My first time with Jack

Not sure how to start this.I want to tell the true story of how I spent my first night with a guy…a guy I met in a hotel bar. I had never been with another guy in my adult life. I am a healthy, middle aged guy who works out all the time, is reasonably good looking, and has a strong sex drive. I have been married and have children but now I am single and have been for five years.
This story begins I guess with a relationship I had with a girlfriend from long ago who had a particular fondness for anal sex. She would come time after time always wanting me to hold off coming as long as I could. Back then we didn’t have drugs like viagra, so I had to do everything I could to keep from coming inside her ass, which was so soft inside. She knew how to contract on my dick and would ride me while I was deep inside her. While it felt great for me, she was over the top with ectasy and would typically come more than once as I thrusted my cock inside her. I always wondered how she came without me stimulating her clit. It lead me to experiment with my own anus when I was alone.
First, I must tell you that she really enjoyed douching herself before we had anal intercourse. Once she was clean she would ask me to watch and she would fill her anus with hot water with a hose attached to the shower and would let out deep moans as she let the water rush from her backside.
So, one time when I was alone, not dating anyone, and feeling really horny I decided to try douching myself and seeing if I could fit a cucumber I had into my ass. I had a shower pic that allowed me to fill my anus with hot water and though I was a little grossed out at first, I kept at it and got myself completely clean. I greased up that cucumber with some vasilene and began to try and insert it into my ass. It took a while but I finally got the huge ten incher inside me. I was on my back, legs spread, and began to ride up and down on it, going faster and deeper with each thrust. It felt unbelievable. I started to stroke my very hard seven inch throbbing cock and had one of the most amazing orgasims ever…it lasted for a couple of minutes as I kept slowly humping it, pretending I had a huge cock inside me.
That was just the beginning of my anal fixation. I never thought I was gay or anything but I began to fantasize having an affair with a guy. I have dated women all my life and always will but I started to imagine what it might be having sex with another guy. When I was out of town I would go to adult stores and go into video booths that showed both straight and gay videos. I would get so hard watching two guys fuck and suck each other that I would search the dildo section for a big 10” hard cock that I could take home and fuck myself with. I admit that I did not ever want to be caught with it which was why I always waited until I was on an out of town trip. It got so that every time I went away, if there was an opportunity, I would spend hours fucking myself.
Lately I have taken my fixation to another level. I joined an online dating service that included a gay section. You could post pictures and videos of yourself on the site and try to find a match. I listed myself as a bi-sexual guy looking for another like minded male. I knew in my mind what I was looking for. I began to take pictures and videos of myself naked and riding a big dildo. I am not very hairy, have great legs and a pretty nice body so I got a lot comments and emails from guys wanting to hook up.