Cougar Chronicles: D Is for Diana

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(First my apologies for this being out of order. It disappeared from my computer after I thought I had posted it. Hope it’s worthy of your time)

Chapter 1 :

The 18 year old high school student Jeff Gordon couldn’t believe what was transpiring. Forty-eight year old Mrs. Diana Dennison, his best friend’s mother, was sucking the purple head of his cock and jerking the shaft at the same time. It was the best blow job of his young life because another lady from the neighbourhood, recent divorcee 44 year old Chrissy Canyon was behind him with her nose buried between his ass cheeks. At the same time, she had her hand between his legs and she had his balls in her hand.

“Nothing could be better than this,” he thought. “Two gorgeous MILFs servicing me!” His “oh gods” were drowned out by their muffled “oohs” and “aahs.” This went on for what seemed like an eternity but which was in reality just a few minutes.

Diana took her mouth off Jeff’s cock but her hand never stopped. Looking up into his dark blue eyes she asked, “Like it baby? Like having two women suck your hard young cock?”

The teen could only grunt his approval as he put his hand on the beck of her neck and urged her to take the purple crown back into her moist hot mouth. At that moment, Mrs. Canyon crawled around until the two cougars were sharing his rock hard erection. When the two met at the head they would exchange open mouthed kisses which were especially erotic to the teen who had only ever seen two women kissing in porno movies.

While one lathered his cock with her tongue or sucked on its crown, the other would lean under and using her hands pull his testes into her mouth and proceed to suck his balls. They both were experienced enough to know that no man, especially one so young, would last long with such attention as they looked into each other’s eyes enjoying the effect they were having. Jeff was getting closer and closer and the two experienced cocksuckers sped up their ministrations.

“Oh God! Oh God! I’m gonna…I’m gonna cum! Yes! Yes! Uhhhhh…I’m cumming!!!!!” he roared to the world.

And cum he did. More cum shot out of his cockhead than either woman expected. Indeed, more than either had ever seen or experienced. And as fate would have it, the bedside phone rang at almost the exact same time. No one was about to stop to answer it.

The first spurt shot straight into Diana’s open mouth hitting her tonsils so hard that she instinctively closed her mouth and swallowed. Jeff’s second cannonade bounced off her cheek and deposited itself in Mrs. Canyon’s right eye. Undeterred Chrissy gobbled the boy’s spurting fountain into her now open mouth just as his third and fourth offerings shot out. While she was content to let the 18 year old finish in her mouth, she didn’t object when Diana pulled Jeff’s still erupting cock out and back into her mouth.

The teen just stood there enjoying the moment as his cum continued to trickle out especially as Mrs. Canyon was still jerking his shaft and encouraging him. “Keep cumming baby! Give Mrs. Dennison all you got! Yeah baby look at her swallow your cum! Oooh, that’s so nasty!” Meanwhile the phone continued its irritating ring.

Indeed, Diana Dennison was enjoying every drop she could elicit from her young lover. Finally he was empty and groaning almost in pain now. Diana allowed her new best friend and confidante to pull his cock out of her mouth and the two cleaned every last speck of cum from his cock and then licked the residue residing on each other’s faces. The spent teen collapsed back onto the bed and watched his two older neighbours in awe. They were now French-kissing each other almost oblivious to the teen. Finally the shrill ringing had gone on long enough that Mrs. Dennison reluctantly broke from the kiss and picking up the phone bellowed angrily into the receiver, “What?” which was not exactly what her husband had expected.

It’s probably just as well that the cuckold couldn’t see the picture being presented. His wife while trying to explain why it had taken so long to answer was getting more and more agitated with him. She still had traces of her young lover’s cum on her chest and tits and their real estate agent was doing her best to lick all the evidence clean.

Meanwhile their 18 year old neighbour , lay back with a satisfied smirk on his face, head propped up on a pillow, obviously basking in the aftermath of being seduced by the two matrons. He couldn’t believe how this day had turned out. He had just finished playing a tennis match when the two older club members had invited him back to the Dennison home ostensibly for a swim. It hadn’t taken them long to lure him into the upstairs bedroom.

The Dennison’s were now obviously in the middle of a heated argument. Finally, Diana shrieked, “Yeah, well, you bastard! I just finished sucking off the neighbour’s kid in our bed. What do you think of that?” Then she smashed the handset down into its cradle. The room became deathly silent.

