Margarette Pegs The Delivery Driver – A Granny Pegging Story

Margarette sighed as she looked out of her bedroom window. 

Life was boring. Where had all the sparkle and the adventure gone? 

People had told her life would slow down once she hit her fifties, and she had laughed politely. These people didn’t know Margarette, she would never have a life that slowed down. 

At that time, Margarette had an active social life and many lovers. She loved to dance, and to travel. After twenty years of marriage, her husband Arthur had decided they would both be happier in an open marriage when she turned 48. 

And so Margarette got to relive her youth again, having many hook ups and even a manage a trois, while enjoying a loving marriage and an early retirement.

It was all so wonderful, until Arthur asked her for a divorce.

It had come out of nowhere, and left Margarette’s head spinning. She had assumed that their marriage was happy. He’d packed his bags up and left the same week.

Margarette’s heart was broken. The casual sex and parties were only fun while she had a husband to share them with when she got home. She began to feel self-conscious in front of her fashionable friends. The line between adventurous wife and aging slut was frighteningly slim, and Margarette had suddenly felt she was failing at life.

Gradually, she had withdrawn socially. She had kept her body in good condition, but she was afraid to date anyone new.

The truth was, she was lost without Arthur.

She internally scolded herself for day dreaming of ex husband again. Arthur was gone, and she needed to move on. Just about to turn away from the window, a movement caught her eye. Someone was coming up the drive.

Messy black hair with pale skin, long legs in jeans that were too short, a shabby t shirt that was too long. In one hand he was holding a brown package. Margarette had ordered a new clutch bag the week before and had mostly forgotten about it. 

This delivery boy was far more interesting than the package.

She watched him move, unaware he was being watched. He looked clumsy and unsure of himself, out of place on the drive of her smart country house with six bedrooms. Margarette hurried down the stairs to meet him at the door.

The older woman opened the door with the most friendly smile on her face, and the delivery guy grinned back in reply. He had a round face and his hair cut made him look very boyish.

Shouldn’t he be at an age where he wants to look a bit more like a man? She thought. Such a messy hair style. 

“Good morning.” Margarette greeted him.

“Morning Ma’am.”

Ma’am? So formal. Margarette’s stomach jumped a little, despite herself.

“A package. Do you know, I order so much I forget what I order.”

The delivery driver rummaged in a pocket to find a handheld device, and offered it over, looking at the older woman shyly from under his long hair.

“Would you sign here please?” he said softly, ignoring the opportunity for small talk.

“Of course.” Margarette had proudly reached the age and confidence of being very comfortable asking for what she wanted. But in the seconds before receiving her parcel, she realized she was nervous to ask. How thrilling.

“I’m Margarette. I’m just about to have breakfast. Would you like to join me?”

The boy immediately blushed. Flustered, he handed over the parcel and there was a second of electric skin contact. 

“I erm… I mean. I have finished my deliveries for the day.”

“I’m making bacon sandwiches. Come in. I’d love some company.”

He grinned as he decided. 

“Okay sure. I’m Logan.”

–

Logan ate his sandwich like he hadn’t eaten in weeks. Margarette watched as he wolfed it down, ketchup gathering at the edge of his mouth.

“Good?”

Logan nodded.

“Mmhm!”

As she cooked, he’d explained he was working as a delivery driver having dropped out of college a few years before. He was trying to get a career started as a video maker on the side, but it was slow going.

He was living with three housemates on the other side of town. No girlfriend.

Margarette read several more things that Logan didn’t say outright. The older lady prided herself on her ability to read people. 

Logan was ashamed of where he was in life. He was lost. And bored. He was handsome, but the girls his age passed him by, most likely due to his shy nature. Which fed into his lack of confidence, no doubt.

There was something about him that reminded her of Arthur. She remembered how much her ex-husband wanted to be dominated, deep down. He had been so submissive. He’d hidden his true nature deep, but after years of marriage, they’d been able to be so open.

It had taken a long time to extract it, but nothing made Arthur cum like being dominated. He had loved surrendering to her. 

In her mind’s eye, she remembered how good it had felt, to bury her strap-on into her husband’s asshole and fuck him while he moaned softly, his cock hard and leaking. Her husband was gone, but Logan was right here, eating sandwiches at her breakfast table.

“Are you bored, Logan?” The older lady asked with an unmistakable intensity.

“How do you mean?”

“I’m going to speak plainly. You’re handsome, well-spoken and tenacious. But you’re working a delivery job for almost no pay. Sharing a house with other men, with no girlfriend.”

“I, erm.” Logan blushed and looked down. But there was no snap back.

“Is this all you’re capable of? I think you can do better..”

“Look…”

Logan’s fire came out in only one word before Margerette reached over and ran her hand between his legs. 

As expected, he was half hard, and even half hard the size seemed impressive. He gasped and then relaxed and the moment he did, Margerette tipped his head backwards and kissed him in his seat at her kitchen table.

As he kissed back, his much younger tongue clumsily entering her mouth, her mind exploded with joy. 

Oh, you still have it, even past fifty, she thought. But how far is this pretty boy going to go for you? Will he leave after a kiss or is he more adventurous than that? Who are you, Logan? Let’s find out.

Maneuvering her well-toned body to sit on top of him, the older lady rocked her hips against the growing hard on in the delivery boy’s trousers.

“Well, you’re not disappointing in every area, are you? That’s a really nice cock you have there but I would guess you have no idea how to use it. How many girls have you slept with?”

