The Gigolo Read online

  THE

  GIGOLO

  By

  Rocky Wyatt

  Copyright © Rocky Wyatt 2017

  This book is sold subject to the condition that it shall not, by way of trade or otherwise, be lent, resold, hired out, or otherwise circulated without the publisher’s prior consent in any form of binding or cover other than that in which it is published and without a similar condition including this condition being imposed on the subsequent publisher.

  The moral right of Rocky Wyatt has been asserted

  ISBN-13: 978-1547218806

  ISBN-10: 1547218800

  Dedicated to Annabel and Alexander.

  CONTENTS

  CHAPTER 1 The Interview

  CHAPTER 2 The Agency Fight

  CHAPTER 3 The Girlfriend

  CHAPTER 4 The Whore’s Dip

  CHAPTER 5 The Geordie

  CHAPTER 6 Trudy’s Apology

  CHAPTER 7 The Proposition

  ACKNOWLEDGMENTS

  Carol for her technical insight.

  This is a work of fiction. Names, characters, businesses, organizations, places, events and incidents either are the product of the author’s imagination or are used fictitiously. Any resemblance to actual persons, living or dead, events, or locales is entirely coincidental.

  CHAPTER ONE

  The Interview

  He sat waiting for her, fidgeting, playing with his cufflinks then his tie. He looked good, or so he thought; he wasn’t a handsome man, but he was nice looking, which to him, always sounded rather disappointing. He would have liked to have been handsome, it would have made life so much easier, but saying that, he thought it was what he could do, that made up the difference.

  He was well dressed in a tailored grey suit, white shirt, navy tie and at the last minute, he’d decided on brown belt and brogues. He now wondered if he should have worn his black belt and black brogues, but he didn’t want to look too formal, too intimidating, just classically smart with a hint of fashion, not too pompous.

  He was a unique man; very good men are rare and very bad men are rare, but men that are both very good and very bad, at the same time, are even rarer – they are unique.

  He was capable, educated, and at one time a brilliant student, but that was a long time ago. His life had taken many twists and turns to be at this place, at this time, doing what he did.

  He was a little nervous, only a little though. He was his usual smug, overconfident, and cavalier self. His attitude was bred from talent, or you could say, in his case, wasted talent.

  He either irritated people or attracted them, never in between. Men wanted to either punch him or be like him; women wanted to slap him, or to sleep with him, but he never quite understood why.

  He thought back for a moment, to a sweet little compliant woman he’d known and almost laughed out loud. That had also ended badly. He sighed.

  Then he had just the ghost of a thought… Where did it all go wrong? and laughed again.

  Yes, he’d experienced most of those ‘love him or loathe him’ scenarios over the years, he’d never change now. He was his own worst enemy, he knew that. But he also knew he had to make an effort and an impression today, if he was ever going to move forward, in his life.

  He stopped for a split second. What if she...? He looked at his reflection in his mirrored wardrobe and said to himself, “No, not a chance,” whispered under his breath.

  He was a man with an irrational self-confidence and self-belief; he had a focus and a direction, he knew where he was going and nothing would stop him getting there and no one would get in his way.

  He was going ‘on the game’ or to put professionalism behind the smut, become a male escort. His professional name would be Paul Smith; it had a nice banal and gentlemanly ring to it, he thought.

  He was waiting for Trudy, an awful name, he thought, but she was the boss and she liked the thought of being ‘the director’ of ‘Summer Nights’, a moderately successful escort agency, based in the nearby city centre.

  Trudy, if that was her real name, was the archetypical ‘madam’.

  She was brash and obvious a ‘self-made woman’ with the sad mannerisms and syntax of someone who thought that, because they had a little ‘new money’, they had escaped their working-class roots and suddenly, without education or any form of cultural awareness, or for that matter any visible signs of self-improvement at all, they had, heaven forbid… Class!

  The doorbell rang, he smiled professionally and the performance began.

  “Hi, Paul… Trudy, nice to meet you,” she said, with her instant and hard smile.

  “Hello, Trudy” He kissed her, in a forced friendly way, on both cheeks. “Come in.”

  She thought that was ‘nice’; she thought he was ‘nice’.

  Straight away, he didn’t like her. He would have disliked her even more if he knew that she thought him to be ‘nice’.

  She dressed in a striped, navy blue, two-piece suit, with stripes a little too wide, the skirt, a little too short and split up one leg. She had bare legs, there was a reason for that, her blouse was cream coloured, she had black shoes, black handbag, almost black hair too.

  She was trying to look like a professional business woman about town and to the casual observer, that’s exactly how she looked, but he could see through her; for him, she didn’t quite carry the look off. Maybe it was because she was trying too hard, or maybe it was because she looked a little too hard.

  She had made her money just as she was on the slippery slope of the slide that would whisk her through her forties.

  There was so much she had missed, not had, not seen, not experienced; the rise from poverty was long and hard for her but to give her, her due, she had worked every bitter step of the way and now she could have anything, or anyone, she wanted.

  You could almost feel sorry for her, that is, if you didn’t know her.

  No, he didn’t like her, but he would have to deal with her and on a daily basis.

