tagToys & MasturbationCougar Training

Cougar Training

byzombie22©

Jessica Stevens stood out in the parking lot of the gym and she could feel the first chill of the fall in the air. A pang of sadness coursed through her when she thought of the empty house that awaited her. She also thought of the package on the counter in the kitchen, the unassuming brown cardboard box that her friend Kate had mailed to her after their long conversation on the phone last week. She felt a tinge of excitement mixed with embarrassment.

Jessica had endured the past nineteen years as a trophy wife and mother of two children. Her twins, Ryan and Renee, had just graduated high school earlier in the year and she had just shipped them both off to college. The divorce was finalized just a week after that. Jack Stevens was a well-respected real estate developer and pillar of the community. Jessica's freedom and discretion came at a heavy premium.

Jessica's black Lexus SUV pulled into the garage as the sun disappeared for the evening. The five thousand square foot house was silent until the squeaking of Jessica's gym shoes broke the silence. As she flipped on the kitchen light she noticed the package was just as she left it. She took a deep breath and knew that it was going to take a little liquid courage to break down the last barrier of her inhibitions.

The package had been moved from the kitchen counter to the master bedroom after two full glasses of wine. The curtains were closed and Jessica sat in the middle of her California King bed and used a letter opener to open the box. She gasped when she pulled out a large purple and white bottle of lubrication. Her cheeks flushed as she reached into the box and pulled out a lifelike dildo that had to be at least eight inches long and considerably wide. The dildo came with a suction base that flared out from underneath the pink realistic scrotum. The blood began to rush from her hot cheeks to her now sopping pussy.

It was almost too much to process for Jessica. She had been married to a man nine years her senior for nearly two decades. Finally at forty-two she felt the desire pooling up and threatening to boil over. She started to push the box away and off the bed when she realized that she hadn't totally emptied it out yet. She flipped the box over and the remaining contents fell to the center of her bed. She noticed the unmistakable shape of a DVD box and a sizable blue butt plug.

The sight of the butt plug awoke something deep within Jessica, a feeling that she had never felt before. Her body shook slightly as she picked up the plug and held it in her hands. An aching inside of her began to build. She knew that she had to act now before it became unbearable.

Jessica walked over to the large flat screen television mounted on the wall across from the bed. She caught her reflection in the mirror and realized that she was still in her gym attire. Her light brown hair with tasteful blond hi-lights was pulled back in a ponytail. Her white sports bra and tight black yoga pants covered up a body that was the envy of most of the ladies in her Pilates class. Her visage in the mirror stoked her excitement. She finally realized that she was due the pleasure that she had been denied for years.

Stripped naked she crept towards her bed. The heat was radiating from her as she felt tiny drops of sweat building up at the small of her back. She flipped open the cap on the bottle of lubricant and poured some into the palm of her hand. She massaged her breasts and enjoyed the feeling of wetness and pleasure as the lube coated her body. The blue plug caught her eye first and she poured copious of the lube onto it. She positioned herself on her stomach and propped herself up on her elbows as her knees lifted her ass in air.

The tip of the plug brushed against her rosebud and it caused her knees to weaken. She could feel her pussy dripping onto the sheets of her bed. The gentle push felt slightly uncomfortable at first but Jessica relaxed and timed her breathing with each advance. Little by little she felt the exquisite pleasure/pain of being filled up. Just when she felt as if she couldn't take anymore the plug pushed pass the final bit of resistance and she felt an orgasm rock her body. She glanced back and saw the reflection of her ass in the mirror. The flanged blue base peeked at her and caused another shudder to pass through her body.

The first orgasm was like a baptism for Jessica. All of the repressed feelings of desire and frustration slid away from her. She grabbed the bottle of lube and her dildo and walked towards the bathroom. She wiggled her ass every few steps to enjoy the sensation of the plug still firmly implanted in her. Jessica walked to the full-length mirror near the bathtub and shower stall. She knelt down and attached the suction base of the dildo to the tile floor. Her body was slick with lube and shined in the light of the bathroom.

She squatted down over the dildo and rocked back and forth to feel the tip of the hard shaft brush across her clit. The feeling of the plug and dildo simultaneously inside her caused another orgasm to jolt through her. She started to bounce on the dildo slowly at first but the desire to cum again compelled her to increase the pace. She writhed in pleasure as she climaxed again.