“Five.”

“Don’t lie. How many girls have you slept with?”

“One.”

“Are you still lying?”

Logan paused, then relaxed under her.

“Zero.”

“Wow.”

“I’ve had a blowjob though! Two in fact…”

“That makes you a virgin, Logan. A virgin delivery driver, living in a house share. That’s such a shame, don’t you think?”

Margerette rocked her hips against his fully hard cock. She looked down and saw that he was leaking enough to make a small wet mark on his trousers.

“Come upstairs with me.”

She took his hand in hers and he followed her.

They entered her bedroom and this time the younger man initiated the kiss. Sloppy, eager, too much tongue, but it was so needy Margerette felt her pussy heat up under her skirt.

“No, no, no. That’s too much. Be gentle, less tongue. Try again.”

The second kiss was nearly the same as the second. Wow, he was desperate. That’s okay, she decided. He has plenty of time to learn.

“Okay, okay.” She broke the kiss. “I get it. You’re horny. You want to lose your virginity, don’t you?”

She reached and stroked the long dark hair.

“Yeah, yeah I do.” Logan whispered breathlessly, nodding.

“Understandable. But I don’t think you’re ready yet.”

The disappointment on his face was sharp, and then he went in for another kiss, which she shut down by turning her face at an angle.

“No, no, no. I’m not in the habit of just giving boys what they want. It makes them lazy. And you said you were bored.”

The Goddess in her was waking up. She realized she was going to make sure Logan never forgot her, not ever. She was going to be his sexual benchmark, for the rest of his life.

She reached into his trousers and gripped his big cock, wet from leaking out everywhere, and rubbed softly backwards and forwards.

“I think I know just what you need. Turn around.”

Immediately, Logan did as he was asked. He was so compliant. This behavior had taken years from Arthur. Years of trust, of convincing he was allowed to be led, years of work and gradual convincing that he was allowed to submit.

And here was Logan, offering everything up after knowing her less than an hour.

“You realise you’re a slut, Logan?” She didn’t wait for a reply. “Bend over.”

Once again, the response was immediate. His brown asshole was exposed and on display to her. She smiled slightly and reached into her bedside draw for her lubricant.

Pumping the bottle into both hands, she rubbed her hands together. Her left hand reached under and held his young cock. Two fingers on her right hand pushed into his asshole slowly but firmly. Logan moaned and pushed backwards with his hips, wanting more.

“Really? I’m old enough to be your Grandma. Doesn’t that make you feel weird? My fingers are right inside you.”

The reply was a desperate moan, Logan trying to take more fingers inside himself. Margarette stroked his cock gently, keeping him totally hard.

“Okay then delivery boy. You’re really asking for it. And so I think I’m going to give it to you. I am going to take your virginity.”

Logan immediately begins to turn his body and the older woman stops him in his tracks by gripping his cock firmly.

“Oh no. Not like that. I’m going to fuck this asshole with my strap on. How’s that going to be for you Logan? Getting pegged by a Grandma before you even feel a pussy for the first time?”

There were no moans, but Logan’s body visibly relaxed. Acceptance. Perfect.

Margarette praised herself for not getting rid of her extensive sex toy collection. She had been so tempted and now, she couldn’t be happier to have resisted. Her favourite strap on was constructed and ready for duty in her toy box.

She pulled it on and massaged another huge squirt of lube in to Logan’s asshole, pushing it in to him with her fingers, getting him ready.

“This is going to feel strange at first. Just relax for me.”

Logan took a shaking breath in, and the older woman stroked his cock again, he was so hard. A wave of desire gripped her. She did want to fuck him. But today wasn’t the day. She wanted this for him. For both of them.

Gently, she positioned the strap on at the entrance to his ass, and then positioned his hips so he could take it inside the most easily.

“Are you ready to get pegged by Grandma? Yes? Okay then. Here I come.”

Slowly, she sank her strap on it to his young body. He accepted it wonderfully.

“Oh Logan. You’re not a disappointment here either. Your asshole is taking this so well. It’s swallowing my strap-on like it was made for it.”

Logan, once again pushed his hips back, desperate to impress her, desperate to be filled deeper and harder.

“Oh, you really are a slut. You’ve lost your anal virginity to me. Losing your anal cherry first like a whore, such base behaviour. What would your housemates think?”

The dark haired boy responded to that, rocking on the plastic cock desperately. Margerette reached down to stroke his cock again. Running her hands over his balls, she noticed he was already extremely close.

“I’m going to make you cum in under thirty seconds Logan.”

The noise he made was practically a cry, and Margerette placed both hands on his hips, positioning herself in such a way that she would be rubbing his prostate hard and fast. She pulled him towards her, so he had no choice but to take the whole strap on length.

“You’re about to cum harder than you have in your whole life. You ready?”

The string of yeses that came out of the delivery boy sounded like begging.

“Okay then.” Too easy. So easy.

Margarette accelerated her thrusts all at once, pounding in to his hole fast and shallow. Thirty seconds turned out to be an over estimate. Logan came on her duvet after ten at best, covering the sheets in sticky white cum.

Margarette pulled the strap on out and Logan rolled on to his side, breathing hard, his eyes fixed on the middle distance.

“Good?”

“Mmm!”

The older lady’s inner sex Goddess was dancing for joy, but she kept it well hidden for now.

“I’ll get you another bacon sandwich.”

These Grans Want You To Make Them Cum

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