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Tales From Helena Ch 01

Quite a long tale of a woman's decision to enter the world of paid escorting.

Rachel looked down at her best friend, Staci, and wondered just what could have happened to have reduced her to this gibbering emotional wreck. She placed the two cups of tea down on the table and then sat beside her on the sofa, wanting to console her but not knowing where to begin.

“Staci, calm down will ya! Tell me what’s wrong.”

“Everything! Fucking everything!” sobbed Staci.

Rachel put a consoling arm around Staci’s shoulders and allowed her friend to bury her tear streaked face into her cashmere sweater, immediately hating herself for worrying whether or not Staci’s make-up would ruin one of her favourite tops. “Staci, unless you tell me exactly what’s wrong there is nothing I can do to help you.”

It seemed as though Rachel and Staci had been friends forever. They went to the same school as kids, had gone to the same college, and both had made career moves to live in the city. True, they did not ‘hang out’ with each other as much as they used to, but they had remained close and had always been able to confide in each other without any fear of recrimination. They might as well have been sisters.

Staci had moved to be with her now ex-boyfriend, Mike, and had the benefit of having had a job lined up when she had moved. Staci’s bubbly personality had ensured that she was a perfect fit for the job Mike secured for her as a receptionist for a large marketing firm. It was just a shame that Mike turned out to be such an ass-hole (Rachel’s opinion) to live with and their relationship finally collapsed a little over a year ago. Nevertheless, Staci, with the moral support of Rachel, had moved on, and had even found herself a nice apartment to live in, just off from the business district – a perfect locale for work and the social butterfly Staci had become.

Rachel, however, had moved to the city on a whim, egged on by Staci. They had missed each other terribly after Staci had moved, however, with the assurance that the big city streets were paved with gold, Rachel had moved in with Staci & Mike until she could find a job and her own place. It was not as easy as the then 22 year old thought it would be and Rachel felt awful about the burden she perceived she was placing on her friend and Rachel took any and all work she could find. Waitressing, tele-marketing, and even the odd cleaning job just to earn some money. Not what this college graduate had envisaged. Nevertheless, after some 8 months, Rachel was able to move out and had gone from strength to strength ever since.

It was during this reverie that Staci lifted her face up from Rachel’s now tear and make-up stained sweater only for Staci to see the distant look and small, wry smile on the face of Rachel. “What the fuck is there to smile about?” demanded an incredulous Staci.

“Oh,” said Rachel, almost dreamily, “I was just remembering the last time you cried this deeply. Remember? We were still in school. Fourth or Fifth Form I think, and you were worried you were going to get pregnant after giving that boy, Chris, a blow-job and swallowing his cum.”

Staci’s eyes widened and, as the memory of that day hit her, she burst out laughing. Staci barely spluttered out the words, “What a dumb shit!” and they both laughed hard and long.

The pair hugged each other as they relived the memory. Their connection helping Staci to clear her head, and making it easier to compose herself for what she had to confess to her friend. They finished drinking their tea and then Rachel turned to her friend and simply said, “Well?”

Staci regaled Rachel with what amounted to a sordid tale of fiscal imprudence and attempted cover ups. Staci was four months behind on her rent, had been unemployed for over 6 months and had begged and borrowed her way into as deep a hole as one could imagine. Staci found herself slumped back on the sofa sheepishly looking up at her friend and bracing herself for what she expected would be a lecture worse than anything her parents could throw at her.

Rachel remained remarkably impassive to Staci’s revelations as she considered her response. She had to remain calm and avoid appearing judgmental because she knew that Staci’s pride was, at least in part, probably the cause of her own demise. She knew from her own observations that, certainly over the past 6 months, Staci had not curtailed any of her spending and partying habits. She also figured that Staci would never let go of that fancy apartment of hers so there was no point suggesting a down-size there, and then there was the realization that she should probably write off the money Staci owed her. So it was that, after what seemed like an interminable pause, Rachel formulated and then delivered her response.

“Staci, you’re like a sister to me, so, from this point on, no bull-shitting. Okay?” Staci nodded.

“What I don’t understand is why am I only hearing this now?”

