When school was over Jake headed to his grandmother's house under the belief that she needed help with new furniture. Whenever he visited he always ended up staying for dinner. And then they would usually hang out and she would teach him how to play cards and he would teach her how to play video games. Sometimes she would give him a beer or make him whatever cocktail she was having. It was always a lot of fun for both of them. She was a blast and basically acted like more of a friend than a grandparent. She had always let him get away with murder. He loved visiting with her.
But this time Jake was moving swiftly while working on excuses in his head for why he wouldn't be able to stay. He wanted to get whatever it was she needed doing and then hurry on home to his mother and the all-night fuckfest that she had promised him.
When he got to Claire's house he went inside and called out for her. She yelled that she was in the living room and to come join her. As he walked to the living room he started in with his excuse.
"So grandma, listen. I'm not going to be able to stay for dinner. I've got this school project that I need to get started..."
He lost all words when he saw her. Claire was sitting on the couch with her shapely, tanned legs crossed and her arms stretched out along the top of the backrest. She was wearing a short, sheer lace, dark blue robe. Underneath that she had on a light blue babydoll negligee that barely contained her large breasts. On her feet were matching high-heeled, blue fuzzy slippers. And on her beautiful face was the biggest shit-eating grin.
"Hey there tiger! You were saying?"
"Uhh..."
"Cat got your tongue?"
All Jake could do was stare. All of those strange feelings that he had for her were now coursing through him. He had pushed them down inside of himself because while it was one thing to think of your MILF mom as hot, your grandmother was really a different story altogether. But here she was, looking unbelievably sexy. And the room was full of that weird sexual, tingly feeling. He tried to snap out of it.
"Grandma, umm...Mom said you have furniture you need moved?"
"Oh was that the excuse she gave you? That's a pretty good one! No, no dear. I don't need any furniture moved, however, we may cause some furniture to move once we get started though."
"I don't understand. I thought that..."
"Come here and sit down beside me sweetie and I'll explain everything."
She patted the seat on the couch beside her and Jake went and sat down. She turned to face him and put her hand on his thigh.
"Jake dear. I'll just come right out with it. I know everything that's going on with you and your mother."
"You do!?"
"Yes, sweetie. She told me all about your premature ejaculation problem."
"She did," he asked, completely mortified.
"Relax sweetheart. It's ok. She came to me not sure how to deal with it and I explained how to fix you."
Jake just looked at her stunned.
"You mean you told her to, uh...to..."
"To fuck it out of you. Yes I did. And from what she says it sounds like it worked. It sounds like it worked so well that you've actually managed to be a very naughty boy Jake – very naughty indeed."
"I have? What did I do?"
"Don't act so innocent! Why, you fucked that poor woman senseless! And then kept climbing on top of her and fucking her some more. You fucked my poor daughter so much that now she's too sore to give you more practice tonight."
"She told you about that?!"
"Uh-huh. But I can't really blame you. Pussy just feels so good doesn't it?"
Jake nodded his head.
Claire got up and faced Jake, and slowly undid the tie to the robe and then let it fall to the floor, revealing in full the lacy babydoll negligee that only had one button under her breasts and then fanned out, exposing her stomach. She was wearing a light blue matching pair of skimpy panties. Age had made Claire much more filled out than her daughter. Her thighs and ass were thick but firm with just some sag. She had a slight pooch to her belly but it was still very flat for her age. She looked amazing for fifty-eight, with her red hair cut to a bob.
"Go ahead and look, Jake. I like how you look at me. I've caught your glances whenever I'm wearing a swimsuit or my workout attire. I think it's cute."
Jake feasted his eyes on her. He felt his cock rapidly growing in his shorts and began to shift in his seat. Claire sat back down and put her hand on his bulge.
"Jake, like I said. It was my idea for her to seduce you in order to get you past this problem. And in order to make sure that your mom is doing a good job, I'm going to conduct a sort of student/teacher evaluation if you will."
"An evaluation?"
"Yes," she said as she squeezed his bulge. "So dear, I'm going to evaluate your progress, and based on that I'll know how well my daughter is doing. Does that make sense?"
"So we're gonna, we are going to..."
"We are going to have a lot of fun Jake," she said as she moved in closer to him. "You're going to give your sore mom a much-needed night off, and I'm going to be her stand-in tonight. And through that, I'll know how good of a job she's done."
She leaned in and kissed him with an open mouth, and soon they were making out. She lifted up his t-shirt and pulled it over him and tossed it on the floor, and then ran her hands over his muscular chest and torso.
"My god Jake. You've really turned into quite the stud."
She then leaned back and pulled him with her, so that she was laying on the couch with him on top of her. She then broke the kiss and looked at him with a mischievous grin.
"Jake baby, we are going to have so much fun tonight," she repeated, and then she went back to kissing him.
They made out and were soon grinding their hips into each other, dry humping on the couch. Jake started to neck her and slowly began to move down. He undid the button on the negligee, releasing her big tits, and began to squeeze and suck on them. Claire gasped and ran her fingers through the hair on the back of his head. Jake kept moving down, kissing all along her belly. She was impressed by his initiative and she was soon lifting her butt up to help him remove her panties, which he tossed onto the floor.
Jake stared at her pretty pussy. She kept it well groomed but it was definitely more hairy than his mother's, and it excited him. And like his mother's it was a very pronounced, fat pussy. He then dove in and started to eat her, causing her to gasp again. He ran his hands up and down her smooth thighs, loving the feeling of her shapely legs.
