Pegging Fantasies

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?"

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."

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 after he had never dared utter that word aloud but since the redhead had he decided to go for it. ""What's pegging?"

Jill gave him a sidelong look. Then she looked back at the redhead. "Yeah, what is that?"

The redhead moved. The dress shifted and clung to her pale skin. "Well basically it's fucking a man in the ass. A woman fucking a man in the ass. It's not what you'd count as gay sex as the couple doing it is usually heterosexual."

His heart nearly exploded. All his fears wiped out, just like that. Jill's face showed an avid interest. "I see. So..." she turned to look back at the mannequin. When her head came back around her cheeks and forehead were flushed a mottled red.

Was it possible? The redhead smiled. "I love it. My boyfriend loves it. It's only logical since the stimulation of a man's prostate is done through the ass."

His cheeks went hotter. He was literally tongue-tied.

The redhead spotted a well-dressed man coming through the door and held up a finger. "You two look around. Have fun. I'll be back." She headed for the man and after a moment steered him toward some interesting looking furniture.

Jill turned to the shelves. Her face wore an expression of complete longing. Her fingers brushed against a box that showed the picture of a woman's lower body with a harness and cock attached. "I guess that is about the weirdest thing you've ever heard." She gave him a sidelong glance.

He shook his head. "No. I mean I saw it once." His cock lifted again, pulsing against the front of his pants. Little drops of fluid dripped from the head.

She gave him another side eye. "You did?"

"Um yeah. Some guys were watching porn one night." One guy. Him. Whatever. She probably already thought he was a pervert anyway. "It looked, on the movie anyway, okay."

Her hand grazed his arm. She turned and he did too. She pressed against him. His cock met her lower belly. Her whisper came to his ear ardent and feverish. "I want to try it but I understand if you don't."

Oh.

God.

How long had he wanted to hear those words? He swallowed hard. "I don't know how to do that."

She bit her bottom lip. She released the plump flesh and then licked it, a gesture that only served to make him even harder. His and heart pounded and his toes curled.

"I don't either but I imagine it wouldn't be hard to figure out." She took the box of the shelf and opened it. The harness came sliding out, a few strips of thick but supple leather. The cock was long and slightly thick. A beginner's cock is what guys called a dick that size on another guy.

His head pounded. His breath hitched in and out of his throat as he surveyed first her face, her glowing and rapt face, and then the cock. It was fleshy and wrapped with fake veins. Little textured knobs stood out along the shaft. He swallowed hard. "I mean there can't be any harm in trying."

"You'll need lube."

The redhead. He'd forgotten all about her. He hoped she wouldn't look back down. He knew she might not even have to. His dick was so hard his pants had formed a tent right there at his crotch.

She reached behind her and came up with a bottle of lube. "You could give it a go with some good old Vaseline or whatever, some people say they hate lube but if you're a first timer—or not—lube makes it a lot easier and far more pleasant for both of you. That harness is a good choice to. If you put it on right the base will rub right against," her hand cupped her crotch, fast. Then she moved it.

Jill panted out, "So that's it? Just lube it up and..."

The redhead grinned. "You could always jack him off too, or make him do it if you're worried about getting distracted. On a first time around I'd suggest he do it."

Goddamn! She made it sound so...so normal!

That had been his fear the whole time. He had always thought it was somehow wrong and abnormal to think something like that, pegging, was sexy and hot. Something he wanted.

But it didn't sound like it was at all.

Jill looked at him. Her face was so intense he lost his ability to think. "Yes?"

It was now or never. "Sure why not?"

Had he just managed to sound that off-hand about the whole thing? He had. Jill slid the harness and dick back into the box and said, "We'll take the lube too."

The redhead rung them out and discharged them back out into the street with a thanks and goodbye.

He stood there, dizzy and close to hyperventilating. Jill drew a ragged breath. The little pink bag, unadorned but for the candy-pink color, swung form her arm. "You...um...you want some dinner?"

Dusk had begun to settle while they were in the store. College students didn't really drift down that far too often and the people on the streets gave them and the bag knowing looks. "No, no let's get back to the dorms. I can order something. Pizza. Chinese maybe."

She took his hand. "I'm glad you have a private room."

His chest lifted and fell. "Me too." Especially since you're about to fuck me in the ass.

Holy fuck. She was about to fuck him in the ass!

They hurried through the streets and back into his room. Her books lay where she'd left them as did his. He turned to her, suddenly unsure. "Um...Jill you don't have to if you don't want to."

Her eyes held his. "Do you want to?"

Yes." The word escaped his mouth in a long sigh. "I really do. I just want to make sure you do."

