Be True to Yourself (A True Story by Cris Dressor)

From my childhood as far back as I can remember I have always been interested in women’s clothes. While my exact age escapes me, I remember going into my mom’s drawers and grabbing things at an age when most boys were playing soldier. Even in my single digits I had borrowed everything from bras, panties, and pantyhose to dresses. By the time I was a teenager I understood how it all went together. It seems silly now, but pantyhose goes over the panties, I even wore Kotex pads back before stickers and wings. I had no idea why and what the point of it all was. I just knew I felt normal doing it. Apparently, I was quite good at putting the stuff away as it was not until I was 15 my mom even began to suspect one of my siblings or I was using her stuff. She even sat us all down and asked more than once about who was getting into her drawers. We all looked around at each other in bewilderment. Shortly after my 16th birthday, my folks and my brothers and sisters were going on a vacation. As the oldest of 5 kids, I was to stay behind because I was working at a restaurant. My cousin and his family were my back up if something happened while my parents were out of town. They were leaving early in the morning and we had already said our goodbyes the night before so I was still in bed when my mom came in to say a final goodbye. I was wearing one of her black full slips as a nightgown. As she reached in to touch me, she saw the strap. She smirked and did not say anything, but I knew she saw it. I was freaked out for 2 weeks.

When my family returned, my dread had turned to absolute fear, then to relief as nothing was said for weeks and I assumed that she forgot. With my minimum wage job, I was able to afford things. Keep in mind this was the mid-80s. The internet and Amazon did not exist yet. As a 16-year-old boy buying women’s clothing at a department store was not an option. The Sears and Roebuck catalog was a young male crossdresser's miracle book. I had saved some money, about 30 or 40 dollars, as minimum wage was approximately $2.30 per hour, this was a substantial amount. I ordered some panties, a bra or two, a full slip and pantyhose. I think I even bought a one-piece swimsuit. I went to a local grocery store and got a money order. I rode my bike to the post office and mailed the order form and money to Sears. I was quite impressed with myself; knowing that no one was the wiser. A few weeks of trepidation and I knew the order was arriving soon. I would check the mail every day when I got home from school. Each day the package did not arrive the suspense grew. One day I came home, again to an empty mailbox. I walked in the door and there it was, the package I’d been waiting for, my very first brand new girl stuff. As I approached the table, I realized the package had been opened. My mom looked at me with a strange look. She did not say a word at first. My dad was involved in an organization and every month there was a family night. Finally, she spoke, telling me that my dad and the rest of the family were going, but that she was staying home and as the oldest I was tasked with helping her do some things. 

After everyone had left, she asked me to go to the laundry room and get a brown grocery bag on the counter. I did as I was asked, but I peeked inside. There in all its glory was my order. The brightest white slip and panty I had ever seen laying unceremoniously on the top of a small pile in the bag. I carried it to the table and she told me to dump it out. I did as I was instructed. I was probably red as a ripe tomato at this point. To this day it is probably the most degrading and humiliating experience of my life. I have another story later, but this was it, at that point. She asked me what the stuff was for and I told her I like to dress up as a woman. She asked how I acquired it and I told her. She asked if I would like to put it on and declined. She said she had not told my dad yet, but she needed to. I asked her not to, but I was told she had no choice. He was my father and he needed to know. She patted my arm and asked how long this had been going on and had I worn her dresses. I said yes and forever. 

Nothing was said after that for several weeks. Then one afternoon when I came home from school, I was told I was going to an appointment. The appointment was with a counselor who then recommended this sort of physical regimen program. The program was designed to make me more manly. The irony being that this was in the 1980s. Aerobics was huge and sexy outfits were the rage. In the same building every evening as we were leaving, women in leotards and tights congregated outside and waited to be picked up. We had to run the gauntlet and I was left envying them every night. This program lasted over a year. My counselor finally informed my parents that I suffered from a mental issue called “gender dysphoria”. I was told electroshock therapy or a combination of pills might ‘’fix” me but could also cause side effects like sterility. Gratefully, my parents decided that I should not be “fixed” in that manner. 