Chapter 2 :

Diana Dennison was driving Highway 400 in her brand new convertible canlı bahis with her son’s obviously smitten best friend Jeff Gordon. They were on their way to her cottage in Wasaga Beach for a weekend of unbridled sex.

The teen couldn’t keep his eyes off her. In spite of the fact that she was 48, she looked ravishing especially to the always horny teen. Her short denim skirt rode halfway up her sleek, tanned thighs and the thin, low cut tank top barely concealed her 34 inch breasts. Her long black hair which had just a touch of grey blew softly in the breeze. The cougar was enjoying the effect she was having as she stole quick glances at his crotch. Noticing the bulge, she deliberately spread her legs farther which of course caused the skirt to rise even farther. It was almost to her crotch now.

Coincide that with the knowledge that her husband of 24 years and she were now officially separated, the older woman started picturing the youth on his knees pleasuring her again. Just the thought was making her moist and she reached across the console to rest her palm on his now obvious erection.

“Take it out for momma, baby,” she purred. “Let me see what you’ve got for me.”

Jeff, who had groaned when the older woman had put her hand on him, didn’t have to be told twice. “Mrs. B. you are nasty! Whenever I visited your house or saw you at the club, you always seemed so prim and proper.” Even saying this his zipper was down faster than some of Mike Tyson’s early opponents.

Trying to keep her eyes on the road ahead was difficult for Diana as she tried to steal a glance at the teenager’s long, fat cock now standing up proudly. The young man she and Chrissy Canyon had seduced for the first time a month ago took her hand and guided it to his dick. It didn’t matter that Chrissy was sleeping with the boy too as he always seemed to be able to get it up. “Oh the joys of being young,” she thought wistfully.

Meanwhile. knowing that the older woman couldn’t get enough of his cock emboldened him to say, “Oh yeah, Mrs. Dennison, play with my cock. Oh fuck yeah! Like that!” He leaned back and enjoyed the gentle stroking. He relished the older woman’s playfully squeezing the shaft as she drew her hand upwards. Then one of her fingers would touch the slit at the end of the penis and he would groan. Every so often she would take some of the pre-cum that was leaking out and tantalizingly bring it to her lips. They both knew it wouldn’t be long before she would bring him to completion.

“Fucking A!” he thought. “Bobby’s mom jacking me off while she’s driving.” He wished he could brag about it to the world but knew that would be the end of his friendship with his best friend.

Suddenly her hand returned to the steering wheel as they were cut off. Diana had to swerve to avoid hitting the van that had crossed in front of them. “Stupid asshole!” Mrs.Dennison shouted.

Jeff saw her bosom rising and falling from the sudden outburst and he boldly reached across to cup her right boob.

“Hmmm, hon, that’s nice but I think the other cars might see that. Might cause an accident if someone sees a handsome young stud mauling an older woman’s tits in public. I know a better place for your hand. One not so conspicuous.” With these words she took his hand and guided it between her stockinged thighs.

Jeff didn’t need any further guidance. By now he had become quite adept at getting his older lover off with his fingers, mouth and cock. She and Mrs. Canyon had taught him well. Starting at her knee, Jeff tenderly squeezed and kneaded her thigh as his hand slowly inched its way up and under her skirt. Moving to the inside of her leg, he gently forced her legs even farther apart until he reached his goal.

“Why Mrs.Dennison, you’re not wearing any underwear,” he announced pleasantly surprised. “Did you plan this?” He smiled saying this as the cougar never ceased to amaze him with what she was willing to do. She was so unlike his own ultra-conservative PTA mother who was the same age. “Damn,” he thought, “she’s not like any woman I’ve ever met!”

“Hmmm, hon, thought you might like to get nasty on the way,” she acknowledged huskily as the teenager’s finger invaded her pussy. She spread her legs even wider to allow him easier access. Her plan on using her boy toy for the weekend was getting off to a great start.

Now having free reign, Jeff started giving it to her good. He would slowly insert a digit in deeper and deeper and then as he tantalizingly withdrew it, he would tease her clit with his thumb.

“Oh god, baby, you are one talented young man,” she gasped squeezing her thighs together which trapped Jeff’s finger while it was still in her. “Keep that up and I’m going to get us in an accident. I think we better find us a spot to pull over.”

Scanning the horizon for a possible pit stop, Jeff took her hand and guided it to his forgotten hard on.

