Summertime Cross Dresser Confession


After a long time coming, a lifetime of suffering, the first day of summer is when an aging cross dresser finally gives into the life he’s always wanted to live. As if a new beginning, as if being born again, Donald looked to his transformation from man to woman, as his emergence from moth to butterfly. He couldn’t wait to fly away to start his life anew.

Preoccupied with his panties, trying to remember if he was wearing the pink ones or the blue ones, he was having a senior moment. For the life of him, he couldn’t remember. He’d have to take a men’s room break, later, to see.

Just a fantasy, Donald had the urge to wiggle his way down to the men’s room. He could only imagine what the other teachers would think, if they saw him sashaying down the school corridor and putting on his Raquel Welch walk. What did he care? It was his last day teaching here anyway. Besides, there wasn’t a good looking teacher in the school, except for the real young ones, the ones just starting their careers, that he’d feel embarrassed by them suspecting that he was a cross dresser. If only they knew what he was thinking, when he was checking out the female teachers. He wasn’t checking them out as dating and mating companions, as much as he was checking out their clothes.

No matter, whichever color they were, these were his favorite style of panty and the most comfortable to wear. Even though he preferred the feel of silk and satin against his skin and slept wearing those at night, for the sake of comfort in wearing them for a long day in a hot classroom, he always wore the cotton ones. Only the cotton ones came up high enough to make him not feel that his panties were sliding down during the course of the day. The lacy ones were his prettiest panties to wear, but they were itchy and he wondered how women wore some of the things they wore. His most expensive panties, his frilly panties, he only wore those when he wanted to feel sexy. He wore those on special occasions and celebrations, such as his birthday, usually after taking a candle lit bubble bath with soft music and champagne.

A bit of a hypochondriac, when he had his memory lapse, he wondered if it was the start of Alzheimer’s disease. Then, he figured, with all the excitement of this being his last day of school, he was just filled with raw emotions. Having taught for more than thirty years, nearly half of his life, he had a good career.

If his students knew he was wearing women’s panties beneath his clothes, for sure, they’d think there was something wrong with him. No doubt, they’d think he was gay, but he wasn’t. A heterosexual man who loved spending time with women, he just enjoyed wearing women’s clothes, always has and always will. A big part of his life, he wasted too much of his time with negative thoughts, with the guilt, the anger, the shame, and the pain he suffered from cross dressing.

Never feeling comfortable enough with his private life to tell anyone, cross dressing was his secret to bear. Tired of fighting his pressured need to stop dressing like a woman, wanting to live a life without cross dressing, he wanted to live life like any other man. After swearing off wearing women’s clothes and throwing out his entire wardrobe of dresses, shoes, handbags, and wigs several times before, finally giving in to it, he gave up questioning his inability to stop.

Looking for answers that didn’t exist, wanting a reason to justify his need to cross dress, he went from psychiatrist to psychologist without satisfaction. In the course of his lifetime, he already spent thousands of dollars on therapy that didn’t work and that confused him more than it helped him. He learned the most about his condition or fetish through support groups and by talking to men, strangers actually, who shared the same need to cross dress and who had the same feeling that he had before and after he cross dressed. He hadn’t been to a support group in years, but it was a Godsend to discover that he wasn’t alone and that there were other men just like him with the same need to wear pretty, feminine things.

If his students knew he was a cross dresser, they’d make fun of him, before beating him, and then shooting him. This school wasn’t the school for the wealthy white kids that he taught in most of his career. Wanting to give back something, wanting to leave his own personal legacy behind, after having taught school for so many years in the better neighborhoods, he took a job here, just outside the ghetto. Hoping to turn their lives around, this was the school for those young men, who had disobeyed every rule and broken nearly every law. Deemed hopeless cases, this was their last chance to turn their lives around by becoming literate. Ordered to come here by a judge, they had been ordered to learn how to read and to write.

