The Tale of Peter & Alicia

"Peter, come on Peter. I just don't have time for another fund-raiser. I have work to do this week."

"Alicia, this one is important. He can contribute big bucks to my campaign and, besides, I think you'll really like him. He's not one of those stuffy old money millionaires."

"OK, when and where?" she said, resigned to the duties of a candidate's wife.

"Thursday night, cocktails at six, dinner afterwards. Dress to impress."

"Yeah, gotta go. I have a meeting in 10 and people are already waiting."

Peter hung up and smiled. The host was a business acquaintance, a guy named Jack who owned several businesses, some legitimate and some on the shady side. He was a dog and his wife, Alicia, was his type; tall, regal, svelte. Her presence would bring him sniffing around and almost assure a very large check at the end of the fund-raiser.

Peter had met Jack through one of his businesses, a very high class and very private club. Members only, expensive with a non-stop party on the main floor of a very elegant old country estate plus a variety of very discrete play rooms upstairs. Couples were admitted with a handshake, women by themselves were given $1250 table stakes for the roulette table, single men paid $1250 for the evening.

The house rules for members were never written but fully understood. The main floor was elegance, rooms that would befit some of the finer places in Monte Carlo. Upstairs was another story. Whatever your personal kink was, you could satisfy it somewhere. Sex in private with your mate or someone you just met? Gang bangs? BDSM? Exhibitionism? It was all there. A lounge with a flat screen TV allowed 'spectators' to watch all the action. Private lounges gave a couple or a threesome or foursome viewing privileges, too, by invitation only.

Peter was a member who attended regularly, two or three times a month, paying $1250 per visit. It was an expense that he was finding harder and harder to disguise. Asking his wife to join was out of the question and sure to begin a career killing divorce.

He picked up the phone and called Jack. "We'll be there," he said, "but the upstairs will be closed?'

"A few members will be in attendance but there will be nothing going on that wouldn't be proper at church," he assured him. "Most of the people will be the heavy hitters, big donors. Alicia will be with you?"

"Yes." Peter hung up.

Jack walked over to his penthouse window and watched the evening traffic build on Lake Shore Drive. A sly smile crossed his face as he imagined Alicia on his office couch with her legs spread wide and her panties hanging on an ankle. In his imagination, she was wearing a short, basic black dress rucked up to her waist and black spike heels. She was chewing on her pearl necklace as she watched him undress, waiting anxiously for him to fuck her.

He found her mouth irresistibly erotic and he stood there for a moment, trying to decide to give her another pearl necklace or just avail himself of the sweetest looking pussy he had ever seen. "Throating" her would be almost as pleasurable as....

A knock at the door interrupted his fantasy.

"Come," he said, smiling at the several meanings of the word.

His secretary entered. Christa was an older woman in her late thirties, she had spent almost 20 years doing very expensive outcalls for one of his businesses. She was very meticulous and knew all his businesses well. In fact, she would still occasionally do a weekend as a favor to some of her most trusted clients, those that preferred a tryst with a more 'mature' woman.

"Here's the catering order for your party."

"Thanks,' He scanned it quickly, making sure everything was top of the line.

He circled the bar order. "Make sure the caterer understands that the liquor is top shelf only. I'll be pissed if I see anything that retails for less than $80 a bottle."

"Yes, sir. Do I get to keep everything that's not empty?"

She turned and walked out of his office, making sure that he got a long, lingering look at her ass. It was an ass that was as good as they get, a backside still perfectly shaped, that had earned her hundreds of thousands of dollars since he had seduced her shortly after she turned 18 and, within weeks, turned her into one of Chicago's highest priced whores.

Jack was now 50, still trim and fit with that greying-at-the-temple hair that made him look like a distinguished business man or a model for very expensive clothing. Smooth and polished, he was proud of the fact that he had personally broken in every one of his female employees, a few straight out of high school but most were co-eds from Northwestern or UI-C.

Christa's Story

In most cases, the seduction was easy. He would find them working in places like the cosmetic counters at large department stores or hanging out in coffee shops near a college campus. After some small talk gauged to learn their interests and gain their trust, he would invite them to a social event, leaving his card, "Jack Dunby, Chief Executive Officer, Dunby Enterprises, LLC."

