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Oops, Mom Did it Again!

11/16/2024

In the previous few days, 38 y.o. Karen had caught her 18 y.o. step-son Jason masturbating, watched him, had him come to her bed to do it again, helped him do it another night, let him see her naked, gave him oral sex, let him touch and kiss all over her body and cum in various places. And, she had told her out-of-town husband Dan about it on the phone. Finally, she let Jason have sex with her while Dan watched from the closet.

Karen lay on her bed next to Jason having just finished making love. Jason then looked suddenly serious and said, “Are you sure Dad’s going to be O.K. with this, Mom?”

“Well, Sweetie Baby,” she began, “I’m pretty sure he’ll be very, very o.k. with it. But there’s something Mommy needs to tell you, Jason darling.”

“What?” Jason replied.

“Ummm…” she said, “Um, Daddy’s here.”

“He’s here?” he said, looking confused. “You mean he’s back in town? Is he coming home?”

“Well,” Karen said, “He’s home.” With that Jason heard the slight squeak of the closet door and turned his head around, extremely startled. His father, Dan was coming through the closet door. Despite Dan’s understanding expression, Jason was extremely nervous.

“Oh shit!” Jason said. “Dad! What are you…I thought you were…Dad, I’m sorry, I…” His father tried to calm him down, holding his hand up to indicate that his son didn’t need to explain.

“It’s O.K., Jason,” Dan said. “It’s really O.K. I’m the one who should be sorry.” Dan moved to the chair next to his and Karen’s bed and sat in it. “Mom told me what was going on. It’s totally fine. I’m really fine with it. She wanted it and you wanted it.”

“Really?” Jason said. “I thought you’d be mad. I mean…I thought…,” he began again.

“Sweetie,” his mom chimed in. “When Dad says he’s o.k. he means it. Don’t worry.”

“I’m sorry to spring this on you, Jason,” Dan said. “I couldn’t help get excited by what Mom told me you two were doing. I probably should have been mad as hell, but I wasn’t. And the more I thought about it, the more I wanted to see it. But I knew if you knew I was here, you probably couldn’t go through with it.”

“No kidding!” Jason said with a slight laugh, indicating that he was becoming less anxious about the bizarre situation.

“Did you enjoy the show?” Karen said to Dan.

“Oh my, yes,” Dan said. “Very impressive, both of you.” “Dad?” Jason began. “I don’t know how to ask exactly, but, how come you’re O.K. with this?” Karen smiled at his question and looked to Dan, waiting to see how he would respond.

“Well,” Dan said, “Your mom has always had a very healthy appetite for sex and a very, very open mind about it.” He smiled. “Early on I just learned to let that be a good thing. We love each other very much, but I know she’s always thought about being with someone else in bed. And I’ve been excited about that idea. I just never, ever thought it would be you!”

“We all got lucky, I guess!” Karen replied with a big smile. At that, she turned back to Jason and kissed him deeply. Dan, from his chair felt a new surge of excitement. “I loved doing it with you, Jason. Dan, I loved doing it with him!”

“I could tell,” Dan said. “I loved watching it. It was very, very exciting.”

“Hmmmm,” Karen said. “How exciting exactly?” She turned back to Dan with another big smile.

“Uuhhhh,” Dan started, “Exciting enough that there’s a pool of white stuff on the carpet just outside the closet.” He laughed, as did Karen. Jason looked puzzled.

“What do you…” Jason said. “Ooohhhhhh.” He paused. “Dad, you mean you, jerked yourself while we were doing it?” He looked very surprised.

“Yes, I’m afraid I did, Jason,” Dan replied. “I didn’t think I was going to, but I couldn’t help it.”

“Didn’t think you were going to!” Karen chimed in. “You couldn’t even keep your hands off yourself when I was telling you about what we were doing on the phone!” They laughed and this time Jason joined in tentatively, feeling still more relaxed. Karen turned to him again and kissed him, this time running her hand down his chest. His cock had begun to spring back to life already and Karen let her hand graze it next.

“Mmmmmm,” Jason moaned.

“Dan,” Karen said. “I think my boy is getting ready for more!” She put her hand on his hardening penis and began to stroke slowly as she kissed his chest. Jason was trying to concentrate on his mothers actions while he glanced nervously at his father, sitting in the chair observing them.

“Jason,” Dan said. “I told you, it’s O.K. Don’t worry about it. Just enjoy what Mom wants to do with you.” This settled Jason a bit more. For some reason he felt even more calm when his father reached his hand into his own boxer shorts and began massaging his own dick.

“Ooohhhh, Baby,” Karen cooed to Jason. “Are you getting hard for Mommy again? You liked putting this inside my pussy, didn’t you?” Jason nodded and moaned again as Karen kissed down his chest and stomach. Dan poked his increasingly erect penis through the front of his shorts. He couldn’t believe he was almost hard after cumming just minutes before. He thought that he hadn’t recovered that quickly since he was his son’s age.

“Karen, Sweetie,” Dan said, “I think he might want that in your mouth again.”