With this his last day of teaching before retiring, coinciding with his summer vacation, and with his change of lifestyle, Sam thought about all the papers that he asked his students to write over the summers. He’s had more than 30 years of teaching twenty-five student mecidiyeköy escort classes, five classes a day. He figured he’s taught over 4,000 angry, immature, and disinterested high school kids how to write. Only, none of the students he taught now were kids. They were all grown men. This was a special school established with grant money from a wealthy patron, who started her life as one of these kids and this was her way of giving back to her poor and disenfranchised community.

They youngest in his classes were eighteen-year-old convicted felons, when they should have been fifteen-year-old promising students in high school on their way to college. The oldest were his 21-year-old last chance special cases faced with prison, the military, or this school. So many of them were either kept back, dropped out, or arrested, and a condition of their probation and/or parole was to return to school and to learn how to read and write. Able to get away from the rest of the gangbangers, able to be bused from the inner city out here to the country, a safe haven where no one knew them, they were the perfect candidates for this school.

He had the worst of the worst, but if he could reach these street urchins with kindness and a promise of literacy, then he could reach anyone. Moreover, he felt that he was making more of a difference helping these men than teaching rich, white kids how to improve their writing skills. They already knew how to read and write. These men could barely read.

In a way, these men were more like him than any of the other kids he taught. Isolated by their illiteracy, he was isolated by his need to cross dress. They were both outcasts to a society that didn’t accept them. Neither of them were welcomed and embraced as the norm.

Just as if these men walked down a crowded sidewalk, while wearing their street faces, gangbanger clothes, and face and neck tattoos, people would move out of their way to allow them to pass. Those same people moved out of his way when he walked down the sidewalk dressed as a woman. For sure, he made for an ugly woman. Too tall, especially wearing heels and a wig, and with nothing soft about his facial features with his big nose, Marine Corps drill sergeant chin, and Frankenstein forehead, but that didn’t stop him from dressing as a woman.

No doubt, other than to write graffiti on a wall, a stickup note when robbing a bank, an extortion note when shaking someone down, or a ransom note when kidnapping someone, but for a grocery list for their weekly trip to Wal-Mart, most of these young, troubled men, will never write another word, again. Yet, there was always a few in his classes with the gift, the talent, and the desire, who thanked him for the inspiration that changed their lives, forever. Those were the ones who made it out and made something of their lives. Those were the ones who made it all worthwhile. Those were the ones that helped him through his days, when feeling so alone with his self-deprecating thoughts of wishing he was born a woman, wishing he wasn’t born at all, and wishing he was dead. Gone were the thoughts of wanting to kill himself. Finally, he was happy with who he was now.

Seeing that he reached one in twenty-five or even one in a hundred young adults, as a writer, a teacher, an educator, and a molder of young minds, made it real and gave him the reason and the motivation to continue teaching. That’s what teaching was all about to him making someone love what he loves, reading, learning, and caring about the art of writing. With writing a lifelong apprenticeship, that’s what happened to him, when he was a kid, with one teacher changing his life and making it better. That one teacher, when he needed the help the most, helped him to put his thoughts and his secret feelings, wants, needs, and desires to paper. That one teacher and all these needy students is why he loves teaching and will miss it, now that he’s retiring.

This, his last class, his students don’t know he won’t be back in September. If they knew, they wouldn’t bother writing the paper that he was about to assign them over the summer. Besides, it was always interesting to read what they wrote. He’d return just for that. Just for the experience of reading their summer vacation essays is a reason for him wishing to return to teach for one more year. Only, he was done teaching.

He had enough. He had nothing left to give. He needed to do something for himself. He needed to start living his life, the life he always wanted to live as a cross dresser and as a woman. This was his opportunity. With the summer off, the first day of his retirement, and enough money saved to live somewhere less expensive, he was eager to open a new chapter in his life. Now that he doesn’t have to work for a living, he’d just write.

