Am I Still A Virgin??

I'm a middle-aged, married, bisexual, semi-passable CD (I hate the words 'non-passable'). I've dressed for a few years, but for a multitude of reasons have never had anal sex. I saw an ad in Craigslist (CL) that seemed perfect for me. It ran in their Casual Encounters "m4t" section (T means TG/TS/CD, etc. - although most of you reading this do not need an explanation because you probably live and brush your teeth in this category...lol)

The title of the ad was "Mature Man Seeks Fem To Dress". The text of the ad was long and detailed but the premise was this...

A mature man with ED (Erectile Dysfunction) wanted to take a fem guy, strip him down, dress him up in lingerie and then fuck him with a strap-on. Making out, petting, foreplay was all to be part of the scene and of course fucking.

It took a couple of back-and-forth emails for me to feel comfortable with the guy and him with me. His picture showed a tan-faced guy, 60+ years, who was taller and bigger than me. This is usually what I look for. I don't know about you other CD's who are reading this but with me, playing with a bigger guy just brings out that hidden submissive nature I possess even more.

The guy (I'll call John) thought he'd hit the jackpot with me because not only was I fem, I was also a practicing CD to boot (I'm mostly smooth - except from the knees down). In the beginning the knees-down thing was a problem for him but I sent him a pic of me in textured stockings and he decided I would be okay for what he wanted to do.

A couple of things helped me. First I don't think he had that many responses from other applicants; and if he did, I don't think the responders fit the body size he was looking for (me: 5'9", 145 lbs, trim, athletic body). The second thing was he was really excited to hear I was an anal virgin (except my wife's dildos).

Through the back-and-forths I learned that John was married, a businessman and had had ED for a few years. I had limited knowledge of ED when we first started our communications, but Wikipedia helped me to realize that ED has a quagmire of reasons for making it impossible for a guy to get an erection. In John's case even drugs wouldn't get him hard. I'll just say that between John and I (Kelli by the way) it was a subject that we didn't talk about, other then we both knew it was our purpose for meeting.