The Best Man

The cellphone in my purse rang insistently as I pulled into the parking space outside my apartment. I fished it out and glanced down to see whether I should answer as a man or a woman. It was Jim! "I thought you were on your honeymoon. Had it with married life already?"

"It's a long story, bro. I'm on my way over."

"Over from where?"

"The airport. We're getting drunk tonight." He hung up before I could say anything. In a panic, I dashed through the parking lot and up the stairs to my apartment, as fast as my skirt and sandals would let me. Twenty minutes! That's all the time I had to transform myself back into a guy, hide my girl stuff, and make my apartment look like it wasn't a woman's.

"Damn him!" I muttered to myself as I kicked my sandals under the bed, noting as I did that my painted toes and shaved legs meant I'd better put jeans and sneakers on...why was Jim back in town anyway? Hadn't he booked two weeks in Maui? I mused as I scrubbed off my makeup and went to work on my manicure...what a waste! "Damn him!" a muttered again. I tossed my wig under the vanity and stepped into a cold shower, just long enough to wash away the lingering scent of my cologne. A few minutes later, I was pulling on a rugby shirt and surveying my apartment for tell-tale signs off femininity. I finished getting dressed and ran a comb through my wet hair after I made sure that all the fashion magazines were safely tucked away. I looked around my bedroom one last time, sweeping some loose jewelry into a dresser drawer and closing my closet door as the doorbell rang.

He looked like hell, if you can say that about a guy with a face like a film star and an All American's physique. Even his Hawaiian tan couldn't conceal the lines under his eyes, which had taken on a sadness I'd never seen before. "Dude, why are you here? Where's Julie?"

"Still in Maui," he sighed as he crashed onto my sofa. "I hope she stays there."

"That bad?"

I popped two Coronas and handed one to him. He threw half of it down in one long swig and finished it off with a burp. "Her parting words yesterday were, 'You must be gay.' What a bitch! How could you let me go through it?"

"Whoa, cowboy, don't blame me. I tried to talk you out of it, remember?"

"I know, dammit, it's my own fucking fault. She's hot, she's rich, and she's a total bitch."

"Two out of three ain't bad," I said in a lame attempt at a joke.

"You try spending the rest of your life with a diva."

"But you guys were great together..." I said half-heartedly.

"Listen, Chris, you know me better than anybody on earth. We've been friends since second grade, we double-dated more times than I can remember, and you were best man at my wedding. You knew I was making a mistake, and you tried to tell me, but I didn't listen to you, and now I'm fucked."

* * *

"Beeeeep.......beeeeeep.........beeeeeeep!" I pulled a pillow over my ears. Why the hell were the garbage guys here so early? They never got to my apartment before I left for work...."Work!" I shouted like Maynard G. Krebs, sitting up with a start. A glance at the clock on my nightstand confirmed the worst: it was almost noon!

I got out of bed and staggered into the bathroom. My head felt like a punching bag, and my tongue tasted like an old sneaker. Standing over the bowl in my tee shirt and shorts, I viewed the sad remnants of the burger and fries I'd thrown down, then back up, last night between many, many beers with Jim. How the hell did we get home last night? Jim didn't actually drive in his condition, did he? Was he as wrecked as I was?

A groan from the living room answered that question. I found him splayed out on the sofa, looking like death warmed over. "My head," he moaned.

"How many beers did we have last night?"

"I stopped counting at twenty. Twelve for me, eight for you." Since Jim outweighed me by 100 pounds, he was probably in better shape than I was, which wasn't saying much. And I was the one who had to get to work! I sat down at my computer and began scrolling through my emails to see if I'd been missed. I was in luck: my boss was out of town, and my assistant had phoned in sick. With any luck, I'd be able to get in before anyone was the wiser. I was about to log off when I glanced down, horrified to realize that my shaved legs and bright pink toenails were there for Jim to see.

I pushed back my chair and raced to my bedroom. "Gotta get ready for work," I shouted as I slammed the door, but not before I glanced back at Jim to see him sitting up with the strangest look on his face. I threw up again in the shower, managed somehow to shave without killing myself, and felt almost human by the time I'd brushed my teeth and swallowed half a dozen aspirin. Meanwhile Jim had pulled himself together enough to fire up Mr. Coffee, and when I emerged from my bedroom in a coat and tie, he handed me a mug and asked if he could crash in my apartment for the rest of the day. "No problem," I shouted on my way out the door.

