franklyhorny said:
How did you first time happen and where were you when you did it?
If you don't mind an additional reply:
First time circumstances were probably as weird as it will sound.
I was having an affair with a married lady. After the second or third time we met up, she told me that her husband was aware and approved from the start.
I also found out he was VERY cuckold, and had watched her fuck many other men. Over time, he became very bi and was having sex with as many men as he could hook up with.
And, he now wanted to join us on our next get-together. Long story short, he was much more interested in having sex with me than he was just watching us.
I was in my mid-40's, had never had gay or bi sex, but was curious, so we set a date to meet.
The first night they arrived, I met them at their hotel room. They were already naked and had my clothes off in just a minute, and he immediately started sucking my cock. When I got hard, he wanted me to fuck him in the ass. His wife was wearing a strap on, and she fucked him a bit to loosen him up, them she fucked my ass to keep my cock hard!
I got behind him, and was working on penetrating his ass. When I finally popped in, he started crying for me to take it out. I'm not that big, but do have some thickness, so I was surprised that he couldn't take it. Both his wife and myself were telling him to relax and assure him he could take it, but he finally had to squirm away from me.
I went to their hotel the next morning, and got to fuck the wife right away. She was riding me reverse cowgirl, and he walked to the head of the bead where I was, and put his cock in my face. I had always wondered what it would be like to actually suck a cock, so I was ready, and I took him in my mouth.
Since it was a first time, it's not like I "knew" what to do, but I tried my best. Strong suction, using tongue, bobbing my head back and forth, and lots of enthusiasm! And I enjoyed it very much and even wondered if I had been missing out on something all my life.
For the next couple of days, it was very much like sex with his wife, then sex with him, wife, him......