The coolness of the tile floor helped Jessica recover from last orgasm. The site of the dildo still standing up crudely fanned the flames inside her once more. She knew that she had to push herself to an area of true awakening. She slowly pulled the blue plug from her bottom and felt the need to be filled again. She wondered if she would really be able to accommodate the massive dildo that called to her. She poured the lube on the waiting phallus and thought about the breathing exercises that she had learned from years of Yoga and Pilates.

The tip brushed against her ass teasingly at first until she steadied it with her hand. Rocking on her knees she felt it push pass initial entry. She rubbed her clit as she slowly worked her way down the shaft, each inch opening new realms of pleasure. Her pussy had never been so wet. It was dripping with increasing intensity as she moved. Moaning louder as every second passed she finally felt fake scrotum touch her ass cheeks.

She opened her eyes glanced back at the mirror. She could see that the dildo had disappeared inside her ass. She began to move up and down slowly. She relished the feeling of being filled up as much as she possibly could. She increased the pace of her movements and started to rub her pussy again. The last barrier was about to come crashing down. The explosive rush of an orgasm shot through her once again. The intensity was more that she had ever felt before. Her pussy squirted all over the tile floor and her body convulsed with pleasure. Black spots popped in front of her eyes as she nearly passed out.

Jessica cleaned herself up as best as she could and collapsed on he bed. When she woke up nearly ten hours later she realized that her mind had reached a state of ideal clarity. She pleasure and experienced that she had denied herself were available to her anytime she wanted, Jessica wasn't about to waste anymore time.

The period of clarity lasted all through Jessica's productive morning. A quick breakfast followed by a 5-mile jog to round out her morning seemed to be just the thing to extend her mood. Stopping off at the local coffee house to get a refreshing drink and finish the morning paper was also on the menu, until the sight of a familiar face caused the feelings of lust to begin to rise.

Behind the counter quickly preparing drinks was her daughter's ex-boyfriend, Mark. Renee had broken up with him just before leaving for school and it had broken his heart. Mark even stopped by one afternoon just to say hello. Jessica felt pity when he showed up that day; her feelings now were totally different. He was a handsome young man that stood close to a foot taller than Jessica at six foot three. He was going to attend the same university as Renee and Ryan, on a football scholarship, but a nagging knee injury dashed his hopes and he was attending the local community college until he could attempt to walk on next fall. When Mark, saw Jessica his eyes lit up.

"Mrs. Stevens it's great to see you"

"Very nice to see you to Mark, and please just call me Jessica. Mrs. Stevens seems awfully formal."

"Sorry, Jessica. What can I get for you?"

"Just an iced green tea. I need something to cool down from my jog with."

"It is getting pretty hot outside. You look great, if you don't mind me saying."

Jessica felt a flash of embarrassment rush through her after the compliment. She was wearing a small pair of black mesh running shorts that highlighted her tan legs and a purple sports bra. Her hair was pulled back in a ponytail and her face looked fresh sans any make up.

After some small talk Jessica sized up the young man and knew that she had to take action. Her new attitude and freedom demanded it. She asked Mark what time he got off and made up a convenient story about how Renee had left behind a few things that belonged to him. Mark eagerly took the bait and said that he would be over when his shift was over in two hours.

The wait was nearly unbearable. Jessica came home and quickly showered but paused to use the massage setting on the showerhead to bring her to a quick climax in order to stave off the nearly overwhelming tide. She wasn't sure what outfit would work best to seduce Mark until a spark of an idea drew her to Renee's room. She looked through Renee's chest of drawers and found that she had left several pairs of panties behind and a pair of faded and well worn jeans in the closet. She pulled on a tiny powder blue thong and the pair of jeans and a threadbare white cotton tank top with no bra. Renee inherited her mother's petite frame so the clothes fit Jessica well. Jessica's fuller hips and breasts made the clothes seductively tight. Jessica felt her pussy begin to pulse with excitement when she noticed that a hole in the crotch of the jeans exposed her thong slightly.