Jim's car, although parked between two spots at a crazy angle, seemed to be undamaged, I noticed as I zoomed off to work. Soon my mind was consumed by my real world problems, and it never occurred to me that I'd left my computer on, password unprotected, my innermost secrets exposed.

* * *

Most of my cohorts were blessedly still at lunch when I pulled into the garage, and I was able to make it to my cubicle unnoticed. I fought back waves of nausea most of the afternoon, getting caught up on emails and phone messages, although my brain was still too fried for serious work. I found my mind wandering back to my marathon conversation with Jim at the brewpub, which I could recall in fragments through an alcoholic haze.

"So you're definitely dumping her?"

"Let's just say it's mutual."

"It boggles the mind: the big wedding, all those guests, her family, your family...."

"All the swag...hell, she can keep it as far as I'm concerned, and the ring too."

"Dude, that rock must have cost you a fortune!" Not that Jim was hurting for money: his signing bonus when he was drafted by the NFL set him up for life, thanks to some savvy investment advice from me.

"She can shove it up her ass."

"So what happened? I thought you guys were great together. Was there like some big secret she was keeping?"

"You mean like was she really a guy?" he laughed, and I laughed along with him, in spite of myself. "Trust me, I'd drilled her enough times before I popped the question to know she was great in the sack. That wasn't the problem."

"So what was the problem?" Jim took a long pull on his seventh or eighth beer, and looked away from me. "Come on, buddy, you can tell me."

"I just got sick of her."

It didn't add up. "You said she called you gay," I remembered. "What was that all about?"

"Don't want to talk about it," Jim sulked.

How could I blame him? For years I'd struggled with my own sexual identity, hiding from everyone I knew my passion for dressing up as a woman. Thanks to my slight stature and androgynous physique, when I finally got my own apartment and screwed up the courage to venture out en femme, I'd passed effortlessly. Now I was spending more and more time in my female persona, which I found infinitely more enjoyable than life as a scrawny, geeky guy.

Jim and Julie's wedding invitation had been a brief intrusion into my increasingly feminine world, and although I'd been honored to be his best man, as soon as they left for Maui I'd gratefully swapped my tux for skirts and dresses.

* * *

"Honey, I'm home," I said in my best Ricky Ricardo after I finally escaped from the office. When Jim and I were frat buddies, we'd spent hours watching old TV shows, so much so that we often communicated for days at a time by mimicking whatever characters were in reruns that semester.

"Maybe you should be Lucy," I heard from across the living room. From the direction of my computer. "Man, you've got some far out favorite places." Before I could concoct an excuse, Jim pressed on. "The ladyboys from Thailand are my personal favorites."

"Uh, yeah, some of them are smokin' hot," I said with every ounce of manliness I could muster.

"And all these pictures of this hot chick...I didn't know you had a twin sister."

My heart sank. "Uh, Jim, let me explain...."

He swiveled in my deskchair and looked me square in the eye. "Chris, I'm cool with it. I kind of figured out already that you were into something like that. Either that, or you've taken metrosexuality to a whole new level."

I slunk over to the sofa and tried to lose myself in the cushions. "Jim, nobody knows about this...."

"Don't worry buddy, your secret's safe with me. So how long have you been dressing up as a chick? Your pix are amazing. Do you really look that good?"

I just let it myself go. "For as long as I can remember, since I was maybe five or six. I used to sneak into my mom's closet and try on her stuff."

"But we've known each other since second grade, and we were roomies for three years at State. You never slipped up once. Damn, you should have been a spy or a secret agent."

"It's been tough, and there's been a lot of close calls," I sighed.

"So what makes you do this? I mean, do you want to be a chick? Hell, you've dated lots of girls, do you play dressup with your dates?"

"No!" I shouted, startling Jim and myself with my intensity. "No," I repeated in a normal voice, "none of them ever knew, and I never wanted to be a girl."

"So have you made it with any guys?"

"No!" I shouted again, tears streaming down my cheeks.

"Listen to me," Jim said. "You don't have anything to feel guilty about. Especially not with me," he added softly.

"What does that mean?"

