Randy must pleasure the towns women

Chapter 9

It was 6:55 PM and Randy had been parked across from the mayor's house for over an hour, just staring at the house. He couldn't stop the butterflies as he reflected on his unimaginable circumstance. It wasn't the sex that bothered him. That was the easy part. Even if he wasn't really attracted to the women, he was sure he'd be able to satisfy his...customers.

"Are these women customers?" he thought. The word stuck in his throat and made him feel dirty. Is Ms. Figgis doing this for money? The thought made him feel sick. It wasn't long ago that Randy had fantasized about melting the icy Ms. Figgis, making her feel desired and giving her a gift of passion. That was all gone now. Ms. Figgis wasn't a lonely, repressed, good-hearted woman in need of a man's attention; she was a bitter, sadistic, shrew who used men as she used a toilet.

Randy assumed that the women he was about to see were paying Ms. Figgis. A brief smile crossed his face as he thought, "Hey, maybe I'll make a few bucks out of this." The smile didn't last long as his optimism was quickly replaced with feelings of betrayal. It hurt to be treated so badly by a woman he once respected.

The alarm sounded on Randy's watch. It was time, and something told him that he shouldn't be late. As he approached the front door, Randy remembered his only meeting with the mayor's wife. It was at one of the plays that the high school had produced and she wasn't exactly the warmest person in the world.

Mrs. Thompson was not the most attractive woman in town. She was in her mid 50s but that's not what made her unattractive. It was her expressions. She always seemed to be in various states of anger or disappointment which made her face look harsh and weathered.

The walk to the front door was much shorter than Randy hoped. As he extended his arm to knock, the door jerked open. "Get in; quickly", she demanded. Mrs. Thompson quickly closed the door and led him upstairs to the bedroom. So much for the small talk, Randy thought.

The bedroom was huge, highlighted by the biggest bed he'd ever seen. "Hurry up, my husband will be home at 8", Mrs. Thompson barked as she removed her jewelry. Randy took a moment to check out Mrs. Thompson's body. She was wearing a beige silk robe that showed off a nice ass and what seemed to be some fairly large breasts. Her curvy figure was unexpected, since she usually dressed in unflattering, business type attire.

Mrs. Thompson sat on the bed as Randy undressed. He stepped out of his shorts and stood in front of Mrs. Thompson, showing off his muscular body. "Hmm, I see why you got the job. Ms. Figgis always did have an eye for talent." The word "job" rang in Randy's ears and the feeling of betrayal returned.

Randy tried to put it out of his mind and began rubbing his cock. As it became hard, Mrs. Thompson opened her robe giving a glimpse of her soft breasts. They were larger than he imagined but not the inflated monstrosities that some of his trophy girlfriends carried.

Now things were picking up and Randy pointed his cock at her mouth. Mrs. Thompson pulled back and said, "Do I look like some sorority girl on spring break? You're here for my pleasure, not yours. Now get busy."

Mrs. Thompson laid back and pulled Randy's head between her thighs. He got the not so subtle hint and began gently licking the outer fold of her pussy. "Mmmm, that's nice," she purred. Randy lightly traced his finger around the lips while he licked. Her hips began to move, inching closer to his face.

His tongue darted quickly inside her pussy, now trying to penetrate her with his tongue. Mrs. Thompson seemed to approve as she began to moan. Next she felt his finger slowly entering her; twisting, then withdrawing. His tongue moved up to her clit as his finger kept its pace, slowly entering, twisting and withdrawing

Randy quickened his pace, both the licking and the fingering, now adding a second finger to her dripping wet pussy. Two fingers thrusting and twisting inside her hot pussy. Mrs. Thompson ran her hands through his hair as she closed her eyes and enjoyed the intense feeling of having her pussy eaten. Randy's free hand moved up her body and squeezed her full breast. Softly playing with it and rolling it around her chest.

Mrs. Thompson was riding the edge of an enormous orgasm. The powerful strokes of Randy's fingers inside her hot pussy were so intense. The pressure built inside her with each stroke, now three fingers in constant motion, thrust, twist, withdraw. Every time the same, like a machine, sliding in his long fingers, twisting at the wrist and withdrawing.