It was only on the second or third meeting that he made his move, usually in his office or his penthouse. Christa was one of his first 'recruits.' Not quite a year out of high school, she was working as a cosmetics technician at Saks, trying to decide if she wanted to go to college. He had invited her to a small party and watched as she seemed to mix in well with his guests. She was amazingly mature and composed for an 18-year old, he thought. At the end of the evening, he noticed that she had too much to drink and sent her home in a cab.

A week later, he met her for coffee, 'just to make sure she was OK.' During the conversation he mentioned that one of his businesses was an escort service, something that seemed to alarm and excite her at the same time.

"I don't see how a woman could sell herself like that," she said.

"That's not part of the deal. The ladies I employ are there for an evening of companionship and good conversation only, mostly with out-of-town executives who have to attend business events."

She looked at him with a hint of disbelief and a slight smile.

With just a hint of condescension, he said, "Of course, they're both adults and if they decide to take it to the next level, that's a decision made between the two of them. She earns $1000 for the evening or $3000 if he wants her to be available for the weekend."

She swallowed hard. "Still, I couldn't imagine . . .'

A few weeks later, he invited her to another party, 'Very formal,' he said.

"I don't have anything to wear."

"Drop by Macy's downtown. Ask for Sheila, my personal shopper. She'll help you find something."

"I can't afford..."

He interrupted her. "Nonsense, there will be no bill." He hung up.

Sheila called the next day. "Your new friend Christa has a new cocktail dress. Isn't she a little young for you?"

"I'm just introducing her to polite society."

"Ummm, OK. I'm having a few alterations done. She's a little too busty for off the rack. It's a red halter top with a short, flared skirt. I'm having the waist line taken in a few inches."

"Bill me."

A few days later, he sent a limo to pick Christa up. When she arrived at the hotel ballroom, she looked spectacular. She knew how to apply makeup perfectly, the dress accentuated her assets; just the right amount of cleavage, the silk of the skirt molded her ass nicely. She was immediately plied with drink. Jack moved in late in the evening when he noticed that she was pleasantly tipsy and thoroughly enjoying herself.

"Fun, I'm having fun," she said.

"You're the highlight of the evening. I think you've made a lot of friends." He slipped his arm around her shoulder and she leaned into him.

"Tonight," he thought, "I'll take her panties down and bust a cherry, if she's still a virgin."

For the rest of the evening, he focused on Christa, complimenting, touching, dancing with her, doing everything that a naïve young woman would interpret as the perfect evening with a perfect gentleman. At 1:00, she helped him see his guests off.

"My car is out front, I'll see you home."

Driving down Michigan avenue, Jack said, "My Condo is on Lakeshore, right over there. I hope it's OK but I need to stop and pick up some papers."

"No problem."

As the driver pulled into the underground garage, Jack asked, "It's the top floor, would you like to come up and see it? The view of the lake is spectacular."

She nodded and they rode the elevator to his place. He showed her around; the living room, kitchen, dining room, guest bedroom, master bedroom.

He fixed a drink and handed it to her. "Take this and go out on the balcony. I'll grab those papers and join you in a minute."

He waited until she had finished most of her drink. She was standing near the railing, leaning on it to steady herself. He stood close behind her.

"It's cold," she said.

He snuggled closer and put his arms around her waist, covering her partially with his dinner jacket.

"I think I'm a little drunk."

"Yes, you are." He kissed her on the shoulder.

She shivered, but not from the cold.

He pulled her tighter, enjoying the view as he watched her breasts rise and fall. He could see her heart beat and he listened to her breathing. It was mostly nervous gasps. He kissed her neck and nibbled on her ear. She stood very still, a sense of apprehension caused her to tremble. His hand moved upwards, stopping only when they reached the bottom of her breasts.

"Are you going...are you going to...?" it was more of a gasp than a question.

As if to answer her unfinished question, he pulled at the bow that held her halter top in place. She caught it as it fell, holding it over her breasts. He covered her hands with his and moved them down to her side, finding only token, meek resistance. She was naked from the waist up. He covered her with is hands, feeling her nipples dig pleasantly into his palms. A soft moan escaped from her lips and her knees started to buckle.

He turned her around to face him. He kissed her, a long and passionate tangling of tongues. He pushed the dress over her hips, letting it fall to the ground. She was wearing only the briefest of bikini panties. She was frightened at what was happening but unwilling to stop it.

