16 year old Darren Peterman goes shopping with his mom at the mall as a woman. Later that day, he meets his father while wearing his "older woman" make-up for the first time.

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Chapter 6
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By the time Mom and I walked into Lord and Taylor, I had forgotten all about my eyebrows. I was in awe of my situation and surrounds and I was eagerly anticipating the day of shopping ahead. I mean, there are hundreds of department stores, but there is only one store like Lord and Taylor and that's Lord and Taylor! The store and its selections oozed feminine style, sophistication, and maturity, which was everything I wanted to emulate.

It took less than fifteen minutes for me to appreciate the overwhelming nature of our shopping task. "How long does the store stay opene, Mom?" I whispered, not yet trusting my faux-female voice.

"I know we had fun with that creepy guy at the gaff store, but from now on, you need to call me 'Karen' from now on," she replied, removed a pair of black slacks from a rack. Then she smiled gently as she saw my embarrassment at my mistake. "Don't worry, I don't think anyone heard you. We'll work on your voice over the next couple of weeks." She held the slacks against my padded body to see how they'd look on me. "I'm pretty sure these will fit, and look great, but you'll still need to try them on. And, since you asked, the store closes at nine o'clock, sweetie, the same as the mall."

We couldn't buy a complete upscale middle-aged woman's wardrobe for me in one shopping excursion, so Mom planned to purchase clothes that could be mixed and matched to create a variety of different outfits for any occasion. Granted, it's not rocket science, but I was still in awe of how she explained how this blouse would go with that skirt or how a pair of pants could go with the same blouse and with the right shoes, could make an entirely different look. I loved it.

Personally speaking, though, I like dresses the best and couldn't wait to see one over my false curves. Mom promised to buy me one or two, but she assured me I'd have more use for skirts and slacks and jackets and blouses. Better to mix pieces to create different outfits, she reminded me. I trusted her judgment, letting her experienced eye pick out my clothes.

She set me up with everything I needed from top to bottom. Undergarments from bras to girdles to slips, the mix-and-match outfits, several pairs of shoes and boots in my size along with expensive makeup and perfume.

One thing that surprised me during our trip was that I gained more of an appreciation for women's jeans - not because I particularly like jeans, but because they go so well with sweaters. I figured with the right padding on my hips and butt and breasts, the jeans and sweaters would make me look like any woman my mother's age.

We'd been shopping for about two hours when my mother started complaining that she was long overdue for a cigarette break. She suggested we pay for everything and stow them in the car before lunch.

On the way to the check out, I saw a display of Christmas-themed sweatshirts. I know they're unbelievably tacky, with their sewn on cartoons and bells, but they absolutely scream housewife and mother. Have you ever known a middle-aged woman who doesn't have at least one of these tacky seasonal sweat shirts?

"You like those. Don't you?" Mom asked as I caressed the sleeve of one. It was bright red with a reindeer cartoon sewn on the front with a jingle bell on its nose.

"It's kind of embarrassing, but yes. I love it," I said. "It reminds me of you at Christmas."

Mom smiled warmly. "So you wouldn't be embarrassed to run around town with it on? With that bell dangling and jingling from your breasts, people would hear you for miles around," she said.

"I know," I said excitedly. "Wouldn't that be cool?"

"Yes, it would be," she replied as she found the same sweater in my size and handed it to me. "Now you can look like a Christmas mother," she said as we got in line for the check out.

****

After putting our shopping bags in the back seat of her Mercedes, Mom told me she was going to start the car and have a cigarette. "It's too cold to stand out there and smoke," she said.

I didn't really feel like I needed a cigarette but I wasn't going to pass up a chance to smoke with my mom as an adult and an equal.

"How do your lungs feel?" Mom asked.

I lit my cigarette and inhaled without coughing. "Miserable," I said.

"I bet they do," she said. "That's their way of telling you to stop before it's too late."

I told her that I didn't want to stop.

