Of Mothers and Milfs Pt. 01

I started writing this story with the intention of making it a fairly simple and light-hearted tale of two sons and two mothers. But the characters had minds of their own and one of them asked a question early on that made the story much more challenging to write, and much longer. I'm glad he did though—it resulted in a much better story and more importantly, gave me new insight into the kind of stories I wanted to write.

The story builds in a long, slow burn, but I trust you'll find the conclusion, and the story itself, worth the while. I hope you enjoy it.

All sexually active characters are eighteen or older.

* * * * *

Of Mothers and MILFs Part 1

Only the united beat of sex and heart together can create ecstasy

Anaïs Nin, The Diary of Anaïs Nin, Vol. III

Emily Maye and Amy Deming sat in the bleachers of the Euglena Valley High School baseball field watching the final game of the season. They watched as Amy's son Charlie stepped into the batter's box. Walt Maye looked up from the Science News magazine he had been engrossed in for most of the game.

Walt had been Charlie's best friend since they met when he and Emily moved to Euglena Valley four years ago, after Emily's divorce. Emily and Amy met through the boy's friendship and quickly developed a friendship of their own. Amy too had gone through a wrenching divorce. With all this in common, Emily and Amy had quickly bonded.

Charlie knew he had to get on base. It was the ninth inning and the Eagles trailed by two runs with only two outs left. He swung at the first pitch and missed. The next two pitches were called balls and Charlie stepped out of the batter's box to look at the third base coach. As he stepped back in, Amy, Emily, and Walt clapped and hollered "Go Charlie, Go Charlie!" He crouched in his stance and watched the pitcher closely. The pitch came a little low and away and not wanting to risk a called strike Charlie swung. His bat made solid contact with the ball, driving a low liner toward the right field corner. Charlie raced toward first base, his eyes glued to the right fielder to see if he could stretch the hit into a double. The fielder, showing great speed, cut the ball off after the first bounce and turned to throw to second. Charlie had rounded first but returned to the base.

"Yo Charlie! Way to go! Way to go!"

Charlie had given his team a fighting chance. The coach of the other team came on the field and replaced the pitcher with his best reliever. Charlie watched with dismay as the pitcher overwhelmed the next batter with three straight strikes. One out to go. Roberto, the team's best hitter, stepped to the plate. But the pitcher gave him no good pitches to swing at, instead tempting him with low pitches around the corners of the plate. With superb batsmanship, Roberto fouled off pitch after pitch. Eventually the count rose to 3-2. The pitcher took his time before stepping back on the rubber. He glanced at Charlie on first then fired an inside fastball high in the strike zone. Roberto swung and hit the ball with a loud crack—a high fly ball to left. The crowd rose to its feet exhorting the ball to clear the fence. The left fielder raced backward at an angle to the ball's trajectory and it wasn't clear if he would reach the fence in time. Charlie sprinted toward second at top speed and as he rounded the base he saw the fielder leap high as his body slammed into the fence. As he fell to the ground he raised his glove high and Charlie could see the ball in it. He stopped half-way to third, fell to his knees and dropped his head to his chest in disappointment. The Eagle fans fell silent as the winning players stormed the field, their arms pumping in celebration, and piled themselves into a chaotic, jubilant mass. They, not the Eagles, were going to the state play-offs.

Charlie made his way through them and joined his teammates in front of the dugout. The two teams formed opposing lines on the field and he moved along shaking hands with all of the winning players and coaches, saying congratulations to each one. He was sincere about it; he admired their skill and appreciated the sportsmanship they had displayed during the game.

He walked to where Amy, Emily and Walt were waiting for him. Amy hugged him and whispered into his ear "you played great, honey." Emily hugged him too as did Walt. As he left the field, Charlie looked back and felt a sudden pang of sadness. His high school baseball days were over. He and Walt would attend their graduation in a few days.

At home, Walt showered and changed clothes, then he and Emily drove to Amy's house. Charlie had invited his teammates to lunch and a pool party. Amy and Emily grilled burgers and hot dogs for them and provided a variety of sides and snacks as well as desserts that they had baked themselves. After eating their fill, the boys lounged around for a while. When their overstuffed feelings receded, they splashed into the pool. Amy and Emily watched them enjoy themselves for a while and then begin to clean up. When Walt saw them, he nudged Charlie and both boys got out of the pool to help.