"It means I'm not exactly straight, Chris." You could have knocked me over with a feather. Was my best friend, an NFL tailback who'd gotten all the girls he ever wanted and made me look like a 98 pound weakling, telling me he was gay?

"Wow," was all I could manage. * * *

Dinner that night was a subdued affair, compared to our outrageous bender the night before. Over diet cokes and pizza, Jim poured out his troubled soul to me, recounting how many girls he'd made love to, each one sexier than the last, yet each less enjoyable as slowly but surely he came to grips with his sexuality. There were his escapades with a discreet number of guys, mostly on away games or camping trips, when I'd never been around. He wept openly about his guilt for getting married, a last-ditch effort to go straight which was doomed from the start.

When the conversation turned to me, it was almost anti-climactic. Until Jim gently prodded me to dress up for him. I thought he was kidding at first, but a strange excitement came over me at the thought of sharing this side of myself with someone. Although Jim was my closest friend, and undeniably gorgeous, I'd never been physically attracted to him. Yet there was something about his discovered vulnerability, and our shared secrets, that made me feel closer to him than I'd ever felt towards anyone, man or woman, and he was very persistent. "C'mon Chris, it'll be fun. I've hung it all out for you, the least you can do is show me the girl you've been hiding from me all these years."

When reluctantly I finally agreed, it was on my terms and conditions. "You will move out of here now," I pronounced in my female voice, "and take me out on a proper date tomorrow night. Someplace nice, if you expect me to shave my legs and put on a dress for you, so don't show up looking like a bum."

"Yes, dear," Jim said, and we both laughed in nervous anticipation. * * *

Needless to say, I got next to nothing done at the office for the second day in a row. Whenever I tried to concentrate, I found myself daydreaming about my big date. What should I wear? As always, I was underdressed for work in panties, but tonight would call for something special in the way of lingerie. Thanks to my booze-induced bulimia two nights before, my waist had never been more girlish, and I'd given myself a full body shave in the shower that morning. The forecast called for an unseasonably warm evening. Sundress weather!

I slipped away a few minutes before five and flew home. Until I got on the expressway...traffic was a bitch, and by the time I got back to my apartment, I had less than an hour to get dressed for Jim! I tore off my clothes, raced into the bathroom and started the tub, pouring more than the usual amount of bubble bath into the swirling hot water. I gave my face an extra-smooth shave and hopped in, luxuriating for a few blissful moments in the piles of hot bubbles before I ran my daisy razor over my legs once again. Then I lay back, pointed my painted toes and kicked my feet girlishly in delight. Enough of this foolishness, what if Jim could see me now? I emerged from the suds to prepare myself for my first ever date with a man.

After patting myself dry with a thirsty towel, I moisturized from head to toe with an expensive crème from France. Then, with the towel wrapped around my feminized body, I went to work on my makeup, taking more time than usual to line my eyes, mascara my lashes, shadow my eyelids, blush my cheeks and gloss my lips. I'd have to rely on myself for my manicure, but I was pretty good at it by now in in no time my nails were glistening. Then it was time for my wig, which I patiently styled and brushed until it was perfect. I gazed for a long time at my reflection in the mirror, and the pretty girl who now was me smiled back. Poor Jim...he didn't have a chance!

Time to get dressed! I decided to wear what any girl would wear on a hot, sultry night for a date with her best friend: nothing fancy, just a bra, panties, sandals and a sundress. So I tucked my sorry manhood into my white lace padded panties, snapped on my lacy white bra, tucked in my magnificent silicone breastforms, and slithered into my green and white sundress. Turning this way and that in front of the full-length mirror after I zipped myself up, I took a moment to admire my waspish waist and deeply tanned legs. Poor Jim...he didn't have a chance!

A glance at the clock on the nightstand brought me back to reality. He'll be here any minute! I stepped into my strappy white sandals, sifted through my jewelry box for just the right bling -- an opal pendant which was perfect with my dress, matching earrings, a woman's watch, and some simple rings -- and finished myself off with an extra spritz of my most expensive cologne. The confident young woman looking back at me in the mirror was drop-dead gorgeous. Poor Jim...he didn't have a chance!

