Biggest Regret?

[AZBBSLUT]

I'm turning 50 this year, which is all good, but I have had the chance to look back and although I don't have a lot of regrets there are a few times where I know I missed out on a good opportunity.  Since this is a site about bareback breeding, one of those regrets took place when I was a freshman at Drake University in Des Moines, IA.  I had only officially came out of the closet over the previous summer and I was having a good time going to the clubs (drinking age was lower then), and also going to parties.  It was at one of those parties where I got fucked for the 2nd time.  However, what happened after I got fucked (it was in the basement of the house while the party was going on), I still remember an opportunity that to this day I regret. 

 

I was upstairs, hanging out for just a few more minutes and getting ready to go, when I had several guys try to talk me into staying and going into one of the bedrooms.  They were older (30s and 40s), and they really tried HARD to get me to stay.  I was this skinny little blond twink and I think one of them knew that I had just got fucked, and one of them came right out and said, a little drunkenly, "I love to FUCK blondes!" 

 

However, this was still all way too new and I had already been told that the party would turn into a sex party and I just didn't feel like I had the nerve to do anything like that.  I had tried to slip out, but these guys were really, really persistent.  They came right out and told me how they wanted to gang-bang me and basically fuck me into the next century.  And me, in my little twink mind, just said, no way.  I got really nervous and basically just bolted out of there. 

 

One of my friends stayed and he had a friend who I didn't know so well and I heard the next week from my friend how the same guys who were trying to get me to go into one of the bedrooms took this other young kid into the room and basically raped him. My friend said they could year him yelling, screaming, telling the guys to STOP, STOP, etc., but eventually this kid just got swallowed up and per my friend there were other guys who went into the room and just took turns on this kid.

 

And it has haunted me ever since that I could have been that kid.  When I first started having the idea that maybe I missed out on something I thought it was really, really wrong to even have that kind of idea in my head.  But now, damn if I don't regret not staying.  My friend told me that when he looked in the room that the kid was on the bed, face down, and there were over 10 guys in the room and they were just taking turns - one after the other - just fucking him.  The kid wasn't passed out and my friend said that he just looked exhausted.

 

That could have been me!  Now I have certainly made up for it and although I don't keep count I'm sure I've been fucked at least a couple thousand times and I have done some of the kinkiest and wildest stuff you can imagine... but still.

 

Anyway, long story to a short question:  Do any of you have situations that you look back on and regret that you didn't take the chance or the opportunity to do something? 

Edited March 25, 2015 by AZBBSLUT

[NLbear]

There is one regret I have. When I was 16 I left home to study and was looking for a room to rent in the Big City. I knew I was gay at that time although I did not have any experience, living in a small town.

I responded to an ad for a vacant room in a house with students. I went over and looked at it. It was quite a small room, good enough though, but the rent was at the top of my budget. There were five rooms in total. The four guys living there were a bit older than me, about 19 till 22 or so, some quite goodlooking too. The weird thing was they had removed all the doors of the bedrooms. The guys said it improved their bonding as a group.

Even though I was so young and inexperienced I could sense they were gay. Just by the look of them and how they talked and acted. They urged me to take the room and they even offered to help me fixing it up and decorating it.

I was wondering what was going on at night with those open rooms. Everyone could walk in, no privacy.

At the end I chickened out. The next day I found one that was bigger, cheaper and better located. But I have always regretted, until this day, not taking that room. Always wondered what might have happened if I had lived there. Maybe being fucked every night by the older guys, introducing me to gay sex.

As I have told in other threads I found out soon enough there was a cruising park around the corner of the room I eventually rented (without knowing at the time I rented it) and was introduced to gay sex there basically every night and fucked silly, but still wondered what might have happened when I had taken that other room......

[FatFuckPigMA]

Back in the early 90s when I was in my late 20s, I met this beautiful bear named Paul.  I already had a long term partner, but we had an open relationship.  We had only three rules: no emotional involvement beyond friendship, no romantic dating, and each of us had veto rights to use when necessary.

