The Babysitter�s Initiation

by Michael K. Smith



At twelve, Jason had reached the age where he resented being babysat. Even the term "BABY-sitter" offended him. He insisted he was perfectly capable of taking care of himself. And his mother bought it — most of the time.

"Dear," she said patiently that Thursday evening, "if I were just going to be gone for the evening, I would leave you here by yourself without a second thought. But your grandmother needs me, so I�ll have to be gone for the entire weekend, and that�s different. You�ll have to have a sitter, and that�s that."

Jason sighed. He knew that tone, which meant his mother had taken a stand and would not be swayed. Further argument would just irritate her, and he would pay for it later. A year ago, all this wouldn�t have been a problem. Patricia, his older sister, would have been here to keep an eye on things. But now Pat was a freshman in college, far away from home, and it was just him and his mom.

He sighed again. "Okay, okay. Who is it, anyway?"

She smiled, pleased he had abandoned the contest. "I�ve asked Liz to come over. I can certainly trust her, don�t you think?"

Liz was one of his sister�s best friends, also just out of high school, but she was working for a year and taking a couple of courses at the community college to try to get her grades up before she ventured off to college. Yeah, he had known Liz forever; she was okay. At least, she probably wouldn�t be the drill-sergeant.

Jason had soccer practice after school on Fridays, so he had already said goodbye to his mother that morning. When his coach dropped him off at dusk at the bottom of his driveway, it was Liz who opened the front door and waved.

He studied her as he hiked up the driveway. Liz was nineteen, like Pat, but where his sister was serious and intent on her future, Liz was bouncy, with a quirky sense of humor. Liz and his sister had always seemed like an odd pair, but they�d been close buddies since First Grade. For some reason, over her jeans and lacy blouse, Liz was wearing one of her mother�s old Christmas-themed aprons.

He looked her up and down as he reached the porch. "You look like June Cleaver." He was a fan of ancient television.

Even in flat-soled sandals, she was six inches taller than he was, and she reached out and ruffled his straggly blonde hair. "Okay, Beaver, how was practice?"

"Okay. I�m getting better at tackling, even though we really aren�t supposed to do that." He dropped his gym bag and his books, then eyed the apron again. "Are you fixing supper, or what?"

"No, tonight is pizza delivery. I�ll fry some chicken tomorrow, though. The apron was just an attempt to appear mom-like when you got home." She grinned and folded her arms. "You gonna get a shower before we eat?"

"Absolutely! I can�t even stand to smell myself after practice." Jason headed down the hall to his bedroom, hauling off his shirt on the way. Then he realized he couldn�t strip off the rest of his gear and head for the hall bathroom in his underwear, as he usually did — not in front of Liz. He went directly there instead, closed the door, and turned on the hot water. Then he stripped, tossed everything in the hamper, climbed over the side of the tub, and began lathering up under the needle-spray.

He was humming to himself when he finished, thinking about nothing in particular as he hung up his washcloth and turned off the water, so when he pushed back the curtain and saw Liz sitting on the closed lid of the toilet, he jumped. She was watching attentively, leaning back against the tank, one leg crossed over the other.

"Fuck! What do you want?" He fumbled for the curtain, trying to cover himself.

Liz smiled and shrugged. "Just came in to see the show. I haven�t seen you naked since you were three, and I was curious." She folded her hands in her lap. "Don�t worry about it, Jason — I�ve seen undressed boys before, you know. And if it makes you feel any better, you look very nice. All muscle-y and everything." She wagged her eyebrows up and down.

"C�mon out, now," she coaxed, standing up and pulling the thick bath towel off the rack on the wall.

Jason hesitated; he had no idea, really, what was going on here. But he couldn�t deny that having Liz — who was unquestionably a very pretty girl — watching him like this was kind of exciting. After a moment, he decided not to be a coward and stepped out of the tub, hands at his sides.

Liz shook out the towel, draped it over his head, and began drying his hair. Then, as he combed his fingers back through it, she sat down again and began wiping the water droplets from his chest and flat abdomen.

"Yes, you look very nice, Jason. You�re a very cute boy, you know that?" She grinned up at him, then glanced down his body. "Nicely built, too." He felt a faint stirring at his crotch.