  He showed her into the lounge, a lovely apartment, she thought – tasteful, well thought-out, just right, and Paul fitted his surroundings perfectly.

  They talked for a while, small talk, drinking cups of tea, from cups and saucers, not mugs, which impressed her.

  They sat opposite one another, he mirrored her sitting position, back into the armchair, but cross-legged. Her skirt, of course, was split, so if he had wanted to, he could see the length of her legs - if he had wanted to.

  He deliberately looked at her eyes, but not into them, just to annoy her, which was counterproductive and self-defeating, but he couldn’t help himself.

  He told her a little about himself, subtly pointing out that he was single, divorced some years, two children at university, needing extra money for school fees, etc., etc., then onto his background, his early career, keeping it vague. She’s not interested in all that, he thought. He also thought he knew how women’s minds worked, but he was wrong with this one, she was particularly interested in all that.

  She, for her part, told him what she, the ‘director’ no less, expected from him, a would-be member of her extensive and exclusive, as she put it, staff… Loyalty, honesty, reliability, and class.

  She wanted to maintain her upmarket image, so she only wanted the best clients and the best escorts.

  She carried on with her sales blurb; he wasn’t listening, just smiling and nodding, smiling and nodding, thinking, Shouldn’t I, be selling myself, to her?

  She finished her tea and placed the cup and saucer on a side table.

  “Ok Paul, now it’s show time… she said, emphasising the cliché. “I need to see what you can do, you understand.” She was savouring the moment, letting him understand the dynamics of the situation, who was in control.

  “Of
course you do. Come this way,” he said. He was actually thinking, Oh God.

  He ushered her down the hallway to the bedroom – he went in first. He stood by the end of the bed and she stood facing him, grinning like cat with a prize mouse.

  She raised her left leg and placed it on the end of the bed and slowly raised her skirt, keeping eye contact all the time.

  The skirt, with the split, rode up easily over her thighs, right up to her waist; she didn’t wear any knickers today, this was all planned. Paul thought she must have done it a thousand times before, he wasn’t far wrong.

  She had an athletic figure – long, slim, shapely legs, a flat stomach and a freshly shaven pussy.

  She opened her legs as wide as she could, she waited for a moment, with a certain amount of pride in herself. She felt pretty good about her body, she also wanted him to see her, in all her glory and of course, become aroused, which he was and had to be, for his job.

  She then exposed herself even more, by using two of her fingers to uncover her hooded clitoris.

  “Let me see what you do with this, Paul.” She said it almost defiantly, as if it was a challenge to his manhood, but with no trace of seduction at all.

  *

  He didn’t care, he was in professional mode; that meant faking a good performance and letting the client believe they are beautiful, sexy, and of course the only woman in the world.

  Trudy knew the game, that’s why she didn’t make any amorous efforts, that was the gigolo’s job.

  He knelt down beneath her with his face, before almost touching her pussy, and then he stroked one of her legs, from her ankle, at the back, slowly, behind the knee and softly, up to her thigh. He held it there, then coming down, meeting his other hand, slowly going up, he touched her skin as if it was precious, caressing, stroking, feeling her.

  Kissing her skin now, up from the ankle, the soft skin of her inner thigh, as if he had all the time in the world, he moved his hands to the top of her leg and down the side of her other leg, but brushing it over her stomach, low, just above the pussy. She jerked, she had become more sensitive now.

  She liked the fact that he spent so much time stroking and caressing her legs, parts of her body that men had never touched before.

  He could see she was getting wet, the juice was starting to glisten at her pussy’s entrance, he knew the signs and he knew how to get the timing right.

  She was flushing a little, breathing quicker. It’ll be soon, he thought, but when I’m ready.

  He raised both arms and stroked her stomach, around and down the sides of her legs, then up the inner thighs. Her hands were on her buttocks now, ready to thrust forward.

  He touched her pussy opening and she gasped; he put a finger inside, to see how wet she was. He rubbed his fingers together, she was dripping wet and it was starting to trickle out, that always a good sign.

  He faced her pussy and slowly breathed out; his hot breath made her cry out a little, “That’s nice,” a different sound in her voice now – a womanly sound, almost soft.

  He put his two index fingers on the hood over her clitoris, lifting it up and to the side tightly, exposing the clitoris and stretching it. He licked it and she gasped and thrust forward.

  Licking slowly at first, then faster, left to right, left to right, keeping it exposed and tight all the time, now up and down up and down, left to right, left to right. He used two hands exposing her clitoris and his tongue licking it, all he could do now was to let her come, or not, depending on his mood.

  She was thrusting more, getting tense, shaking, her stomach muscles tightening, legs starting to jerk, gasping. The first orgasm was little one, but good.

  “Arh yes… Yes… Ohhh…”

  Then the second one. “Phew… Oh, that’s good…” Again, little but good.

  All the time Paul was licking up and down, up and down, left to right, left to right, keeping her clitoris exposed and tight, her juices were dripping out of her, mixed with his saliva, dripping onto his face, down his chin and onto his favourite shirt. Damn it…

  Then the biggie!

