The Training of Jeff Stintum Ch. 19

"Uhhh," said Jeff, not wanting to admit that she was right.

"Soooo," continued Sarah, making eyebrows at him, "I guess we'll just have to make you bigger!"

"Make me...what?" Jeff was bamboozled.

"Bigger!" chirped Sarah, reaching into her nightstand drawer. She brought out a white roll of something...a tape measure. She let it fall, as she held the end with her thumb and finger, the rest of it unravelling onto the bed. Jeff swallowed, not knowing what to say.

"But first," said Sarah with mock formality, "we have to see how big you are now."

"I'm nine inches," blurted Jeff, who had been used to saying these words proudly. Now his voice sounded like he was trying to ward off an attack.

"Oh, Jeff!" laughed Sarah as she got the tape measure ready, "don't sell yourself short! I'm pretty sure you're longer than nine inches."

"But—but, I just measured myself a few weeks ago," protested Jeff. He didn't know why he was complaining, but he kept at it. "I couldn't have grown since then."

"No?" asked Sarah, arching her eyebrow quizzically at him, "I think you have, Jeff. I think you got bigger." She extended the tape measure out and brought it up to his cock. Jeff couldn't do anything to stop her.

"And," she said confidently, pulling the tape measure back suddenly before she could get a good reading, "I think it's because you've spent so much time around me." And once again she bowed her head down, arching her back, neck and torso in an riveting curve as she thrust her head down onto his cock, taking him to the balls. Jeff threw his head back as he gave a sharp intake of breath — this time, Sarah stayed down on him for a few moments, and Jeff shut his eyes and grit his teeth as he weathered her oral onslaught. He felt a relentless tug all down his length as her throat muscles constricted and swallowed around him, the inside of her cheeks squeezing and sucking and massaging the thick base of his cock. He felt her long tongue begin to slither around the base, and would've come if she hadn't thrown off her head with a loud smack as her tongue unslithered from his length.

"Perfect time to measure!" she said brightly, and she carefully held up the tape measure to his throbbing, painfully erect length. She started with the "0" at his base and slowly drew the tape measure up. 3, 4, 5, 6...Jeff had never been measured by someone else before. He looked at Sarah's long fingers carefully drawing the tape measure along his length, at her sharp red fingernails gingerly extending it out, and he felt utterly objectified...a piece of meat. Much to his own pleasure and frustration, this feeling seemed to make him even harder still.

7, 8...Sarah was going slower now, exquisitely drawing out the conclusion. 9...she was right — he was longer. Jeff felt a lump form in his throat as Sarah turned around to look at him, giving him a wide-eyed stare as as her eyebrows went up suggestively, as if to say 'I told you so!' She turned back and kept going. Jeff's eyes nearly popped out of his head as he saw the double-digit 10 unfurl...and still it wasn't enough...Sarah kept going...the twin legs of the 11 started to form...was it possible?? Could he really...and then she reached the tip.

Sarah peered down carefully to read the measurement. Jeff's heart pounded in his chest.

"Wow!" said Sarah, clearly impressed. "10.75 inches!" She turned again to look at him, the color even visibly coming into her face as well. "That's...that's amazing, Jeff!" She wasn't even flirting with him anymore — she was genuinely astounded at how big he was. Almost in a semi-conscious, mesmerized state, she went down on him again, her eyes unfocused, as she took him completely in her throat again. It was almost as if she was making sure she wasn't dreaming. She came off him again, panting.

"I just — wow Jeff," she said, out of breath, "I just don't understand how someone so small," and here she pinched his upper arm lightly with her fingers, "could be so huge down there." Without wasting any more time, she wrapped the tape measure around the base of his cock where he was thickest. Her mouth dropped open.

"7.2??" she said in disbelief. "7.2, Jeff?!?" She turned and looked at him, her eyes wide, her mouth open. "Jeff." She cocked her head. "Your cock is enormous!" Jeff's face was burning in a mixture of pride and arousal. He had no idea he was so big...he was also not prepared for the expression Sarah was making. She looked legitimately shocked and impressed — he hadn't seen her so caught off-guard before. She turned her head back to his cock, reached out, grabbed it, and shook it vigorously.

"How about that," she growled, almost to herself, "I can basically deepthroat 11 inches." She turned back to Jeff, a twinkle in her eye. She was back in control. "But Jeff," she said, shaking her head slowly back and forth at him, "it isn't enough. I wanna struggle. I wanna strain to fit it all in." For the final time that night, Sarah turned and swallowed up his cock, humming aggressively, shaking her head back and forth as she took him all the way in again. Jeff gasped out and felt the cum boil in his balls. Sensing his orgasm, Sarah reached out her long nails and tickled Jeff's balls lightly, coaxing the cum from them. Jeff whined as he felt the cum shoot up his shaft, defying gravity, as it responded to the animal shakes of Sarah's head, the insistent pull of her throat, and the ruthless vacuum of her cheeks.

