Cougar Confessions #1: Alicia Read online

  Cougar Confessions: Alicia

  By Jessica Ryan

  Copyright © 2014 Jessica Ryan

  All Rights Reserved.

  Published by Jessica Ryan Books

  PLEASE NOTE: This book is for sale to ADULT AUDIENCES ONLY. It contains sexually explicit scenes, graphic language and may be considered offensive by some readers. Please store your files where they cannot be accessed by minors.

  This is a work of fiction. Names, characters, places and incidents either are products of the author’s imagination or are used fictitiously. Any resemblance to actual events or locales or persons, living or dead, is entirely coincidental.

  CONTENT WARNING: This short story contains adult material with explicit sexual situations and language. All sexually active characters in this work are 19 years of age or older.

  Table of Contents

  Cougar Confessions: Alicia

  A Note from Jessica

  Cougar Confessions: Alicia

  Alicia wasn't sure why she let her friends drag her to places like this. The drinks cost too much, the music was too loud, it was hard to see and everyone was half her age. She sat at a table in the corner and sighed.

  Another Friday night on the town, she thought. Another lonely Saturday morning with a hangover.

  She nursed her Cape Cod and waited for her friends to come back to the table. At 42 she was the oldest of the group by a long shot. She had met her young and wild friends at work and quickly replaced her boring old married friends with them. She thought they would be just the shot in the arm to get her back out on the dating scene. It had been five years since her divorce and she'd only had sex twice since then.

  A young man walked by and stopped, looking her up and down. He smiled and began to walk over to her table. She liked attention, but hated it when they were sleazy about it.

  "Hello beautiful," he said with a goofy smile on his face. "Where have you been all my life?"

  She couldn’t help but laugh at his feeble pickup attempt. "Son, my life was half over before yours began."

  "Wow," he said putting his hands up. "Hostile. Have fun old lady."

  He turned and walked away, leaving her alone again. She should've been offended by what he said, but she didn't feel anything. She was old, compared to these kids. She was taking her first legal drink while they were sucking on their mama's tit. Besides, that kid was short and skinny with a smile like a jackal, definitely not her type. Also, she felt like she was twice his size. She wanted a man that was going to break her, not one she would break.

  A wasted night, she thought. And I thought I looked sexy tonight too.

  She had picked out a short black skirt that made her thick legs look just a little longer. She wasn't the skinniest girl, but she wasn't fat either. Her friends had described her as "thick" like it was a good thing. She didn't have a tiny waist, but her large breasts drew all of the attention. Usually the only men interested in her were black guys, but she didn't know if she was ready to take that plunge.

  "Come dance!" she heard from her left. Her tiny, cute friend Lyssa had wandered up to the table, drunker than she should be this early in the night. "You're just sitting over here by yourself, it's making me sad."

  "It's ok," she said taking another drink of her Cape Cod. "I'm just having a drink, loosening up."

  "Shots!" Lyssa yelled slamming her hand on the table. "Shots is what we need to really pick this up!"

  "No, I don't think I can," she started to protest but Lyssa had already turned and begun yelling for a server. A boy with a tray quickly made his way over to them.

  "Yes m'am?" he asked.

  "Four shots of Patron my good man!" Lyssa said. When he spun around she slapped him on the ass. Alicia caught the smile that crept across his face as he hurried away.

  "I wish I was as bold as you," she said.

  "Girl, you just have to do," Lyssa said. "You know there's no try, just do."

  "What's that from?"

  "Star Trek or Star Wars or some bullshit. I don't know, my ex-boyfriend was a total geek. I can't believe I stayed with him as long as I did."

  "Are you talking about Aaron? I thought he was nice."

  "Too nice, and too boring! He's probably at home whacking off to anime or something."

  "Well that's not good," Alicia said. Although, if she was home she'd probably be reading a trashy romance novel before a goodnight session with her battery operated boyfriend. Poor B.O.B was overworked these last five years.

  The serving boy returned with the shots, a cheesy smile on his face. "Here you go ladies."

  He picked one of the shots up, obviously misinterpreting the ass slap he'd received earlier.

  "What the hell?" Lyssa said. "That's not for you, give it here."

  She yanked it out of his hand and had it down her throat in one swoop. "Damn that's good."

  After she paid he left, dejected while Lyssa laughed. She loved to pick on men, before picking one to take home.

  "Are you going to have three shots?" Alicia asked.

  "What? Girl two of those are for you!"

  "No, I really can't."

  "Yes you can girl, just do it," she picked one of the shot glasses up and stuck it between her breasts, which were much smaller than Alicia's but still perky. "Take it from here."

  "Lyssa stop that!"

  "Come on just grab the shot from between my tits, do it!"

  Alicia became very aware they were being watched by every guy in their vicinity now. Finally bowing to peer pressure she leaned over and grabbed the shot with her teeth and took it from between her friends boobs.

  "Hell yeah!" a guy from beside them yelled. He was joined by other hoots and cheers.

  Alicia felt embarrassed, but the tequila had an immediate calming effect on her. She grabbed the other shot and downed it quickly. She was determined to actually have some fun tonight, no more sitting in the corner nursing a Cape Cod while all her friends got laid.

