What is your biggest sexual regret, and why?

[MissBlondie]

Can you share when you DID start

In retrospect around a year later than I could have

 

[carlsnake]

I regret not having sex with my wife before we were married. We dated nearly eight years, high school through college. I did not screw her because I didn't want to run the risk of getting her pregnant. I found out after we were married that her other dates in college were fucking her on every date. She was on the pill. One night, when I had her naked in the car, she lay back, spread her legs, opened herself and said, "I want you inside me." I didn't do it.
Our sex life has been great throughout our married life, but I wish I hadn't suffered so long before finally doing it. She says she's glad we didn't.

 

[Inspire8]

*****

 

[blubyuf6]

........

 

[Locknuts]

I suppose my biggest regret is not being faithful to my wife over the years.
We married when she had just turned sixteen and I was seventeen and we were so in love. Of course she was pregnant when we married. She had our son during her eleventh grade in school. Our history teacher tutored her at home. She went back to school her senior year and graduated Valedictorian. Went to beauticians school and my Mom babysat while she was doing that. Her Mom worked at the school office. I had a job at a local plant. Then I worked at the State job for three years and then went to work on the railroad.
Of course that meant staying over at the other end and soon I was seeing some very young women just to pass the time. Didn't fall in love with any of them. Didn't want to. I guess you could say I just used them and there were several over the years. I enjoyed my young life and my wife gave me all the rope I needed but never had any children outside our home. We do have four children. She ran a beauty shop in our home for several years and closed it down when I had to go out of town quite a long ways away to work and she went with me. We were gone for seven years and then a railroad job opened up back home and we came back. I retired five years later. I've been retired fourteen years now. We have been married for fifty nine years and it has been because of the good woman she has always been. She never stepped out of line as far as I know and if she did it would have been because she needed too. We still love each other dearly but I don't have to tell you how hard goin it was in the early years. It was not easy for her and I know that!

 

[bill3901]

I was thinking about this today and my biggest regret is not exploring more with a girlfriend I had when I was in my 20s. She was the most uninhibited and sexiest woman I ever met and its a shame we didnt explore some kinks that she definitely wanted to explore and that I was not ready for

 

[darkknight01]

I was thinking about this today and my biggest regret is not exploring more with a girlfriend I had when I was in my 20s. She was the most uninhibited and sexiest woman I ever met and its a shame we didnt explore some kinks that she definitely wanted to explore and that I was not ready for

What were some of those kinks?

 

[bill3901]

What were some of those kinks?

you name it, nothing too outrageous (for this site anyway)...but she definitely was pushing me into sharing and such...also, a little pee play...which excited me then but I was much too sexually shy to really explore...

 

[Mikeawh]

My biggest regret

When I was in high school there was a girl that had a crush on me the entire time but she was that girl in school that had a new boyfriend every week and would let them fuck her brains out on first dates, not having the self-confidence I do now I didn't want to be labeled as one of those guys, so I never went out with her.

About a year ago I seen her again she looks amazing, so hot! She's tall, long legs with a tight little ass, nice big C cup, beautiful big lips long red hair .

it turns out she married a friend of a friend, neither of them knew her in high school. Not long after my friend started telling me stories about them, about having threesomes with other guys and girls, strap on sex, orgies, role-playing, anal.....all that stuff we wish our wives would do she does it!

I don't necessarily regret where I am in life, but it sure makes a guy wonder if he made a mistake

 

[LeeFL]

Swingers

I met a lady who was 50 and I was 30; she was taking me out to events in the swinging world but it never really clicked for me.
I wish I had pursued it and lived out some of my sexual fantasies before I had settled down to commit.

 

[bobsknickers]

With a guy

Looking back I see that it was a definite 'What if..' moment.

At the time I was dating a girl who was a dancer in productions like seaside summer shows and the like. We were sleeping together and I went to see her one weekend. The place she was staying at a fairly strict landlady so we were not permitted to share a bed.

Other members of the theatre group were staying in the same place and I had to share a room with the leading male dancer. I new he was not hetro but I was told that wouldn't be a problem.

IN the night I was having a fantastic dream where my g/f was sitting on top of me and moved her knickers to one side and we were having a fantastic screw. As I got closer and closer to finishing, I woke up and discovered that the guy I was sharing a room with was sucking me off!

I froze and to be fair I was a little scared. I asked him to stop (. in fact my cock had shrivelled) and he pleaded with me to let him carry on but I said no, which he did.

I know that he must have been close because I know at the time I was but I never did get back to my dream, but I do wonder now what would have happened if I had let him carry on. I look back now and wish I'd let him he'd finished me off and then, of course would I have been asked to do the same to him...

So, that's my regret becasue as I get older I have become more curious

That

 

[lilsarah91]

taking the job at the adult store. the money was great and I had a lot of fun but the drama wasn't worth it

 

[panty_aussie]

I think turning down chicks who were 18 or so when was younger

I wonder why I didn't fuck them since I knew they gave out sex and headjobs like to a every guy

Not fucking Next neighbour chick who caught me mas and not fuck ing ccousin why had a chance

 

[HoldYouDown]

A couple that wanted me to join in, but I chickened out. I think I met them on Lit and they lived in Queens.

 

[SgtSpiderMan]

A couple that wanted me to join in, but I chickened out. I think I met them on Lit and they lived in Queens.

Be honest. You just didn't want to head to the outer boroughs.

 

[crem]

my biggest regret is not fucking my sister when I had the chance... a lot of touching and grabbing each other but I didn't follow thru.... she doesn't seem to want to fool around again.... but I'm still gonna let her know that she is so hot so I can try to get in her pants.... she knows I want her so bad

 

[HoldYouDown]

Be honest. You just didn't want to head to the outer boroughs.

Lol well yes, it IS a schlep.

 

[RawHumor]

taking the job at the adult store. the money was great and I had a lot of fun but the drama wasn't worth it

Drama at an adult book store? That seems... unexpected.

 

[steamboat610]

Wishing I gone through with the mmf threesome my ex had planned that would've been him fucking me, while I fucked her, instead of me thinking she wanted more dick and being jealous