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steffie -> RE: Cross dressing -- help please (5/6/2008 10:49:33 PM)
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When i was 21, the first person i ever told i wanted to dress like a girl was a Woman twice my age named Marlena. Her reaction was priceless, something i'll never forget. She smiled and said, "Let's go shopping!"
She took me to a woman's boutique where she told me we were going to pick out my first dress. I can remember being extremely nervous. Why couldn't we just shop through catalogs? Why couldn't i just wear something of hers?
She just grinned at me and began holding dresses up against me, trying to figure out my size. Just that simple act alone, had me blushing, as there were several other women shoppers in the aisles.
The more embarrassed I became, the more Marlena loved it.
"I want you to try a few things on," she said.
"You can't be serious?!"
I didn't think they would let me, but Marlena boldly went right up to the two women at the cash register and asked them if it would be all right if I used a dressing room to try a few things on. I was dying. But the women said it was fine.
The next thing i know i'm in the changing booth with Marlena, and she orders me to strip down to the pair of panties I had on under my boy clothes. Then she started handing me the various dresses she'd picked out. None of which seemed to fit right.
"I'm going to go out and grab a few different sizes. You stay just the way you are," Marlena instructed. "Don't you dare put your clothes on! I'll be right back," she said and left.
So there i am, half naked, in just a pair of women's red panties, in a woman's changing booth, listening to the women in the booths around me, and moms with the daughters trying on clothes. I was trembling i was so nervous.
Eventually Marlena returned - and to my great surprise - she brought one of the sales women with her! An attractive 30something year old woman wearing a smart business suit with a knee length skirt and a measuring tape around her neck.
"I want to get your measurements so we can figure out your size," Marlena said grinning. I must have been turning every shade of red in the crayon box. I stood there trying to hide the fact that i was wearing women's panties with my hands.
The sales woman seemed amused, but unfazed. "It's all right," she said, "We get men shopping in here all the time." She told me to raise my arms and fit the measuring tape around my chest... waist... and hips. I was so nervous, my entire body was shaking. I was scared to death that i would get an erection when she held the measuring tape over my crotch - but thankfully, i didn't.
The women discussed my measurements and declared i was a size 10. Smiling sweetly, enjoying my discomfort immensely, Marlena disappeared once more and returned with an armload of size 10 dresses for me to try on. We eventually settled on a cute black cocktail dress. The first of many that i would buy over the years.
That night i got dressed fully as a woman for the first time. Back then my hair was short, and Marlena gave me one of her wigs to wear. She did my makeup. I put on my first pair of pantyhose. Clip-on earrings. The whole 9 yards.
Marlena insisted that i wait to see myself in the mirror until i was completely dressed. When she finally did let me see myself in the full-length mirror behind her closet door, it really knocked my socks off. I felt like i was seeing the twin sister of my soul. Like i was seeing my true self for the first time.
Marlena had one last surprise up her sleeve. Once i was fully dressed, she said, "Let's go out for a while."
No way! The thought of going out in public fully dressed that way, in a little black dress, in my first pair of heels scared me to death. I could hardly walk. The 3" heels felt like stilts. I would have been content to sit in front of the mirror all night. But Marlena insisted. "We'll just go out for a drive."
Which is all we did. We just drove around the city for an hour. To me, it was like an hour long thrill ride on a roller coaster. Every time we'd stop at a red light and another car pulled along side us, i sank down into my seat and tried to hide. All of which had Marlena laughing. She was enjoying my confusion and embarrassment so much, just to work my nerves further, she drove through a McDonald's drive-through window. She loved watching me squirm.
That was my "first time." Nothing sexual to it. But it was a day I'll never forget as long as I live.
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