"Oooooh, that got your attention, didn�t it?" And she reached out and wrapped her long, slender fingers around his penis.

At twelve, Jason certainly was aware of girls, but he wasn�t entirely sure what he was supposed to do about them. This was something he and his friends talked about all the time, all of them pretending to a great deal more sexual experience than they actually had — all of them frequently lying through their teeth, for that matter. And all of them aware of their mutual deception, too, if they were to be honest about it.

Jason had kissed two girls, once each — one at a party, one in the stacks at the library. Both kisses had been interesting but brief, and he knew he would want to do that again. But he had never touched a girl in an intimate way, or been touched, and the whole thing was a bit unsettling. What exactly did Liz expect him to do now?

She apparently was aware of his shock. "I�m not going to hurt you, okay? In fact, I would think you�d be enjoying this." She squeezed the shaft lightly and stretched it toward her, which sent little sparks through his legs and feet. And his cock was definitely reacting, increasing its length and girth with no conscious thought on his part. Then Liz slipped her other hand between his legs and cupped his balls in her warm palm. More sparks.

"Mmmm. . . . Jason, there�s something about an innocent young cock that I find very exciting. That�s probably perverted, but who cares, right?" She licked her lips as her respiration increased. "In fact---"

Suddenly, Liz was on her knees on the bath mat, her face very close indeed to his crotch. His cock already had become hard and stiff, and every time she moved it, he could feel it twanging like a banjo string. Then she took a deep breath, glanced up at his astonished face, and sucked him into her mouth in a single gulp.

Jason thought for an instant that he was going to faint right there in the bathroom. Her tongue was moving around and around his shaft, creating an incredible electrical current and making his knees tremble. She let it slide out of her mouth and tilted it upward so she could lick up and down the underside, head to balls. He groaned involuntarily.

"You like that? Hmmm? You like for me to suck your cock, Jason? You like to feel my tongue on your penis, don�t you? I like the taste of you, too," she murmured, though he could barely hear her over the roaring in his ears. She swabbed his balls, then left a wet track back up the length of the shaft, and let it slide deep into her mouth. She moved her hands around his hips and spread her fingers over his ass, pulling him closer until Jason swore he could feel his penis poking her tonsils. She was deep-throating him, taking him completely into her, pressing her lips into his still sparse pubic hair at the very base of his shaft. The sensation was amazing and it was making him very lightheaded.

Liz was moving up and down her mouthful of flesh, now, and rhythmically squeezing his cheeks. Jason�s hands were wound in her hair, as much to support himself against her onslaught as to provide guidance. His mind was filled with brilliant flashes of light, pulsing every time she changed direction.

On top of all that, he loved the feel of her hands caressing his ass. A flash of memory hit him: Must have been when he was five or six, he had invaded his adolescent sister�s closet and poked into her private stuff, and Pat and her friend Liz had caught him at it. They�d promised to rat him out to his mother, threatened him with violence, graphically described — had frightened the crap out of him, actually — but had promised to let it go if he allowed them to punish him themselves, then and there, using what they claimed would be his mother�s method.

So the two girls had pulled his pants down and Jason had laid himself over his sister�s lap and they had each taken a turn spanking his bare bottom. Pat had been wearing shorts, he remembered that, and his little penis had been trapped between his stomach and Pat�s bare thigh. The spanking really hadn�t hurt much, he remembered that, too. The girls had seemed to enjoy the process too much to concentrate on inflicting pain. One of them, maybe both of them, had stroked his bottom and slipped a few fingers down between his legs. He�d had strange feelings about it all at the time but hadn�t known what they were.

The memory of his little-boy ass being subject to a girl�s soft hand on that previous occasion caused a dramatic increase in the tingling that had begun building up in the pit of his stomach. He thought he knew what was about to happen, and he tried to pull himself out of Liz�s pistoning mouth, but she wouldn�t give him up. In fact, she clenched his cheeks even tighter and sucked even harder on his cock.

Then, one of her fingernails pressed sharply into the tender flesh very near to his asshole and that was all it took. Jerking and gasping, knees shaking, he came with an intensity he hadn�t known was possible. It felt almost like he was peeing into her mouth, and that made him jerk again.

Liz was gasping, too, and gulping and swallowing, but she was still sucking at him like she meant to peel the skin right off his erection. Finally, she let his deflating penis slip out from between her swollen lips and tried to catch her breath as she beamed up at him.