  * * *

  "Too many of these girls are just stupid sluts," Ben said, looking around. "They all suck in bed and expect you to worship the ground they walk on."

  "I hear that," Rob said. "But, I still want to put my dick in one of them."

  "You'd put your dick in anything," Ben said. "I'm going to get another beer, you want one?"

  "Yeah, sure," Rob said, his attention taken away by a girl shaking her big ass right in front of him.

  Ben walked away from his friend, wondering why he always came to these places. He was only 23, just out of college, but he felt like he couldn't identify with anyone here. His life revolved around going to work, going to the gym and then going home. Two nights a week he went to hockey practice and on Saturday's he played in a local league. He was in great shape, round shoulders, chiseled abs and decent biceps. He wore his sandy hair long and shaggy and kept a five o'clock shadow at all times. The girls seemed to love it, too bad he didn't love them. Every girl he met wanted to change his routine. They wanted him to skip the gym or practice and take them shopping, or they wanted him to skip the hockey game to go to brunch with friends. He didn't even want to think about the sex, it was usually horrible. Most of the girls interested in him had tight bodies but, to him, it was like fucking a dog bone. He usually intimidated the chubbier girls, so that was a no go too. He just wanted to find a girl that was down to fuck, but also just wanted to come over and hang out with him at night, or come to his games and cheer him on.

  "What do you want?" the bartender asked, in a hurry due to the insane traffic in the club.

  "Two Bud Lights," he said with his money ready. He knew how this worked, if you wanted good service you either had to have big tits or be quick. The bartender would avoid you i
f you took forever every time you came for a drink.

  Ben tipped him the change and walked back looking for Rob. Two people he didn't recognize were occupying the table they previously shared.

  "Son of a bitch," he muttered to himself. Rob could be anywhere: bathroom, dance floor or getting a blow job in his car. Ben had waited around outside for Rob one night in the cold before finally walking back to the car to find Rob in the front seat, his head thrown back and an expression of pure joy on his face. It was when Ben saw the head bobbing up and down in front of the steering wheel painting the picture for him. He couldn't get Rob's sex face out of his mind for several weeks after that, and it disturbed him still to this day. He shuddered thinking about it again and decided to make a loop around the club.

  He was wearing a tight polo and baggy jeans, drawing looks from girls all around. He nodded politely and smiled at a few all while double fisting his beers. He finally got tired of that game and stopped just outside the dance floor. He knew he had no rhythm, so he generally avoided the dance floor like it was made out of hot lava. Instead he just bobbed his head and swayed back and forth in place.

  He stood in that spot for several songs, downing both beers. The music was starting to get to him and he was feeling the alcohol. He left his comfort zone and started dancing a bit more wildly in the spot he was standing in, not caring who was watching.

  * * *

  The alcohol had really taken Alicia over, leaving her with a warm feeling all over her body. Her extremities felt tingly and detached from the rest of her.

  "Oh my god girl," Lyssa said. "Look at that guy!"

  Alicia looked over to the table next to them so see a tall, well built young man dancing awkwardly in place. She studied him for a second, his polo shirt was pulled tight over his broad, muscular shoulders and he had a shaggy look to his hair that excited her just a bit.

  "He looks like a fool," Lyssa said, still laughing.

  "I think he's adorable," Alicia said. "Look at those shoulders."

  Lyssa studied him for a second, looking him up and down, before grabbing Alicia by the arm. "Go dance with him girl!"

  "No," Alicia said pulling away. "I can't."

  "Fine then," Lyssa said, tapping the guy hard on the shoulder.

  He spun around, looking a bit confused. "Yes?"

  "My girl here wants to dance with you," Lyssa said leaning in close to him. "Do you want to dance with her?"

  The man turned around, looking Alicia up and down, before smiling. "What's your name?"

  "I'm Alicia."

  "I'm Ben," he said, politely extending a hand. "Can I have this dance?"

  Alicia giggled at his goofy charm. "Of course."

  They moved out onto the dance floor, getting close to one another. Lyssa had taught her how to dance to this kind of music before, but she wasn't really sure it was appropriate. Ben maintained a safe distance, probably not wanting to offend her. She liked that, and wanted to move closer to him. She moved in, barely touching him with her large breasts, and he responded by putting one arm around her lower back and moving his leg just in between hers. Together they danced to the music, moving in rhythm together.

  "You're very cute," he said to her. "I like a more mature woman."

  "Well thank you," she said, feeling her face go flush. "You're very cute yourself." She couldn't help herself after that, she rubbed her hands over his broad shoulders, almost crying out at how hard they were. "Do you work out?"

  "I play hockey," he said.

  "I hear that's a tough sport," she said. "Have you ever been hurt?"

  "I had knee surgery in high school," he said. "That's probably why I just play rec league now. Oh I love this song!"

  A harder rap song came on, one that required faster movements. Alicia had been getting into his dancing, and didn't resist when he moved behind her. He had both his hands on her hips and was dancing hard behind her, still maintaining a safe distance. As the song continued she got closer and closer to him until her round ass was placed firmly against his crotch. Mimicking what she saw from the other girls she grinded it up and down on him as he wrapped his arms completely around her and put his face close to her neck.

