Tamara's Journey Through Trials and Tears

By Tamara Rivera

About the Book
When a child asks, “Why am I a girl?” or “What makes me a boy?” most parents might answer “Because God made you that way,” and that is the end of it.
But that is far from reality, and in this book, you will learn that gender as we know today is not what you’re assigned at birth but what is in the composition of your brain.
On a journey to be recognized and respected by everyone as a transgender woman, the author’s journal entries paint a picture of her experiences on this path. Tamara’s Journey Through Trial and Tears shares the highs and lows, successes and struggles, kindness and cruelty of her transformation as she takes command of her true place in this world.
About the Author
Today, she is Tamara Rivera 24/7 and is always working to stay in touch with the transgender community. She meets with local groups of transgender people for discussions and to build relationships, and follows groups through Meetup and on Facebook, where she has well over 2,000 followers, 95 percent of which are women who enjoy the positive inspiration she offers. Forced to leave school as a teenager to support her siblings after their father left, Rivera never lost her interests in space exploration and technology and still reads and watches YouTube videos on the subjects, as well as works in the technology field. She also creates nail art, has a group page on Facebook, and has sold some press-on nail packages, hoping to make this a successful business someday. Rivera maintains a close relationship with her ex-spouse and children.

• Language: English
• Publisher: Dorrance Publishing Company
• Release date: Jan 5, 2024
• ISBN: 9798889258438

Book preview

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The contents of this work, including, but not limited to, the accuracy of events, people, and places depicted; opinions expressed; permission to use previously published materials included; and any advice given or actions advocated are solely the responsibility of the author, who assumes all liability for said work and indemnifies the publisher against any claims stemming from publication of the work.

All Rights Reserved

Copyright © 2023 by Tamara Rivera

No part of this book may be reproduced or transmitted, downloaded, distributed, reverse engineered, or stored in or introduced into any information storage and retrieval system, in any form or by any means, including photocopying and recording, whether electronic or mechanical, now known or hereinafter invented without permission in writing from the publisher.

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Tamara’s Journey 

Through 

Trials and Tears

My early life

I was born on a warm Puerto Rican May 30, 1962, to proud parents, the firstborn son and I spent my first year in Puerto Rico, and my parents moved to Chicago, Illinois where they bought a home. I spent my first year with my aunt Lydia in Puerto Rico and in 1963, she met with my parents in Illinois, and I spent my next ten years of life in Chicago, where I grew up and went to a Catholic school. As I grew, my first recollection of being different was at age five.

Living in Chicago, I had a good childhood. I grew up as a normal boy for the first ten years of my life. I discovered a lot of new adventures in my parents’ big home. My first boy’s toys included a baseball bat and a little red wagon as most boys had at the time. In my dad’s garage, there was an old rusted 1930s Ford that really interested me. One thing I hated though was winter, the brutal cold of Chicago. It was not until the early ’70s that my parents moved back to Puerto Rico and dropped me in school, which seemed to me like an alien place since I didn’t know a word of Spanish and learned the hard way.

The difficult part of the move back to Puerto Rico was learning Spanish since my parents did not focus on teaching my siblings and me while in Chicago. In a new environment and school where I learned Spanish full immersion. The hardest part, though, was soon after arriving on the Caribbean Island, I was just ten years old and totally innocent of many things. I used to occasionally wonder about women’s clothing. I liked the satin feel of panties and the style of women’s clothing, but it was not till one afternoon that changed everything forever and opened my eyes to a new world and allowed me to explore my sexuality at such an early age.

Sadly, what changed things for me though was the horror of being raped by an uncle when I was twelve. That event, though scary, opened my eyes to realize that I really enjoyed the sexual experience, later I began exploring cross-dressing, but how do I go about it? My mom’s clothes and underwear were too big for me at that age. I hated being raped, but it helped me realize that it was an event that got me started and I really loved feeling like a girl and loved the attention of boys.

My parents would leave us home alone and go to church and I would invite boys over to have sex with it was exciting, but one day I got caught and my dad was not open-minded and was very abusive, my siblings and I endured years of mental, verbal, and physical abuse from my father, we were scared of him.

I really loved having sex with other boys while wearing panties and sex was almost a weekly event.

I began to steal panties and clothing items from clotheslines from my cousins, sisters, and other neighboring girls to stack up on underwear I could actually wear it made me feel like a girl, I kept a shoe box in my room full of panties and other girls clothing items and then… one day while I was out, my mother found the box and she was very saddened. My mother was a devoted Christian and she tried hard to teach us the values that made her and shaped her life. She cried and prayed for me and for a while, I tried to forget about panties but never forgot that I really wanted to be a woman. I cried many times hoping one day I could wake up with a whole new body, but I know that was just a dream.

My parents were devoted Christians, and they were nice, but it was my father who was a challenge. He was always willing to get his hands on me for any little error or whenever he felt I was being disrespectful to him and the physical, verbal, and mental abuse was very hard on me and my siblings, I was the second of six, the firstborn son, but wished many times I was a girl. Maybe if I was, he would not have been so abusive, I remember my father had a fit of explosive anger, whenever I made the slightest mistake he would lash out at me, he was heavy set but fast on his feet, one afternoon I was playing in the front yard as he was sharpening a new machete that he had purchased, back then they were sold with a blunt edge and you had to sharpen them by hand, for no apparent reason he got mad at me and he shouted as he began chasing me with machete at hand and as he got closer I began to run, I was freaked and I began to run for my life as he yelled that it was not sharp, the horror was about to awaken.

My family lived in a small house next to my grandparents in a small village nestled between the mountains just outside of the city of Dorado close enough to the coast that you could hear the roar of the ocean at night and the Coqui singing into the night. It was a peaceful place. Later in the mid-’70s we moved to a new community built by the people that built the community. It was even closer to the ocean, and you could see it about a mile away past a cow pasture.