"There, now, wasn�t that nice?" she panted. She allowed a thin trickle of semen to ooze from the corner of her mouth as Jason watched in dazed fascination. Moving slowly and carefully, she got herself back up on the toilet seat as Jason untangled his hands from her hair. "That was a first for you, I�ll bet, wasn�t it?"

Jason nodded, then cleared his throat. "Yeah, I liked that. I mean, that was, uh, really something," he amended lamely. He was suddenly conscious of his nakedness — which was a little odd, considering what had just happened.

"So, um, like, now what?"

She raised her eyebrows and cocked her head at him. "What do you mean, �now what�, Jason?"

"Well, are we going to, um, . . ." He gestured vaguely.

"Oh. Are we going to fuck, do you mean?" He nodded dumbly. "No, baby, I don�t think you�re ready for that yet. Not with me, anyway. Besides," she added, "I doubt very much that you have a stash of condoms in your sock drawer — and if there�s anything I don�t need, it�s getting knocked up by a twelve-year-old boy. No offense," she added with a wink.

"But you know what?" she said as she stood up and carefully wiped the corner of her mouth with his bath towel. "Nothing says we can�t still have some fun. Right? How does �naked pizza� sound?"

Jason was somehow getting used to being shocked and startled, so he merely sat, still naked, on the living room sofa and stared while Liz strolled back and forth, unbuttoning her top with one hand while she talked to Domino�s on the cordless phone. She clicked it off and set it on the coffee table before turning to him with a smile.

"Here it comes, Jason!" And she threw her blouse back off her shoulders to reveal a demi-cup bra. Jason blinked but said nothing. "Not impressed, huh?" She put her hands behind her back. "Okay, . . . here they both come, then!" And the bra joined the blouse on the sofa.

This was another first for him, he thought. He could get used to this sort of education. Liz�s breasts weren�t overly large but they seemed full and firm, jiggling and swaying a little each time she moved. His cock was beginning to stir again.

Then she glided to the sofa and bent forward over him, bracing her arms on the back of the couch. Her breasts swung invitingly before his face, and he reached up to stroke their undersides with his fingertips, running his thumbs over her pink nipples.

"Ummmm, . . . do that some more, please, Jason." She moved closer. "Suck my tits, baby." He scrunched down a bit and guided the rosy tip of one breast into his mouth, catching the nipple between his teeth and brushing it with his tongue.

Liz shivered. "Wow — where�d you learn to do that? Feels so nice, Jason, keep doing that. . . ." So he sucked more of her breast into his mouth, enjoying the soft texture and the compressibility of her flesh. He lifted her other breast in his hand and carefully pinched the nipple, and Liz twitched and moaned in the back of her throat. His penis was undergoing a rapid resurrection.

Liz had straddled his lap and pressed her tits into his face and he was trying to give equal time to both. His cock was rock hard again, now, and pressing against the crotch of her jeans. And then the doorbell rang.

"Pizza man!" Liz jumped up with a laugh. "Jason, get behind the drapes over there, out of sight of the door."

The front door opened toward him and from his place of concealment, Jason watched as Liz, still bare-breasted, opened the door to accept delivery. He grinned silently as the delivery guy�s jaw dropped and his ballpoint clattered on the porch. Liz handed him a couple of bills, told him to keep the change, and flashed him a brilliant smile as she closed the door.

"Okay, what�s he doing now?" Liz giggled. Jason peered out the window.

"Well, he�s standing there staring at the door. Now he�s looking at his car. Now his watch. Now the door again. I think, . . . no, he decided not to ring the bell again. Okay, he�s getting back in his car, but he doesn�t seem to be in a hurry to leave."

Liz was laughing as she stood behind him at the window, as she pressed her nipples into his shoulder blades, and slipped her hands around his waist to take possession again of his cock. Jason felt slightly sorry for the pizza guy. He wondered if this sort of thing happened to him often.

"Well, I said �naked pizza�, didn�t I?" Liz turned him around and led him by the cock again back to the sofa. "And �naked� it will be!" She released him and unbuttoned the front of her jeans, then slipped off her sandals. "You want to do this, baby?"

