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Tales From Helena Ch 02

A woman's learning experience as a paid Escort

Upon reflection, Rachel was amazed at how quickly her best friend, Staci, had embraced the concept of becoming an Escort for hire. True, the web-site disclaimers spouted on about how the client only ‘paid for the time and companionship’ of an escort and how everything else was a matter between ‘consenting adults’, but the truth was abundantly clear. The men, and occasional women, who pay for her time will be expecting to fuck her.

A couple of years ago, when Rachel had been offered the option of becoming ‘Helena’ as a means to extricating her from her own dire financial predicament, it had taken her almost two weeks of soul searching before she reluctantly agreed. There then followed three weeks of mentoring by her predecessor before she embarked on her first appointment (Chapter 1), and her own realization of just how far she was prepared to stoop to get by in the big city. Sure many of the appointments were glamorous, and it certainly dug her out of the hole she was in, but, given her middle class upbringing, she would never be able to shake the knowledge that she had allowed herself to become a ‘cunt for hire’.

In less than a year of her becoming ‘Helena’, Rachel had paid off all her debts, had money in the bank and was able to secure a steady, well paid job as a Corporate Assistant within a large Law Firm. She new her regular job was nothing more than a fancy title for someone willing to make the coffee, do the filing, photo-copying and errands, but it had allowed her to make new friends and, ultimately, find a boyfriend. For the last few months she had not bothered with making any new clients and had only ‘serviced’ the regulars out of deference to ‘Helena’. Tragically, Staci’s situation could not have come at a better time for her, she just wished it was not her best friend who was going to become the next ‘Helena’.

During this reverie Rachel was sorting through the ‘Helena’ web-site mailbox and the first Rachel knew that Staci was standing over her was when she asked, “How do you sort the legit e-mails from the crap?”

“Oh,” said Rachel with a start, “that’s pretty easy. The Web-site has an auto-responder message that replies to the first e-mail sent by a punter. Never, never, ever reply to a first e-mail request. If the punter replies to the auto-responder, which asks for more details and stuff, then you can think to start sifting through the requests. Oh, and see this box here? This is where the regular clients’ e-mails go, so always check this box first and give them priority.”

Rachel then proceeded to take Staci through the ‘rules’ on vetting new clients. New people are the scariest because they were the unknown and it is okay to be scared of the unknown because, in this case, it could save your life. The vetting process is what stops the escort from wasting her time, being robbed, hurt, arrested or even killed. Rachel took the opportunity to stress the risks to Staci so that she was under no illusions as to what she had agreed to take on. Staci’s face indicated that the lesson had registered, however, it had not diminished her enthusiasm.

“I get the risks, but, if it can get me back on my feet it has got to be worth it, right?” Staci’s expectant eyes made Rachel’s stomach tie itself in a growing guilt riddled knot.

“Staci, are you sure you want to do this? It’s not all just about glamour and sex. I’ve had some really scary experiences too.”

“What do you mean? How scary?” inquired Staci.

Rachel then proceeded to share another episode of her time as ‘Helena’.

This would be Helena‘s third ‘new’ client. She had followed the rules diligently and, just as with the previous two new clients, the third had come through with flying colours and she was expectant about another night out on the town. She had been grateful that Helena’s regulars had, over the past three months, all worked out wonderfully in easing her into the role of paid escort, however, those appointments had become rather staid or predictable. The regulars went out of their way to make her feel comfortable, catering to her insecurities and treating her with more respect than she felt she deserved. The new clients, however, had each had an air of anticipation and excitement about them. They were younger, sexier and wanted to go out dancing or to a show before getting into her knickers.

Whilst leaving the final choice to Helena, the client had asked her to be dressed to “party” and show plenty of leg. Although it was not quite summer yet, the weather was warm and, thanks to the tanning salons, her skin had an all over golden hue to it that she just had to show off. As she admired herself in her full length mirror she congratulated herself for choosing to wear the almost 60’s style Trapeze dress with a bold graphic print. The cut and flow of the sleeve-less, black & white dress flattered her 34B breasts, accentuated her slim waist before flaring out slightly and ending a seductively short 3-inches above the knee. Her long legs only seemed more shapely given the lift from the 4-inch heels on her tan coloured strappy sandals. As she slipped on her overcoat she hoped that the client, who gave the name Dave White, was as sexy as the voice on the other end of the telephone when she had called to re-confirm their booking.

Helena took a taxi Dave’s hotel, and, given the additional expense to her, she was glad when Dave agreed to pay extra for travelling expenses. When she arrived at the hotel she confidently strode towards the elevator and was pleased to see that it did not need a room key card to activate it. There is nothing worse than the suspicious, haughty looks of hotel reception staff who, instinctively, ‘know’ why you’re in their hotel but do not have the conviction to challenge you on it. She marveled at the ease with which she had adapted to her role as she walked from the elevator towards Dave’s room. She checked her watch, almost 8pm, took out her telephone to text the details of her arrival to her computer – just in case – then knocked on the door.

