tagTransgender & CrossdressersBecoming a Drag Queen

Becoming a Drag Queen


Summary: A man on a trip to San Francisco descends into the drag queen world.

Warning: This story is a rather lengthy tale with a fair amount of plot at the beginning. That said, as the story unfolds the sex comes in pretty heavy doses.

Thanks: To the amazing copy editing of Estragon who catches my many mistakes.

Thanks 2: A thank you goes to the following who gave me insight for this story: Candicame, Art, Dave, Liz, Josh, Clint, Susan Rossi, Starr, Mike, Lindsey and the others who shared their thoughts.


Becoming a Drag Queen

I was thrilled when my boss told me he was sending me to San Francisco for a conference. It was a location on my "Top 10 places I wanted to go". I went online and Googled the major attractions and tourist "must sees in San Francisco. The conference was Wednesday to Friday and I figured I would add a couple of days and tour this unique American city. Through the Google search, I found many cool things to do in San Francisco. By the end of the night I had made a list of twenty potential activities. As the week went on and I talked to a few colleagues who had been to the city already, I ended up with a lengthy list of must-to-sees, must-to-dos and must-to-eat-ats. It was a daunting list, and one I could never do in the amount of time I had. So more Google searches for reviews, and I finally had it narrowed down to a few choices. I ordered tickets for a musical "Beach Blanket Babylon" and, of course, a trip to Alcatraz. The rest I figured I would decide once I was there.

The first night there, after checking in, the bellhop recommended a blues bar that specialized in southern food. I love southern food, so I headed to the club. After getting lost once, I found the club and had a superb southern fried chicken supper. I stayed for an amazing blues show, staying way later than I had anticipated.

It was during the second evening that a long ignored fetish rekindled. I was at "Beach Blanket Babylon", a must-see show I was told (and I have to agree), when part way through I saw a guy in drag singing. Now I should note that I have a pantyhose fetish and, although I have ignored it since I got married, I was getting the urge to wear pantyhose again, something I had long denied myself.

When I was younger, I would often steal my Mom's pantyhose and wear them underneath my clothing. I briefly thought I may be gay because I liked to dress in pantyhose, but I liked chicks too much and back then no one was openly bi, so I eventually squelched my desire to wear pantyhose and moved on. I still had my pantyhose fetish and loved seeing them on women. My wife, Isabelle, had amazing legs and, although she thought my pantyhose fetish was odd, she often wore them for me when we went out. She even cut a hole out in a few so she could wear them during sex. We had a great sex life, but our relationship had slowly fallen apart. We really had nothing in common, and we got divorced six months before my trip to San Francisco.

I got off the trolley and on my way back to my hotel I was passing Walgreens and I wondered if they sold pantyhose. I went in and found they indeed did. I grabbed a pair and went to the till. I felt nervous, like a kid buying condoms for the first time. Did the cute cashier know I was buying them for me? She didn't even raise an eyelid at my odd purchase, and I rushed to my hotel room, oddly giddy with excitement. As soon as I closed the door of my hotel room, I got out of my clothes, including my underwear, and put on the soft silky pantyhose. I lay on my bed in my black pantyhose and logged into my computer. I searched Literotica for cross-dressing stories. As I read them, my cock became stiff in my pantyhose, although I had to adjust my pantyhose to give my cock room to grow. Most of the stories ended in gay sex and although I was had never been really interested in other men, my dick stayed stiff as I read story after story. I rubbed my cock through the sheer nylon and it brought back so many memories of my fetish-filled youth. A story where a reserved straight man ended being a cross-dressing faggot in a naughty sex train finally did it, and I shot cum all over my pantyhose. I got up, cleaned the pantyhose off, and left them over the shower to dry. I fell asleep wondering why it was an anal sex gay male story that got me off.

Next day I put my pantyhose back on, without any underwear (what's the point, the pantyhose kept my cock from shifting), and dressed in my usual suit and tie.

The morning was a write-off, as I kept thinking of my naughty secret that no one else knew. My dick stayed hard all morning and at lunch I decided to see if any drag shows were playing on a Friday night. There were a couple, and I decided I would go check one out. It was harmless, but my curiosity lingered. I suffered through a brutal afternoon of conference boredom, and, once I was done, found my body leading me to a Victoria's Secret. I had decided to add to my naughty attire, not completely cross- dressing, but adding frilly underwear to the mix. I bought a pair of bright pink hip huggers. I briefly considered a bra, but that seemed silly and redundant. I then went to Neiman Marcus and decided to buy a pair of real silk pantyhose, the kind you couldn't buy at a Walgreens. They cost forty-six bucks but the Wolford pantyhose were the softest, sheerest silk I had ever touched. I got them in the colour I like to see on women the most: mocha. I got back to the hotel and took a long shower. The show wasn't till ten, so I ordered from room service and took a nap.

