Jane Brewer asked, “Lee please go shopping with me to the mall, it will be my treat for both of us”. She’s the one who likes shopping and, as a guy, I didn’t find shopping for clothes to be at all exciting, but she knew I would go. I did like going with Jane and her friends shopping as they are attractive and have good taste in clothes. Girls’ clothing is colorful, it feels nice to touch, and varies with the likes of different girls.

Mom was neither surprised that I was asked nor open to going with Jane. Jane and I had looked at dresses for a good part of the morning. A couple of times when she asked if I thought this one or that was beautiful, she had tried some of the same kind of dresses. I told her once that I thought a dress was beautiful, but I wasn’t sure if it was her color. And I agreed on another that I felt was more attractive on her. Jane has pretty legs as well as a nice figure, though I don’t directly tell her so.

She excused me before she made her final choices. Well, she bought the dress she decided upon and found me again. Then we went to a woman’s shoe store. She was choosing a pretty pair of shoes that had a three-inch heel but wanted my suggestion between one that was black, a pretty red, and a shiny silver pair.

I decided against the black which was a dull black and was torn between red and silver. She asked the saleswoman, “Would you mind if I had him try on a pair of each so I could see how they look?”

I quickly responded, “That’s crazy, it makes no sense.”

Jane told the woman, “When we were trying to decide on dresses; I tried on the two he liked. Don’t you think it would only be fair in him to help me to decide which pair of shoes looks best?”

The salesperson giggled and looked at me, “It’s Lee, isn’t it? She has a point there, it’s only fair. Besides, if I don’t mind you trying on our shoes, you should be willing.”

It was embarrassing to sit and take off my socks. The woman measures my feet, “An eight regular, that is not bad at all. I have both colors in your size.” She left and came back with two boxes of shoes and a pair of footie stockings. She asked me, “Since they’re the same size of shoes, would you like to try one of each at the same time, or should we start with the red pair first?”

Jane said, “I think he should try the red ones first and then the silver shoes.”

I would have rather tried one of each and had it over more quickly. It felt weird to have on these delicate shoes, and their heels changed it even more. I was forced to hold my pant legs up as high as I could. I even needed to walk in them, back and forth. Lastly for each pair, I had to wear them in front of a mirror where I only could see the shoes, my feet, and ankles.

By the time I was trying on the silver shoes, there were six women and two younger girls watching me. One girl said, “Mommy, I’m surprised they look pretty on him. What do you think?”

The woman only responded, “Yes, but shush.”

I asked Jane, “What kind of event are they for?”

Jane said, “It is a special surprise party. There will be dancing and it will be quite fancy as you saw with the dresses we were looking at.”

I said, “Then without a doubt, I suggest you go with the silver pair.” We even chose a special pair of fine stockings to go with them.

Next, we had gone to Victoria’s Secret, but Jane decided it was too busy. We chose to get something to eat at the food court, while the lines there were still somewhat short. We got two entrées plus rice at the Oriental Wok and shared. I got tea and she got water. We both got a fortune cookie. Her cookie gave lottery numbers, mine said, “Something beautiful comes your way.”

I commented that mine should have been for her. She commented, “Don’t you think things can be beautiful for a boy as well?” Not wanting an argument I agreed quietly.

We had walked around and looked at some guy clothes for me, but even Jane agreed that the time spent was as boring as the clothes we looked at. I didn’t want any of it.

It was now about two in the afternoon and the mall was slow, not much business. Jane said, “We should go back to Victoria’s Secret and hope the better of the salespeople are there.”

I joke about how important could the salesperson be. She said, “Don’t laugh, they are more important than you think. Tell me later if you think I’m wrong.”

Jane smiles and tells me, “We’re looking for a panty and a bra set, maybe two. What do you think?”

I told her, “My mother once, and said guys had no place being the ones to decide about these things. Because what looks good to them may not feel good to the person wearing them.”

She said, “I still want you to say what looks pretty. I and the salesperson will make sure they feel comfortable.”

I corrected her English, “It’s the salesperson and me who will make sure they’re comfortable.”

Jane smiles, “You are so correct.”

Once we decided on four different sets of bras and panties. She looks around and called to a college girl that we both knew, “Serena could, you help us. He needs some help in making sure we have the right sizes and fit. He agrees with me comfort is as important as being pretty.”

Serena says, “You two come over here. I probably should have you with me Jane to make sure everything is proper.” We go to a room that at best is eight by six and there is another smaller screened area maybe three by three.

