When I was fourteen I was sent to a military boarding school to man up. I was a pretty big sissy at the time and I guess my parents felt that I should be in an all male environment to become a man. As a sissy at a boarding school you stand out as soon as you arrive and you become the girlfriend of an older dominant male. It hurt, it hurt like hell, but you don't complain. You take it because complaining will not help. You know from the moment that you show up there that you're the sissy and that makes you the girfriend.

By the time Christmas break came, and I could go home I was broken in and was all girl. I got home and was even more of a sissy than when I left. But now I was experienced. I hooked up with my older sister's friend, he was a real jock, but he liked sissies. And he was experienced, he knew what he liked and after a couple of times I was pleasing him. He was the perfect jock, so I was sworn to silence or he would hurt me. I wasn't going to tell, I liked being his girlfriend.

Back at school I went back to the being the girlfriend of my upperclassman. At school you were divided into sissies and non sissies, and as I was a pretty overt sissy I could act any way I wanted. Uniforms were the order of the day, but not pajamas or underwear. My boyfriend bought me things to wear and I wore them for him. There were other sissies at school, and some like me wanted to express ourselves and others kept it bottled up, suffering terribly when they were taken out for a joy ride. But for me, boarding school was made to order.

As I moved through school I was the girlfriend to several upperclassmen, and in my senior year I was the girlfriend to one of the DIs. He was Mr. Macho Man, a tough no nonsense DI, with a lot of appetite for a girl friend on campus. When I graduated, I joined the army. This was before don't ask don't tell, so discretion was important. But all good boys want girlfriends, and I was never alone. I had dates every weekend and some were bang up weekends.

After I was discharged I went into insurance sales, home, auto, life, stuff. I had an office in a class c building and an active social life. Across from my office was a Hyatt Hotel, and Friday and Saturday nights you could always hook up in the bar. These were blind hook ups, no real names, as these men were married with families and discretion about their activities was the order of the day. For some I would dress and for others we were just two buddies sharing a drink, until we went upstairs to the room. My thirties were a forever fun filled time.

My forties were tough, an older sissy just doesn't get respect. And forget your fifties. Now I live on my memories, but finding a casual acquaintance for an anonymous hook up is near impossible. I mean a real high end hook up, there are creeps out there on the internet, but who wants to wake up with surprise that ruins your life.

I am looking for an older descent man to hook up with, sure the spark of adventure is more difficult to start, but maybe a good time can be had, although the action would be more subdued.

Some time I think of my mother's old song, the Old Gray Mare, except I am the Old Gay Mare. My memories are vivid, and my heart is in the right place, but who wants an old sissy to spend time with. Now I have said it all.