Later in the afternoon, after all their guests had left, Charlie and Walt went up to Charlie's bedroom to sprawl out and relax. After a while, Charlie got out his Xbox and started to play a combat game, marking his kills with an emphatic "YES!" Walt sat down at the PC and logged onto a multiplayer online space exploration game. While it had some combat, the goal was to explore the vast reaches of unknown space that the game developers had created. Walt loved the exploration and the combination of real science and the fictional elements of the game. He soon lost track of time.

"Hey! Come look at this!" Charlie suddenly yelled, jolting Walt back to earth. He turned and saw Charlie standing at the bedroom window. "What?" he asked irritably.

"Just come here." Walt got up and went to the window.

"Look at them," Charlie said.

The window overlooked the pool area. Walt looked down and saw Amy and Emily relaxing on lounge chairs and sipping wine. Both were wearing swimsuits he hadn't seen before. Walt's eyes were first drawn to Amy's white bikini. He looked up and down her body and a thrill of arousal stirred in him as his eyes dwelled on her somewhat skimpy top and the round shapely breasts it held and then on her hips and thighs exposed by the high cut of the bikini bottom. Her graceful legs were slightly opened and Walt stared at the narrow strip of white cloth between them.

Charlie's eyes had already moved on to Emily. He couldn't take his eyes off her body. It was petite, but far more attractive than he had imagined. Emily wore a dark blue one-piece bathing suit that managed to be elegant, modest, and alluring all at the same time.

As the spellbound boys watched, the two women rose from the lounge chairs and walked toward the pool. Amy was five feet eight with curved hips, and beautiful legs. Her upright medium-size breasts were prominently displayed by her bikini top. Her hips swayed as she walked and her breasts bounced slightly. Her long luxurious hair, the color of a rich dark chocolate, which usually fell to her breasts, was tied up in a bun behind her head.

Emily was shorter, five foot five or so. She had a slender, lissome body, well-proportioned and supple, like that of a ballet dancer. Her breasts were on the small side but the boys couldn't make out their shape beneath the dark blue fabric of her one-piece.

Amy and Emily passed by under the window as they walked toward the pool, presenting Charlie and Walt with a nice view of them from behind. Amy's bikini bottom revealed an enticing but not overly provocative expanse of her cheeks, moving up and down with the rhythm of her walk. Emily's one-piece was cut fairly high on her thighs and low in the back in a graceful curve. It did not reveal any cheeks but attractively molded her petite bottom.

"God our mothers are hot," breathed Charlie.

"Callipygian," said Walt.

"What?"

"Callipygian, from the Greek...possessing beautiful buttocks."

Charlie laughed. "Yeah, they're MILFs"

"MILFs?"?

"What are you, a choir boy?"

"If I were a choir boy, some priest would have fucked me by now," snorted Walt.

"Okay, it's nerd boy then. Mothers I'd Like to Fuck."

"Yeah, I knew that."

They watched as Amy and Emily slipped into the pool.

"Have you ever jerked off thinking about them?" Charlie asked.

"What?"

"Do you need me to explain, nerd boy?"

"No," Walt said and hesitated before he worked up the nerve to say "Not my mother..."

Charlie looked at him. "My mother?"

"Yeah."

"Well, at least now I know you're human."

"What about you?"

"Both, one or the other or both at the same time," Charlie said grinning, "They're both sexy."

They watched their mothers float in the pool and talk.

"Hey, let's get our suits on and join them," Charlie said, his voice rising with excitement. They quickly did so and were soon standing at the side of the pool looking down at their mothers. Charlie backed up, took a running start and bomb dived into the pool, throwing a wave of water over the two women. His head came up out of the water. "What are you ladies talking about?" he asked. Amy looked at him, water dripping from her hair and face. "We're debating whose son is the bigger idiot."

"Well, we all know the answer to that," Charlie yelled, looking over at Walt. Walt dived into the pool and swam to where Charlie floated. He grabbed Charlie's head and attempted to push it under water. Charlie reciprocated and the boys started to try and wrestle each other's heads under the water. Charlie suddenly stopped and backed away.

"Hey," he yelled toward Amy and Emily, "how about a chicken fight?"