I woke up later than planned, just before nine, and rushed to get ready. I put on my bright pink panties and my silky sheer pantyhose. I put on a pair of designer jeans and a black short sleeve dress shirt.

It felt so good walking in my pantyhose that I decided to not wear socks, one more slight risk. I put on my black dress shoes and left. My feet felt so free in just the sheer pantyhose. A crazy cab driver took me to the club, speeding up and down the hills of San Francisco. I could only find a chair at the bar, beside a fully dressed drag queen.

I ordered a beer from the clearly gay bartender and surveyed the room. It was mostly men, a few tourist couples and what looked like a bridal staggette. When I returned my gaze to the bar, the drag queen was smiling at me.

He/she was surprisingly pretty. At first I had to do a double take to be sure he/she was a he. Thankfully, his Adam's apple gave the game away.

He/she said, his/her (I will refer to her as she from now on!!!) voice stunningly high and feminine, "Hi stranger, here for the show?"

Slightly nervous, I stuttered, "Y-y-y-yeah."

"Oh you will love it, honey," she promised, her hand grabbing mine and giving it a squeeze. I was shocked, but much to my surprise, I didn't pull my hand away.

"I-I-I hope so," I stammered, like a shy teenager.

"Where you from?" she asked, her hand still holding mine.

"Canada," I answered.

"You are the second person I have met today from Canada. I am originally from South Carolina."

There was a brief lull as I pondered what to say. She broke the silence, "By the way, I am Flame. Maybe I can light your fire."

I imagine I went beet red and on reflex moved my hand away.

"Did I embarrass you, Darling? You are cute enough to eat whole," she teased, with a devilish smile.

Just then another drag queen came and hugged Flame and I realized this was my chance to leave. Yet my legs felt like cement. Instead, I ordered a second beer. Once again surveying the room, I realized it had got much busier. There was almost nowhere to move and people kept bumping into me and squishing beside me to order drinks. When I returned back around, I noticed that Flame had left. I was surprised that I was disappointed, but noticed her pink purse was still there. I suddenly got a warm feeling inside me. I wondered what the hell was wrong with me. I was bumped again and heard a rather entertaining conversation between two gay men. A very good-looking blonde guy was waiting for his drinks as a guy I could not see pleaded his romantic case. "I really like you. I always have. But you were with Jamie and even though I knew he was not good for you, I just waited. I promise I would never do anything to hurt you." The next thing I knew I was inches away, as two young men started making out. It was like watching a car accident. You know you shouldn't look, yet you can't peel your eyes off the perverse scene.

I felt a hand tap my shoulder and I turned and was face to face with Flame. "Enjoying the show?" she asked, a knowing smile on her face.

I stammered, attempting to defend my staring, "You don't see much of that up in Canada."

"You like?"

"Each to their own," I shrugged, trying to come off as manly and straight. Having to urinate and break the seal, I asked, "Where is the bathroom here?"

She pointed behind her and offered with a flirtatious smile, "I'll hold your seat for you."

I squeezed my way through the mob of mostly gay men and squeezed into the men's washroom. Inside were three stalls and five urinals. In my head, I expected to see some sort of naughtiness, but all I saw were two guys washing their hands talking, and a couple of others taking a piss. Remembering I was wearing pantyhose, I choose the only open stall. Once closed, I quickly sat down and read some of the naughty comments like: 'Garrett will cheat on you," or "Monty has the biggest cock I've ever had,' or 'For a guaranteed good time call Elmer' or 'Adam loves it up the ass.'

While I was reading the comments on the door, I heard the door to my right close, and instantly heard a rough voice order, "Bend that ass over, faggot!"

A few seconds later, I heard what was obviously a guy getting fucked in the ass. I heard whimpering turned into moaning and my cock, thinking on its own, began to rise.

I also noticed a hole on the wall. I knew I shouldn't have, but I couldn't resist. I leaned forward and peaked into the hole. I held in a gasp. I watched a voyeur drawn into perversion. A skinny white guy, bent over the toilet, was being ass-fucked hard by a well-built black guy.

