Date: Tue, 09 Jun 2009 15:04:52 -0700 From: pm1954@hushmail.com Subject: Jake and the Sissy The following story is set in the wonderful "Sissyboy" world invented by beautifulcreamer. JAKE AND THE SISSY "Well then, I guess we're through, babe" Jake hung up the phone with a smirk. He'd just ended it with his latest, and possibly last, girlfriend. Having run through all the decent looking chicks at his high school, it was time to move-on. "Honey, do the other foot, would you?" "Sure, Jake!" chirped the ten-year-old angel at Jakes feet, who was giving him a nice foot massage. Timmy was a golden-haired, doe-eyed sissyboy, who worshiped the ground Jake walked on. And Jake had plans for him. Six months prior, Jake's next-door-neighbor lady had come to his door with a problem. She was worried about Timmy turning out to be what he was so clearly meant to be: a man-pleasing little sissy. With the age of consent lowered to eleven, it wouldn't be long before a platoon of horny men would be after him, and his mother wanted to make sure they didn't turn him into "one of those." "He needs a man's influence, Jacob, a big brother to show him how to be a real man; like you." This appeal to Jake's vanity was not wasted. As star quarterback and captain of the wrestling team, Jake was a stud, and knew it. His mop of black curls, dazzling smile and muscular body made him the idol of every guy his age, and the fantasy of every girl. And Jake was not above using his assets to nail every horny female he wanted. The trouble of course (as so many men have found) was that, after they spread their legs, those same girls started to become manipulative users, parlaying the one thing they had to give into a lifetime of servitude. That wasn't for Jake. So as soon the the games began, Jake made his exit. The trouble with that was, the supply of pussy was limited, and he was running out. Enter Timmy. Jake took-on Timmy's "training" enthusiastically, letting the kid hang out with him, teaching him how to behave in a less sissified manner, coaching him on weightlifting, showing him how to dress like a regular guy. And it paid off. At school, Timmy had gone from a picked-on cry-baby to, if not one-of-the-guys, at least no longer objectionable. And was his mother grateful! What she didn't know was that in private, Jake was training Timmy in a very different direction. He let him know from the first day that he was a sissyboy, and that nothing would ever change that. And he explained a sissyboy's function: to give pleasure to real men like Jake. He also allowed the boy to be himself whenever they were alone together, which was every day after school for several hours. He was even allowed to dress how he pleased. In fact, Jake purchased several pairs of pink panties for the boy to wear while with him, which Timmy adored. As he watched Timmy lovingly rub his feet, Jake considered the situation. There were only three months left of high school. In the fall he was starting at the university in town on a full athletic scholarship, and would be continuing to live here in the apartment above his dad's garage. There would be no time, and no need, for him to work, in order to afford a girlfriend. Not when he had prepared such a fine alternative. No old fucker with lots of money was going to steal this sweet baby away from him; he'd seen to that. He'd treated the kid so well, the boy was head-over-heels for Jake. Jake sighed with satisfaction. It was all working out perfectly. Now, it was time to take Timmy's training to the next level. "Come up here, baby." Timmy scrambled up and lay beside Jake on his bed. Jake wrapped his big arm around the boy's shoulders and whispered into his ear. "Your body is getting to be so beautiful, honey." Jake played with the puffy pink nipples on Timmy's chest, causing the boy to sigh and moan a bit. The weightlifting had given him a fine pair of firm titties. Jake sucked one of the delectable nuggets into his mouth and nibbled at it, causing Timmy to groan and his tiny cockette to stiffen in his panties. "Looks like someone likes having his titties sucked," said Jake. "Slip those panties off, babe." Timmy did, revealing his little boner. "What's that called, honey?" "My peenie." "That's right. Sissyboys have peenies. Men have cocks. It looks like you need to have boys-time, baby." Timmy clapped his hands and shouted "Yay!" as he pulled a small pink vibrator out of the nightstand. Bringing it to his mouth, he sucked on it, wetting it all over with his spit. Then he raised his legs and pushed the girly device into his bottom, with a satisfied sigh. "That's right, honey. Play with your boy-pussy for me." Jake loved watching the horny little prick-pleaser pleasure himself this way. Rising from the bed, he stripped off his shirt and began to flex his muscles for the boy. Nothing turned Timmy on like the sight of Jake's hot, ripped physique. Jake brought his bicep to his mouth and kissed and licked it in narcissistic self-worship. Timmy gasped, and turned the vibrator on, thrusting it more frantically into his boygina. Looking down at Timmy lustfully, Jake began to slide his shorts down, revealing the overstuffed jockstrap beneath. Swaggering to the bed, he placed his