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Best Laid Plans (Ch. 5)

Chapter Five

Photo by Maru Lombardo on Unsplash

Jimmy’s career progress was visible from a distance. At first, he was an on-the-field reporter covering soccer games. The more air time he received, the more viewers seemed to like him. None of this was lost on his employer and, very soon, he was seen covering the US Open and football games. It was clear, Jimmy was going places.

Richie could always say he knew Jimmy and it provided consistent interest from colleagues, clients, and acquaintances. But Richie had lost interest in the comings and goings of Jimmy. Jimmy was dead to him. He should have had the same feelings towards Linda. It’s true it hurt that Linda cheated on him. The fact that it happened at Barbara’s wedding smarted even more. In more reflective times, Richie reminded himself that Jimmy saw him and Linda making love. He was behind Linda and she had turned him on wearing that garter belt and stockings. He loved watching her ass cheeks shake every time he rapidly pushed his hard shaft into her. Linda would whimper whenever Richie rubbed his thumb against her backdoor. Nothing was going to stop him from cumming in Linda’s warm, moist grip, not even Jimmy’s sudden entrance in the dorm suite. Richie also realized he had cheated on Barbara with Linda. He could not help himself. He gave into his animal instincts. Linda excited him. She was always open for anything and he loved how she initiated many of their adventures. His most exciting sexual experiences were with Linda. Like the time she wore a French maid outfit and the time he came home to find Linda preparing dinner wearing nothing but a gauzy apron that tied at the waist.

Richie lost track of Barbara. He hoped and he suspected that she and Walt were happy living back home. He thought of Barbara, ultimately, as a home body. He envied her in a way. Although he thought he would be bored doing the same events, year after year, he was a little jealous that most people would be content going to Christmas celebrations in Skaneateles or summers on Lake Keuka. But this was not for him. He did not have that family gathering gene in him.

Instead, Richie concentrated on his classes at law school. He concentrated on becoming a tax lawyer and was recruited by law firms in Boston. It was not the glamorous life one might see on television but it was profitable. He seemed to thrive on the research portion of a lawsuit and his objective was to never have a lawsuit go to court. He managed to settle everything well before a court appearance was necessary. Richie enjoyed the cultural, city life in Boston. Boston was a little city with a big attitude and Richie loved that attitude.

Richie worked at a law firm located at One Beacon Street, the corner of Beacon and Tremont Streets. On one particular Friday night, Richie, once again, was one of the last to leave. He decided to walk down to a pub on Devonshire Street. Crossing the street by King’s Chapel and going down narrow School Street, he saw an attractive woman he thought looked familiar. She did not seem to have the same reaction, but as they got closer, there was no mistaking Linda to Richie or Richie to Linda.

“What are you doing here?” she asked. Richie used his thumb to indicate the vicinity behind him.

“I work over there. What are you doing here?”

“I got transferred to a manufacturing plant in Lynn. I live in Swampscott.”

Richie was vaguely familiar with the location. “Is Jimmy still in New York or are you two together?”

“I left Jimmy a while back. He cheated on me… again. This time with someone from the network. Look, Richie, I’m sorry about what happened. I was drunk. I know that’s no excuse. Can you put that behind?”

Richie took a deep breath. “Would you like to get a drink across the street?” Richie motioned to the Parker House, the hotel where John Kennedy announced that he was running for President of the United States.

“Richie, I’m supposed to go to a women in manufacturing cocktail party, but I would much rather go with you anywhere.”

The Parker House was a far cry from where they went for their prom several years ago. The Parker House was an old school, old money establishment, elegant in its furnishings and rich in its comfort. They checked their coats and made their way to Parker’s Bar. There they settled in and ordered drinks.

Richie sipped a vodka martini and Linda had a cosmopolitan.

“How did you know Jimmy was cheating on you?” Richie asked.

“Always the devil’s advocate, Richie? He was here. In Foxborough for a game. I was supposed to meet him and he was going to show me some behind-the-scenes stuff. I went back there and someone directed me to a trailer. I open the door and there he is with some blonde riding his cock. In a production trailer!” Richie looked around to see if anyone reacted to Linda’s use of the word “cock.” Apparently, no one heard her or no one cared.

Richie conceded the point silently. He took a sip of his drink and set the drink down again. “Do you remember the time Jimmy walked in on us?”

Linda smoothed her skirt. “Yeah, I remember. But that was different. We were already going out for a while. As I recall, that wasn’t even the first time you gave it to me from behind.”

“I know. I wasn’t trying to make a point,” Richie responded slowly. “I was just thinking how much I enjoyed that.”

Linda ran her finger along the edge of her glass. She looked at Richie and crossed her leg. Richie could see she was not wearing black pantyhose. She was wearing black stockings. Images of he and Linda wildly making love in various positions, various locations, various attire passed through his mind. But he also thought about seeing Linda taking Jimmy’s cock in and out of her mouth. He was determined not to ask her out.