Dave opened the door within moments of her knocking and Helena could not help beaming her widest smile at the handsome man standing before her. He looked to be in his early-30’s, fair-haired, cut in a short, dated style that suited his chiseled features and square jaw-line, with the kind of blue eyes that just sparkled when he smiled. Even in his jacket and tie she could tell his 6-foot frame was firm and muscular and she couldn’t help the tingle of anticipation as he guided her in through the door into the reception area of his room, correction, it was a Suite. She couldn’t help but wonder why on earth a guy this hot would need to hire an escort?

“Hi, I’m Dave. I, erm, guess we should get the business end sorted first, eh?” 


All she could think of when he spoke was the actor Vin Diesel. She noted his nervousness, which helped her take control and finally dispel her own nerves. “I think that would be best. That way we can focus on getting to know each other.” She took the envelope from Dave and excused herself to the bathroom where, as quickly as possible, she checked the contents.

Matters of business done, Helena stepped out of the bathroom, gave Dave a beaming smile and removed her coat for him to hang in the closet. She felt a triumphant surge as she saw the reaction in Dave’s face. With his eyes almost popping out of their sockets, all he could utter was “Wow!”

Dave slipped a guiding hand into the small of her back as he moved toward the lounge area of the Suite. She registered a cluttered card table with three place settings, but quickly allayed her fears by confirming that she and Dave were alone in the Suite. Dave offered her a seat and moved to a bar area where there appeared to be a bottle of champagne on ice. “We have time for a drink. Any preference?” offered Dave.

“Just some ice water for now, if you don’t mind. I’m thirsty from the journey over.” Helena sat down on the couch, deliberately allowing the hem of her dress to ride up her tanned thighs.

Without taking his eyes off Helena, and with obvious lust showing itself in the bulge growing in his pants, Dave amicably replied, “Suit yourself.”

Helena could feel herself getting aroused at the thought of having this man, possibly the sexiest man she had ever been with, all to herself. After a few minutes of stunted conversation, Helena decided to take the initiative by shuffling up closer to Dave on the couch, placing a hand on his inner thigh, and asking, “Do I make you nervous?”

“Look, we’re supposed to go for dinner downstairs, but, to be honest, well, you’re just so fucking incredibly hot.” Helena smiled at the compliment, visibly relaxing. Dave leaned into Helena and they kissed as he sent an exploratory hand up her leg. Meeting no resistance, he was able to quickly push the hem of Helena’s dress almost all the way up to her waist.

It was as though a switch had been flicked. Suddenly the two of them had their hands all over each other. Helena’s breath became ragged as she both explored this man and was in turn explored by him. He seemed to know which buttons to press on her body. His lips touched and caressed the erogenous parts of her shoulders, neck, and her ears. She found herself parting her legs and grinding up against his hand as he deftly rubbed her mound before slipping two thick fingers easily past her thong and into her already sopping hole. Convinced that they were going to fuck then and there on the couch she moved her hand to the zipper on his pants, eager to free his bulging cock from its restraint.

“Just a minute,” said a panting Dave as he broke away from Helena and stood up. Her face betraying her confusion. He continued, “Let me call the restaurant, re-schedule our reservation. I’ll just be a minute so, why don’t you go to the bedroom.”

Almost dazed, Helena, on unsteady legs, went into the bedroom. She decided to slip out of her dress and was just laying down on the King sized bed when Dave, with his jacket and tie now gone, came into the room. She lay down flat on her back, seductively drawing one leg slowly up to allow Dave a clear view of her soaked thong. “Like what you see?” she said, smiling.

Dave drank in the vision before him. He knew he was going to have a great time with this sexy blonde. She could keep the heels on, but the bra and panties were about to come off. He kicked off his shoes as he slipped out of his shirt and homed in on her sweet smelling, wet, paid-for cunt. He whipped off her thong, noting the neat triangular blonde patch of hair above her wet slit, spread her legs, and started working his tongue in and around her pussy.

It only took a few glorious moments to get Helena back to the heights of passion she had been enjoying a few minutes earlier. She could not resist her body’s need to demonstrate her enjoyment by humping her mound up into Dave’s mouth, willing his tongue to explore deeper and emitting loud mewls of pleasure as he hit the right spots, driving her closer to the orgasm she knew would be coming. She wondered if other escorts orgasmed as easily as she seemed to, or would she eventually get used to the thrill of strangers taking her and no longer be able to cum. Such were the conflicts that seemed to always race through Helena’s mind.