"Fuck", she gasped, trying to hold back her orgasm, not wanting the feeling to end. Randy felt her pussy clinching his fingers, trying not to release. Her hips moving in time with his strokes, his hot breath on her clit, thrust, twist, withdraw; thrust, twist, withdraw; thrust, twist, withdraw.

"Cum for me!" Randy said as he looked straight up into her eyes.

"Fuck" The only word Mrs. Thompson could manage, her body writhing with pleasure.

Thrust, twist, withdraw; thrust, twist, withdraw; thrust, twist, withdraw, her body tensed, the pressure inside nearly unbearable. She let loose a scream as her pussy spasmed out of control, drenching Randy's face with her juices. Her hips bucked wildly and his tongues followed, lapping the sweetness and causing further shudders.

Mrs. Thompson's chest was heaving, having expelled all her air while she came so hard. Her body was trembling and spent. She took a deep breath as she began to regain her senses, the trembling now more like a low vibration coursing through her veins.

"Get dressed," She said while pulling on her robe.

"Don't you want me to..."

"Oh, that's right, it's not sex unless the man cums." She snapped. "Didn't anybody tell you silly boy? Whores don't cum."

Randy dressed quickly as Mrs. Thompson curled up in her bed. "I think you can show yourself out."

Chapter 10

The next few months passed in much the same manner. Ms. Figgis would send him out to various women and he would do whatever they wanted. It seemed the only rule was that the visit could not exceed one hour. Ms, Figgis set that rule and none of the women dared break it. Many men dream of this type of situation, being used for sex, but for Randy it was becoming a nightmare.

Some of the women were demanding like Mrs. Thompson and part of their fantasy was degrading a man. Those were tough days, but there were also some "appointments," as Randy came to call them, that were almost sweet and romantic. He met all sorts.

Mrs. Tolbert liked being fucked by two men, Randy and her husband, while her husband called her a dirty cocksucking slut.

Mrs. Camp liked being fucked up the ass while her husband jerked off in the closet.

Mrs. Collins loved to suck cock, but her husband thought it was beneath a woman of her standing. He came from a powerful family and they married just after she graduated from college, leaving a campus-full of spent cocks in her wake. Mrs. Collins couldn't risk her marriage by picking up guys in bars, so Ms. Figgis' service was the answer to her prayers.

Mrs. Johnson was a widow and she missed her husband. She didn't want sex, she wanted a companion and Randy was happy to help. They usually just talked or played gin; sometimes she would ask him to dance. Of course, she had to teach him first, but she had to do the same with her husband so it made her smile even when Randy would step on her toes just a bit.

Randy met all kinds and his schedule actually became routine. Here's a typical day.

Morning – teach class

Lunch – get cock sucked by Mrs. Collins in school parking lot; be sure to cum in her mouth or she gets mad. If she wears red dress call her a nasty whore. If she wears blue dress, finger her ass and pussy while she sucks. If she wears yellow dress, pretend to be her son.

Afternoon – teach class, eat Ms. Figgis' pussy during free period.

Night – appointment with Ms. Spears, the school librarian.

Ms. Spears was a surprising appointment. She was your stereotypical librarian, late 30s, small, frail, coke-bottle glasses, and her hair pulled back in a bun. He never figured her to be the type who would use Ms Figgis' special service. Randy figured this would be an easy appointment, she'd probably just want to see a movie or read poetry to him.

He arrived exactly on time, just as usual, and Ms. Spears greeted him with a smile. As they moved to the living room, Randy admired her house. It was just how he imagined it, very conservative, with the feel of an English country home.

"Please have a seat Mr. Tucker."

"Please, call me Randy"

Ms. Spears chuckled, "Yes, I suppose first names are in order under the circumstances."

The conversation was very natural, they talked about work and relationships. Randy really liked Ms. Spears and he wondered why she didn't have a man in her life. She was smart, funny, and extremely kind. Her charity work was legendary. Ms. Spears wasn't a supermodel but she was no dog either, in fact, as the time passed and Ms. Spears began to relax, Randy started to see her in a different light. "I have to ask, why don't you have a husband? You're a great catch."