“I was embarrassed. I thought I’d be able to get by until I found another job, but the recession and everything messed things up.” Staci went on to inform her that her ex-boyfriend, Mike, was the architect of her black-balling and subsequent dismissal from her job. She conceded to her weakness to give up her flamboyant lifestyle that had precluded any effort to put aside money for a ‘rainy day’, but her reluctance to take on jobs she deemed ‘below’ her incensed Rachel.

“I don’t know what you expect from me Staci, but, knowing what we now know, what would YOU do if our roles were reversed?”

Staci hadn’t expected that. She tried to think of something, anything as a way out, instead, realization dawned. “Oh god, Rachel. I’m sorry. I don’t know.” Tears welled up in Staci’s eyes.

“Staci, listen to me very carefully and do not speak until I am finished. Understand?” Staci nodded her assent. Rachel stood up and motioned for Staci to follow her to her computer desk and both sat down in front of the monitors screen as Rachel went through the motions of powering up her machine and logging onto the internet.

“Staci, all I can do is show you a way out. It is your choice as to what you do, but I’m going to ask that you keep an open mind and do not be too judgmental.” Staci’s face reflected her confusion as a web-site called “Helena” filled the screen. Rachel then told Staci her darkest secret.

“Staci, when I moved out of your place you need to know that I was at the end of my tether. I hated the crappy jobs I was doing to get by, I was always tired, always broke, and was really jealous of the life you had with Mike. I couldn’t seem to get a break in the job market and didn’t have the guts to admit I’d failed and just go home to my Mom and Dad.

I knew I didn’t have to move out, but I felt like a leech and thought the best thing was to force myself to stand on my own two feet. One of the waitresses I knew had put me in touch with someone who had a studio apartment for rent and, after I had told her of my dire circumstances, she took me into her confidence and showed me this web-site.” Rachel indicated the screen and clicked on the “About Me” link as she continued to speak.

“No one seems to know who set up the site, but the story behind it makes sense in an ironic way. Ownership and maintenance is passed on from girl to girl based on the need of the individual. The girl who gave it to me felt that my need was greater than hers, and in that vein I now want to offer it on to you….if you want it. It was set up on a whim by a girl who fell on genuine hard times and wanted to make some discrete money without being managed by the wrong sort. She set some basic rules, which work by the way, and set about hiring her services out as an escort. Once on her feet she was going to close the site down, however, she befriended a girl in a similar situation as to what she had been in and passed the site on to her, which is how it eventually came into my possession.

The description of ‘Helena’ is fairly generic and matches either one of us. Early to mid-20’s, blonde haired, slim, you get the drift. None of the pictures of ‘Helena’ show her face, which is just as well considering none of them are of me. In fact, these pictures haven’t changed since I got the site. My predecessor obviously gave me some guidance and mentoring to begin with, as I would with you and, as ‘Helena’, you can change whatever you want. Rates per hour, the services you’ll provide. Whatever. All you need do for now is read the site contents then we’ll talk some more.”

A wide eyed, incredulous Staci barely uttered the words, “You’re a whore?” before Rachel’s hand whipped viciously across Staci’s accusatory face. Staci was knocked clean off her seat and onto the floor as Rachel stood up, face full of rage, and glared down at her friend.

“Don’t you dare judge me,” glowered Rachel. “I did what I thought I had to do at the time. Let me ask you, are you any better for letting some unknown fuck shag you just because he bought you a few glasses of wine? It’s not like you’re some fucking saint you know!”

 

“I’m sorry. I just didn’t expect….” Unwilling to risk inflaming the situation any more, Staci simply clammed up.

Rachel’s shoulders slumped as she said, “I’m sorry too. I’m trying to stay calm as you tell me what a mess you’re in and cannot help but think what I had to do. Remember, I’m only presenting you an option here. I really don’t need the site anymore because I now have a good job that I like, my bills are all paid up and I think I’ve found someone.”

“You’ve got a boyfriend?” Suddenly the awkwardness was gone as the new important topic of Rachel’s boyfriend took precedence. The two friends chatted and found that their ties were still strong. Staci agreed to stay the night so that she could take her time reviewing ‘Helena’ and give her decision the next day.

 

*********

 

Neither girl slept well that night. Staci was comfortable enough on the couch but her mind raced with a million-and-one questions. The web-site had been an eye opener, but she was really concerned as to how she had missed her best friend’s plight, how could it drive a woman to sell her body for sex and, more unnervingly, what would it be like? Rachel’s mind was similarly wracked with conflicts that she felt sure would eventually have to be dealt with.

