A Virgin's Tale

Annette leaned back in her leather chair and slipped off her expensive heels, digging her naked toes into the plush carpet. The boy sitting in front of her twitched nervously, barely out of his teens, gangly, tall, yet strangely attractive. She let her eyes drag over him, assessing him and his worth. His clothes were well-fitting and attractive, but he seemed awkward in them. She instinctively knew that when he finally spoke he would stammer, the plush surroundings of her private office making him more nervous that the establishment he was sitting in.

“As you can see, Mr Taylor we have an … impressive range of women, one of whom I am sure would delight you, depending on your particular fantasy. We do ask that you exercise caution, but we can assure you that all of our girls are … infection free as it were.”

Annette smoothed her suit jacket over her chest, pulling it down slightly to reveal the merest hint of cleavage and smiled as the young mans eyes dropped. His nervousness increased as he moved his eyes across the brochure laid out in front of him, the variety of girls in various states of undress arousing him all the more. He pointed to one half dressed in a cheerleading outfit, reminding him of the girl so unavailable in high school, her short red skirt pushed above the line of her lacy French knickers, her ample chest busting out of the tight white sweater, her eyes seducing him through the lens of the camera. He felt his erection swell beneath his suit trousers and he glanced up at the older woman sitting across the desk.

“Ah Tiffany, not her real name of course, a fellow American like yourself. Most excellent, Mr Taylor. If you’ll just excuse me, I will make the necessary arrangements.”

Annette slipped her feet once more into the painful heels, her mind wondering to the massage she would inflict upon one of her girls later, and proceeded through into a side room, swinging her hips as she did so. She picked up the phone call, hearing the honey tones of Kerry, otherwise known as Tiffany to her clients, on the other end. She waltzed back into the office containing the nervous James Taylor and directed him to the room where Tiffany was ready and waiting.

~*~*~*~

Kerry sighed as she lay back on the bed waiting for her latest client. Being the cheerleader fantasy meant she normally serviced older men looking for a younger girl, and as she lay waiting, she pulled aside her French knickers and flicked a finger over her clitoris, to give the impression that she was turned on. She was paid to make men feel desired, and she pictured her madam’s naked body gyrating on top of hers and she slowly slid one finger into herself.

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The tentative knock on the door flung her from her fantasy, and she quickly rearranged herself on the bed, and called out huskily for the client to open the door.

The person who entered was barely more than a boy, probably 19 to her 20. He was tall, gangly, and she imagined he would speak with a stutter and when he muttered out his hello she was barely surprised to discover he was American. They always chose her, especially the geeky types, the ones for whom she was their ultimate fantasy, a flashback to their childhoods in a fairly freaky way. He was younger than her usual clientele, but fairly cute. Maybe she wouldn’t have a fake her desire for him this time, something she was used to with he *much* older clientele.

He was nervous, his hands and voice shook and she drawled out a question

“First time?”

He nodded, thinking she was so correct in more ways this one, this epitome of his desire, stroking her barely contained breasts, turning him on, making him harder if it was even possible.

“Come join me sweetheart” she continued, patting the bed in a practised yet alluring manner. He sat down, making the bed shake and she kissed him, softly, her tongue deftly slipping between his parted lips and pulled his jumper over his head before he could catch his breath. She undid his belt and jeans, sliding them down over his narrow hips, catching them on his large erection, pulling off his socks and shoes all in one motion. She cupped his cock in her small hand and gazed into his widened eyes, his virginity written on his face and she smiled to herself.

Virgins were always more fun.

“Shush, sweetie, relax, let Tiffany take care of everything” There it was again. That slow, sexy half smile, highlighting a dimple in her cheek. He thought he loved her in that moment as she straddled him, taking off her sweater, unclasping her bra and he gasped as her heaving breasts spilled free. She pulled down his boxers, before taking off her skirt and lacy red French knickers. She straddled him stroking his erection with one hand, the other dipping two fingers into her own soaking pussy, rubbing the heel of her hand against her clit.

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“Ready?”

He nodded mutely, half disbelieving that this beautiful blonde cheerleader was about to take his virginity from him. She slid down, moaning as the head of his cock first slipped into her welcoming wetness. She slowly continued, gasping as she took his whole length and she stayed still, holding him close inside of her, gazing into those widened blue eyes and she smiled again, before rising up again, putting her well toned thighs into good use as she sunk down again, slowly, rising up then down, becoming faster and faster, breasts shaking, smiling as he closed his eyes in desire, watched as his breathing became faster and faster, as she rode him, her own movements becoming a blur, as he shuddered, pushing his hips up into her, she gasped as he slid deeper as he came, hard, twitching as he released the last of his cum inside of her.

She dismounted, smiling a full smile this time as she looked at him, eyes closed, face flushed, breathing still heavy. She stood up and threw a towel over his naked body.

“Shower is through that door on the right.”

She left through the door on the left, and stepped into her own shower, rinsing the smell of him off her, when she realised she didn’t know his name. It was not normally something that bothered her, but he clung to her, even when she was rubbing herself down afterwards, stroking her hard nipples and flicking her finger over her clit, rubbing herself to her own shuddering orgasm.

Updated: April 16, 2018 — 3:29 AM

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