tagMatureMr. Nice Guy vs. The Concert Milf

Mr. Nice Guy vs. The Concert Milf

byEsotericNiceGuy©

Summer was coming to a close, and Jason was about to start his final year of high school. All his life he had let his neurotic over-analytical nature control how he interacted with people. He had always put too much thought into everything, and as such had wasted his childhood. He believed he was unpopular, and therefore he was. With the social experience he had gained over the summer however: after having turned 18, going to parties, and fucking a busty young mall rat senseless, Jason was ready to improve his social standing. Life was finally a game he was ready to play.

But his senior year of high school had not started yet. Amy, his younger step-sister, REALLY wanted to go to a concert in the park, adjacent to college campus. It took some convincing, since Jason had zero interest in the boy band that was playing, but there would likely be a ton of girls there, he didn't have anything better to do, and he might as well try to get along with his newish step-sister and her friends.

Jason was not the only chaperon for the group of girls, but he was the only male one. The other three were moms, and two of them were kind of attractive, although only one of them was a MILF, per say. Her name was Melanie, and she was this smoking hot woman in her early forties. The kind of woman Jason had downloaded plenty of pictures of. Tall, thin, and busty as hell. She was built like someone who could handle herself in a fight, and clearly had a dominant personality. She was Becky's mom. Donna came in second on looks. She looked like a regular housewife, roughly around the age of 35. She had wider hips, a nice chest, and a little bit of an ass, but she wasn't chubby by any means. The last of the women, Hylan, was kind of on the large side. Not that Jason was above overweight women, beggars cant be choosers, but she just wasn't specifically an attractive woman by any means. Not in a fuckable way.

He had been ready to loose his virginity since birth, and now that he had he was ready for more. As the girls ran this way and that, He and the three moms sat towards the back of the roped off area. He spoke with them as equals, and they treated him as such.

The two of the women, Hylan and Donna, were flirting to tease him, Jason soon figured out. The more attractive of the three wasn't flirting specifically, but she was certainly friendly enough.. They had to know that he was only in high school, so they had to know that he was only 18. Still, he enjoyed all of the casual touching that went on while they spoke. They had arrived before Jason had, and had already had a couple of drinks. It wasn't too long before Jason was able to take a few sips for himself, and not too much longer before they offered to buy him his own.

Things went so well that Donna actually offered him a job. She was a manager of a grocery store, as it turned out. They exchanged numbers.

Still, it became apparent as the second band took the stage that the women were just flirting for the sake of flirting, and he didn't have any real shot of hooking up. At least not that night. Jason grabbed his third beer and told them he was going to "make his rounds". He got up and wondered the crowd looking for a potential hook up.

Jason saw several people from his high school, mostly girls, and he spent a few minutes talking to each.. The year before he would have kept his head down and not spoken to anyone.

At one point Jason even spent a little time hanging out with the step-sister and her bubbly friends, who were all impressed that he was milking a beer.

As the final band hit the stage, Jason gave up on picking up a one night stand. Several women were giving him a glance or two, but everyone was here with groups of people, and Jason lacked the experience to pull off picking a woman up when she is being guarded by her friends.

Giving up, Jason found a fairly vacant spot on the ground and took a seat on the damp grass. He was fairly new to drinking, and it was affecting him more than he would like to admit. He sat in silence for a while, nursing his beer. Suddenly, a pleasantly feminine voice said "You look like you are having a good night tonight."

Jason turned around and laid eyes on a very sexy looking raven haired woman in a silk shirt, short skirt combo. She might have been in her mid forties, and wore a lot of jewelry, silver and diamonds. Her shoes and purse alone probably cost more than Jason's jeep. But that was not the first thing Jason noticed about her. Or the second. The first thing he noticed were her long, toned and tanned legs. Her skirt was short and she sat in a reclining lawn chair, her long legs extending down towards where he sat on the grass. Jason was instantly sold on whatever she was selling.

"I am." he agreed, although she could have said 'Some tornado we are having right?' and he would have agreed. What he really heard was replaced with 'Hi, I am hot, wanna play the flirting game with me?' Thinking about what she had actually asked he asked, "How could you tell."

