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Robert's adventures as an Escort. A longer work. Part one.

 

Escort services.

 

Chapter 1.

 

At last, she allowed him to cum, letting his seed spurt into her mouth in almost painful spasms of ejaculation. Her tight grip at the base of his cock released, allowing the pent up seed to pass, so that it shot through his urethra at blast velocity.

 

His hips bucked involuntarily, raising his narrow cheeks off the stone slab of the poolside paving, his orgasm ripped through his body. Her lips, locked around his purple head, creating a seal, trapping his viscous fluids until she was certain she had it all. Then, as the small tensions subsided, she let his come dribble from between her painted lips, to run down his shaft and coalesce at the base of his shaven cock.

 

For a moment, she was quite happy to let his milky white substance, pool in the little hollow where root met body, while she held his, still rigid cock, in her mouth, savouring the after taste of his spend. Then, in exquisite and deliberate slowness, she lowered her head, taking his entire length into her throat until her lips met the resistance of his balls and groin.

 

She sucked around his girth, causing the cooling cum to pass between her lips and his cock once again, to return to the warmth of her mouth. When she was satisfied she had sucked it all back into her mouth, she slowly lifted her head, allowing his shaft to emerge from her throat and between her lips until only the very tip was all that joined them.

 

She swallowed then, her throat working the globules of seminal fluid to the back of her throat before sliding down into her gullet.

 

Chrissie stood, water cascading from her heavy, bare breasts that were swinging slightly. A lascivious smile played over her lips as she licked them clean of his residue. The shallow water came to her navel, distorting the view of her lower half.

 

It had been sheer torture for him. Chrissie, it was now abundantly clear, was an expert on prolonging the moment of release and had kept him on the edge for something like two hours. The constant erection had become uncomfortable in the end, but served to sweeten the release. He felt sure that, had it not been in her mouth, he probably would have managed to hit the glass ceiling of the in-door pool-house, so powerful had his eruption been. Mike closed his eyes for a moment’s respite.

 

In that two hour session, she had ridden him mercilessly, grinding herself against his groin, almost tearing his cock off with the firmness of her muscles. She had, had him eat her, demanding he suck on her clit and labia until his mouth ached. Throughout, she had been the controlling influence, her demands were to be met before all else, then, and only then, was he allowed his release.

 

Chrissie leaned and planted a kiss on his lips. Her tits brushed against the cooling skin of his shoulder.   He could taste his cum on her tongue as it slid between his teeth. He wasn’t sure he liked it, but with no choice in the matter, endured it.

 

His advertisement in the newspaper shop was starting to pay dividends. Chrissie was his fifth customer in the two and a half weeks since the advert went up, announcing his services as a compliant escort. He did think to himself though, that his price needed to go up. Not that he was being greedy, just that a higher price would be less attractive to the poorer end of the market, meaning that he might have a better, more entertaining evening.

 

Chrissie had been the first customer hiring him who had money and all the trappings that go with it. If he was in it just for the sex, then it wouldn’t be a problem, but that wasn’t his only motive. It would be fantastic to find a rich woman to sponsor him through the remainder of his studies.

 

Wealthier women had less hang ups too, he supposed. Guilt wouldn’t cloud the after effects of a pleasant afternoon in his company. Oddly enough, it seemed that with the luxury of money came a certain spirit of adventure. A rich woman seemed to have far more experience and a desire to have her wants attended to, than say, a woman who had to work for a living. Perhaps it was the availability of time in which to play and explore or, a greater boredom and time to fill.

 

Chrissie paid him, cash, in a plain white envelope. Neither of them hurried to dress, she preferred a silky house coat which flapped open at the front showing her enhanced breasts and surgically flattened stomach. Her wealth bought a body more in keeping with someone half her age. They left the cool confines of the pool house to return to the living room where the afternoons entertainment had started, then on further to the vaulted lobby at the foot of the stairs.