I don't know how long I watched, before the big guy pulled his long cock out of the guy's ass and demanded, "Suck me off bitch!"

The guy quickly dropped to his knees and engulfed the ass-fucker's cock. I had never seen such an eager cocksucker. He bobbed back and forth with desperate abandon. Within a minute or two of this hardcore cocksucking, the big guy grunted and clearly shot his load down the faggot's mouth. The faggot didn't miss a beat as he swallowed the guy's cum.

I looked away and saw Flame's name on the wall. It said, 'No one sucks cock like Flame!"

My already stiff cock flicked and just as I was about to stand up I heard a male voice, "Get sucking, bitch!"

I looked to wear the voice was coming to my left. I saw a cock staring at me. I realized quickly I was in a glory-hole and he was talking to me. Rattled, I pulled up my panties, pantyhose and jeans hastily and quickly exited the stall. Fearful he would come out of the stall, I ignored washing my hands and fled out of there.

As I left, I heard someone yell, "Get back here, fresh meat!"

I squeezed my way back to the bar and chugged my beer. I again thought of leaving, but was distracted by Flame.

"Hey Sweetie," she smiled, her soft hand returning to mine. "See anything interesting?"

"Wow," I babbled.

Still smiling, she continued, "The bathroom here often includes a lot of extra-circular activity." Her finger gently caressed my hand. I should have pulled away, but it felt very nice and was relaxing me.

Attempting to be nonchalant, I responded, "So I learned."

Just as Flame was about to speak again, she was interrupted by a booming voice. "Welcome bitches to our special show. We have some fine ladies here tonight for your entertainment. Be loud and rambunctious and if you like them, give generously. Up first is the sexy, the naughty, Marilyn MoanMoan. She will tantalize you with her 1950's cabaret. So please let's hear it for Marilyn MoanMoan."

The crowd went wild and I watched in secret awe, as this woman, who looked ridiculously like Marilyn Monroe, danced and sang while the packed crowd around the stage offered her bills. While she danced, she took the bills with her hands, her mouth and her breasts. It was all very erotic. I scanned the crowd wondering how many men here were straight, like me.

Flame asked, her fingers making small gentle circles on my hand, "What do you think of her?"

"She is very talented and a dead ringer for the real Marilyn."

"Isn't she?" Flame agreed, before offering, "I can introduce you to her later if you want."

"Ok," I said, unsure what else to say. I missed the introduction, but a new girl was on and looked much more what I expected from a cross dresser. Although she was dressed to the nines, she was obviously a male. Like the first dancer, she did a little number and had many men fighting to give her money. It was like a strip show without the stripping.

I felt a hand on my back and turned to see a Brad Pitt look-alike attempting to order a drink while using my back for stability. He smiled at me, "Sorry."

I responded, starring at his drop dead good looks, "No problem." He got his drinks and went on his way.

"Isn't he dreamy?"

"What?" I asked, turning back to Flame.

"Isn't he dreamy?"

"I guess." I shrugged, not wanting to give any signs that I might be into that type of thing.

"He doesn't play, anyways," Flame said. I assumed I knew what play meant and didn't ask.

The second dancer was leaving the stage. The announcer introduced the next girl while Flame and I talked.

"So you like wearing girl's clothing?" Flame asked, surprising the shit out of me.

"Excuse me?"

"Well I see you are wearing pantyhose under your pants," she pointed out, letting go off my hand and reaching down to touch my sheer pantyhose. "Oh my, and these aren't just any cheap pair are they?"

I stammered, "Um...it was...."

Her hand moved up my leg, and rested just above my knee. Her voice was both compassionate and flirty, "It's ok. If you are just experimenting or curious, Baby, this is the place." Her hand moved up a smidge, and instead of outrage, I felt excitement and my cock attempting to grow, but struggled in the restrictive panties and pantyhose. I tried to ignore the awkward position of my cock, but it was really uncomfortable and I adjusted my cock in front of this hypnotic drag queen. Her smile dripped as she purred, leaning into my ear, her hand moving up ever so close to my stiff cock, "I hope that is because of me."

My face went red but I said nothing, refusing to admit the obvious truth that it was completely because of her.

Not deterred by my silence, she asked, "So do you have a pantyhose fetish?"

I nodded my head and finally spoke, "I have since I was a teenager."

