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Tales From Helena Ch 03

The third chapter exploring the fictional (mis)adventures of Escorts for hire
The third chapter exploring the fictional (mis)adventures of two young women who, for their own reasons, had decided to work as an independent Escort for hire. Please read the previous chapters first to fully appreciate this next installment.


Rachel was furious. After all she had said, Staci, her best friend, had ignored her advice and had booked an appointment to see a new client on her own initiative. It had been barely a week since Staci had pleaded for Rachel’s help and Rachel had, reluctantly at first, revealed the existence of the ‘Helena’ web-site. Rachel felt Staci was rushing into the unknown and could get hurt both physically and emotionally, however, a part of her also knew that her best friend’s stubborn streak was going to make any possibility of her changing her mind unlikely.

“Look, Rachel”, insisted Staci, “I’ve followed the rules and this one looks like a piece of cake. Anyway, I’m a big girl now, so stop fussing over me.” Staci’s face reflected her grim determination to do things her way and on her terms. She was in a bind, financially, and she fully appreciated her friend’s concerns, but Staci just wanted to get her life back on track. Staci hated being broke, and refused to accept the possibility that she may have to compromise on the life style she had decided she was entitled to. So what if she had to fuck a few strangers every now and then to pay the rent, she’d soon be back on her feet and would just put it down to experience.

“Let me see,” said Rachel as she read the e-mail correspondence and details of the appointment Staci had agreed to.

The request for an appointment was from a new punter and had first come in about a week before Staci’s knowledge of Helena, however, it had already passed the first screening test by then. Rachel had simply decided not to follow up on the request but had left it in the ‘Pending In-Box” where Staci had obviously picked up on it. Staci seemed to have done all the right things as far as vetting processes go and, under normal circumstances, this is one prospect Rachel would have followed up on. Nevertheless, Rachel was worried that Staci was not ready.

“Fine,” barked Rachel, “suit yourself, but I’m coming with you on this one and if ANYTHING seems out of place then you bail and leave. Understood?”

“Rachel, it’ll be fine. The guy checks out. He’ll be in town on business and just wants a pretty lady for a dinner-date. Four hours. Dinner followed by an hour’s private time. It’ll be a breeze.”


Staci couldn’t help but smile at her image in the mirror as she marveled at the sudden bout of nervous excitement that had released a swarm of butterflies in the pit of her stomach. Staci acknowledged that she had led a somewhat charmed life and only played according to her rules, however, she resented that some people considered her reckless at times. She preferred thinking of herself as ‘adventurous’ and totally in control of her own destiny. She would soon be back on her feet again and show all those who doubted her ability to succeed.

Staci had been a little alarmed at the choice of restaurant the punter had selected, but then she reminded herself that there was no way he could have known that the establishment was one she had used to frequent, very occasionally, a while back. It was unlikely that she would bump into anyone she knew and, even if she did, there was nothing wrong in meeting a friend for dinner. It was because of this train of thought that she had decided to tone down her intended attire for her first night as a paid Escort.

She turned sideways to the mirror to admire her form. “Lucky bastard,” she thought to herself as she considered the good fortune this punter had had in choosing to visit the ‘Helena’ web-site. She had chosen to accentuate her 120lb, 5 foot 4 inch slender but curvy frame, with a smart ‘business’ ensemble. Her thick, wavy blonde locks fell loosely over the high collar of the pale blue, classic summer shirt. She had folded the full length sleeves to about ¾ length and kept the top three buttons undone to provide an enticing edge to an otherwise conservative look. The barest glimpse of the light blue scalloped lace edges of her demi-bra was intended to tease. Rachel’s suggestion that she wear a business suit had at first galled her, however, once she had eyed Rachel’s grey pin-stripe suit with figure hugging pencil skirt that finished just above the knee, she was sold. Barely black hold-up stockings caressed her slender legs, which were made all the more shapely by the 3 inch stiletto, patent leather, Aldo pumps that completed her outfit. She felt deliciously seductive and couldn’t help licking her lips in anticipation of the night ahead.


“Stephane’s” was an up-market steak house located on the ground floor of a major, city centre hotel. In its day it was bustling with affluent young brokers & bankers who were ready to flaunt their cash to willing women on the chance they could whisk them away to an upstairs room for more intimate fun and frolics. The changing face of the financial landscape had tempered the spending habits of the clientele to the point where the establishment had returned to a more conservative, but still higher spending customer base. It was into this more refined atmosphere that Staci and Rachel arrived, looking for the gentleman with whom Staci had made her appointment. They failed to notice the interest engendered by their arrival by a rather rugged, stockily built man who was just finishing up his meal in one of the quieter corner booths.

