Adventures in Sitting

Marcy Jones had to be the most gullible woman in the United States, Heady thought to herself. Where to begin though? Marcy was flying to Chicago to visit her sister. Mistake number one; never leave a lying husband to his own devices. But then again Marcy didn't know Scott was a liar, mistake number two. It was funny that Marcy was more fearful of her teenage son engaging in underage drinking than she was of Scott's faithfulness. She trusted Scott more than her son, mistake number three. So much so that she believed her husband when he suggested they have Heady spend the week at their house to keep an eye on Leon. Why hire a sitter when dad would be in town, well, because Dad would be working late. Heady supposed Scott would be working late, working late on bringing her to orgasm. Stupid, trusting, Marcy. Heady smiled to herself, a weeks stay in the big Jones house, under the pretense of sitting, when her evenings would be spent sitting on Scott Jones' face.

The boys were in the backyard playing basketball, and Heady could afford a moments peace. Besides, she could keep an eye on them from the hot tub. Scott wouldn't be home until 8 or 9 PM and that gave her some time to work on her tan. She took one of the single serve piña colada packs out of the freezer and added a generous helping of rum. Now that was the way to start off the afternoon! She'd worn her swimsuit underneath her clothes as she often did when babysitting for the Jones - you never knew what was going to happen. The hot tub was nestled in a secluded area of the backyard. Ivy crept up the white latticework Marcy had installed for privacy. Heady laughed to herself, good thing, who wanted to see Marcy's wrinkled ass anyhow? At least she'd have her privacy, and a moment away from those sugar-hyped teenagers.

She removed her tank top and shorts, revealing a chocolate bikini. It brought out the deep brown in her eyes and hair. The triangle top did little to cover her swollen breasts, with her period on the way she'd have to have her fun while she was able. Her nipples were sore too - it hurt to even pull the tank top off. The hot water would help. So would the alcohol. She'd waxed her bikini line a few days ago; Scott liked it smooth and so did she. She traced her fingers along her inner thigh up to the quarter inch strip that covered her slit. It felt so good. Even better when Scott licked her there, working two thick fingers in and out of her as he suckled. She thought it was ironic that he used his index and ring fingers, symbolic really. She slipped a toe in the water. Nice and hot, just how she liked it. She eased herself in and reclined; her breasts bobbed on the surface of the water, full and voluptuous. She could hear the boys playing one-on-one in the distance. Leon, Scott's son, had had a crush on her for years. She'd been babysitting for him for just as long, and now that he was in his teens he was starting to get the same handsome, distinguishing features as Scott: a strong chin, a more defined upper body, and-although she had no way of knowing-probably some endowment below the belt. Heady liked her men big, and older, typically, although if Leon continued on the right path, maybe she'd be open to a little father-son bonding. She took a sip of her drink and closed her eyes.

Matt dribbled the ball away from Leon, and did a dramatic lay-up, hanging from the rim of the basketball hoop. Sweat dripped from his shaggy brown hair. "Whose house is this? Hahaha fucker, your ass was spanked!"

"Whatever man, I'm beat." Leon bent over to catch his breath. His dark skin only defined his growing muscles.

"Yeah, I know you're beat, cause I just whipped your ass." Matt dropped from the hoop and tossed the ball into the grass. "What now?"

"Let's get something to drink, it's air conditioned inside."

"What happened to that sitter of yours?"

"Beats me." They left the court, and walked up the back steps of the deck towards the house.

"Aren't you too old to have a sitter...that is, unless she's sitting on your face." Matt cackled.

Leon spun around and faced his best friend, "It's your damn fault Matt, and you know it. The party last summer was your idea, and now I have a fucking sitter for the week because my mom doesn't think she can trust me."

"Hey man, I did you a favor, you know you want Heady, maybe you can get closer with her under the same roof." Matt grinned, "That or I could work my charm."

"Shut up, man. It's never going to happen. My mom's blind anyway; I can't be trusted? Dad's been cheating on her for years-late night work, more like late night fucking."

"Shh-shiiiiit." Matt exhaled, and pulled Leon back behind the white latticework.

"Shut up Matt, she'll hear you," Leon whispered.

"Damn, looks like your sitters got some titters on her. She's making me hard."

"Her tits aren't that big. I could fit one of those in my mouth."

