties. Lucky me, I have good stamina and women enjoy being with me, so I hope I've not missed out too much, but yeah, from nowadays perspective, lost years

Sounds very similar to me, except I hadn't had sex at all. Just no confidence. But then, at 24, I hooked up with this little chick I knew in high school (we reconnected on FB). She was really petite, which made me look bigger, but also had grown some serious curves since I knew her in the past.

We fucked several times, she even watched me J/O in the shower (major fantasy from back then come to life!), she kept telling me how big I am, how good the sex is, I legitimately made her cum on multiple occasions, that was just the ego boost I needed to get out there and catch up on missed opportunities!

 

[wnjcwjkk]

always wanted to bed a particular lady when I was younger. we were friends. hung out some together, but not on the same social level. I let her know a couple times that I wanted to be more than just her friend. now many, many years later, she realizes that she should have given me a chance. I'm a far better person than most guys she has dated and lived with and certainly better than her 2 ex-husbands.

Is it too late for one of you now?

 

[bigbucky]

Is it too late for one of you now?

she is single again, but I am still married. we are also sixtyish in age. she is definitely not "hot" anymore. and sex is not a priority. she is a post menopausal woman, very little drive. I am in good shape, but not what I once was. she has come on to me pretty strong after a few drinks. she basically wants someone to take care of her, support her. a friend was with her for about a year. she got about $20k of his money. he paid a lot of her bills, and looked after her when she got too drunk. which can be almost daily. the sex he said wasn't too good and became almost non-existent.

 

[toolman4897]

Really for me its that until i found my recent girlfriend,that i held back trying so many new things..

She has really opened alot of doors for me and i believe we have just begun..

To bad the body doesnt work as good as it dud a few yrs ago..

 

[Trott.lint]

My current partner is the love of my life but she's very sexually conservative. If it was up to her, it would be 5 minutes of missionary once a week. Only because I push it do we end up doing it 2/3 times a week & I try to stretch the sessions to at least 20 minutes. Now my previous partner was sexual dynamite - everything was on the table including 69, oral sex, anal sex, sex three times an afternoon, every position in the kama sutra etc. But I completely took her for granted - I was in my early 20s & was far more interested in proving myself in every other aspect of life instead of locking down on sex technique & adventure. So I regret - really regret - the fact that I didn't appreciate that girl & have loads more fun with her.

 

[art]

My only regrets are that I didn't lose my virginity earlier, and that I didn't have more recreational sex when I was younger. I was way too picky about casual sex partners.

 

[Hatt_101]

Don't have one at least not yet

 

[mediaman004]

Definitely regret not losing my virginity earlier. I was raised in a fairly strict, religiously conservative family where sex was practically taboo, acceptable only after marriage, for the purpose of procreation, and girls I dated were supposed to be virgins (you wouldn't beleive the fallout when they realized I was dating a divorcee years ago). I followed those standards for a long time and had some unbelieveably frustrating years. I did nearly everything except actual intercourse. Then I had a significant birthday and it dawned on me that no one really cared. I changed many of my attitudes, loosened up and found a whole new world when I began living for myself rather than others' approval. Wish I could go back and relive some past times and change the outcomes.

 

[conntom]

I was at the gym and a guy took an interest in me. We were in the showers stalls and he showed himself off a bit.. ..drying off afterwards I was sitting and he was standing - he came over to me,. Big long cock in my face and I didn't run with it.....

Still haven't ever done anything mm. That might have been fun....

 

[vagitarian]

I wish I knew how easy it would have been to get more action when I was younger. I was just such an inept flirt and was too concerned about being macho in front of my friends to invest any time getting the girls that liked me to fuck me. A quick flip through the mental rolodex finds a Playboy model-looking blonde I drunkenly made out with in a bar, a curly haired brunette from an Art History class I was in and hit it off with at a party, and this piercings and heavy eye makeup type girl that gave me great seductive looks when she hung out at my house, for starters. What a putz I was. Looking back I just know they all wanted it and it would've taken so little effort to close the deal. I wonder if any of them would've really liked sex a lot and it could've developed into a fuck-all-the-time kind of relationship.

That's another thing I've never had: a relationship with a girl that just loves to screw all the time. My wife is great and all but she doesn't have the "think about sex all the time" mindset that I (and I hope not exclusively men) have. I'd like to have been with a girl that wants to just grab my dick and ride it all the time or look at porno together and get turned on and fuck.

Lastly I also have unchecked boxes next to a few sex acts/partners on my list:

• Threesome with 2 (or more) girls,
• Blowjob from 2 (or more) girls,
• Mutual masturbation with 2 (or more) girls,
• Basically [fill in the blank] with 2 (or more) girls,
• Black girl,
• Tall girl (like me, my wife is short),

to name the ones I think about the most. Thanks for reading while I vent.

 

[archetypal_mystic]

Wow, similar regrets to mine have been expressed here - not losing my virginity early enough, not following through on a totally overt pickup at the gym....but my number one regret, because it could have changed the course of my life - was not being brave and agressive enough to fuck/ be fucked my best friend when we were 18 and curious and horny, but too afraid to even discuss the issue. It cause years of tension to build, and when we finally fooled around he was in a LTR and would only go so far...strong moral code or whatever. The situation still exists today...

 

[BaronSaber]

the women that I turned down becuase I didnt feel the situation right. Fuck it life is short, they were offering themselves I should have fucked em

 

[desilover]

i don't believe in regrets. though i want to experience being a bottom to a ten inch cock.....that's my main sexual life goal now as it were.

 

[longozzy]

Had a few regrets, but the one I regret the most was not going down on my girlfriend at the time (now ex obviously), now all these years later I think what a jerk I was for not doing it, and the thought of it now gets me hard as....