Ms, Spears blushed, "I just haven't found the right man who shares my same interests."

The hour was nearly up and it had gone just how Randy expected, even the tour of her personal library of rare books.

"I guess we should go upstairs now." She whispered.

As they reached the bedroom door, Ms. Spears handed him a blindfold and told him to put it on. She took Randy's hand and led him to the bed. "Wait here a moment, I have a surprise for you."

It was kind of cute, she was probably just too shy to get undressed in front of him, he thought. Finally, Randy heard her return to the room. "Take off the blindfold."

"I can't wait for my surprise."

Randy's jaw dropped. He looked but he couldn't believe his eyes. The sweet mouse of a woman was gone, replaced by a menacing dominatrix in thigh high boots and carrying a whip.

"Get on your fucking knees!" She commanded.

Frozen in disbelief, Randy hesitated and Ms. Spears slapped him across the face, hard.

"I said, get on your knees and don't you look at me, look at the floor!"

"Yes ma'am" Randy relied.

"Mistress, call me mistress, whore."

"Yes mistress."

She ordered him to strip naked and Randy complied. Soon his ass was bright red from the whip she carried. He dared to look up for a second and saw something he wished he hadn't. She was wearing a strapon and was in the process of lubing it up.

"That's right, you're gonna get fucked."

"Please, no, the hour is up, the hour is up!" Randy shouted.

Ms. Spears looked at the clock and knew he was right. Disappointed, she left the room. Randy dressed and made his way downstairs. As he reached for the front door, he heard her calling from the other room.

Looking him in the eyes, she said, "I never would have hurt you."

"I'm glad to hear that." He said in a sarcastic tone.

"I was hoping you'd be into it."

"Well I'm not."

"I guess you see now why I don't have a husband." She said as she looked at the floor.

It was unbelievable, this woman was about to violate him in a way that would probably scar him for life but now he actually felt sorry for her. Not sorry enough to do what she wanted, but sorry nonetheless.

"You don't have to come back again, Randy. It spoiled it for me when I saw that horrified look on your face."

"I thought that was what it was all about."

"It's not about being a sadist and hurting people for the sake of hurting them. It's about trust and love. I guess it's hard to explain."

"Well I'm sure one day you'll find a man who loves you enough to take it in the ass."

Ms. Spears laughed and kissed him on the cheek.

Chapter 11

Lisa was the lone bright spot in what had become dark days for Randy. She had been hired on as a full time teacher at the start of the school year. Apparently Ms. Figgis must have liked her or she wouldn't have been hired, or maybe she just saw Lisa as another pawn to control.

They usually ate lunch together. Mrs. Collins hadn't scheduled an appointment in weeks. She probably got a new pool boy. Whatever the reason, Randy was happy to spend time with Lisa. She was his only real friend.

"Are we still on for tonight? " Lisa asked

"Sure, I have to prove to you that I can cook."

"I'll be the judge of that."

It was nice to finally have a night off to relax. Some of the women had started to complain about Randy's energy, or lack thereof. Ms. Figgis decided that he did need a day off so there were no more appointments on Wednesdays. This had become movie night for Randy and Lisa. It was the only thing that kept Randy sane.

Tonight was Randy's turn to host, which meant he was cooking and Lisa would pick the movie. Most guys would rather die than let a woman pick the movie, but Randy didn't care. It was just nice to have a relaxing evening at home no matter what chick flick he had to watch.

"So, how was it?" Randy asked

"I'm shocked, it was actually good. You can really cook."

"Thanks, you see I'm more than just a pretty face" Randy joked.

"I've always known you were more than that." Lisa said softly as she looked into Randy's eyes.

They way she looked at him made him uncomfortable so he quickly changed the subject.

"What movie did you get?"

"Little Women."

OK, so Randy cared a little about what movie she brought.

"Oh, that sounds great." Randy said through a fake smile.

"I'm just messing with you. I got Gladiator. I hate chick flicks too."

"You rock."

They popped in the movie and brought the wine into the living room. This was great, a good meal, alcohol, and high quality violence on TV. It doesn't get much better.

The wine flowed and Randy just sank into the couch while Lisa cuddled next to him. He was exhausted and drifted off to sleep. When he woke an hour later, Lisa was snuggled close and her hand was resting on his penis.

