Does he win the bet?

Not easily

Chapter 14 by Pornwright

When they got to her apartment, Kelly – Paul had gotten her name along the way – was clearly eager to see his dong, though not so much from horniness as from curiosity. She led him straight to her bedroom, and after he shut the door behind himself she said “okay, drop trou and let’s see this thing.”

So Paul did. He was semi-hard, and sporting between 7 and 8 inches. He took his shirt off for good measure; shirtcocking is never a good look.

“Shit, that’s the biggest I’ve ever seen in person. And it’s not even fully hard yet, is it?” Paul shook his head. “May I?”

“Of course.”

She grabbed his cock and started… investigating it. Wiggling it around, bending it back and forth, sliding the skin around. Not trying to arouse him, just to explore his strangely huge cock. Pretty soon she got down on her knees, at first maybe to get a better look, but soon she was sniffing it, and then giving it some exploratory licks. While it wasn’t anything resembling a blowjob, or a handjob, it still did the trick for Paul, and his cock kept rising until it stopped at a thick hard size that did look like about ten inches to Paul – just like the dildo he might be buying Kelly. It must have adapted to her fantasy, because it’s not the cock he had a few hours ago.

After another minute or two of investigation, while Paul stood silent and bemused, Kelly stood up and said “Okay, I do want you to fuck me with that thing. I don’t know if I’ll get a chance like this again. But to be clear, size isn’t everything, and I’m still not convinced you’ll actually be more satisfying than a toy. And if you’re not, you lose the bet, and buy me my new toy.”

Paul assented, and Kelly proceeded in a businesslike way to get ready. She finally removed her clothes, revealing a toned body (with a nice six-pack), large areolas, and an unruly mass of pubic hair. She produced a bottle of lube from a bedside drawer in which Paul caught an intriguing glimpse of a few sex toys: dildos, at least one vibrator, maybe a butt plug, and some things he couldn’t quickly ID. She applied the lube liberally to both of them, then proposed “I think it’ll be best if I lay on my back with my ass at the edge of the bed, and you can fuck me standing up. Sound good?”

Her no-nonsense approach was a bit offputting, but that position sounded fine to Paul (though he doubted they needed to choose a position to maximize depth). So they took their places, she rested her legs over his shoulders, and soon Paul’s ten-inch monster was lined up with her slippery hole. He met her eyes for one last consent, she gave a little nod, so he started pushing in.

Given the size of his cock, Paul expected to have to go slow, but the lube was good and her cunt was accommodating, and he quickly found his thighs pressing against her ass, and his whole cock inside of her. She did let out a moan at this, one of the first signs that she might actually be enjoying herself tonight, and not just trying out a novelty. She kept up the moaning as Paul began thrusting in and out of her, starting slow, but taking such long strokes that he decided to stagger his feet for better stability. It felt good, but not mind-blowing, and Paul had time to reflect that if she took a huge cock like this one so easily, it wasn’t any wonder that she was skeptical of the ability of men to please her.

He gradually picked up the pace. While her moans increased in frequency, she didn’t actually seem very close to coming, as far as he could tell. He considered going faster and harder to see if that was what she needed, but if he tried and it wasn’t, he’d be in an awkward spot. He decided to try communication. “So,” he asked, “is this better than a toy?”

“Toys,” she spoke between strokes, “have more. Texture.”

Texture? he wondered. What does she mean? Then he remembered that the dildo she wanted had some ridges, and one he’d caught sight of in her drawer had some bumps. Whereas his cock was almost a perfect cylinder, the head barely bigger than the shaft. Well, he thought, if that’s what she wants, why isn’t she getting it? A bigger head would do the trick. Maybe she just needs some prompting.

As he kept pounding away, he asked “How could my cock have more texture?” She bit her lip, perhaps in thought, perhaps in pleasure. Paul wondered if his question would successfully change her fantasy.

Soon he had his answer, but not how he expected. He felt a strange feeling in his shaft, of pressure and hardness. He looked down to see his cock had some new jewelry. At the base was a barbell passing vertically through, with exposed metal spheres on either side. About an inch up was another, but this one oriented diagonally. An inch after that, a horizontal one. He tried not to break his stroke which meant he couldn’t examine himself carefully, but it felt like the pattern continued, barbells spiraling up his shaft, probably making two full turns.

And he did feel the pattern. Wow. His formerly smooth strokes were now punctuated every inch with a little more pressure, a little more friction, dancing down his cock on the “in” strokes and up his cock on the “outs”. He had to slow down to manage the pleasure.

Kelly seemed to like it, too. She went from grunting once per stroke to a more continual moan that rose and fell as each piercing entered her, almost like singing.

Paul kept going, savoring the interesting new sensations. And enjoying the view of Kelly spread out before him, tits gently jiggling on each thrust. He caressed her toned legs, sometimes lifting one up to kiss it.