“Just what I was planning,” Karen replied, as she moved further down toward her son’s crotch. She took him into her mouth once more and tasted the remains of her own lubrication mixed with a bit of her son’s cum. She took him into her mouth and stroked with one hand. She was leaning forward from her knees, which left her beautiful behind fully exposed to Dan’s point of view. He stroked his hardening cock as he watched his wife suck their son and looked at her ass and pussy staring right at him.

“Oh, Mom…” Jason moaned. “It feels sooooo good.” He had now forgotten that his father was in the room watching the proceedings and he was now fully concentrating on his mother’s awesome mouth sliding up and down his erection. But Dan was fully aware that he was one of three in the room and he delighted at the excitement of what he saw. Before long, he couldn’t help move toward his wife’s beautiful bottom.

“Oh, yes, Baby!” Karen exclaimed as she felt her husband’s hands begin caressing her ass. Her pleasure was increased as he began kissing her firm behind, running his hands all over it. She briefly took Jason’s dick out of her mouth again to encourage Dan more. Dan began kissing into her crack and letting his tongue flick her asshole, which brought new moans of pleasure, which were muted by the big cock in her mouth.

“I love your ass, Karen Baby…” Dan said in a loud whisper. He kept running his hands over her butt and hips as his kisses moved down. He knew his wife loved to have him run his tongue from her asshole to her pussy hole and back. He licked her asshole more and made it very wet. He than followed the trail of his saliva down to his wife’s wet pussy. It took a few seconds for Dan to realize that the wetness of her pussy wasn’t just from her lubrication and his saliva. Dan was tasting his son’s cum leading of out his wife. Jason had fucked her and cum inside her just minutes before and much of his load was still inside her.

“Ooohhh,” Dan began moaning of his own. “Wowwwww,” he said to no one in particular. Karen did not realize that it was more than her two wet holes that was getting her husband so excited. Jason was busy focusing on the pleasures of his mother’s mouth and paid no attention to his father. But Dan was experiencing something he had thought about many times but never had the chance to act on. He couldn’t believe the excitement he felt knowing his tongue was encountering his son’s cum. He plunged it in further, then put his whole mouth on his wife’s waiting vagina. Dan sucked gently and continued probing with his tongue as Jason’s cum seeped out and into his mouth. Dan realized that his dick was not just hard, it was big and throbbing from the rush of what he was doing. Before long, Karen was nearing another orgasm from her husband’s licking and sucking. “Ohhh, Dan Baby!” she moaned. “Oh yesssss, suck it, suck it, suck it!” She put Jason’s erection back in her mouth and increased her movement up and down as her husband worked her pussy over with his own mouth. Dan began moving back and forth from Karen’s dripping pussy hole to her now wet and slippery asshole. She wriggled her hips and pushed into his face as he plunged his tongue into hole, withdrew it and moved to the other. Finally he landed on her clit and gently sucked as he felt her near orgasm. She took her son’s dick out of her mouth and held it close to her face as she felt a huge spasm overtake her. “AAAaaaaahhhhh, AAaaaaahhhh, Aaaahhhh, Ooooohhhhhhh, FFFFfffuuuucccckkkk! Ooohhhhhh….” Dan held his face against his wife’s spectacular bottom as he felt the waves of cumming sweep over her.

“I love you, Karen,” Dan said. “I love you so much.” Karen felt both the glow of her orgasm and the warmth of her husband’s words embrace her as the spasms slowed. Dan’s penis was fully erect and his next thought was that he wanted to plunge it into his wife’s wet pussy. But before he could act on that thought, Karen changed position and placed herself on top of Jason. She was about to fuck her son for the second time.

“Ride me, Mommy,” Jason said eagerly as his mother began to straddle his hard-on. She slid herself back and forth over him as head found hole. She wasted no time in sliding herself down his erect pole. “Oh, Mommy, yesssss…..It feels sooo good to be inside you!”

“Do it Jason,” Dan said. “Fuck your mommy. Fuck her hard with that cock of yours.” Dan’s words excited all three of them more. Karen rode harder, feeling her son’s meat slam into her body. Jason put his hands on her hips and pulled her up and down. Dan returned his hand to his own cock and watched in amazement as his wife fucked their son silly. Karen leaned forward and drew Jason’s head to her breasts. He lovingly kissed and sucked her nipples while she held him in place. She let it down slightly and kissed his mouth and face. Watching closely, with Karen bent forward but still riding, Dan could see his wife’s ass exposed again, as well as get a clear shot of their son’s dick plunging in and out of her pussy. For the first time he realized that as Karen had told him on the phone, Jason had a big dick, just like his Daddy.

“Yes,” Karen said. “Fuck me, Baby. Fuck your mommy. Fuck me!” With that, Karen rotated her body around, keeping Jason inside, but turning to face Dan. Her back was not to Jason and he put his hands on his mom’s behind as she rode him. Dan moved to Karen and began kissing her breasts as their son fucked her. Karen leaned back to encourage Dan to do more. He kissed, licked and sucked her boobs as she rode up and down.