“I don’t see anything, Mrs.B.. Why don’t you just pull over and put the top up.” He had returned to frigging the excited woman with fervour.

“Uh…uh…oh…B..B…Jeff…you..oh my god, I’m bahis siteleri gonna cum!” and raising herself up off the seat, she did. Amazingly, she did not lose control of the car but as she came, she had slowed down enough to raise the ire of the driver behind her. He gave her the finger as he swerved around her. Giggling she grabbed Jeff’s wet digit and had him give the surprised guy the wet one finger salute. By now she was pulling off the road and activating the canvas top even as they were coasting to a stop.

As soon as the car was covered and the engine barely turned off , the two illicit lovers were quickly scrambling into the back seat, divesting themselves of their clothes as they went.

“Hurry up, lover! I need to be fucked so bad! Give me some of that gorgeous hard young cock!” she hissed.

Jeff being younger and more athletic had his pants off and was proudly stroking his manhood while now leaning back on the rear seat.

“It’s all yours, Mrs.B. but give me some head first,” he boldly told her while stroking it. The teen had come a long way from the naïve high school student she and her best friend had seduced. They had taught him well and he was now an equal in their erotic sessions.

Smiling at being guided by a boy young enough to be her son and needing no further encouragement, Diana Dennison, slid to her knees between his long legs, reached for his rod and started stroking it with one hand while at the same time grasping the teen’s testicles in a vice-like grip forcing a gasp and a groan from the boy. She worked the two most sensitive parts on a male like she was afraid they might escape. In fact the grip she had on his testes made them look like each individual ball might explode. The pressure of her grip caused each ball to turn purple.

She looked up into his wide open eyes while stroking his thick six inches of manhood.

“Tell me what you want baby. This one’s for you. Tell me what you want me to do,” she ordered.

“Oh God! Oh fuck! Put it in your mouth! Come on Mrs. B., put it in your mouth or…or else..oh my god, I…I can’t stop! I’m gonna fucking cum!” By this time his hands were in her hair and he was trying to force his cock into her mouth.

Knowing he was too far gone, rather than stop him, Diana decided to let the teen dump his first load. “It’s okay baby, give it to me! Cum on my face! Cum for me baby!” She continued stroking and looking up at the anguished face of the 18 year old.

His first explosion caught her in the right eye and she instinctively pulled back. His second spurt hit her flush on the nose and some even shot up her nostril causing her to gasp. This opened her mouth and Jeff’s third jet shot in unimpeded.

His major spasms having subsided, Diana took the still dripping tool and allowed it into her mouth where she completely drained it and cleaned it at the same time. Jeff, who had almost blacked out, watched the pretty mother of two shamelessly finish him off while the thunder of passing vehicles roared by. The wickedness of the scene was not lost on the 18 year old. He had just been sucked off on the side of a highway by his best friend’s mother.

When she finally came up for air, she was wiping cum from her face and cleaning the last traces from her fingers.

“There baby, that should hold you over ’til I get you in my big bed at the cottage.” The two lovers were still dressing and giggling at the wanton act that had just occurred when there was a sudden knock on the side window. They looked up to see the toothless grin of a transport truck driver.

“Y’all finished what yuh was doin?” the laughing man asked with a Southern accent not attempting to conceal his own lust at what had unfolded before him. He had stopped because he wanted to make sure they were alright. The scene of the youth cumming in the older woman’s face was his reward for being a good Samaritan.

“Hey boy, y’all want some help?” he guffawed as they scrambled to get back into the front seat. Without so much as a thank you, Diana started the car and shot out into traffic without even checking for oncoming traffic. Fortunately, there was no one in her lane as she booted it down the highway.

“Oh my God, that was embarrassing,” she confessed, her face now beet-red. Looking back in the rear-view mirror she could see the truck driver waving his hands.

Then she looked over at Jeff who was doing his best to control his laughter.

“What the fuck are you laughing at Jeff? If word ever got out, my reputation would be shot,” she cried angrily.

The teen could not suppress his laughter. “I’m sorry, Mrs.B.. You’re right but…you gotta admit, almost being caught doing something so nasty is a turn-on and I’m sorry but… you’ve still got some cum stuck in your hair. And the guy wasn’t from around here so who could he tell.”

