“Look at me, Josh. Clearly, there is something wrong. You can’t even look at me when you are talking to me,” Diane said in a calm, caring voice.
Josh was Diane’s nineteen-year-old grandson who, as far as Diane is concerned, had been distant for the past few days. She asked him around to her place to find out why.
It took a while, but Diane got to the bottom of Josh’s stand-offishness. She had thought it would be easy, like girls and sex; Diana was half right. It wasn’t that straightforward. Josh somewhat sheepishly admitted that he had checked out some of Diane’s underwear drying on the line a few days earlier.
“And what did you think?” Diane asked, trying not to smile but failing.
Josh was enthusiastic in the first part of his reply, telling Diane he liked what he saw very much. However, Josh’s energy level dropped in the last part, slightly disappointing Diane. He said he didn’t think women of Diane’s age wore sexy underwear like that.
“Women my age indeed. You would be surprised how many ladies my age wear lingerie like mine. It makes us feel desirable.”
Josh didn’t think, “But why Gran? It’s not as if someone your…” Josh managed to stop before finishing the sentence, realizing what he was about to say.
“Someone my age. Is that what you were going to say?”
Josh had no idea how to save himself. He just blushed.
“I don’t know. You young ones. Why do you think someone my age can’t enjoy and shouldn’t have sex? Well, shock horror, your Gran loves sex, and I still partake as often as possible. Not as often as I would like, but I do alright.”
It was a shock for Josh. His grandfather had passed away only seven months earlier. He couldn’t believe his grandmother was having sex with another man soon after his grandfather’s passing.
“But Gran,” Josh said in a disapproving voice.
“No, Josh, don’t be so judgemental. It was you that checked out my underwear. Be honest; you wondered what I looked like in that black bra and panties, didn’t you? Yes, Josh, I know which ones you were checking out. Did you get a hard-on? What about when you are home alone in your bed at night? Does your cock go stiff, thinking of me almost naked? It does, doesn’t it, Josh? You wrap your hand around your rigid dick and wank yourself off, thinking about me. Where do you imagine squirting your creamy white seed when it spurts out? On my face, in my mouth. What about on my belly Josh? Or maybe on my shaved pussy. Yes, Josh, I got rid of my bush. My first young man advised me to. He told me younger men prefer shaved pussy, so I got rid of my pubes. I aim to please as well as be pleased.
One last incredible remark was left in Diane’s speech. “No, I think what you fantasized about was burying your cock deep inside me and filling my cunt with your youthful cum.”
Josh’s brain couldn’t comprehend what he had just heard. The language and turn of phrase. It was bad enough that Diane admitted she was having sex, but with more than one man stunned Josh.
The hardest thing for Josh to get his head around was Diane was right. He had jacked off thinking about Diane in her black lingerie and cumming on her. The difference was that Josh didn’t think of targeting any specific part of Diane. He imagined standing over her, letting his cum fly, and landing wherever on Diane.
“Wait here,” Diane told Josh, and she disappeared out of the room.
Josh remained seated on the sofa and tried to make sense of what had just happened. The initial shock was wearing off, and Josh realized how his own grandmother, no less, had turned him on. Josh’s hand rubbed his dick through his jeans. He wanted to release it but was afraid Diane might walk in on him. He hoped Diane would react positively, but he dared not take that risk.
Josh’s thoughts were interrupted when Diane shouted for him to join her upstairs. As he climbed the stairs, dozens of scenarios ran through Josh’s mind. Foremost in his head was that he just might be heading into an adventure he would never forget.
As Josh reached the top of the stairs, Diane called out she was in her bedroom. Josh stood at Diane’s door. He gave his dick another squeeze, took a deep breath, and walked into Diane’s bedroom.
“Fuck,” Josh said out loud rather than keep it in his head.
“Quite possible,” Diane said. “If you do me a favour.”
Diane’s comment barely registered. Josh was concentrating on Diane’s pose in front of him. Diane was kneeling on her bed with a radiant smile on her face. The black lace robe Diane wore was open, revealing black stockings, bra, and panties.
Josh had never dreamed his grandmother could look so sexy. Diane’s knees were just far apart; there was a gap between her thighs below her pussy. Her right hand rested on her hip, and that smile was on Diane’s lips. The only thing that topped the smile was Diane’s nipples peeking over the top of her bra.
“Jason,” Diana snapped, breaking Jason’s trance.
“Um, yes, Gran, sorry. What did you say?” Jason mumbled.
“The favour,” Diane repeated.
“Sure, Gran, whatever you want.”
Diane pointed to the camera on her dressing table and told Josh she wanted him to take photos while she posed. Josh grabbed the camera, began clicking away, and soon found that Diane knew precisely how to show herself off.
As the session continued, Diane removed her robe and asked Josh if she was right about him jacking himself off. Before he answered, Josh, watched Diane unfasten her bra and free her breasts.
It was much easier talking to Diane from behind the camera. While he focused on Diane’s partially naked body, he didn’t have a problem admitting he had jacked himself off picturing Diane in her underwear. He even confessed, without being questioned, that he finished himself off standing over Diane and letting his cum fly onto her.
“What about fucking me?” Diane asked.
Josh stopped looking through the camera and looked Diane in the eye, “Oh, yes, I thought about that, but you had a large thick bush.” Josh lifted the camera and firmly told Diane to remove her panties.
