With a small duffel bag hanging over my shoulder, I entered the department store, trying to look as inconspicuous as possible. This wasn't the first time I had undertaken this particular pursuit, but I was still tense, anxious and excited.
It was a summer day, with typical mid-Atlantic humidity. I picked up a shopping cart, feeling uncomfortably hot and sticky. Even in an air-conditioned store, summer days don't mix with wearing a pair of sheer, thigh-high, gartered nylon stockings, and a tight girdle, under men's blue jeans.
I headed first for the men's clothing section, beginning a ritual I had run through dozens of times at this store. I randomly removed several men's dress shirts from the shelves, neatly pressed in their rectangular plastic packaging, and threw them into the cart. Did I plan to buy them? Not on your life. Placing them into the cart amounted to "bearding"... concealing the items I was really in search of.
I passed through the underwear aisle, and obtained a few pairs of men's briefs, along with a couple of sets of white crew socks, just for good measure. I took a deep breath, and ready to once again commence with the pursuit of my fantasy, headed over to the women's apparel area.
That familiar feeling of euphoria overwhelmed me. So many beautiful clothes... and so little time, and so little money. The initial trepidation about being caught looking at women's clothing had long ago passed; I learned that few if any shoppers paid any mind to those around them, being too wrapped up in their own concerns. For a short while, I just wandered the aisles, imagining myself in the various outfits, until I realized that I had come here with a purpose. Then again, I always came here with a purpose, and it never changed much.
I got down to business. I had to pick one, and only one outfit. Decisions, decisions. What look did I want today? Despite the abundance of clothing, the style variance was limited. I longed to be able to carry out this plan in a more upscale store where I could find clothing that was trendy, or elegant, or sensuous, or even slutty. But I knew that this particular store had some unique features that made it perfect for what I wanted to accomplish. And so far, it had served me very, very well.
First of all, there were the shopping carts... an invaluable accessory. They made it possible to carry out my plan without being ogled, or being wrongly suspected of shoplifting. Then, there were the men's and women's fitting rooms... unusually close together, and intermingling of clothes of both genders on the racks of tried-on clothing was commonplace. And finally, there was the men's restroom... in reasonable proximity to the fitting rooms, yet concealed way back in the corner of the store. Few customers were even aware of its existence.
I decided that a cute, demure outfit was the order of the day. I quickly found a mid-length floral print skirt that I fell in love with. It had pink, peach, and light orange flowers on a white background. Looking all around me to make sure no one was looking, I quickly held it up to myself. It came to just above the knee. Perfect. Not too short, but short enough to reveal a good bit of my freshly-shaven legs behind those nylon stockings.
Now it was time to complement the skirt with a top. I love playing mix-and-match. With the hot weather and all, I wondered if it would be appropriate to take a chance and choose a sleeveless top. But I decided against it, figuring it wouldn't flatter me, despite my somewhat slight, five-foot-ten frame.
I selected a nice, tight, short-sleeve pink ribbed top to go with the skirt. Next, it was over to the shoe department. I wear size 10 women's shoes, which means the selection is limited. I almost chose a sexy set of three inch heels with straps, but I glanced at my somewhat conservative outfit and instead went with a white set of pumps with one-and-a-half inch heels. I smiled to myself... the school teacher look. With this attire, I'd appear as if I was on my way to the first day of classes in September.
With my goodies in the cart, casually mixed in with the masculine items, I strolled past the fitting rooms. I stopped outside the men's restroom. Looking around again to make sure the coast was clear, I carefully removed the feminine items from the cart, and entered the men's room.
Inside, I quickly took a glance under the stall doors. There were three adjacent stalls, and in the farthest stall I could see a pair of feet wearing casual brown loafers. I ducked down a little more to get a better view. I could see tan slacks resting about the man's ankles, and above the lowered trousers I caught a glimpse of ebony skin adorned with fine black leg hair. I smiled. I wouldn't have to wait this time. Taking a deep breath, I entered the middle stall and locked the door, hanging my top and skirt on the peg. Then, I put my duffel bag on the floor and opened it up, momentarily placing the pretty white shoes inside.
