How it all Began

I was in an upstate NY m4m chat room one evening when I was totally bored and again about to give up hope. Just before I clicked off I received the IM that has completely changed my life.

A lil bit about me: I'm 43, 6'0, 250 and husky. There has always been a feminine side hidden deep inside me that I've wanted to explore. I like to dress in lingerie and wear heels and act totally fem. I have been with a couple of older men that just couldn't fulfill my desires and still being a “virgin” I was still in search of the man to take my cherry. Giving BJ's is good but it was always me taking care of them then myself. I have spent hour upon hour watching shemale & tranny porn wishing I was one of those girls. I'm a bi-curious bottom, 100% closeted and when not horny or dressed - I'm as str8 acting as can be.

I spent the next 2 hours chatting with John. I found him charming, funny, intelligent and compared to the rest of the men I typically meet online, he easily had to be the most mature man ever. We talked about our m4m history's which were very limited for both of us, our likes, dislikes, even a fantasy. The chatting went so well I couldn't believe the 2 hours flew by. Over the course of the next month I learned he was in his upper 50's, 5'11, 185. His one true love passed away 10 years ago. He was well off financially owning his own business plus some family money, his kids lived out west and he saw them rarely as they started to begin their own adult lives. He had trouble dating as most women saw him as security and wanted marriage. He mainly just wanted to have sex and no commitments, which sounded good to me. He never felt he'd be able to fall in love again. He liked the fact that I liked to dress and act the female role. The best part was he lived 15 minutes away from me in an area I knew to be secluded and had some old big estate type homes. Privacy is a good thing when doing something like this. We also had some excitingly steamy chats and on 2 occasions by phone.