"And, I am guessing you used to wear them and masturbate with them on," she assessed, completely correct; her hand now an inch from my cock.

I couldn't believe it. All I wanted right now was this drag queen, this man, to touch my cock. It was ridiculous. It was absurd. It was all I could think of. I nodded my head in affirmation and slight shame, "Yes, I used to do that."

"Let me guess," she said, "you quit wearing girl's clothing when you got into high school."

"College," I corrected, "I lived in a dorm."

"I see," she purred, "and you haven't done so since...today, have you?"

"Correct," I responded, my head dropping in shame.

Her hand didn't move as she consoled me, "Honey, here in San Fran we accept all kinds: the flaming, the out, the bi and especially the," she paused, a seductive mischievous smile crossing her face as her hand moved and rested directly on my cock, "curious."

I took a deep breath as I battled my conscience. I knew I should leave before I ended up way over my head, yet a larger, curious, part of me wanted to see what would happen next.

Her hand just rested there, a gentle reminder, while we watched another drag queen dance. The silence drove me nuts. It gave me ample time to leave and ample time to ponder about what might happen. Finally, Flame turned back to me, her same seductive smile frozen on her face, "I have to go back stage, I am after Cinderfella."

I laughed at the name and my body flinched, my hard cock pressing up into her hand.

She gave me a wink, a gentle squeeze to my cock and stood up. She leaned forward, her hand returning to my cock and rubbed it gently. Her voice was sweet like honey. "I expect you on the dance floor, Baby. I expect you to be my best little fan." Her hand gave a firm squeeze to my cock. "Will you do that for me Baby?"

I whimpered, her hand doing wonders to my erection, "Y-y-yes."

"Good," she whispered, her lips nibbling my ear. She gave one last squeeze and she was off.

For the umpteenth time, I had the perfect opportunity to walk away. To just up and leave. Yet, when I did stand up part way through Cinderfella's act, in which by the way she looked like a real live version of the cartoon princess, it was to walk to the dance floor. I struggled to squeeze my way close enough to the stage to do what Flame had asked me to. I pulled out my wallet and grabbed a bunch of bills.

Suddenly, I wondered what was the proper etiquette for giving money to a performing drag queen. It wasn't like I could just add fifteen percent like I did for a waitress. I tried to see what others were giving and it ranged: mostly ones, a couple fives, and one ten. I decided right then and there that I would up the ante with my bills.

Cinderfella ended her number and while I waited, I looked around the dance floor. There were guys drinking, guys chatting and a couple of guys making out. Before today that would have made me incredibly uncomfortable and probably even repelled me, yet now it just seemed normal. I was bumped by a couple making out and then a pale flamboyant redhead introduced himself, "Hi, I'm Jay."

I shook his hand and said, "Hi, I'm Paul."

"Nice to meet you. This is your first time here I am guessing."

"Is it that obvious?" I replied.

"Yeah," he smiled, "You are looking all over the place, seem incredibly nervous and flinched a bit when you saw guys making out with each other."

"Oh, sorry," I apologized, attempting to justify it. "I'm from Western Canada, we don't see many public signs of affection between gay men."

He shrugged. "In San Fran, it's hard not to see two gay men together."

We were interrupted by the announcer who said, "And now, the vivacious, the seductive, the temptress, Flame."

The crowd erupted and Flame came on stage to Elvis's 'Burning Love'. I pushed my way forward through the throngs of gay men until I reached the stage. Flame saw me instantly and gave her seemingly signature smile to me. I put my hand forward, waving a twenty in the air. She bent down and took it in her mouth before sauntering away. She was an amazing dancer: both smooth and erotic. I pulled out another twenty for when she returned to where I was standing. The crowd on the dance floor was loud, sweaty and horny. I felt hands on my ass and heard a lot of cat calling and whistling. Flame took my second twenty by bending down and taking it with her breasts, her eyes never leaving mine. I felt like the prey of a hungry hunter, a tantalizing temptress. As the song was coming to an end, I pulled out one more twenty and held it in the air for Flame to see. After taking others money, she crawled on all fours to me, and said, "Put it in your mouth, baby."

I did without hesitation and leaned forward as she took it with hers, our lips touching for just a heartbeat of time. I couldn't believe how soft they were, way softer than any girl I had ever kissed. I watched her crawl on all fours away from me and off the stage, getting a great view of her well curved ass. My cock twitched in my panties as I wondered what it would be like to fuck her ass.

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