tagReviews & EssaysFreddie Becomes a Cross-Dresser Ch. 04

Freddie Becomes a Cross-Dresser Ch. 04


Now, that I bought everything that I needed to transform myself from a handsome and modest man to a beautiful and sexy woman, I realized that I had completed the easy part in buying the clothes, the makeup, and the perfume. The difficult part, of course, would be dressing up like a woman without having a woman there to help me. I certainly did not want to ask my girlfriend for help. I can just imagine the conversation we would have asking for her to help me dress.

"Honey, I can't hook my bra. Can you give me a hand?" Oh, yeah, that would go over big.

"Sorry, Freddie, I don't have time to help you with your bra because I'm off on a date with a man who doesn't need to dress like a woman. The only help I'm going to give a man tonight is not to dress him, but to undress him when I remove his underwear."

The hard part was yet to come, stepping outside while wearing women's clothes. How would people react to seeing me dressed as a woman? Would they know that I'm a man? Would they know that I'm a cross-dresser? Would they recognize that I'm Freddie?

I figured knowing that I was a man dressed as a woman would lessen my confidence for me to play the part of a woman. I had to feel confident, sexy, and pretty in who I was to pull it off.

I decided that the day for the unveiling was Tuesday. For some unknown reason, I figured there would be less people out and about that day. Don't ask me why. I have no idea.

I took a day off from work, showered, shaved my face real close using a new blade and shaved my legs, arms, and even hands and fingers. I never even considered shaving the hair off my hands and fingers until I shaved the hair off my arms. I didn't have a choice. The hair on my hands and fingers stuck out. I even tweezed my eyebrows.

"Ouch! Ouch! Ouch!"

Gees, women are nuts to go through all of this shit. I was cross-eyed just putting on eye makeup. I have to admit, though, my eyes did look nice when I was done. Not bad for a first time. Gees, what the Hell am I saying, as if there will be a next time.

When I think of all the times I made my girlfriend wear lipstick because I love kissing her with lipstick, and now that I am wearing it, I hate not only how it feels but also how it looks. It took me three tries before I applied it straight. Without even having to look in the mirror, she makes it look so easy when she puts it on her lips.

I'm glad that I bought an extra pair of pantyhose because I put a big run in the first pair with my toenails. I stopped to trim my toenails before putting on the next pair of pantyhose.

Normally, it takes me half an hour to shower, shave, and dress. Three hours later, I was still not completely ready. Now, I know why I'm always waiting for my girlfriend to get ready. It's funny how a little bit of insight changes your attitude towards things. Suddenly, the old adage about walk a mile in my shoes made me realize how much my feet hurt wearing these woman's flats.

Fortunately, my girlfriend had a wig for me to wear that her mother wore when she had cancer and lost all her hair from chemotherapy. I used that for my hair. Yeah, I know, it grossed me out a bit, too, to use my girlfriend's dead mother's wig. Only, I forgot about needing a wig, never even thought about it until it was too late. Please don't tell my girlfriend. She'll really think me weird.

I thought that I had taken care of everything, dress, shoes, purse, slip, bra, panties, pantyhose, makeup, and perfume. I never even thought about a wig. I suspect in the back of my mind that I was just going to wear my Patriots or Red Sox baseball cap (lol) with my dress. Wearing this wig felt like I was wearing my big raccoon hat.

I pulled out my notebook to record my appreciation for what a woman must go through on a daily basis to ready herself for work, to go shopping or just to go out. If I had to do this everyday, I'd never leave my house. Suddenly, looking at how I looked in the mirror dressed as a woman, I thought of a man asking me for sex and got a headache. That was an epiphany to realize that about women. Fortunately, I can remove all of this and return to my masculine self, whereas, women are stuck with themselves. Truly, I'm glad I'm a man.

Finally, nearly noontime and I was ready to take my first steps out in public. I stood by the front door to make sure no one was around and peered out the window. Shit, here comes the mailman. Boy that was close. I'll just wait until he goes by. I used the time waiting for him to deliver my mail to practice my voice.

"Hello, how are you?"

I tried making my voice higher.

"Hello, how are you?"

My voice still sounded too much like a guy.

"My name? My name is..."

Well, that's a good question. What is my name?"

I decided on Frederica, just incase someone recognized me and called me Freddie. That way, I can still stay in my role as...a man who looks nothing at all like a woman. My God look at me. I'm freakish. I turned from side to side looking at myself in the mirror. I look ridiculous. I need to put more powder on my face because I can still see stubble.

Nonetheless, since I've always subscribed to the premise that you can only write what you know, I had to go through with this. I had to know what a cross-dresser feels when he walks out in public. I needed to write my cross-dressing story and the only way that I can write it is to experience what it's really like to be a cross-dresser.

Now, that I was dressed and ready to venture outside, I thought that the difficult part was behind me, buying all that I needed and getting myself dressed and ready. I was wrong. The hardest part of this entire experience was opening my front door. I couldn't. My hand was frozen on the doorknob. I was afraid. I was having a panic attack. This was real, now. Either I was going to do it or chicken out and not go through with it.

That was when I realized the missing piece that made me unable to feel what a cross-dresser feels and that is the part that I really needed to write my story. I needed to know what these men felt before, during, and after dressing and acting like women. I needed to feel what they felt when they bought these clothes and how they felt about themselves after they were dressed?

Did they feel freakish the way that I feel now, probably not, otherwise they wouldn't do it? Did they feel compelled to do it and tortured when they did it? It's one thing to think about dressing as a woman, but it is totally another thing to actually go through with it. I have no idea what their thought process is like to make them want to do it. Did they feel pretty or desirable before and bad about it later?

I started to perspire. I could feel my heart pounding. What if someone saw me and recognized me? What would I say? I know, I'll tell them that I lost a bet on the Super Bowl and this is my punishment for the New York Giants beating the New England Patriots. Okay, now I felt a bit better about going outside. I was still nervous as Hell though.

I opened the door and walked outside.

To be continued..

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