Never knowing what they’d write was his treat in reading all of those What I Did Over My Summer essays. Unlike when he was teaching English, specifically creative writing in the better, white neighborhood schools, too many of the Caucasian kids there had nothing vip escort istanbul to write about, other than the trips they took with their parents and the things they bought at the mall. An endless cycle of the haves versus the have nots, already just as bored and boring as their parents, they were just as boring as they’d be when adults and married with children.

If one of those kids spent a summer here in the ghetto, their lives would be changed forever, that is, if they survived the summer. He wondered how different society would be if they bused kids to different neighborhood every summer, the white rich kids living in the ghettos with the roaches, rats, and crime, and the black and Latino kids living in their rich suburbs with the swimming pools, summer vacations, and plenty of food to eat. A good topic for a story, maybe he’d write that one day.

It was different and definitely more rewarding teaching English and creative writing to the residents of the ghetto. Good or bad, mostly bad and spiced with street smarts, these young men already had a real feel for life that their white counterparts could only touch upon reading fiction, watching television, or watching movies. Not even a high priced lawyer could pull the wool over the eyes of these men without them seeing right through him or her. Molding them, as if they were made of clay, wanting to inspire them, as he was so inspired, these young men already had a lifetime of stories to tell and all he had to do was to teach them how to show their stories in the words that others could understand.

Over the years, there were some real heartbreakers, a mother overdosing in front of her son or a dad being shot in front of his daughter. Typically, it was the constant crime, the real fear, the unadulterated hatred, and the verbal and physical abuse that they wrote about. Without them even realizing it, their summer vacation essays were cathartic, probing, raw, and real. He should write a book called Essays from the Ghetto. Only, it probably wouldn’t sell. Why would anyone buy his book, when they could just read the daily newspaper or the police blotter to read the crime, despair, and hopelessness that permeates the ghetto? Sadly, the general public would be more apt to read and interested to know about a celebrity falling off the wagon and going into rehab than to read about a nobody making it out of the ghetto.

Not having enough food to eat, clothes to wear, and being envious of how white kids are characterized on television, as having a happy home life, the stories of his students were as painful, desperate, and dramatic, as they were real, informative, and insightful. Typically, the subject of their stories was their neighborhood life. These people that sat in front of him now were more intriguing and engaging than those most unforgettable characters highlighted in Reader’s Digest. Even though their lives blended together into one daily misery of common crime filled occurrences, each one holding a different piece of broken mirrored glass, all of which fit the same puzzle when put back together, every student had a unique story to tell.

“What’s your story?”

He looked out over the disinterested faces of young men who didn’t want to be here. They’d rather be anywhere else but here, that is, except for prison and if this was their way to stay free from incarceration, then so be it.

“What do we write about, Teach?”

Javier looked up at him with a shrug. He didn’t have a clue what to write. The toughest man in class, he could write volumes about his life on the street. As soon as he asked what to write about, as if it was now okay to ask with Javier giving them his permission, the others looked at the teacher, too.

Many of the real tough kids, he still refers to them as kids, when in fact, they are grown men, are unreachable, even for him. Most of the tough young men, those harder to reach, those hanging on from a thin thread, and those who’d never make it to graduation, called him Teach. He had seen their dead eyed stares and emotionless faces a thousand times before.

As most people do with a group, such as this, they all look the same, a mass identity of race, nationality, and prejudices. Yet, he had a talent, a gift for seeing the individual man without lumping him together with the others and without judging him as the same, as not lost, but broken. Each one had a name. Each one could be fixed, instead of locked away in prison or shot dead on the street.

Every time he put his head on the pillow, he wondered how to reach his students to make a real difference in their lives. It’s hard to turn around a life within an hour class, when they return to the Hell of a life 24/7. Still, if he could light a spark, if he could inspire them to open a book, instead of load a gun, maybe he’d make a difference.

“Write what you know, Carlos. Write what you did over the summer, Tyrone. Write about your life, Willie.”

Always they had the same response and always he had the same answer.

“I don’t do sarıyer escort nothin’. I don’t go nowhere. I don’t know nothin’.”

“Ah, but you do, Jose. You do, Jackson. You know a lot,” he said with a smile. “You’d be surprised how much you know.”