Breakfast was a somber affair and it was not until they were clearing the dishes that Staci finally brought the topic of ‘Helena’ up by asking her friend the simple question, “What’s it like?”

“The first one was the worst, but after that, if you follow the rules, it can be, well, er, fun.” Rachel found herself blushing at the ludicrous nature of her statement.

“Tell me about it. The first one. Please?”

 

Rachel poured them each another cup of coffee and they sat at the kitchen table as Rachel recalled the events that seemed like a thousand years ago……recalled from two perspectives.

 

****************

 

The good thing about ‘Helena’ were the regulars. They never haggled the price, were considered safe and were comfortable with the occasional change of ‘face’. They were perfect first time clients for any new owner of the site. Rachel had worked alongside her predecessor on how to vet new clients and she had done her best to prepare Rachel in that regard. Nevertheless, Rachel had, obviously, never been on an appointment before so, when the time came for the formal hand-over, her first client, Mr Townsend, who was on the list of ‘approved’ regulars, happened to make a booking and had been ecstatic to find out that he was meeting the new ‘Helena’.

Jack Townsend, a retired accountant, was a widower who had sexual needs that could not be satisfied by the genteel ladies of his generation who flirted incessantly with him at the dance socials or Thursday night Bingo. At a spritely 67 years of age he kept himself well groomed and presented in deference to Helena’s monthly visit to his suburban bungalow. Apart from meeting Jack’s sexual needs, Helena’s visits had been an opportunity to share a few hours in the company of a bright, young, beautiful and intelligent woman, however, the thought of meeting a ‘new’ Helena had set his loins on fire and, in anticipation of meeting someone new who did not know his capacity for sex, he had decided to relent to peer pressure and try a ‘little blue pill’. Jack planned to try more than his usual quickie sex romp and the occasional blow job.

Rachel smiled at Mr Townsend’s file which read like a charm. “A sweet old man, very clean, not very demanding. Loves to chat, good for a 4 hour appointment. See dress code and be nice to him.”   Her predecessor was adamant that this was an easy first timer. Rachel was now Helena.

When the doorbell rang Jack rose from his chair, straightened his creaking back and moved to open the door for his guest. Helena was a delight to behold. He showed her in and offered her a seat whilst they took care of business. “It’s quite alright, dear. I imagine you must be a little nervous, but I can assure you I have done this many times and I will do my best to ensure you have a very pleasant time.” Jack handed Helena an unsealed envelope and continued, “It’s all there, but I suggest you check anyway. Just in case.” Jack then sat down in his armchair, and drank in Helena’s beauty as she sat, demurely, on the sofa opposite him.

Helena had not been able to utter a word when she met Mr Townsend. Her heart thudded painfully fast and hard in her chest and she felt sure she would bolt for the door any moment. She took the envelope as she sat down and managed a weak smile at the sweet old man who had let her in. She saw the money in the envelope and would have stuffed in straight into her purse had he not suggested she count it. “Aaargh. Basic rule, count the cash,” she thought to herself. She grasped the chance of the distraction and methodically counted the money that signified a line that she thought she would never cross. It seemed like it was all there as she came to grips with the prospect of ‘earning’ one month’s rent on her apartment for four hours of “work”?

Jack was having some problems hiding his discomfiture as he observed Helena slowly check her envelope. Was his raging hard-on due to the effects of his little blue pill or the stunning beauty of this young woman. She seemed a little younger than the previous one, certainly taller at about five foot eight inches, once out of those sexy high heels. Slim, boobs seemed bigger and he nodded appreciatively at her straight, shoulder length blonde hair. He thought her eyes were blue, but couldn’t be sure yet given that she had not looked him squarely in the face yet. Her nervousness had given her an angelic, almost innocent facial expression that he felt bode well for the evening. Externally, she had dressed perfectly for what he wanted – the slightly prudish secretary who always hints at her sexuality – just like the secretaries in the pool at his former employer. Skirts that finished just above the knee showing enough shapely leg to feed his imagination, a blouse tight enough to show those firm rounded mounds beneath and with buttons undone to just hint at the sight of cleavage, and, of course high heeled stilettos. Perfect. He just hoped the under garments were as sexy.

