tagGroup SexFortune Favors the Daring

Fortune Favors the Daring


"C'mon Krista...I dare ya" Jennifer let the words slide out, dripping with mischief.

"OK...no problem." She marched into her brother's room and came back with the porno magazine in hand. They flipped to the back and found the ad in the classifieds. The type was small and Krista had only found it the first time out of sheer boredom.

"Now accepting applications for entertainment services, for exclusive social group. Excellent pay and benefits open schedule. The feint of heart need not apply." That was all, except for a web address discreetly printed just beneath the three lines. "Go on then!" Jennifer urged. Krista sat in front of her computer, typing quickly as Jennifer looked over her shoulder. An application form appeared on the screen in front of them.

"Question 1: Do you consider yourself adventurous or cautious?"

Jennifer answered before Krista could click the button "Is there an option for super adventurous."

"Question 2: Do you enjoy sex?"

The two girls looked at each other and laughed. Krista clicked the yes button as they smiled and giggled. She wondered if she was going to be offered a job as a dancer or a hooker. Either would be fun too try, though she didn't know if she could bring herself to just do it. Too many years of playing the good girl for mom's sake kept her from just launching herself into either line of work. Images of herself in a short skirt, nippleless bra and stilettos, dancing around a pole, wiggling in some faceless guy's lap danced around Krista's head. Or meeting some guy in a hotel room, nameless and leaving nothing behind but his cum and money. The incongruity of the images added to her giggles but caused a slight tinge of arousal which she brushed away as she looked back at the screen.

The remainder of the questionnaire asked about her fantasies, what sexual experiences she has had, attitudes about authority, and so on. 20 questions covered the scope of her personality and sexual preferences. When it was finally done, she brought the mouse over the "submit" button and paused for just a moment. "Jenn, do you really think its safe?"

"Sure.... what could go wrong? Its not like your forced to work there...if they offer you a job just say no."

"You're right...I'm being silly aren't I?" Krista looked back from her friend to the screen and focused on the button one more time. Jennifer reached across and mashed the button on the mouse, sending the information on its way.

"OK...Krista, you sex services worker you, you ready to go hit the stores...see what trouble we can get into there?"

Krista stood and struck a come hither pose, pouting her lips and opening her shirt. "You're just jealous men aren't throwing money at you for your favors."

The next day Krista's e-mail had a message waiting for her. Opening it, she saw that it was a response to her application. "We are pleased to extend to you an invitation for an second interview. If you are still interested in the position, please respond to this message with your address and a time that is convenient for our driver to arrive. Discretion is of the utmost importance and will be extended to you as you extend it to us. Thank you for your time and inquiry."

Her hands trembled slightly as she held her fingers over the keys. The debate in her mind raged at speeds unknown...here was a chance to take a truly amazing adventure, to explore her sexual nature like never before. On the other hand it was a good way to end up kidnapped, missing or murdered. She looked around her room, and took in the totality of her life in her surroundings. She could go on, as is, the façade of the good little girl her parents expected and sneaking around at night. The only time her heart would beat like this was when she played Truth or Dare, and she took the dangerous risky "over the edge" dares. It might be the end of her life, but it would be a life lived fully. She typed in her address and gave tomorrow afternoon for the time. The rest of the day was spent seeing how wonderful the world around her truly was. The mall that was so familiar to her was now somehow different, the colors were brighter, and the aromas were more intense. She couldn't shake the idea that she might not come back from that interview, or might come back forever changed. This was her last time at the mall and she embraced it dearly.

Krista dressed for the interview in a soft dark green skirt and white blouse...she chose her nearly see through bra and sheer black panties to go with it. The skirt hung just above her knees, and the slit showed a glimpse of thigh. She left the blouse open one button extra ...no real cleavage showing, but anyone standing next to her as she sat would get quite the view. She found her high heels to match and then decided to fixate on her hair while she waited. As the clock ticked closer to noon, she finally just left it down naturally. Just as she was about to step outside and see if she could find the car, a knock was at the door.

