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Jessie and the Cougar

Category: Mature
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Jessie was running a little short on cash for the next year of college, his mom and dad helped him out a lot but they thought that he should earn his own spending money, doing odd jobs around town, mowing lawns raking leaves and so on. What he really had his heart set on though, was a car.

“We are going to get you a nice new car when you graduate son.” His father told him, when he asked to borrow some money.

“What about until then dad?” Jessie asked.

“Well if you want a car you are going to have to buy one yourself. I’ll help you fix it up and put you on our insurance, but I won’t buy it for you, that you have to do yourself.” His dad replied.

Jessie was a little bummed. He had already saved up $750.00 but needed that for school, he was already a month into his summer and new he wouldn’t be able to make it up plus get the extra he needed for gas.

Then he spotted the ad:

“Help Wanted-Evening Delivery Driver.

Will pay gas and $1.00/mile plus $5.00/hour wage.

Wong’s Wings”

Jessie was ecstatic. He could buy a car with his money, do the work he was doing during the day and make money off the car at night. I would only take 125 hours to make the money back. He could easily do that over the rest of the summer. He went home with the ad and talked to his dad.

“All right son, you got me. Lets go see what we can find.” Jessie and his dad went down to a used car lot. The owner Mr. Brady was a good friend of his fathers.

“What can I get Jessie here for $750 and in good enough shape for a delivery car?” Jessie’s dad asked. Mr. Brady took them around to the back. There was a row of old cars parked there, some in pretty bad shape.

“These are my ‘special models’.” Mr. Brady laughed. “I just had a push pull or drag sale, basically I gave them at least $1000 for anything they could get in here towards a new car. These ‘jems’ are heading off to the scrap heap, but I’ll tell you what, grab Herb, our mechanic, and you guys go over any car that you fancy there, if Herb figures it’s reliable, you can have it for $500, save me the trouble of having it hauled away.”

“Thank you very much Mr. Brady.” Jessie said, his day was getting better already. He had his eyes on an old Datsun Z. It had a little rust but looked okay. Herb had a look at it, put some new spark plugs in cleaned some stuff up then hooked his tow truck battery up to it and gave it a boost. A few pumps of the gas pedal and she fired right up.

“Looks like someone got duped.” Herb laughed. “This car is in great shape. Runs like a top, would have been able to get a couple grand for it, your lucky I didn’t see it first. Well go give Brady your money kid.”

“Thanks Herb.” Jessie said and went into the office.

“Find one Jessie?” Mr. Brady asked. Jessie told him the one, Mr. Brady nodded knowingly then wrote up a bill of sale.

Jessie and his dad drove the car down to get insurance and plates and when they were done he went to Wong’s Wings and asked about the job. Mr. Wong was very impressed with Jessie and his car.

“That is a very good car, I used to have one just like that, only new. Good car indeed!” The restaurant owner told Jessie he could start the next night.

Jessie was working hard. He had given up a few of his regular customers during the day, but more than made up for the loss of money at night. He did very well with tips, of course his big smile and friendly demeanor helped a lot. Between tips and his wage, he was bringing in about $60 a night.

It was Wednesday night, 10 o’clock. He was making his last delivery, then was going straight home. It was cool and rainy so there were more deliveries than usual. He pulled up to 227 Hamstead Heath Cir. A big house with a looped driveway, covered with a pillared entranceway. Jessie parked under the canopy, happy for a dry delivery for once. He turned off his car and grabbed the package off of the passenger seat, General Tso’s Chicken and a six-pack of Miller Lite, which he picked up along the way, special orders. He rang the bell and waited.

A light came on in the window beside the door. “Who is it?” A breathy voice asked.

“Wong’s Wings ma’am, delivery.” Jessie replied.

“Just give me a moment dear.” The lady said, “I’m not decent.” A minute later, the door opened.