When the doorbell finally rang it startled Jessica almost out of the chair that she was relaxing in. She felt the butterflies in her stomach at war with the desire coursing through her body. She had to show some self-control and just not fall on her knees with the hopes that Mark's cock would be at the ready. When she answered the door she noticed that he wasn't wearing a shirt and that his bike was propped up near the garage.

"Out for some exercise too I see."

"Yeah I'm trying my best to stay in shape and biking is better for rehabbing my knee than jogging at this point"

"Come in and sit down for a few moments and get out of the heat."

"Sure just let me grab my shirt off of my bike"

"Don't worry about it. You saw me in my jogging bra this morning. "

Mark felt a lump in the back of his throat. He was standing shirtless in front of his ex-girlfriend's mother. All the guys at school made remarks about how Jessica was actually hotter than Renee. He hadn't really thought about it until this exact moment. He also noticed that Jessica was wearing a pair of Renee's jeans, and not just any pair either. Renee always put on those jeans when they were going to fool around. There were a few discrete and not so discrete holes that provided easy access to her pussy and tight little asshole. He wondered if Jessica knew about any of it. The thought caused his cock to stiffen and had to shift slightly to prevent it from crudely tenting his jogging shorts. He tried his best to make small talk until Jessica invited him up stairs so he could retrieve the items she had invited him over for.

Jessica led Mark past Renee's room and into the master bedroom. His cock began to swell even more when he realized that Jessica hadn't been truthful with her intentions. The look of lust in Jessica's blue eyes was more than evident.

Mark bent down to meet Jessica's eager lips. She felt as hot as a furnace against his bare chest. She quickly reached to pull down his shorts and felt his hard cock pressing against the fabric of her tank top. Just as he had done many times before, his hands found the perfect opening in torn denim and he began to massage Jessica's wet pussy.

Jessica gasped at Mark's expertise and she felt an orgasmic jolt shock her when she realized what the holes in the jeans were for.

"Fuck me like you fucked Renee"

Mark swept up Jessica in his arms and lay her face down on the bed. His cock met Jessica's waiting mouth as he leaned over her and ripped open the one discrete hole. Jessica's panties were pushed to the side as his fingers pushed into her saturated pussy. Craning her neck up she took more of his sizable cock into her mouth. Mark pushed his cock faster to meet Jessica's rhythm. Jessica came again when she felt Mark's tongue begin to push into her ass. Jessica's moans pushed him over the edge. Mark shot cum into Jessica's eager mouth.

A few moments passed before either of them moved. Mark lay on his side with his head still near Jessica's ass. His cock looked painfully hard to Jessica when she decided to make her next move. She pulled off her tank top exposing her full breasts and began rubbing them slowly against Mark's shaft. He began to pull off Jessica's jeans before she stopped him. She had no intentions of taking them off. She directed Mark's strong hands to the thin side straps of her thong and he tore them apart quickly.

Jessica threw the remnants of the powder blue thong on the floor as she straddled marks now supine body. She relished the feeling of his cock brushing against her pussy and most especially her ass. With out penetration she began to slide back and forth against Mark. The sensation of her clit rubbing on his pelvis sparked a tiny orgasm that began to build into something bigger. She felt Mark's cock finally delve into her.

"Fuck me" She said.

Mark thrust up into Jessica with a building intensity as he met Jessica's downward momentum. Each time his cock reached the hilt Jessica shook with pleasure. The moment of fulfillment was approaching for each of them. Jessica gasped and came when she felt the intense heat of Mark's cum filling her up. She collapsed on the bed and felt the clarity of purpose and freedom wash over her.

"I hope you know that this is just the beginning," She said to Mark.

Two days had passed since her adventure with Mark and Jessica felt the feeling of satisfaction and clarity begin to wash away. She began to think of all the erotic possibilities that she had been deprived of and wanted to waste no more time on being idle. After brisk mornings run in the rapidly chilling September air she sat at her breakfast table and pondered her next course of action. The familiar buzz of an incoming text message perked her interest. She picked up the phone and saw a simple message from her friend Kate.

"Are you busy tonight?" was the message and it immediately improved Jessica's mood. She had been dying to inform Kate that her package was not a waste of money; in fact it had opened up a whole new world.

