By: Brian Holliday
(© 2010 by the author)
Editor: Rockhunter

The author retains all rights. No reproductions are allowed without the author's consent. Comments are appreciated at...

“You’ve got to be kidding!” I tried to rise out of the chair in front of the little mirrored dressing table, but Frankie pushed me back.

“Come on, at least take one more look.” She adjusted the long black wig she’d placed on my head.

I stared beseechingly at Geno, dressed as usual before a show in a slinky sequined cocktail dress and his own blonde beehive wig. “Sorry, Baby,” he gestured toward the mirror with his cigarette holder. “Mirrors don’t lie.”

Frankie smirked and picked up the green eye-shadow. “A little of this, some lipstick, and maybe some eye-liner and you’re ready to go.” She peered into the mirror. “I’d kill for your eyelashes.”

Well… fuck.

“I’m not shaving my legs,” I whined.

Frankie looked down. My calves, under the dressing gown, were covered in a light dusting of short black hairs. “It’s either that, or a floor-length dress,” she said, unsympathetically. She turned toward Geno and held up a pair of shoes. “What goes best with these?”

I eyed the black patent leather pumps with the four inch heels. “I’ll fall and kill myself on those things!”

“Just think graceful,” Frankie said.

“Just think Grace Kelly,” Geno corrected.

Oh, God.

It had started out as a joke. For sure, I was gay, and one of the most dedicated bottoms you’d ever want to meet, but… drag? An hour later – shaved, painted, and zipped into a knee-length black cocktail dress that apparently went perfectly with those damned heels – a joke is just what I felt like. Frankie dragged me (pun intended) to the mirror again and held me there. Frankie was tall for a woman, almost matching my six feet, but now her red-headed figure was lost behind my too-broad shoulders and the extra four inches those pointy-toed torture devices added to my height.

Geno walked over to stand beside me. Even in heels, he only came to my shoulder. “Looking good, Sister,” he said, reaching up to pat one of my foam-rubber ‘chests’ more firmly into place. Geno was over forty, and had been doing his “Miss Gina” act on the stage for years. According to him, that made him an expert.

“How do you stand it?” I asked, shifting my weight from one spike heel to the other.

“Beauty hurts,” he said, walking away after slapping me on my (unpadded) butt.

Tell me about it. I’d yelped every time Frankie tweezed an eyebrow.

Geno and the other ‘girls’ had tried to convince me to wear some of their rhinestones, or at least a leopard print jacket, but I already felt conspicuous enough.

“Frankie,” I tried one last time. “Please tell me I don’t look like a circus clown.”

She shook her head. “How many times do I have to say it? You look beautiful.” She draped a gauzy shawl over my bare shoulders and stood back. “There. Just remember to speak quietly, and you won’t have to worry about your voice.” She grinned. “Men think women with low voices are sexy.” She picked up a tiny black purse and handed it to me. “Everything a young woman on the town needs for a perfect evening… cab fare, mirror, lipstick… “ She grinned again. “And condoms.”

“Frankieee… “ I whined. “I can’t go out like this! What if one of the guys sees me? I’ll never hear the end of it.” My friends would tease me unmercifully, and Dan might want me to… shudder… dress like this again.

“Just go to a different bar,” she suggested, practically. “Come on, you gotta try it out after we went to all this trouble.” She paused, put an arm around my waist, and leaned in. “And… I want to hear all the juicy details tomorrow.”

Oh God, again.

Frankie was my best friend, but I still didn’t know how I’d let her talk me into this… and Geno? I swore I was going to feed his favorite feather boa to the neighborhood alley cats.

“OK, OK,” I said. “But just this one time.”

Frankie held up her fingers in the Girl Scout salute. “Scout’s honor,” she said.

I held up one of my fingers. “Scout this.”

“Tsk,” Frankie said, “remember, you’re a lady.”

I sighed.