Neither Rachel nor Staci could quite believe it when the punter, who only gave the name of ‘Nigel’, had suggested that they meet at the bar of the restaurant and that he would be clearly identified by the yellow rose he would be carrying. Both girls could hardly believe that there were any old school geeks left in the world, however, there he was and it was all they could do not to burst out laughing when they saw him. Indeed, the sight of Nigel so diffused the tension between the girls that Rachel could only slap Staci, now Helena, on the shoulder as she turned to leave, saying, “I think you can handle this one after all.”

Nigel never saw Helena arrive, so she had time to compose herself as she made her way toward him and to fully assess her ‘date’.

Nigel was a scholarly looking man who, facially, looked no more than 25 years old, despite being 36 years of age. His thin fair hair, parted from right to left, and his unfashionable wide-rimmed glasses atop his hawkish nose gave his long thin face a perpetual look of youth. What made his appearance more ridiculous to some was his pale, almost translucent white skin, and thin wiry frame which he had, inexplicably, decided to adorn with a camel coloured, double breasted suit with overly padded shoulders. Indeed, as Helena closed in on the hapless fashion disaster, she couldn’t help but liken him to a kite in the way his ‘stick’ frame supported his jacket. “Heaven help him if he decides he wants to walk out in the wind,” thought Helena.

So, it was pretty easy for Helena to break out a broad, welcoming grin when she made eye contact with Nigel and they greeted each other. Both Helena and Nigel, for their own reasons, struggled with the pleasantries, however, Helena took the lead and reminded Nigel that it should always be business before pleasure. This prompted him to apologise as he clumsily handed Helena an envelope containing her fee.

As Nigel watched Helena check the contents of the envelope he could hardly contain his delight at the vision of beauty before him. He had never hired an escort in this city before and certainly not one that exceeded the claims of beauty made on their web-sites. This trip had already been a huge business success and now, it seemed to the introverted bachelor , that his celebrations would exceed his expectations. He felt his cock stiffening in his pants at the anticipation of the evening ahead and then reprimanded himself for staring too intently at Helena. It would not do to unsettle her. Girls like this always laughed at his adoration of their form so it was best to remain aloof and humour her with the expected inane grin that geeks were supposed to wear. He took a quick lecherous look at her lithe body before reaching out toward her proffering the yellow rose he had been clutching in his now sweaty hand.

As she finished quickly counting and marveling at the monies in the envelope, Helena saw the motion of Nigel’s hand toward her and looked up. She couldn’t help but think, “What a geek. I’ll bet he’s never been laid before, poor lad”. She hoped that her eyes were not betraying her thoughts as she accepted the rose from him. “Thank you, Nigel, that’s very sweet of you.”

“This is a big day for me and I’m so glad I won’t be celebrating it alone. I hope you don’t mind, but I’ve ordered aperitif’s and champagne to start before we sit down for our meal.” Nigel motioned to the barman who deftly placed a chilled bottle of champagne next to two empty glasses that were already next to Nigel before disappearing out back, presumably to fetch the snack food. Nigel popped the cork on the champagne, poured a glass for Helena and handed it to her before pouring a glass for himself.

Helena considered refusing the drink, however, it was champagne and the cork had just been popped. She knew the rules about drinking with the clients, however, this was a ‘dinner date’ and she was sure she could handle her booze better than the stick insect she was with right now. She took the glass, gave a hearty “Cheers, Nigel,” and sipped her drink.

By the time they sat down to their meal, both Helena and Nigel seemed more relaxed and began to engage in cheerful banter. Indeed, Helena’s confidence levels seemed to be mushrooming as she grew into her role and she felt almost giddy with excitement at her future.

Feeling the effects of the champagne more than she thought she would, Helena excused herself from the table mid-way through the main course and made her way, on surprisingly unsteady legs, to the ladies bathroom. She cursed herself for drinking too quickly on an empty stomach and hoped it would not ruin her evening.

As she returned to her table, her head a little clearer, she saw Nigel talking with another man who seemed to be bent over whispering in Nigel’s ear. Through slightly foggy vision she couldn’t quite make out who the mysterious stranger was, but, as she got closer, she could see that Nigel’s face was ashen. Before she got any closer the man moved off toward the exit and had left the restaurant before she had sat down.

“Who was that?” asked Helena.

“I…I don’t know. He just came over here, stinking of beer and muttering something or other about how lucky I am. I told him to go before I called the Police. Drunkard!” Helena smiled at Nigel and dreamily thought, “He may be a geek, but he was a sweet geek.”