She felt herself lifting her hips up off the bed as Dave again maneuvered his two fingers into her cunt and his tongue greedily lapped up her copious juices. Over the confines of her bra, she squeezed her breasts together and felt the rhythmic motion of her body as the fire between her legs began to race up her chest. “Oh YE-EEESSS! I,.. I’m cumming.”

It was all Dave could do to hold her in place as Helena’s orgasm peaked. Her bucking hips, aided by the leverage of the bed, almost threw him off. He couldn’t recall ever having had an escort cum like this, but, he thoroughly enjoyed the experience.

Helena felt wonderful and, although her pussy was now super-sensitive, she knew that Dave would want to fuck her. She looked down toward a man with a boyishly happy grin plastered across his face and was able to pant out the word, “Condom.”

Now fully naked and with his member suitably attired, Dave climbed up the bed toward his still flushed prey and hungrily kissed her, allowing Helena to taste and smell the sweetness of her own juices. Helena responded to his lust and, for the first time, was able to wrap her hand around the base of his rigid cock, gently pulling on it, anticipating its girth.

Dave flipped her over on the bed grunting the single word, “Doggy.” Helena complied by assuming the position on all fours and was soon rewarded by the feeling of a slow parting of her pussy lips as he filled her with his cock. He may not have been the biggest cock she had ever had, but right now it was the most fulfilling as he slowly developed his rhythm and fucked her from behind. She enjoyed the feel of his manly hands gripping her waist, pulling her down on him. She enjoyed the sound of his groin as it slapped into her and the returning sensation of lust in her loins. She told herself that she was a ‘good girl’, a victim of circumstance, but she also wanted this gorgeous hunk to enjoy fucking her, to feel as if he were getting his monies worth and to make him, hopefully, want to call her again. Her inner conflicts driving her to orgasm.

She felt his body tense, his cock swell within her channel, and heard his breathing become heavier. He was close and so was she. She needed him to last a bit longer. In her mind she began pleading for him not to stop only to hear herself shouting out the words, betraying her need again. He pounded into her with increasing abandon, forcing his cock as deep as it would go, he was now grunting, cumming and she knew that this time was not to be her time. The pace of the thrusts slackened, the thickness within her began to wither and she felt somehow cheated.

Clapping. The sound of multiple hands clapping resounded about the bedroom. A voice boomed out, “Fucking awesome, Dave. She is GORGEOUS!”

Suddenly feeling off balance, still on the bed, on all fours, she spun her head around and saw two men standing in the doorway, wolfish grins plastered across their faces. They were both similar in age and looks to Dave, dressed in smart casual attire that accentuated their physiques without hiding their obvious arousal. Dave pulled out of her aching pussy and immediately set to discarding his condom, seemingly unperturbed by this interruption.

“We got your message, man, and figured you’d be ‘test driving’ the entertainment. We got one of the Bell Boys to let us in and boy, am I glad we did,” this coming from the darker haired of the two intruders. “Mind if we join in?”

Panic stricken, Helena quickly tried to cover her modesty by retreating to the head of the bed and pulling the covers over her nakedness. Eyes agog, afraid, unable to speak, she looked at Dave.

“Look, Helena, don’t panic. Give me a minute to explain everything. Okay?” stammered Dave. “Firstly, let me introduce these guys.” Dave then quickly introduced his friends, first names only, as Phil, the darker haired one, and Steve, before telling her it had originally been planned to introduce her to the guys over dinner and see if she was open taking on all three of them. They would be willing to pay extra, but first they had to know if ‘Helena’ was as hot as her pictures, which she was. He conceded that it was his fault that he couldn’t resist her as soon as he saw her and had stalled the guys by calling the restaurant.

None of this made Helena feel any better, nor any safer. Helena decided enough was enough and indicated that she would leave, however, it was Phil who, as he pulled his erect cock from out of his pants, said, “Come on Helena, you’ve already started the party, AND you were booked for a 3 hour appointment. Don’t you think you should at least make an effort to earn what we paid?”

Dilemma. The other two guys looked unsure at this development, but Phil had the sort of glint in his eyes that gives all women nightmares. She wanted to call Phil’s bluff and just leave, but if this situation got out of hand, perhaps even involving the Police, then her secret would be out and heaven only knew what the consequences of that would be. She decided to offer a compromise.

“Look, this is not what I agreed to. I don’t do ‘parties’ (jargon speak for gang-bangs), so how about I blow each of you,” she offered tentatively before adding, “But, not you Dave.”

Bolstered by the offer, Phil countered, “Nah! How about you make us each cum once, no restrictions? Dave too, even though he’s already had a sample.”

