The Encounter

by Philippa Jane Kingsley
 © 2010, all rights reserved.

Philip Prince stood nervously in the checkout line at Payless Shoesource, a closed box of red patent pleather 4" heeled pumps in his hand, his bags from the department store across the street in his other hand.

The woman in line in front of him disgorged her purchases to the cashier, who proceeded to remove the three pairs of shoes from the boxes as she rang them up, placing them in a shopping bag as she went. "You don't want the boxes, do you?"

"No," said the woman, as the cashier tore the boxes to flatten them and threw them on the waste bin with all the rest.

"That'll be $42.97, dear," she said, taking cash from the customer and giving her the bag, her receipt and her change in one motion. "Good morning, Dear," she continued to Philip, taking the box from his hand. "Did you find everything you needed?"

This is the part that Philip dreaded. He didn't like to lie, but he doesn't like to admit that what he's buying is for him. Bored indifference, well-practiced, was his only solution. "I'd like them in the box, please."

The cashier slowed down a beat, it seemed to Philip, despite the three women in line behind him (two on cellphones, of course), taking a moment to size him up. He could swear the corner of her mouth curled up in a repressed smile. "We have a sale on stockings this week, very good prices."

"No, thank you. That will be all, please."

To further show he wasn't intimidated, or trying to hide anything, he paid with his credit card, as he usually did, figuring maybe the cashier will think he was just shopping for his wife or a girlfriend. The transaction completed, he put away the signed credit slip, his card, and gathered up his bags. Letting out a breath he didn't know he was holding, he headed briskly for the door, and escape from the discomfort of being sized up.

The fresh air of the bright spring morning greeted him as he stepped out on the sidewalk, and turned to walk back to his car, only to be knocked flat on his back by a collision with a tall, nicely-dressed woman several years his junior.

"Oh, my God! I am SO sorry! Are you okay?," she said, putting away her iPhone. "Oh, dear! Let me help you up!"

Phil lay stunned, sprawled on the sidewalk, taking a brief physical inventory of his various limbs, butt, and head, trying to catch his breath, this beautiful young woman bending down to help him.

"Wait, wait... Just give me a sec. I think I'm okay," he said, raising himself to a sitting position.
He turned over his right palm and looked at it, a little scraped and dirty, and at two of his otherwise manicured nails, chipped. He looked up, only to realize with horror that his morning's purchases were scattered all over the sidewalk. The red pumps, out of the box. The new bra and panty set, and three pairs of thigh-high stockings, strewn about. The bag with the skirt, open, with the contents clearly visible.

The young woman was focussed on him, though, anxious to help him off the ground. Nothing for it but to let her, he realized. A bit unsteadily, with her help, he regained his feet. "I'm fine, really. I'm so sorry. I should have watched where I was going. I'm glad you weren't hurt. I'm completely to blame," he said, trying to reassure her.

"No, it's my fault. I shouldn't have been hurrying and trying to reply to my email at the same time. Are you okay?" He nodded. "Just stand here, I'll pick up your packages, okay?"

She quickly reboxed the shoes and put them back in their bag, scooped up the lingerie and stockings and put them back in theirs, and retrieved the skirt and its bag, tucking the contents back in.

"Come on," she said, holding his bags. "Let me buy you a cup of coffee. You can sit a bit and get your bearings and make sure you're okay. Okay?" With a free hand, she took his arm and gently guided him towards the luncheonette a few doors along.

"Thank you, but please, my treat. I really appreciate you stopping to help." He smiled, and opened the door for her.

"Hi, Dears! Sit anywhere," hollered the waitress as she headed to the pickup window to pick up an order. "I'll be with you in a sec."

They slipped into a booth about half way back from the windows. "I pass by here all the time, but I've never been in here," said a mostly-recovered Philip. "Have you?"

"A few times. It's not bad. Their coffee is drinkable, and their desserts are pretty good. Their cherry cheesecake is actually very good. Would you split a piece with me?"

"Sure," he replied, as the waitress arrived to take their order.

Philip slipped out of the booth. "Let me get a little cleaned up. I'll be right back," he said, and headed for the men's room, where he washed his hands, splashed a little water on his face, and dealt with his messed-up hair, pulling out the ponytail tie, combing and retying it.

"You look a lot better," she said on his return. "By the way, my name is Beth."

"Hello, Beth. I'm Phil," he said, returning her warm smile.

"You know, I love Payless. That's one of the few stores I can find a bunch of shoes in my size. And their sales are great. You ever take advantage of their buy one, get one deals?"

Her unreserved enthusiasm was disorienting Phil. She was just treating him as a fellow shopper, not a guy who was buying women's clothes and shoes, nor even questioning why.

He started chuckling. "Okay. I figure I'm busted. I don't feel like making up any lame excuses. What would you like to know?"

Her eyes lit up, and she broke into a smile. "Really? You mean these things really are for you? I mean, I thought they might be, but I didn't want to assume," she said softly, leaning closer, chin resting on her hand, her elbow on the table. Her smile was really gorgeous, he noted.

"I have some pictures," he said, pulling his wallet out of his back pocket. "Would you like to see?," he asked, as the coffee and cheesecake arrived, along with an extra plate.

"Oh, yes!," she said, after the waitress had retreated, taking the pictures from his hand, and shielding them from the view of anyone else. If anything, her smile got bigger.

"I love this dress," she said, showing him the full-length picture of him in a magenta silk wrap dress. "The color really suits you. You're really beautiful in it. How long have you been, you know, dressing up like a woman?"

The two sat, sipping coffee, Phil telling Beth of his early crossdressing experiences, and Beth confessing her early desires to crossdress her boyfriends, who were never interested. Phil was shocked, not so much at the revelation, but that she was revealing it to him.

"When I was 14, I could hardly think of anything else. I thought it would be so hot." She looked at Phil, who was trying to digest this. "Do you ever go out?"

"Not as often as I'd like. Maybe once or twice a month. And, mostly just to hang out at a lesbian bar where they just treat me like a friend. They know I'm not there to try to pick anyone up, just a safe place to be."

"You seem pretty friendly. I can see how you'd get along with most people," she said, a hint of something new creeping into her expression. "Do you just go by yourself, or do you have anyone to go out with?"

"A couple of times, but mostly it's just me." She smiled that enigmatic smile again.

"Let me walk you back to your car," she said after he left the tab and a tip on the table.

"Thanks," he said, taking two of his packages, she somehow carrying the bag with the lingerie for him. They walked the two blocks to his car, she holding his arm as before, but this time he leading her. "I've taken a huge chunk of your morning. Can I drop you anywhere?"

"Oh, would you? I was just heading home. It's only about half a mile from here."

Arriving at her building, she pointed across the street to an empty parking space. "Could I ask you a favor? Would you come up for a minute?"

"Sure," he said, maneuvering smoothly into the space and stopping the car. "What do you need?"

"I need to see you in these," she said, holding up the bag she carried from the diner.