Nigel suddenly stood up from the table and said, “Helena, I know it’s early, but let’s retire to my room upstairs.” He then took Helena by the arm and led her away from the restaurant, towards the hotel lobby elevators and to his room.

Helena merely complied and only fleetingly considered the fact that they had not even finished their meal and they still had about two hours left on the date.


Nigel had never been lucky in love but he had been inordinately successful in business. This had meant he had been able to pursue his sexual needs by buying the favours of women and, as a consequence, he had developed a twisted sense of morality. Now he was taking the best looking whore he had ever bought back to his room for some well earned relaxation.

Safely ensconced in his room, Nigel stepped away from Helena and said, “Take off your suit.”

She complied, disconnectedly looking at his frame as they each began to disrobe.

Whereas Helena was a vision of sexuality in her matching bra and thong, her stocking clad legs revealed in all their glory atop her high heels, Nigel looked even more ridiculous naked. His disproportionately huge, erect, throbbing cock jutting out from his straw-like build of a body conjured up the image of being able to grip him by his tool and then spin him like a propeller. Helena raised a hand to her mouth in a futile attempt to suppress a snigger at the thought.

Nigel’s eyes drank in Helena’s beauty. He said, “Your web-site states you offer a ‘full service’ girl friend experience. Is that true?”

“I guess”, replied Helena.

“Good, because I need you to get down on your knees and start showing me what a good cock-sucking whore you are.” Nigel parted his legs slightly and then pointed emphatically down at his throbbing cock. “Now.”

Helena briefly considered how rude Nigel had become before finding herself kneeling before his twitching member and taking it by the base as she fed its girth into her mouth. Her fingers could barely get around his thick member and, at what must be at least 9 inches in length, it was a little more than she was used to, however, she felt that she needed to know how it would feel. She worked her mouth and tongue over and around the engorged, angry head of this monster whilst pulling down on its base with her left hand. Soon she was swallowing his cock in a deep, slow rhythmic motion, gradually taking more of its length each time.

Nigel looked down, with a deep sense of satisfaction, at Helena and knew that this one really knew how to suck cock. It pleased him to see her slip her right hand under her thong as she obviously felt the need to please herself. Even though she had not yet been able to take his entire length in that sweet mouth, she was good at giving head and would soon make him cum. He grabbed two fistfuls of her flowing hair and pulled her head further down onto his cock causing Helena to initially gag at the sudden force of his cock momentarily hitting the back of her throat. Nigel pulled back briefly before beginning a steady, but firm, fucking motion of Helena’s mouth. He soon built a rhythm, mercilessly pounding her mouth with his cock and was overjoyed to see that Helena did not seem to miss a beat as she accepted the face fucking he was giving her. He rammed his cock in and out of her accepting mouth as he felt the knowing tingle at the base of his groin signaling the on-coming tide of sperm about to be let loose.

Helena could feel the tell-tale signs that Nigel was about to cum and, instinctively, she knew she should pull this strangers cock from her mouth, however, she could not summon up the will nor the inclination to do so. The pounding became frenetic as she heard Nigel issue a guttural, “Urrghhhh! Take it all you slut,” and felt the warm torrent of his salty seed gush into her mouth and force its way down her throat. She swallowed what she could and then gagged, unable to remove the Nigel’s cock as his final harsh thrusts signaled the peak of his orgasm, and feeling the excesses of his cum squeezed out from whatever gaps around her lips it could find and drip down over her chin.

Panting, Nigel’s pace slowed as his member partially withdrew from Helena’s mouth, allowing Helena to draw breath. She still held his shaft in her hand and obliged him by pumping it a few times to extract every last drop of his seed into her mouth. She took his softening cock from her mouth and looked up at him.

Despite the sticky mess now around her mouth, Nigel still thought she was the sexiest woman he had ever had. “Stay right there,” he ordered as he quickly produced a digital camera and commenced taking a series of pictures of Helena knelt down before him with his cum still dripping from her mouth. “For posterity, my dear. You don’t mind do you?”

Helena merely shook her head.

“Good.” Reaching into a dresser drawer Nigel then produced a rather large vibrator which he threw onto the bed. “No need to get cleaned up. Lose the bra and panties then get on the bed and let me see you using that dildo whilst I watch.”

Inexplicably, Helena did as she was told. In an almost out-of-body experience she saw herself sprawled out on the bed, legs drawn up and the lips of her shaved pussy parted to reveal her wet, dripping gash. It was as though she could sense, rather than feel, the throbbing of the vibrator as it passed in a circular motion over and around her clit. Within minutess the head of the vibrator began dipping into her hole, always rolling over her clit, her hips began rising up to meet its thick, ribbed rubber girth. Her body bathed in sensual erotic pleasure as she expertly wielded the vibrator, going deeper and deeper into her now swollen and needy cunt which coated her new toy in her essence. Time stood still as her pace quickened. She was finding it hard to breath, her heart raced, it all felt so good that she never wanted it to end, and then what seemed like the bright lights from an on-coming freight train rushed upon her and she felt her body explode. Her back arched, she buried the vibrator deep within herself, still thrusting and let out a long, lustful howl of orgasmic pleasure before collapsing, covered in sweat and panting on the bed.

