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The Babysitter's Prize

Being a bartender usually means I get to have some fun, flirt with the hot, barely-dressed girls and once in a while, get one of the cocktail waitresses to crawl under the bar and suck me off while I'm mixing drinks. I like my job even though I have to put up with the bullshit once in a while from drunk guys who resent it when I hit on their dates, or from the dumbass boyfriends of the cocktail girls who found out their slut girlfriends polished my rod while a few hundred people watched.

I'm not the most attractive guy in the world, I know. I stand about six feet or a little over and I'm well built at a hundred and seventy pounds plus. I have short hair, and tanned skin where it isn't covered by tattoos. My tats sometimes intimidate other people because they're so prominent.

So why is that I get so much pussy? I'm a freakin' tripod, that's why, and I've got the confidence to match. My dick measures eleven inches long when hard and nearly half as long soft. It's not all that thick, which the girls appreciate since it doesn't make their mouths stretch. All the cocktail waitresses know of my python either through personal experience or rumor, and so do many of the hotties who come to the bar. Plus, I wear tight jeans so that my bulge is pretty obvious. Girls stare at my schlong all the time, and I sure as hell don't mind the attention.

I always keep my relationships casual. It's all about the sex, and most of the time, the girls have no problem with that. Still, once in a while, I get some girl – especially the teenagers who come in with their fake IDs – thinking they're in love with me because I gave them the best fuck of their lives. I've popped a few such girls, which is always fun, but they invariably get starry-eyed and hang around, waiting for me after work. It's always a scene when I turn them down.

Hell, one girl even brought her mother to the bar the night after I popped the little slut's cherry, telling Mom that I was the guy she was gonna spend her life with. I just gave the stupid bitch a look and flashed my wedding band. She cried right there in the club and her mother told me I was a bastard who was going to rot in hell. Like I haven't heard that before.

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Yeah, I'm married but I figured, eventually, I'll divorce Mandy, sell the house and give her half the equity, let her keep the kids, Nathan and Donna. At the time, they were sixteen and three months old, respectively. I gotta admit that the little tykes were pretty cute, even if they sometimes made too much noise and bothered me when I came home from work. They were primarily Mandy's responsibility; she was the wife and mother, so it was her duty to change them and bathe them and all that crap.

Still, since my ex wife worked four nights a week, that meant we had to hire a babysitter now and then. Mom came over a couple nights to watch her grandchildren, usually on Fridays and Saturdays, but on Wednesdays and Thursdays, I shelled out thirty bucks for our babysitter, Jessica.
I'll eventually have enough to take off for Amsterdam. I'll spend the rest of my days living off the dividends of my investments, smoking out, and banging the hell out of hot young European sluts.

But it happened sooner than I thought. We got divorced after she found out I had fucked so many girls before I would come home to fuck her, we still lived together for the kids' sake. What did I care I just love pussy.
Anyway . . . oh, right, the babysitter.
Now, Jessica was a nice little piece of ass. Voluptuous and sexily compact, with curly, long strawberry blonde hair, a cute little dimpled face, hefty 44Ds and matching hips, she was a serious wet dream. She had the kind of full, soft lips that were obviously intended for sucking dick. She stood all of five feet seven and weighed about one-thirty.

Jessica was seventeen when she first started babysitting for us, and that fact was the only thing that kept me from introducing her to Mr. Longandhard. Hey, I'll poke any chick that gets close enough, but I do have my scruples.

Our babysitter was pretty quiet and very demure, which posed another barrier to getting in her pants. Plus, she came from a conservative Christian family and always seemed intimidated around me because of my tats. Or maybe it was because she could somehow tell I wanted to bone her ten ways 'till Tuesday.

Anyway, she always made sure that she was never alone with me. Maybe she was afraid I'd rape her; I don't know. I'm not above forcing a girl now and then to give it up, but only if they're cockteasers. But cute little Jessica wasn't a tease. Hell, I was pretty sure, despite how hot she was, that she was a virgin.

That just made me want to fuck her even more.

Jessica turned eighteen about seven months after she started watching the kids, and being my confident, lecherous self, I figured that it was only a matter of time before I got to find out if she was a true blonde like I suspected. I just had to find a way to get her alone for a couple of hours.