Diana was shocked to feel the traces of cum dangling from her bangs. “I guess you’re right,” she said, “have to admit it was a kick doing it. I’ve never done anything like that. My husband used to try to get me to do things on driving trips in our younger bahis şirketleri days but I always refused. I can’t believe how I’ve changed in the last year or so.”

Noticing the teen still had a hard on, Diana added, “And look at you, Jeff. My god, doesn’t it ever go down?”

Chapter 3:

The weekend had gotten off to one of unparalleled passion between the two lovers. Jeff had been taught how to pleasure women by both Mrs. Canyon and Mrs. Dennison and being only 18, he never had a problem getting it up. No sooner had they entered the cottage when they were fucking on the floor of the cottage. She got off three times before he shot his load into her leaving them both spent and satisfied for the time being.

They went swimming for a cool down period but while playing around in the shallow waters of Georgian Bay, the teen had gotten hard again. Feeling his hard cock against her butt brought out the wantonness in the 48 year old and while watching that other swimmers didn’t get too close, for the first time in her life, Mrs. Diana Dennison let herself get fucked in the water. She had even surprised herself by going down on the teen under the water.

Afterwards, while sunning themselves on shore, Diana noticed a group of young men playing with a Frisbee. She couldn’t take her eyes off one player in particular. He was tall, blonde and very tanned with a physique that only came from frequent workouts in a gym. More than that, he reminded her of her first love way back in high school, Patrick Murphy. Patrick had taken her virginity one night at the local drive-in and she had thought they would be married but that all ended when he went away to college down east and she had lost contact with him. Although she had never seen him again, like all people, one never forgets one’s first sexual interlude.

While mulling over her past, Diana’s statuesque figure was not lost on the youths either. In spite of her age, she did have an incredible body. The Frisbee seemed to be directed her way quite often and the blonde Adonis kept coming over to retrieve it. Each time he would apologize but his eyes seldom left her barely concealed breasts.

She in turn openly admired the young man’s torso, especially his butt and his crotch. A fact that was not lost on either the young Frisbee player or her lusty young companion. Jealousy reared it’s ugly head and Jeff after voicing his displeasure stormed off into the cottage.

Knowing that she would be able to assuage the young man’s ego with another roll in the hay, Diana was not concerned. Rather she relished the moment to make an even bigger impact on the young man with the familiar features. She deliberately leaned forward pretending to adjust her blanket. This caused her breasts to dangle down deliciously. A move that was not lost on the 20 year old.

Looking up into the blue eyes of the young stud, she was again amazed at the striking resemblance to her first lover.

This time he made no pretence of using the Frisbee. He just waved his companions away and sat down beside the buxom beauty and introduced himself.

“No way! You can’t be!” Diana explained after hearing his name. “Your name is Patrick Murphy? No way!”

“Well, if you want to be technical. My name is actually Patrick Murphy Junior,” was his reply.

In an amazing happenstance of fate, Diana had come across the 20 year old son of her first love. No wonder he had looked so familiar.

The two then got into exchanging histories. She told bits and pieces about herself but pumped him for info on his father. Turns out that Patrick Murphy Senior had unfortunately died in a car accident 3 years before. The more they talked the more the young man brought back pleasant memories and at the same time, sensing his sexual interest in her, Diana shamefully started planning her seduction.

“What a blast that would be!” she mused, “Being fucked by Patrick’s son!”

The 48 year old cougar would lean back on her haunches which she knew emphasized her flawless breasts. From time to time she’d flick her head causing her long black hair to billow up and over her shoulder. As they talked, she’d reach out and touch his tanned and muscular arm to emphasize a point.

Diana was mesmerized by the hauntingly good looks of the young man. She couldn’t get over the striking resemblance between father and son. It was like she was with her first love again. Drawing herself closer and closer, Diana could control herself no longer. She reached out and touching his cheek with her long tapered finger, she told the youth how handsome he was. Though she had mentioned that she had known his father, she still had not told him about her sexual relationship with his father for fear of repelling the young man.

She needn’t have worried. There was no way Patrick would have rejected her even if he had known. He was in lust.

Diana looked around to see if anyone was watching. “Say sugar,” she asked seductively, “do you have anyplace where we can…um…get to know each other a little better… if you know what I mean?” She pushed her bikini-covered breasts into him. Her nipples were already noticeably hard. Then to make sure there was no misunderstanding whatsoever, Diana placed her hand on his knee and ran it up the inside of his thigh.

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