Biggest Regret?

[hungryhole82]

Up until now, biggest regret i have is not to explore my sex life to the fullest when i was in city.  Currently I stuck in country area, middle of nowhere and here its very hard to find sex.  All bookstores are far away so can't go there as much as i would like to.  All gay apps are suck big time.  All chat no actions. 

[chubbybear]

Up until now, biggest regret i have is not to explore my sex life to the fullest when i was in city.  Currently I stuck in country area, middle of nowhere and here its very hard to find sex.  All bookstores are far away so can't go there as much as i would like to.  All gay apps are suck big time.  All chat no actions. 

 

I feel your pain buddy. Lived in major metropolitan areas most of my life until the economy took a shit and I had to move to a rural country area for job reasons. I live about 1-1/2 hours from the nearest bookstore but the best ones are almost 3 hours away. No where near the amount of action that I was used to in my former city life.

 

Fortunately over the last 3 years I've managed to make friends with the few openly gay singles and couples in the area and word has gotten around that I'm a kinky bottom slut who's always ready for some hot fun. I now have a few gay couples and "straight/bi" redneck type singles that have become my regular fuck buddies. If I weren't for them I'd probably move back to the city and take a job as a walmart greeter just to get back to the type of regular action I used to enjoy. Hardly anyone close to me on the gay apps and most of them are flakes who fail to show up for realtime action after we chat and agree to meet.   

[hungryhole82]

I feel your pain buddy. Lived in major metropolitan areas most of my life until the economy took a shit and I had to move to a rural country area for job reasons. I live about 1-1/2 hours from the nearest bookstore but the best ones are almost 3 hours away. No where near the amount of action that I was used to in my former city life.

 

Fortunately over the last 3 years I've managed to make friends with the few openly gay singles and couples in the area and word has gotten around that I'm a kinky bottom slut who's always ready for some hot fun. I now have a few gay couples and "straight/bi" redneck type singles that have become my regular fuck buddies. If I weren't for them I'd probably move back to the city and take a job as a walmart greeter just to get back to the type of regular action I used to enjoy. Hardly anyone close to me on the gay apps and most of them are flakes who fail to show up for realtime action after we chat and agree to meet.   

I really want to get the fuck out of this hellhole called Southwest VA.  Everything is so far away.  Sex has become huge part of my life and like you said in small town you have to be careful, make sure words don't get around that you are slut.  It's funny that all those homos looking for sex online everyday and have nerve to tell other guys that they are slut.  There is nothing like having bookstores, bathhouse, sauna close by so we can frequent as much as possible.  Before I started going to bookstores, I used to go months without having sex. 

[Guest]

Based on what I know now: being a Condom Nazi, through the 1990's, which I consider, the period, where I was the most sexually active with other men. I feel if I had the 'Anything goes" approach, to gay sex, like I have now, It would have been a much more enjoyable time. 

[Bibttmmiami]

One time when I was still dating my wife I was bored and horny and I was surfing manhunt while I talked to her. A guy messaged me that he wanted me to come over to his condo wearing just a towel so he could fuck me at the pool. It was late at night. I asked about condoms and he said no. where would I put them in my towel? It would be bb. I asked my girlfriend what she thought. She told me to do it. When I asked if she was sure her response was “do I sound like I’m asking? Do it.” When I messaged the guy back he was already offline. Maybe 15-30 mins passed from when he first messaged me. Always regretted not messaging back sooner. It would have been so hot to get fucked in the open like that and be totally vulnerable by not having any clothes. 

[Bibttmmiami]

My 2nd biggest regret happen after the first time I swallowed cum. My first time swallowing was actually in a ABS booth. I met a guy online and we decided to hook up at a local ABS. We got a booth and he had me take off my shirt and pants. Then he turned me around and shoved me face/cock first against the booth wall and ate my ass. Then he turned me back around and stroked my cock and sucked it for a few minutes while he fingered my ass. Then he dropped his pants, pushed me down to my knees and had me suck him. He grabbed the back of my head and started face fucking me even making me deep throat him until I’d gag on his cock. He told me to finger his ass while I sucked him. I did. A few minutes later he asked if he could cum in my mouth. I said, mmmhmmm and nodded my head. Next thing I know he’s filling my mouth full of cum. I swallowed every drop. Then I made sure to clean his cock and get any cum that was left. Then he pulled up his pants and when I asked. “What about me?” He said, “I don’t have time.” Then he left the booth with me nearly naked on my knees. I felt so used and slutty. I loved it! When I got dressed and left the booth there were a couple of guys rubbing their crotches, but itwas my first time and I was scared so I didn’t hang around. 
 

