Sex In Stilettos

Author: Michael O’Connor

Standing before the full-length bedroom mirror, I treated my reflection to an almost unjustly critical appraisal. My indecently short black leather dress clung for dear life to my every curve and went perfectly with my high heels, whorish fishnets and black leather jacket. It was the sixth outfit I had tried on in the last hour and the bed behind me was strewn with those I had already rejected as not quite right. For this, the most important interview of my life, I wanted to look as perfect as possible.

For once, I was glad Louise was on assignment for Erotimax films. She would have been very suspicious of my story of an appointment with a modeling agency and if she had any idea of what I was really up to, all hell would break loose. In the beginning, I had been flattered by my lover’s possessiveness, taking it as a sign that she treasured me. That was before she gave up her job as a waitress, to embark on a career in porn movies. She made no secret of the fact that she loved her work. Whenever I criticized it, she took great pleasure in detailing who she had fucked or been fucked by before the cameras that day. Despite her unashamed promiscuity, if I were to even look at another girl, she would fly into a jealous rage. Our six-month relationship was becoming too much like hard work, but I lacked the courage to end it.

Forcing all thoughts of Louise from my mind, I decided I looked fine. Whatever our difficulties, I was not about to let the jealous bitch ruin my appointment with destiny.

“Some people call me a groupies’ agent, but that sounds so sleazy. I prefer to think of myself as providing an entertainment liaison service.”

The peroxide blonde in the smart scarlet suit was making what sounded like the standard speech for prospective candidates wishing to join Star-Connexions. Her name was Mandy.

“I pride myself on matching stars with suitable fans and moving beyond the cliched groupie image of stagedoor queens throwing themselves at the feet of their idols,” she continued. “Having worked in showbusiness for several years, I know the requirements of the people I am dealing with and they know they can rely on my discretion.”

“Basically, you select fucks for the stars,” I grinned.

The glare in Mandy’s blue eyes suggested she was far from impressed by my attempted witticism.

“Are you sure you’re not working for some sleazy tabloid rag?” she demanded.

“You’ve done enough preliminary checking to know the answer to that,” I replied. “I’m sorry. I didn’t mean to be crude.”

She glared for another moment, then returned her attention to the application form on her desk. “You describe yourself as a devoted fan of Tamella Van Diemen. The question is, just how devoted?”

I smiled. “I’ve been president of her fan club for the past three years. Seen her nineteen times. I was one of the chosen few at her very first show, in Rubberta Flax club. My home is a shrine to her. I’ve got everything she ever recorded. Bootlegs, rare imports, promos, you name it. Let me show you something.”

Standing up, I turned around and tugged my clingy black dress up over my hips. My skimpy black lace panties had ridden up into the cleft of my ass, leaving creamy half moons exposed. Tattooed on my left cheek was a luridly colored image of the guitar toting rock vixen, thundering through the fires of Hell astride a saddled and harnessed figure with huge breasts and an equally impressive cock. Below the scene, the letters TvD were described in blood red gothic script.

“Very nice,” Mandy commented, leaning back in her chair. “But Tamella has many similarly devoted followers.” She swung her right foot up onto her desk. “Make believe I am your goddess. Show me the depths of your devotion.”

Having been half-expecting such a request, I was only too glad to oblige. Bending over the desk, I kissed the pointed toe of her stiletto-heeled shoe. The shiny red leather was an almost identical shade to my lipstick and smelled intoxicating. I licked the sole, sucked the lethally sharp heel, then roamed my tongue slowly up her shapely, pale silk stockinged ankle. She was sitting in such a position that I had a tantalizing view up her short skirt. At the sight of a white lace panty crotch, I felt the swelling in my own panties become more urgent.

When my adoring tongue reached her knee, Mandy seized a fistful of my shoulder length raven black hair and led me around to her side of the desk.

“So, this isn’t a wig!” she smiled.

“What you see is what you get,” I answered, dropping to my knees at her feet.

She smiled. “I should certainly hope not, Justine. Tamella would not be impressed.”

I knew exactly what she meant. I removed her shoes by gripping the heels between my teeth, then made love to her silk stockinged feet with my mouth. Though she retained her tight grip on my hair, she did not manipulate me in any particular direction. There was no need. We both knew where I was going.

My tongue glided over her long legs, rasping softly against the silk. The feel of the fabric and the heat of the lightly tanned flesh beneath was electrifying. As I finally neared my mouth-watering goal, Mandy raised her bottom from the chair and eased her skirt down over her slender hips. After I had pulled it the rest of the way off, she drew up her knees and hooked her heels in the arms of the chair, lewdly displaying herself for my pleasure. Her white G-string panties were plastered to the soaking mound of her sex, leaving little to the imagination.

“Come on bitch, eat me!” she purred, wrenching on my hair.

No point trying to pretend any longer that she was Tamella. Second best she might be, but her feminine love musk was still intoxicating. I sucked and kissed her through her panties, before boldly ripping the crotch with my teeth.

“Hey, watch it doggy!” she snapped, dealing me a stinging slap across the face with her free hand.

“Sorry,” I mumbled.

Thrusting her crotch against my face, she commanded me to, “shut up and make me cum!”