The lady was in her late thirties or early forties even, it was hard for Jessie to tell. She was wearing a black negligee with a matching robe, barely covering her trim fit body, her large breasts were nearly spilling over the top barely restrained by the soft shapeless structure. “Come in close the door, don’t let a chill in.” She said. Jessie had a hard time listening to her; he was watching her nipples poke through the fabric of her lingerie from the cold blowing in through the door. He closed it behind him and waited. She took the food and went into the kitchen. “How much do I owe you?” She asked, digging into her purse.

“$19.68 ma’am.” Jessie stammered, he could see her breasts clearly down her teddy as she bent over (needlessly) to look in her purse. Jessie was wondering if she was trying to seduce him.

“I’m sorry, what was your name?” She asked, Jessie told her, “Jessie, I’m sorry but I only have a twenty; I don’t have anything for a tip.” She looked at him sadly.

“That’s ok ma’am, next time.” Jessie said, took the money and reached for the door.

“No, no I insist on giving you something. Do you have to go back to the restaurant?” She asked.

“No, not tonight, why?” He asked. His heart was racing a little bit. He knew this lady; she was am acquaintance of his mothers, Mrs. Ingles or something. It was all coming back to him now. Mr. Ingles, the owner of the Golf and Country Club and Mrs. Ingles head chair of the Downtown Beautification Committee his mother sat on. This was too weird for him. He decided maybe he better just book on out of there. “Listen I really have to go Mrs. Ingles.”

“Oh call me Mercedes.” She walked up to Jessie, holding out her hand. Jessie took it then she pulled him in to her, and kissed him.

“Mrs. Ingles… Mercedes!” Jessie exclaimed. “What about Mr. Ingles? I can’t… you can’t… I mean we can’t…” Jessie raced for the door but Mercedes got there first and spread her body in front of it.

“Fuck Mr. Ingles, he’s banging his secretary right now, he told me he was, ‘Mercedes,’ he said, “I’m going to the office to fuck my secretary, I won’t be back until after you’ve gone to bed.’ If he can fuck his secretary why can’t I fuck my delivery boy?”

“Umm because your delivery boy doesn’t want to get fucked right now.” Jessie smiled nervously. Mercedes shook her head.

“How old are you?” She asked.

“Nineteen.” He replied.

“What nineteen year old boy does not want to get fucked? Fuck while you can because when you turn fifty all you want to do is work.” She said.

“Well your husband likes to fuck his secretary.” Jessie said then realized how dumb he sounded.

“Probably, I just made that up, actually he’s away on a business trip, Cancun, Acapulco, Albuquerque some fucking place down south. Do you want a drink?” She asked and walked away from the door, “or are you going to run away on me? Maybe we could just talk, it gets damn lonely in this big old house all by one’s self.”

“Sure, I’ll have a beer.” He called to her as she pulled her gown back up over her shoulders and walked into her husbands den.

“Scotch that was?” She walked back swirling the ice around in the glass handing it to Jessie. She had a two olive martini herself.

“Actually it was… never mind.” He took a small sip and tried his best not to wince at the bitterness. Mercedes sat back and laughed. Jessie just sat there, contemplating his drink and how best to finish it, then get out the door.

“Do I look old to you?” Mercedes asked, taking a big sip from her martini glass. “I mean, to you I look old but what I mean is if you saw me on the street how old do you think I was?”

“I don’t know, twenty-five?” Jessie said, rather honestly. “Maybe thirty, somewhere in there.”

“Well I’m fucking forty-four, can you believe that?” Jessie was shocked. “I have worked my ass off everyday, two hours of aerobics every morning, weights five days a week, tai-bow. I swim ten miles a week. Do you think he notices? Never that fucker openly ogles every young think that walks by, but he won’t even touch me.”

“I think you’re very beautiful.” Jessie said, not knowing what to say. “He doesn’t know what he is missing.”