"Miss Ralley?" The driver in traditional black uniform was a rather tall man, and yet seemed nice enough, smiling at her as she stood. "I'm here to take you for your interview. Are you ready?"

"Please.... What can you tell me about the job?" She walked next to him, until he stepped ahead and reached forward to open the back door.

"Not much really. I don't work for the manor, our company is just hired to drive...we never get out of the car once we're there."

This place was piquing her interest, it was obviously not just a call girl service. She wondered what she had gotten herself into. "So you know nothing about what goes on there? Not even 'driver's intuition' from watching your passengers?"

"To be honest, you're one of the few that talk to me. Most raise the privacy screen and just disappear. The doormen at the manor knock on the roof to let me know the back is empty."

"That's interesting...total anonymity then. Odd." She let her mind wander. Images of what lay before her flooded her imagination. Socialites and power brokers in dark rooms, wild parties with celebrities, or maybe short fat men with too much money who can't get laid otherwise, tying her up and sweating all over her as they tried to stuff their short little dicks into her.

Shaking her head to clear her mind of the myriad of images, she just sat back and closed her eyes. She wanted an adventure, something get her heart beating. Pure and simple...so long as this was exciting, thrilling, risky and daring...this was the place to be.

Soon they were at the manor and Krista said a quick goodbye to the driver, thankful for the company he provided. The large gray columns up front were visible even from the top of the drive. The estate must have been vast, for the main house alone was nearly the size of a castle. Very modern in design, though covered in river rock so that it had an ancient medieval look as well. The combination of Old World looks and ultra modern features impressed Krista that this was not just a social club or even like anything she had known until now. The doormen were large men in tuxedoes, a study of pure intimidation. They led her to the front door as the limo slid away. Krista ventured one quick look over her shoulder to see it disappear around the corner. She hoped that she would see him again, though the reality was that she never would. Dismissing the possibility she turned back to the front door. As she approached the tall white doors, the doormen opened them and stood aside. There in the frame was a beautiful woman in a floor length black gown.

"Krista?" Her voice was husky and low...as if a whisper amplified.

"Yes. I'm Krista."

"Pleasure to meet you, my name is Simone. I'll be conducting your interview. If you would follow me." As the woman turned, Krista saw that the gown was backless, down to her hips and a little past. It flowed in a small swirl as she turned, silk shimmering in the afternoon sun. The soft fabric clung to her form, making her look as if she was part shadow.

Krista followed her down the main foyer and into one of the side rooms. A larger than usual office, decorated to be welcoming and yet maintain a utilitarian feel. One thing that caught Krista's eye was a small statue near the bookcase. It was a naked woman, kneeling before a masked figure in robes. At first glance the woman had the look of Simone ...Krista itched to take a closer look, but Simone had already seated herself behind a large oak desk. Krista took her seat and tried to be professional, though what kind of profession still eluded her.

"Krista, I'm glad you came to interview today. We are always looking for new women to expand our abilities and services here. Your application was impressive and you certainly have the look that we appreciate. Just so you understand, you do realize that you will be servicing our members in all areas of pleasure?"

"So I'll be a whore...." Krista said it bluntly, with neither approval nor condemnation in her voice.

"Certainly not! The cheap girls who blow a man on the street corners for $20 are whores. Whores are dirty and have no respect for themselves. Our women are neither cheap, nor dirty, and respect is of the highest order."

The difference seemed to strike the young woman as more important than she first though as the seriousness in Simone's voice conveyed the worlds that separated the two ideas. She sat in silence for a moment as she pondered the higher, loftier version now before her. Finally she asked "And how do I begin?"

Simone smiled slightly and stood up from behind the desk. "I'm glad to see you're ready. Today will be a day of testing... there will be three tests to pass. If you succeed at all three tests and still wish to join us, then you will begin immediately. Or will be accepted immediately. What you will do for the society will grow as you spend more time here."

The woman opened one of the armoires that were in the office and took out a black silk mask. The eyeholes were small and nearly cat like in appearance. Long strands to the side allowed it to be tied around the head and secured in back. Simone offered it to her.