Soon Claire was firing off and coming into Jake's face. He held on and ate her through her orgasm. Once it subsided he gently kissed her inner thighs until he felt her take his head in both hands and begin to pull him up to her. He crawled back up and laid on top of her and they kissed.
"Well, A+ so far honey! Goddamn that was good. You've really been practicing on your mom's pussy haven't you?"
"Oh yeah. I could eat that sweet box of hers all day. Same goes for yours Grandma," he said as he leaned down and kissed her. While making out she reached down and grabbed his shorts.
"Let's get you out of these so that we can get to the good stuff, ok?"
Jake got up and removed his shorts and underwear and watched Claire's eyes get wide as his massive member came into view. He was completely hard.
"Oh dear, would you look at that! I might be in trouble here."
While laying on the couch she reached out her one hand and took hold of his hard prick and began to stroke it.
"Oh my Jake! I knew you were hiding something substantial in that wrestling singlet of yours. But this looks and feels even better than I imagined!"
"Mom calls it my 'pussy hammer'," he said with pride.
"That's a wonderfully appropriate name for a cock this beautiful," she said while stroking it. "Mmmmm, I'm going to have so much fun tonight with this pussy hammer."
She gently pulled on his dick and guided him back onto the couch, where he lay on top of her. Claire spread her legs and bent her knees, and still holding his cock, guided it to the entrance of her vagina.
"Ready tiger?"
Jake excitedly nodded his head.
"Ok, now once you're inside I'm no longer grandma ok? I'm Claire. Understood?"
Jake nodded his head again.
"Ok tiger, take it away."
Jake pushed forward, sinking his prick into her wet pussy, causing her to lay her head back and close her eyes.
"Goddamn, that's a good dick," she said. "Ok Jake sweetie. Show me what you've learned."
Jake was extremely excited and started to thrust into her. He leaned down and pressed his body against hers and started to passionately make out with her. He tried to focus on kissing her and not how good her body felt underneath him, and especially not how good her pussy felt.
He was surprised that she felt just as good as his mother, and figured that the vagina must really hold up over time. Being inexperienced he wasn't sure what he expected. But he tried to focus on these thoughts as he ground his hips into her.
He briefly stopped kissing her and exclaimed, "Goddamn grand..., uh Claire...goddamn you feel so good!"
"You too, tiger! Shit, that pussy hammer is so mmmpphhhh..."
Jake had pressed his lips back against hers and started to pump his hips harder. Claire was moaning into his mouth and had started to meet his thrusts. He knew that she was starting to cum, so he squeezed himself tighter into her body and grinded his hip thrusts into her as far as he could, causing her to break their kiss.
"Oh Jesus that's deep Jake! You're hitting everything tiger! UH! AH! Mmmmm, so good baby! Mommy taught you well! Oh Jesus what a good boy you are!"
He put his mouth back over hers and kissed her deeply as he sent her right into another orgasm. The sensitivity was just too much for her and she wrapped her arms and legs around him and held on tight, trying to ride out another orgasm as it shot through her body. She was practically screaming into his mouth as he pistoned his cock in and out of her pussy.
Having sex with this beautiful mature woman on her couch, the feel of her body underneath him and her legs wrapped around him, the baby doll negligee, and the feel of her wet pussy swallowing his cock finally became too much for Jake. He was a goner and he knew it.
"Gra...Claire! I gotta, I can't...I gotta..."
"Go ahead, tiger! It's your turn baby! Your turn to cum! Let my pussy make you cum sweetie! Fill me up, tiger!"
"AH! Shit! Oh Christ you feel so fucking good," he yelled as he proceeded to blow his load, sending spurt after spurt of jizz into her. His thrusts became more erratic as he worked his way through his orgasm. Claire ran her hands all along his body and kissed his neck, trying to make everything as pleasurable as possible for him.
When he was finally done he just lay there with his full weight on top of her and they both caught their breaths. Claire continued to gently rub his body and back as he lay there on top of her.
Jake started to gently move his hips again, slowly thrusting his dick in and out of her pussy. They kissed and just took a few minutes to just enjoy the afterglow, each other's bodies, and the continued penetration.
"How did I do," Jake asked.
"Another A+, tiger. Your mother has really taught you well. A+ so far for her too. Now let's sit up. I need to suck that gorgeous cock of yours."
Jake pulled out of his grandmother and sat back on the couch, his slimy cum covered dick sticking straight up. Claire swung her legs off the couch and got up and knelt in front of Jake. She took his prick into her hands and admired it.
"Your mother was right Jake. This is one of those special cocks, attached to a very special teenage boy. I'm gonna suck it sweetie and then we'll fuck some more, ok?"
"That sounds wonderful!"
Claire then leaned forward and took his cock into her mouth. She sucked up and down a few times with her hand stroking his lower shaft. Soon she removed her hand and was completely deepthroating his hammer. Jake threw his head back and closed his eyes.
"Shit that's good! Goddamn, you're swallowing all of it. So good..."
Claire knew that the best blowjobs were sloppy ones, and her mouth produced a ton of saliva, leaving a wet trail on his cock that dripped down to his balls. Soon the room filled with the loud, wet sucking sounds as her head bobbed up and down on his hammer.