I wish I had just licked my lips, gone back into the booth, stripped and sucked off anyone who wanted to use my mouth. And if someone had wanted to “force” me to take their cock in my ass well, I guess I’d have had to be a slut and let them. The thought of being able to go home to my wife knowing I had multiple loads of cum in my belly and or ass and I missed out on it is a big regret. 

[Guest WelshBBCigarFuck]

I was sent up to Manchester for a training course, had to catch the train up from South Wales actually on my 21st birthday. It was a week long, staying in what was the Ramada on Portland Street, with the training course in a building across the road.

My biggest regret was not having the nerve to ask someone where the gay village was, since Queer as Folk was on TV back then and I wondered where it was. It turns out the gay village was about a 2 minute walk from the hotel and I have kicked myself ever since as I would have been fresh meat for breeding.

Years later and I have been back to Manchester so many times it’s almost a second home. Also had lots and lots of bareback sex up there, but still need to find a well hung top to breed me senseless during a visit.

Edited October 18, 2021 by WelshBBCigarFuck

[Tanbbottom]

I had moved to Vancouver for a work/study term. I was looking for shared accommodations to make my small stipend stretch as far as it could. The ad which caught my attention the most said it was a household of male nudists looking for the same. I was a wannabe nudist but when I made the call I was way too nervous. The guy picked that up, but even if he had offered I regret I would not have followed through. 

Second biggest regret was buying a message from a male nude masseur at a silent auction. He was late answering his door when I arrived and the guy that left as I was let in had clearly been freshly fucked. I so wanted to ask for the same happy ending but was too shy. He may not have been up for fucking me so soon after the other guy but probably would have sucked me off if I had rolled over with a big boner. I was just way to much in my head and imagining rejection to take a chance. 

Thankfully I have learned from these regrets; spend as much time naked as I can and am far better at imagining success and landing loads up my ass. 

[Breedthisslut]

My biggest regrets: 

Getting married at age 20. I definitely should have played around and I might have realized that I liked cock more than pussy.

Not trying a cock not my own until age 38. It was another 15 years or so that I accepted that I am gay.

My last biggest regret was with a guy that I hooked up with who treated me exactly how I wanted to be treated once I realized I was gay and after 8 or so times with him, I came to realize that he was Poz UD. He wanted me to be what I wanted to be, but my pausing to his revelation saw my chance with him to slip away. 😢😢😢

[Guest]

I wish I had not waited until in my 40s to try cock.

[YourNoLimitsBottom]

My big regret echoes others: denying my desires as long as I did. Now it's a matter of making up for the lost time.

[boy4you]

Wish I lived my whole life in NYC instead of western Nebraska. 

[BlindRawFucker1]

For my entire life, I have suffered from the condition called cowardice.

 

I knew from the age of around seven, that I was “different.”  I discovered at that age I absolutely loved the scents of boys.  By twelve, I knew I was gay.

 

Being blind, I couldn’t see the other boys in the lockerroom.  But, they couldn’t see me either.  But, I loved the scents.

 

I wanted to explore those scents up close and more personally, along with touching to see what they had and to taste them and their cum—I loved the taste of mine.

 

During junior and senior high, I had four extremely overt opportunities to do what I wanted, and more.  But, that cowardice took over.

 

I didn’t go to college, another missed opportunity.  However, in the mid ‘80s, I may have contracted HIV and be dead now, which might not have been an entirely bad thing.

 

Finally, in my late ‘20s, I had my first sexual experience with a much older man.  I doubt it could have been any better.

 

I had my first bareback experience about ten years after that—I topped—and my first bottom BB fuck a couple of years later.

 

So in short, I wish I had played with those other teenaged boys in school.  I definitely wish I had experienced bareback fucking from the first, no matter the consequences.

 

Unfortunately, I am still somewhat a coward.  I hope that I’ll take advantage of any offer to fuck BB from any guy who I feel the least bit attracted.  I can only hope that he comes along.

 

Sorry for the long, rambling answer.

[alwaysready]

biggest? the two great loves of my life...while i was a good boy.   how to choose? not having sex with ethan wolf? not finding x or molly, living in an erotophobic city, getting older. gee, one could run on and on.  i often do. lol

[alwaysready]

boy4you, i know how it feels in retrospect. but i think those years, however fallow they may have been, helped you mature to the point where you could move to nyc and, i think i remember correctly, you have had a pretty damn fine time since the start. i did not come out til i was 25, same year i started smoking weed.  i am glad it took that long, though there were opportunities i bitterly admit i missed. however, they make for great fictional material in my 5 volume novel, laboriously under construction.