On this particular Wednesday night, I'd gotten into it with a guy named Derek, who came into the bar with the intention of kicking my ass. He had heard that his girlfriend Letty (a hot little Hispanic beauty who cocktailed on the weekends) had showed off her talent for deep throat by taking my snake all the way down, right there in the bar as our patrons cheered, and proved that she was a swallower. Stupid asshole. Does he get mad at his girlfriend for being a cocksucking slut? No, he comes after the guy she blew.

Well, I beat the fuck out of the little shit right there in the bar, and my manager Ross decided to send me home to avoid further trouble. Fine with me. Letty's little punk boyfriend had pissed me off to the point where I didn't feel like being around people. I figured I'd head home, take a shower, change my clothes, and call up one of my girls. I needed to vent my frustrations, and while turning Derek's nose to hamburger had been satisfying, what I really needed was pussy.

And then I pulled up before the house and saw Jessica's car in the driveway. I had been so melancholy that I had forgotten it was Wednesday. I suddenly grinned. It was a little after eight o'clock; Mandy wouldn't be home for another two hours at the least, and the kids would be in bed . . . hmm . . . oh, yeah.

I switched off the lights, turned the car into the driveway beside Jessica's and parked quietly. I noticed a crappy little sports car parked along the curb, and music coming from the house. Not real loud, but loud enough that it masked the sound of my car's engine. I narrowed my eyes. I had told Jessica that she was not to have friends over while she was babysitting.

But I wasn't mad. In fact, I realized that here was an opportunity to coerce Jessica into doing what I wanted.

I headed around to the side door beside the garage, instead of going through the front. Carefully, quietly, I unlocked the door, stepped in, closed it behind me. I padded to the door from the garage that opened into the kitchen, and opened it just a crack. The music became a little louder. There was no one in the kitchen.

I paused, listening. I heard some faint kissing sounds coming from the direction of the living room, around the corner from the kitchen doorway some fifteen feet ahead of me. I chuckled softly. Jessica's got a guy over. Now I really had some leverage. I knew from conversations with Mandy (Jessica and my ex wife talked a lot since they were only about five years apart in age) that Jessica's parents were serious Bible-thumpers who expected their little girl to stay chaste and pure until her wedding night.

Well, little Jessica sure as hell won't be pure by the time I'm done with her.

"Wait . . . wait, Remy," I heard Jessica's pleading voice. "Don't go so fast."

I inched to the doorway and slowly peered around. What I saw made me catch my breath. Jessica lay back upon the big couch in the living room, in profile to me. Her little yellow top was off, laying on the couch, her firm, round, braless tits completely exposed. She had soft, lightly-tanned skin, and her tits literally floated on her chest. Her nipples were bright pink and stiff, sticking up toward the ceiling. She had a soft belly, with just a little rise to it.

Between her legs, working her panties down her voluptuous, somewhat muscular thighs, was a boy about her age, shirt off, clad in jeans. He gave her an excited smile as the thick bush of wheat-colored pubes was revealed between her legs.

"Oh, baby," he said in awe, staring at her revealed cunt. I had to envy his view. He tugged her panties all the way off, touched her well-toned thighs. He pushed her legs apart.

"Remy, wait," Jessica said again, sitting up and grabbing his hands. I loved the way her firm C-cups swayed. She gave her boyfriend a pleading look.

Remy tore his eyes from Jessica's pubic thatch and gave her a confused look. "What? What am I doing wrong? I thought you wanted this, babe."

Jessica looked apologetic and confused. "I-I'm just not comfortable," she said. "I mean, th-this is Mr. Orton's house."

Remy frowned. "Well, you said you didn't wanna do it in the car, and we sure can't do it at your folks' house—"

"I know, I know," she said, then huffed. "I-I just . . . ." she suddenly covered herself up self-consciously, wrapping her arms around her generous tits and crossing her legs. She stared at the floor.

Her boyfriend sighed in frustration and lurched to his feet. I almost laughed when I saw the tent in his jeans. Poor Remy. All worked up and no place to cum.

"Why are you teasing me lie this?" he asked in exasperation. "I mean, we've been dating for, like, two months! And you keep telling me you think you're ready, then you back off, then you think you're ready again, and . . . it's driving me crazy, babe!"

Jessica looked pained. Fuck, was she hot, just sitting there naked with her jeans and panties laying on the floor, wearing nothing but little white ankle socks. My dick was getting hard, snaking down my left pant leg.