After exchanging nearly a dozen cryptic messages, Kate invited herself over for dinner and drinks that evening. Jessica was mildly disappointed that they weren't going to head out for a club or bar, but decided that the quiet and privacy of the house would be the best place to admit her debauchery.

Kate Overton was a friend that Jessica had quickly bonded after their first meeting in Pilate's class. Kate was freshly divorced and was quick to lend a friendly shoulder to cry on as Jessica became sure that her marriage was going to end as well. Jessica was a petite brunette with piercing blue eyes. She was adept at Yoga and Pilates but managed to maintain a curvy almost zaftig appearance. She was by no means fat, but her hips and breasts were more reminiscent of a 1950's era pinup than an over exercised soccer mom. Kate's sixteen-year marriage had not produced any children and she was thankful for it.

It was nearly six in the evening when Jessica noticed Kate's sleek black coupe pulling into the driveway. Jessica was dressed in a comfortable grey sweater over a thin white tank top and black yoga pants. She felt underdressed when she saw that Kate was wearing a white cocktail dress with a plunging neckline and black stiletto heels. She was also carrying a black overnight bag over her shoulder. Jessica felt her mouth become dry and wave of nervous excitement rush through her.

"How are you doing sweetie?" Kate asked as Jessica answered the door.

"I'm doing great. Even better now that you are here." Jessica answered.

Chinese food was delivered within the hour and a bottle of wine was quickly drained in nearly the same time. Jessica confided every detail of the past week as the effects of the wine loosened her lips. Kate seemed pleased but not surprised at the news.

"I am very proud that you have decided to let loose for the first time in your life" Kate said after hearing Jessica's tale.

"You don't consider me a brazen slut?" Jessica asked with a giggle.

"Far from it honey, in fact I want you to know that you should have done this a long time ago" Kate said.

A second bottle of wine was uncorked and glassed quickly filled. The wine caused a flush of heat wash over Jessica's body and she decided to take off her sweater. She noticed Kate's eyes focusing on her full breasts underneath the thin material of her white tank top. Jessica stood up quickly and picked up her glass of wine and decided to move to the living room couch. Without any prompting, Kate picked up her glass and the black bag and followed.

Kate sat down close to Jessica and they sat in silence for a few moments. Each could feel the tension building in the air. The creamy skin of Kate's thighs became more visible as she began to shift in her seat. Just as Jessica was about to make an awkward effort to break the silence, Kate announced that she had to go to the bathroom. Jessica noticed that on her way to the bathroom Kate took along the mysterious black bag.

Jessica felt the buzz of the wine as she attempted to pick out a suitable mix of music on the stereo. Just as she settled on the right mix she heard the sound of Kate's high-heeled steps coming closer.

"I hope that you don't think that I'm a brazen slut," Kate said in a sultry voice.

Jessica gasped slightly and felt her head spin when she caught sight of Kate. Kate stood unashamedly in front of Jessica in a tight black leather corset that covered her stomach but left her breasts exposed. Sheer black thigh-high stockings and a garter belt matched her tall black stiletto heels. This outfit was enticing enough to Jessica, but the vision of a thick nine-inch long black dildo jutting out of a strap- on harness pushed her over the edge of hesitation and into unbridled lust.

Jessica instinctively fell to her knees and accepted the faux cock into her mouth. She looked up at Kate and began to suck eagerly. Kate knew that she was now in control of the moment and ordered Jessica to strip off her pants and get on her hands and knees. Jessica slowly pulled off her black yoga pants and crawled seductively towards Kate in her thin white tank top and tiny white thong panties. She shook her ass invitingly towards Kate.

Without a word Kate dropped to her knees behind Jessica and pulled her panties to the side before licking the succulent pussy in front of her. Jessica's moans began to drown out music as she felt her orgasm building. The moment she felt Kate's skilled tongue push into her ass she lost all control and waves of pleasure radiated through every part of her body.

There was hardly a moment for Jessica to collect herself before she felt Kate guide her back on to her knees and slowly guide the massive cock into her sopping pussy. The feeling was nearly overwhelming as Kate began to build up a steady rhythm. Jessica pushed back to meet each oncoming thrust. Torrents of ecstasy crashed down as another climax rocked Jessica.

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