The Best Man

"I was in denial for a long time. I'm still ashamed to admit it. It's not like I'm the only guy in the NFL who's gay, believe me. But I fought it every step of the way, and I never wanted to be different."

"So you got married to Julie."

He hung his head. "Biggest mistake of my life."

"So what are you going to do about it?"

"Annulment."

"She's going to take you to the cleaners."

"Prenup."

"Well played. Now what?"

"Well, I'm not quite ready to come out as Bruiser LaRue." I gave him a quizzical look. "He was the caricature of a gay quarterback on that old AM radio station we used to listen to."

"I remember," I laughed. "I doubt if your sponsors would dig that."

"And they don't sell that many NFL jerseys in the Castro. You must think I'm a total hypocrite."

"Jim, we've been friends since second grade. You don't have to apologize to me about anything. Anyway, who am I to judge? I'm the one who's sitting here in a dress, who's been living a secret life for as long as you've known me."

He took my hand again. "Thanks for being such a good friend, Chris...I mean Crissy." He slid his hand up my arm and shook his head. "I can't get over it. Your skin is so smooth, just like a girl's."

I felt that stirring in my panties again. "I thought you weren't attracted to girls," I teased him.

"So did I." Once again, the waiter broke the spell when he returned with the check. I took my lipgloss out of my purse and freshened my face with a few deft strokes. When I looked up, Jim was staring at me again. He watched intently while I tugged on my little sweater and slung my purse over my shoulder. "Damn," he said, "it's like you've been doing this all your life."

"Since I moved into my own apartment, I've been making up for lost time," I said while we waited for Jim's car. He opened my door for me, and once again I could tell he was staring at my legs, just as I used to on the rare evenings when I talked a girl into going out with me, a lifetime ago....

We didn't say much during the drive back to my place. We were each lost on our own separate thoughts, trying to process what we'd learned about each other, and our feelings. On a superficial level, I was thrilled to be a pretty girl on a date, and I never wanted it to end, but there was something deeper going on that I couldn't deny, and I wondered what Jim would think if he knew.

When he pulled into my apartment complex, I asked him if he'd like to come up for a cup of coffee. "Sure," he said, and I took his arm as he walked me up the stairs. He sat down tentatively on the sofa where he'd spent most of the past few days, while I puttered in the kitchen until the coffee was ready. Then I handed him his mug and sat down beside him, demurely sipping mine in awkward silence. "Can I tell you something?" he finally asked.

"Uh oh."

Jim slid next to me and gently took my mug from my hands. "Promise you won't get mad at me?"

"Let me guess...you've always had a thing for chicks with dicks?"

"No, Crissy. I've always had a thing for you."

Twenty-four hours ago, that would have seemed impossible, incredible...now it seemed strangely natural, and the stirring in my panties returned. "Come on, Jim, you really can't expect me to believe that...the big man on campus had a crush on the runt of the fraternity?"

"It's true, from way before then...when we were in Mrs. Penn's class and you always let me copy off you, and you were always reading those brainiac books, I wanted you to like me."

"Is that why you wanted to double date all the time, even when you had to set me up with a girl? Are you saying you really wanted to be getting it on with me?"

"No, silly, I wouldn't have dared even think that back then. I just admired you, that's all, and felt a little sorry for you too."

"Because I was such a loser. I suppose that's why I got a mercy bid to your fraternity when I followed you off to college."

"I didn't mean it that way," he said, and he put his arm around my shoulder. I felt myself tremble as his hand caressed my bare skin, then his other hand slid under my dress and stopped a few inches from my throbbing panties, gently stroking my thigh. He leaned in and before I could turn away, he brushed my lips with a gentle kiss. He lingered there, backed off for a moment, then he kissed me again, a deep, passionate kiss that curled my toes and rewired my brain and body forever. It was like somebody threw a switch: one minute I was a guy in a dress, and the next all I wanted was to be Jim's woman, to become as intimate with him as our imaginations dared, to feel this way forever. I threw myself into that kiss, exploring him with my tongue, until we finally came up for air. "Wow," he panted.

"Me too." I searched his eyes and wondered if my best friend could possibly be my soulmate? So what if we were born the same gender? No one had ever touched me like this. Who was to say something that felt so right could really be wrong?

Sometimes there are words that express our innermost feelings, and sometimes words don't matter. Jim took my hand, stood up and said four words that were to change my life. "Let's go to bed." I followed him docilely into my bedroom, then stood facing him while he gently unzipped my dress, which fell in a puddle to the floor. I kicked off my shoes and started to unbutton his shirt. When I was finished, I unfastened his belt and unzipped his slacks. The bulge in his briefs was enormous! Then he picked me up, with one hand tucked under my thighs and the other wrapped around my shoulders, and gently laid me down on the covers.

I snuggled down in my pillows and waited for him to make the next move, as if it was the most natural thing in the world to have a man undress me and climb into my bed. My life was changing at warp speed, and I wanted to savor every sensation, remember every moment, of the mind-bending journey Jim was taking me on. He didn't disappoint, tenderly kissing me from head to toe, and I followed his lead. God, what a body he had! Shaved as smooth as mine, but ripped and hard as iron, he'd have made me feel like a girl by comparison even if I hadn't been wearing a bra and panties. Not for long...he tugged my panties down to my knees, then he dove between my legs and started to suck me. It felt so wickedly delicious! Instinctively, I started to play with him too, and then I took him into my mouth, wanting him to feel the same thing I was feeling. My head was spinning. Was I really going sixty-nine with a sexual athlete? Together we shared a rising crescendo of desire until I knew we couldn't hold out much longer...when I felt him start to throb it triggered my own orgasm, at once so familiar yet now so new, like the very first time, sensations like nothing I'd ever experienced. It was sheer ecstasy, waves of indescribable pleasure pulsing through me as we came simultaneously, feeding each other with our sweet seeds.