This was supposed to be a new start, new neighbors, new schools. By then I was in my early teens, and I began to shave my legs since I started to grow annoying body hair but since I was young no one would know that I was shaving my legs, at least that was easy. Sometimes when my parents were away, I would wear girl’s clothing and even mustered up the strength to step out in short cut-out jeans showing my legs as much as possible.

The horror began to get worse as my dad got even more abusive in all aspects of the world. Things got so bad that I really hated him. If I came late from school, he would beat me up. If I overstayed longer than expected at a friend’s house, another beating, and the situation was out of hand. One day I arrived home late from school—I loved school and would do all that I could to read books about my passion for cars, technology, and space. On that day I was late, and the librarian offered to bring me home. When I arrived, I noticed my father was standing outside on the lookout and he quickly came to the car as I got out. My father greeted me at the teacher’s car with a fake smile, but I could read behind the fake smile that he was mad, so I was ready for him.

That day changed forever or at least for a short period of time, I was already in the living room when my dad walked in and the first thing I got from him was his flat open hand to my face, which threw me across the floor, stunned as I was, confused and tired of the abuse, all I could think of at the time was that I have had enough, he always kept a sharp three foot long machete at the door waiting for him to go to the sugar cane field. That was an opportunity for me to explode my frustration and anger as a teenager looking for some relief.

That machete at the door just fell into my hands and as my dad raced to hit me again he suddenly took a big leap back and fell to the ground when I stood up and swung that machete close to his midsection with two swift swings of that blade I could have killed him and when my mother screamed, she was really scared of what could have been and she turned to him and told him that he should stop being so abusive.

I suddenly realized that I could have killed my dad and my rage was so high now that I ran out of the house and down the block screaming like I was crazy, my mom ran right behind me when she caught up with me, she hugged me and cried along with me. After that, my dad slowed down for a short time knowing that things could get out of hand.

My relief came one day when the police showed up at my parents’ doorstep to arrest my father and little did, I know the reason till days later when the news broke out that he was raping my sisters. One thing you don’t do in most Spanish countries is mess with children, which could lead to a mob of angry people taking justice into their own hands.

That faithful day brought so much relief to me, no more beatings, no more physical and verbal abuse, and no more of the man that I hated so much, I wanted to see no more of him, and shortly thereafter my mom moved back to our old home behind my grandparents.

After the arrest of my father, I started a new life free of the oppression that he represented in my life, a fresh start, and a chance to be me. My mom was more flexible in her Christian views, she really cared about her children. We moved back to live again in a newly built home on the same land where we started behind my grandparents’ home. I had so much more freedom.

I felt good since now I was free to be me and explore my next move to be a woman. I remember one day I was very sad since all that I could think of is why did God make me a man and not a woman? I questioned him and so I went behind my mother’s home one night after everyone was asleep I wanted to question the creator, with the Coqui singing coqui, and the wind calmly blowing between the mountains and the sky lightly lit by the moonlight on a warm summer night I prayed God and I asked why I was born a boy and not a girl, why don’t you grant my wish to be a girl. I explained to him that if he makes me a girl overnight, I would be so happy. I would wake up the next day to reality. I dreamed many times of being a girl and wanted to stay sleeping as that was the only time I was living as a girl, but the morning came, and I woke up the same as before.

I had the freedom to go sleep at my neighbor’s home just to sleep and have sex with the boy next door. He was my first and only real boyfriend. I revealed myself to him one day as I invited him to the outhouse behind my mom’s home one afternoon and told him that I liked him and showed him I was wearing panties and was ready for sex with him. I began drinking with my friends and having sexual orgies with more than one boy at a time, which lasted for a couple of years, and I really had fun, I felt so much like a girl, and I had no one to stop me or abuse me for who I was.

That all ended one day when I was out of work for a while, and it was very hard to find a job at the time in Puerto Rico. My father did not spend much time in prison as he was a model prisoner and after leaving prison since my mom had divorced him after he left prison he moved to Atlanta, Georgia where he lived out the rest of his sentence after spending just about five years in federal prison back in Puerto Rico.

After my father’s imprisonment and my parent’s divorce, I was approached by my grandfather and he advised me since I am now the man of the house that I should quit school and go to work to help my mom support my siblings, I was thought to respect my elders and my grandfather was very close to me, I loved him, this was very sad since I loved school and had big dreams of being a scientist or an artist, I loved drawing but all that fell behind when I left school to work.

It was hard bouncing from one job to the next till I landed a job in Dorado painting murals with a Puerto Rican artist in the town. I worked there for a while till the job was completed and again bounced around from one job to another. In the meantime, I spent my free time going to bars when I was still too young, but no one ever questioned me. I met gay men and had sex with some but that was not what I wanted till I met some cross-dressers; I made a few friends but being without a job was hard. That was when I heard that my dad was in Atlanta, Georgia, when my dad heard that I needed a job he wrote me a letter and offered to help me get a job and though I had some reservations I was forced to move to Georgia to live with him.

I suddenly found myself right back with a man that, though I hated, I wanted to give him a chance since he was willing to help me. It looked like he had changed, and he was nicer but still, a bit controlling. He made plans with my hard-earned money and at tax time he made plans with his and my money to buy appliances, furniture, and a car. When I realized that I was my own man and I needed to put my foot down and make my own plans with my hard-earned money.

One day tax season came, and he was planning on buying a car but again it was with his money and mine. I had other plans that did not align with his. I wanted to show him that I can make my own decisions and hoped that he respected that, so I bought a moped with my tax money and when he returned home after work and learned of my decision, he got so mad and told me that I had to return it and get my money