It was Jason�s turn to kneel as he slid her zipper open and worked the jeans down over her hips, admiring the flat muscles of her stomach and the thick patch of soft hair. An enticing aroma rose from the crotch of her white panties. He pushed the jeans down to her ankles and she balanced herself with her hands on his shoulders as she stepped out of them.

"Now take my panties off quick, Jason," she whispered. "The pizza�s gonna get cold." He hooked his fingers in the elastic at the sides and she wiggled her hips as he drew the white cotton down, as well.

She rotated and presented him with her firm, compact bottom. "Your turn, baby: Kiss my ass, please." He was thoroughly enjoying the game, and he spread her cheeks with his hands and planted a wet kiss an inch above her asshole.

Then they sat side-by-side on the sofa with the bath towel spread across their laps to protect themselves from melted cheese, and the pizza never had a chance.

It was a very interesting evening, one Jason was sure he would never forget. After supper, with the empty pizza box stuffed in the trash can, Liz introduced him to reverse strip poker. Instead of removing an article of clothing each time you lost a hand, you put one on. And she insisted they each had to dress the other, so Jason struggled with the back on the back of her bra — "A valuable skill," she insisted — while Liz made a point of putting his briefs on him backwards, just to see his expression.

When the clock in the study chimed eleven, Liz stretched and made a creaking noise. "Jason, I think it�s time for you to go beddy-bye, right? Don�t want your mother to think I�m encouraging you to develop bad habits, now, do we?" She winked at him as he gathered up his clothes. At the moment, he was wearing a pair of denim shorts but no shirt. Liz was similarly semi-attired, breasts swaying as she picked up her bra and top. Then she took his hand and led him up the stairs.

At the top, Jason turned to his left, toward his own room, but Liz held on to his hand.

"And where do you think you�re going, young man?" She led him the other way but passed the guest bedroom, where he had assumed she would sleep, and went on instead toward the big bedroom, his mother�s room. "You�re not going to let me spend the night all alone, are you?"

She wants me to sleep with her, he thought. I�m going to sleep with a woman, both of us in one bed, all night long. He could think of no reason to protest.

His mother�s bed was Queen-sized, with a thickly quilted white comforter spread across it and table lamps on each side; one table held a clock-radio, the other a phone. A modest portable TV stood on a stand opposite the foot of the bed. It was a cheerful room and the younger Jason had spent many afternoons here in deep conversations with his mother while she folded laundry. His father had left when he was little and he didn�t really remember much about him. It had always just been his mother, his sister, and him.

Since he�d gotten a bit older, though, he hadn�t come in here much, not even to snoop. Hanging around your mother�s bedroom didn�t seem like the kind of thing a grown boy should do. In any case, he hadn�t been under the covers of his mother�s bed since Kindergarten — and certainly never with a girl. He wasn�t sure whether he was dismayed, or excited, or a little of both.

Liz dropped her shorts and panties on a chair and fluffed up her pubic hair with the fingers of one hand. "You don�t need jammies, do you, Jason?"

He shucked his shorts and briefs and dropped them on top of hers. "Isn�t it kind of late for that?" He was proud of being able to think up a snappy comeback so quickly. Liz had had the upper hand all evening.

"Do you have to pee before bed?" She glanced at the master bath.

"Girls pee. Boys piss."

"Oh, excuse me, sir," she laughed. "But you�d better empty your tank, okay?" She raised an eyebrow. "In fact---" She stepped over and took his penis in hand again, leading him toward the bath. "I think I should help you with that, just to be sure you get it right."

Somehow, a girl holding his cock for him while his urine splashed in the bowl was far stranger than the girl merely being naked. Would she want to wipe his ass if he had to take a dump? At least, Liz seemed to know about the necessary little shake that completed the exercise. Then she lowered the seat and sat down, legs spread far apart so he could see as she also emptied her bladder.

She tore off a pad of tissue and held it out to him. "Wanna wipe me?"

Jason hesitated, then shrugged. "Sure." He reached between her legs, carefully wiped the warm drops from her pussy, and dropped the tissue in the bowl.

"Thank you, baby." She stood up and kissed him on the forehead as her nipples nudged his collarbone. "I�ll bet not many of your friends have done that."

