Thirty Years

At the age of fifteen I lost my anal cherry to a forty year old businessman. It was in a hotel room and I'd gone there at the request of the night concierge.
I earned really good money for what took an hour and a half.
Thirty years on and having kept myself fit, healthy and been a very convincing cross dresser, I've just had my one thousandth male lover.
I have the ability to remember them all. Whether that be in the hotel, where I entertained over three hundred men. Or in my own home where I later set up sex rooms for my lovers to enjoy me.
I also meet men without my slim fitting dresses, wigs and makeup. Often being fucked outdoors which I absolutely adore.
My thousandth lover was a younger married guy, someone who I got to know through the Internet. He fucked me in a hotel in the countryside, and we spent the night together.
However I'm here to tell you about the start of two thousand lovers.
A friend tracked him down and I booked into the same hotel, using their best suite.
He's the forty year old, then, businessman who took my cherry thirty years back. He was only too delighted to be given the chance to fuck the boy he had all those years before.
As a seventy year old he still had the sexual passion I remember and stayed overnight with me.
We spent an age sucking on each others cocks, as he enjoyed himself by finger fucking the hole he kept on telling me, he was going to destroy.
With a little help from a blue pill, he did precisely that all night and through into the morning, fucking me until he'd drained his balls four times.
It was a beautiful way to experience my first of my second thousandth. And before he left I told him everything was free, and whenever he wanted sexual relief to get in touch.
He and I have had sex several times in my home since. A home I might add I now share with a very understanding woman.
We don't have full on sex per say, as I don't fuck her. But most days when I'm not entertaining, i'll gladly spend an hour or so giving her cunnilingus. It helps with giving larger cocked men a blow job. Works your jaw muscles in all different kind of ways. And she loves the oral attention.
I hope you enjoyed my confession, as its my life in part. And something I really enjoy in my life.