"Fool, I don't know what kinda mouth you have, but you ain't seen shit."

"Oh, I wonder if she's shaved."

Matt looked at Leon like he was crazy, "A chick like that? Totally." He paused darkly, "Wanna find out?"

"What? How? Wait, no!"

"Some of your moms goodnight pills? She's already drinking, a few of those in her drink, and that's the end - goodnight for her and goodnight for us."

"I don't know."

"Come on Leon, I know you've had a hard-on for her since you could get hard. Now's your chance. It's the perfect plan."

They found the pills in the nightstand of the master bedroom. Apparently the drawer was a drugstore because along with pills it also housed condoms, lube, birth control pills, and what turned out to be a tiny box containing anal beads. In the kitchen, Matt ground five pills into a fine powder. They added the mixture to the half empty piña colada and stirred. They returned it to the deck. She was still half awake.

Leon spoke up, "Heady, Heady?"

She moaned a little and then opened her eyes, remembering where she was. She pulled at her top, trying futilely to hide some of the exposed skin. "What?"

"Heady, my mom's on her way home, and I know she'd flip if she found out that you've been drinking, if I were you, I'd drink that down fast. She should be here any minute, she just called."

Panic flashed in her face, "Thanks Leon." She downed the rest of the drink quickly, and started to get out of the hot tub.

Matt chimed in, "You don't have to get out, we were going to play another game of ball anyway. Won't Mrs. Jones want to make sure you're "watching" us?"

"Ha, you're right. Since you guys need so much supervision." Heady eased back into the water and closed her eyes. "Wake me up when she gets here."

"Sure thing."

It was the longest wait of their lives, but after calling her name, screaming her name, and gently slapping her face, they were sure she was out. She was breathing softly, and her body was soft and limp.

Matt took off his shoes, socks, and shorts. His cock was rock-hard and bigger than Leon had thought. He stepped into the water. "Dude, I've never fucked in water before."

"You've never fucked. And who said we were fucking anyway."

"Are you kidding me? How can you stop here, with this?" Matt gestured at Heady. He reached into the water and parted her thighs. Then his hand groped at her pussy. "Oh man." The side ties on her bottom were easy to undo. The chocolate suit fell away. His palm cupped her pussy and he rubbed her pussy lips with his thumb. "Well, she's got a landing strip - so I guess I was wrong." He inserted his middle finger into her, "but I'm not complain'."

She moaned.

Leon jumped back, "See! She'll wake up."

Matt was calm, "No man, she's out. And she's liking it." He ran his fingers up and down her slit. Her hairs were soft and neatly trimmed.

Leon looked intrigued. "What about her tits?"

Matt nodded towards Heady's breasts. "What about them?"

Leon pulled off his shoes, socks, and shorts and stepped into the tub. He'd wanted Heady for so long, used lame excuses to get close to her - starting tickle fights when they were younger, touching her pussy "on accident" or straddling her. She'd never seemed interested in him though, always in other men, older men. He settled in next to Matt and pulled the string on her top between her breasts. The top fell away, revealing her large, soft breasts. The nipples were caramel colored marbles. He opened his mouth onto her left breast, "I take it back, these are more than mouth sized." He salivated over her breasts suckling them, kneading the right one, rolling her nipple between his fingers. He was unconsciously humping her side as he did, unable to control himself. He was so hard. "Ah, Matt, ah!" He shot up in the tub, and jizzed on her breasts, rubbing the cum over her chest, teasing the nipples again. He sucked them more, his cum smearing his own face, before he kissed her - violently forcing his tongue into her mouth. It was warm and moist like he imagined her to be.

Matt was reclining at the other side of the tub, watching Leon with a smirk on his face. "And you didn't want to fuck."

"Shut up man."

With Matt out of his way, Leon straddled Heady's hips. He moved his hand between her legs and felt her smooth pussy. He fingered her, enjoying every feel of her wet inner. He inserted one finger, two, three. She felt so good. He couldn't control himself. He spread her lips with his fingers and fondled the head of his cock. It would feel so good to be inside her after all these years. He rubbed his dick over her pussy, up and down her slit, teasing himself a little; he had to hold out a little longer. He plunged into her when he couldn't take it anymore. Banging into her deeply on the first thrust. Her back arched at the force, and her breasts jiggled forward. Leon steadied her by placing a hand on her lower back, inserting some fingers into her ass crack. He penetrated her with long deep strokes, pulling out of her almost completely before sliding back in again. Her breasts jiggled and shook, and he craned his neck down to lick off his cum and suckle at her tits.