And all the while an incredibly happy Nigel continued to take his pictures and, unbeknownst to Helena, his videos.

Nigel looked upon the sweating, panting heap of Helena, pleased with the evening so far. Thanks to her amazing display, his cock was rigid and ready for round two. “Okay slut, my turn again.”

Nigel guided a dazed Helena up off the bed and positioned her over the back of an armchair forcing her to support herself by placing her hands on the arms of the chair and leaving her ass jutting up in the air. She looked back up at Nigel and, gratefully, saw him slip on a condom before positioning himself between her spread legs and slipping his huge member deftly into her slick, puffy hole. Perversely, she was glad she still wore her heels as it allowed her to, more or less, comfortably drape herself over the back of the chair and, although her vagina was somewhat sensitive after her exploits with the vibrator, the toy itself had more than loosened her up thus enabling her to tolerate this latest assault. She felt him slip inside her, filling her up and coating him with her abundant juices. After a couple of gentle, deep thrusts she found herself beginning to enjoy herself again and began to push outward in rhythm to meet his thrusts.

“That’s a good slut,” Nigel remarked, “I always find it easier if I get you to lube up my cock before a good ass-fucking.”

Before his remarks had even registered Helena found herself gasping at the pain of Nigel’s sudden assault on her puckered ring. It was not that she was an ass-virgin that caused the pain, indeed, she actually enjoyed anal sex on occasion, it was the lack of any warning or preparation. Despite being heavily lubed, Nigel’s condom covered cock was forcing its way into a dry ass that was not relaxed in any way to accept the invasion of his huge member. She felt her ass try to resist but to no avail. Her position over the back of the chair precluded any significant howls of protest and she was unable to stand upright because of the pressure on her back from Nigel’s hands.

Nigel was in heaven. He knew, as soon as he’d seen her ass, that that hole was one less travelled and that he would take that hole rather than the whore’s well used cunt. As he fucked her in the doggy position over the chair he could not help but focus on her puckered ass ring and, once he saw that Helena was worked up again he pulled out of her cunt, lined up his cock with her ass and just rammed it in. Helena’s ass was just as tight as he had hoped and he forced his cock past her sphincter and, once in, began a steady, forceful humping of her ass. Driving a little deeper each time, and watching Helena writhe and moan her protests at this invasion, gave him immense satisfaction. This had been money well spent.

Before long, Helena began to relax and even gleaned some enjoyment from Nigel’s fucking of her ass. His strokes were deep but his rhythm was steady and pressing her erogenous buttons, particularly the feel of his balls as they slapped up against her still sensitive, puffy pussy lips. Her ass had never felt more stretched and full and she was sure the skinny bastard would be fucking her for a good while this time, so she resigned to enjoy the moment and, if she were lucky, have another orgasm. She closed her eyes, began to push back into his groin again and let her imagination take her to a much better place with a much better looking date.

Even though he had already cum once, it would have taken a man far better than Nigel not to be overcome by the delicious feel and sight of a stocking-clad Helena bent over a chair being fucked up her ass. With the sweat streaming down his body, his heart about to explode from his chest, Nigel, finally let go and filled his condom to capacity as he buried his cock, up to the hilt, deep within Helena’s ass.

Helena felt her own, less intense, orgasm sweep over her as she felt Nigel’s cock swell within her followed by his animalistic grunts and thrusts. The depraved part of her soul wished she could feel his cum gushing into her, coating her insides, whilst another part of her screamed its disgust at what she had allowed to happen over the last few hours.


With the celebrations complete, Nigel allowed Helena to freshen up before ushering her out of the door. As he watched her walk, unsteadily, toward the elevator he looked contemptuously at the beauty and wondered if he would ever see her again. Although he couldn’t understand why women would allow themselves to be used this way he was glad they existed so that he might satisfy his needs.

With a shrug of his shoulders he returned to his room and began to pack his bags ready to leave the fictional personae of Nigel behind.


The next day Staci confided in Rachel every detail she could remember of the appointment and was in floods of tears by the time she had recounted her depravity. She couldn’t understand why she had been such a total willing slut.

Rachel looked at her friend and thought, sadly, “Lesson learned.”

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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