An Afternoon in the Cougars Den

An Afternoon in the Cougars Den



The thumping bass sound announced the approach of Miguel’s car long before Damon saw it come around the corner and pull up to the side of the basketball court. Damon took one last shot, banking the ball off the backboard and through the hoop before jogging over to the high chain link fence surrounding the court where Miguel’s car sat on the other side. The passengers side window of Miguel’s Camry slid down and Luke leaned out.

“Yo Adams ,” Luke called. For as long as Damon could remember, all his friends called each other by their last names. “We’re plannin’ to go swimmin’ at the falls. Get in and we’ll swing by your place so you can get your suit. We got three cars full already, and we’re all meeting at Bushy’s parking lot in about twenty minutes.”

Damon’s face drooped, “I can’t come man, I’ve got to be at Mrs. Robinson’s place at three. She’s got some work for me to do.”

Miguel leaned down from the drivers seat so he could see Damon’s face through the passenger window and shouted, “Dude, call the old bitch and tell you can’t make it today. Tell her you’ll do it tomorrow.”

“I wish I could, but I can’t man. I gotta take a pass today,” Damon said.

“But Cara Hinkley’s gonna be there, and I know damn well that you want to tap that ass,” Luke said, holding his hands up while his fingers squeezed an imaginary ass.

Damon shook his head and kicked the bottom of the chain link, while the memory of Cara kissing him came to his mind. He had been interested in Cara since his junior year of high school, and had only recently gotten up the courage to talk to her at a party a few weeks ago. She had been upset with her mother because of some family drama that she wouldn’t discuss, and was busy trying to drown her sorrows in peach schnapps. Figuring that since high school was finished and he had nothing to lose, Damon had told her about his feelings for her, and that was when she leaned in and kissed him on the lips. It wasn’t just a friendly kiss either, there was some serious passion and peach flavored alcohol behind it. Since the party, he had tried to hook up with her again but there was always something that stopped them, and now he was about to do it again. “I can’t make it guys, I promised Mrs. Robinson.”

“Really dude, you’re gonna pass up a chance to see Cara in a bathing suit, so you can go help granny change her adult diaper?” Luke asked while behind him Miguel guffawed at the idea. Luke continued, trying to draw a picture of Cara with his words, “Just imagine that tight, sexy body in a two piece bathing suit man. Her fucking tits all up in yo face dude. Those sexy bluish green eyes of hers, oh man, I’m poppin wood just thinking about her, and you want to go hang with some dried up old cootch.”

Damon bit his lip and suppressed the urge to defend Mrs. Robinson to his friends. They knew that he worked for the rich widow since he turned eighteen, but they had no idea what really took place there. “Look I’m sorry but, Mrs Robinson pays me good money to show up on time. She counts on me to be there, and I can’t just blow her off.”

From the driver seat Miguel laughed, “Yeah, I’ll bet you be blowin’ her off. That why she pay so well?” Luke raised his hand and Miguel slapped it as they both laughed, then Luke held two spread fingers up under his mouth and flapped his tongue around, which brought on another round of laughter. “I heard she likes ’em young. See ya later sucka” Miguel called as he put the car in drive and pealed out as they continued to laugh. A moment later the booming bass began again as the car picked up speed down the road.

“Damn it,” Damon mumbled to himself, then turned and headed across the court to his bike. He climbed on and pedaled the short distance to his house, where he took a shower and put on fresh clothes, then headed back out. Mrs. Julia Ann Robinson lived about a half mile away and Damon was there in minutes. He leaned his bike against the front steps, then jogged up to the front door.

Damon didn’t knock anymore, instead he just opened the door and stepped into the entryway onto the small rug. Once inside, he kicked his shoes off, then reached down and removed his socks. Next he pulled his shirt over his head, carefully folded it and placed it on a low table to his left. He then unbuttoned his jeans and tugged them down, pulling first one leg free, then the other. Once again he carefully folded his jeans and placed them with his shirt on the table. Lastly, he removed his underwear, folded them and set them on top of his jeans.

Fully naked now, Damon got down on his hands and knees and began to crawl toward the doorway to the great room. He wondered what his friends would say if they could see him now, and shuddered at the thought of someone finding out what really went on when he was ‘at work’. He let his friends make their little jokes, smiling and rolling his eyes as if he would never even consider doing anything with Mrs. Robinson. She was older than his own mother after all, and nearly old enough to be his grandmother, so why would a good looking, charismatic guy like Damon be interested in someone so much older?

