Regrets

[BiDomMike]

Certainly a way to go. I might be brave. Who knows. Here for a good time not a long time. (A lunchtime wank is definitely on the cards after these chats)

Well this thread is about regres and you have a fun way to try to not have a regret ... she'll either rise to the suggestion or tell you not to even think about it ... at least you'll know - or perhaps she'll stay quiet, and think it over ... even better

[SUBBI]

In a nutshell! Thanks Mike

[BrokenQuill]

Thnaks for your openness on this Mike. I think that we all have times when we feel that we could perhaps have done a little more.

My own regret was way back when I was first realising that I wasnt quite as traight as I thought I was. I had been through a really tough break-up and had lost not only my partner, but I was on the ay to losing my home and job at the time too. The toll of the break-up impacted my ability to pay my way and also my mental health which was a concern for my employer. So they sacked me, which compounded onto my financial stresses.

I was lucky enough to move into a friends home and lodge there for a while, until I could find something more permanent. Meanwhile an ex-colleague and friend of mine strived to keep in touch. He knew both me and my ex-partner and was concerned that I would continue to travel in a downward spiral. On oe particular evening he took me out for a few beers so that I could get things off my chest. I have to mention at this point that my friend and ex-colleague was gay and I knew that he held a special place for me in his affections.

After a long and probably boring night talking things over, he gave me a lift back home, diverting to a quiet layby along the way as I needed to relieve myself. On my return to the car he repeated that he had feelings for me and I decided to let him take control of the situation. We kissed for a while befroe he ended up giving me the most amazing blowjob. I then tried to reciprocate, and managed to start off quite well. He had the most beautiful cock and I was more than happy to stroke it and then take it into my mouth. Unfortunately despite my intentions, I didtnt get to the point of arousing him enough for him to cum in my mouth as we were interrupted by a group of people passing nearby.

We hastily compsed ourselves and he drove me home. My regret is that I didnt have the confidence to invite him into my lodgings. I had invited him around on several occasions before, so I knew that my housemates knew of him and wouldnt have been too surprised if he had come in with me. In addition I had a double bed in a private room that we could have made use of. But I didnt ask him in.

Shortly after this event, I relocated to live with my family and started on the long road to recovering my mental health and got back into employment. Much mo my additiohal regret, I also lost touch with my ex-colleague friend, and only really reconnected with him several years later. By that time we had both moved on and the dynamic had changed considerably.

I still think about that night and what could have been. I was probably not ready to engage in a full-time male on male relationship, but we could have had so much more if I had only been confident to ask him in for a coffee...

Andy

[BiDomMike]

Thnaks for your openness on this Mike. I think that we all have times when we feel that we could perhaps have done a little more.

My own regret was way back when I was first realising that I wasnt quite as traight as I thought I was. I had been through a really tough break-up and had lost not only my partner, but I was on the ay to losing my home and job at the time too. The toll of the break-up impacted my ability to pay my way and also my mental health which was a concern for my employer. So they sacked me, which compounded onto my financial stresses.

I was lucky enough to move into a friends home and lodge there for a while, until I could find something more permanent. Meanwhile an ex-colleague and friend of mine strived to keep in touch. He knew both me and my ex-partner and was concerned that I would continue to travel in a downward spiral. On oe particular evening he took me out for a few beers so that I could get things off my chest. I have to mention at this point that my friend and ex-colleague was gay and I knew that he held a special place for me in his affections.

After a long and probably boring night talking things over, he gave me a lift back home, diverting to a quiet layby along the way as I needed to relieve myself. On my return to the car he repeated that he had feelings for me and I decided to let him take control of the situation. We kissed for a while befroe he ended up giving me the most amazing blowjob. I then tried to reciprocate, and managed to start off quite well. He had the most beautiful cock and I was more than happy to stroke it and then take it into my mouth. Unfortunately despite my intentions, I didtnt get to the point of arousing him enough for him to cum in my mouth as we were interrupted by a group of people passing nearby.

We hastily compsed ourselves and he drove me home. My regret is that I didnt have the confidence to invite him into my lodgings. I had invited him around on several occasions before, so I knew that my housemates knew of him and wouldnt have been too surprised if he had come in with me. In addition I had a double bed in a private room that we could have made use of. But I didnt ask him in.

Shortly after this event, I relocated to live with my family and started on the long road to recovering my mental health and got back into employment. Much mo my additiohal regret, I also lost touch with my ex-colleague friend, and only really reconnected with him several years later. By that time we had both moved on and the dynamic had changed considerably.

I still think about that night and what could have been. I was probably not ready to engage in a full-time male on male relationship, but we could have had so much more if I had only been confident to ask him in for a coffee...

Andy

Thanks for sharing Andy and I hope that your recovery to full health has continued. It's definitely the kind of 'regret' that I was thinking about when I thought of the thread. It's just the not knowing isn't it?

[Don Williams]

Oh, the risk there! No idea how that would play out! On the one hand, we have a strap-on so I suspect she suspects something. On the other, God alone knows

Risk, indeed. Some wives are al about it, in fantasy, but brutal, when things get real.

[PFWilly]

Interesting thread!

My main regret is that I didn’t let my buddy fuck me when I was in my 20’s. Looking back I see that was a mistake, I just didn’t think that his huge dick would fit in my ass. Many years, and many videos, later I know he could have done it. It sure fit in my mouth. Still never been fucked, but sure think about it a lot. LOL

[BiDomMike]

Interesting thread!

My main regret is that I didn’t let my buddy fuck me when I was in my 20’s. Looking back I see that was a mistake, I just didn’t think that his huge dick would fit in my ass. Many years, and many videos, later I know he could have done it. It sure fit in my mouth. Still never been fucked, but sure think about it a lot. LOL

So it's been in your mouth at least?

[PeterWatson]

All these videos and stories where a guy with a virgin ass takes a big cock in on the first try, I wonder about. I know the idea if I get horney enough and if he takes it slow enough, it will hurt for a while and then it will feel great. Maybe I am skiptical, but I have my doubts. I have felt the pain of having something pushed into my ass and that pain can quickly drain any sexual excitement that I felt before penetration started. I have had one cock in that hurt like hell and a probe used for taking prostate samples for biopsy. Both hurt alot and for me, pain and sexual pleasure don't go hand in hand.

Think of someone asking you to do the splits and pushing you down when you went as far as you could without pain. It would feel like your inner thighs were going to tear and they actually might. I think the way to get penetrated and enjoy it will be to work up to something the size of a cock over time, using fingers, dildos, or whatever and gradually stretch your ass till it can comfortably take the cock you want to entertain. The use of poppers will help if you can get them. Working up to penetration can be part of the fun of making a new friend and building up together. Until penetration is possible, there is always a pair of hands and a hot mouth to finish the job until the ass is ready to take its place in your sex life.

I would like to meet a friend who is local who would like to undertake that journey with me. Someone with my taste in porn, can host, and wants to take it slow and safe. Someone who is drug and disease free, does not smoke, and tastes good. Well, that is the fantasy. Fantasies will have to do for now.

[PFWilly]

Interesting thread!

My main regret is that I didn’t let my buddy fuck me when I was in my 20’s. Looking back I see that was a mistake, I just didn’t think that his huge dick would fit in my ass. Many years, and many videos, later I know he could have done it. It sure fit in my mouth. Still never been fucked, but sure think about it a lot. LOL

So it's been in your mouth at least?

In my mouth on many occasions, loved sucking his cock to get a hot load to swallow.

He had a quick recovery time that I enjoyed. My wife enjoyed his fast recovery on one particular night. lol

[Jimfix44]

Good tale. Made me hard