 

My partner David broke these rules first when he become involved with young Alaskan Inuit chub chaser known by one and all "Eskimo Bob" at a Girth & Mirth meeting in Boston.  I didn't feel confident enough to use me veto power, but what is good for the goose is good for the gander, as they say, so about a month later I met a handsome bear named Paul...also at a Girth & Mirth meeting.  

 

I was crazy about him. I loved his handsome bearded face,  lush hairy body, and delicious furry ass, Even the smell of him drove me nuts.  I actually felt at the time that I was in love with him, but looking back on it with wiser sensibilities I realize I was just infatuated. Nonetheless, all I could think about was getting him naked and being his sex toy.

 

Even though I wanted to do everything Paul wanted and more, this was also the height of the AIDS epidemic and everyone was practicing safe sex, though some more than others.  Personally, I had already given up on the not swallowing thing and been barebacked by a few people outside of my relationship.  I would not call myself a barebacker (this term didn't even exist yet)  but I was certainly beginning to lean that way. So my sex life with Paul was problematic.  He didn't let me swallow, he was uncomfortable with my eating his ass though he would occasionally allow it, and he was hesitant to fuck me even rubbered up. He was so hung up I didn't even mention things like water sports and such.

 

So to my biggest sexual regret. Paul did fuck me one time.  David had long gone to bed because he had to work but Paul and I were on vacation and after Dave went to sleep we started fooling around. Finally, Paul asked to fuck me with his nice but sheathed dick.  

 

I remember he fucked me bent over the desk I had in the bedroom.  I had done it standing up only a few times...mostly bent over a toilet or some porn theater seat...so I wasn't used to the rigors of the position.  Also, Paul fucked very hard and took a long time to cum.  

 

So Paul fucked me for a fairly long time. At one point I looked down between our legs and noticed the rubber had fallen off due to the pounding.  Is said NOTHING.  I loved feeling his bare dick in my hole and I so wanted him to cum in me, but as I said he I was used to the position and Paul took a long time, so eventually my back started giving out and I asked him for a breather.  When he pulled out Paul was so freaked out that the rubber fell off (and I claimed no knowledge of this) that it ended the fucking for the night and we ended up just jerking off. To make matters worse, Paul never asked to fuck me again.

 

The situation with Paul got worse and worse and I eventuality had to stop seeing him after he used me emotionally and financially  engineered my breakup with David.  It was a very dark time for me,

 

A few years later I was  now a full fledged bareback bottom and in San Francisco on business. I went to the  Dug Out looking for cock and  I ran into one of Paul's friends who had moved to the West Coast.  He offhandedly mentioned to me that Paul was now poz and was likely already infected when we were together.  I was so turned on that I picked up this Asian chaser and convinced him to bareback me in my hotel room.  

 

Now my greatest fantasy is to have Paul use, humiliate, and poz fuck me.  I'm not overly proud of this, but it's true. It's never going to happen because it's a really bad idea, but when I am jerking off and at my horniest that's what I think about: eating that ass, drinking his piss, and taking his dirty loads.

[Guest ff-whole]

Yes, I wrote up a story about the hitchiking kid. I was once hitchiking in Australia as a 21 year old kid with a backpack and I got picked up by a gay bear and could have maybe have a blast, but I too chickened out. I started blabbing my mouth off about Australian girls and the ride was cut short.

What if... Always stayed with me.

Later there were lots of other opportunities I left sitting as well... Now I'm smarter and try to seek out these opportunities but no luck either.

[Pig Bottom]

I wish I had moved to Florida sooner.  I've been here for a little over 6 and a half years, I guess that's a long time in some aspects.   I also wish I had been wiser spending my money or holding on to it, 

 

I also regret one guy who liked me and it could have possibly turned into a boyfriend, but I didn't really give it a chance. 

 

All in all I am happy with my two dogs that I got in 2014 and if anything had changed or if I had moved to Florida earlier I may not have met them.   

Edited March 29, 2015 by Pig Bottom

[Guest]

when i was 16 an older guy started up a conversation with me at work .. asked me to meet him for a drink after work .. after work turns out the drink was in his hotel room .. nice room .. we're talking and then i feel his hand on my crotch and i was "what?" .. totally clueless .. if i had only let him do whateverthefuck he wanted to do .. 