As Damon came crawling around the corner and into the great room, he could hear Mrs. Robinson talking. Thinking that there was someone else in the house, Damon froze, a shiver of fear traveling up his spine as he pictured himself being spotted. Then relief flooded in as he realized that she was only chatting on the phone. Once again he began to crawl toward her voice. As he came around the edge of the sofa, she glanced up and saw him.

“I’ve got to let you go Bree, my houseboy is finally here,” she said, staring at Damon as he crawled over to her feet. He hated being called her ‘houseboy’, but he didn’t complain. As he reached Julia’s legs, she lifted her stiletto heeled, thigh high leather boot clad left foot up in front of him.

“Oh yeah he is, he’s a young, handsome stud muffin,” Julia said to Bree, then, as Damon began to lower the zipper on the side of her boot, she added, “He’s got a really nice cock, you should come over sometime and I’ll let you try him out.” Damon shot her a surprised look as he began to tug at her boot. He had never heard her tell anyone about him before, and offering his services to an unknown person was going too far.

Damon started shaking his head as Julia continued. “Sure you can come over today, but not right away though, I want my time with him first. How about you come over at…say five o’clock, that gives me a few hours to have fun with him…Okay, I’ll see you then, bye.” She put the phone down picked up her wine glass.

“Who is Bree?” Damon asked as he finally was able to tug her first boot off and set it on the floor behind him.

“She’s a close friend of mine. Someone I trust to keep our little secret,” she said as she lifted her other foot.

“I never agreed to fuck anyone else,” Damon said, pulling the zipper of her boot all the way down.

“I know that dear, but I will pay you handsomely to show her a good time. How does double your usual fee sound?”

Damon tugged and twisted her boot gently until it slid free of her foot, then it joined the other behind him. “What does she look like?” he asked, ignoring for a moment the idea of making an extra two hundred dollars.

“She’s a sexy woman Damon, and younger than me by about ten years. She’s recently divorced, so she desperately needs something to get her mind off that drama. I think you’ll like her a lot.”

“I’ll decide when she gets here.”

Holding her stockinged foot in his hands, Damon pushed it against his face and began breathing in her scent. He could tell that she had been wearing her boots all day as the smell was strong and not very appealing, but even though the sharp odor caused him to wince, it still caused his cock to begin to swell. Damon hated that he had no control of his own body, and he was embarrassed by the fact that he did these kinky things with a woman ten years older than his own mother. That was why he kept telling himself that he only did it for the money, but he couldn’t deny the fact that he received pleasure also.

“Tell me how much you like the smell of my feet,” Julia said before taking another sip of wine.

“Mm, I love the smell of your feet Julia,” Damon said, not really meaning it, but this was the game that they played, the game that she wanted to play, and because she was the one with the cash, it had to be. The other foot came up and he held both to his face, breathing in the foul smell. His cock had reached its full hardness already, and he couldn’t tell if it was from smelling her stench, or the thought of fucking her.

“Take my stockings off, and show my feet some real love.”

Her stockings were thigh high, and Damon had to slide his hands up under her skirt to find the top. He could feel the heat of her pussy as he hooked his fingertips and began to pull them down off her smooth legs. He pulled one off then went back for the second one. When both stockings were off and bunched up on the floor, he placed both of her feet back on his face covering his nose. The stench was stronger, but his cock continued to throb harder, and he didn’t need to be told what to do next. Damon’s tongue slipped out and he began licking her wrinkled soles.

“Oh that’s wonderful boy. I’ve been on my feet all day in those boots and they really need some loving. Do a good job with them and I’ll reward you later.”

The inner battle that was going on in Damon’s mind was intense, but he continued to lave her soles with his tongue, licking from the rounded bottom to the top of her toes and back again. Inside he was cursing at himself for continuing with this relationship. He was angry with himself for passing up a chance to go swimming with Cara… and for what – a chance to make another hundred bucks being the plaything of a rich old widow?

“Oh, that’s wonderful, suck my toes.”

