Summertime Cross Dresser Confession

Certainly, it wasn't easy being an English teacher to these ghetto residents, but he wouldn't want to do anything else, that is, except now to retire. In his first few years teaching here, they threatened to kill him. They still threaten to beat him up and flatten his tires. With enough of a collection of confiscated weapons to fight a war, he had flushed enough drugs down the toilet to start his own pharmacy.

Typically, unless the offense was more serious, he didn't even bother to report them or have the principal call the police, their probation, or parole officer. Their safe haven, his classroom was the only place where they could divulge their true feelings without having to swallow it and keep it bottled inside. The only way that he could inspire their thoughts, this was the sanctuary of creativity that they need to show them that life was not all bad. Free to say and write anything they wanted, he wanted to inspire creativity and not extinguish it by making them fearful of being reprimanded or judged for what they wrote.

"Write 500 words of what you did over the summer," he said and at the first protest, always when there was a protest, he'd doubled that amount. "No, make that 1,000 words because of Mr. Martinez's unhappiness with the minimum word count. Apparently, Mr. Martinez doesn't think that 500 words is enough words to tell us all he did over his summer. Does anyone want to make it 1,500?"

If that was his assignment last year, he could have written one hundred thousand words of what he did over his summer. His wife left him, when she found him standing in their bedroom in his mother's clothes, dressed as a woman. To this day, vulnerable and sad, he still doesn't know why he did that, why he allowed her to see him dressed like that. He knew she'd be home from work soon. He knew she'd catch him. He didn't care.

Maybe he was tired of living a lie. Maybe he knew what her reaction would be. Maybe he wanted to be caught and to finally end the facade and the charade of a marriage they tiptoed around all these years. For her to leave him flat, for her not to discuss his actions and just go, she was on her way out the door anyway. Maybe she knew he was a cross dresser. How could she not know?

Of no consequence to him, she had a boyfriend on the side for years. Closing his eyes to it, he knew about it. He even understood it. Not surprised, he expected nothing else from her. A farce of a pretense just going through the motions, their marriage had been over long before she cheated on him

Yet, he couldn't help but wonder, if maybe he was to blame. Maybe he was the reason why she sought the comfort, the sexual contact, and the love of another man. Maybe in his need to be the woman that he always should have been, he wasn't there for her. Maybe, maybe, maybe, he had so many questions but none of the answers. Who had the answers? No one that he could find. For such a smart man, someone who knew all the answers of the great literary works, he was dumb when it came to figuring out himself.

What made it worse was he had no one to talk to about how he felt and what he was feeling. No one knew he was a cross dresser. No one knew he suffered inside with his internal struggle wanting to be a woman and not a man. No one knew, not even his brother and/or his sister. Who knows? Maybe he was just kidding himself. Maybe after all these years, they all suspected. Maybe they all knew but didn't know what to say or what to do. Typical behavior when coming across something not understood, just ignore it, before sweeping it under the rug, while hoping that it doesn't resurface again.

Unfortunately, the timing of his wife leaving him couldn't have been worse. He had just buried his mother. As a boy, he used to dress up in his mother's clothes. He loved the feel of her clothes and the smell of her body and her perfume that remained on his skin and that lingered a warm memory of her when she was alive. Maybe, dressing up as his mother now that he was an adult was his tribute to her and his way to evoke a memory of her when she wasn't ill.

She was a good woman and he loved her. He missed her now that she's gone. Maybe, mourning the loss of his mother, he just missed his mother and wanted to feel closer to her by wearing her clothes. Maybe it was time he lived the life that he always wanted to live and be the woman that he always wanted to be. Although he didn't have her to help him grieve, he was glad his wife was gone because, too wrapped up with herself and her feelings, she'd never understand any of that about him.

Obviously, his wife would never understand any of what he had to endure. She had lived a charmed life. Her Daddy took care of any problem she had. Now, that Daddy was gone, she had his money to buy her way out of her misery and even out of her marriage with him by giving him what he needed to live a comfortable life without her and without having to work.

Who knows, maybe she understood more than he gave her credit. Maybe she was closer to her Daddy than he realized. Maybe she had been a victim of sexual abuse in the way that he had mentally abused himself with the misery of thought over the guilt and shame of cross dressing that he had burdened himself with all these years.

She was so immature and he was stupid for marrying a younger woman. Ten years older than she was, she turned his head with her beauty and her energy. Now that he thought about it, maybe she was looking for another Daddy. Captivated by his charm, she was enamored with his intelligence and creativity. Then, when they couldn't have children of their own, without that much needed mortar to keep them connected, just as if bricks crumbling in their foundation, they started growing apart.

Now that he was older, he was ready to retire. He had enough money saved that he could move to a place where no one knows him. He could finally grow out his hair and fingernails and get the breast implants he always wanted to have.

Even though he had thought about it for decades, he figured he was too old now to safely have a sex change operation. For sure, he'd have to leave the country and go to Denmark, Mexico, or South America possibly, to have that kind of surgery done. Yet, that kind of major surgery scared him. He wasn't so sure he even wanted to have it. He had discussed it with his therapist and read about it, but he liked being a man and he loved his penis too much. Besides, so many things could go wrong. Just the expense of it made him reconsider the cost versus the benefit, especially now at his age. Then he'd have to take all those hormone replacement drugs, it just wasn't worth it to him.

Now that he was older and didn't have the libido he once had, the operation wasn't about having sex with a man, as a woman. He never wanted to have sex with a man. Although maybe had he had the sex change operation, perhaps had he had all those female hormones surging through his body, who knows? Maybe he'd want to have sex with a man. Yet, it was never about that, about sex with a man or with a woman. It was more personal and more about him. It was for himself and no one else that he'd want to change his sex to live the life of a woman.

Truly, it was more about that. It was more about living his life as a woman than about having sex with a man. He finally realized that he didn't need a sex change operation to do that. For sure, it would be enough for him to dress like a woman, let his hair grow out, get the breast implants, and take a few hormones to inhibit his testosterone and stop his facial, arm, and leg hair growth. He was excited about the prospect of finally living life the way he wanted and needed to live it.

The only time he was glad he didn't have children to embarrass or to judge him, he'd be happier living out the rest of his life as a woman. Finally, a dream come true, he no longer needed to hide who he was. Instead of Samuel, he was now and forever more to be called Samantha.