Helena put the cash away and looked nervously at the client. He seemed like such a sweet man and she felt a little sorry that he had to resort to hiring escorts for company. “It looks like it is all there, Mr Townsend.” She then, quite involuntarily, began biting her lower lip.

“Jack! My names Jack,” He rose from his seat and extended a hand toward Helena. “If we’re going to be friends we neededn’t be so formal.” Helena rose and accepted his hand as he then guided her towards a drinks cabinet. “Now, I wouldn’t ordinarily suggest this, but you look like you could use a drink to calm your nerves. Wine?”

Helena’s mind screamed, “No booze! Basic rules of staying in control. No booze!”, but her face betrayed her relief and her hands were soon clasping a glass of Pinot Noir and eagerly sipping it as she got to know Jack. Judging by the bulge in Jack’s pants, she figured things were going to get interesting pretty soon.

They sat on the sofa together and as Helena sipped her wine, allowing the alcohol to calm her nerves, Jack made pleasant soothing conversation whilst all the time caressing her stocking clad knees and taking great pleasure at the thrill of being able to push Helena’s skirt hem further and further up her deliciously firm thighs. He told her how he had first met Helena, how glad he was to have found such an intelligent companion for his occasional needs and how he hoped she would come to look forward to their meetings. Despite the calming effect of the wine and the tone of the conversation, Helena still felt her heart skip a beat when, after about 15 minutes, Jack suddenly, but calmly, said, “Undo your blouse. Slowly.”

Helena put her glass down on the coffee table and complied, revealing her youthful heaving breasts cradled in a ballerina pink, lacey, uplift bra. She heard Jack’s sharp intake of breath and felt his hand tremble as it came to rest, mid way up her right thigh. She suddenly realized she had not yet truly looked at this man, so she raised her head to look him directly in the eyes, eyes that were steel grey and brilliantly alive with lust. The image of the sweet old man was melting away as she saw this rendezvous for what it truly was. This man, this old man, had paid to fuck her.

Jack was a well groomed man, around five feet ten inches tall, a trim 180 pounds, clean shaven and still with a full head of mostly fine grey hair. He was proud of his ‘discovery’ and ability to use the internet and was grateful that his still raging libido could find release via the use of escorts, however, he was still an old man, a very horny old man. The sight of Helena’s partially exposed breasts was too much for him as he clamped his now slobbering mouth over Helena’s painted lips and passionately worked his tongue into her mouth. His right hand leapt up from her thigh and moved directly onto her heaving mounds, roughly massaging her breast.

Helena was taken completely off guard and, for want of knowing what else to do, allowed Jack to assault her. She fought desperately against the urge to throw the man off her as she could taste ‘old man’ in her mouth, that stereotypical pungent aroma of the elderly suddenly encapsulated in the taste left in her mouth by the actions of Jack’s tongue. Whether the sensation was actual or psychological, it felt very real to Helena. She placed her hands against each of his shoulders hoping he would take the hint to slow it down, take it easy, or even just plain stop. He didn’t.

Helena’s left boob was soon hanging out of her bra and receiving the attention of Jack’s hungry mouth. He was worse than a teenager as his hands roamed all over Helena’s youthful body. First mashing her breast, then forcing their way up her skirt and caressing her inner or outer thighs or pulling her in by the waist as he again assaulted her mouth with his. What at first seemed to be frenetic pawing soon developed a rhythm which, to Helena’s complete shock, was having the effect of arousing her. She soon felt herself pushing back into the sofa, panting as her legs spread apart inviting this old codger to explore her intimate parts, her hands still resting against his shoulders. She could feel her pussy juices pooling, soaking her thong.

Jack paused in his assault, pleased with what he was seeing. As he started to undo his pants he said, “Take the blouse and the skirt off, quickly.”

Helena stood up, quickly discarded the blouse, undid the clasp on her skirt, letting it fall to the floor. There she stood, in front of a man old enough to be her grandfather, in her matching bra and thong set, tan hold-up stockings and her black patent 4” stiletto heels, wanting to be fucked.