"Aaaaaughh!" he cried, throwing his arms up involuntarily in the air, his entire body convulsing as he shot cum deep into her throat.

"Mmmrrrrgghh!" snarled Sarah aggressively through the base of his dick, mashing her face further into his abdomen as she swallowed his cock as far down her throat as she possibly could, as if to show him how much more she could go down on him if he had been bigger. The bedroom was full of Jeff's whines and squeals as Sarah swallowed deep in her throat over and over, bowing her neck up and down in a lewd, graceful curve with each swallow.

After a minute or so, she had milked him completely dry, and released him with an exaggerated "pop!" as she turned back to look at him, showing him her open mouth and flicking her long tongue back and forth at him obscenely.

"See Jeff?" she said, pointing a long manicured finger down her throat, "you may be big, but you're not big enough for this throat."

Jeff was still out of breath, and his entire body was red and glistening from perspiration. Still, though, he managed to feel affronted. What did she mean, he wasn't big enough?

"I bet I could throat at least another inch," said Sarah dirtily, sticking her finger all the way down her throat. "I bet I could deepthroat a twelve-inch cock, even one as thick as yours." She faced Jeff intensely, the sea green of her eyes blazing . "Only one way to find out." She turned back to her nightstand and opened the drawer. A moment later she had brought out something...something long and black...Jeff's stomach twisted in anxiety. What was this?

Sarah held it up to his face, shaking it slightly so that it wobbled back and forth in her hand. It looked like a long ribbed rubber tube.

"W-what's that?" asked Jeff.

"Ever heard of sounding, Jeff?" asked Sarah, smiling down at him. She was clearly excited.

"Uhhh...no," said Jeff.

"Urethral insertion?" ventured Sarah playfully, her eyebrow arching again.

"Errrr...maybe," said Jeff. The phrase rang some kind of bell with him. Though he didn't realize it, the reason why was because he had come across some hentai a year or so ago that he had watched before moving onto something else, uncomfortable with how it made him feel.

"Well," said Sarah, holding the rubber tube up to his cock, "this is a very special kind of sound, Jeff. Most of them are made of metal, but —" and her eyes bore down intently on Jeff "—you can't sleep with the metal ones in your cock."

"S-sleep...w-with, that...?"

"In your cock, yes," said Sarah.

"N-no way," said Jeff bluntly.

"Oh!" said Sarah immediately, "so you're not interested in getting any bigger for me, huh?"

"Uhhhh," said Jeff. Of course he wanted to get bigger for her. Somewhere in the back of his mind, he felt like all he had going for himself was his cock. Sarah sure did appreciate it...and he hated the thought of her getting...bored because his dick didn't pose a challenge for her.

"Is, uh..." he started to ask.

"Yes," asked Sarah patiently, twisting the rubber sound around in her fingers.

"Is...that thing going to, uh...going to make me bigger?"

She gave him a smile as she shrugged her shoulders. "It's worked before."

"B-before?" he asked. "You mean...you mean you've tried th-this thing on other—"

"Guys before, yes," said Sarah calmly. It wasn't entirely true. She had a few smaller sounds in her nightstand drawer that she had previously used, to great effect. But this was the first time she had used this one.

"How...how many other guys?" asked Jeff, feeling increasingly bewildered. Sarah reached out her hand and lovingly wrapped it around one of his thighs, marveling at how far around it she could go. She started to gently, insistently, knead him.

"That's not important right now," she said smoothly. "What is important is the choice you have: do you want to try it or not?"

Jeff looked at the long, black, flexible tube in Sarah's fingers. It had a sort of rounded head on one end, and was ribbed with raised patterns along its length. As Sarah moved it around lightly in her fingers, he could also see that it was hollow. He was nervous...was that thing even going to fit in his dick? And what would it feel like? He looked up at Sarah, trying without success to ignore her powerfully kneading hand on his thigh.

"It'll make me bigger?" he asked again. Sarah closed her eyes and nodded slowly. He looked back at it. Sarah's fingers were twisting it around, around, around...

"O-ok," he croaked. Sarah's fingers stopped twisting and her hand stopped kneading.

"Good, Jeff!" she said brightly. "I'm excited! Aren't you?"

"S-sure," he lied, feeling more scared than anything else.

"Ok, will let's put it in, shall we?" Sarah reached down and took his still-erect cock in her hand. Jeff flinched.

