I was wearing panties that day under my black denim jeans, a habit that went back a few weeks to the Halloween party given by my sister at her home. My Brooke Shields impersonation that night, a very good one, led to jokes that I could date a guy.
Cross dressing in any form is not something that I talk about. It's just something I do. It would embarrass me if anyone learned my secret but panties, I discovered, feel great against my small body.
Physically I'm 5 foot six, 130 pounds. I could wear, if I chose, a boys medium T shirt.
Jack Lark was my polar opposite. At six feet, 180 pounds he cut an imposing figure. I was not very athletic. He was very athletic. Where I tended to say little and mingle less, he was sociable and talkative. Some of what he'd say was tongue in cheek. He could make people laugh.
If I had a friend at the office it was Jack. We made small talk just about every day at break time. I had even given him pointers about his computer at home.
The Apollo Club in the city is one of the area's best known and popular gay bars. Good reviews bring in mostly the twenty-something crowd but also a few in their thirties, and forties. It features a horseshoe shape bar, back room pool tables and front room DJ playing loud popular dance music. Drinks, whether beer or hard liquor, are cheap.
The club caters to and welcomes cross dressers. Photographs I had seen on the internet showed tv types dancing and mingling with male patrons.
My urge to dress feminine had been growing stronger. If I can look enough like Brook Shields then I can go to a tv friendly club. Al right so I'm gay.
By now thirty-five I had limited experience at sex with men. My one relationship had lasted just a couple of months before he left never to be seen again. The thought had crossed my mind that he was cheating on someone, a husband perhaps.
Not everyone who is gay flaunts it or even tells anyone. One certainly would not say anything to co workers. No one at the office had any way of knowing who, other then himself, might be gay.
The stereotypes are created by the porn sites and television shows. One is that they are muscular adults or skinny, cute teens. The stereotype created by television is that we're all effeminate.
Planning to go out that Friday evening I began gathering up my outfit. A brief search inside my dresser located the self adhesive false breasts next to pairs of panties in the middle draw.
By seven the look was complete. I had put on a black short sleeve cinch top, red mini skirt, and heals. My legs were smooth and completely hairless. My makeup, which I had become very skilled at applying, was Brooke's color. The bra was a push up type.
The men who never dress call us "girls." That's fine with me. I don't care. Cheryl is my alter ego.
The Apollo club was crowded when I walked inside around 8 30. Strobe lights cast red, blue and green streaks on the ceiling. Now and then an ordinary white light flashed. Couples crowded the dance floor to the steady, loud beat of the music.
Besides me several other cross dressers mingled with the men in the place. I began checking out all of them just to see what they were wearing. Mini skirts were common. I was also scoping out the boys.
Suddenly to my left was a most surprising sight. It's Jack from work. This is awesome. I think I'll go chat with him. So what if he knows who I am.
I made my way over to where he was sitting at the bar drinking beer from a stein.
In a flirtatious mood I sat one stool to his right and was scoping him out. He's so gorgeous.
"Do you come here often hon?"
"Sometimes," he replied. "The 'girls' here are hot."
Placing a hand on his thigh just inches above the knee drew his gaze down. My hand moved lightly and gradually following my eyes toward his lap. His cock was stiffening slowly.
"You're not bad looking either." I winked.
" What's your name sweetheart?"
"Cheryl," I replied.
"You remind me of someone at my work."
I suspected he knew to whom he was speaking.
"I've been here before. I've never seen you here."
"I don't always come on Friday night."
"What does a boy like you do on weekend?"
"I play on a hockey team but there was no game tonight."
"I just adore athletic men. They're strong, handsome."
"Well I adore hot babes."
I took hold of his hand. "Let's dance," I said.
Up at the dance floor I thrust my lips against his pressing hard for several seconds. He returned my passionate kiss. His hand slid down my back to my buttocks.
We began to move sync to the music, stepping back then toward each other. I turned under his raised arm. But after just a minute or so we closed the gap between us and sashayed. Before the dance was finished I kissed him again, this time pushing my tongue into his mouth. His hand now slid to my buttocks squeezing gently.
The song phased right into the next tune. Jack and I continued the same moves.
Leaving the floor, this time we headed toward a table for two just a few steps away holding hands as we walked. Our eyes locked onto to each other from across the table and our hands clasped together under the table.
"I like the way you dance."
"I have fun with cute men."
The conversation shifted.
"What do you do for a living?"
"I work in an accounting department. It's a big company."
"Loeman's. They grind lenses."
"That's a coincidence. I work there in accounting. Hello Clark Stewart."
"I love to dress. I just feel so nice in a skirt."
By this point in the evening I wanted him to take me home and take my panties down. I wanted his cock and would let him know it.
"Let's have another dance."
"Sure," he said and took me by the hand out to the floor.
Out in the middle of the floor I kissed him passionately for several seconds while rubbing his manhood through his slacks.
Perhaps a minute into the tune we actually began to sashay back then toward one another in sync with the music. Again I turned under his raised arm.
Passions heated as the song neared the end. We closed wrapping arms around one another. A deep, wet kiss followed lasting several seconds quickly followed by another. His hands roamed freely caressing my entire body.
"Jack," I whispered, "I want your cock inside me and I want to suck you."
"Go for it Cheryl Clark Stewart."
The long ride back to Jack's apartment was spent just talking. The talk was nothing too personal just places we had been, my brief affair with Philip, and a little about music and movies. We had seen some of the same movies. For weeks I had been having my secret fantasy that I could never reveal to him. That would soon change.
When we entered the building his apartment was a short walk down the corridor to 6A. I wanted him.
Just as we entered the apartment and he closed the door behind us I pushed him toward his sofa and onto it. Again I pressed my lips onto his in a passionate kiss.
"Take my panties down! Do me!"
Taking my hand Jack led me into his bedroom. While I lay on the bed he opened my skirt and nudged it down then took my panties. Easing his body down he kissed my lips.
"Cheryl Clark you are so fuckable. I want you."
I watched excitedly while he removed his pants then his shorts. Rolling me onto my left side he moved into position and pushed his huge cock into my glory hole. Long and fat it rubbed tissue stimulating nerves, and touching the prostate. I moaned softly pleasured by it's slow and steady rocking motion inside me.
The time was coming up on 730 when I awoke on Saturday and pushed back the covers. Beside me Jack lay facing the opposite direction. His head sunk deep into his pillow.
Wanting more sex I gazed at his ass then slipped my hand toward his flaccid manhood. After a couple of seconds, stimulated by my gentle stroking, it stiffened in my hand.
"That feels good panty boy."
We stood caressing one another and with cocks touching in the shower. My knees touched the tiled bathroom floor and my lips closed tightly around his throbbing sex taking the whole seven inches. Sweet man meat touched my tonsils.
"Suck that big cock!"
On the way to his desk Monday morning Jack stopped at my cubicle.
"Good morning Clark," he said in a soft voice.
"Yes it is," I said smiling.
Standing five feet away not quite making eye contact was his way of enabling plausible deniability.
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