“Thank you, you’re too sweet.” She said. Then she stood up. “Tell me honestly, what is wrong with this?” her negligee and robe fell to the floor leaving her standing there completely naked. Her body was not forty-four. Jessie looked her up and down awe-struck. The little girls he had been banging in college where nothing compared to this, she was all woman. Her calves were shapely and toned. She had strong thighs, rounding in, making a nest for her neat and well trimmed pubic. Her stomach was flat and hard. She stood with her hands on her hips, pushing her chest out. “I had these done, for him, I don’t think he even noticed.” She pushed up her large firm breast, “he did a great job, feels real, want to feel?”

“I really shouldn’t,” Jessie said. He was curious though, he had never felt a fake tit before, seen lots of them in strip clubs and in pornos, but never actually touched one.

“Come here, I won’t bite, just touch it, tell me if it feels real, you have held a breast before, you do have something to compare it with?” She walked over to him and took his hand. She moved it up her stomach to her breast. He squeezed in and felt it’s firm fleshiness.

“Yeah, it feels real.” He was having trouble stifling the growing hard on in his pants. Had he been wearing jeans it would have been easier, but in his gray work slacks he was having much more difficulty. “Listen I really need to get going Mercedes, my parents are expecting me…”

“No they aren’t they are at the same silly party my husband is at.” She cut him off and blocked his exit from the chair.

“I thought you said he was away.” He asked trying desperately to get away.

“What can I say, I lied, I don’t really care where he is.” Jessie pushed himself up in the chair, sliding up the back hoping to get over the back and out the door, however his erection caught him.

“What’s this?” the older lady asked, taking a handful of his erection through his pants. “Oh my you’ve got a lot down there for such a young man.” She pushed him back down in the chair by his cock. She stroked his cock through his pants and pulled his hand up to her tit again, locking their hands together as she rubbed and squeezed her breasts. Jessie tried to make a break for it again when she let go. This time he managed to get over the chair, but she dove over after him and knocked him to the floor, her naked body on top of him.

“I like a man who plays hard to get.” She said and kissed him on the mouth and at the same time pinning his arms to his side. The carpet in the room was soft and smooth, not the kind of carpet to give you a case of rug burn. “I could teach you so much, just lay here and let me teach you.”

“Fuck it,” Jessie said, “I don’t have a choice really, and besides, damn you have got to be the sexiest woman I have ever seen.”

“Now that’s more like it.” She kept his hands pinned and kissed his neck, biting lightly and sucking, then she moved to his earlobe, nibbling on it and blowing gently. His cock hardened inside his pants as he felt her heat on top of it. She ran her naked body over his, her wetness penetrating his pants while her pussy tried to gobble in his erection through his trousers.

She sat up astride him, sitting directly on his crotch. She was heavily aroused, he could smell the sweetness of her ripe pussy wafting up. Her breasts were begging to be rubbed, kissed, fondled; her nipples, hard and erect, needed sucking. Her reached up with both hands and began to fondle her firm large orbs. She pushed her hands up under his shirt, raising it up.

“It’s been to long since I have been with a real sexual creature.” She said as she ran her hands up his thin but toned torso. He sat up so she could get his shirt off; she pulled it up over his head then pulled him into her chest. His nose smelt the odour of sweat and expensive perfume between her bosoms, he lapped it up. He ran his tongue up the length of her cleavage, around the top then down, taking turns licking kissing and gently sucking.

Mercedes let out a weak moan as he too her nipple in his mouth, biting it gently then sucking it and flicking it with his tongue and pushing it out. She moved back off his pelvis and undid his pants. She pooped the button and undid the zipper. His cock had already made it’s way out of the fly of his boxers. When she touched it he was afraid that it would explode right then, but it didn’t.

“Are all you young men like this? I haven’t seen a cock this big let alone ride it.” She was just flattering him of course. He had never had any complaints about it, but seven and a half inches isn’t anything to go to Guinness about. “It’s so big and so hard.” She said. Mercedes pushed the foreskin down of the head and ran her thumb over the top, making circles over it, then closed her fingers around it gently stoking the head.

