First Times

A little background is in order. During my teen years, I became involved with a woman that helped me discover the pleasures of my female side. Sue helped me to dress and act in a very feminine manner. We were almost like sisters in the way we became so close.

She would sometimes describe how good her boyfriend would make her feel when they would make love. She seemed to think it was funny seeing me squirm when she would get a little too graphic. I know she was only giving me a playful hard time.

She did get me to admit that I was just a little curious about what it would be like to be with a man. Each time she brought up the subject, I would say "No Way". I couldn't be with a man until I felt more comfortable being a woman. After she married and moved away, I wasn't able to dress as often.

I purged myself of all my clothes and jumped into what I hoped would be manhood. Four months after she left, I joined the military.

For several years after I joined, I act like Joe Macho. I would do just about anything trying to prove my manhood. But then it happened, I was in a mall one day with some friends. The wife was in the lingerie section of the Ladies Department. Her husband and I were like all guys, in that situation, trying hard to not be there.

As I made my way past several racks of bra and pantie sets, one set in particular caught my eye. It was a pink lace baby doll set that reminded me of the first set of lingerie I had tried on.

The old urges to be a woman came flooding back. I tried to convince myself that it wasn't going to ever happen again. I even had my reason why I could never do it. I was in the military. If caught, I would be thrown out with the black mark on my discharge papers. Worst case would be if some of the guys in the barracks found out. I would be the subject of a blanket party or worse.

The more conflict I had within me, the stronger the urges got. I even tried writing to Sue about what was going on with myself. After 3 weeks and no letter from Sue, my will power caved and I devised a plan to at least try dressing.