Damon moved up and took one of Julia’s big toes in his mouth. He sucked it like a baby sucks a thumb, his mouth already used to the sour, salty, bitter taste, while his mind was still a whirlwind of conflicting emotions. It wasn’t always this bad. Most days when he was with Julia, he would start out thinking about the cash he would receive, then get into the wild sex and enjoy himself. When he left her house he would often think about how lucky he was to get paid to have sex. Everything was changed on this day however, as he was now thinking about the fact that he blew his chance to hang out with Cara, and Cara was much prettier than Julia.

Not that Julia was a slouch either. In fact, for her age, she wasn’t all that bad. Sure her face was lined with some wrinkles, her skin was a bit leathery from years of too much sunlight, and her tits and ass were kind of saggy. Sure she had a bit of loose skin when she held up her arm, and her thighs jiggled when she rolled around on the bed. She was fifty years old after all, and although she did take care of her body, she showed some wear and tear like anybody. There was her belly scar that she said was from having her gall bladder removed, and the scar on her knee from knee replacement surgery.

But Damon overlooked all that because of the money, or so that’s what he had convinced himself anyway. His plan was to continue the relationship until he had a steady job that earned him enough money to live comfortably. For now though, he decided that he might as well have as much fun as possible.

While Julia sipped her wine and relaxed, Damon continued to worship her feet, working his way all around with his lips and tongue, sucking and licking away the tension and sweat. The whole foot worship thing was relatively new to him, and while at first it had struck him as silly and strange, he had since grown quite accustomed to it, and now his cock grew rock hard every time he started working on them. He wondered how it would feel to do this with Cara’s feet, but then realized that he would probably never try it because she would think he was a pervert if he did.

“Okay, that’s enough of that,” Julia said, pulling her feet away from Damon’s grasp. He hadn’t realized it but he had been playing with her feet for nearly twenty minutes. He watched her sit forward on the chair, a high backed Victorian style, and tug her skirt up her thighs. “My pussy is soaking these panties,” she said, spreading her creamy thighs wide open to showcase her sex. “See what you do to me boy.” With a look, Damon confirmed that she was telling the truth, as her white granny panties sported a large wet spot, rendering the material nearly transparent.

While Damon was looking at the wet spot in her underwear, Julia was looking down upon his cock still proudly erect. “I see that I’m doing the same to you,” she said with a grin, then lifted her foot and began to rub the underside of his manhood with her toes. A drop of clear pre-cum escaped from the tip and slid slowly down the helmet shaped head. She wiggled her toe into the smooth, lubricating liquid and spread it around the head while a moan escaped from Damon’s throat.

“Mm, I just love the look of your cock Damon. Such a beautiful thing. Stand up here so I can feel it,” the older lady said. Damon complied and she took his member into her hands. This was unusual but Damon wasn’t going to complain. Normally she made him get her off at least one time before allowing him the privilege to cum.

“My husband never let me touch his cock you know, he said it was a sin. Hell, I never even saw him naked in all the years that we were married. He would come to bed in full pajamas after changing in the bathroom with the door locked. Can you imagine that?”

Damon was having a hard time imagining anything as his cock was being manipulated, but he did what he thought was polite and nodded his head.

The older woman continued, “Twenty four years I spent with him, and the only time he ever touched my pussy was when he was trying to fuck me. I always knew when he wanted sex because he would climb under the covers, then pull his pajama bottoms off. Then he would climb over me and start humping away like a dog. I was just glad that his cock was so small because I was almost never wet when he started, and he always finished so quickly that I never got any satisfaction. He would tell me that sex was for procreation only, but the limp prick never did get me pregnant.” She laughed as her hands slowly stroked. She had both hands wrapped around it and the head was still sticking out.

Struggling to maintain his composure while his cock was being expertly stroked, Damon balled his hands into fists and cried out, “Oh shhhhit I’m so close.”
“Really, are you going to cum for me Damon?”

“Mm hm,” he whined as another dollop of clear fluid dripped down the head of his cock and smeared onto Julia’s fingers.

“Then cum boy,” the older woman replied, jerking away at his cock. She could feel it twitching and jumping in her hand and knew that it would soon spurt.
Damon’s legs were wobbling as if they were about to give out. His balls were churning as they prepared to empty their seed. A drop of sweat rolled down the side of his face but went unnoticed as the need to cum built to a crescendo and then…”Oh yeah, I’m cumming,” he cried out as he reached the pinnacle and was pushed past the point of no return.

Watching his face closely, Julia encircled the base of Damon’s cock with her fingers…