"I do." Her pulse beat high and hard at her throat. Her nipples plumped against her top and his eyes went to them. She lifted her shirt, revealing her creamy skin below. He watched, stomach fluttering, cock so stiff he could not even move for fear of fainting. His ass cheeks kept clenching and loosening in anticipation. Her clothes lay on the floor. He grabbed his shirt and whipped it over his head then he yanked his jeans and boxers off. His cock stuck up at a direct angle, purpled and engorged.

Jill slid the harness over her hips, her brow furrowing as she looked at the harness and then the cock she held in her hand. Her face cleared and she stuck the dick through the slid it in the harness, her hand adjusting it.

His cock throbbed violently. Just the sight of Jill, her blonde pubic hair and lean hips, full breasts and the hard cock, was enough to take him close to the brink of an orgasm.

He gulped as she came closer. Her hand rubbed along the cock, stroking it in an intimate and sensual way. His eyes went to her fingers and the dildo appearing and disappearing in her palm.

She went to her knees, her wet mouth sucking him in and down her throat. The sensation was immediate and hot. His eyes closed and his hands tangled into her hair, his hips thrusting forward while a groan burst from his mouth.

She sucked him for a few minutes, taking him so close to coming he was standing on his tiptoes and thrusting his hips helplessly. She pulled her mouth off his cock with a wet pop.

Jill stood and pushed him toward the bed. He went over it, his face meeting the mattress and the welter of blankets. She pushed him further into the bed and then he was on his knees. He lifted his ass higher. Her finger probed the delicate flesh between his ass and balls. She cupped his balls in one hand, squeezing gently and his eyes closed then opened again as waves of pleasure coursed through him. Her fingers spread his cheeks and her fingers ran along the dark cleft between his cheeks. The sound of the bottle of lube popping open made him stiffen but she whispered, "Relax, I won't hurt you. I promise."

His body sagged back into the mattress. The lube was cold and oily. She rubbed it into the pucker of his ass, sliding a finger inside him slowly. The sensation was so intense he growled out, "Oh fuck yes!"

"Yeah, that's..." her voice lost strength then came again, "Holy fuck. I like this."

"So do I."

Her hands held his downy cheeks apart. The tip of the cock pressed against his asshole. His sphincter resisted it, tightening and pulling close together. She slid in just a bare inch, a small inch but the sensation went all the way into his belly and balls.

Her hand cupped his balls, squeezed. He grabbed his pulsing cock with his hand and shafted it rapidly.

The cock pushed in a little deeper. His hips slid backward, and his teeth clenched as she kept going, the dick slipping further into his tight dark tunnel. The tiny aperture opened for her thrust and he whimpered, his hand working faster. Thin drops of fluid spilled along his fingers as she began to buck her hips harder. Her grunts were as loud as his.

The feeling of the cock deep in his ass was beyond anything he could have ever imagined. Sweat hug from his hairline, dripped onto the pillows. His cock throbbed and heated beneath his fingers. She went deeper yet. His ass felt open and violated, his toes curled and he bit at the pillows. His body jerked and jumped.

"Oh holy shit. Holy fuck, Alan that feels so very good." Her words washed across his back on a puff of exhaled air.

His knees gave out. Her hips slammed against his. His ass cheeks bounced and jiggled. He opened for her, then closed around her dick. He squeezed it, hard, as she withdrew, trying to keep her within his body.

He came with a mighty roar. Semen coated his fingers, hot and sticky. Her nails scraped along the skin of his back, leaving bloody furrows. The pain just made him come harder.

She collapsed on top of him, pressing his weight into the mattress. Eventually their breathing returned to normal. She withdrew slowly. His asshole dripped lube and his cock let out one last little dribble of fluid.

Jill got up and went to the bathroom. She came back without the cock and harness. She held a washcloth and she pressed it to his violated asshole, the warmth and wetness of it soothing away the residual pain.

They lay there, together, cuddling next to each other.

She finally spoke. "I wanted to tell you, for a long time. It was just that...well I didn't know if you'd think I was weird or something." He caught her face in his hands. "You thought about this before?"

She giggled. "Yeah, why do you think I took you by there? I was hoping you'd get turned on."

Wow. He started to laugh. "I don't think it's weird at all. I like it."

Their fingers tangled together. Her eyes held contentment. "I'm taking the job in LA. I was thinking, if you wanted to, that we could maybe—you know—get a place together out there."

He grinned. "I think that is the best idea I ever heard. Other than the whole...you know, last one."

She chuckled. Their lips met in a kiss.