"I know you don't," she said, "and I don't expect you to. I'm sure you'll probably have a pack a day habit by the end of the week. And by the end of summer, who knows? You'll probably be up to three packs a day like me and my friends."

The thought of smoking as much as my mom and her friends aroused me but my newly installed gaffe prevented me from expressing it.

"Karen, I was wondering. Do you really enjoy smoking? You know. Like does it really feel good to you?"

"First of all, I want to thank you for calling me by my name," she said, "and secondly, I'm not going to lie to you. I enjoy smoking very much and so will you some day. But it's not always like that. I'm constantly getting chest infections and bronchitis and that's because I'm a smoker. When I'm sick like that it hurts to smoke, but it hurts worse when I don't. And even when I'm not sick, I get so out of breath from just simplest things, like walking around this mall. I know you don't believe me yet, but you're going to feel it when you go to practice on Monday. It's going to be a small preview of what you can expect from being a smoker."

****

Mom and I arrived back home sometime before ten o'clock. It was late and we were tired. Sammy had gone to bed hours before but my dad was waiting for us in the living room.

It was the first time my father had seen me with my older woman make-up on and he was astounded to say the least.

"Darren! Is that really you under all that?" he asked.

Mom reminded him to call me Nancy while I was dressed for the part, and that I should call him "Bill", as he was now supposed to be my brother.

"I'm sorry, Nancy," Bill said. "No offense."

"None taken," I replied, "So what do you think?" I asked nervously. "Do I look like an older woman?"

"You really do, and a beautiful one at that" he said, "I don't know if I can get used to it, but you look amazing. It's really confusing for me. I know you're my son but looking at you now, it's just hard for me to wrap my brain around it."

"Well get used to it, Bill," Mom said lovingly, "Because Nancy is in this for the long haul. Once summer gets here, if she decides this is the life she wants, we'll never see our boy again, and you'll have a sister for real."

I rolled my eyes at her dramatics. "Geeze, Mom - Karen. You don't have to say it like that," I said. "Deep down I'm always going to be you guys' son. I'm just not going to look like it."

"So how was your first day in public as a woman?" Dad asked.

I told him it was great but that it was unbelievably scary. "I kept thinking someone I knew was going to recognize me, and I was afraid of messing up and doing things the way a boy would. But I'm getting use to it."

"I can't imagine what you're going through," Dad said, then he hesitated for a moment. "Your mother said you started smoking to help with the stress. Is that true?"

I nodded sheepishly and thanked him for giving me permission.

"I know that smoking relaxes your mother when she's stressed out. Is it helping with your situation?" he asked.

I didn't really start smoking because of my nerves, but I stuck to the explanation Mom and I had agreed on. I told him it that it was helping me a lot.

"I'm glad to hear its helping," my father said. "By the way, I had a little talk with Sammy today and I told him that you've started smoking and I explained to him why you need to do it," he said.

"How did he take it?" Mom asked, as she lit up a cigarette of her own.

"I won't lie to you," Dad said. "He took it pretty hard at first and I can't blame him for that. Darren has been his big brother all his life and now he's having to think of him as his older aunt. You have to admit, it is kind of confusing. But the good thing is that he came around after we talked it about it for a while. I think he's getting to the point where he's starting to accept that Nancy isn't his brother and as an older woman, she's going to do a lot of things that Darren would never do."

Mom breathed a sigh of relief and said, "So do you really think Sammy is starting to accept Nancy as an older woman?" she asked.

"I think he is," Dadl said, "But I've been thinking about it and I think it would help if Sammy spent some quality time with Darren, as Nancy of course. You got to think of it from Sammy's perspective. He's losing the brother he's loved and looked up to all his life. He needs to know that Darren still loves him even if he's going to be a woman."

"I think your father is right," Mom said. "I know you can't toss a football around with him the way you used to, but maybe you can take him to the park tomorrow and watch him play. Do you think you can go out in public without me?" she asked.