tagReviews & EssaysFreddie Becomes a Cross-Dresser Ch. 01

Freddie Becomes a Cross-Dresser Ch. 01


I was determined to write a transsexual and/or cross-dressing story for Literotica's 2008 Survivor Contest. I thought that I had written a cross-dressing story when I wrote Do You Know A Cross-Dresser, Ch. 02, but that was placed in the Reviews and Essays Category. Then, I thought that I had written a transsexual story when I wrote Transsexual Sex with Vinnie and James, but that too was switched from the intended category and placed in the Non-Erotic Category. Nonetheless, it is what it is only now, I'm in a quandary. It is very perplexing trying to think what to write that will not be switched to another category.

Then, I decided, that maybe I need to realize and develop the character of the story more. I need to feel what it is like to be a cross-dresser and not just write about a cross-dresser. Gulp. I need to become a cross-dresser. If that's what I have to do to have a story posted in the Transsexual & Cross-dresser category, then, by golly, that's what I'll do. I'll become a cross-dresser. I'll cross-dress and then write the story. Suddenly, I felt as I was one with the universe.

Since I have no idea what it's like to be a transsexual nor do I want to start taking estrogen supplements just to write a story about transsexuals, I decided to do a bit of research and see what it is like to cross-dress. Now, I watched enough of Jerry Springer to know something about transsexuals and cross-dressers. Not all transsexuals have sex with men and to further confuse the issue, there are some cross-dressers who have sex with men. In any event, no men's cocks but mine and by women, will be sucked in this story.

Nonetheless, first on the list was to go shopping in a women's clothing store. Now, since I'm a big guy, I figured the best bet was to find one of those full figured women's stores. There's no way that junior miss or petite clothes would fit my muscular frame.

Never having had to shop for women's clothes before, I pulled out the yellow pages to find a full figured women's store. Let's see, Big and Beautiful, Clothes for Real Women, Designers Dresses for Dieters, Emma's Ensembles, Fat But Feminine, and there, perfect, the store with the biggest ad in the full figured women's section was the Full Figured Women's Clothing Store, of course. It pays to have name recognition.

I drove to the mall and parked my car away from the other cars. I felt as if I was doing something wrong, something illegal, in buying women's clothes for myself. There's no law against doing that, is there?

"Why am I under arrest? What are the charges, officer?"

"Well, the way that you look wearing women's clothes, Freddie, there just has to be a law against it. I figure that I'll take you in for protective custody for the time being and have the district attorney deal with you."

"Do I look that bad, officer?"

The officer stopped laughing long enough to describe how I looked.

"Do you remember when Dennis Rodman wore a wedding dress to marry Carmen Elektra?"


"Well, you make him look beautiful."

"Okay, then, you'd better take me in and get me off the streets for my own good."

The feeling that I was doing something wrong by shopping for women's clothes for myself gave me a bit of insight as to what a real cross-dresser must go through to buy clothes for himself. Sure, it's probably easier for him if he wears the same sizes as his wife, girlfriend or mother. Yet, what about those guys who live alone after their wives, girlfriends or mothers discovered their need to wear women's clothes and divorced them or threw them out of their homes? Now, they are on their own having to somehow buy their own wardrobe. Yet, there are some women who know about their husband's or boyfriend's need to wear women's clothes and they not only embrace it but also help them to shop for their wardrobe. That's another insight for me to record in my notebook.

This is good. This is working. I'm gaining some real insight into what it's like to be a cross-dresser. I pulled out my pad of paper and wrote the insights that I just realized about the difficulty that cross-dressers must experience when shopping for clothes. Then, I thought, maybe not all cross-dressers experience stress when shopping for clothes. Maybe, they enjoy it. Moreover, with the Internet, they can just shop online in the privacy of their own homes and return it if it doesn't fit. At that point, I wanted to go home and shop online. At that point, I just wanted to go home and write my cross-dresser story. Nonetheless, I persevered. I got out of the car and walked to the store.

As soon as I entered the store, I wanted to flee. I was paranoid. I felt as though all eyes were upon me and everyone knew why I was there. I felt like people were pointing and whispering about me. I felt like a criminal. I felt like a shoplifter. I imagined women talking about me.

"Do you see that guy?"

"Which guy?"

"Which guy? There's only one guy in the store."

"Oh, are you talking about that handsome, masculine, muscular, and modest man with the huge bulge in his pants who is now looking over at us sheepishly because he thinks we are talking about him and, of course, we are?"

"Yeah, that's the one."

"What about him? He's very cute. I wonder if he's single."

"I think he's a cross-dresser."

"Cross-dresser? Him? No way."

"Then, why else would he be shopping in the Full Figured Women's Clothing Store?"

"Duh, maybe he's buying clothes for his wife, girlfriend or mother."

"Yeah, you're probably right."

Okay, good, that's another insight. I pulled out my notebook and wrote how paranoid I felt in thinking that everyone was staring at me and whispering their suspicions that I was a cross-dresser. This is good, this is really good. Again, I wanted to leave and return home to write my cross-dressing story. I'm just glad that I decided to research cross-dressers and not transsexuals. Shit, I have to be careful with my comments. I don't want to make this story too funny because then the powers at Literotica will put this story in the humor category instead of the cross-dressing category.

To be continued...

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