thighs on either side of the boy's head, rubbing the fragrant pouch on his face. Timmy nearly swooned from the powerful pheromones that assaulted his senses. Taking Timmy's hands away from the vibrator, Jake began sliding the sex-toy slowly in and out of the hot hole, carefully avoiding Timmy's overexcited "boy's place." He didn't wantr to send the cherub to heaven just yet. No, this time they were going to go there together. After a minute of this exquisite torture, Jake changed his position again, so he was staring into the lovely boy's eyes. "Timmy; are you ready to go all the way? To be my little sissy? Do you want me to make love to you?" "Yes, please," the boy said softly. Jake stood and slowwly pulled the jock down over his straining shaft, which snapped up against his rippling belly, revealing the huge balls beneath. Timmy gasped. "That's a man's cock, sweetie." Standing over the boy like a conquering hero, Jake hit a series of bodybuilder's poses, revealing himself in his full glory to the boy for the first time. Timmy stared up in awe-struck amazement, wimpering softly. Kneeling before Timmy, Jake pushed the boy's legs back until his pink rosebud was open exposed. He panted with lust as he eyed the perfect, virgin hole. Drops of moisture clung to the wrinkles. He brought his tongue to the crevice and began to lick. Timmy squirmed, as if trying to escape the onslaught of sensations, but Jake held him firmly in place. His tongue slipped into the furnace-hot interior, and the musk of Timmy's excitement filled his senses. "Holy crap!" Jake thought. "It's a good thing I didn't know how this would taste, or I'd never have been able to hold-off." When he thougt of all the nasty, fishy cunts he'ds been forced to eat before he could get any action, it made him so pissed. All that time, he could have had this! Well, it was his now. Pulling his face out of Timmy's crack, he plunged his tongue into the perfect little boy's mouth. Timmy groaned and threw his little arms around Jake's bull neck. He ground his satiny smooth body against Jake's muscles, in a frenzy of need; for what, he didnt' quite know, but he was about to find out. Jake pulled a new tube of Spermbutt lubricant from under the bed. He'd been saving it for this moment. He covered his throbbing organ with a generous coating, and added a dollop to Timmy's little hole. "Okay, baby; this is it. There's no going back after this. Do you want me to fuck your little ass and turn your hole into a pussy? A soft, warm, wet, open pussy, for me to fuck whenever I want?" "Y-y-yes...!" Timmy stuttered. He wanted it more than he had ever wanted anything, but he was also scared of the huge cock, and the powerful lust in Jake's eyes. "All right then. Here we go." Jaked pushed the plum-like head of his cock through the outer sphincters with no hesitation, clamping his mouth over Timmy's to stifle the inevitable scream. He kept it there until the cries turned to moans, and Timmy began to squirm again, asking for more. Letting his bodyweight provide the pressure, Jake forced inch after inch into Timmy in a slow, smooth slide to complete penetration. When he was ball's-deep, he raised his torso. "Look down, baby." Timmy looked and saw that the massive intruder was all the way inside him. He was joined to Jake completely now, and his sissyish heart leapt up. Jake flexed his cock in Timmy's bowels, and delicious sensations ran through the boy, causing him to blurt-out: "Oh, yes! Fuck me, Jake! Fuck my pussy!" Jake laughed, delighted by his complete conquest of the boy. Never one to turn down a request like that, he began to piston the massive inseminator back and forth, pulling out until only the fat head remained within, then ramming it back inside, so his huge balls slapped against the smooth upturned asscheeks. Turning his head, he watched the mating in the mirror on the wall opposite his bed. "This is the hottest thing ever!" he thought, as the picture of the muscular teen taking his pleasure with the innocent boy burned into his brain. His lust boiled over and he threw his head back and howled: "Fuck yeah! Gonna breed this tight little hole! Turn it into a cunt! You're my bitch now, Timmy!" As Jake pushed past his "boy's place" inside his no-longer-virgin pussy, over and over, Timmy felt an orgasm bilding, but one so much bigger than he had ever achieved with that silly piece of plastic. His moans grew louder and louder, until his eyes rolled back in his head and his body was racked with spasms. Jake felt a rippling around his cock, and cried: 'Aw, shit! You're milking me!" Unable to hold back, he blasted his thick goo deep into Timmy, more and more, until he thought he would die from the pleasure. A few minutes later, both boys had returned to Earth. Jake moved Timmy into a spoon position, and softly explained how things would be from now on. Untill Timmy's birthday, they would keep this part of their relationship on the downlow. Once Timmy was eleven, there was nothing his mother could do about it, and they could live openly as one more man-boy couple in this brave new world. Timmy sighed with contentment. "I love you so much, Jake." "I love you too, honey," Jake replied, and suddenly realized...he did.