"You are to wear this mask at all times. If you ever take it off you will be expelled and no longer welcomed here. Do you understand?"

"Yes Ma'am."

"I will lead you down to the grand library. There you are to undress completely. Inside you will see other servers like yourself in black masks, some undressed, some not. The members are in white, red or gold masks. What they symbolize is not important now. If the members approve of you, they will give you a small gold token. When you have ten of them, you may go to the red door at the far end of the library. Do you understand so far?"

"Will I have to serve any of the members in the library?"

"No...the library is strictly for socializing. They may touch you and perhaps fondle, but nothing overtly stimulating. You should do well to be polite and accommodating to them all, and remember white, red or gold masks are members."

"White, red or gold...Yes ma'am"

"Beyond the red door are you three final tests. You will be told what to do for each one. At any time you can leave by exiting through the blue doors on the sides. If you wish to continue, after each test, go to the red door when you are done. Success is always behind the red door."

Krista put the mask across her eyes and positioned the holes so she could see through. Simone stood behind her to tie the strands tightly to prevent an accidental loss. Turning around to face the woman, Krista asked how she looked.

"Fine for now, girl.... But you'll look much better without so many clothes on."

"Could I take them off here? Get your opinion before I go to the library?"

"Yes, that would be very nice girl ...please. Let me see you now and we can go together."

Her hands trembled slightly as she began removing each piece, but as each one came off, Krista thought back to the first time she was had done this, a game of truth or dare when she was fifteen. The moments of revelation and hoping for approval, or at least avoiding mockery or rejection, were making the act of undressing so much harder. Simone was encouraging and comforting at each point along the way, and Krista thought she heard a small breath of appreciation when she lowered her panties to expose her shaved pubic mound. Now completely naked save for the mask, Krista at once felt totally at ease and relaxed with Simone. The older woman looked her over, a smile broadening as she continued inspecting the younger woman's body. "Very nice Krista...quite beautiful... the members should be quite taken with you."

They walked down the hall, Simone leading Krista by her arm, and finally stood before the large doors that led to the library. As the doors opened, Simone stepped away and let Krista enter on her own. The library was a quite large, high vaulted ceiling with chandeliers hanging down. The doors closed behind her quietly and sealed her into the room. Her heart beat wildly, in equal measures of response to the fear, the arousal and the slight embarrassment.

The collection of people was astounding. Men and women mingled easily, the collection of masks was impressive. The majority was black, and she noticed that the servers were indeed in various stages of dress. Tuxedo clad men and women in evening gowns were chatting with others in lingerie, or short robes. Some people in black masks like her own were naked, or clad in leather, a few even in the same tuxedos and dresses as the members in the red, white and gold. No one paid her entrance any more heed than the almost subconscious note of another server's presence. It took a moment for Krista to steel her nerves and begin to make her way around the room, but she soon was walking amongst the congregation, just surveying the place.

Just in her first circuit, she received 5 gold coins, 3 from men in red masks, and 1 from a woman in white and one from a woman in gold. Krista wondered what the significance of the colors was, but assumed she would know when it was necessary. This place seemed to treat information as more precious than diamonds.

As she looked around, she noticed that one of the men in a red mask was holding a glass that was empty. Krista approached him and asked "May I refresh your drink for you sir?" She hoped she was doing this right, all she was told was she was a "server".

"Yes, a Dewars on the rocks" He handed the glass to her without directly looking at her.

Taking the glass and heading for the bar, she quickly got his refill and returned with the glass. "Nicely done girl.... Keep up the good work." He tipped her with two gold coins and then walked away. She looked at her collection, wondering how to hold on to them and still serve with only one hand. The idea struck her and she made her back to the bar.

"Excuse me, could I have a tray with champagne please?" The bartender looked her up and down again, wondering about her, and then filled several flutes with champagne. Krista took it on her free hand and held it at her shoulder. A few passes through the room and she had the last remaining coins she needed to go further. Returning the tray to the bar, she made her way to the large red door and the imposing doormen that stood there.

