Lesbian Gigolo Read online

  Lesbian Gigolo

  Daphne DeChenne

  Paulba Press * Los Angeles

  Copyright © 2014 by Daphne DeChenne

  All rights reserved.

  Published and printed in the United States of America

  No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopying, recording or by any information storage or retrieval system, without written permission from the author.

  CONTENTS

  Samantha At Night

  CEO Laura

  Therapist Swanson

  The Business“man”

  The Swingers’ Club

  Camille

  1

  Samantha at Night

  Everything, everyone, the whole world seems so far away, Samantha observed as she smoothed back her short, wavy dark hair, pulled on her snug black motorcycle jacket and prepared to return to her place among the millions of twinkling city lights below. Atop the highest hill in Kenter Canyon, north of Brentwood, she could see the vast expanse of Los Angeles – from downtown to the Pacific Ocean and beyond. It was too bad that the resident of this plush, palatial home with its Gods-eye view was too immersed in private misery to fully appreciate and enjoy all that she had. The 10-15 year old “Best Director” statuettes spanning the length of the mantle reflected a faded glory that was little consolation to Kate, their recipient. Samantha was part of that consolation, however, and she understood her role even more clearly as she gazed in silence upon these perpetual reminders of better days.

  “You almost forgot this,” Samantha heard the breathy voice whisper, as she simultaneously felt full, warm breasts press against her back, and arms wrap around her waist.

  “Now how could I have lived without that?” she replied sarcastically while taking the large, freshly-used strap-on from Kate’s delicate hand. Sam turned around in the confines of silky-robed arms and gently, but passionately, kissed Kate. “I’ve gotta run, but you’ll remain in my thoughts, beautiful.”

  “Same time next week?” Kate cooed as she slid a wad of bills into Samantha’s free hand.

  “Same time,” Samantha responded, while slipping the money into the interior pocket of her jacket. Using the same hand, she then grabbed Kate’s crotch firmly and maintained a tight grip while whispering, “Save this sweet pussy for me, baby. I can’t wait to have more, and I don’t want to share with anyone.” After another, more passionate, kiss, Samantha threw the strap-on in her leather bag, tossed it over her shoulder and left “Director Kate’s” house.

  The miles-long winding drive down Kenter Avenue to Sunset Boulevard took Sam past some of the most expensive real estate in Los Angeles County. Although she was perfectly happy with her sporty, black, three-year-old Acura RSX, she found herself occasionally envying the owners of the high-end Mercedes, Jaguars, Bentleys and BMWs in the driveways. She loved their cars, but didn’t particularly envy their lives. In her relatively short 28 years on the planet, Samantha had discovered a strange but consistent positive correlation between wealth and misery. The most wealthy were some of the most troubled, lonely and sad people she had ever encountered. As she contemplated this thought and simultaneously arrived at the Sunset Blvd stoplight, Samantha reached inside her jacket and pulled out the cash Kate had given her. Her rate was $300 per hour, or $200 per half. She counted out $500 even though Kate had only booked her for, and she had only worked, one hour. Kate was always a generous tipper, and the money was coming just in time to cover rent for January. Samantha breathed a sigh of relief, turned left onto Sunset and cruised through the pre-dawn, traffic-free streets back to her Hollywood Hills-adjacent apartment.

  Four clients in one night had Samantha feeling more than a little drained and she couldn’t wait for her head to finally hit her own pillow. She loaded the tools of her trade – strapons, dildos, ball-gags, beads, clamps, etc. – in the dishwasher and set in motion the cleansing process that prepared them for the next night’s work.

  Samantha perused her appointments for the coming day. Wednesday was dawning, so there would be the weekly afternoon oral pleasuring of CEO Laura, followed by a legitimate therapy session with Therapist Swanson. Then back to sleep before two additional high-kink clients later that night.

  The wall clock registered 5:36 a.m., and as her head rested on her soft, inviting feather pillow, she set her mental alarm for five hours. Like an athlete preparing for a big game, Samantha visualized her next client encounter with CEO Laura. Laura runs her 5,000+ employee company from a penthouse atop one of the tallest high-rises in downtown Los Angeles. Every Wednesday she conducts her “State of the Business” company-wide meeting via Skype from her penthouse office … with Samantha secretly conducting business of a more erotic nature beneath Laura’s desk and between her legs. The meetings generally last between 20-30 minutes, and Samantha receives more pay if she can make Laura climax before they end. She smiled as a sure-fire way to please this impressively hot boss came to mind, and was quickly lulled to sleep by the distant whir of drying sex toys in the dishwasher.

  2

  CEO Laura

  “Hi Carly,” Samantha smiled at the gorgeous young redhead who greeted her at Laura’s penthouse doors. “I’m here for the weekly meeting,” she added unnecessarily.

  “Yes, she’s ready for you,” Carly replied in her distinct Southern accent. “Go ahead and go on in, Ms. Chase.”

  As she walked to Laura’s office and shut the tall, solid wood doors behind her, Samantha wondered if Laura had hired Carly for her innocence, her beauty, her corruptibility potential, her phenomenal tits, or all of the above. Whatever the reason(s), she didn’t blame her.