“Just make you each cum once? That’s it? You promise?”

“Sure,” said Phil, immediately disrobing and grinning in anticipation. Each of the three men now positioned themselves at a different side of the bed. She was trapped.

“Fine,” stuttered Helena, and, in a final, futile show of defiance, added, “But no anal. My ass is not on the menu, guys.”

“Whatever,” replied Phil, ”But, in that case, hand-jobs don’t count.” He reached across and pulled the covers off her, again revealing her beautifully tight young body. “Now lose the bra.”

With her small but pert tits exposed, Dave leaned down and, before kissing her, softly said, “You’ll be fine. Just go along with the flow and you’ll enjoy it.” Helena just wanted to slap him.

The other two quickly undressed and were soon helping themselves to Helena’s body. Their hands pawed and caressed every curve of her supple body, and they began to kiss her all over. Under normal circumstances, this tsunami of attention would have had Helena worked up in no time, however, she was rightly tense, eyes darting between the faces of her tormentors. These guys were good, and patient. They were each taking their time to work this body, building up the anticipation, and drinking in her loveliness. It was almost inevitable that Helena would respond, and respond she did. Three men working her body at once, her mind racing and the implications and the possibilities. She was soon moaning her appreciation out loud.

Phil had been sucking on her right breast when he made the first move by kneeling up on the bed and presenting his throbbing cock to her parted lips. Instinctively Helena opened her mouth and took him in. Seeing this Steve, who had been lapping at her still wet pussy, climbed further up the bed, knelt between her legs and, after slipping on a condom, entered her engorged pussy and began to slowly fuck her.

Now somewhat out of the proceedings, Dave took a moment to watch as Helena groaned her enjoyment of having two cocks embedded in her at the same time. His own cock had come back to life as he took in the writhing form of this beauty and his two friends losing themselves in the moment. He stepped closer to the bed and guided Helena’s left hand to his cock. She took a hold of his growing member and did her best to masturbate him as the other two continued to pump her mouth and cunt.

Helena was already quite worked up before this latest turn of events, so it was no surprise to her when she found herself dislodging Phil’s cock from her mouth and groaning out a second orgasm. Even as the sensation of this second, deeper orgasm peaked she furiously pumped the cock in each hand and was rewarded, in the final throes, by the splattering of Phil’s hot, thick, creamy cum across her face. As she slowly came down from this latest rush she looked up at Dave and then pulled his cock into her mouth, this wasn’t over yet. Steve was still rhythmically pumping her cunt, keeping her on the boil, but she felt sure he was close.

Phil had retreated to the comfort of an armchair in the corner of the bedroom, catching his breath as he enjoyed the scene being played out in front of him. Helena was so incredibly sexy and watching his two friends fucking her was just more than he had hoped, especially since it was helping his rate of recovery. Phil had been thoroughly enjoying his blow job and then, as he saw it, “The stupid bitch finished me off by hand. She must want me to fuck that cunt of hers.”

Steve had done well to last as long as he had. The whole day had now exceeded his expectations and now he got to finish off in the sweet smelling, tight snatch of the best whore he had ever met. He now plowed into Helena with abandon and felt his cock tingle and swell with the tell tale signs of an impending explosive climax. He grabbed Helena by her waist, lifting her hips off the bed and drove deeper into her, shuddering in orgasm, filling the condom to capacity and hating that he wasn’t filling her with his seed.

Phil saw Steve finally pulling out of Helena’s swollen cunt and immediately moved to pump his own cock a few times before slipping on his condom. As he moved toward Helena their eyes locked and her body visibly tensed, however, before she could indicate any further form of protest he said aloud, “Hand jobs don’t count, remember?” He grinned in satisfaction as he saw her body relax in resignation.

Dave and Phil worked Helena’s body between them for at least another fifteen minutes before each, in turn came again. Helena, despite the attention was not so lucky. After Phil had begun fucking her something inside her switched off and she could no longer quite gain the pleasure she had, albeit reluctantly, enjoyed up until then.  


Rachel concluded the story by telling Staci that, although the guys asked her to stay longer, they had reluctantly allowed her to go as soon as she had freshened up. She conceded that, other than a sore pussy for a couple of days, she had escaped physically unscathed, but had been terrified.

Rachel also told Staci that Dave’s details were still on file and showed her a database of punters to steer clear of. She, and her predecessors had decided that there was no point in repeating mistakes of the past and that Staci should always cross reference that database against any new clients before agreeing to see them.

Rachel took some solace from the pensive look on Staci’s face as she digested this last piece of information.

“Cup of Tea?” asked Rachel as she moved away from the computer.  

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Copyright ©2009 MercianKnight as registered @ . All Rights Reserved.

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