"Look, it's not easy for me," she said in a little voice.

"And it's easy for me?" cried Remy.

She snapped her head up. "Shh, Remy! Don't wake the babies up!"

Remy groaned, staring at the ceiling as he tried to control himself. He finally looked back down at her, admiring her body. He forced a smile.

"Okay," he said, trying to sound endearing. "If you don't wanna go all the way, then . . . maybe you could try sucking it again."

Jessica looked pained. She grimaced. "Remy, you know I'm not comfortable doing that," she said.

Remy held back a frustrated sigh. "Why not? I mean, you always lick it a little when you jack me off."

Her shoulders sagged. "Do you have to say it like that?"

He rolled his eyes. He was getting close to wits' end. "Say it like what? Isn't that what you do? Jack me off?" he breathed out, shaking his head, then spoke in a sarcastic tone. "Oh, I'm sorry. You masturbate me. You tenderly stroke my penis. Jesus, Jessica—"

She suddenly glared at him. "Don't take the Lord's name in vain," she said forcefully.

I sneered. Bad move, kid. You're definitely not getting any action tonight.

Remy stared a moment, then forced himself to give a soft, apologetic look. He got down on his knees, touched her bare legs. "Baby, look, I'm sorry," he said. "It's just that you're so beautiful, and so sexy, and . . . and I really love you. I just wanna prove it."

Jessica seemed to melt a little, and she parted her lips, lowered her arms a little. Her pink nipples poked out. "Oh, Remy," she said emotionally. "Do you really?"

Uh-oh, I thought. I shook my head. I can't believe she fell for that. If I don't make a move now, Remy's gonna get my prize. Might not be a bad thing to watch, but I'm not gonna lose my chance to savor this virgin beauty before he does.

He smiled up at her face, reached for her hands. "Baby, I can only tell the truth," he said.

Now I rolled my eyes. Okay, enough's enough.

"Tell me again," I heard her say as I straightened up in the doorway. I took a deep breath, then headed around the corner just as Remy began to respond.

"Jessica, baby, I – holy shit!"

It was actually pretty comical. Remy jumped up, staring at me in sudden fear, stumbling back and falling over the coffee table, He cried out as he fell to the floor. Jessica snapped her head around, seeing me and covering up again, shaking as she reached for her clothes.

"Don't! Move!" I said in a deep, commanding voice, jabbing a finger at her. Jessica froze, her right arm across her breasts, hand cupping her left tit. Her eyes and lips trembled as she stared at me, absolutely mortified at being caught naked in my living room, and with a boy.

"You!" I snapped at Remy as the kid scrambled to his feet. The boy paled, looking like he was terrified for his life. His eyes darted over my tattooed arms. He was clearly intimidated.

"Get your fucking clothes and get out!"

Remy obeyed quickly, and snatched up his shirt and leather jacket from the floor. He gave Jessica a furtive look, then darted for the door. Without a word, he jerked it open and ran out. I caught the door before it could slam shut, and closed it gently. Didn't want to wake the kids, you know.

I turned back to Jessica, saw her beginning to thread her arms through her little tank-top. I frowned. "I didn't say you could move," I said in a threatening tone. "Put that down."

She looked at me, surprised, fearful, intimidated. "M-Mr. Orton?" she queried.

"Drop it," I said.

Jessica shuddered, let the garment fall to the ground at her feet. She covered her incredible tits, crossing her wrists beneath her chin. Faintly, outside, I heard the sound of a rattling car engine, then the squeal of tires. Remy was gone.

Damn, she is a beauty, I thought, ogling Jessica's beautiful body. So young, so fucking ripe! And apparently, a virgin in every way. My dick pulsed in my tight black jeans. I wondered if buxom little Jessica noticed. But probably not; her eyes were on the floor.

"You know, I trusted you," I said, pacing back and forth. "At first, I wasn't too crazy about the idea of letting a teenager take care of my children. But my ex wife convinced me. She said you were responsible, and reliable, and I believed her."

I faced her, drinking in Jessica's lovely, voluptuous, golden-toned young body. Even though her legs were crossed, her thick blonde bush could not be obscured. Jessica shuddered silently and she cried softly, tears slowly dripping down her innocent, little-girl face. My cock throbbed. I could have taken her, I could have grabbed her and thrown her legs open and shoved my cock up inside her. But I wanted her to feel desperate and frightened enough give herself willingly to me. Besides, I was enjoying the torture I was putting her through.