“Richie, I’d like another chance with you… with us. Would you like to go out? Think about it.” Linda got up and went to the restroom. As Richie leaned back in his chair, he noticed he was getting hard. There was no denying Linda was a sexy, attractive woman. But she was trouble. Richie had firsthand experience. But he also knew he’d be in the ride of his life. As he sipped his drink, Linda returned and dropped her panties in his lap. Richie picked up the undergarment. Linda sat down. Instead of hiding it, Richie spread it open so everyone could see. He then brought it to his face and took in Linda’s fragrance. Linda’s eyes opened a little wider. Richie stuffed the panties into his pocket and motioned for the check.

Outside the Parker House, Richie asked the doorman for a cab. The doorman whistled a cab for them and they got in.

“Where to?”

Richie leaned toward the driver and handed him a hundred dollar bill. “Just drive.”

“Where are we going?” Linda asked.

Richie reached up Linda’s skirt. She let out a little yelp as she felt his hand on her thighs and on her pussy. “I’m where I want to go,” he said. Looking at each other, Richie could feel that Linda was spreading her legs for him. He leaned toward her and they kissed each other madly. The driver adjusted his rear view mirror to watch. Linda made eye contact with the driver as Richie lowered his head and rubbed his face against her bosom. Linda took Richie’s head in her hands and pressed his face against her breasts. The driver headed towards the Mass Pike thinking there’d be less traffic and less prying eyes. Richie lifted Linda’s skirt. The driver and Richie could see Linda’s neatly trimmed, barely there bush. Richie pulled Linda’s legs towards him and he got on his knees to lick her pussy. Her head rolled back. She could see bridges and buildings go by. Richie licked her slit up and down, then concentrated on her clit rolling it around and around using just the tip of his tongue. He varied his speed and it was beginning to drive Linda crazy. Her breathing was becoming more like gasps and her body stiffened as he lapped up her fluids. Richie lifted his head and Linda cried out when he stopped. She wanted more. More of anything and everything. Richie wiped his face, sat back and unzipped his trousers. Linda sat up and helped Richie free his cock. The driver could see Linda immediately take the cock in her mouth and suck. Richie brushed her hair back so he could watch her work her red lips up and down, then take it completely out of her mouth and swirl the head with her tongue. Richie was already as hard as a rock. Linda loved how his stiff muscle filled her mouth with warmth. She felt power over him and she liked that. Richie started to raise his ass off the seat to fuck her mouth but Linda had other ideas. She moved Richie to the center of the seat and straddled him, guiding his cock into her. When they made contact, Linda cried out as she lowered herself onto him and feeling his thick cock fill her pussy. She kept it in there, grinding her hips against his, feeling him fill every bit of space in her. Richie reached around and grabbed her ass in his hands, bringing himself into her even more. Then he tried lifting her hips. Linda wanted the same. She began to move up and down on his cock, letting her lips grip him as she went up and then spread apart as his muscle entered her. The scent of her sex filled the cab and was driving the driver crazy. Up and down she went, fucking Richie for anyone to see as they rode on the Mass Pike. Linda pushed her hips into Richie harder and she pressed her hand against the ceiling as her orgasm shook her, cum-bathed Richie’s cock and her body collapsed onto him.

When Linda calmed down, Richie urged her to sit next to him. Although he had not cum yet, Richie Put his cock back into his pants and gave the driver an address in the South End. When they arrived, Richie held her by the shoulders and guided her to his place. She looked around in a daze, not really knowing where she was. Inside his place, Richie took her coat. Then he unbuttoned and unzipped her until she stood in his living room in high heels, garter belt and stockings. Then he slowly stripped off his clothes, all the while staring lasciviously at Linda. She thought they would go to his bedroom. Instead, Richie pushed her down to knees. He grabbed the back of her head and brought his cock to her mouth. She took it in greedily. He enjoyed the sight of her in front of him. He especially liked it when she removed his cock and rubbed it on her beautiful face. It was intoxicating watching her. He stepped back. Linda wiped her face with her hand and licked the fluids. Richie went to an end table and brought out a small vial. He turned Linda around on her hands and knees. He squirted a lubricant all over her behind and worked it into her asshole. He rubbed more lube on his cock and moved behind her. He gently but persistently pushed his cock against her backdoor until her sphincter opened up, the head pushed past her gateway and his cock got sucked into her butt. Linda screamed and looked behind her. “Don’t stop,” she sobbed. He slowly pressed into her until his balls rested against her. Just as Linda was getting used to being filled up back there, Richie slowly pulled back. The sensation was bizarre to Linda but she liked it. Linda lowered her head and let Richie shove his cock into her ass and withdraw again and again. Her moans were incessant and loud as he fucked her behind. He couldn’t take it any more and shoved his cock into her again as deep as he could go and began squirting his hot cum into her ass. They both screamed as he spasmed inside her.

They spent the rest of the weekend pleasing each other as wildly as they could think.

Chapter Six will be published Thursday, December 20, 2018.

Photo by Alex Iby on Unsplash

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