John was my very first gay lover. I wrote a story about our first time together you can find on my page titled ‘Big John’. To briefly recap, I was a 50-year-old, recently divorced man in Florida who decided to explore my life long repressed gay side and met 63-year-old John through a ‘silver foxes’ gay dating web site. He had a similar back story and had never had gay sex before either. We had been lovers for 3 years when I had to move back to California to settle an estate. John was also going to move back to Pennsylvania to be closer to his kids. We had a wonderful 3 years of incredible sex, and we both learned so much starting out as gay virgins and exploring our mutual sexuality and sensuality.

During those 3 years I also went to bed with several other men, but John was always the first and very special to me. He knew I was sleeping with other guys, and I never tried to cover it up. My kink was I liked to be the woman in bed, and I got very good at it. At the end of 3 years, my cross-dressing skills became highly refined, and I had a pretty impressive wardrobe of gowns, lingerie, and wigs. I could also put on make-up like a pro, had a Lady Shick Electric Razor, quite a collection of skin moisturizers, and had a sissy side that even surprised me once I heated up!

I also stumbled across a niche market in Florida. I found a plethora of men older than I that were either widowed, divorced, or had wives that were not into having sex anymore. This was a generation of men who definitely felt more comfortable being closeted. Somehow me taking the feminine role in bed made them feel less gay. A few even brought that up. Even I was not really into gay porn, culture, clubs, etc. I felt more comfortable and safer with these higher end seniors that were just looking for some sexual relief. Anal was off the table too, as it was for most of these guys. They were scared to death of STDs. There were plenty of ways to orgasm without going up the poop chute. I even got picky towards the end of those 3 years and would be disappointed if my man didn’t live in a gated community, have a pool, and a nice king-size bed for our trysts. I even had a few that bought me lingerie and perfume that they particularly liked. I for sure looked better that 98% of the old ladies I saw around me in Florida and came baggage free, pun intended! I made it an artform and put some effort into it. I had morphed into a mistress for wealthy senior men kind of by accident!

I learned a whole lot about making love to older men in Florida too. Many were lonely and just talking comfortably at first was huge. Moving slowly and starting with a soft, gentle kiss on the mouth was the best way to begin and let the passion ignite naturally. I also found it helpful to be the first one to get naked to arouse my lover, as many of them were shy at first. Once I got my hands on their cock, I noticed vigorous jacking while I was kissing them primed the pump. Lots of moaning and expression of passion on my part helped. I wanted them to know they were turning me on too. Once I could get my mouth around their cock; we were off to the races. No pussy would ever feel as good as my sucking and tongue swirling. Cradling their balls in my hand as I sucked them seemed to be enjoyed too. I don’t think there is any better feeling than a man filling my mouth with his precious love goo and gratitude. Some of these guys had some impressive old hogs between their legs too, and I surely enjoyed getting them up and running again. One of my lovers jokingly told me my having sex with older men was akin to restoring classic cars! If so, it was a hobby I surely enjoyed! These are the lessons I first learned with John.