[Guest mspchaser]

Anyway, long story to a short question:  Do any of you have situations that you look back on and regret that you didn't take the chance or the opportunity to do something? 

 

My only regret is "staying in the closet" until I was 24. I have been sexually active since I was 17, but very secretive about my sexual orientation for 7 years. Looking back, I'd like to have said "fuck you white, conservative, suburban Minneapolis... I'm gay and deserve to be proud of who I am." But as far as sexual encounters, I'm not necessarily proud of every single encounter, but I have no regrets.

[Eptxbttm]

A couple not huge ones but looking back I would do them different. First would be not accepting the fact that I love cock and getting fucked and turning down multiple guys and chickening out missing out on some great times. Second would be not starting prep sooner than later so I could help lose the fear and enjoy sex more not worrying as much about the risk. I haven't started yet but I am recovering from an unrelated surgery and will take care of that next.

[Guest]

My biggest regret is that I came of age when many bathhouses were closing in the early days of AIDS. I enjoyed lots of anonymous, promiscuous sex at baths when I was in college in Texas and when I moved out to California after graduation in the early 1980s, but by then the numbers began to decline rapidly.

[Guest]

My biggest regret as of right now I am sure there will be more but when I was 16 and was looking to take my first cock and load I put a ad up on craigslist looking to take my first cock, I had a guy that was with 3 other tops all 4 of them were poz and 1 had herpes wanted to gang bang a young bottom. This was before I became a full on dirty little kinky slut bug chaser. I didn't want to be poz then but it was 17 when I started looking and tried to get a hold of the guys again but no luck. Now all I get are fakes and flakes.

[paintedgrey]

My biggest regret involves a quick and dirty on line meet-up.  We shared no photos or anything, met up virtually blind, just 2 late 20's guys meeting up for sex.  We met, immediately he said 'er, I'm not in my 20's'.  No, he was actually in late 40's.  I went with it because I was horny.  The sex was ho-hum (he used a condom) but I didn't really get into it as I was still a bit annoyed about him lying about his age.  Afterwards, he told me I was hot and was exactly what he was looking for as he had a group of guys looking for a guy they could group fuck and would likely all want to go raw.  I felt a huge rush and a huge panic.  Was it real?  was it more lies?  I ended up spooked so never contacted him again.  I still wonder what might have happened.....

[Guest bukkakio]

My biggest regret is having been so stupid and immature throughout my late teen years. There are hundreds of "what if", from a single fuck with a hot guy. the other dude who was most likely interested in having a relationship, the gay couple looking for friends to play with...

 

Unfortunately there's nothing that can be done, I just moved on and appreciate my new level of maturity. Still, it's really incredible how stupid some young guys can be.

[Kylan]

This is a terrific question!  

Personally, though, I can't come up with any specific regrets worth reporting  (which isn't to say there weren't plenty of moments I would go back and change - they just aren't interesting enough to write down.)  Of course I have the regret that most of us have about our teens and early 20s -  that we weren't more aggressively sexual earlier.  But whenever I feel that way I also have to contend with the fact that I was in NYC then and it would have been just the wrong time (late 70s/early 80s) to be whoring around more without vastly increasing the odds that I would have been dead of AIDS by 1990.  

[Guest ff-whole]

Basically what you hear as a "regret" is the fact that you didn't know then, what you know now...

 

Everything needs time, and maturing to a state that you are comfortable wanting and doing what you do now, doesn't mean it would have felt right at that time... You wished it would have but it might, or might not be so.

 

I know for a fact that I am much more of an extreme dirty bottom and will allow a lot more then I would have or better said; liked to have in the past. Though the "regret" is that the opportunity didn't repeat itself at the moment that you do feel as you feel now.

 

If you would have let it happen then, it might have turned out great, but it could also be the total opposite and maybe turned you straight, appalled and or disgusted... What would you think of that then...?

[Guest bbbearlover1]

I do regret sublimating my Dom feelings, and questioning my desire for white male subs.  I was too wedded to the idea of who I was "supposed" to be attracted to, while ignoring desires I had since I was around 12, when I saw my first naked white male ass in my junior high school locker room.  Almost 20 years passed before I gave myself permission, finally, to embrace fully my deepest desires.  My regrets ended right after that.