Standing in front of the door, she wondered if she knew completely what she was getting herself into. She looked around...and saw the other servers in their black masks and the members enjoying themselves. What could it hurt? And Simone did say that at any time she could take a side door and end it all. Stacking the ten gold coins, she passed it to the guard, who did a quick count then stood aside to open the door for her.

The room behind the doors was too dark to see well. When the doors closed behind her, the overhead lights came on and illuminated the room in a dim pink light. There was a large bed in the middle of the room, with what she assumed were a pale blue set of linens, in that they looked slightly purple. Her bare feet padded nearly silently over to the bed and she examined the bed stand next to it. A tube of lubricant, some toys of various sizes and shapes, and a few pair of handcuffs were all that were there. As she was about to look in the bottom drawer, a couple entered the room; both of them dressed in what looked to be very expensive clothes, and both in gold masks. They held hands as they made their way to the bed to sit next to Krista. "You're the new girl aren't you?" The woman's voice was soft and inviting. Whatever fears Krista had soon disappeared as the woman kept talking. "Yes I am...thank you ma'am".

"You'll find it rather wonderful here. The opportunities are endless, and well...exciting is another word for it". She turned and winked at her male partner, the gesture nearly lost beneath the mask. "Have you have been with two partners before girl?"

"No...not at the same time."

"Then hopefully this well be quite the education for you." The woman stood up and began to undress. The dress slid off of her effortlessly. Krista could tell the woman was older than she was, but her body was still well toned and a picture of loveliness. Though she had often wondered about being with another woman, but never had the chance to experience it before... here was the opportunity and with quite an exquisite partner. Then she remembered the man who was also taking his clothes off.

He too was in good shape, no fat on him, but not exceedingly rippled or toned. His cock was a nice size, nothing outstanding or amazing, but not small by any means. He approached Krista's side of the bed while the woman made her way over to the side table and opened the lower drawer. His hand softly touched Krista's knee and he began to rub her leg. The touch was at once tender and yet intimidating. Between the heady thrill of being accepted to this place and the momentary waves of self-consciousness at being constantly naked, Krista's thoughts were blurs. All she could was let the couple have their way with her and let them tell her what to do.

The man continued to slide his hands over her, gentle caresses in an almost exploring, seeking fashion. Krista closed her eyes and relaxed under his touch. He was unhurried, taking his time to cover every inch of flesh. Then as he reached her mid-section and ribs, the woman also reached out and began to mirror his contact on the other side. It was that second pair of hands with softer skin and lighter touches that heightened the experience. That plus the two of them working in tandem was truly enthralling and soon had Krista drawing deep ragged breaths.

"I think the new girl is going to like it here, love." The woman's voice was just at Krista's ear. Her softer hand broke away from the copied movement of the man's and dipped into Krista's lap, a slim finger swiping at her groin. "And she's wet already too. This one is definitely a keeper." There was laughter in the woman's voice as she moved her finger into Krista more deliberately, drenching her finger in evidence of arousal.

"Just lay back and relax...we'll take care of you." The man spoke now, a very refined and well-spoken accent. His voice was soothing, just on the edge of hypnotic. He placed his hands on her shoulders and guided her backwards onto the bed. Krista could feel him move over her as she lay down, his legs on either side of her, the heat from his body warming her where they touched. The woman was once again fingering her, tracing paths from clit to edge of her lips and back in again. The man was focused on Krista's breasts, hands on either side alternating squeezing, caressing and flicking on her nipples.

The woman began to move Krista's legs apart with her hands, leading her to spread them and open herself to the man. Krista drew a deep breath and moved to let him in, tilting her hips to give him a better angle to enter her. He changed his stance and placed his cock at the edge of her opening, steadying himself on his hands. Slowly pushing himself inside, Krista gasped as he made his way inch by inch to fill her. His hips were firmly pressed against hers as he moved to wiggle a bit, flinching against every point of contact that was reachable. He didn't withdraw but leaned forward to whisper into Krista's ear "Now roll over and take the top position girl."

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