  “We’ve projected revenues for the next six months and we expect them to be less than those of the prior six months,” Laura intoned into the webcam relaying her image to her Sr. Vice President of Sales, as she waved Samantha to her desk. “Listen Ted, the meeting starts in five minutes. Let’s continue this conversation then with the others. I’ve got to sign off right now.”

  “Okay, I … “ came the response from Ted, before Laura disconnected him and turned her attention to Samantha.

  “Come here, baby,” the late-30-something sexy exec growled in a low voice, and Samantha obeyed.

  As soon as Samantha came within arm’s reach, the still-seated Laura reached out, grabbed her tits and said, “I see you’re wearing the top I bought for you. I like that. I like it a lot.” She squeezed Samantha’s breasts even harder through the shirt and then slapped her on the ass.

  “Good girl!” Laura added as she stood up. She straightened her blouse, skirt and pearls and ordered, “Now assume the position, sweetie. The meeting’s about to begin.”

  Samantha slipped off the Ferragamo heels she wears exclusively for this client and moved effortlessly into her familiar position on a plush pillow under the desk and directly in front of Laura’s chair.

  “Welcome, everyone,” Samantha heard Laura say into the webcam above as Laura’s spread legs approached her face. “Let me start by saying, no one at this point can predict what is going to happen econimically in the near-term, but my cautious view … “ The sound of her voice trailed off as Samantha gave her full attention to the duties at hand. She quickly pulled her snap-button top open to reveal her 36-B’s. Sam’s breasts were surprisingly soft yet firm, considering her more muscular, athletic build, and Laura adored them. One of her favorite forms of foreplay was having Samantha rub Laura’s bare feet all over her tits, which Samantha was now doing. She licked and sucked the toes of her right foot while rubbing the bottom of the left one over her nipples, and around and between her breasts. She kissed the inside of her ankle, up and down, then moved her kisses further up Laura’s leg to the bac
k of her knee.

  Samantha knew time was working against her, so she advanced to the hemline of Laura’s skirt and pushed it gently upward. As Laura continued conversing with her minions, Sam moved her fingers lightly up her inner thighs, gently caressing but not probing per pantiless pussy. She felt the boss’s legs quiver and knew she was on the right track.

  “We are turning our attention now to the future and recovery. This means … “ Laura continued, as she moved forward in her seat to further expose herself to Samantha. Her employees interpreted her shifting body language as a sign of enthusiasm and interest. Which it was.

  Samantha took the cue, pushed her hands under Laura’s skirt until she had an ass cheek in each hand and thrust her face into the tantalizing and wanting muff in front of her. She ran her tongue over and around Laura’s erect clit and, using just the tip of her tongue, she flicked around and just inside her increasingly-wet vagina.

  “At the end of the day,” Laura continued, “what happens abroad impacts us … “ With Sam’s tongue now probing deep inside Laura’s pussy, she reached with a free hand to retrieve a dual-vibrator from the leather bag next to her. The vibrator was curved at the base and a second, smaller, anal vibrator protruded underneath. Samantha briefly pulled her face from between Laura’s thighs, gently inserted the vibrator and turned it on low.

  “Wo! Uh … I mean, we had several converations with … “ Laura responded as the vibrator began to work its magic. Samantha smirked and started suckling Laura’s clit as she slowly increased the speed of her vibrator thrusts. Laura’s thighs suddenly clamped hard against the sides of Samantha’s head as the meeting continued: “… and at our annual review on Friday … “

  Samantha pressed harder and harder against Laura’s strong thighs to suck and lick her clit while probing deep into her hot, juicy pussy. Sam felt herself coming to the verge of orgasm from just having the privilege of consuming this beautiful, powerful woman at will. The turn-on was overwhelming, and it drove her to pour her entire heart and soul into every touch. She suddenly switched to long, slow licks of Laura’s clit while continuing to pound her throbbing pussy and ass with the dual-head vibrator. Laura apparently approved of this manuever, because she quickly crossed her legs behind Samantha’s neck and pulled her face and the vibrator as tight as possible against her.

  Samantha continued licking Laura’s clit, then sucked, then licked, then sucked again, until she could feel Laura’s hips starting to reflexively buck. She was fighting it, Sam could tell. “The economic crisis will end. It is just a question of when,” she heard her say. She knew Laura was wrapping up the meeting, so she gave one final push. She thrust the vibrator deeper than ever, sucked Laura’s clit hard, swirled her tongue around the tip and sucked as much of it into her mouth as possible. As Sam’s lips suctioned tightly around Laura’s excited pussy, and her new vibrator moved in and out faster than ever, she felt Laura let go … exploding in Sam’s mouth. The boss’s entire being was overflowing with pleasure as Samantha heard her say, “One moment please …“ to the webcam audience. For at least 15 seconds there was total silence as multiple waves of orgasm flowed through Laura and onto Sam’s face. All the while, Laura looked intently at her BlackBerry while pretending to be reading something either shocking, horrifying or exceedingly bizarre judging by her facial expressions.

