Crossdressing Teacher Learns His Lesson

I had always dreamed of being a pretty girl. As a young boy, I was forced to play with G.I. Joes while my sisters took pleasure in playing with Barbies. I jealously watched as they played dress up with my mother’s clothes and makeup, and grew even more envious as they grew older and began dating.

I’d peak into their rooms while they prepared for their dates, painting their faces with various shades of lipsticks, blushes, and eye shadows. I lusted after their makeup, their beautiful, feminine outfits, and long, luscious tresses. I longed to be part of their ritual—the trying on of dresses, the curling of the hair, the applying of makeup—I yearned to be one of them. As I got older, I would wait until the last of my sisters left for a date then sneak into one of their rooms.

I’d first put on one of their bras, then panties, and a silk slip, usually trimmed in lace. My favorite part of this routine was slowly slipping on one of their dresses. At first it was just the clothing I’d put on, but eventually I started putting on their makeup and brushing my hair with their brushes. I’d end this habitual practice with a dab of perfume on my wrist and neck. I’d perform this ritual throughout my teens until I went off to college and the last of my eldest sisters was married off.

During high school and college I was quite the ladies’ man. I dated frequently and went steady with many girls, which made my macho father proud. I excelled at sports and received a football scholarship to a prestigious university. I married and had children with a girl I dated in college and went on to become a high school gym teacher and football coach.

Although I tried to live the life I was supposed to, I still yearned to dress and behave as a woman. I would closely study my wife as she performed the same routines that my sisters had years ago—from the application of makeup to delicately slipping into a dress or skirt.

She assumed I was admiring her beauty, but I was only observing with envy and fascination. It wasn’t until our youngest son went off to college, and my wife left me for a man who was more tender and loving towards her than I ever was or could ever be that I began dressing as I always desired and became a woman.

After a few weeks of cross dressing at home, I finally made my appearance as a woman in gay bar miles outside of my small town. As I sat at the bar and played with my hair (an expensive long, blond wig that took me forever to pick out), I shyly looked around. There were a few other cross dressers, all looking more polished and more feminine than myself.

After only one drink and an hour I was ready to leave when three young, handsome twinks sat down next to me. The most attractive of them glanced over at me, smiled, and nodded his head. I smiled back and winked. To him, this was clearly an invitation to chat, and so he did. His face looked familiar, but I couldn’t place where I’d seen him before. It wasn’t until he divulged where he was from that I remembered who he was: a student I had taught and coached in football.

Once I realized this, I tried to make an exit, but it was too late. He looked me in the eye, put his hand on mine, and said, “Hello Coach.” I was paralyzed and couldn’t move. He signaled the bartender, bought me a drink, and told me to stay. I obeyed. After finishing my drink he told me he was taking me back to his place. I demurely followed him.

Once we got to his apartment, he ordered me to get down on my knees. Naturally, I complied. He then unzipped his pants and thrust his cock into my mouth, telling me I was a bad girl in need of a lesson. He then pushed up my dress and spun me around. He grabbed my hair and told me to call him coach as he spanked me for being a dirty little girl. Next he asked if I’d ever been fucked, to which I replied, “No, coach.”

Then he pulled out a toy from Adam and Eve and told me he was going to pop my cherry. I felt nothing but pure ecstasy as he fucked me. After I came, he forced me to finish him off with my mouth. Once he filled it with cum, he sent me on my way, proudly proclaiming that he had waited years to teach “coach” a lesson.

Crossdressing teacher