Mercedes moved her other hand down to his balls, grabbing them in her hand and squeezing them. She ran her other hand up and down his cock, stroking it slowly but holding it firm. Her thumb grazed over the tip as she reached the top.

Jessie was having a hard time concentrating while his cock was getting stroked, he just wrapped his arms around Mercedes back and held his face to her breast, moaning softly. She moved further back and he let go of her. She bent over and kissed his neck, then ran her tongue down it. His nipples were hard. She licked them tenderly then bit them hard, only to use her tongue to ease the erotic pain. His cock was sandwiched between his body and hers. The thick precum holding them together like glue. Mercedes slipped down further, running her tongue down his chest to his stomach. She playfully tickled his belly button with it. He flinched with anticipation. Her lips kissed it’s way down the rest of his belly. She then ran her tongue along the sensitive area between his cock and thigh, teasing it, blowing into it and letting the air eddy around his arousal. She moved to the other side, playfully teasing his balls with her lips on her way by.

Jessie put his hands on her head, playing with her soft long hair. She looked up at him, a look of hunger in her eyes as she took his cock in her hands once again. His back arched with anticipation. Mercedes ran her tongue over the tip of his cock, lapping up the sweet juice glistening on the tip. She licked all around the sensitive head of his uncircumcised manhood, making him squirm on the plush carpet. She moved her tongue further down his shaft as she opened her mouth to accept him; her moist upper lip grazing his head. She pulled her tongue in and closed her mouth around his cock, taking in just the head, letting the rim that separates it from the shaft hold it in place. Her tongue ran in circles inside her mouth. His cock throbbed as she gently bit down. She turned her head sideways and ran her lips along the out side of his shaft, flicking it with her tongue all the way down. When she got to the bottom, she took his sack in her mouth, juggling his balls with her tongue while stroking his pulsating cock with her hand. She then moved back up his shaft again and took the tip in her mouth. He pushed her head down slowly forcing more of his cock in her mouth. She accepted it and sucked hard as more and more went in. He felt his tender head hit the back of her throat, she swallowed hard causing a ripple to run through him, then she took in the rest, deep-throating him. She brought her head up again, still sucking, leaving a vacuum in her mouth as she moved back up his shaft, she reached the tip let it out of her mouth with a pop, the let it back in again.

“Guide me, make me fuck you hard.” She said looking up at him, then stuck her mouth around his cock again. He took her head in his hands slowly sliding it up and down his cock, then speeding up, she kept constant suction on it while her mouth took it all in. Her tongue slithered inside her mouth liking the shaft, her hand squeezed his balls. He moved her head harder and faster, he could feel the cum in his balls building, he was shaking.

“Let me taste you, let me drink you cum.” She said, longingly, breathlessly. He felt the cum well up.

“I’m cumming, I’m cumming.” He said between breaths of ecstasy. He tried holding back, prolonging the pleasure, but couldn’t, he felt the river reach the tip of his cock and explode out the end. Mercedes sucked in the juices hard, the first forceful shot hit the roof of her mouth, the second and third she caught with her tongue. Each contraction of his cock brought another spray of his juice. Mercedes took it all greedily, she sucked on the tip, trying to get every drop out of him, squeezing his balls to be sure he was empty. When she was sure there was no more to be had she moved up and kissed him.

“Oh my god that was phenomenal!” Jessie said holding her body on his.

“What, you think I’m done with you? What about me?” Mercedes moved his hand down to her moist crotch, pulling it along the length of it. “You’re a young man, I bet you could be ready to go again in a few minutes with a little coaxing, and besides…” she pushed his finger inside of her… “don’t you want to feel what’s in here?”

The thought of it made his flaccid penis grow a little, she felt warm soft and wet. He kept pushing his finger into her soft cave, exploring it, wiggling around inside then pulling out. She moaned with each exploration, the rolled off of him and lay on her back. “I want to taste me on your lips.” She said and pushed his head down to her nether regions. He flattened himself on the floor between her legs. He extended his tongue and ran it up the length of her pussy, parting her lips with it, using the tip to catch the droplets of sweat. He could feel blood already starting to flow back into his cock as he flicked his tongue over her clit.

