There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary thing for little more than the thrill of it.

The next group that they describe are interested in emulating the female persona but again only in a temporary manner. These people will make a concerted effort to “pass” when dressed but will maintain primarily their male person. They often shave and will wear makeup to enhance their appearance. Some may have longer hair or a feminine hair style but most still use wigs. They will have some sort of breast enhancement to complete the female form as well. It can vary from simple to actual forms to give them this look.

Last of these groups are what they consider people who are or likely to be moving towards complete transition. They dress mainly in a feminine style daily. They will go to far lengths to improve their feminine appearance. The effort is to not only present and pass as female but to be accepted as such. Many of these people are planning or have begun the process of transition with the intent of complete sexual reassignment as their end goal. Others have moved to this point and chosen to maintain this place with no intention of progression. This group is most commonly associated with the intent of maintaining the most feminine persona possible.

Now I took the time for this for a reason. I have heard of people who have said they could simply give it up. Some have and others, the attempt to has caused a great deal of issues for them. The ones who could and have likely were in the first or just barely in the second groups. However, most fall well into the second or even the third. I have heard of the stories where people have purged several times. Then, after a purge, it was generally only a few weeks before the need had them slowly but very surely rebuilding their former wardrobe. I have often wondered how much money these people pump into the economy every year? I am sure the amount would surprise most of us. I can tell you I have done it three different times.

What is important to remember is that it isn’t just a few items of clothing we are talking about. For people in deep into the second group, this would mean realistic breast forms and quality wigs. Extensive wardrobes including shoes and accessories. These people often have built their collections large enough to point out that they can fill a closet and dresser.

To tell you about me I have to say my story starts pretty typical of nearly every single one of us. In my case, my sister was three years younger so I began my “experimenting” with my mother’s items. I would try my look every chance I got when I was home alone. About a year later, I even began to try make up. I don’t have to tell anyone that those early attempts were what I would have called my “clown” time. As I got older and began to earn my own money I stopped using her things and bought my own. My collection was small, very small, but it was mine.

Now, it wasn’t like my family encouraged this, quite the opposite. Over the next five years, I was given the chance to speak with at least four different shrinks to be “fixed” of my “problem”. They never actually caught me but got close enough several times for me to experience this opportunity. Now it wasn’t all bad. I developed a skill that has done me well. I learned to read people and get an idea of what they were thinking before they said anything. I also got very good at controlling a conversation, only giving enough to keep the dialog and not letting them dig but never anything of real substance. It also drove me deeper into “hiding”. I made sure no one was going to learn about Debra (as I called her). This went on well into my college years.

While in school, I pushed the limit. I would often wear panties to school. In the winter I would wear a cami under my sweat shirt. The heavy material would help to hide the straps. I loved the feeling of being dressed. I began to notice that I did better while taking exams when I did this. It was really hard to explain and if you don’t understand I still can’t find the words to fully explain it. I dressed at home behind locked doors and closed curtains. I got better with makeup and studied women. I would walk and work on my voice and really did all I could to perfect Debra.

In college, I had a decent job that gave me enough money to live in a studio apartment. It was a dream come true. I was able to give Debra even more freedom. Large lecture classes allowed me to hide in plain sight as well. No one really cared and I found that I could venture outside. I could actually give Debra the chance to feel the sun on her face and wind on her legs. My job made it so I could begin there. There were several others that dressed and a few who had moved into transitioning so it was even easier to make the choice to step further, and Debra took it.

Now, I was still temporary. I was still dating girls from time to time and my years of protecting Debra meant I would keep her well hidden from them. I wasn’t remotely interested in men or being with a man. I just knew girls were not going to be interested in Debra. It caused issues for me and, well my relationships generally didn’t last more than a few months. It wasn’t like I avoided physical contact or sexual activity with some of them it was … well honestly it was just not going to work. Looking back I think that Debra had a lot to do with those failed relationships. As crazy as it sounds, I think on some level the drive to give her back her freedom, or her persona, take back that freedom had a lot of influence.

Shortly after I graduated and found a job, I met Tina. She was great and this time the desire for Debra to get her freedom was being crushed. So much so that I did my first real purge. It was huge. Over the past four years, Debra had amassed a substantial wardrobe. High quality breast forms and a natural hair wig. I hated the thought of getting rid of everything I had but I knew it was what I needed to do. In time we got engaged and married. Over the next few years,I had managed to keep Debra gone. I had felt her and her desire to return but I had always managed to keep it locked away.

Let me take this time now to revisit reality. I had mentioned that many people in groups two and three purge multiple times. That no matter what they say or want to believe reality is that many purge several times. The drive is just too strong and in the end the reality is the feminine persona will win every time. This was the case with me as well. Slowly, very slowly, I began to collect new items. I was careful to make sure Tina never knew. I made sure that I only got an item here and there. It was well over a year before I purchased a wig and then several more months before I replaced my breast forms. Little by little, Debra was beginning to win. No matter how I tried she was gaining an advantage.

The downfall of anyone that is trying to hide isn’t the sudden discovery of what they have been trying to hide.

No, it is the little slips. The small errors that begin to give them away. None on their own mean anything. Each so generally small enough that it barely draws attention, however like a puzzle, each piece begins to show a picture. As the picture even shows the slightest view the purge happens again. This way deniability stops the progression of the picture. Taking it all the way back to zero for a period of time. The reality again is that with each purge the time between purge and rebuilding is less. The drive is stronger, the need more. It begins to great an internal struggle that eats at the sole and again “she” wins.