“You’re so beautiful, Karen Honey,” Dan panted. Karen was riding Jason hard and both were moaning in pleasure. Dan kissed his wife’s breasts more, then moved down her fabulous abdomen. She seemed to sense where he was going and she began to whisper encouragement to her husband. She leaned back further, exposing her clitoris to him as she slid up and down on Jason. He looked directly at her pussy as it was penetrated by their son. He knew what she wanted and it was what he wanted as well. Karen slowed her ride to allow her husband to join in. Dan moved his mouth to Karen’s aching clit. Her slower movements allowed him to plant his lips firmly on her sweet spot and begin gentle licking and sucking. Karen continued to move up and down, but she slowed even more to fully experience these moments of ecstasy. Her husband’s mouth was on her clitoris and her son’s dick was in her pussy. Karen began to moan loudly as she experienced what felt like ultimate stimulation. Her son clutched her ass firmly and helped her maintain rhythm. Jason did not completely realize what was occurring, but he wanted his mother to feel pleasure and he knew that was happening.

“Oh, Dan,” Karen said breathily. “It’s sooo good. You’re both sooo good. Ooohhhhh! OOoohhhhhh!!! I’m gonna cum again!!” Loudly. “AAAhhhhhh!! AAAahhhoohhOOhhhh!!!” Near screaming, Karen came again, feeling one of the biggest climaxes of her life. Her husband’s mouth never stopped it’s firm sucking of her clit as her son’s cock slid in and out, filling her, then filling her again. No one had anticipated what would happen next.

As Karen’s orgasm slowed, her son’s grew nearer. Excited by his mother’s screams of pleasure, which he knew he had helped cause, Jason began moaning more loudly. Dan’s mouth remained in place on Karen’s pussy as she rode up and down. He couldn’t help realize that while he was stimulating his wife, his tongue and lower lip had been riding on Jason’s dick the whole time. Karen looked down at Dan and he up at her. She whispered quietly but intently, “Yes, Dan. Yes, yes, yes.” She nodded her head up and down and Dan understood.

Karen lifted herself higher on the next lift and as she anticipated, her son’s ready penis slipped out momentarily. But rather than return to her pussy, Karen’s hips moved back slightly and Jason’s cock slid directly into Dan’s mouth. Any reluctance Dan felt was overshadowed by seeing how much his wife desired this to happen. She continued to ride up and down along with Dan’s head as he sucked Jason firmly. His son suddenly erupted in his mouth. Dan was shocked and thrilled at the feeling, the taste, the jerks of his son’s dick. He took it all the way into his mouth and held it there while Jason spurted shot after shot of sticky, warm liquid. Dan let his son finish completely before allowing himself the pleasure of swallowing the big load and removing his mouth.

Karen fell onto the bed next to her son, who was coming down from his own heights of ecstasy. She put her head on his chest and held him close. Dan lay down next to his wife from behind and put his hand on her waist. Father, mother and son lay motionless, panting together, trying to comprehend what had just occurred.

After more than a minute had passed, Karen broke the silence with laughter. “What the hell was all that?” she said.

“Hell if I know,” Dan replied. “An orgy?” He laughed as well.

Jason replied, “Dad?”

“Yes son?” Dan said.

“Um, did you…” Jason stammered.

“Yes he did, Sweetie,” Karen said, jumping in. “I sort of begged him to with my eyes. I hope you don’t mind.”

“No, not really,” Jason said from a slight fog. “I didn’t really know what was happening, but it was cool.”

The three lay there as more minutes passed and they all caught their breath. Again, Karen broke the silence.

“Hey, Dan,” she said.

“Yes,” Dan replied.

“You didn’t get to cum again,” she said. You came in the closet. Then I came twice, Jason came, but you didn’t cum again.”

“I really kind of lost track,” Dan said. “I’m pretty turned on. It probably wouldn’t take me long. I’m sure there’s still time, eh kids?” Dan chuckled. Jason looked down the bed to something near his mother’s knee, where he saw the white thong he had removed from her not long before. He reached down and grabbed it, then handed it to Dan.

“Here you go, Dad,” Jason said. “Doing it in Mom’s underwear has worked out really, really great for me.” All three laughed together at this. Karen reached for the thong.

“Give me that!: she said. “Lean back, Baby,” Karen said to Dan, who did as she asked. Karen wrapped the thong around his very erect penis, leaving the head exposed. She stroked up and down slowly, knowing it would not take much to bring her husband to clilmax. Sure enough, he began moaning very shortly and his cock erupted with a gush of semen that went straight up, then came down on his wife’s hand and her thong.

“MMMmmmm,” Dan cooed. “Thanks Honey. So, anyway, where do we go from here?”

“Well,” Karen began. “I think I want to know which of Jason’s friends think I’m such a MILF! I think it’s about time for a sleepover.”

“Oh shit!” Jason said and all three laughed again and held one another in a tight threeway embrace.