Dressing like a woman is drafty. I could feel the breeze all the way up to the tight black satin panties… the ones specially made to hold my dick and balls back between my legs. Did I mention that beauty hurts? Personally, I couldn’t see the point to that last bit of insult to my threatened masculinity. What difference did it make if my junk hung down under the dress? I was going to a gay bar, after all. But Frankie insisted, and Geno backed her up, of course, and about that time a couple of the other queens came in to add their nickel’s worth and insisted that all the best people were wearing them this season so… I was outnumbered.

Anyway, it was chilly. So I snugged the shawl around me, for all the good that did, and walked, Grace-fully, as Geno had showed me, out to the curb and got into the first cab I could find.

“Where to, Doll?” the cabbie gushed.

I shook my head, then put a smile on my ruby-red lips and said, “Hot Dog Heaven, please,” keeping my voice low, like Frankie said.

The cabbie raised an eyebrow, and winked. “You got it, Doll,” he said.

I’d given some serious thought to which bar to attend. Dan and I were known at most, if not all, the gay bars in town, so the choice was not an easy one. But the Dog was only semi-gay and, because of that, we and our friends didn’t hang out there much.

The ride across town took about twenty minutes, which gave the cab driver plenty of time to wink at me in his rear view mirror. I tried not to roll my eyes, and to sit with my legs together in a ladylike fashion, and to keep my shoulders back to show off my new hood ornaments. The black dress was backless, almost to the point of revealing those aforementioned panties, but came up high in front, in a little Mandarin collar, while leaving my shoulders bare. That meant the cabbie couldn’t stare down my fake cleavage, but that didn’t seem to bother him much… he stared anyway. After a few minutes, I started to sort of enjoy it.

Damned if he didn’t leap out and open the cab door for me. Relying on the memories of all those old movies I’d watched, late at night, I placed one hand in his and let him ‘help’ me onto the sidewalk.

I’d worried about my hands, because they were big, even for me, but Frankie had suggested shaving the backs and my arms too, and then slathered them with about a pound of moisturizer and painted the short nails to match my lips. My Bronx-accent Sir Galahad didn’t seem to find a thing wrong with them, but I pulled away as quickly as I could.

His smile was so wide, I thought he was going to refuse the tip I gave him, but he pocketed it and stopped to salute me with his cap as he got in and drove away. At least he hadn’t blown a kiss.

The Dog was well into its weekly drag show. When I walked in past the bouncer (thank God he didn’t want to check my ID) several young maidens, or reasonable facsimiles, were strutting their collective stuff on the stage. A couple of them were as tall as me, and some had on less clothing, but all were convincing, if your definition of female was broad. (OK, I apologize for that one.)

The room was crawling with people of all varieties. I saw several guy on guy couples, a few pairs of lesbians, and even some mixed twosomes on the dance floor. Alcohol fumes and tobacco smoke thickened the air and I belatedly remembered I’d forgotten my cigarettes. Damn.

Then I saw him. He was all alone at a table for two, a ruggedly handsome blonde dressed to kill in a black suit that fit him just right. It must have been specially tailored because this guy was linebacker big and muscular. The blue shirt brought out his eyes and the striped tie and gold tie-clip were the perfect finishing touches. Classy. Certain confined parts of my body tried vainly to sit up and take notice.

I must not have started drooling quite yet, because he looked up from his martini and gave me the biggest, whitest smile, stood up, walked over, and escorted me back to his table. I did not protest.

The short skirt always rode up when I sat, so I had to concentrate on pulling it down to keep from flashing the tops of my hose or more. It was work, just remembering all the new rules. And I’d thought being a gay man was complicated.

“What’s your name, Honey?” the big guy asked, in a gorgeous bass voice. My little heart went pitter-pat under all that padding.

Then it struck me. Name? Why hadn’t we talked about names when Frankie and Geno were coaching me on everything else?

“Um… uh… “ I stammered. “Eve.” The very first woman… good choice. At least I hadn’t said ‘Mary’.

He smiled. “Pleased to meet you, Eve. I’m George.”