This was the case and finally, I was put into a position where I had to admit everything. I was scared to death but knew that I had no choice. As expected there was the crying and yelling. There were the statements and of course the shrink. I was going to walk away. Even I didn’t know how but I planned on it. After a few weeks, Tina surprised me. She didn’t want me to purge again she said that she supported me and wanted me to pull it all out of hiding and put things away. I was shocked and didn’t know what to say. I hadn’t purged yet and was struggling with the idea of doing yet again, but this was totally off the wall. She insisted that she understood, though not overly supportive. I slowly accepted what she said and a few days later had managed to put things away. The challenge wasn’t getting the clothing and various items out but finding a place for them.

Now, Tina and I both worked at the same company but she went to work about an hour before me. It wasn’t really so bad. We got up at the same time and she got ready and then I did. A lot of the time we rode together and just waited. When overtime was offered it worked great we both could come and leave at the same time and each get an hour of overtime. But for a few days, she would leave right away and meet me at home. I didn’t really know why and she just said she needed to go someplace or get something. It didn’t seem like a big deal so I never really said much.

One morning I discovered what she was doing. We had gone out the night before and got home kinda late so it was straight to bed and get some sleep. The next morning I went to get a pair of under ware when I discovered that I didn’t have any….none. In the drawer we stockings. That was all, just stockings. I checked the next drawer and noticed only bras, panties and camis. The drawers were full too, way more than I had had. I pushed things left and right when she walked in.

Tina asked, “What is wrong?”

“Ah, just looking.” I said.

Tina just kind of smiled and went on, “Well I got you some new things. I figured you need a few more and then figured we didn’t have enough room for that old stuff and got rid of them.” 

Not fully grasping the comment replied, “Really, why?”

Tina with a slight smile replied, “Why not? I mean you like them. You prefer to wear them so why keep the other stuff?”

Now there was no argument there. I honestly didn’t even have a lame excuse for her. It all seemed perfectly normal and made sense to me.

Tina stopped a moment and said, “You do need to fix something, though.” 

I just said, “What?”

Tina looking and sounding serious said, “Well you need to shave… a lot. Actually completely.” 

Still not completely getting it responded, “I do?”

Tina went on saying, “Of course, that or I don’t. In for a penny in for a pound. You can do it this evening.” 

The rest of the day, I thought this through. Again no matter how I tried I didn’t seem to be any reason for me to not do that. Honestly, I had always wanted to but how could I have hidden that? So when I got home she handed me the cream and off to the bathroom I went. The stuff smelled awful and kind of burned a little. When I was done I rubbed the sweet flower-scented lotion on me. It felt cool and soothing. I then went to get dressed and discovered that all my shorts and t-shirts were now gone. I found something to wear and met her in the kitchen.

I looked and Tina and said, “Honey, I can’t find my shorts and shirts.” 

Without missing a beat, she said, “Of course.” 

My only response was, “Of course?”

Tina just went on calmly, “Debra, there is no way a woman would wear those things so I got rid of them. Besides, you look good. Not great but good.” 

The next morning Tina got up and had me get going quick. A quick shower and dressed and out of the house. All she said was we had a lot to do and needed to get going. I hurried and got in the car and before I knew it we were at the salon.

Tina said, “Come on we have appointments.”

I stared at her and said, “We?”

Tina replied, “Yes, we. Don’t worry it will be fine, more than fine.”

The next few hours were more than I was ready for. We both got the full treatment. Make overs, nails the works. When I was done, I was really surprised at how feminine I looked. The scary part was my still male hair style with a very feminine face, hands and toes. Tina came over carrying a bag and I was led off to a small room. With a little help, I attached some very very realistic breast forms. The D-cup forms blended so that there was no obvious way to tell they weren’t real. I got dressed and came back out. Now when I saw myself the only way anyone could tell was the hair style. I was seated again and after a few different tries settled on a dark brown with slight red tint shoulder length natural hair wig. The end result was a woman. To say I passed was an understatement. I would have to “prove” I wasn’t Debra now. I honestly didn’t even recognize myself.

The next stop was lunch and a day of shopping. When we got home I discovered that the only thing male left was me. Nothing I had left was male. I looked through the closet wondering how I was going to go to work or anywhere. Tina just pointed out that given the way I look now I would look stupid trying to dress and look male. Since this was what I always wanted to do I now could easily do it. I could “hide in plain sight”. That I had just spent the entire day in public with hundreds of people seeing me and no one cared. I wanted to protest but it wasn’t going to do much good and given that I only had a feminine wardrobe didn’t matter anyways. The rest of the weekend we went all over so I could get used to Debra being out.

Monday morning I got dressed and made sure my makeup was just right. I chose a basic look for work and took a deep breath as we left the house. The sound of my heels clicking on the pavement was deafening. Everything was intensified as I made my way in and to my desk. I just focused on the work and tried to relax. Over the rest of the day the girls on my team congratulated me on my look and how glad they were I did this. By the time I left work I was relaxed and comfortable with myself. By the end of the week, I felt totally natural and the familiar feeling of peace and contentment was back.

Over the next weeks and months I became more relaxed and more free, I dressed in less “stuffy” manners and more like the rest of the women. I had improved my voice and mannerisms. My hair was now long enough for a cut color and style so the wigs were gone. I had really become Debra on nearly every level.