Only one other male had played with her breasts and she had learned then that they were her hot button. No one had exposed her so completely.

Jack was surprised that she was such an easy mark. He knelt and covered a nipple with his mouth, using his tongue to tease it into a rock hard point. He kissed his way to the other nipple.

She pulled his head tighter and felt moisture start to run down the inside of her thigh. His hands had moved under her panties, stroking her ass cheeks. She had become so sexually excited she could no longer stand. He picked her up and carried her into the master bedroom, laying her carefully on his bed.

He stepped back to admire her incredible body as he stripped. She whispered "I'm, I'm a....as she watched him.

"A what?'

"A virgin. I've never made love before."

"I'll be gentle," he soothed as he laid down beside her. He made a mental note to explain the difference between making love and fucking. This was fucking. She needed to know the difference.

As he leaned forward to kiss her, she raised up to meet his lips. His hand caressed her belly, slowly sliding under her panties, searching for her slit. He found her clit, causing her to cry out as she instinctively thrust her hips upwards. He used two fingers to penetrate her and began bringing her to her first orgasm.

"No one has ever done this to you?"

She shook her head and bit her lip. "No," she whispered.

He sped up, finger banging her to her first real orgasm. She thrashed, moaned and clutched his hand, forcing his fingers deeper into her.

After she came, she collapsed, breathing heavily, her legs spread wide. "I'm going to do something special for you," he whispered as he lowered her panties and dropped them on the floor.

He knelt between her legs, ran his arms under her knees and pushed her legs wide and up so he could fondle her breasts. He kissed her belly and slowly worked his way down. He licked around the sides of her pussy, now open and running heavily with her fluids. He heard her gasp and listened to a sharp intake of breath as he caught her clit between his lips. Slowly she began moving her ass, trying to fuck his tongue. As her hips began moving more rapidly, straining for another orgasm, he would back off, prolonging the pleasure.

He brought her close three times before heeding her pleas for release.

"No, don't stop! Keep doing that.....ahhhh!"

It was a massive orgasm, one that left her shaking and moaning, gasping for breath. Her hips rose and fell, her pussy spasmed around his tongue.

"Oh, my God!" she whispered to herself.

He knelt on the bed with her legs still wrapped around him. "I'll have to teach you how to return the favor," he answered as he rubbed his cock up and down her wet and wide opening.

Whenever it brushed across her clit, her ass would twitch, an involuntary reaction to a well stimulated vaginal region.

He pushed forward, just inserting the head of his cock. Leaning forward, he supported himself by placing his hands on either side of her head. Knowing what was about to happen, she opened her eyes and looked up at him. She realized that although she had protected her virginity for such a long time, she was about to give it up on what was little more than a one-night stand. It was whorish beyond belief and it excited her. She wrapped her legs around his waist and tried to increase his penetration.

He backed off, keeping just the head between her soft folds. "Tell me," he whispered.

She looked up at him again, not understanding what he meant.

"Tell me you want me to fuck you," he whispered.

"Make love to me," she said.

"Tell me you want me to fuck you," he repeated softly.

"Fuck me."

He smiled as he slowly inched forward. He liked to savor his new sexual conquests. Less than half way in, he realized she really was a virgin. Backing up just a bit, he suddenly shoved his cock balls deep, ripping her hymen and causing her to cry out. He immediately began pistoning in and out. She pulled him tightly to her, smashing her breasts against his chest and began matching him thrust for thrust. It only took a few more seconds for her to come a third time in less than twenty minutes. He exploding almost immediately as her pussy muscles milked him dry. When she felt his cock start to pulse, she thrust herself upwards, talking as much of his cock as deeply as possible and screamed in ecstasy.

Exhausted, she fell asleep only to awaken the next morning to an empty bed. The stains created by her surrender were a dark spot at the center of the bed. A small envelope was resting on the pillow next to her. It contained ten 100 dollar bills and a note.

'See, being an escort can be a worthwhile experience.'

At first, the message was like a stab into her soul. After a few moments, though, she slid her hand between her legs and began gently masturbating herself as she thought about last night. She smiled to herself and her new career began the next day.

NEXT: Peter and Alicia shake hands with Jack