Next, a pastor at our church met with me and my parents. During one of the sessions it was decided that I would participate in a program that would reduce my desire to dress as a woman by burning out that part of me. It was explained like making a cigarette smoker give up on smoking by making them smoke continuously, until they got sick of it. I was to have access to female clothes and wear them all the time. Obviously not around my siblings, but my dad would take the rest of my family out to dinner or to events and I was to dress up and walk around the house or yard until they came home. I was to sleep in night gowns and wear makeup. I believe this was designed to humiliate me and if you are reading this, you already know what happened. One day I felt I was under great stress, someone bumped into me, knocking my books out of my hand and I snapped. I beat the crap out of him and was suspended from school for 2 weeks. At this point both of my parents worked outside of the house, so I was ordered to live as a girl from the moment everyone left until 3pm every day. 

I was told by my mom and dad late into my senior year of high school that they would not pay for college and that I needed to find a job. My dad’s sister had 3 sons and she was about 18 years older than my dad. The family was very vocal about the Vietnam War, and even though my dad was drafted during the Korean War, the family was not inclined to join the military. So, I knew just what to do. I joined up. The first door at the recruiting center was USMC. They were apparently at lunch, so I walked in the Army door and said I am not 18 yet but I need to join up to get away from my family. I served and was discharged honorable under medical conditions due to a broken femur and kneecap sustained in a training exercise. While in the Army I thought I could stop myself, and for a couple of years I did, but the interest never waned. I would often use my weekend passes to go to hotels. I would take my meager paycheck and buy lingerie and clothes and spend time dressed and then toss it out before returning to base. It was a scary time. This was before President Clinton’s “Don’t Ask, Don’t Tell”. I was living a double life that had huge ramifications if I was caught. One time I caught the eye of my Staff Sergeant while in a Fredrick’s of Hollywood and he looked over at me and laughed, “Good for you son. Get some!!!” I smiled back in an equally loud voice, “Get A lot!!! Who AAH!!!” 

As people often do in the military, I got married. She would stay at her family’s house about 45 miles north of us, whenever we were on maneuvers or deployments. When I was going to be home, I often told her I was coming home a day or two late, so I could dress. One time she came home a day early to set up a Welcome Home celebration. I was playing music and didn’t hear the door open. There I was in a wig, fully dressed in a sexy outfit with garter belts and lace topped stockings, all made up like a street walker. Long story short the marriage was over. 

After my discharge in 1997 and because my MOS was in computers and networking I was recruited to work for a company that offered travel and opportunities all over the world. I was in heaven. I was in great shape; I was making good money and I was living in hotels all over the world on someone else’s dime. My 1 then 2 then 3 suitcases were packed with women’s clothes as gear was shipped ahead. By the time I was in my late 30’s I even had flown en’ femme on a few occasions. I had obtained an ID at my local DMV that identified me as a woman. I worked from home about 20-30% of the time and lived alone. I would always volunteer to take calls and projects out of town. I spent over 15 years living like that. My neighbors eventually became aware of my lifestyle due to my Clark Kent/ Superman antics, mostly due to my lack of interaction and the inability to be in two places at the same time proved my undoing. Some of my neighbors would get upset if I spoke to them or their children. Very seldom did someone come by for a little flour or sugar. I did develop some relationships with a few of the wives and we would go shopping and have tea or go see a movie together. Overall, it was a wonderful time in my life. 

 So, flash forward to about 2003. I met a woman at a bar in Orange County that catered to the LGBTQ lifestyle. She was stunning and had a thing for guys in drag. We were married about two years later and had two children within 3 years. We had an amazing time when I was home. I lived as a woman and she treated me as one. After a few years though, she raised concerns about exposing the now toddler and a second baby to my lifestyle. This obviously was a serious concern. I stopped living at home but continued to dress on travel. I was gone for about 4 months overseas, when I returned, she had moved out with the kids and the next day I was served divorce papers. 