“Yes, sir,” Diane joked. She turned her back to Josh, pushed her panties over her bottom, and looked back at Josh seductively, and then Diane turned around to face Josh.
The front of Daine’s panties hadn’t moved much, so her most private part was still covered, but only just. Josh took a couple of photos and told Diane it was time her panties came off.
“All in good time, Josh. I want to tease,” Diane said.
“Tease, there is only me here. Why do you want to tease me?”
Giggling, Diane said, “Not you, silly. I want these photos to show online to the men I am talking to, and I want to ensure they have their cocks in hand before showing them what is between my legs.”
Josh was becoming less surprised by Diane and what she said. He did as requested and photographed Diane in many poses, with and without panties. Some he got a glimpse of pussy lips, but not many. Diane was meticulous in showing as little as possible.
It was only when Diane thought she had enough teasers her legs spread.
From then on, Diane was totally uninhibited. Josh clicked away while Diane modelled herself in many positions that showed off her shaved pussy. She spread her pussy lips, played with her clit, and fingered herself before bending over and fingering her bum hole.
The last few photos were close-ups of Diane’s pussy with her fingers holding her lips apart. The shine in and around Diane’s pussy laid testament she had not only enjoyed the session but had managed an orgasm.
Jason put the camera down and joined Diane on the bed. She was lying on her back, and Josh sat next to her. “Didn’t you say something about rewarding me if I did you a favour, Gran?”
“I might have,” Diane said cautiously. “Why don’t you sit by my feet, Josh?”
Josh moved so he was by Diane’s feet. “Wait a moment,” Diane told him, and she adjusted her pillows to sit comfortably.
Diane spread her legs and told Josh to kneel between them.
“Okay, Josh, you can see mine. Now let me see yours.”
Josh dropped his pants to his knees.
“My, Josh, you are a big boy, aren’t you?” Diane complimented Josh, admiring his hard dick. Diane lifted her leg and placed her big toe on the head of Josh’s cock. “Show me how you jack yourself off.”
Josh’s hand wrapped around his cock, and he began wanking himself, “I was expecting more of a reward Gran.”
“I know you were, but I am your grandmother. What you want isn’t right.”
Josh glared at Diane and noticed the tiniest of smiles, “Fuck you, Gran,” realizing Diane was teasing him. He put his hands underneath Diane’s ass and lifted her so her cunt hole was in line with his cock.
Diane’s facial expression changed to a wanting look.
“Can I?” Josh asked.
“Yes,” Diane replied, giving Josh permission to sink his dick into her, which he did. To the hilt.
What followed was an incredible experience for both of them. Diane let Josh ride her, revelling in Josh’s youthful vitality and energy. His young rod of steel pounded Diane’s cunt into numerous mindblowing orgasms. When the moment came for Josh, Diane could feel his cock pulsating inside her and could sense the warmth of his cum filling her.
When Josh finally pulled out of her, Diane wanted to suck him clean. She didn’t; she lay there enjoying the feeling of pure sexual satisfaction instead.
Josh didn’t let Diane indulge for long. After only a couple of minutes, Josh put Dine’s hand on his cock.
“Let’s do it again,” Josh said.
Diane couldn’t believe it, but Josh’s cock was hard again, or maybe he hadn’t lost his boner.
However, there was something about holding Josh’s cum coated prick that Diane couldn’t resist. To give her pussy a little time to recover, Dine rolled on her side and took Josh’s cock in her mouth. It was incredible how good Josh’s cum tasted, and Diane amazed herself at how far down her throat she took Josh’s dick without gagging.
The urge, however, for her pussy to be filled again with Josh’s pole became too intense, and Diane mounted Josh cowgirl. This time though, Diane took charge. Once his cock was safely tucked inside her, Diane gazed into Josh’s eyes and began to rock her hips slowly back and forth.
“Touch my breasts,” Diane told Josh.
Josh’s hands covered Diane’s small breasts, and she taught him how she liked them massaged. Diane’s eyes closed, and her head drooped forward. She moaned softly, enjoying Josh’s hands, but then her head jerked up. Diane squirmed, and then she giggled.
Josh had tweaked her left nipple between his thumb and forefinger.
Diane smiled a reassuring smile. Encouraged, Josh repeated the action on Diane’s left nipple and then both nipples simultaneously. Diane’s reaction was to increase her hip movement, more prolonged and forceful.
“Holy fuck Josh. How did you know Josh?” Diane said loudly as Josh twisted her nipples and pulled on them.
Realizing Diane was enjoying the pain, Josh adjusted his body so he could reach Diane’s nipple with his mouth. First, he bit down on Diane’s left nipple while twisting the other.
Diane pulled Josh’s head forcefully onto her breast, moaning long and deep. She held Josh’s head on her breast for as long as it took her orgasm to subside.
Once Diane’s senses returned, she pushed Josh from her breast and held his shoulders against the bed.
“I can’t let you go without doing this,” Diane said.
“Doing what?” Josh queried.
Diane lifted herself off Josh’s cock. She reached between her legs and held Josh’s dick while she nudged forward slightly and slowly lowered herself.
It was an entirely foreign sensation for Josh and his cock, because it was the first time anal for him.
Josh was afraid to move. He let Diane fuck him, which she did slowly, but it was too much for Josh, and he shot his load into Diane’s ass.
Josh apologized profusely for being so quick.
“Don’t worry, Josh, it was beautiful, and I am sure we will do it many more times.”
