tagReviews & EssaysFreddie Becomes a Cross-Dresser Ch. 02

Freddie Becomes a Cross-Dresser Ch. 02


I walked in the store and continued over to an area where there weren't too many women. Even though I wanted to cheat and buy a pair of jeans, I figured that I'd have to wear a dress to experience the real effects of cross-dressing. There, that's another insight. Cross-dressers probably, I'm thinking as I wrote my thoughts in my notebook, would rather wear dresses than pants or jeans. Fuck, just as I thought that, I thought that I'd have to wear pantyhose and, damn it, shave my legs and, if I wear short sleeves, my arms, too. Oh, mother of God.

Now, I really wanted to return home and just write my story. Yet, in fairness to all of those brave men who have gone before me, who worn a dress for laughs, for their art, to make a movie that have entertained so many of us, I persevered.

I thought of Tony Curtis playing Josephine and Jack Lemmon playing Daphne in Some Like It Hot. I thought of Dustin Hoffman playing Dorothy Michaels in Tootsie. I thought of the ever so hairy Robin Williams playing Euphenginia Doubtfire in Mrs. Doubtfire. Finally, with the thought of John Travolta, who once played the beloved character of Vinnie Barbarino, now emasculated to playing Edna Turnblad, Christopher Walken's wife in Hairspray in mind, I persevered.

Suddenly, I started getting into the fashion sense of buying a dress, but not just any dress. I wanted the dress. I wanted that dress that made me look good and that made me look not only hot and but also desirable to men. Desirable to men? What the Hell is wrong with me? There, another insight. I pulled out my notebook and wrote it down as quickly as I could. Nonetheless, I wanted a dress that flattered my figure and downplayed my waist while showing off my bust and highlighted my hips.

I looked at hemlines, short skirts, above the knee, below the knee, and long dresses. Button dresses, zippered backs, puffy sleeved, short sleeved, long sleeved, flared skirts, pleated skirts, tweeds, plaids, prints, stripes, and polka dots. Then, I found this navy blue dress that was just stunning. I held it up to the mirror, looked down at the price, and it was on sale. I was so happy. Gees, I think that I like this cross-dressing a bit too much. I pulled out my notebook and wrote that insight down, too.

I figured there was no way that I'd be able to try it on in the dressing room, another insight. Cross-dressers are unable to try on their purchases, I wrote in my notebook of researched facts. Well, maybe there are some cross-dressers who don't care if anyone knows they are cross-dressers and will try the garment on anyway. I figured that would work if there are separate dressing rooms with doors, but would never work if they had to walk through an area where other women were changing their clothes. Boy, just that image of being able to spy on women changing would want me to make believe that I was a cross-dresser. I'll have to remember that when I write a voyeur and exhibitionism story.

When I held the dress up to my body and looked at it in the mirror, there was a guy with his wife or girlfriend staring over at me. He smiled and gave me an approving nod. That was when I realized that he, too, may be a closet cross-dresser or maybe he likes men who cross-dress. Suddenly, Jerry Springer loomed before me.

"Our next guest is Freddie, who never was a cross-dresser until he decided to research a story on cross-dressing. He's married to Gary, who he met at the store while shopping. Gary has a fetish and an attraction for men who cross-dress."

I turned to him with the dress held up to my neck and with raised eyebrows asked his opinion without speaking. He gave me the thumbs up sign.

"Pardon me," I said. "Your name isn't Gary, by chance, is it?"

"No, it's Joel," he said turning away to find his wife or girlfriend.

After he left, I pulled out my notebook and wrote that insight about him helping me to select my dress. Unbelievably, a few minutes later, he appeared from nowhere with a matching navy blue handbag. It was perfect and had plenty of room for my makeup and perfume. Shit! Makeup and perfume, I have to buy that, too.

"Thank you, Joel."

He slipped me a piece of paper with a telephone number. I looked up at him and he raised his hand to his ear and mouthed the words as he left, "call me."


Now, I just needed to find shoes. Suddenly, I had a vision of myself trying to walk in high heels, breaking a heel, falling, hitting my head on the sidewalk, and being rushed to the hospital emergency room where my girlfriend works as an admitting nurse.

"Oh, hi, Hon."

"Tell me, Freddie, that you were on your way to a masquerade party without me or you were trying on clothes that you were buying for your mother?"

"Uhm, would you believe me if I told you that I was doing research for my cross-dressing story that I was writing for Literotica?"

"Unfortunately for me, but fortunately for you, yes."

With that vision of having a high-heel accident in mind, I decided to bypass the heels, forget the pumps, and buy flats. I found these navy blue flats that were just darling. Only, these were a size 7 and I needed a size 12, at least. I walked to the next aisle over where they had the gunboat shoe sizes. Women who have feet this big would never be blown over in a windstorm.

I found a pair that looked long enough, but they appeared a bit narrow. No wonder why women have so many pair of shoes, they can't wear any of them long enough because they are all so uncomfortable. I shoehorned them on my big feet.

Just as I was trying them on, a woman came around the corner holding her child by his hand. She covered his eyes, made a face at me, and scurried away. That was when I figured that she had just made her son a cross-dresser. Okay, maybe not true, but it was insight enough for the purpose of my story.

Now, with dress, handbag, and shoes, but still having to stop somewhere to buy makeup and perfume, I was ready to hit the checkout counter. Only, I had this nagging feeling that I was forgetting something when suddenly, the image of me walking down the Victoria Secret runway wearing a Wonder bra, thong panties, and a pair of angel wings made my stomach turn. Shit. I was forgetting the underwear, panties, bra, slip, and pantyhose.

To be continued...

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