  After the final rush of pleasure shot through Laura’s body and her leg-grip on Samantha relaxed, she said, “Okay, just got a strange text from a client. As I was saying …“ With five minutes to spare before the end of the meeting, Samantha took a little time to enjoy herself. She got on her knees, fingered her own wet pussy and used her free hand to massage Laura’s soft, creamy thighs and feel her warm, spent glory box. Within seconds, Samantha had her own intense orgasm. Money wasn’t the only perk of this job. Sam adored women, and loved her work, and as she leaned in to give Laura’s gorgeous pussy one last gentle kiss good-bye, she found herself already looking forward to next Wednesday.

  “A little something new in your bag of tricks, I see,” Laura said at the close of the meeting as Samantha emerged from under the desk and straightened her clothes.

  “I thought of you the moment I saw it at The Pleasure Chest,” Samantha replied.

  “Is that right?” Laura asked, disbelieving.

  “Yeah. I needed an excuse to get at that hot ass you usually keep from me,” Samantha cooed with a sly squeeze of Laura’s left cheek.

  “My ass is your ass, sweetie,” Laura replied as she stuffed a wad of bills into Sam’s pants. “As long as you keep it happy, you can do whatever you want with it.”

  “Your ass’s happiness is my my life’s mission,” Samantha said while transferring the money into her leather bag.

  Laura kissed Sam briefly and added, “I’ve got work. Have a good week, sexy. And don’t stop thinking about my ass.”

  “Never,” Sam replied with a wink, and exited the office.

  3

  Therapist Swanson

  Luckily Samantha’s therapist, Dr. Swanson, was only a couple buildings away from Laura’s penthouse. She dreaded these sessions, which were court-ordered following a D.U.I. arrest two months prior, but the therapist was very appealing to Sam, so they weren’t as miserable as they could be.

  “Hi Sam. How have things been this week?” Dr. Swanson opened with her usual question. Did she realize it was her usual question, or was it just the only opening that ever occurred to her, Samantha wondered.

  “Great. Great, Dr. All’s well,” Sam said with a smile. She didn’t enjoy talking to therapists and having her inner-workings probed by someone who didn’t permit her to probe them in such a way.

  “You said you were great last week. And the week before that,” Dr. Swanson noted. “If everything is always so great, then how did you end up here?”

  Samantha looked at Dr. Swanson and seriously tried to come up with an adequate answer. Even though Swanson bought into the talking-will-cure-everything idea that Sam dismissed as b.s., she had certain reflective, philosophical qualities that appealed to Samantha. Swanson was 17 years older than Sam, but she was one of those women who got better looking with age. She had perfectly formed features and beautiful, sympathetic eyes, but Sam found herself staring at her cleavage and fantasizing about what she was like in bed.

  “Well …“ Swanson was still waiting for an answer to her question. “How did you end up here if everything is great?”

  “It was just a fluke,” Sam finally said.

  “Just a fluke?“ Swanson asked incredulously.

  “Yeah,” Sam continued. “It was late and I was drinking at a client’s house. It was a 6-hour call – I was supposed to be there all night. Two hours in, her husband calls and says he’s on his way home early from some trip, so she has to chase me out. I never, ever drive drunk, but I was loaded and I had drive and I did get caught. Just a fluke.”

  “I see,” Swanson said. “Well, is there anything going on that you would like to talk about? Anything you’re struggling with?”

  “No, not really,” Sam replied. A blank stare and silence ensued, which made Samantha even more uncomfortable than being asked intrusive personal questions. To cut the tension and the boredom, she finally said, “Well yeah, I guess I do have kind of a problem.”

  “Okay … “ Swanson encouraged.

  “Is it a problem if I think of you sexually and have romantic fantasies about being with you?”

  Sam could see Swanson’s pale cheeks suddenly flush with red, and she unconsciously (or consciously, Sam wasn’t sure) touched the side of her left breast.

  “Well, uh … no, no, that’s … uh … that’s a normal experience in therapy. It’s called transference,” Swanson said.

  “Oh, I see,” Samantha replied, even though she already knew and dismissed the term.

  “A lot of people have warm feelings for their therapists and sometimes these feelings can take a romantic turn and … uh … yes, it’s normal to have those feelings,” Swanson
continued.

  Swanson seemed a little unsettled by the disclosure, but Sam was developing a real interest in her and didn’t see a wedding ring, so she persisted.

  “Have you ever been with a woman?” Sam asked.

  “Uh … haha … “ Swanson clearly did not feel comfortable being asked these questions, but she did her best to respond in a professional and helpful manner. “I, you know, uh … I haven’t, actually. But uh … I don’t have anything against it. I just haven’t, uh … “

  “Have you ever thought about it?” Sam asked in an attempt to get Swanson to at least think about it.

  “I … uh … yes, I have on occasion thought about … uh … other women … But uh, these sessions are about you, not me. So let’s get back to you.” Swanson leaned forward in her chair, reached to the glass coffee table that separated her from Sam and picked up a small tin of mints. “Would you like a mint?” she asked.