"I don't know," Amy yelled back, "we haven't done that since— "

"Then it's long overdue, Mom," Charlie said as he moved toward her. Standing her up, he turned her around and dipped underwater. With a hand on the inside of each of her thighs, he pushed her legs apart.

Amy was startled but had no time to react before Charlie moved his head between her legs and lifted her out of the water perched on his shoulders.

Walt looked at his mother. "Mom?"

Emily looked at the waiting Charlie and Amy, then turned to Walt and nodded her head. Walt moved behind her, ducked under the water and emerged with Emily on his shoulders, then turned to face their opponents. The boys stepped toward each other until Amy and Emily were close enough to try and push each other. The battle was a mismatch and Emily soon tumbled into the water followed by Walt. They came up sputtering.

"No fair, you two are athletes," Walt yelled, knowing that Amy had played tennis in college.

Charlie glanced at him and then at Emily. "Okay, then lets trade partners." Emily and Amy looked at each other as the boys tried to suppress their grins.

Amy shrugged her shoulders, "Why not?"

Charlie quickly went behind Emily. Ducking under the water, he put his hands between her legs and gently pushed on them until Emily moved them apart. Charlie put his head between them, wrapped his hands around her upper thighs and raised his head until his neck nestled into Emily's pelvis. He lingered a bit savoring the contact, then lifted her out of the water. Emily was acutely aware of the contact; it had been a long time since any man had touched that part of her body. She felt herself blush.

Meanwhile, Walt had moved behind Amy and paused, feeling awkward about doing this with his mother's friend. Eventually Amy looked back over her shoulder at him and said "Come on, Walt." He ducked under the water and gingerly put his hands between her legs and spread them apart. He came up between them and wrapping his hands around her upper thighs, he stood up. He was acutely aware of her body pressing against his neck and shoulders.

The battle lasted longer than the first one but thanks to Charlies' superior strength, he and Emily prevailed.

"Still and always the cha—" yelled Charlie as Walt rose from the water followed by Amy, but he was stopped by the sight of Amy rising from the water unaware that her bikini top had come loose and was dangling from one shoulder by a single string. Charlie and Walt stared with open mouths at her breasts, round, firm and glistening with water, nipples erect from the cold.

"Okay boys," Amy said, "I'm going to get out of here before you make us do this again."

Emily, still on Charlie's shoulders, watched the boy's dumbstruck reaction to Amy's unknowing exposure with bemusement and a touch of embarrassment on Amy's behalf, but let them have a few moments of enjoyment.

"Umm, Amy," she called out, pointed toward the dangling bikini top. Amy looked down and emitted an embarrassed squeal. She quickly turned her back, replaced the top then turned back around with a sheepish grin on her face. She had to laugh though, at the sight of Charlie and Walt gaping at her with wide eyes and open mouths.

"Ahem, gentleman, show's over," announced Emily, then grinned at Amy. "Well, you've certainly given the boys a memorable start to the summer."

As Emily teased Amy, Charlie began moving his thumb back and forth, lightly caressing Emily's thigh. She felt the touch and looked down at his hand. She started to reach down to interrupt the caress, but something made her hesitate. She looked up at the sky, surprised by her momentary willingness to let the caress continue. After a few moments, she gently placed her hand over Charlie's and gathered in his thumb with her fingers. But she made no move to get down from his shoulders, again surprising herself by her willingness to let the intimate contact continue.

They soon climbed out of the pool and Charlie and Walt rinsed off under the outdoor shower by the pool and headed up to Charlie's bedroom to get dressed.

When Charlie had pulled on his jeans and tee shirt, he walked to the window and looked out at the pool.

"You know," he said. "We should sleep with them."

"What? You want me to fuck my mother?" Walt replied, startled.

"No...I want both of us to fuck your mother...and my mother."

Walt stared at him in disbelief. "That's insane."

"Come on Walt, I know you want to."

"Maybe, but I'm not sure it's right...and why the hell would they do that?"

"That's what we have to figure out. This stuff happens; we just have to find out why."

"How in the hell would we do that?"

Charlie smiled. "You're the brainiac. Where do you always start researching something?"

"Are you kidding?" Walt said, but sat down at the computer, brought up google and typed "How to seduce your mother."

"Holy shit! he proclaimed, "look at all these links!"

