What do you sexually regret that you did not get to do?

I will provide some examples so you know what I am talking about:

- My sex life started by fucking with girls from the local all girl catholic HS's. At each of them, their uniforms were a polo and a knee length miniskirt. I regret that I did not get to fuck a girl in a 100% real school girl outfit. Not one of those Halloween costumes. The one time I for sure knew I was going to get the chance. The girl changed into jeans and a T-shirt before coming to pick me up.

- One time I was hanging out with two drunk chicks I met the night before. The one clearly had her eye on me and eventually she grabbed my hand while the other whistled at us. I had sex with her while her friend was laying on the couch outside our door. I regret not attempting to invite her friend inside.

 

The time for regrets is the day before you die!!

Thinskin

 

I regret not fucking my friend in the ass when we were younger and playing around. We sucked each other off plenty of times, but when he asked, "Do you want to put it in?" I froze and said no. Sometimes I still think about what it would've been like to cum in his tight ass.

 

Not having a threesome of any kind. The one we fantasize about the most is with a shemale. Never had the courage to try. Maybe someday.

 

For me...joining two twins for a threesome. I didn't do it cause I was taken, though I was going through with a rough patch with my gf at the time. The worst bit..my roommate at the time took my place..said they made his cock shoot dust, lol.

 

I regret that in last sex party 6 years back there was 14 female and I was only man there I just fuck 6 of them other are leave unfuck by me due to too much boozing and I pass out sob sob sob sob sob

 

1 I regret stopping my cousin after she jumped on me wanting to fuck, I had started it and ended it, even though I'm sure it saved our relationship, I'm being selfish and wish I could have more memories of playing around with her
2 when any chick I messed around with didn't wanna have sex (which is cool), I didn't just ask for at least a bj or handy lol

I'm sure I would have had a couple

 

I picked up a hotie in the bar ...in the hot tub we made out & I was trying to suck his dick but he wanted to fuck me ...I wasn't into it so he left ...gawd I wish we fucked

 

I regret not being unfaithful to unfaithful woman.

 

Not knowing how to handle a pre operative transsexual to the point where we could fuck, after her giving me head I offered to go down on her cock. It brought back memories to Samantha of guys who were looking for something freaky rather then me just wanting to please her too.

 

Didn't realy have much to turn down, so not that much to regret on that side.

So - time.
My only real regret regarding my sexuality is I didn't pursue it sooner. I settled for less. Not even less than I wanted, but less than what clearly was achievable.

 

The only regret I have are the ones I didn't pursue. Time and effort were a factor to those.

 

Regrets, none. Those things I didn't want I could not stop or change, and those things I did want, no matter how extreme, perverse, kinky or just plain fucked up I do. Unfortunately, till 24 there was so very much that I experienced without choice that it was of little consequence doing the same or similar after. In fact, there are many things that I negatively experienced that when I had a choice I did so of my own instigation just simply take that part of my sexuality back and make it my own.

A lot of folks have asked me "how can you do X, when you experienced it under such horrific conditions." Well, except for things that cause you great physical harm, living with a fear of this or that due to something bad in your past is MUCH worse. That fear can be constant, or it might simply result in triggers where the strangest/smallest thing will find you cowering. That fear can be absolutely debilitating as well. So in that there is pretty much nothing that I can dream up that wasn't done to me in a negative light, that left me with two choices. 1. Have a zero sex life, cut myself off from ALL people, and basically hide for the rest of my days from everything...or 2. Face as many of those fears as I could, and make them my own choices instead.

Now don't misunderstand, there are a lot of things that still scare me. However, most of those things I make myself face daily (like fear of not wearing shoes, so I am constantly barefoot). Some things I can't get over so I give into them, then push the point to an extreme degree (like being naked in a home, so I try and remain nude everywhere else even as much as possible). Finally some things I can't get past (like the fear that overcomes me if I don't masturbate at least once daily), so I have turned as many of those as I can into something enjoyable instead of something ugly and full of self loathing.

Lastly, there is one thing that throughout my life that brought me physical and emotional comfort and security, though for most folks it would be rather "out there," and that I make it a point to limit myself on as much as possible in that if I simply gave into doing what puts me in that good place without any controls, then it would get out of hand. So it's my special thing for special times.

The big downside to all of it though is, simple things, basic things that would give 99% of the folks a massive thrill doesn't do anything to sexually arouse me or bring me any pleasure in any way. Yet I realize that others find me doing so arousing and enjoyable, so I instead embrace the thrill of seeing another person experiencing something positive they normally wouldn't have the courage to do.

So as odd as I'm sure it must seem to all who have seen me post here, I find pleasure in pleasing others.

In the end however, there is not much (if really anything sadly) that I haven't seen before. So I can think of nothing that I regret not doing...and as said, there is nothing I can do about that which I did.

Hush....an alias

 

not getting fucked by my ex with strap on.

 

Not staying at cousins house last chance I had

 

I've been with a few girls who loved rough rough sex. My regret is not giving that to them. They loved hair pulling, choking, being tied up, and being completely dominated. But I have a lot of respect for women and was afraid to hurt them or leave marks and afraid to be abusive but that was exactly what they wanted. I did do those things just not to the degree that they wanted.

 

I have to add there was this time me and my buddy were chilling on the couch watching some porn.

We both had our shorts at our ankles. We werent gay but we would watch each others cocks since they were the only others we each had ever seen.

Well one time we were jerking and I was hard and enjoying myself and I noticed he was soft flopping his dick around. He had said "man I bet if you touched it, it would get hard instantly". I said no way thinking it was a trick to call me gay, but looking back I wish I had touched it.

He had a very thick cock with saggy balls even when hard compared to my long skinny cock with balls that suck up inside when hard.

I would have wanted to touch it because it was different, but I did not.

 

Regrets? I've had a few. But then again...

Seriously, the one that eats at me is not having a fourseome with one of my closest friends and his wife. But you never know, if they ever bring it up again I'm just about out of excuses. I have a lot of love for both of them and it sure sounds like fun!

 

I regret not having sex with the first girlfriend I ever had. She grew into one of the most beautiful women I've ever seen. I also regret not offering sex to a mexican girl I used to work with who constantly asked me to marry her.

 

Not telling my wife sooner that i want to be underneath her while she gets plowed by a huge cock until it cums in her so I can eat her out after.