"The beer, the fact I have not seen you without one, and I've watched you talking to about 20 something people tonight," She smiled, and Jason liked her smile. He WAS a little buzzed, he decided, although in it was really only his third beer still, she just didn't realize he was nursing the same beer all night. "I specifically spotted you talking to a couple of cougars earlier."

Cougars? Oh, she meant Donna, Hylan and Melanie.

Why hadn't Jason noticed her before? He looked at the two black empty lawn chairs to her right and realized that he had, but she was here with two other attractive women so he wrote them off. He was not yet confidant enough to walk up to three hotties and introduce himself without looking like a nerd. Plus all three had been wearing big diamond wedding rings. This girls rock was pretty intimidating. She was alone now though. No husband, no girlfriends, no one to try and scare Jason off.

Come to think of it, the other two were here when he sat down just a second before. "Where did your friends go?" He asked, nodding to the empty chairs.

"Refill." She lifted an empty cup and sat it back on the grass. It was a one word answer, but somehow she made the simple, short answer seem sexy. "I take it you struck out?" she asked, raising a teasing eyebrow.

He smiled as he thought about how to answer. He didn't want to make her sound like a last resort. Although anyone you go home with is your last resort. You have to stop trying when you actually go home with someone. "What makes you think I took a swing?"

"You talked to quite a few girls not to be trying for something." she countered.

Jason used the effects of alcohol as the excuse to stall for an answer. He squinted and tilted his head as he thought of a response, as if a bit dizzy. "I have a lot of female friends." He winked at her.

"I bet you do." She tilted her head thoughtfully. "So why not take home any of your pretty friends? Not in the mood?" She smiled and shifted slightly in her seat. Her legs were crossed, but she lifted one slightly in the shift exposing more of her thigh. Jason noticed, and this stranger noticed that he noticed and smiled a little brighter. For some reason he had developed a slightly southern accent when he spoke to her, and he had planned on only sounding inebriated. She seemed to buy it.

He looked away from her for a second and sipped his beer, then turned to her, gesturing to the other concert goers. "Those cougars were just parents of my sister's friends. I was just flirting with them for fun. I am not interested in actually doing anything with older women who know my family."

He looked away from her smiling. He kept his eyes on the stage as if distracted

After a few seconds of silence, her sexy voice asked "And what about with a stranger?"

Jason sighed and turned to her. He let his eyes slide up her long legs, her slim waist, her chest, her sexy lips, and her enchanting eyes. He held her gaze for a few seconds before whispering in his best husky voice. "I would want to do the kinds of things that your husband would not approve of and your two friends would never allow."

She laughed at him. Loudly. Damn it. He looked away from her. He had blown it, and his cheeks burned red from her laughter. He was mad at himself for trying to sound sexy too. He was about to get up and retreat when she managed to say "Hey.... Hey!" Through her laughter. Jason turned to look at her, squinting defensively. She didn't notice. "You would be surprised what my friends would let me do tonight, and I don't give a damn about what my husband would approve of. He sleeps around on me just as often as I have my... fun." Jason raised his eyebrows. 'Who would cheat on a hottie like this?' he thought. She calmed her laughter and looked at him directly, the sexual tension returning to her voice as she asked "Would you care to rub my shoulders?" She offered him a fake pout and pushed her chest forward, as if he needed the additional bait.

Jason was startled that things were progressing so quickly, and was off his game when he answered "Yes I would love to." 'Crap,' he thought, 'should I have answered so quickly?'

"How old are you?" she asked formally.

Jason paused before deciding to lie. "24."

She smiled, looking at him suspiciously. He took too long to answer, he realized. Jason looked old for his real age of 18, but maybe 24 was pushing it. He decided to cut her off before she asked him to see his ID or something. He held up his beer as proof of his age. "I get that I look 20 a lot, but I am well over 21." He smiled confidently, and held her gaze. He could see when she accepted his answer.

"My name is Connie. What is your name?" she continued.

"Jason."

"Well Jason, I am thinking about renting a hotel with you, but I am undecided, and it is not time to leave yet, so you have time to convince me if you want to. Sound like a deal?"

