Virgin in Shemale Club

I have made a lot of mistakes while drunk in the past.

I fucked what I thought was a hot MILF but ended up being a much older grandma and not even remotely hot.

I fucked a very obese woman who nearly crushed me to death when she rode me.

I fucked my girlfriend’s mother while my girlfriend was sleeping downstairs.

Just to name three.

But that paled in comparison to what just happened last night.

I was bar hopping in San Francisco and had already been to a drag bar where I was luckily still sober enough to recognize an Adam’s apple on an otherwise feminine looking person who was hitting on me pretty hard, when reached a club called Deception, a club I recalled my colleague Fran, one of the few who had so far resisted my charm, had said I had to visit if I was in San Francisco.

I asked, “Why?”

“It’s a bar where you are guaranteed to get fucked like you have never been fucked before,” she said, always talking like she was a guy.

“I can’t imagine how that is possible.” I smiled, flirting back.

“Trust me, it will change your life,” she said.

“I’d change your life if you’d let me,” I flirted.

“Trust me, you couldn’t handle me,” she countered.

“Challenge accepted,” I joked.

“Once you get back from Deception we will talk,” she said.

I thought the name was odd, but I just wanted another drink and hopefully a hot chick to take back to my hotel as I hadn’t been laid in a week, which was a pretty long time for me… and I recalled Fran’s words.

In retrospect, a sober me would have likely caught many of the warning signs.

There was a twenty buck cover, which was a bit steep, but if the women inside were half as hot as the woman taking my money I figured it was well worth it.

She asked, “First time?”

“Is it that obvious that I’m a Deception virgin?” I joked, not realizing the accidental innuendo I had opened with… I was just being my suave self.

She laughed, as she handed me a red glowing bracelet, “You won’t be for long, sexy.”

I loved these moments of flirtation. Regardless of whether I scored or not, flirting was my drug… that and beer.

I’m a good looking guy. I’m not being smug, just admitting the truth. I’ve never had trouble scoring with the ladies because I’m the complete package: sexy, built, blue eyes and blonde hair, funny, suave, well-dressed, a great job and a decent seven inch cock that wasn’t so big it scared the ladies but big enough to keep them very satisfied.

For the record, I’m not some smug asshole. I know I’m blessed and I also make sure my women get pleased too.

I just get bored.

I’ve never met one that makes me keep coming back.

Sex is just sex….

I know that makes me sound like a sexist pig, but I believe that when I meet the one I’ll just know… like my mom and dad, who have been married forty years.

Anyways, I was given a free shot ticket for one ‘Puckered Rosebud’, a drink I had never heard of before.

But I was not one to turn down a free drink and headed straight to the bar where a very beautiful blonde smiled, “First time here, sexy?”

“Is that what the bracelet symbolizes?” I asked.

“Yep,” she nodded. “Are you from around here?”

“Canada, actually,” I answered, already feeling my seduction today could be the bartender.

“Oh, well when in San Fran,” she said, as she handed me a shot.

“What’s in it?” I asked.

“Bartenders secret,” she answered, “but it will loosen you up a bit.”

“What if I want to loosen you up a bit?” I flirted back as I took the shot.

She laughed, “Oh, I’m not sure you could handle me.”

I smiled, charm on full, “I’d die trying.”

“I’ll keep that in mind,” she said. “Now down your shot.”

I downed it. My throat burned as it was the most intense shooter I’d ever had.

“Down it with this,” a gorgeous redhead smiled as she handed me a drink.

My throat burning, I took the whiskey glass and downed it. It too was like a prairie fire burning my throat.

The bartender laughed, “Josie, you’re going to kill the Canadian.”

“A Canadian,” the redhead purred. “Yummy.”

I blushed, as I downed the water the bartender handed me.

“And what brings you here?” Josie asked.

“You,” I replied, turning on the charm as I sensed she was already a willing participant.

“Really?” She smiled, seeming to put a similar amount of charm in her tone. I suddenly wasn’t sure if I was the hunter or the prey.

I nodded, “Can I buy you a drink?”

“At this bar the ladies buy the drinks,” the redhead replied, her green eyes hypnotizing me. She waved to the bartender.

“Best bar ever,” I joked.

“Oh, you don’t know the half of it,” she smiled as she leaned in and tugged on my ear lobe. “I’m going to fuck you so hard.”

I had been hit on by women before… many times. But never with such aggression and forwardness.

I smiled playfully, even as my cock hardened, “Maybe I don’t kiss on the first date.”

Her hand went to my cock as her tongue swirled in my ear, “me either.”

The bartender returned with drinks and quipped, “Be careful Canuck. Josie is a predator that doesn’t take no for an answer.”