George’s eyes were roaming up and down my seated figure, from borrowed wig to spike heels, maybe paying a little extra attention to my chest, I thought. God, could he be straight?

Nah. I didn’t remember seeing the guy in a gay bar before, but he’d seen the talent on the stage. I figured he had to know where he was. I smiled and he put his hand over one of mine. I was amazed. His was actually bigger. Now, what did that make me think of…?

A skinny waiter in black pants and a white shirt was cruising by our table. George signaled him. “What would you like to drink, Eve?” he asked me.

“I’ll have a glass of white wine,” I said, keeping my voice soft. I knew I’d have to watch the alcohol. In this getup, I didn’t want to forget myself and head for the men’s room.

The wine and another martini for George were there in a flash. The music was pretty loud, so we were making do with interested glances until a lull when he asked me, “Do you come here often?”

Well, George wasn’t going to get any prizes for originality. It was lucky he was so naturally endowed that his line didn’t matter. I would still have been transfixed by those bulging shoulders if all he’d said was “Ugh,” like Alley Oop, the caveman.

“No,” I said, delicately sipping a little wine.

“I thought not. I know I would have remembered someone as attractive as you.”

Still no creativity points, but I smiled anyway. Then he dropped it on me. “What clubs do you usually work?”

Oh, my. Dear George thought I was a prostitute. I almost laughed, but then I stopped to wonder. Would a regular woman be offended? If I wanted to keep up the charade, did I have to slap his face?

I settled for a hurt look – at least I hope that’s what it was. I stared down at my lap, fluttering the eyelashes Frankie would kill for.

“I’ll have you know that I’ve never charged for it in my life,” I said, righteously, which was perfectly true.

His manner changed completely - before he had been all ‘man of the world,’ now he was the teenaged boy on his first date, having spilled a milkshake all over his girlfriend’s sweater. “Gosh, I’m so sorry,” he said, “I guess I just can’t believe that a beautiful girl like you is here, alone.” He looked away and I hid a smile behind my hand. This was fun. “Don’t you even have a boyfriend?” he asked.

“We’re separated,” I said, mock-sadly. Sort of true… I had no more idea where Dan was tonight than he had about me. It was the kind of arrangement we had.

“I hope I haven’t been too forward,” George said. “It was just that, when I saw you come in, I felt instantly that we had something in common.”

Yeah, like maybe we’d both played football in college?

“I felt the same,” I said, fluttering.

The band started up again, with a rendition of “Blue Moon.” “Would you like to dance?” he asked.

I had certainly danced with another man before, just not in heels. He led me to the floor and by God, heels or no, he was taller. I grinned, then toned it down a little. Ladylike, you know.

“You dance well,” he said.

“Thank you,” I said, modestly.

Several of the gay couples were out there on the floor with us, and I noticed George looking over at one or two of the most attractive guys. Well, I was too, of course.

We danced a couple more, and ordered more drinks. In between dances, we chatted, and he seemed pleased that I knew about sports. I guess a lot of gay guys don’t but - big muscular men patting each other’s butts - what’s not to like?

I was feeling pretty good after a couple glasses of wine and, since George was ahead of me by about two to one, he must have been feeling positively loose. We’d just finished dancing to another slow one - an instrumental version of Patsy Cline’s “Crazy,” and George had been holding me close while something hard poked me in the hip. I was pretty sure he wasn’t carrying around a salami in his pocket.

“Eve,” he said, and the confidence was back in his voice. “Would you like to come home with me?”

Cool, I thought. He’s figured it all out, and now we can go back to his place and have a good time. Best of all, I could get out of these damned clothes! I wondered if George would loan me a shirt and pants to go home in.

We kissed in the cab, and I narrowly kept him from groping my chest. Guy must be into foam rubber. I did let him reach up under my skirt, and he seemed quite taken with my nylons and garter belt. I decided it would be better if he didn’t get too friendly in what was essentially a public place. I had no desire to be arrested… again… for indecent exposure, especially if they took me to the women’s side of the jail… those dykes would kill me. I distracted him by stroking the impressive piece of meat I found between his legs. That kept us both happy.