  “Woohhhh… Fuckkk… Ohhh…”

  She gasped it out, her legs and stomach jerked involuntary, he held on to her ass cheeks and dug his face into her pussy, to keep up the momentum. It wasn’t the best of positions, or the most comfortable, but for her, it was an exciting situation.

  She came good, swearing all the time, thrusting, jerking, stretching her legs wider, pulling his head and face into her greedy pussy, wanting it to last, trying to drain the last bit of her orgasm from him and her clitoris, still wanting more.

  He couldn’t see her, or anything else, from where he was, but on her face was a lusting devilish grin, that looked, well… very unladylike.

  She slumped onto the bed and lay face down, breathless, holding her stomach, she hadn’t done anything at all, but she still felt exhausted, good orgasms always drained her.

  She knew it was a good come, because her stomach muscles always ached afterwards.

  “Well done Paul,” she said, not looking at him. “Congratulations, you passed the audition, you got the job.” Ha… ha…

  She smiled as she said it, a happy smile too.

  “I haven’t finished yet,” he replied, almost curtly. She half looked at him…

  Ohhhhhhhh, she thought… anticipating more orgasms…

  Now you’re going to get it… he thought begrudgingly, knowing he had more work to do, to prove himself to the woman, and he didn’t like hard work.

  He went up to the bed and reached for her hand and pulled her onto her feet. He looked at her eyes again, coldly, and smiled. “Let me take off your coat.” It came off quickly, as did her skirt; she was naked now, except for her blouse. He unbuttoned it, taking his time, and let it fell to the floor.

  In his hand he had a blindfold, the sort you have on long-haul flights, for sleeping. He put it over her eyes.

  “This will enhance our game,” he said.

  “And what is ‘our game’?”

  “You’re the bad boss and I have to be very good and please you at the interview,” he lied.

  “That sounds about right,” she replied, but she’d got it completely wrong.

  Mmmm, she thought. This is new. She was a little nervous; she was used to being in control, but she was curious to see what developed.

  He positioned her hands in front of her and tied them with a short, red and black rope. “Stand straight, open your legs,” he said. “Don’t move a muscle, until I say.”

  She stood there smiling, not knowing what was going to happen, but enjoying the anticipation of it.

  Shouldn’t I be in control? she thought briefly. Oh well. Let’s see, shall we?

  He stood behind her and stroked her left shoulder, a firm caress; she jerked and then her left shoulder, down her spine to the top of her buttocks. He squeezed one cheek, not too hard, just enough to show his appreciation, then the other cheek, a little harder; she flinched, but it she liked it.

  “Open your legs wider.” Almost a command, she opened them wider, with anticipation.

  From behind he squeezed one breast, firmly, all over, again and again, with no rush at all, as if he was admiring his property, then he pinched the nipple.

  “Oww,” was the response from her.

  “Pleasure or pain?” He pinched it again.

  “Oww.”

  “Pleasure or pain?” He rolled it in his fingers, lovingly, then pinched it again.

  “Oww.”

  “Pleasure or pain?” Then rolled it again, then pinched it. “Pleasure or pain?”

  “Pleasure,” she finally said.

  Curiously, she could have freed herself and walked away at any time, but she didn’t, she accepted the reversal of roles. He was now ‘The Boss’.

  He held both of her nipples in both hands and lovingly rolled them, taking away any thoughts of pain, for now, squeezing both breasts and planting soft kisses over her shoulders. Yes, she liked the pleasure
best!

  He stopped abruptly, she couldn’t see him or hear him, she just waited in anticipation, not knowing what was going happen next. Her heart was already beating fast; not knowing, not being in control, made her hypersensitive.

  He stood only a foot away from her, watching, playing cat and mouse in complete control over this tied and blindfolded naked woman, who would soon be begging for his touch.

  He knelt down and stroked her leg, slowly moving his hand up her inner thigh, slowly, but taking it away at the last moment.

  “Haa!” she cried. The touch seemed so exciting, not knowing where or when it would come. This was foreplay on a grand scale: foreplay, before the foreplay.

  Then the other leg, after a moment or so, stroking all the way up slowly and down, to rest behind her knee, then kisses and a tongue over her inner thigh slowly, up to the top, but avoided any pussy contact, for now.

  Kisses and licks slowly down the other leg, stroking and kissing with all the time in the world.

  He stood up and admired her body, for a moment – it was athletic and slim and quite lovely, he thought, and he now had the power to do what he liked with it, or to it.

  He felt under her left breast with his right hand and moved to her side; he could feel her ribs. He moved down towards her groin, but again stopped. She gasped out loud – she wanted him to carry on down and make her come; he would soon have to restrain her, he thought.

  His left hand stroked her left side, down over her stomach, stopping again. He would have to check how wet she was in a moment or so.

  He turned her around to face the bed.

  “Bend over and put your hands on the bed,” he said firmly. She hesitated a moment.

  “Ouch!” A slap on the buttocks moved her along.

  “Open your legs wider.” He never had any problem controlling the situation in the bedroom.

  She bent at a ninety-degree angle, legs wide apart, and she was eager to know what was next.