As is often the case with men drawn to donning feminine attire, the urge first surfaced during my early teen years. I would wait for those precious moments when the rest of the family was out of the house. Then, I would stealthily enter my sister's room and rummage through her closet. Laura was two years older than me. However, she was still a few sizes smaller than I was, and it was a struggle to slip into her clothes. There was even an instance when I tore one of her dresses in attempt to get into it, and I was scared to death that my little secret was on the verge of being discovered. I returned the damaged clothing to its place in the closet, and if Laura ever suspected anything, she never let on.
I also tried on my mother's clothes on occasion, as hers were closer to my size. But I greatly preferred Laura's wardrobe. Her taste was, predictably, more contemporary and age-appropriate. The sort of clothes that I would wear if I was a girl.
I often wondered about this strange fascination of mine. I figured at the time it was solely sex-driven, as these furtive dress-up attempts were almost always accompanied by vigorous masturbation sessions. I chalked it up to typical teenage hormone-driven perversion, and thought I'd outgrow it.
But the freedom and independence that accompanies young adulthood allowed me to explore feminine experimentation much further. I moved out, and got a real job; and soon, women's clothes purchased specifically for me began to take up a part of my closet. It was a hidden part, to be sure; I still had no desire to be found out. I became comfortable with buying women's clothes; on the rare occasions when a store employee made a remark, I replied with, "It's for my girlfriend" or "It's a birthday present for my sister". I experimented with makeup and jewelry, and eventually became quite proficient at dolling myself up. I even ordered a few wigs through the mail.
I started longing for more; dressing up at home, by myself, just wasn't cutting it anymore. I had become aware of a female side of myself that was longing to escape. There was also a simpler, more manageable problem. I found myself constantly returning items of clothing to the store, since I was unable to try them on before buying them. So one day, I decided to just drop my inhibitions and use the fitting rooms in the store. Wearing panties and stockings under my everyday male attire, I nervously entered the store... the store that I would soon be frequenting on almost a daily basis.
My first stop was the shoe department; I selected a few different kinds of sandals and open-toed styles. Next, I decided to focus on dresses, which were harder to fit visually, without actually being tried on. I picked out a few nice sundresses, putting them into a cart, and made my way toward the fitting rooms. There seemed to be more people than usual clustered in the area, and I lost my nerve. This wasn't nearly as easy as I had expected. What to do? Then my eyes found the men's rest room, and I realized that the stalls inside might provide the privacy I needed.
But, I thought, you aren't allowed to bring unpurchased items into the bathroom. I wondered if it was worth the risk. I looked around quickly... then decided to make my move.
A quick peek into the men's room... I didn't see anyone. I momentarily ditched the cart outside the bathroom door. Let's not overdo it, I thought; I grabbed one dress and one pair of shoes. As fast as I could, I ran into the farthest stall, up against the back wall, and fastened the latch on the door. Done! I was relieved that the floor and the rest of the stall were immaculately clean.
I got undressed, feeling much more relaxed. As long as I didn't do this too often, I reasoned, this would be a great way to try on clothes before actually purchasing them. The lack of a mirror bothered me a little, as did the cramped quarters; but it would certainly reduce the amount of clothes I returned after purchasing.
I stood naked in the stall, then slipped on the shoes... a pair of white sandals with ankle straps. I relished the feeling of standing nude in a men's room wearing nothing but women's shoes. I slipped into the sundress, a pretty lavender number which reached down to about mid-thigh. Very sexy in a subtle way, and a nice fit; I decided to buy it. Then, suddenly, something happened that made my entire body tingle with fear and excitement.
I felt a rough, forceful hand rubbing and caressing the lower part of my leg, right above the ankle straps.
.... There is more of this story ...