"And now I find out that you've been having sex in my house," I said. "My house!"

Jessica snapped her head up. "N-no!" she protested, her eyes wide and full lips trembling. "I swear! W-we didn't! I-I promise!"

"You 'promise?'" I asked, laying it on thick. "Then why the fuck are you naked in my living room?"

Jessica shuddered as she cried, squeezing her eyes shut. I watched her tits bounce as she wept. Damn, but for some reason, she looked even hotter with tears flowing down her soft, full cheeks, dripping off her chin. It reminded me of cum.

Hmm, wonder how she'd react to getting a facial, I thought. I took out my cell-phone, moving slowly and deliberately so Jessica would notice. I calmly began pushing buttons at random.

"Wh-who are you calling?" she asked fearfully.

"Your parents," I said simply. "It's not my place to discipline you. I'm sorry, Jessica. I wanted to trust you."

Jessica's face contorted. "Oh, God, please!" she cried, and jumped up, apparently forgetting her nudity. Her firm, round tits shook as she grabbed my arm. She gave me the most pathetic, pleading expression I had ever witnessed. "Mr. Orton, please! I-If they find out, th-th-they'll take my car away, a-and my computer, a-a-and they'll never trust me again! . . . oh God, please, Mr. Orton! Please!"

I gave her a look, even as admired her curvy young body. Damn, but I hadn't seen perfect, natural tits like hers in years, and that soft, thick blonde bush . . . .

"And I'm supposed to trust you now?" I asked. "I'm supposed to believe that you'll never bring your boyfriend over and fuck him on my couch? I hold my children on this couch, Jessica! I sit with my ex wife and tell her I love her on this couch!" Heh, heh . . . yeah, right . . . .

Jessica blubbered, squeezing my arm. "I promise, Mr. Orton, I've never had sex on your couch, or anywhere else! I promise!"

I narrowed my eyes. "And how am I supposed to believe you?" I asked, and quickly slipped my hand between her muscular thighs, cupping her dewy little blonde cunt. I forced down a shudder of arousal as I felt her sweet lips and the little button of her clitoris. "Next thing you're gonna tell me is that you're still a virgin."

Jessica's eyes flew open wide as I groped her young snatch. Damn, but she was so hot, her pussy so soft and furry. Her pubes felt more like goose-down then hair. I lightly stroked her fleshy little labia with the tips of my fingers.

Surprisingly, Jessica did not pull back from my hand. Indeed, she seemed to grip my arm more tightly and even pushed her hips against my hand. Or maybe it was just my imagination. Maybe.

She didn't look to my face. "I-I am," she whispered. Her lips swelled and nostrils flared slightly. Her cheeks glowed with rouge.

"Oh, come off it," I said, and jerked my hand away. I casually sucked my finger. Mmm, oh, fuck, she tastes good! So rich and sweet and pure! But I said, "You don't taste like a virgin."

Jessica shuddered. "P-Please, Mr. Orton," she said, her voice barely a whisper. She looked up to me desperately. "I don't wanna get in trouble with my parents. My Dad . . . He'll beat me, Mr. Orton. He'll take off his belt, and . . . I won't be able to sit down for a week. Please. Please."

I stared at her. "So am I to believe that you really are a virgin, that you've never had sex in my house?"

She nodded slowly, wiped her eyes. "I promise," she said in a little girl voice.

I kept her gaze. "Prove it," I said.

Jessica stared, her soft blue eyes wide. Her mouth fell open. Damn, I could just imagine that mouth wrapped around my dick, sucking and pulling eagerly . . . .

"P-prove it?" she asked, shocked. "H-how?"
4 comments

anonymous readerReport

2013-08-12 22:55:38
to the person that is saying this is crap well this isnt a true story its more enticing it doesnt need to be true this is asex stories site they can have exadurations and fun i know im rambling but i dont care

anonymous readerReport

2012-06-15 03:41:10
what a load of crap, 11 and a half inches

anonymous readerReport

2012-06-14 23:27:50
Jessica harter i could use a woman like you to txt and sext;) do you want my number? Im Alot of fun to talk to;;)

anonymous readerReport

2012-06-14 23:26:53
Jessica harter i could use a woman like you to txt and sext;) do you want my number?

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