That night, everyone lay awake in their beds. Charlie and Walt masturbated to the vision of Amy standing before them in the pool, her beautiful breasts wet and exposed, and how she laughed good-naturedly at herself when she realized what had happened and saw them gaping at her. And their fantasies dwelled on the incredible pleasure given them by the touch of Amy and Emily's bare skin on theirs, and the pressure of their pelvises on their shoulders and necks. The intensity of Charlie's fantasy was increased by the thought of Emily allowing him, at least for a little while, to caress her thigh as her body maintained its contact with him longer than necessary. Charlie fantasized that she wanted that.

Amy lay awake recalling the sensation of Walt and Charlie's hands touching her inner thighs and spreading her legs apart. Though she believed it was innocent, no one had touched her like that for a long time. The feel of the strong but gentle touches lingered until she drifted off to sleep.

Emily also lay awake thinking about the game in the pool. She didn't want to admit to herself the tingle of pleasure she felt during her intimate contact with the two teenage boys. This isn't right, she insisted to herself, but her mind kept coming back to the feel of Charlie's hands on her thighs and the caress of his thumb. She fell asleep unnerved by her feelings.

* * *

Amy opened the door and smiled. "Hi Walt, it's nice to see you. Come in."

"Hi Amy, nice to see you too."

"Charlie's out by the pool. He was swimming some laps but I think he's done now. How have you and Emily been? I haven't seen either of you for a week," Amy asked as they walked to the kitchen. Against his better judgement, Walt let his eyes wander to the side to take a surreptitious look at Amy's figure. She was wearing white shorts and an unbuttoned turquois linen blouse over a white tee shirt. God, she looks wonderful, he thought to himself.

"We're fine. Mom's been grading final exams and attending post-semester evaluation meetings."

"Charlie tells me you're going to be a counselor at the Rec Department's science summer camp."

"Yeah. Since Charlie's going to be an assistant coach for the baseball camp, we're going to ride together. We start Monday."

"Would you like something to drink?" Amy asked as Walt headed for the door to the patio and pool area.

Walt turned around and smiled at her. "Actually, I would like some coffee, if it's not too much trouble."

Amy smiled back. "Never. I'll bring it out to you."

Walt found Charlie lying in a lounge chair by the pool, wearing sunglasses and his hands folded together on his stomach.

"Hey Charlie," yelled Walt as he set his laptop down on the picnic table under some trees closer to the house. Charlie looked over at him then got up and came to the table.

"Finally. I've been waiting to hear your report."

They sat down and looked across the table at each other.

"How soon can we start?" asked Charlie before Walt had a chance to say anything.

"Whoa, keep your jock strap on lover boy. We need to talk about this."

Charlie raised one eyebrow but when he saw the serious look on Walt's face he said "sure."

Walt paused for a few moments. "For starters, all those links were pretty much a waste of time. Most of them were fictional nonsense probably written by immature wanna-be Oedipuses too dumb to actually understand Oedipus—."

"Yeah, he was a pretty complex kinda guy," Charlie deadpanned.

Walt looked at Charlie, raised his eyes to the sky and shook his head. "There were also a few accounts of mother-son affairs that were maybe more believable, but none of them were helpful in explaining the mothers."

"Okay, so what do we do now?"

There was a long silence before Walt spoke. "I think we need to rethink what we're doing."

"Rethink?...why?"

"Well...I've been thinking about my mom a lot...and I...I don't feel right about what we're planning."

"You don't want to do it?"

"I don't know...maybe."

Charlie knew Walt well enough to know that whatever was bothering him had to be important. "I'm listening."

"I've been asking myself if what we want to do is just plain selfishness...I mean...are we just horny jerks looking to have sex with attractive women with the added thrill of it being taboo? If that's what this is all about, I don't want to do it...I don't want to turn my mother into a sex object." Walt picked up his coffee cup and emptied it then looked out over the pool.

Charlie eventually broke the silence. "I understand...and you're...I hate to admit it... but you're right."

They sat for a while in their own thoughts. They heard the patio door slide open and Amy came over to them. "More coffee?" she asked.

"Sure, Mom."

Neither spoke while they waited for Amy to return. She came and refilled their cups then went back into the house.

"You said maybe," said Charlie. "Do you think there's a way for us to not be selfish jerks?"

Walt seemed lost in thought for several minutes before raising his eyes to Charlie with a thoughtful look on his face.

"Tell me about your mother."

"What do you want to know?"