We came down to earth, a jumble of conflicting thoughts in my head. I just had sex with my best friend. A guy. And I liked it. No, I loved it. I'm gay. What's he thinking? Is he going to get up and leave me now? Can we ever be friends again? I looked up at Jim, who had an impish look on his face. He pulled me close and kissed me on the forehead. "Was it good for you?"

"I think I've died and gone to Heaven."

"Whew."

"Huh?"

"I thought maybe I was moving too fast with you."

"And I thought you'd be halfway out the door by now."

"You thought I was a love 'em and leave 'em kinda guy?"

"Well, I do remember certain post-date horror stories when you got back to the frat house...."

"That was then."

"And now? What just happened to us, Jim?"

"Don't worry your pretty little head about it, Crissy." He kissed me again, on the lips, a deep, passionate kiss that started me stirring again. A practical problem: I hadn't been to the bathroom since before I turned myself into a woman, and nature was calling, desperately.

"Don't go away," I told him as I slipped off the bed and into the bathroom. Yikes! I said to myself when I saw my reflection in the mirror. My wig and makeup were a total mess! After I took care of business, I went to work with a hairbrush and lipstick, then before I went back to bed I had an inspiration. From my closet I fetched my black and pink babydoll nightie with a matching thong, and a black velvet choker with a pink ribbon. I'd fallen in love with them when I saw them at Victoria's Secret, and always wanted to wear them...now or never! I took off my bra and slithered into the nightie, which was clingy enough to create a hint of cleavage over my flat chest. After I fastened the choker and stepped into the thong, for the hell of it I grabbed a pair of sheer black thigh high stockings and minced back to the bedroom, where Jim was waiting impatiently.

"Wow," he said. "Where have you been all my life?"

I perched on the edge of the bed and began sliding on a stocking, reveling in the sensation of nylon against my skin. "Right under your nose, big boy," I said. "I thought you weren't attracted to the female form?" I finished putting on my stockings, stood up and did a little twirl for him.

"I'll make an exception in your case. C'mere, you," he said, patting the bed next to him.

I curled up next to him. "What did you have in mind?" I asked coquettishly.

"I'm going to make a woman out of you. Do you have a condom?"

"Goodness! What kind of girl do you think I am? They're in the nightstand."

I watched him tear open a package with extra-lube and roll it onto his hardening penis. I was still soft, but that wasn't going to matter...he told me to lie down, very much the man in charge, then he slid a pillow under my butt. Off came my thong, and the next thing I knew Jim was on top of me, gently probing my quivering rosebud. I gasped when he entered me and I must have cried a little because he whispered "Don't worry, baby, I'll be gentle" as he made his way deeper and deeper into me. The shock and pain soon gave way to an incredible feeling of fulfillment and raw, carnal pleasure as he had his way with me, in and out, in and out, like a piston penetrating my innermost defenses, and I surrendered willingly, it felt so damn good! At some point I wrapped my legs around his neck, and the sensation of nylon against his skin drove him wild...in and out, in and out, deeper and deeper he went, until he clenched his teeth and his breathing became heavier and heavier...."Oh baby, I'm gonna cum soon!" he moaned, and I felt myself beginning to lose control, in a way I never had before. It couldn't be possible, I was still soft but I felt the beginnings of my own orgasm welling up deep inside me, like a woman's orgasm, and my whole body shuddered when Jim cried out, "Yes! Yes!" and I felt him in my tummy, powerful pulses that I knew so well, yet could not compare to the feelings of ecstasy that overwhelmed me as I climaxed around him in spasms of sheer delight that went on and on and on....

"Are we having fun yet?" Jim whispered when I finally opened my eyes. Gently, slowly, he pulled himself out of me, which felt so delicious that I thought I was going to have another orgasm. He cuddled me close, gently stroking me, and we lay there in silence for what seemed an eternity, as our heartbeats gradually returned to normal. Normal...what was normal for me anymore? I'd just been made love to as a woman. I'd just made love to a man. My universe was spinning out of control. "Talk to me," Jim finally said to break my trance.

"Was it good for you?" as if I needed to ask.

"The best. You're amazing."

"I feel like a dishrag."

"You're too pretty."

"Do you realize that we just had two simultaneous orgasms? A lot of people live their whole lives without ever experiencing that, even once...."

"Wanna go for three?"

"I wanna go for a lifetime," I blurted out, without thinking. Stupid, silly me!

Then came the biggest surprise of all. "I love you."

"You do? Really?"

"Yes, I guess I always have, and now I know for sure."

"Oh Jim, this is all happening so fast! I love you too."

We kissed, a long, sweet, tender kiss, a man and wife type kiss. "I've been thinking," he said.

"That's good. When we were kids, I usually did the thinking for you."

"That's what I'm thinking. We could make quite a team."

"As long you're the one who wears the pants, and I get to be the girl."

"Wouldn't that bum you out, pretending to be my girl?"

"Are you kidding? Sounds like a blast, if you think we can pull it off."

"Oh, you can pull it off all right, baby. Tonight at the restaurant, I was the envy of every guy in the place."

"And I was the envy of every girl in the place. Where's this going, Jim?"

A long pause. Then, "Can you take a little time off from work?"

"Sure, why?"

"Well, I paid for two weeks in Maui, and I hate to see that second week go to waste...."