Back in the bedroom, Liz turned off the lights. Then she slipped under the covers, slid over, and patted the pillow. "C�mon, sweetheart. Come to bed with Liz." Jason joined her and was again afflicted with ignorance. Did she want him to make love to her? But she�d said--- Or was he supposed to just close his eyes and go to sleep? It was frustrating, not knowing all the rules.

But Liz took over again, pulling him onto his side and into her arms. Jason found himself being slowly, thoroughly kissed, which wasn�t quite what he had been expecting. Liz stroked his hair, then let her hand drift lightly up and down his back as she nibbled his ear. She shifted position, pressing his body against her own from chest to knees. His cock began to stiffen again against the warmth of her belly and he slipped his arm around her waist and hugged her. She stroked his calf with the sole of her foot, a delightful sensation.

"Jason," she murmured in his ear, "you�re such a nice boy, and the longer we do this, the more I would really, really like to fuck you." She slipped her hand down between their bodies and grasped his quickly growing erection. "Dangerous idea, though, like I said before. Damn."

"Do you want to suck me off, again?" He was trying hard to sound casual and matter-of-fact.

She cocked her head and considered. "Mmmmmmm, . . . maybe later." She gave him a little squeeze. "To be honest, I�m trying to think of a way to get around the no-condom problem." She studied him quietly and a slow smile spread across her face. Jason had a feeling she had thought of an alternative.

"You know, . . . there is one way, actually, . . . if you think. . . ." He wondered why she was hesitating.

And then he jerked just a little as her thumb stroked across the tip of his erection, causing more of those little sparks to flash behind his eyelids.

"Jason, you know how fucking works, right?" He just looked at her a moment. "I mean, of course you do, I know that." She grinned. "But indulge me here: What�s the basic connection?"

"Connection? You mean, um, my cock goes in your, uh, pussy?"

"That�s the classic version, yes — the old tried and true. But there is, in fact, another way to fuck." She paused again but he said nothing, not being entirely sure what she was leading up to. He was beginning to have a suspicion, though.

"A lot of girls don�t like the other way, they think it�s dirty — but I kind of do like it. So. Jason. How would you like to fuck me in the ass?"

Jason had thought some about fucking a girl, of course, but he had imagined what Liz called the "classic version" — spreading a girl�s legs and putting his cock up into her pussy — or her cunt, or whatever. And it was usually a girl from school he had the hots for — or else maybe Scarlett Johansson. He�d jerked off a few times thinking about those puffy lips.

But putting it up Liz�s ass? Well, he�d certainly heard his friends talking about ass-fucking, throwing that possibility around, but he had never quite been able to imagine it. Doing it wouldn�t make her start to shit, would it? No, probably not, or he would have heard about it before now. Well, what the hell.

"Liz, if you want me to do it in your ass, I will. Are you sure?"

She considered another long moment, then nodded. "Yes. I�m sure. For one thing, Jason, I�m absolutely sure I couldn�t catch anything from you, even if we don�t use a condom. For another thing, it�s so perverted, the idea is making me excited." She grinned again. "It�d be a hell of a way to lose your virginity, right?" Then she became a bit more serious. "Finally, we both know I�m in charge here, right? I mean, I�ll tell you what to do, and that�s how you�ll do it. Okay? Do we have an understanding about that?"

"Yeah, I understand. So what, um, . . . okay, tell me what to do, Liz."

"First all, you may be young, but your dick is getting ahead of your experience." She stroked up and down slowly a few times and he could feel it getting even stiffer, especially now that he knew what was about to happen.

"I think a little lubrication is in order." She glanced around the bedroom. "Do you know if your mother has some lotion or something?"

"Well, I think she has some stuff in the bottom drawer over there," he said, motioning toward the low dresser with the mirror where his mother put on her lipstick and eye-liner. Liz hopped out of bed and Jason watched her tits bounce as she bent over the drawer and poked through the contents.

"Bingo! Better than lotion any day!" She returned and climbed into bed displaying a tube that said "K-Y" on the side. Jason had no idea what it was.

"Your mother must have a sex life of some kind, Jason. This is the best lubrication money can buy, practically." She handed him the tube and took a position on her hands and knees. Her breasts swayed beneath her. "Now, squeeze out a little of that stuff on your cock."

He watched it ooze out along the length of his erection like translucent toothpaste.