Was getting laid really so easy? Or was she a tease too?

"Deal!" he replied, after pretending to think about it for a minute.

As he stood up from his chair Connie scooted forward in hers, so that Jason could straddle the chair behind her. Jason was rock hard when he stood, and it pitched his jeans in a remarkably obvious way. Connie smiled at his bulge and said "Ten points in your favor big boy." and before winking at him.

Jason sat down behind her, and she immediately scooted her tight little ass back against his aching cock, and before he had even placed his hands on her shoulders her hand snaked back to give his cock a cursory feel. She then nestled her ass more firmly against him and pulled her hair away from her shoulders, so that he could get started. More confident than he might have been otherwise, Jason went ahead and got to work.

Jason had never been taught how to give massages, but this was hardly his first time. He started out by feeling out her bone structure. In his mind, he tried to picture how her muscles would be holding it all together. Looking at her back, he tried to get an idea which of her muscles she uses most often, what would be most tense, what would need pressure and what would need a soothing rub. Essentially, he put way too much thought into what he was doing, like he always did.

It paid off though. Despite her cavalier demeanor, Connie had been tense making the first move. Jason's probing fingers found that tension swiftly and began working the stress back out of her. He didn't focus on any area above all others, he deliberately took the time to make sure the entirety of her back felt worked on. He preferred to have his hands on her skin when he could, but the silk shirt didn't hinder his efforts too greatly. Connie seemed to melt under his probing hands, her head lulled back and forth. Jason was having much more fun than she was. A year ago, he would have never imagined actually having his hands on an older babe like this. Assuming she took him home with her, and all signs were pointing to yes, she would likely be the hottest piece of ass Jason would have in quite some time.

As Jason's confidence and erection grew, Jason's hands began to wonder. They would start towards the center of her back and work their way slowly up to her neck, down to her shoulders, only on the inside her collar, his fingers would slide an inch or two towards her chest, then slowly back to her shoulders, then down her back to firmly squeeze her ass, then back to her hips, up her sides until they almost reached her breasts again before circling back to the center of her back to start the cycle over again.

Jason completely lost track of time. She finally leaned her body back against his and sighed. Her hand again snaked between them and gripped his ever growing rod. It was noticeably bigger than the last time she touched it. "I am definitely going to need this in me tonight." she confided in him.

'SCORE!' He thought as he continued to work her arms and shoulders. His hands worked their way up her arms to her shoulders, then to her neck, back down her arms to her hips, across her short skirt until they just barely touched her bare thighs, then back up to her hips, up her sides, under her arms this time, inches from her chest....

"Hey Connie, who's the stud you got feeling you up?" A female voice asked from out of nowhere, waking Connie and Jason from their trance.

"Jamie, Beth, this is...." Connie forgot his name....

"Jason." Jason offered.

"... Jason." Connie agreed "We were thinking about leaving the concert early. Would you be mad if my friend Jason and I took off?"

"Jealous!" The two women chimed in. Jason, for one fleeting moment, thought this might lead to a foursome, but the two other women wished them luck, and told Connie not to do anything they wouldn't do. This brought on a round of laughter.

Soon Jason and Connie, an older married woman, were arm in arm making their way across the parking lot to her SUV. He was nervous, not just about sleeping with an older woman, but about ditching the concert. He WAS supposed to be a chaperon, after all.

Connie started whispering about how badly she needed to be fucked into Jason's ear, and suddenly he was not quite as nervous anymore. "I really need your cock young inside me. Would you mind driving? I simply can't wait to get my lips wrapped around that big steel hard pole of yours..."

Jason, always the gentleman, agreed to drive. He opened the car door for her as she got in. He couldn't take his eyes off of her legs. He slid his hand across them. Naturally, he took a moment to slide his hand up her skirt and rub her wet little pussy. He was shocked to find she was not wearing panties in a skirt so small. But then again, considering how quickly things were moving, he probably should not have been.

"Drive us to a hotel?" She encouraged him.

He resisted the urge to slide a finger inside of her. Instead, he shut the big white door. Circling the SUV, he hopped inside.

