I was turning forty in a few days and feeling a little down. I think all birthdays that introduce one to a new decade have that effect, but forty has always been the cliched one you hear about. It makes sense too, as it has become the official marker of being middle-aged. That is if you are lucky enough to reach eighty and beyond!

I had not set the world afire, but I never had much ambition or direction really. I pretty much just drifted and partied through life up till then. I had already been married and divorced twice, and being a good husband was not in my skill set. I had actually fallen into a pretty good gig by my middle thirties as a geriatric CNA working private duty for a very high-end clientele in Florida. It could be challenging work, but easier than hard manual labor. Much of the time you were just a pleasant and understanding companion.

I did have one kink I kept under wraps through two marriages and life until my late thirties. I was a secret crossdresser. No one ever saw me doing it and I never got too fancy with it. I would also imagine I was the woman when I was having sex. I didn’t really feel gay or enjoy gay porn, I just wanted to be the woman in sexual situations. That opportunity arose when I met Bob.

Bob was a very successful retired businessman in his early sixties whose wife has been stricken with early onset Alzheimer’s. My reputation as a CNA who did well with female dementia patients had spread throughout the very high-end retirement community Bob and his wife lived in. I soon found myself caring for his wife while earning a very healthy paycheck. Bob and I instantly hit it off. As is so often the case, the spouse of a dementia patient often has no one to talk too and they become isolated. I learned early on a huge part of my job was providing companionship to the caregiving spouse too, and Bob made that very easy to do, as I truly liked him. We were opposite in every way, and I believe that was part of our attraction to each other.

One afternoon Bob and I were in a deep conversation, and confessions were being exposed right and left. He brought up how much he missed having sex with his wife. One thing led to another, and we ended up in bed together for a very nice afternoon of sensual pleasure. I told him about my crossdressing, and he became quite excited about that kink in my persona. We became lovers and he supported my crossdressing emotionally and financially with outfits, wigs, make-up, even electrolysis! Bob used to joke that he built his very own sexy bitch from scratch! I was very slim, petite, and had feminine facial features as it was, so I ended up looking very sexy if I have to say so myself! I would care for Bob’s wife first thing, then spend the rest of my shift in bed with Bob. He was one blue-pilled fueled insatiable old dude with a big, tasty cock to boot!

Bob and I were both new to this and learned as we played, and the classes were extra fun! After a couple of years, I got very good at being a woman in bed, even without any anal component to our sex. For some reason anal sexual activity did not appeal to me or Bob. We both found many other ways to pleasure each other without going up the poop shoot! Cock sucking, jacking, kissing, rubbing against each other in many positions and ways. It always ended with me nestled against Bob’s manly chest with a gentle smile on my face and often a little cum too!