“Thankfully, I don’t play hard to get,” I groaned, as she kept rubbing my cock.

The bartender laughed. “Well, don’t say I didn’t warn you.”

Josie ordered, her hand disappointingly leaving my throbbing cock, “Drink up.”

I grabbed the drink and was thankful when it was a normal whiskey and Coke.

“Wanna dance?” I asked.

“Wanna fuck?” She countered.

“Where have you been all my life?” I quipped, this woman really turning me on.

“Let’s go,” she said, taking my hand even as I was in mid drink.

I followed and was surprised when she led me into the bathroom. I was also surprised to see there was only one bathroom.

I asked, “Is this one of those unisex bathrooms?”

“You could say that,” she said as she led me into one of the seven stalls.

As I followed, I heard a guy groan, “Oh yes, fuck me.”

I wondered what kind of bar I was in.

Before I could really ponder that, Josie dropped to her knees, fished out my cock with expert precision and devoured it whole.

“Oh God,” I groaned as she sucked my cock like an expert.

“Oh God, harder,” the guy groaned, which confused me.

As I watched her bob back and forth I noticed a hole in the wall. I smirked, shit this place even had glory holes.

After a couple of minutes, I warned, “You better slow down or I’m going to shoot my load prematurely.”

She allowed my cock to slip out of her mouth as she stood back up and said, “Well, we can’t have that,” as she put her hands on my shoulders and guided me to my knees.

“I love a woman that knows what she wants,” I purred, impressed by her aggressiveness and looking forward to tasting her pussy.

“Remember those words,” she said as she looked down at me.

I thought that was a strange response, but horny and drunk all I wanted to do was taste her pussy and then fuck her.

“Come in my asshole,” the guy screamed just as I nodded and lifted up her dress.

As I reached for her panties my eyes went big at both the revelation of what was happening in the other stall and the fact that Josie had a hard bulge where her pussy should be.

“Fish it out,” she ordered.

I stammered, paralyzed in bewilderment, “Y-y-you have a dick!”

“Yeah, thanks for letting me know,” she sarcastically quipped. “Now pull my panties down and get sucking.”

“I-I-I’m not gay,” I tried to explain as I continued to stare at the anatomy error.

“I didn’t say you were,” she sighed, pulling her panties down herself to reveal a hard, big, thick, eight inch cock. “Now fucking get to work.”

I couldn’t believe it. She expected me to suck her cock.

I went to speak… to protest… when she suddenly shoved her cock in my stunned, open mouth.

She grabbed my head and began fucking my face, making me gag.

I had no choice but to suck.

“That’s it cocksucker,” she groaned, holding my head firmly, “you look so hot with my cock in your mouth.”

The words were ridiculous as I couldn’t imagine I looked hot as I tried to stop gagging on the huge dick assaulting my mouth. I also would have never, in a hundred years, imagined that derogatory term being used on me.

After a few more deep thrusts, she pulled out. She asked, as she looked down at me, “Is this your first cock?”

“Yes,” I answered, as I looked up at her and then back to her cock, still completely overwhelmed with my sudden predicament… the bartender’s warning suddenly making complete sense.

“You want it back in your mouth, don’t you?” She smiled.

And oddly, as I finally got a good look at the cock, the answer was yes. I couldn’t explain it, but her cock was beautiful. These thoughts only confused me more.

“Answer me, cock sucker,” she ordered, tapping my lips with her dick.

“Yes,” I quickly answered feeling compelled to obey this beautiful woman with a dick, my mouth literally watering as I wanted it back in my mouth.

“Yes, what?” She asked as she traced my lips with her thick mushroom top.

“Yes, I want to suck your cock,” I admitted, not feeling any shame at this declaration, but rather an undeniable hunger.

“Well, then get to work, cock sucker,” she ordered.

This time she didn’t shove her cock in my mouth.

This time it was me who leaned forward and willingly became a cock sucker.

“Good boy,” she moaned as her cock disappeared in my mouth.

The tone was smug, and maybe condescending, and yet it seemed appropriate. Now in control of the sucking, I slowly moved back and forth… in awe of how natural it felt to have a cock in my mouth.

I had never even remotely considered sucking a cock before, but now that one was in my mouth it seemed natural.

“That’s it, take your time and worship my cock,” she purred, as she put her hands in my hair.

I couldn’t believe I was on my knees.

I couldn’t believe she had a cock.

I couldn’t believe I was sucking her cock.

I couldn’t believe I was enjoying it.

As I got used to the girth that stretched my mouth a lot wider than a Popsicle I began to work on taking more of its length in my mouth.

I gagged excessively when she roughly fucked my face and for some reason now as I took my time I wanted to impress her… to be a good cocksucker… as strange as that was to think.

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