Back in my collage days, I earned some extra cash working in a night club. I started collecting glasses on the floor, then moved to serving behind the bar. It wasn’t long before I was asked by our manager to be a Shift Supervisor.
It was at a time that I was coming to terms with my identity. I was a Transvestite, but there was a lingering homosexuality about me also. I preferred girls that was for sure, but I was not adverse to sucking cock and taking a load in my ass.
I knew that I wasn’t into men, masculinity really didn’t do it for me. But slightly effeminate guys, did float my boat.
So, I was in the midst of a gender and sexuality crisis.
And that’s when Denis joined as Bar Manager. He was in his fifties, he was lean, he was refined and gorgeous. I honestly struggled. Denis was the first man that I crushed on. I couldn’t get him out of my head.
On his first day, he arrived in the bar wearing a well-tailored suit, crisp white shirt without a tie and a pair of clean shoes. The previous managers were fat men’s men, in ill-fitting jeans and more often than not; a 3 day old bar staff polo shirt. They stank of cheap aftershave, cigarettes and perspiration, Denis was wearing expensive cologne.
He oozed confidence and sophistication, I swooned. Like a Victorian school girl, I walked about all day light headed, somehow on the verge of both hysteria and passing out. I have had crushes before, but as a handsome boy in my early twenties I was always able to handle myself in a reasonably dignified manner.
Not with Denis. My tongue tied in knots, and cock was constantly oozing precum; I was a total mess.
Over the following few months, I composed myself. I was on the threshold of finally regaining my dignity when Denis announced that for the upcoming Halloween Ball the bar staff would be in fancy dress.
Fancy Dress for a closet Transvestite meant the opportunity to break out the heels.
I was gonna be FABULOUS!
I spent three and a half fortunes, on my ‘costume’, there was to be no Primark for this little fairy. I bought the little black dress that I had been izmir escort drooling over for months, the black patent leather heels that made me tingle in strange ways, and lingerie that would make Madonna blush.
I skipped my classes on the day of the ball, I preened and pruned. I shaved, I moisturised I painted and I made over this twenty something boy into a classy whore.
I stood in the mirror straightening out the seams in my stockings wondering if I was going to be able to change a keg of beer in my 3-inch stiletto heels and long false French nails. When suddenly the thought of Denis popped into my head. My tucked cock strained against the panties, my chest tightened, and my blusher got more and more rouge.
I tossed off my anxieties and applied another coat of pink lip gloss, and made my way to work.
In these stories, and tales on sites and forums such as these. The heroine dresses for the first time and is instantly unrecognisably a beautiful woman. This wasn’t my first time! I have been practicing for years. When I dressed, I transformed myself into my female persona. This is how you can tell a transvestite from the blokes dragging up for Halloween.
I was stopped a couple of times by the security staff as I entered the bar before opening.
“Sorry love you’ll have to queue outside like everyone… Bloody hell Stevie!” was how one of the security guards reacted.
Soon we were setting up. I was still working behind the bar, so we were preparing the ice buckets and stock. My friend Laura called me into the glasswashers room for a closer inspection. She and I had been regular fuck buddies. She mauled me as she inspected my outfit. Pawing at my tits, running her hand up my dress over my tucked cock.
“Girl your gonna make a killing in tips tonight.” I blushed again she continued. “If Denis doesn’t take me home to ride the shit out of me, I am sitting on your face tonight.” We giggled. Little did she know I also fantasied about getting fucked by our boss.
The night went really well. Laura was correct of course, I made loads antalya escort in tips. The bar was rammed and we got murdered. But it was so much fun being me, that the night passed really quickly.
Periodically I had to empty the twenties out of my till and take them to the supervisors. I walked into the cash safe with about ten grand in twenty pound notes when Denis said “Fucking hell Stevie, I’ve been walking round with a hard on all night.” I smiled and said something like “Yea there are loads of hot girls about tonight.” He looked deep into my eyes and said, “No that’s not it. I saw you changing a keg earlier and saw your stocking tops.” I laughed and jokingly called him a poof, and made my way back to the bar.
There were a few more odd moments, with him throughout the night. He brushed against me just a little too closely a couple of times. Then as we approached midnight I was going to the office to reset my till when I heard Denis and Kelvin one of the supervisors who was openly gay, talking about me. Denis was saying “I can understand how you went gay Kelvin. Stevie is totally doing my head in. I can’t get her out of my head.”
Kelvin answered with something about shemales being revolting, but I was fixated on the fact that Denis was thinking about me and that he referred to me as ‘her’.
As I entered the office I smiled, at both men. Kelvin got up and left saying that he would leave us too it.
The POS system was located in the office beside Denis’s desk. To stop people using it as a porn computer it didn’t have a seat, and was pretty low down. I obviously had to bend down to use it. I could have knelt down but I wanted to test how straight Denis was. So, I bent over. Showing Denis my black satin French knickered ass, and garter straps.
It worked. He leapt forward and ran his hand over my ass cheeks, then gently between my legs to my tucked member.
He stood up and he slammed his door shut and dropped his trousers at the same time. He fiddled with both our underwear pulling my panties aside and dropping his briefs. A rock hard kayseri escort long and slim circumcised cock bobbed its way to my behind.
I had been horny all night. Between the really cute girls wearing slutty costumes and the thought of what Laura was going to do with me later kept me on the edge. My little ass hole was opened up. Denis spat on his fingers and fingered my little bud, then wrapped his fingers over his cock and coated it in his slippery spittle.
I reached behind and parted my cheeks and offered him my ass. He stepped forward, his cock edging closer, and closer. He applied more spittle to my back side and to his dick.
“Are you sure?” He asked.
I looked at the screen the reboot of my till was going to take another five minutes. “You’ve five minutes before my till is up and running.”
As I said it the tip of his cock pressed against my crack just above my opening. It slipped down and missed the entrance, jabbing me in the balls. He gasped as I took him in my hand and guided him to my eager hole.
I held my breath, the tip of his cock was touching the edge of my asshole. The expectation was tantalising. Soon he was edging forward, I opened up relativity easily. His helmet was inside me, making its way deeper and deeper. Before long he was buried within me. I had wanted this for months, I had spewed my seed countless time dreaming about his cock inside me.
My boss is fucking me I thought as he took me by the hips and started to withdraw. It was sore, but I have had much worse. I knew the initial sting would soon wear off.
Before long my cock was oozing precum into my panties, he was pounding into me. Calling me names ranging from faggot to princess. Eventually he whispered
“Stevie can I cum in your mouth?” I dutifully obliged and slipped off his meat dropped to my knees, and opened my mouth for him to jerk into. Three stokes later and his seed was shooting into my awaiting throat.
He slumped to his seat breathless and sweating. “Fuck me!” he exclaimed. Coming down from his cum. The computer beeped to tell me that my till was now up and running. He offered me some tissues to clean my face.
On the way back to the bar, I passed Laura taking a break in the kitchen. And a wicked thought crossed my mind. I kissed her deep in the lips, before breaking away and whispering into her ear “Now you know what Denis’s spunk tastes like.” I winked and returned to work.