By the time we got to his place - a nice apartment in a better part of town than the one I shared with Dan - I had to pee… bad. He opened the door and grabbed at me, but I handed him my shawl and told him to wait while I ‘freshened up.’

Of course, I had to remove those elastic undies first. I hoped they hadn’t done my equipment any permanent harm but everything seemed to be in working order. I tossed the panties on the bathroom vanity – they had done their part for the evening and there was no way I was putting them back on… ever.

I almost removed the whole get-up, but some guys get a thrill out of unwrapping their gift package. Who was I to rob my friend George of that pleasure?

With my skirt smoothed back down, you couldn’t tell the panties were missing.

Back in the living room, George had removed his coat and tie and looked as though he was ready to go for it. He grabbed me and we kissed again, a nice long one that soon had my hormones in overdrive. His hand went for my zipper, but I could see a big bed through a doorway and, since I was sure to be the one on the bottom, I opted for comfort. I grabbed his hand and tugged him after me, and he didn’t seem to mind, not even when I removed his belt, undid his zipper, and shoved his pants to his ankles. His jockeys were next, and then I pushed him down on the bed and knelt between his knees. It only took another minute to remove his shoes and then the pants came off easy enough.

George sat very still, watching with evident fascination as I caressed the well developed snake that rose up before my eyes. With no further ado, I swallowed it whole.

Before very long, he was moaning and trembling, and I stopped what I was doing and sat back.

“You ready for this, big boy?” I asked, holding up a condom packet. He nodded, panting a little, and squirmed while I rolled it on him, giving him one last slurp to moisten the latex.

I stood up and George all but threw me onto the bed, not that I minded. I landed with my skirt still modestly around my knees, and George started pushing at it, until he could spread my legs enough to get between them, his manhood bouncing each time he tugged. Obligingly, I bent my knees, pulling them up to my chest. That was all it took for the skirt to flip up the last few inches.

His eyes got big as dinner plates as he stared down at my cock, happily erect and glad to be out of its uncomfortable confinement. “Surprise!” I said. His expression made me wonder if he thought it might bite him.

Up ‘til that moment, I’d been sure he knew, and I gotta admit I felt a sudden stab of alarm. I’d heard of guys who’d been beaten up by straights, for nothing more than walking down the street.

I’d do my damndest to fight back, if it came to that, but this guy was BIG! My eyes locked with his baby blues for what seemed like forever, and then he shook his head, groaned, and sank that beautiful tool into my ass.

I was plenty ready, and he was nice and wet, so the lack of lube didn’t bother an experienced trooper like me. I just rested my legs - nylons, heels, and all - on his shoulders, and we went at it like bunnies - which is to say - hard and fast.

Did you ever see bunnies do it? Takes them about three seconds. Big George lasted longer than that, but not a lot. Luckily, the whole situation had me so fired up I shot almost the same time he did.

He collapsed on top of me then, his chest heaving. After a minute or two, he rolled to one side and just lay there, flat out, covered in sweat and some of my cum.

I was thinking I should brace myself – never easy when you’re trying to catch your breath – because I still didn’t know what to expect from him, now the fireworks were over.

Finally, he moved. He pulled off the condom, tossed it away, and rolled over toward me. When I saw the sheepish little smile on his face, I relaxed and obligingly turned so he could spoon against my back. In a moment, one thick arm snaked over and curled itself around my waist. He pushed the long hair aside and I could feel his breath on the back of my neck.

“That your real hair?” he asked.

“Loan from a friend,” I answered.

“Oh,” he said.

He pulled me a bit closer and settled himself more comfortably. His breathing slowed down and I figured he was almost asleep. Then…“I knew it all the time,” he whispered.

Sure you did, I thought, but I didn’t say anything. I may be a good cocksucker, but I know when to keep my mouth shut.

Thanks to Rock Hunter for his excellent editing.

Posted: 04/16/10