Jack was only mildly disappointed that this young beauty had forgotten to wear a suspender belt, but there would always be next time, right now he needed to satisfy his urge to fuck this beauty and was more than happy to see the dampness spreading from between Helena’s pussy lips. He freed his erect member from the confines of his underwear with an audible sigh, marveling at the apparent increase in length and girth as his throbbing cock began oozing pre-cum from the eye of its deeply purple, engorged head. With a wolfish grin, Jack almost tore his shirt and tie off as he ordered Helena to lay down on the sofa.

Helena couldn’t believe how big Jack’s cock was. She never expected this old fart to be brandishing such a formidable weapon and, as she pondered this unlikely match-up she again felt the rumblings of doubt as to the situation she had found herself in. Her inexperience predicated that she would be guided by the actions of the ‘approved client’, but this man in front of her did not resemble the descriptions she had heard or read. This old fart, Jack, looked like he was going to give her a fucking she would never forget. She teetered on the precipice – should she stay or should she go? Even as she pondered the path she should take she found herself lying on the sofa, on her back, with one leg being placed over the back of the sofa, the foot of the other planted on the floor and a randy 67-year codger bearing down on her with his cock aimed directly at her wet pussy.

It was wider than she was used to but, thanks to her betraying body’s lubrication, Jack’s cock forced its way in, between the swelling lips of her wet pussy, stretching and filling her in a way that she could hardly remember. She felt his length sliding deeply into her, heard herself grunting as he began to pump his meat into her needy cunt. In a conflict of emotions she had never before felt, she was basking in the pleasure ministered by Jack’s cock whilst, at the same time, being torn by the realization she was simply a paid whore being fucked by a complete stranger. Not knowing whether to give in to her passion or cry in disgust at what she had become she felt her body tense as the tell-tale signs of orgasm rushed upon her like a freight train. “Oh dear God, no, not now!”

Jack was not expecting Helena to orgasm so quickly nor as hard as she did. Indeed, he was worried that it would be he that would cum too quickly. Nevertheless, the sight and feel of this young beauty cumming as he pounded into her relentlessly was enough to send him over the edge and he came just as Helena was peaking in her orgasm. He plowed deeply into her greedy cunt, releasing his seed deep into her womb, pumping harder and deeper than he could ever remember fucking any other woman. Helena’s arms and legs enveloped the old man, pulling him into her, all logic and guilt lost to the fire ripping through her body.

Both collapsed on the sofa, panting. Barely an hour had passed since Helena had first arrived and as she contemplated what would happen next she suddenly pushed Jack away from her, sat bolt upright and screamed at him, “Oh shit! Did you have a condom on? Did you? Oh FUCK, FUCK! Where’s the bathroom? Where is it?”

Jack sheepishly pointed in the direction of the bathroom and Helena raced off in that direction, cum dripping from her abused cunt.

 

************

 

Rachel finished the story off by telling Staci that she stayed in that bathroom for over half an hour crying, until Mr Townsend had gently knocked on the door to see what he could do to help. He apologized profusely for forgetting to use the condom and assured her that it had never happened before. He even offered to get his doctors records to show he was ‘clean’ and infertile, the latter being another reason for his loneliness.

Indeed, once Rachel had calmed down she reprimanded herself for forgetting the rules and then found herself feeling deeply sorry for Mr Townsend. He was just a man after all, and a client.

Rachel told Staci that after she came out of that bathroom she sat and talked with Mr Townsend for another hour before agreeing to have sex with him again. She had been amazed that he could still maintain a hard-on after all that had happened and that even after sucking him for nearly 20 minutes she couldn’t get that dirty old bastards cock to go down. Anyway, although she was able to avoid doing anal sex with that monster, at least this time, she spent the last hour of their appointment in a variety of sexual positions, including her favourite, doggy. And this time there were condoms used.

Mr Townsend is still a regular, but, at 69 years of age now, he doesn’t book as often. He’s one of the oldest regulars to the site, although, there are plenty of other, younger ones, that can be a lot more fun.

“Thanks, Rachel,” said Staci, “I know it must have taken an awful lot of guts to do what you did, and even more to tell me about it.”

“You’re welcome. Have you decided what you are going to do? The site is only an option, but it will get you out of that hole you have dug yourself a lot quicker than any regular job.”

“As long as you teach me the rules, I’m in.”

 

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