"That�s it. Now, spread it up and down with your hand."

He masturbated himself slowly, being careful not to push himself too far. He would totally die of embarrassment if he came before he even got inside her.

She lowered herself onto her elbows and spread her knees apart. "Now, I want you to squeeze a little more of it right onto my asshole."

He made a puddle about an inch across, centered on her sphincter.

"Now, push it inside my ass with your finger an inch or so. Spread it around in there."

He carefully inserted his middle finger into her rectum up to the second joint and rotated it. It was much easier than he had expected. Liz made a little sound in her throat.

"God, Jason, this is going to be so good. . . ." She arched her back downward. Jason, staring at her asshole winking at him, suddenly wanted very much to shove his dick in there. He set one hand on her hip and pressed his quivering organ against her opening with the other.

"Take it slow, Jason! Slow, understand?" She took a deep breath. "Now — push it inside me."

He leaned forward and watched as the helmet-head of his rigid cock gradually stretched Liz open and then slipped suddenly inside. She gasped and then let out a long, low moan. Had he done it wrong? He stopped moving.

"No, no, keeping going, baby. You�re doing it exactly right. It just feels so goddamn good, I almost can�t stand it! Oh, God, . . . ."

Reassured, Jason resumed his forward pressure. The feeling of her rear passage squeezing him was indescribable. He didn�t dare move too quickly yet or he�d lose control for sure. After a minute or two, his cock was completely buried in Liz�s ass.

"Move, Jason. In and out, you know how to do it. Just start slow and gradually speed up when you�re ready to, okay?" She was twisting the sheet in her hands and her eyes were tightly shut. He followed instructions and was rewarded with what felt like neon banners flying up and down his cock. He let his hands glide up over Liz�s buttocks and over the small of her back. She made whimpering sounds and pressed back against him. He decided it was time to do it all.

Taking a deep breath, he sort of shifted gears and began moving faster. The K-Y stuff seemed to be doing its job, and the smooth friction of his fucking was creating a whirling cortex behind his belly somewhere. He could feel the explosion gathering itself, far greater than when he jerked off in bed or in the shower.

Two minutes later, he was rushing up to the brink and he squeezed Liz�s hips.

Her response was to ram herself back against him even harder. "Come in me, Jason! Shoot your cum up my ass, baby! Oh, God, I�m coming, too!"

And as he jerked and spasmed and felt himself shooting his load far up inside her, he could also feel Liz trembling and jerking under his hands and he could hear her gasping and squeaking as her orgasm joined his.

Just as he was sure he was empty, Liz let her knees slide out from under her. Jason immediately put his own knees outside of her thighs and followed her down flat on the bed. He didn�t want to pull out of her yet.

They lay there for a little while, catching their breaths and letting the sweat dry on their trembling bodies. Liz reached back and stroked his thigh and he inhaled the aroma of her citrus shampoo.

"Baby, . . . that was absolutely and completely incredible. I mean it, that was one of the very best fuckings I have ever had, from anyone, of any age. Really, it was."

He was pleased to hear such a compliment, pleased even more that he had made her come. His cock had shrunk to the point now that it was about to abandon its target whether he wanted it to or not. Being careful not to poke his knee in the middle of her back or anything, Jason rolled off her and tucked his hand under the pillow.

Liz turned on her side, reached out, and cupped his head with her hand. "Jason, I�m so glad I was your first one. It�s usually the other way around, you know, the girl is usually still a virgin and the boy has been around. But I�m your first lover and it�s a nice feeling."

Jason smiled. He was having very tender feelings toward Liz just now — which was kind of silly, all things considered — but he knew what she meant. It was nice that his first time was with a girl he knew and liked, but also with someone older who knew what she was doing. What�s more, it was his secret. Liz hadn�t said anything (yet) about keeping his mouth shut, but he wasn�t going to even hint about what had happened, not to anyone. It wasn�t about staying out of trouble — well, okay, maybe there was a little of that — but this whole episode was all his and he was going to be reliving it for a long time to come. And when the guys were bragging and lying about their mastery over girls, he would just listen and smile and not say anything. But he would know.

--- END ---

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Copyright 2012 by Michael K. Smith. Copies may be made and posted elsewhere for personal enjoyment, but all commercial rights are reserved.