Randy shifted in his seat

"Shhhh, it's ok." Lisa whispered as she lightly rubbed his hardening shaft and began to pull down the zipper.

"Wait, don't." Randy said as he rubbed his eyes.

"It's OK, I know the kind of girls you like Randy."

It somehow seemed wrong, like he was taking advantage of her. Lisa dropped to the floor in front of him, her chubby little hand was now holding his bare penis. She began stroking it and he couldn't help but get hard as a rock. He just relaxed for a moment and enjoyed the slow strokes. Then he looked at her and it seemed wrong again.

"Lisa, don't"

"I want to." She said as she lowered her head towards his cock.

"Stop." Randy said as he started to push her away.

"I can do it. I can be like those other girls for you." She said as she began to cry.

Randy pushed her away and zipped up his pants. Lisa slumped to the floor and sobbed.

"Lisa, I don't want you to be like those other girls. You're better than them."

"You don't have to be nice. I'm no beauty queen, I'm too fat. You can say it."

"I don't think you're fat. I think you're perfect."

"Yeah, right." She said as she started to make her way toward the door.

Randy ran after her and stopped her in the hallway. He grabbed her and gave her a hug and Lisa sobbed into his chest. There was something different now. Randy wanted to kiss her. He thought about it and he knew it wasn't pity. He also knew it wasn't about sex. She really was beautiful and seeing her sad was breaking his heart.

Lisa looked up and this time there was no kiss on the forehead. Their lips met and it was different than anything he ever felt before. They kissed again, slowly, deeply. Randy reached down and picked her up, carrying her to the bedroom.

He laid Lisa down on his bed and undressed, now wearing only a pair of boxers. Lisa looked over his body, and smiled. "Are you sure about this?" She asked. "I've never been more sure." Randy replied with a smile.

Lisa began to undress but she was hesitant. She was very self-conscious about her body, knowing that her chubby frame was far from the barbie dolls Randy usually dated. Randy sensed it and kissed her then removed her bulky sweater. Lisa crossed her arms in front of her breasts trying to cover herself.

Randy put his hand on her belly then gave it a kiss. She wasn't skinny but she certainly wasn't fat either. Over the last few months, Randy had been with many full figured women and he actually started to prefer them. He liked feeling their soft curves instead of the tight muscles of the skinny women he used to date.

Slowly, Lisa started to relax. She could tell that Randy liked what he saw and she let him undress her fully. He finally had a view of her large DD breasts that she kept hidden under layers of clothes and he began to lick and suck on her hard nipples.

Randy climbed on top of her and aimed his dick at the entrance of her pussy. He looked into her eyes and gave her a kiss.

"It's my first time." Lisa said.

"You've never done this before?" Randy asked.

"My mother always warned me about guys just looking for sex. I was waiting for the right one."

"Are you sure about this?"

"I've never been more sure." Lisa smiled.

Randy kissed her one more time then placed the head of his penis at the edge of her pussy. He slowly pushed forward as Lisa gasped, her walls tightly grasping his shaft. "Shhh, just relax." Randy said into her ear. He just stayed inside her without moving, waiting for her to get used to him.

Lisa relaxed and her hands began pushing against his ass. Randy moved slowly, letting her control the pace with her hands on his ass. She started to move faster and so did randy, now they were finding a pace.

Lisa was moaning, it was starting to feel better and better. She pulled him close and kissed him deeply while he increased the pace. Her body started to tense and she came. The grip on Randy's cock was incredible and he knew he wouldn't last much longer.

"I'm close." Randy grunted.

He started to pull out but Lisa grabbed his ass and pulled him deep inside her while looking into his eyes. Randy erupted deep inside Lisa's warm wet pussy.

Randy just held Lisa and stroked her hair until she fell asleep, but there wouldn't be much sleep for him that night. He wanted out of Ms. Figgis' web for a long time but now it was different. He couldn't stand for Lisa to find out about it.

He had to get the tape back. The tape of him having sex with Shay was Ms. Figgis' power over him. He had to get that tape if he wanted to be with Lisa.

To be concluded shortly...
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