 

Mike leant forward, kissing her cheek as he opened the main entrance door.

 

“Thank you Michael.” She breathed against his ear. He didn’t correct her, knowing that she got a small, perverse pleasure, calling him Michael instead of Mike. “That was just perfect.”

 

“You have my number.” He answered, indicating his new business card that still sat, pristine, on the marble topped occasional table by the door. Her nod effectively dismissed him.

 

He stepped through into the coolness of the porch then, into the harsh sunlight of an August day. The heat hit him immediately, taking his breath away momentarily. Robert, his given name, not the professional one used on his business card, drove home to a cool shower and a study session.

 

Before he hit the music books, he briefly checked his answer phone, noticing the red light blinking. Two messages, the first from his mother telling him he was expected that Saturday, the ‘Old Man’s birthday bash’. It was hard to think of him as seventy. The other message was a little more cryptic, but then turned out to be one of the several cross dressers that had latched onto his advert, wanting to be ‘out on the town’ with a man on their arm. Robert deleted both and reset the machine.

 

So far, it had been easy to keep his two worlds apart. Lucy, his part-time girlfriend had no idea about his cash raising scheme. He had been careful to note where she would be so that they wouldn’t clash, not that it would be too much of a problem, it was a loose arrangement they shared, but it might prove tricky to explain if she saw him with different women all the time. It was though, quite tiring, having a slight effect on his progress through studying classical music. Falling asleep never endears one to the lecturer and does mean you missed the vital points of the lecture. Power Point notes just didn’t convey the real meaning of what the Lecturer was trying to get across.

 

The phone trilled. Robert realised that he had been snoozing and came back to life with a start.

 

“Hello?”

 

“Hello, is that Mike?” The female voice asked. She sounded as if she were shouting down a long tunnel, obviously a mobile.

 

Hearing his working name, Robert instantly reached for a pad and pen he kept just for these calls.

 

“Yes, Mike speaking.” He waited for her to continue, hearing a rustling, then a loud noise. The line went quiet for a second, then her voice again.

 

“Sorry, I dropped the phone.” She sounded young and nervous.

 

“What can I do for you er…?

 

“Oh! Sally, sorry. I’m a bit… um… well, you understand.” She paused. “I eh… well I need an escort for a function.

 

They talked further and made arrangements to meet for a coffee the next morning. Robert dropped the receiver and hit the books. Vivaldi wasn’t his favourite composer, finding his music a bit too frenetic for his tastes, but it had to be done.

 

Before going to bed, he called Lucy and invited her down to his parent’s on Saturday. In something of a tired voice, she agreed, said night and dropped the receiver on its cradle, cutting off any chance for a chat. He figured she had someone with her, but was too tired to be curious.



 

 

Sally looked pretty much as he had imagined her. An elfin face was framed by brown ringlets that sat atop a thin framed, narrow shouldered girl. She wasn’t unpleasant to look at, but not really his type, he didn’t go for the diminutive in a woman, preferring self assurance and a body to match.

 

She stood as he approached her table, a questioning and hopeful look in her eyes.

 

“Mike?” She stood around five feet four inches, definitely under ten stone and trembling over every inch.

 

“Hi, you must be Sally, would you like another coffee?” He asked, noting that she had emptied a large latte already. The cup looked cold, as if she had been there some time.

 

“Um sure…yes…why not?” Her nervous smile crinkled the edges of her eyes. Mid thirties he thought, single, probably a career girl.

 

“Two sugars right?”

 

“How did you… yes please.” He pointed at the sugar tubes opened on the saucer.

 

“Elementary.” He laughed at his small joke and was pleased to see she had understood the reference to Sherlock Holmes. She wasn’t entirely unread then.

 

Robert was able to study her in the reflection of the mirror behind the bar. Sally fussed with her floral dress, arranging, then, rearranging the folds as they fell over her knees. She fidgeted constantly, showing her agitation in jerky, incessant movements. Her dress hung off the shoulder with a fashionably low neck line, a copy of early sixties fashion with large flowers in red and pink printed on the voluminous material. Had she been slightly well endowed with breasts, it might have been revealing, fetching even, but on her, looked rather too much for her spare frame.