She hands one bra and panty set to me, “Now go in there undress and try these on.”

“No, you have it wrong, these are for Jane,” I said.

Serena said, “Didn’t you hear properly, she said, 'he' needs your help?”

I turned to Jane and she was shaking her head yes. I say, “But I’m a boy.”

Serena says, “Lee, you’re a delicate boy and were nice enough to come shopping. You’ve come this far, you must be tantalized a little, no? Maybe this is part of the surprise.”

I turn to Jane and she nods yes and encourages me. “Please just try them; I even have the dress to wear over them.” She lifts the plastic covering over a dress and it is a beautiful dress with colors that I didn’t think were best for Jane. “These colors are your colors,” she said. My silence was convicting. I wanted and knew I should just say no.

I was overwhelmed with emotions and stepped into the small changing space. I tucked my small boy parts away and the panty looked smooth and flat. I called out The pretty bra wasn’t needed as there was nothing to hold.

Serena slipped open the curtain a little and inserted some cutlets in the cups. Jane asked me to step out when I was done, despite being embarrassed. Serene had a long camisole with spaghetti straps with a lace skirt. Would it make any difference with the dress, ‘my dress?’ The camisole was soon on; as Serena brushed out my hair. There was a long mirror and I saw the image of a young girl that excited me. I brought a hand to my lips. I pouted.

“Let me help,” said Jane, as she used to tube of lipstick to line my lips and to fill them out fully. I teared in amazement. The dress was soon put on over everything and I was transformed into the girl looking from the mirror.

The curtain out to the store was open and I walked out to a three-fold mirror, where I found myself standing on my toes as if I were wearing heels. Serene asked, “How do your panties and bra feel?”

I responded, “Everything is amazing, but it’s wrong I’m a boy.”

Three girls nearby, one saying, “You’re astounding girl or boy.” The compliment sends a tingling sensation through me. I headed back into the protection of the changing room.

“Lela turn and smile,” says Jane, and I did as she took pictures. “One’s to your mother and one’s to Aubrey,” her sister. Jane said, “Aubrey wants me as a bridesmaid, but said she had a bridesmaid who has backed out. I suggested you.”

I said strongly, “And you’ve tried to sabotage me, but my mother will say no.”

Jane said, “Your mother said, you could do it if I could talk you into it.”

“So this was planned,” I asked?

Jane said, “You’re one of my best friends, it came as a natural thought. Just think of how everything worked out right today. You’re the one who walked out to those mirrors and declared everything is amazing.”

Serena asks, “Would you be willing to put on a pair of silk stockings if I were to give them to you?”

I said, “She already bought a pair of 3” heels and special stockings that I suspect are for me, but there’s no way I’m now walking around in 3” heels.”

“We happen to have a pair of two-inch mules that you could use,” said Serena. “I know the perfect pair of stockings, let me get them and the shoes.”

She left for a moment and I sat on a stool, “Jane, how did I allow you to talk me into this?” I was ready to tear again, and she gave me a delicate handkerchief.

“It sounded insane to me when I first thought of it,” she said, “but you’re such a friend I thought that it fit the situation. When I mentioned it to Aubrey, she said you’d be a natural.” And she wondered to me if it might work. She and I asked your mother, who first giggled and said, “He’d be good at it if you could talk him into it.”

Serena was soon back with the stockings and ankle boots with an unusual heel. The white stockings covered the delicate hairs of my legs. Serena started at the tips of my toes and rolled them up. My legs were sensitive to her fingers and the stockings rolling up my legs. I couldn’t believe how far up under the skirt of my dress she took them and made sure they were smooth. She gently pulled down and smoothed out my skirt. Then she helped me into the ankle boots.

She and Jane wanted to help me up, but I shunned them away and inched forward in my seat before standing. I again walked out of the changing room to the same mirrors. They were not my usual steps, but shorter, and my heels hit just before my toes. I turned and looked into the mirrors as though I knew what I was doing. I did like what I saw.

Jane handed me her long strapped purse and the straps were soon over my shoulder and I was holding the purse at my side.

I was buying two sets of bras and panties, the chicklet forms, the long camisole slip, and a pack of everyday panties. Serena helped with some eye makeup and we were done.

Once back into the fitting room, Jane produced another skirt and blouse that I was to wear home, with a pair of flats. Once we left Victoria’s I expected everyone to look at me and point. People looked, but Victoria's Secret bag seemingly explained everything…

To be continued