I was organizing my white purse when I heard his knock on the door. Let him wait a minute, I said to myself as I finished with my purse and gave myself one last inspection. Then I waltzed to the door and opened it with a smile. He was handsome as hell in a light blue blazer and gray slacks, and I could tell from the look on his face that he was delighted with me as a woman. "Look at you!" he said with genuine surprise. "You're a knockout!"

"Thanks," I said with a girlish lisp. "You're not so bad yourself."

"Come, milady, your chariot awaits."

"In a minute. Here, make yourself useful," I said, handing him my purse. He stood there and held it awkwardly with an amused look on his face while I rummaged through the hall closet for my little white cropped sweater with short sleeves. "In case it gets cold in the restaurant," I explained, relieving him of my purse. So where are you taking me?" I asked as he escorted me to his Porsche.

"To be honest, I made two reservations: one at a drag bar, in case you...well, you know, and one at the Four Crowns." I punched him on the arm, hard. "Ouch! Where did that come from? The downside of dating a guy...don't worry, we're going to the Four Crowns."

I took his arm and smiled up at him. Jim was almost a foot taller than me, and in my little sundress, I felt so petite next to him, even though my sandals had 2" heels! "I've always wanted to go there as a girl," I said as he held the passenger door open for me. I plopped myself delicately down on the bucket seat and caught him staring at my legs before he gently closed the door. I played with my dress, tugging it just above my knees while he scurried around the back of his car, and checked my reflection in the visor mirror before I sat back contentedly in the plush leather seat. This was going to be fun!

"So how does it feel, Chris? Can I call you Chris?" he asked as he drove, deftly brushing my knee with the back of his hand while he worked the gears.

We were headed straight into the evening sun, so I took my sunglasses out of my purse. "Chris or Crissy...how does what feel?"

"How does it feel to be all dolled up like that? Are you comfortable?"

I closed my eyes and took a mental inventory of my sensations. How could I begin to describe my feelings at that moment? For as long as I could remember, dressing up as a girl had been an incredible rush. Just the thought of those wonderful, forbidden clothes against my skin was enough to send my dopamine levels through the roof. As my journey across the gender frontier progressed, to the point where I became able to pass through the world as a pretty woman, those feelings had intensified and become addictive, and now I was living my ultimate fantasy: being the girl on a date with a cool guy. How could I ever expect Jim to understand these things? "It feels nice," I said at length.

"It shows," he said. "I've never seen you look happier. And you're a heck of a lot better looking as a chick. I hope you don't take that the wrong way," he added quickly.

"Nope," I smiled. "I know I look better this way. I should have been born a girl."

He pulled up in front of the Four Crowns and this time it was the valet who ogled my legs when I emerged from the Porsche. "How did you get so damn good at this?" Jim whispered as I took his arm again.

"Practice, practice, practice."

He opened the massive door and waited for me to step inside before he put his arm around my shoulder and escorted me to the maitre'd. "Smith, reservation for two." Now it was my turn to whisper as we were lead to a romantic booth in a dark corner of the elegant restaurant. "Mr. Smith? How original." I waited for him to pull back my chair, draped my sweater over the back and sat down with a swoosh of sundress. The white table cloth was resplendent with china, crystal and silver, and a waiter materialized to unfold my linen napkin. I took off my sunglasses and perched them on top of my head, and for the first time Jim and I sat face to face, staring for a long time into each other's eyes. "I guess that makes me the other woman, Mr. Smith."

"Last week you were the best man at my wedding. Now it's like I'm seeing you for the first time, and I can't take my eyes off you," he said, taking my hand. "Everything about you is so feminine."

I felt a delicious stirring in my panties. "Down boy," I said, as much to myself as to him. The waiter returned to break the spell. Jim asked me if I'd like a drink, and my mind raced...what was the girliest cocktail? "A Cosmo," I said.

"And a Manhattan for me," Jim ordered. We resumed our small talk, and in spite of the strange circumstances, we soon lapsed into familiar conversation, except as man and woman, chatting about this and that as if we were any other couple. When I glanced at my menu, Jim asked me what I'd like, and I had the thrill of my life when the waiter returned and Jim said smoothly, "The lady will have...." I looked around the crowded restaurant from time to time, and was relieved to see that nobody was paying the slightest attention to us. It was like we were the only two people in the world, sharing this incredible secret.

"How long have you known you were gay?" I asked between bites.