 

She had no jewellery on not even a watch adorned her body. Her fingers were very long, almost disproportionate to the rest of her hand, slender, but not quite bony. Thin wrists led to slender arms eventually lost in the dropped sleeve. Briefly, he imagined her naked, the image didn’t fire his emotions.

 

The Barista handed him his change and two milky coffees on a tray, telling him the sugar was on a stand at the end of the counter. Robert loaded the saucers with the multicoloured tubes of sugar and a wooden stirrer each.

 

“So, tell me, what’s the function you’re going to?” He placed the coffee in front of her as he sat opposite.

 

“It’s a presentation at the Lancaster Hotel. A dinner and dance event, its a couple’s night and well… I needed someone to go with…” She didn’t quite say that she didn’t have a boyfriend, but the pause filled in the blanks.

 

“…I wanted to go; it’s my first time and, well…” She ran out of words, her embarrassment painfully obvious by the flush in her cheeks and her hands wringing just below the table top. He couldn’t miss her profound shyness and began to realise just how much this meeting was costing her, his admiration for her resolve increased.

 

“What do you do?” He thought, by subtly changing the cadence of their introductions to familiar territory, she might relax a little.

 

“I’m an Accountant for a law firm, been there for a few years. Its okay, but the hours are long. I don’t get out much…” She puttered to a halt, still nervously wringing her hands in her lap, keeping her eyes downcast.

 

“…anyway, how does this work” She might be nervous, but he liked her directness of purpose.

 

They sat over the coffee and discussed his fee for the evening, when and where to meet, then, left for their separate ways with a date for the Friday evening. She had arranged for a limousine to first pick him up and then her, on the way to the hotel.

 

At seven, Friday evening, Robert locked his front door and pocketed the keys in his rented tuxedo. The waiting stretched limo drove to her address in Chelsea , a narrow mews off of Flood Street .

 

Sally looked as if she should have wings sprouting from her back. Clothed as she was in a ball gown made up of layers of diaphanous gauzy materials, her elfin looks were highlighted, giving the effect of a wingless fairy. He marvelled at just how delicate she was, realising that she probably would be a size eight or less. Her hair rose up from her face, looking like it might be supported by some kind of hidden structure before falling, unhindered to her shoulders. It had been straightened and coloured lighter than her natural brown.

 

“You look fabulous.” His compliment evinced a radiant smile which spread further when he offered her a trousseau of bright yellow orchids on a wrist band.

 

“Thank you.” She smiled into his eyes as he closed the car door, taking care not to catch her foot in its glittering shoe.

 

The food was very good, several courses ranging from game, fish, fowl and red meats, each accompanied by complimentary wine, all served by hovering, liveried waiters, in a never ending supply, it seemed.

 

Sally was to receive one of the top awards, a partnership in the company after scoring a huge deal in Australia and Singapore . She returned back to their table clutching a glass and marble trophy and a grin that threatened to split her face. The award was a complete surprise to her, adding to the thrill of the achievement.

 

Some time later, when the room started to become louder, when drink induced conversations reached a cacophonous level, Sally leaned towards Robert and suggested that they make their exit. She had downed several flutes of champagne and was somewhat the worse for it.

 

They found the limousine, eventually, the driver was leaning against the side, smoking and chatting with other drivers who were also waiting for their charges. Robert opened the door for her and had to guide her in where her balance was off by a few degrees and one hand clutched the trophy.

 

The journey to her Chelsea mews was in complete silence, even the car whispered noiselessly through the London streets.

 

“Do you want to come up?” She asked him, her eyes unfocused, peering at his face.

 

“Um, okay, I’ll see you in.” Robert dismissed the driver, telling him he would catch a cab.