For the next ten minutes, my tongue was buried in Mandy’s hot slit, while I lapped and slurped noisily on her copiously flowing nectar. Her clit throbbed like a miniature cock and was sufficiently prominent for me to grip between my lips and suck, just like it were the real thing. She responded by squealing in ecstasy and thrusting against my face, as though intent on ramming her little ‘lady cock’ down my throat..

By the time I finally rose from the feast, my face was slick with her juices and my lipstick smeared over my chin. Now, it was Mandy’s turn to pleasure me. Her ruby glossed mouth looked capable of working magic, but she chose to use her feet instead. Without rising from her chair, she hooked her right foot in the hem of my dress and hiked it up to my waist. My panties could scarcely contain the tumescence of my cock.

“Don’t be shy, let’s have a look,” she said, softly. “Hmmm, not bad, though hardly the stuff of wet dreams. Lucky for you Tamella isn’t a size queen. Get your tits out.”

While I duly unzipped my fringed and studded black leather jacket and rolled my dress up above chest level, Mandy squashed my stiff cock between my belly and the sole of her foot. For this special occasion, I had decided not to wear a bra. Proudly, I exposed my pert, firm breasts, a small gold ring glinting in both stiff nipples. Next to going to Tamella’s very first show, starting the hormone treatment had been the best decision of my life. Perhaps one day, finances and courage permitting, I would go the whole way to womanhood.

Mandy hooked a finger of each hand in my rings and forced me to lean forward, so that our faces were only inches apart. At the same time, she moved her foot slowly up and down, in a masturbatory shuffle.

“So, you think you’ve got what it takes to be Tamella’s plaything?” she purred.

“Oh God, I hope so!” I gasped. “There’s nothing in the world I want more than to please her. I would do anything for her.”

Mandy smiled, increasing the cock crushing pressure of her foot. “Anything?”

I nodded. “Absolutely. I’ll be her slave, her dog, her fuckslut, her toilet. For her pleasure, no sacrifice would be too great.” I shuddered violently. “Ahhhhhh.. . I’m cumming!”

My cock trembled and thick globs of cream spewed over her foot. She continued to pump me until every last drop was spilled, then ordered me to kneel and clean up the mess I had made. Only when all trace of semen had been sucked from her stocking was I permitted to stand up again. Audition completed, it was back to business.

“Last chance to change your mind,” said Mandy, zipping up her skirt.

“No chance,” I replied. “I worship Tamella. Nothing could give me greater
pleasure than to prove my devotion. You’re not going to tell me I’m not good enough, are you?”

“Just making sure,” she answered. “I’ve already drawn up a contract, on Tamella’s behalf. The terms are non-negotiable. Once you sign, there’s no turning back.”

I studied the document she handed to me, my eyes making straight for the terms and conditions.

“Tamella is one of my most valued clients,” Mandy explained. “Should you fail to live up to expectations, or displease her in any way, she will instruct me to punish you in the manner of her choosing. I must stress that she is an extremely demanding mistress and I am an expert in administering pain. Unless you are a hardcore masochist, you would be well advised to tread carefully. Any questions?”

“Got a pen?”

I returned home, late that evening, braced for a confrontation with Louise. I had no intention of telling her where I would be tomorrow night and had still not managed to conceive a credible excuse.

My lover was home, but not alone. Seated on the couch, sipping a glass of red wine, was a slender and strikingly attractive girl, with closely cropped blonde hair. Though she was wearing makeup and high heels, the bulge in the crotch of her cream silk body stocking left no doubt as to her true gender. It was bad enough that Louise should taunt me with details of her infidelities, but bringing a lover home to my apartment was the last straw.

“Who are you?” I demanded.

“Chris,” the blonde replied, not in the least bit nonplussed by my arrival. “I’m a friend of Louise.

“Where is she?”

“In the shower.”

Before I could utter another word, the girl in question strolled into the room, a towel slung casually over her shoulder. She was completely naked, her cock swinging at half-mast.

“You’re back,” she greeted, obviously none too pleased to see me.

“What’s going on?” I demanded.

“I’ll leave that to your fertile imagination,” she replied. “Actually, I had hoped to have my bags packed and be gone before you got back. But Chris and I got a little diverted.”

“You’re leaving me!” I exclaimed.

“Very observant,” she smirked. “Well, don’t you have anything to say?”

If she was expecting me to beg, she was in for a shock. Since my successful interview, I felt like a new girl. She could not possibly realize how relieved her announcement made me feel.

“I shall be spending tomorrow night with Tamella Van Diemen.” How sweetly that sentence rolled off my tongue.

Louise laughed. “Of course you are, darling. And I’m going down on the pope in my next video.”

“He must be one of the few you haven’t done already,” I shot back.

“You are such a fucking pathetic little schoolgirl!” she snarled. “I don’t know what I ever saw in you.”

“Will you do something for me?” I asked, in my best pathetic little schoolgirl voice.


“Finish packing and get the fuck out of my life.”

To describe Tamella Van Diemen as beautiful would be akin to calling the mona lisa an old painting. The Dutch/American rock queen was the living embodiment of slender, long-limbed perfection. Her most notorious song, ‘Sex In Stilettos’, was the most appropriate anthem any songwriter had ever penned.

Pages: 1 2

Post your comment