Pegging Fantasies

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By The Shires / Sssh.com

Alan looked over at Jill. As usual her face was buried deep in a stack of books. Not one book, or even two. At least four. She was studying for her exams, and her face showed intense concentration.

He sighed. They had a matter of weeks left before they were out of college and working full-time jobs. There was a lot of anxiety written around them and he knew that part of it was because of the uncertainty of what would happen after they closed out their college careers. Jill was likely headed off to LA to New York, some other big city. She had a few job offers already lined up in both those places. He had a job offer in LA, he just didn't know which place she would take on, and he wanted to be with her even after college ended. He was wild about her, but he knew she was right—there was something missing in their sex life.

Alan sighed again. That was partly his fault. If he could only get up the courage to tell her what he really wanted!

Well, maybe he should. If she thought he was a freak and crazy what of it? She'd break up with him and head to NYC, just to avoid him most likely. Or make sure they never saw each other when they go to LA.

Really, how much was he risking by telling her what he wanted?

Jill lifted her head. Her china blue eyes scanned across his face and her soft rosy lips parted in a smile. "You look frustrated."

Alan was frustrated. His lips parted and his tongue cleaved to the roof of his mouth. His frustration stemmed from not being able to tell her what he really wanted in bed. He was afraid she'd think he was weird. That she'd wonder if the sex they'd had before was what he really wanted. He enjoyed sex with her and he knew she enjoyed sex with him too—but both of them knew that there was a level of intensity missing in their time in the sack.

He couldn't say it. Instead he said, "I am. I was just thinking a good long walk is just the ticket."

Her eyes went to the windows. It had poured down the rain earlier and now that it was gone thick yellow sunlight hung around the half closed blinds. "You know what? That sounds great. I'm pretty fried."

She climbed up off the sofa, her long hair swinging to her narrow waist. His eyes went to her firm tits. Her nipples were hard, poking out the front of her dress. He wanted to go to her, lift her top and bra, and take the grape-like nipples in his mouth, roll them around and feel them harden, feel the texture change to rough and pebbly.

She ran a careless hand, her nails tipped in red, along her taut waist and stretched, a long smooth flex that made his whole body shiver. She gave him a long smile. "C'mon, let's go. We can grab some dinner while we're out too."

They set off. The streets were mostly empty. The dorms they lived in were connected to the downtown section of the campus and so sat in the middle of the downtown section.

Downtown was a funky little blot of streets and restaurants, boutiques and high-end bars and hotspots. They walked past that and into a grittier side of the neighborhood, the outskirts of downtown where the hookah, skate, and biker crowd found food and good times.

"Look."

Jill stopped walking and stared at a window. He came to a halt too. "What the hell?"
cThey gawked in at the window at the mannequin wearing a leather harness, a strap on harness with a bright purple dildo attached, and colorful pasties on the nipples.

Dear Jesus. It was like someone had reached right into his head and pulled out his fantasy. His mouth hung open. Jill, her eyes peering at his reflection, tilted her head in a gesture that he knew meant she was considering something. "That's kind of sexy."

Heat brushed the tips of his ears. "If you say so."

"I say it's crazy that they got by with setting up a sex shop in this neighborhood." Her tongue came out, rested against the full arch of her upper lip. Her eyes were fastened on the mannequin and tension made her shoulders square and lift. "Come on, let's go check it out."

His eyes went back to the sexless mannequin. The breasts and pasties were meant to suggest a womanly form and did, just enough to make the blood leave his head and pound down to his dick.

His feet dragged but he went. Jill went far faster. She was already through the door and standing near a shelf filled with a stunning assortment of cocks before the door even whooshed shut behind him.

His skin was too tight for his bones and flesh. Every time he tried to breathe his eyes went back to that mannequin. From the back all he could see was tight rounded ass cheeks with that sexy harness draped right above.

His stomach fluttered and his eyes widened as a gorgeous redhead dressed in a slinky, skintight latex dress came out of a room near the back and gave them a long smile.

"Hi there, what can I do for you?"

Jill said, "I don't really know. We just saw the mannequin in the window..." her voice drifted off.

Alan was shocked by that Jill was the most confident woman he knew. It was what had drawn them together, their shared confidence. Though he had to admit at that moment he wasn't feeling all too confident either.

Turned on, absolutely. Confident? Not at all.

The redhead smiled. "Oh, right? Are you into pegging or are you looking for something to use with a girlfriend?" Her eyes went to Alan. They grazed down his body. When she lifted her eyes again there was a glint of amusement there. "I'm assuming size wise everything's cool with you."

Jill put a hand on his arm. There was a possessiveness to the gesture that surprised him. Jill wasn't the jealous type and what was more up until that moment he was pretty sure they'd be breaking up and very soon.

The gesture lifted his drooping spirits. Jill's, "Yes, the size and everything else is fine."

His chest puffed out. He knew, of course, what pegging was. He'd discovered it by accident on a porn site a few years before and while he'd been dating Jill since right afte

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Written by Sssh.com
Cargado March 27, 2020
Notes They gawked in at the window at the mannequin wearing a leather harness, a strap on harness with a bright purple dildo attached, and colorful pasties on the nipples.

Dear Jesus. It was like someone had reached right into his head and pulled out his fantasy. His mouth hung open. Jill, her eyes peering at his reflection, tilted her head in a gesture that he knew meant she was considering something. "That's kind of sexy."...
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