"I-- I-- it's hard to explain."
Alison squeezes on Jake's mini-cock and gives a small purr. "Oh, it's hard, alright." At 5'1" and probably no more than 100 pounds, Alison was a rather petite. Jake realized that her hands were no exception. With almost a whole half-inch of his cockhead spilling out over her tiny grip, Jake's cock looked almost normal -- comparatively speaking. His hips bucked with arousal as he burned with the dream of some day being big enough to be called "average".
Some day? He could just change it back tomorrow, yet a foggy confusion set over him. He could feel a small part of himself resigned to this size forever, and an even smaller part convincing itself that he was always this small. He DID shrink his penis to this size, right? Right?
Before that could go on any longer, Jake was pulled back to the moment as Alison started stroking his small shaft up and down that half-inch of room she had to work with. With her left arm wrapped like a vice around his waist, he could feel the rise and fall of her chest increase in pace, he could feel her heart racing almost as fast as his. Was-- was she enjoying this?
Alison's eyes were filled with hungry desire. He could feel her hot, heavy breaths pounding down his body. Then, at once, she dove her head onto his little dick, taking the whole thing into her mouth with one breath. Jake could feel her warm, wet lips wrap around his cock. His cock rode along her tongue, swishing across the sensitive nerves on the head of his penis, daring him to cum.
"Oh, god--" Jake moaned, willing himself to not be both a little-dicked loser and a premature ejaculator in front of his office crush.
Alison moaned with pleasure as she took him in her mouth. She had always suspected that Jake had always kept their flirting office-tame because he had a tiny dick, but his recent mention of a girlfriend and then today's little trouser show in the office had her worried that maybe he just wasn't that attracted to her. She'd been on a bit of a losing streak with asshole boyfriends, and had lost a great deal of self-confidence. When she spotted his car still in the parking lot, she decided to make a little gamble and ask him out for drinks. Seeing his little dick in his hands was more than she could have hoped for. She felt herself flush and the pulsing of a little bead of electricity somewhere in her gut. Him letting her take control drove her even more wild: this one wouldn't treat her the way those other guys have. She wouldn't let him, and he would obey.
"Oh-- please-- please--" Jake begged through moans of pleasure.
"Please what?" Alison asked without taking his little dick out of her mouth. She like that she could talk and suck him at the same time. It was cute. She giggled at the thought of giving a dissertation while blowing her cute little Jakey.
"Oh god, she's laughing at how pathetic I am," Jake thought. "I need to show her I am still a man."
Mustering what little bravado he had left, Jake tried to command her to stop sucking his cock and let him bend her over and fuck her tight little ass. Instead, he said, "f-fuck. me."
Alison stopped at the base of his cock when he said those words. The whole car froze. She knew that he was dating Katie. She'd met Katie. She liked Katie, or as much as you can like someone who is fucking the person you want to fuck. What they'd done so far could be pushed out of mind, probably, with enough thought. It didn't need to be mentioned ever again. But, somehow, fucking Jake would be something that she couldn't just pretend hadn't happened. Admittedly, because she'd already played out this next step in a dream or two. She took in a deep breath and slowly raised her head from his lap, letting his cock out of her mouth with a small (and cute) pop.
They both looked at each other. Terrified, yet determined. Alison swept her hips around and gracefully moved her leg across his, straddling him with her ass resting on the steering wheel. Jake reached down and fumbled around with the seat levers until his chairback awkwardly rocketed all the way down. The both gave out a nervous chuckle, which caused Alison's butt to bump into the steering wheel, making the car give out a little honk. They both froze, looking around the parking lot, and then broke into laughter again. Jake, regaining a little confidence in the moment, moved them both away from the wheel and then gave Alison's ass a playful little slap.
"Bad girl."
Alison gave out a mock gasp, and then slowly moved her right arm across her chest, down along her stomach, and rested it at the hemline of her dress. She pulled it up a couple of inches.
"Well then," she purred, pulling her dress up a little more to show her pussy lips, glistening with anticipation, "I guess I should stop then." She lowered her hips, hovering millimeters above Jake's aching cock. He could feel her heat, teasing his head.
"You-- you'd better not," Jake said, trying to wrestle back control.
Alison arched an eyebrow at this, ready to stomp down any signs of excessive machismo before it ruined her cute little Jakey. "Then beg me. Beg for it."
Without hesitation, Jake let out a desperate, crackled "PLEASE! Please fuck me!"
Alison lowered a quarter of an inch, teasing him with the touch of her lips. Jake buckled with surprise, barely holding back from cumming immediately. Alison smirked at this new-found power. He was hers to with as she pleased. She raised her hips. Jake tried to raise his to follow her, to plunge himself inside of her, but she slammed a hand down on his pelvis and gave a tsk-tsk-tsk.
"No no no, Jakey. Beg me to fuck your tiny cock. Beg me to pity fuck your itty-bitty dick." She bent down, placing her mouth against his ear, "I bet I wouldn't even feel your litle baby-dick," she whispered before giving his earlobe a playful bite and kiss.
Jake's willpower was entirely focused on not embarassing himself further and cumming before even entering Alison. He couldn't remember ever being this aroused. He also couldn't remember ever being any bigger than right now. He was pushing 3.3 inches. Maybe even a whole 3.5! A tiny voice in the back of his head was screaming something about a watch, but he didn't have the mental energy to focus on it.
"Please fuck me! Please fuck my tiny cock!" Jake breathed out.
"Louder. Really beg me for it."
"PLEASE FUCK MY ITTY-BITTY DICK!" Jake screamed.
Alison plunged down, taking "all three" inches at once. The shock of her immediacy and the sensation of her tight pussy gripping his little dick so tightly was too much for Jake. He strained, contorting the muscles in his face, but failed to hold back the tidal wave of--
*drip. drip*
Jake's whole body convulsed wildly as droplet after droplet squirted out.
For a moment, Alison was filled with shock and disgust. "Did you just cum inside me?" Then after realizing why she had to ask, she laughed with her whole body. "Ohmygod. You-- just-- aww, poor lil Jakey."
Humiliated and out of breath, "lil Jakey" felt his dick receding as it shriveled into a nub.
"I-- I'm normally not--"
"oh, shhh. This can be our *little* secret, Jakey. Maybe next time you'll make it all the way in."
"I, uh, that was all the way in. For me." Then, in a post-coital flash of insight, he remembered the watch -- that he wasn't always this small. "I'm not always this small! I can be bigger!"
Alison giggled at her little man and curled her finger around Jake's remaining inch. "Oh, I know sweetie. You were plenty big for that whole second you lasted, stud. Maybe we can do some training. Get you up to a whopping minute. Maybe even two."
Jake opened his mouth to argue about his size, and to explain about the watch, but he was distracted by an implication she dangled in front of him: "wait-- you want to do this again? Like- like multiple times again?"
Alison laughed at her desperate little man, already wanting more.
"Well, you gotta play your cards right there, big guy. We need to set some ground rules."