 

The combination of champagne and fresh air hit Sally quite suddenly. A hand flew to her mouth as if to dam anything from spewing out. It failed. She threw up in retching heaves, managing to aim it all into a concrete flower planter. She accepted his handkerchief and wiped her mouth while trying to apologise.

 

He gently took her arm and steered her through the entrance door of her apartment block whose mews entrance belied the space behind the glass door, then, eventually to her door. Robert unlocked the door, taking her keys from her fumbling hands.

 

Sally rushed for the toilet as soon as she got to the marble floored entrance hall as another bout threatened to disable her. He found the living room and waited, listening to her retching, intent on just making sure she was okay before he left. He laid her keys on a glass topped coffee table that took centre place of her sparsely furnished apartment. What furniture there was spoke of quality, but was understated in whites or a slight variation.

 

Sally came into the living room some ten minutes later, very much better and steadier than she had been. Her eyes had cleared and the ruddiness of inebriation had gone.

 

“Look, I should go, we can have that coffee another time.” He sympathised with her distress, hadn’t he been in a similar condition himself on far too many occasions.

 

“No! Please sit, have a drink.” There was a hint of desperation in her voice accentuated with staccato movements.

 

“I um… well I had hoped you would stay for a while. I will pay the extra of course.” She stood in front of him, nervously wringing her hands, looking, for all the world, like a female version of Uriah Heap from the Dickens novel, ‘ever so ‘umble.’

 

It seemed the expulsion of alcohol had sobered her up, but allowed the nerves to return.

 

“Look, I won’t be a moment.” Without warning, she turned and fled back down the corridor, that lead off the living room. Alone, Robert sat on the nearest armchair to await her return.

 

Five minutes passed, he wasn’t sure if she had run back to the toilet or left the building like Elvis, the silence of the apartment thrummed in his ears as if he suffered from tinnitus, but at a much lower register.

 

And then, suddenly, from a separate doorway behind him, she came back into the room, a small susurration of sound the only clue he had that she had returned. Robert spun in the chair and was confronted with Sally and a complete costume change.

 

Her milky white skin was an opposite contrast to the black of a cheap harness, the type Anne Summer catalogues sell. Fake leather straps surrounded her small breasts before joining and disappearing around her back only to return much lower and join just above her pubic bone and then to split again and pass through the gap between her legs, framing her hairless pussy. A studded collar completed the entirety of her attire. That at least, looked like genuine leather and probably was originally meant for a dog.

 

He almost laughed, but managed to stifle the urge. Her nerves were shot already. His mirth would completely unmake her. Dressed, Sally wasn’t exactly endowed, but unclothed, she was quite thin, delicate even, but somehow, not angular as an anorexic might be. Nothing stuck out like ribs or hip bones, it was all just smaller than average. Naked, she had a softness and symmetry that he found rather appealing.

 

She stood, her left knee cocked in front of her right leg, closing the natural gap between her legs. Her arms hung to her sides and slightly around her back so that he could not see her hands, but suspected that she had also bought herself a pair of handcuffs. Unbidden, a mental picture of fluffy pink fur came to mind, it made him smile.

 

“Do you like?” She coquettishly tilted her head, waiting for his approval.

 

“I… um… well it is a surprise.” He smiled again and, as if that was all she had been waiting for, was almost startled at her rush toward him. She threw herself face down on the floor at his feet. He winced imagining the hurt it must have caused her spare frame as she connected with the marble floor tiles. She had indeed shackled her hands behind her back, the cuffs looked real.

 

“Take me Master,” she yelled, “I’m your’s to do with as you please.”

 

Robert was taken aback somewhat by the sudden turn of events and wasn’t sure quite what to do with her for a moment. Certainly, her earlier demeanour hadn’t given any clue to this brazen side of her.

 

He collected his thoughts and decided to play along with the game.

