Regrets?

[curtdude]

not taking advantage of opportunities that were presented to me and just going for it:
Peter staring at me while we rode the elevator at school looking at the bulge in his pants and he looking at mine
Joe in the bathroom in a towel telling him I wanted to shower with him he said ok and I chickened out .
Mike : with his nice long cock poking out the leg of his shorts and not reachin out to touch it
James sharing a tent with him and seeing his rock hard erection poking out the fly of his boxers and not sucking the hell out of it
missed opportunities

 

[techpump]

This is hard to admit.

I regret not fucking all the girls that wanted me really bad in college. It was like over 20 girls in 2 years. Well actually there were like 6 or so the first two years before I transferred. They had the greatest tits too. Cute girls all of them. They were all there before I met my wife. I love that my wife and I were both virgins when we started dating because we wound up having some very acrobatic, wild, hot, super wet sex with each other daily, sometimes more than once a day, month after month for years and years. But damn, all that other pussy, I kinda wished I had experienced it all, as a man, I feel like I missed out on a part of life.

I regret not fucking a few of my girl friends too. I kinda wanted to date them, but they wanted me really bad, more than I wanted them. They actually hated on my wife when I started dating her, because they wanted to date me, and I never did. Super jealous girls. I always wanted to know if they were good fucks or not. I would guess they probably weren't. But I wish I had known.

There were a few times when I feel like I could've had sex with some very close female friends of mine, older and younger than me. One I'm sure has had a crush on me for over 20 years, well it was stronger the first couple years, by now its probably not there, but recently she admitted to me that she's really good at giving blowjobs, so there's that. She's like 18 years older than me but alluring and sexy as hell. My younger friend I felt like the sparks were there when we first started hanging out. She's very touchy and handsy when talking and laughing and especially drinking. I gave her a weed oil pill one day and it took her days to take it but when she did she texted me in the evening that she was doing great. Then around 11pm she texted me freaking out that she was kind of losing it and needed some support maybe. I almost got out of bed and raced over to her place (I was staying at a friend's house out of town for nights on end every week while I was in grad school). I wrote her some calming things and I thought it worked. The next day in class she was like "I thought you were gonna come over, I really needed some company last night I was out of sorts and freaking out!" Well, my "I'm married" radar was going off like crazy and my friend, who is 13 years younger than me, is too hot to be around if something like that is going on. This happened back in 2015 or 2016. Just a year or so ago I was hanging with her and we brought that weed oil incident up, and she very matter of factly said "you should've come over that night" and I feel like I had the one and only chance to hook up with her. I feel like it was certain it would've happened, and I'm glad I didn't go because she's my very best friend in the whole world and we've cried and laughed and shared so much with each other, but the one thing about it is that I would love to know how great of a fuck she is. I know she's wild. We've talked about sex here and there, and she's hinted at some things that for sure let me know she's a keeper in the sack. I wish I didn't regret this, but there it is. I'm a man with a raging libido and there are parts of my brain I cannot shut off or say "don't do that" to no matter how hard I try.

 

[chrissal480]

I don’t think I have anything to regret.. pretty much done what I like doing and what curious about trying.. and done it with several guys over the years.. other than fisting I’ve pretty much done it all but fisting

 

[User101823]

I have a list of “missed connections” from over the years…I regret not being more active in pursuing them in the moment.

 

[latinluva]

Thankfully no regrets, I had many male and about twenty female lovers before the age of 29. I do miss the touch of a masculine man, but I'm grateful for what I have in my Wife and our life together. She keeps things kinky and exciting for me.

 

[hzs3fg]

Thankfully no regrets, I had many male and about twenty female lovers before the age of 29. I do miss the touch of a masculine man, but I'm grateful for what I have in my Wife and our life together. She keeps things kinky and exciting for me.

You're a lucky guy!

 

[lapdog2001]

most of my regrets were from before 25, not taking opportunities when presented with them, i bought into all the bullshit about how friends don't have sex, casual sex was bad blah blah blah. Hind sight being 20/20 i missed a lot of opportunities, i had a lot of very attractive close female friends and years later some even brought up our friendships and questioned why i never made a move when i could have and said they'd have gone along with it.

I regret that I spent too much time thinking and not enough time doing.

I regret all the times I've been given signs from a woman that I could have sex with her but was too oblivious to realize it until it was too late.

I've certainly missed signs that women were into me. I'm married now and my wife had a much better idea of who her competition were than I ever did.

All of the above!
Not having enough confidence to at least ask many of the wonderful women I met when I was in my late teens (18+) and early 20s.

But who knows how things would have been different? Had I been more aware and ended up married to someone else how would she compare with my wife? Everyone is different and we can often never be sure if the road we didn't take would have worked out better or worse.

This too! Had I made moves on the women of my past who were friends, friends of friends, co-workers and acquaintances, would I have ended up with the woman who is now my wife? Would I have entered into a marriage that didn't last?

All the 'what ifs?' and 'who knows?' will go unanswered and there is absolutely nothing we can do about them anyway, so I really don't think about it very often.

 

[zaratoga]

Back in 80s, homophobia was rampant as was the stigma of AIDS. So never explored my male curiosity side. Want to try sucking dick, even asked two of my closest friends, but they politely turned me down, too straight really, the whole “if you were a girl, we’d be married” bit. My self, happily married to a woman with 2 wonderful kids, but spouse not interested in sex. I married the first girl I had a long term relationship with. She had multiple relationships so feels sex isn’t that important. Well, she got the good catch. I was too young to know how to speak up for myself, always putting other people’s needs before my own, then resenting that I didn’t get what I want when I asked, at least that way my perception. Now at 50, the past few years have been truly enlightening as I stumbled onto the spiritual path. So I am better now, following Buddhism principles. But it is hard to let go of the craving for sucking a dick… I say to myself if I can just do it once, to some hot young guy I fantasized about in the past, the jock who just needed some help to get off, I think I could be a lot more satisfied. Truly something off the bucket list. I dunno… missed chances, window is closing. Regret….

You're near Boston... Grindr or a sauna are options!

...
My regrets are not picking up on cues during my adolescence with a couple of classmates...but I don't want to get in trouble with the moderation team. So that's all I can say.

 

[cockyjosh]

Regrets, I've had a few...

I regret that I've never sucked a cock and, at this point, most likely never will.

I regret that over many years of marriage, I have grown sexually and embraced my kinky side, but my wife has done neither.

What are your regrets?

I feel you here. This is exactly me.

I’ve always been interested in cocks as far back as I can remember, but I have never sucked one.

Same with growing sexually. Maybe it has to do with my other regret, but I would like to expand what my wife and I do in the bedroom. I know she is somewhat bored with what we do, but would feel like expanding things would be too far.

 

[bigbucky]

of course, there are the gals that I never fucked for one reason or another.

 

[notthatguy]

Sexual regrets..very few.

Other regrets.... lots.

Never heard of a man on his death bed say "I wish I had less sex in my life".

 

[ChristmasGoofy]

Regret may be somewhat too strong of a word, but I wish I was a bit more forward in the romance/sex department in college. I was super strait laced and cared about getting good grades, but I had several opportunities to be more adventurous that never panned out. From as big as having a boyfriend to as small as seeing my roommate’s cock in the showers, I was always too modest and academics-focused to have that kind of fun in college.