As soon as the SUV started forward, Connie's hands were on his jeans unhooking the buckle. She had his cock fished out in no time, and sight of the big diamond ring gave Jason a sexy taboo feeling as the hand it was on wrapped around his thick cock.

"God you have a beautiful cock!" was all she said before it disappeared between her ruby red lips.

He had only had one blow job before, and that was only a week ago. This one was better. Where the mall rat had had a shy enthusiasm, Connie knew exactly what she was doing. It was like comparing a middle school basket ball player to a Harlem Globe Trotter. Jason felt himslef growing longer and harder in her throat. Somehow her throat muscles bent his cock down her throat and squeezed it as it moved in and out.

Jason did not think he could ever cum from a blow job, but he definitely considered the possibility as he drove to the closest hotel he knew of. She didn't stop until the car was in park.

She sat up with a big drunken smile. "Goody!" she said as she opened her own door and slid out, before he could get out himself. She fell against the adjacent car, where she remained until Jason circled the vehicle and righted her. He thought to himself, "Am I being seduced or am I taking advantage of a drunk?"

"Do I care?" he answered himself.

He was surprised that she insisted on paying. She paid with a card. Jason was amused as he realized that meant the husband was likely actually paying for the room. The guy behind the counter asked if two beds were needed, looking pointedly at Jason. Thoughtfully, Connie looked back to her new boytoy. "No thanks, if we need the extra room he can just fuck me on the floor." She looked back at his shocked expression with a smirk and grabbed the hotel key.

She liked the feel of Jason's arm around her as he walked her to the elevator, and had to resist the urge to pull him out and blow him once the elevator started moving. She loved elevator sex, but did not want to risk getting kicked out before she got what was cumming for her.

They made it to the hotel room.

She unlocked the door.

She was surprised when... what was his name? Pushed her inside and against the wall, dropping to his knees in front of her. His hands slid quickly up her legs, hiking up her skirt, and no sooner was her pussy exposed than he sunk his tongue deep into her pussy, his hands squeezing her bare ass as he pulled her against him. Sex with younger men was so exciting! "Thats it kid, fucking eat me like a good little boy!" She said as she pulled his hair. He was good at this! He licked her, bit her, sucked on her labia. She lifted her legs onto his back, so that she was sitting hon his shoulders with her back against the wall. "You don't get to stand until you make me cum!"

Jason hooked his thumbs under her to help hold her up, which put his thumbs right by the entrance to her pussy. He teased her with his thumbs, making her body wonder if one would slip inside. Jason loved the way she pulled his hair and the way her smooth perfect thighs felt against his face. She started making noises that she was coming, so he pushed both thumbs into her as he sucked on her clit, held it in place with his teeth and raked his tongue across it vigorously. "Fuck!" she screamed. Jason was certain the people in adjacent rooms knew someone was getting laid now.

Jason had his cock out in an instant, and as he stood he held her against the wall, her body sliding down his. When her pussy came in contact with his cock she cooed, ready to take it however he wanted to give it. Instead of fucking her against the wall, he carried her further into the room and threw her down on the bed. He grabbed her hair and pulled her forward into a sitting position then lifted her head so that she looked at him. She was definitely in her late thirties, early forties. Probably older than his step-mom. This thought made him laugh.

"I want you to get me good and wet before I fuck you." he ordered her, and with that he pushed her head down onto his eagerly waiting cock.

"Bossy!" she thought to herself as she obediently took the gorgeous, large cock back into her mouth. "Of course, with a cock like this you can afford to be." He let go of her head as she proved that she was more than willing to obey.

She was just getting a good rhythm down when he shoved her back on the bed.

He had taken his shirt off and stepped out of his pants, and he was not bad to look at....

He lifted her legs straight up in the air and leaned against them, rubbing his now wet cock against her pussy. He pushed his head in, just his head, before letting go of his cock and rubbing her smooth legs with his hands. "Little boys always have loved my legs." she had time to tease before his hands gripped her hips and his cock slammed all the way inside of her. She grunted in a very unlady like way. "He was way too big to go slamming into people like that!" She wanted to tell him, but then he slammed into her again, and again, and the idea of forming a sentence suddenly seemed unlikely!

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