Kelly was very clearly enjoying herself, barely verbal from the pleasure, but it seemed like she still wasn’t actually building towards an orgasm. Paul again prompted, “So, is this better than a toy?”

It took Kelly a moment to respond, and her response was just, “Toys… my clit.”

Oh, thought Paul. That’s super reasonable. I’ve heard that many women just don’t come from vaginal stimulation alone, and I’ve been doing nothing for her clit. So he maneuvered a hand down there to start stroking (it wasn’t trivial while still supporting her legs, yet he managed). But he was surprised to feel his hand bump against something else. She must have changed her fantasy again.

He looked down to see a strange new appendage coming out of his crotch. This was weird, but he kept up his pace while examining it. It emerged just above his cock and jutted forward about two inches, almost like a mini cock or giant clit. It was stiff but not too stiff, like an ear – he guessed it was made of cartilage. At its end it split and tapered into two flat points.

Its purpose was evident. It had bumped a hand questing for her clit because at the deepest part of each stroke, it rubbed up against Kelly’s clit. Then it clicked for Paul that he’d seen dildos, including the one he might have to buy Kelly, with just such a shape.

Paul figured that with a huge cock filling her completely, with piercings providing extra jolts of friction and pressure, and a built-in clit-tickler, he’d get her over the edge soon. But he wasn’t quite sure the best way to use his equipment. If he took long strokes her clit got just a momentary stimulation at the end of the stroke. He tried staying all the way in and sort of jiggling his hips around to stimulate her clit, but that didn’t do it for either of them. The best he found was short fast strokes, filling her and hitting her clit quickly and repeatedly, but by this point he was getting tired and his core just couldn’t keep up that pace.

Shit, he wondered, maybe a toy really is better than me for getting her off. He tried what he could think of. Different paces. Dirty talk. Shifting her legs around. Getting a hand down there to help with her clit. Nothing quite worked. He’d heard of guys who couldn’t come with women because they dicks were too used to the hard grip of masturbation. Maybe Kelly was so used to the hyperstimulation of purpose-built toys that even this ideal cock wasn’t enough for her.

As he tried a slightly different angle, he also wondered, does she remember the conversation we’ve been having? I ask her if I’m better than a toy, then she gives and answer but also changes her fantasy and my junk changes so that her answer no longer made sense. Is she experiencing the changes, or does she think I’ve always been like this? Other partners certainly didn’t remember changes, but does she really think it’s normal that I have a clit-tickler?

He pushed the wonders about his power aside. He had a job to do. Maybe she could help. He went back to staying deep inside her, trying to work over her clit by jiggling his strange new nubbin. And again he asked “Is this better than a toy?”

Kelly answered with a hint of frustration, “toys vibrate.” Then a look crossed her face. And then: holy shit.

Paul’s whole crotch started to vibrate. He didn’t know how, but boy did it feel good. He kept himself deep inside her, sending his vibrations all over her vagina and, crucially, onto her clit. This did it. After about thirty seconds of moans getting louder and faster, Kelly finally crested the wave and came hard. Relieved, and turned on seeing her spasm, Paul finally came too. It had been quite a build-up, and his orgasm was great, pushed along by her cunt squeezing down on him and the whole area still vibrating.

As their orgasms started to fade, the vibration turned a bit towards overstimulation. Paul wanted to be done with it, and then suddenly it stopped. Had he done that? He tried to start vibrating again by sort of… reaching out with his mind? Was it a bit like doing a kegel? Soon enough he started vibrating again, and he got the hang of turning his vibration on and off, mentally. Wow. Game changer.

After reveling in the afterglow a bit, once he figured they were both able to speak again, he asked. “So, was that better than a toy?”

Kelly hesitated. “Toys have less clean-up,” she offered, as they felt his cum oozing out of her hole.

Sheesh, she really wants to win this bet, Paul thought. But he said “not a problem”, pulled all the way out, got down on his knees, and started sucking his cum out of her. He didn’t mind – he knew his cum tasted great. He was careful not to overstimulate her, but obviously he did a bit of teasing with his tongue.

After a few minutes of that, when he thought he’d got it all, he asked yet again, “Was this not better than a toy in every way?”

She smirked and said “toys stay hard.” He stood up to reveal his rock hard boner. She grinned, evidently expecting that he’d get hard again while eating her out.

“May I?” he asked.

“Of course.” So he slid back in, slowly, savoring the feel of each barbell pushing into her, then mentally turned on his vibration and settled in.

***

After six more orgasms (four hers, two his) and three more positions, she said again “toys stay hard.” So he showed her that so did he.

***

A few more hours later she finally passed out. He found some paper on which to write his name and number, and saw himself out.

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