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Falling in Love Lookbook by Glamour Boutique Feel like a stylish fashionista this Fall!Browse our Falling in Love lookbook for new style inspiration this Fall. You cannot go wrong with any of these beautiful Fall looks. Crafted with CD and transgenders in mind- you will be sure to love the fit and coverage! Another thing […]

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Wearing Alice + Olivia.South Korean pop star Heechul.

My life as Carollyn Olson has been quite a satisfying ride.

Over the last three decades, Carollyn has figuratively flourished and matured, and developed so many great friends. I would not change a thing.

My story is a little different than many of yours. I did not start dressing until 35 years ago and it was very accidental. To make a long story short, I can blame it on the cat.

I was home working on my spouse’s dresser when she was out of town. Our cat decided to jump into a drawer and damaged two pair of nylons. I was going to show them to my spouse and let her throw them away, but for some reason I put them on. Before I knew it, I was dressed in her clothes, wig and shoes. Oh, what a feeling!

By the next weekend, when she was once again away from home, I had bought heels, two dresses, pantyhose, and had studied how my spouse applied her makeup. I completely dressed and went out for the first time. The first time I really looked in the mirror, I could not believe how good I looked.

Where did I go? I drove to the local mall, walked around a bit, went in to a couple of shops, had a bite to eat and sat on a bench to watch other women walk through the mall so I could study their mannerisms and how they walked and talked. Was I nervous? Yes, a bit, but not overly. I was “passing” and enjoying myself. When I look back at that first time today, I still wonder how I did it.

Since then, I try to dress two or three times a month. However, I have had to be careful with my dressing (my wife is unware of my hobby even though she has dressed me twice for Halloween parties).

Wearing Polo.

The first item of women's clothing I ever wore were a pair of my mother's nylon stockings. I recall looking in the floor-length mirror mounted on the inside of her closet door and admiring my pre-puberty hairless legs believing that they looked just like women's legs!

With my mother's closet door wide open, I noticed the stack of shoe boxes on the closet floor and I suddenly felt motivated to try on a pair of her high heel pumps. I opened a random box and found a pair in a floral fabric with a 3-inch heel. I slipped on the heels and they fit perfectly.

I looked in the mirror and the combination of nylons and high heels was exhilarating! Not only did my legs look like women's legs, but now they looked shapely and sexy, too!

I have been a big fan of high heels ever since. When en femme, I seldom wear anything else on my feet. Unless the occasion absolutely screams for flats, I wear heels.

Once upon a time, I thought that at 6-feet-2, wearing heels would make it more difficult to pass. But I came to the realization that if I can pass at 6-foot-2 wearing flats, then I can pass at 6-foot-6 wearing 4-inch heels.

I love wearing heels. They make my legs look more shapely and more importantly, I feel more feminine, more lady-like wearing heels. I know it’s my late-1950s/early-1960s socialization that makes me feel this way, but that's me and I'm not changing shoe styles at this late date.

Genetic females often compliment me about my proficiency in walking in heels and ask if it was difficult learning how. Truth is that I took to heels like Daisy Duck took to heels.

As a child, my mother often mentioned that I walked on my tiptoes. I assumed that walking on my tiptoes was not the way a male was supposed to walk, but nobody ever taught me the "correct" way to walk. So I took the path of least resistance and continued to walk on my tiptoes.

I believe that my penchant for walking on my tiptoes made walking in high heels a natural thing to do. True or not, from day one, I never had a problem walking in heels.

Heels hurt. I have high heels that begin hurting as soon as I slip them on and I have heels that I can wear all day with little or no pain. I discovered that the height of the heel is not critical as far as pain is concerned. Some of my most comfortable shoes have 4-inch stiletto heels. Go figure!

Wearing heels makes my femulation complete. Despite the pain, I will never give up wearing heels; you will have to remove my high heels from my cold, dead feet.

Wearing Miguelina Camelia top and skirt and Rag & Bone hat.

Roger Sloman femulates in British television's Eastenders. (Thank you, Meg, for suggesting this femulator!)

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I left my friend Dan’s house after finding this coin in his basement. Personally, I didn’t think
much of it. I mean, yeah, it was old so it might of had some value to it but for some reason
Dan seemed to think that this was something much more.

I left him to do his research so that I could get home in time for dinner. I must have been
walking for a good few minutes when I suddenly felt lll. With not much further to go, I ran
home and headed straight for the bathroom.

Why do you love to crossdress? Here is why WE love it..