 

Using the toe of his patent leather shoe, he hooked her under an elbow and flipped her over. A combination of coldness from the tiles and the force of her landing on them had made her nipples stand erect. Her skin showed red where she had landed on the floor. Not for the first time did he wonder why women with tiny breasts had large nipples, large than usual. These stood prominently, coloured and darkened, as if painted with henna.

 

He rested his foot lightly on her flat stomach and peered down at her from his seated position and stared at her while he asked.

 

“So my little slave, what have you been up to eh?”

 

Her eyes flicked away from the intensity of his gaze.

 

“I have been very bad master; I got drunk at a party and threw up. I must be punished as you see fit. May I get you a cane?”

 

Fucking hell! He thought to himself, this woman is really into it.

 

“Yes you had better. Go now before it is too late.”

 

Somewhat awkwardly, she got to her knees and then stood only to rush out of the room the moment she had her feet under her and then return a few seconds later with a thin riding crop in her mouth. Again, she threw herself down at his feet, but on her knees this time and dropped the crop as a retrieving dog would.

 

He picked it up, hefting the weight in his right hand. It was no pretend thing the blackened leather was stiff except for the leather loop at the end of the braided handle.

 

“Stand up.” He ordered. She stood, trembling slightly, but whether that was anticipation or nerves, he wasn’t sure.

 

“Now lean over the arm of the chair.” She complied wordlessly, offering her milky white buttocks to him as she bent at the waist and rested on the chair arm with her feet on the floor.

 

Robert stood and surveyed her flawless, alabaster coloured skin, before swishing the crop and slapping it into the palm of his hand. It stung, but served to let him know that he would need to be gentle, if he didn’t want to hurt her.

 

He flicked the looped end, lightly striking her exposed bottom. She yelped dutifully and a small red mark showed the point of contact. He flicked at her again, hitting the other cheek. Again, she yelped and stiffened a little.

 

“Master must punish me,” she muttered, “but master must punish me hard, my sins are so great.”

 

He took the hint and smacked her ass a little harder, making sure that she felt it.

 

“Harder.”

 

His next blow was more than he would have chosen, but was exactly what she was pleading for. His subsequent blows, he aimed so that none hit the same spot, brought yells from her pleading for more and yes, harder yet.

 

Her ass was looking quite red now, but she begged for just a little more absolution. He struck her twice more, using force he knew would really hurt, but all she did was moan and thank him with each strike.

 

It was doing nothing for Robert, hitting women, even in sexual play was not his idea of a fun time, but being the professional he was, he performed to their wishes, after all, they were paying and it was their fantasies he was catering to.

 

“Stand up, slut.” He commanded. She folded her knees and managed to stand without the benefit of her hands.

 

“Now kneel on the floor.”

 

He watched as she bent one knee then the other so that she knelt upright in front of him on the floor. Her nose was approximately level with his groin. Deliberately slowly, Robert slid the tab of his zipper down, all the time watching her eyes that seemed to be transfixed on his actions. He pulled the flap of his fly to one side and with a little effort, snagged his underpants as well, freeing his cock. It unfolded and emerged into the light of the room.

 

The crop left a red welt across her breast. One more slash, another red welt pointing to her nipple across her left breast was all it needed for her to be quivering, mouth open, gasping and a light perspiration on her brow. He dropped the crop onto the settee.

 

“Now my little slave, use your mouth and make sure you do it well.”

 

“Yes Master.” She mumbled, just before his cock began to pass between her lips. Her mouth was warm and a willing recipient. She suckled on him, bringing his flaccid prick to gradual hardness.

 

He grabbed her hair at the back of her head, winding it around his fingers. Gently, but insistently, he forced her to swallow as much of his length as he dared, little deeper then, pulled her head back, only to pull her onto him again. In this way, he slowly mouth fucked her, she didn’t resist in any way. It occurred to Robert that she would probably have allowed him to spew his come in her throat. Instead, he took his cock out of her mouth and slapped her cheek with it.