I said earlier that I had a very embarrassing moment on par with the first interaction with my mom. Due to this divorce and the ensuing nastiness in court where I was painted as a pervert and sexual deviant, I started to get really angry, and my anger drove me to some self-destructive behavior. I would basically just go out dressed with no thought to context and what I was doing. I went to the beach several times as a girl. I had a boat at the time and more than once went to a lake nearby. I wore swim dresses and tennis shoes or a one-piece swimsuit with a cover up and hot pink water socks. I dropped the boat into the water and a couple of guys noticed me. Being ‘gentlemen’, they came over to offer to help the damsel in distress. They soon realized I was not what they thought and had a great time informing others on the ramp that I was a “sissy faggot”. I ended up getting the boat in the water and stayed out there until a pair of park rangers told me I had to leave the lake. They may have noticed that I was a guy, but I was so stunned it did not matter. I was able to recover the boat without incident and I felt relieved but convicted that from there on out I would just be a woman whenever possible. I went to family court and told the judge my issues and came clean. My ex said because of this I should not be allowed to have my children. The judge awarded me full custody and for the last 4 years I have effectively been a single parent. I can only dress when the kids are at visitation, but they have become my focus. 

So present day, I have a gurl friend that is also a cross dresser. We spend time together when my kids are gone. We have a great time together. I am quite confident in who I am as a person. As Taylor Swift would say “I shake it off” when someone confronts me. I have found some simple truths in my 50 plus years as a crossdresser. One is that women are truly the more powerful gender. A man will practically kill himself and spend his riches to impress a single woman, and a man will act a way or say a thing to his lady that he would never say to his daughter or mother. Many women allow their partners to treat them horribly or close themselves off. My life is drama free. I have learned that femininity is not a bad thing for a guy and that masculinity is not a bad thing as a woman. It is a rare pleasure to be able to experience both cases. I love that I can fix things and do manly stuff, like work on my vehicles or back up a trailer with ease. I also like that I know the difference between pink and fuschia, that a half-slip will keep my dresses from sticking to the back of my thighs or nylons and I especially enjoy the feeling of a cool breeze on my freshly shaved legs. Without the myopia of being a full-on male, I would have thoughts like, “go to a museum to look at art? What a waste of time”. “Sit down and enjoy the sunset? Sure, I’ll do it and not be grateful I did”. As a gurl, I enjoy the beauty of a single rose; I love to sit at art shows and just admire the paint strokes on a canvas; The nuances of color and scents; why this perfume works for her, but not for me. Being a crossdresser does not mean high heels and short dresses. I will go to Publix in flats, stretch pants and a t-shirt with my hair up and I feel just as beautiful as I do in a $1,000 dollar sequin dress, silk stockings and 4’ pumps. It is the femininity of being a lady that makes me feel normal. It is my femininity that gives me peace in my heart. It is my femininity that allows the scales to come off my eyes and see things from a perspective that many others do not. I am not saying do not go out in day glow pink wigs, or short short dresses and extravagant pantyhose. I am not saying if you are a 400-pound ex NFL star with hairy knuckles do not put on a dress. What I am saying is be true to yourself. My only regret after decades of being the person I am is that I wish I had someone tell me this when I was much younger. You are who you are. You can fake it if you want but you will never be happy until you are who you are. 

The power of the internet, the power of social groups where we can meet on or offline; share ideas, makeup tips and gather as a collective is amazing. The movement towards equality for the LGBTQ groups and communities is making great strides. If you are reading this, you are most likely a part of our community in one aspect or another. Don’t be timid. Don’t be ashamed. Be true to yourself. 

 Cris Dresser can be found on Facebook at https://www.facebook.com/cris.dressor