A Change In Direction

A couple decades ago I turned 40. I was divorced and yet another post marital dating relationship ended. I was lonely and uncertain. I was having no luck with the ladies and my repressed gay desires flooded my head more and more.

I had a month's vacation coming up. Suddenly I had an impulsive idea. What if I went to another city where no one knew me and experimented with the gay lifestyle. I soon made the plans, got in my car and drove a few hours to get there. I got a short term monthly rental in a furnished apartment hotel. I went out for dinner and got my bearings. The next day I bought some stylish form fitting clothes, skimpy briefs and nice cologne. Not knowing what I was doing I went to my first gay bar. I was nervous and excited and lots of men especially older ones made passes at me the dark. You could smoke un those days in a bar and I sucked on the filter of my cigarette wondering if there would be something in my mouth by the end of the night. The men hitting on me were either aggressive,desperate,married or too sleazy looking so I was beginning to think maybe this was not a great idea. Then this soft spoken older guy,white haired in his 60's moved into a spot beside me at the bar. His name wasxRon
He spoke calmly and had lots of normal interests. He was the first man I had a real nice real conversation with. I asked him back to my hotel and he readily accepted. I could feel my gay desires churn within me. When we got there and sipped some brandy I had,I told him I had never been with a man. He smiled and said it was like riding a bike once you learn it is automatic and he would teach me. He first started kissing me and I enjoyed that a lot. Later in bed he explored all of my naked slim body with his hands and mouth making sure he pleasured my cock until it erupted in his mouth. God he was good at it. I returned the favor and fully enjoyed sucking him. He was right. It became second nature after a few minutes. Loved the sweet taste of him when he let go. He spent the night with me and left his number in the morning.

I called him and we had a long phone conversation a few days later. He said he missed me already and suggested that instead of going to the gay bars he picks me up and takes me to dinner. That scared me a bit as I sensed his need for more than sex. However I threw off my reservations and he picked me up. At dinner I noticed myself thinking about him and lots of little things I noticed. He had a nice smile and laugh. He was a big boned man and when we were in bed his body had felt manly and fun to explore even though he was so much older. His cock turned me on. He had big balls and it was a bit longer and thicker than mine and circumcised which I liked the look of more than uncut. Horny thoughts rushed through my brain as I was

aware this was my first real date with a man.

He drove me back to his place and I spent most of the weekend in one of his bathrobes and in and out of his bed doing foreplay and oral on each other. The next few weeks were a blur going on dates with Ron and sex in mostly his bed sometimes in his car when we parked somewhere. By this point I was happily receiving anal from him and like riding a bike I was riding his cock in different positions as if I had been doing it for years. It no longer hurt at all and I experienced pleasure like I had never known.

The month was coming to a close and Ron had something big to ask me. He dropped the bomb one night. Move in with he said and you can work for in my RV sales business. I was in sales he knew that. I told him this was a crazy big step and I needed time to think. He said okay. I went home and fir several weeks wrestled with it. I missed him and the sex. Then one night it became clear to me. I had never felt so good with someone so compatible. I decided to give it a go. I packed up and called him. He was excited on the phone and I drove to his house that night. We had almost 15 great years together before kidney disease took him. At the funeral one of his younger friends consoled me. Jake was 5 years older than me and we became close . Nature took its course and we became lovers.He is a chubby man and we are both tetired now. The sex is much different with him but very satisfying. He likes long kissing sessions cuddling then oral. He toys me with a dildo then I do him. I have gained a fair bit of weight since knowing him with all the big meals he cooks for me. I am almost as chubby as him now and I guess you would call us chubby chasers.

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Anonymous

by Anonymous on Jun 11, 2025 at 7:13 AM

I am very in to sex toys and for years I have used them often. I have a very large collection and they range from small to fairly large.
For years I thought about having a friend that would enjoy using toys on me and I finally have a friend that enjoys that. On Saturdays he comes to my house and most of the weekend he and I are naked with my toys all over the house where he can use them on me as he wishes. I really like being naked with my ass exposed to him so that he can use my ass and shove toys up my ass fuck me with them and he really enjoys making me take the bigger toys and he always jacks off on my ass and on occasions he does fuck me with his long fat cock. Most of the time he likes to pull out and shoot his big thick load on my asshole but sometimes he will get balks deep in my ass and he always tells me he is going to cum in my ass and I really get excited when he is fucking my ass really hard and deep and starts telling me he is going to cum in my ass.
He gets excited if I start begging him to cum in my ass. Almost every weekend I am his anal slut and sex toy and it feels so good I look forward to his visits and we have been experimenting with fisting. His hands are large so I have not been able to get his hand up inside of me yet but we keep working on it and we are getting very close to doing it.
My anal fetish has been a big part of my life for many years and it never gets old or boring. I feels so good and having a buddy to play with my ass just makes it that much better.

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