"Easy, easy," said Sarah softly. Her thumb and forefinger gently pinched the purple head of his cock, making it yawn open. She brought the end of the sound with the rounded head close to the opening. Her mouth was slightly open in concentration and suspense...she turned to look back at Jeff, as if to share a glance with him during this intimate, intense moment. Then she gently, smoothly, navigated the rounded head into Jeff's peehole. It took about half a minute, as she was very careful and very deliberate...she wasn't rushing it at all. But there it was! It had fit in completely. To Jeff it did not feel as unpleasant as he had thought. And with Sarah as the one navigating the sound into his cock, it was actually quite stimulating. Despite having recently cum, his cock seemed to stiffen even more.

"Good," cooed Sarah down at his dick as the head of the sound went all the way in. She took the hollow tube in her hand and twirled it slowly around. He gasped at the intensity...she was literally teasing the inside of his cock. His member responded accordingly, the blood rushing into it as it experienced this kind of inner stimulation for the first time.

"And now, we go all the way in," said Sarah softly, guiding Jeff lovingly step by step. She gently pushed the sound down further into his cock, twisting it gently the whole time to ensure that Jeff remained stimulated throughout. Jeff was barely cognizant of a slight trickle that he felt on his left side, but he was in no state of mind to notice other things happening around him. He was only focused on the sound going deeper and deeper into his cock...it was searingly pleasurable. It was like with every gentle push, Sarah was drawing out his soul from his cock.

He didn't realize it, but the trickle of liquid he felt was Sarah's cum. Right after the head of the sound disappeared into Jeff's cock, she had not been able to contain herself any longer and had gushed out onto her sheets. Jeff was laying with her in the deep indent that her huge body had made on the mattress, and her cum was pooling around him. She fed the sound further into his dick, inch by inch, as she continued to have little aftershock orgasms...this was almost too much for her. She wished it could go on forever, which was one reason why she made sure to take her time.

After a few minutes, the sound was almost completely inside. There was a little black tip, about a quarter of an inch long that still protruded from Jeff's cock, but the rest was inside. Jeff had felt the head bump into the base of his cock from the inside, and he had nearly come again, so intense was the pleasure and the overstimulation. His cock felt like it was being spit-roasted alive.

Sarah sat back and lightly flicked the protruding tip with her finger, sending impossible vibrations of pleasure down his length. Jeff did orgasm this time, although it was completely dry. Sarah saw him twist and convulse and chuckled softly as she bent down and engulfed his mouth in a powerful, soft, luscious kiss. She released him and directed his glance to his cock. There it was, stuffed by the sound, looking massive.

"Well?" asked Sarah, "how does it feel?"

"It feels — it feels...amazing," panted Jeff, still overwhelmed with sensation. And it did feel amazing, although the extent to which his cock was stretched almost felt like too much.

"Good, Jeff," said Sarah. "It'll take some getting used to, but the first step is always the hardest, right?"

"R-right," said Jeff.

"Now," said Sarah, turning him around to face her completely, "I want to add one more rule. Can you follow it, Jeff?"

"Y-yes," said Jeff.

"Can you name the other rules first?" asked Sarah cooly.

Jeff panicked for a moment at having been put on the spot. But he recovered quickly. "Uhh...uhh...use the crutches at all times!"

"Right," said Sarah. "And?"

"Ummm...uhhh...no smoking!!" said Jeff.

"Yes," purred Sarah. "And?"

"No drinking unless it's with you," finished Jeff triumphantly. Sarah smiled widely.

"Gooodddd Jeff! High five!" And Jeff smacked her outspread hand, trying and failing to ignore how absurd his tiny hand looked high-fiving hers.

"Now, this is the fourth rule: you will always have this sound" — and she tapped the head again, causing Jeff to spasm — "in your cock. Unless I take it out. That's the only way it'll really be able to work its magic and stretch you out. Can you agree to that, Jeff?"

"Yes," said Jeff, trying not to think too hard about what he was agreeing to. He felt his eyelids get heavy. His orgasms had caught up with him — he was exhausted.

"Good, Jeff," said Sarah again, taking him up in her arms and squeezing him tightly. "Good! Now it can really start." She gave him another kiss and then leaned over, turning off the light. She twisted her huge body back around in the darkness, putting one of her arms around Jeff's torso as she held him to her close, spooning him. Jeff felt swallowed by her body, and vaguely realized that he was about to fall asleep in a sticky puddle of her cum. But he didn't care anymore...he was too tired, and abandoned himself to Sarah, feeling totally cozy. One final thing still ate at him, however.

"The...the start of what, Sarah?" She squeezed him to her even tighter as his hair ruffled and he smelled the sweet scent of her exhale. He could feel her smiling in the dark.

"Your training, Jeff."