“What do I know? How do you know what I know or don’t know, Teach?”

Immediately, whenever he tried getting too close, the attitude surfaced. Unlike the well-off, polite, white kids, that suppressed their emotions, he never knew what they were thinking. These underprivileged men with their emotions poised so close to their skin, knew more than they thought they knew. They already knew more about life and about death than many others would know in a lifetime.

How many of his privileged white students have seen someone put face down on the pavement, disrespected, demoralized, and arrested? Gone in a blink of an eye, how many of his well off white students have seen someone die before their eyes? Educated on the streets, all of these men had the instincts, but from the other side of the law, of a street cop. They more trusted their gangster role models than they did the police. They put their trust in street justice more than they did in law enforcement and the criminal justice system, and in the way they’ve been treated and discriminated against, who would blame them?

These men could sum up a situation, before it even unfolded and before they were victims. Compared to the white kids from the better neighborhoods, they were tough and they knew plenty. They already knew everything they needed to know in life to avoid death, so long as they didn’t succumb to the watershed of shit that surrounded them. Honestly, he’d rather befriend one of these young men, one of these underprivileged curmudgeons that made it out of the ghetto, than a spoiled, rich, white kid. Definitely, all of these students would have more substance and more things of interest to write about in their summer essays than any of their white peers.

He could only imagine the stories that they already had buried inside them to tell. He just needed to find the key that unlocked their trust, their willingness to share, their creative spirit, and their desire to put their stories to paper. Just as he felt so lost and alone in his desperate need to dress as a woman, he needed to inspire them in the way that he was once so inspired. Had it not been for his writing, had it not been for the therapeutic help that he was able to give himself through reading the writing of others, by writing his own stories, and in teaching others how to do the same, he would have killed himself long ago.

“Write what you know,” he said again. “Don’t kid yourself. You guys know plenty.”

He’d sit on the edge of his desk looking out at the young faces that already showed evidence of hopelessness and despair. Sixty-year-old men in twenty-year-old bodies, too many of them would never see another year of life. Too many of them were here, just because they had to be. Yet, if he could find the switch in their heads that made them want to be here, he could only imagine the difference that he could not only make in their lives but also in society. Mistrusting of him and of everyone, they already had tired, sad, old eyes. It wasn’t easy to motivate these students, but if only he could reach them and pull them out of the muck and mire that was their daily existence, what a resource they’d be to society.

“I could write about my grandmother. She’s really old.”

He laughed, figuring that he was much older than any and all of their grandparents and, sadly, he was right.

“How old is your grandmother?”

“She’s thirty-eight, Mr. D,” said Rico. If they didn’t call him Teach, they called him Mr. D.

“That’s not old for a grandma. My grandmother is 45,” said someone else. “Now that’s really old.”

He was older than the oldest grandmother by more than ten years. How sad is that?

“Mine is only 33-years-old,” said someone else.

Thirty-three-years-old and the woman already has a child old enough to reproduce.

“Why write about her?”

He asked the question already knowing the answer.

“Well, I figure, she’s already had an interesting life. She had to turn to stripping at the club and then she started doing some prostitution and selling and doing drugs on the side, before they arrested her. That’s why I had to go to Juvi Hall, when I got picked up for shoplifting, because the state wouldn’t allow me to go back to living with her, once they released her from jail. She got probation, but they said she couldn’t watch me and take care of me anymore, when she couldn’t even take care of herself.”

Unbelievably, a typical story, there was always a sad story to tell. He feared losing these students to violence, crime, and drugs and losing their stories forever. Already living a worst scenario nightmare, aside from their twisted own, the only reality that they knew was what they saw on television. Even though most didn’t have a grasp of the language, they were still able to paint a dark enough picture of their pained hopelessness in their stories. Even the happy stories were sad. Instead of the happy endings their counterparts wrote, every story these men penned ended with violence, retribution, and revenge. Their eye for an eye was their happy ending.

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