 

“Does my little slave want to be used?” He waited a heartbeat for an answer then, asked, “Is my little slut ready to be fucked?”

 

“Yes sir.” Her head was bowed so her answer was quiet.

 

“What did you say?”

 

“I said, yes sir, please fuck me.”

 

“Rise slave.”

 

She stood. Robert grasped the riding crop from the settee and then, taking her arm, steered her toward the bedroom. As with the rest of the apartment, everything was white or a shade of white, in a minimalistic way, it had elegance to it. Colour came from the duvet cover, being a deep blue. He found he liked the décor but would have liked a little more furniture, possibly.

 

He guided her to the edge of the queen-sized bed. She stood, stock still awaiting his command. He pushed her forward so that she fell, face down on the bed and, before she had time to react, he lashed her buttocks with the crop, leaving a livid red welt across both, already reddened cheeks.

 

“Spread your legs.”

 

Her legs parted, but not enough for his liking, so he gave her another reminder with the crop. Her legs flew apart, exposing her pussy lips that pouted and were trapped between the straps of her harness, pushing them out. Without any force, he swiped her imprisoned lips with the crop, evincing a yelp of surprise from her. She quivered expectantly, waiting for the next lash of the whip.

 

Robert dropped his clothes to the floor and knelt between her parted legs.

 

“Kneel up.” It wasn’t easy to do, but eventually, she had her knees under her body, making her little ass rounded.

 

He felt her cunt, running finger tips over her labia and then between her lips. Her little box was red hot and ready for him if her wetness was any indication. He pushed a finger into her, making it feel as if it was done with force, but in truth, quite gently. He was mindful that she was much smaller than he and it would be all too easy to hurt her.

 

His finger was joined by another. In the position she was, with her head on the bed and her ass in the air, her lips opened for him as did her body. For a brief moment, as light hit her at the right angle, he glimpsed into her depths.

 

He expertly slipped a condom on with one hand while fingering her with the other.

 

Robert adjusted his position and shoved his length into her box up to the hilt.

 

“Oh yes Master, fuck me.”

 

He slapped her shoulder with the crop.

 

“I didn’t tell you to talk.” He slapped her again and was rewarded with a squeal of shock and delight.

 

His paced picked up. Robert was soon pumping into her, his cock getting harder as it found new depths in which to plunder her body. He lent forward, passing the handle of the riding crop in front of her until he managed to get in into her mouth like a horse bit.

 

He pulled her up, grasping the crop on either side, trusting that she would grip it in her teeth. Her new angle allowed him to push even further into her, his balls were slapping against her clit. She was grunting in time with his thrusts as her body accepted his total.

 

Suddenly, she came with a howl, but Robert was still a way off from his climax, so he continued to fuck her in this variation of doggy, still forcing her head back with the crop in her teeth. She came again, and then again, shaking as each climax smashed through her body and her cries reflected his thrusts.

 

He let go of the crop and grabbed her breasts as if for leverage and began to pump into her in earnest, driving him towards the culmination of the act.

 

“Get on the floor now.”

 

Somewhat inelegantly, he slipped backward to allow her to comply. Equally, and some what unsteadily, she managed to kneel on the floor. Robert stood in front of her and rubbed his cock, aiming it at her face.

 

“Take off the rubber slave.” She could only use her teeth; her hands were still clasped in the hand cuffs.

 

  A few more pumps on his naked cock had his come hit her cheeks and spray over her forehead and eyes. Her lips parted to allow a little to enter her mouth.

 

“Thank you Master.” She said once he had finished spraying her with his milky seed.

 

“This slave needed to be punished and thanks you for the gift of his seed.”

 

Later, after the promised coffee, Robert left her home. The sun was just creeping up over the horizon of the Thames . He was totally shattered and pleased with the extra two hundred pounds she had given him. He was also thrilled with her comments about how he had interpreted her desires so well. A job well done to the satisfaction of all parties and might well be repeated at some time in the future.

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