  She began to feel his manhood getting harder as she grinded on it. The alcohol took over and she reached behind her, squeezing his hard penis, before releasing it. This was all the hint he needed, he began kissing her neck and one hand traveled up to the bottom of her breast, squeezing it before returning to her hips, and then down to the tops of her thighs.

  She could feel herself getting more and more turned on, the heat between her legs was evident. She continued to grind her ass into his hard member, feeling it pushing against her. Finally, she couldn't take it anymore and she spun around pulling it against her crotch and kissing him as hard as she could.

  * * *

  Ben hadn't been this turned on by a girl in a long time. Alicia had thick white legs that looked perfect in her high heels. He hated bird legs and she had anything but that. Her ass was round and just the right size. He knew she was much older than him, but he didn't care, that turned him on even more.

  He couldn't believe she had grabbed his dick right there on the dance floor and now she was turning around to face him. She put both hands on his face before forcefully pulling him in for a kiss. Her tongue slipped into his mouth immediately and he responded with his own. They stood there, pressed against one another, kissing passionately before she finally pulled away.

  "This may be forward," he said. "But do you want to get out of here?" He hoped she would say yes, Rob had abandoned him, and he didn't want to call a cab later. Plus, she was one of the most attractive women he had met at this place in a long time. His dick kept getting harder thinking about her out of that dress, bouncing up and down on him.

  "I don't know," she said, looking away. He could tell she was clearly nervous.

  "My friend left me," he said, changing tactics. "I came with my friend Rob and he bailed on me, he has the car keys too."

  "That's not good," she said. "I can take you home, and maybe get your number?"

  "I'd like that," he said. "We can get dinner sometime this week."

  "I'd love that," she said, smiling. "Let me go tell my friend I'm leaving."

  He quickly walked to the exit, waiting for her to meet him. He was nearly bouncing with excitement as she walked up, a smile on her face. "Let's go cutie."

  "After you beautiful," he said, opening the door. He caught the smile on her face after his compliment.

  They walked to her car, a large SUV, and got in. He told her where to go and without hesitation she drove off.

  "So what do you do for a living?" he asked her, leaning over the center console so he was close to her.

  "I'm a school teacher," she said. "I teach sixth graders."

  "Oh, that sounds like a handful."

  "It is," she said, laughing. "What about you?"

  "I do graphic design," he said, putting his hand on the top of her thigh. She didn't make any moves to slap it away or move her leg. He began to slowly massage her thigh, hoping she was enjoying it. "I just started, but I love it."

  "I've never known someone that does that," she said, getting a bit breathless. "How far away did you say your place was?"

  "Actually, turn right up here," he said. "We are nearly there, I don't live far."

  He continued to massage up and down her leg, knowing she was enjoying it. He slid his hand up her skirt, flipping the bottom of her panty line with his finger.

  "You're bold," she said.

  "You're beautiful," he shot back. He moved his hand over the top of her panties, stopping on top of her pussy. He could feel the wetness in her panties and began to slowly massage her clit through them. She began to breath heavier, getting into the sensation. He took two of his fingers and began pushing the panties into her opening before moving back up to rubbing her clit. Before long her lips were out and around the panties, getting his fingers wet. She was still driving, but
breathing very heavy and slowing down.

  He looked up, just to see her almost drive by his house. "Stop, right there!"

  She barely slowed down and whipped the car into the driveway, coming to a stop inches from his garage door. Excitedly she threw the car into park, unbuckled her seat belt and grabbed him, pulling him over and putting her tongue in his mouth again. He continued to rub her clit as she moaned in between kisses.

  "Do you want to go inside?" he said.

  She didn't respond with words, only an eager nod.

  * * *

  Alicia followed Ben into his house. It was a smaller house with only two bedrooms, perfect for a young man just starting his career out. He opened the door and lead her through. Once inside he pounced.

  She squealed with delight as he grabbed her, spinning her around and violently kissing her down the neck while his hand reached up the back of her dress, squeezing her ass hard. She felt his powerful arms wrapped around her and enjoyed the feeling of being manhandled.

  "I want to fuck you so bad," he said to her in between kisses. "I love your body."

  "Fuck me," she said as he continued to kiss her. "Do whatever you want."

  She yelped as he lifted her off the ground, throwing her over his shoulder. She had never been with a man so strong. He walked her down his short hallway, kicking the bedroom door open and tossing her onto the bed. She hit with a bounce and laid there, waiting for him.

  He slid his shirt up over his head, revealing hard abs and a perfectly chiseled chest.

  "I love your body," she said, licking her lips.

  He didn't say a word, he just slid his hands up her skirt and pulled her panties out from under. She reached down to take off her high heels, but he stopped her. "Leave those on, the whole time."

  He then pushed her back onto the bed and lifted her skirt, revealing her wet pussy. He laid down in between her legs and started rubbing his fingers up and down her opening, teasing her clit each time he went up. She moaned in delight as he put two fingers inside of her and began to thrust them in and out.