She rolled from side to side on the carpet and moaned loudly, her hands running through his short hair and he licked her twat gently and forcefully. Darting his tongue over her clit, toying with it, then running it down to her love hole, darting it in and out. He moved his hands up, spreading her legs further apart. His nose rubbing her clit while he concentrated on her inner sanctity with his tongue, then he moved his head out of the way, so he could finger her surprisingly tight hole. She shuttered and whimpered with the dual action of tongue and finger worker her into a frenzy.

The sweet smell of her cunt and taste of her cum on his lips brought the blood back into his cock. It was almost completely erect under him. Her pushing his head hard into her groin only intensified his re-born arousal. She reached forward and dug her nails into his back as she screamed. “Oh fuck yes, fuck yes, OH GOD! I need you inside me right fucking NOW!” She put her arms under his and pulled him up to her. He let his newly hardened cock run along the inside of her thigh, he held it taunt as he moved it between her legs. He felt her wet labia on the tip and let it drop a little. He dropped his pelvis on top of hers and his cock fell below the hole. She pulled him to her lips, the taste of her cum still in his mouth, she was licking it out when he tensed up his cock and slid it easily into her eagerly awaiting pussy. The inside was smooth and well lubricated; no resistance to his penetrating cock. She let out a sigh as it hit it’s deepest level. He left it there for a moment. He pulsed it while she used her inner muscles to squeeze around it. Then as she squeezed he slowly wriggled it out. He was laying completely on top of her. She was taking shallow breaths, almost hyperventilating. He kissed the nape of her neck while he slowly penetrated her again, then he pushed himself up on he hands, giving himself extra leverage. He pulled his cock out as far as it would go then dropped his body into hers, using all the power he could get, trying to get as much of his manhood inside of her as she could take. He pulled out again, then pushed back in faster this time, beginning to get a slow rhythm.

“I like it hard,” she said through her teeth, “yeah, like that, fuck me hard my young stud.” He complied by picking up the pace, his rhythm got harder and faster. The sound of their bodies hitting went from adagio to disperato, from graceful to reckless abandon. Sweat formed on his brow and glistened on her chest. Her breathing became more erratic as her orgasm intensified. He could feel her insides moan and quiver, then she let out a scream and arched her back high off the floor, pounding her hands down, then relaxing. He felt a flow of warm juices flow down his cock, and then dribbling down his balls. Mercedes dug her nails hard into his back while the onset of a second orgasm came. His was coming too. His arms shook as he put all his energy into trying to hold back his orgasm. The trembling started again. His balls ached as they released the second cuming, as it welled up, he collapsed on top of Mercedes. His cum shot deep inside her, she convulsed as his cum filled her insides. He laid on top of her, them both breathing heavily after the exertion of pleasure and ecstasy took their toll. Sweat still covering both of their bodies.

She had not been fucked like that for many years, she missed the enthusiasm of youth. He had never been fucked like that. Her power of him was overwhelming, he wanted nothing more than to be with her again and again.

“Can I see you again Mercedes?” He asked while laying in her arms looking at her cloudy blue eyes.

“Ummm, I think so, I have not even begun to teach you all you need to know about pleasuring a woman.” She took his hand in hers and ran it down to the soft hair of her pubic, then moved his fingers over her soft warm pussy, making him touch her where she felt it most.

Jessie had to phone home and leave a message he was staying at a friends place, then hide his car down the street. Mr. Ingles as it turned out slept in the guesthouse. Jessie took lessons from Mercedes most of the night, he gave up all his day time clients to concentrate on The Ingles “gardening” but still delivered for Mr. Wong at night. That was the best summer of Jessie’s life.

That year at college, he gained a reputation as a real lover, woman were knocking down his door for a chance to be with him. Yes it was a very good summer indeed.

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