"Ahh. Ahhhhhhhhh. Ahhhhhhhhh." She felt so good on his dick.

Heady sighed again in her trance-like sleep, murmuring a little in Spanish and English. Her pussy muscles clamped down on Leon's eager dick. He cried out, "Ah! Ah! AH!"

"Is she spasming?"

"Ah! She's fucking - yeeeeahhhh!"

He fucked her faster, poom-poom-poom, and exploded into her womb, filling her with hot cum. He pulled out of her and smeared his wet dick over her lips. Placing the head in her mouth. "Damn, Matt, that was amazing."

Matt pulled Leon away from Heady. "Well, now that you're done, I'll need your assistance." He grabbed Heady's left breast and squeezed before picking her up and laying her boobs-first onto Leon's chest. Her ass was exposed to the air, just above the water.

"What are you doing?"

"What do you think?" Matt reached into her pussy from behind, and scooped out Leon's cum. It slid out of her dripping pussy, and he smeared it over her asshole - sticking two fingers into her tight hole to lubricate properly. "You think you've seen tight?"

Matt fingered her a few more time for good measure, and began a slow push into her asshole. Heady gave a quick, harsh moan in her trance. "Finger her clit, while you're down there will ya?" Leon willingly obliged.

Matt pressed his cock in to the hilt, pulling out slowly, before building his speed. She stretched to meet his movements, and he rhythmically pounded into her, his balls slapping her ass viciously. Matt raised Heady's hips, squeezing into her full thighs with his hands. Her breasts slapped into Leon's face. Spattering his cheeks with the remaining jism.

She moaned, "Ay Papi."

Matt picked up his speed, concentrating on his thrust, "Ah!"

She shot his hot load into her ass, and pulled out, jism dripped out of Heady's ass and into the hot tub.

Leon held Heady's limp body in his arms and kissed her again.

Matt watched the cum ooze out of her asshole and lowered his head to her brown star, licking and sucking his cream out of her ass, and kneading the soft flesh of her buns.

Leon fingered her pussy, working three fingers into his sitter's tight twat.

"Fuck, what time is your dad getting home, Leon?"

"How should I know, you think he tells me anything?" Leon groaned and felt the sticky vaginal juices from Heady's pussy moistening his fingers. "Why are you asking at a time like this?"

"I think I just heard the garage door."

Leon stared at Matt for a moment. "Well help me fucking move her!"

The boys fumbled with the chocolate bikini, hastily dressing the voluptuous sitter and laying her back in roughly the same position they had found her. She was still breathing softly, in a deep sleep.

"How long until the pills wear off?"

"How the hell should I know?" Matt replied, pulling on his pants. Let's just get inside before anyone comes back here. He snatched up the empty piña colada glass and followed Leon inside.

Scott had just walked into the living room when Heady came in from the back patio. Leon had left a note by the hot tub saying he'd gone to the movies. Heady wondered where he'd really gone but realized Scott wouldn't care either way. Her breasts where red and swollen, she guessed from the water, and her body was sorer than usual-her PMS was terrible this month. Scott came near Heady, his facial hair starting to grow in after a long day of work. She liked a little scruff on him, it accentuated his jaw, and he carried the musky scent of cologne that always reminded her of sex.

"You look amazing." He wasted no time and squeezed her breast, pulling her into his broad shoulders, slipping his hand into the cup of her bikini top. His other hand reached around to her ass, which he groped hungrily. He breathed into her damp hair, "I'm so fucking horny, I'm gonna fuck your tight little college pussy all night long."

Heady smiled, "Oh, are you?"

He unbuckled his pants, and she pushed him back onto the leather sofa. The fine tailored fabric dropped to the floor, and she dropped to her knees.

"Where's my favorite dick?"

His hard, brown cock sprung to life and she licked up the shaft, from testicles to tip, teasing the head with her tongue. Scott's was a perfect smooth cock; it even tasted good. She took her time, savoring the pre-juices that seeped down her throat.

Scott dug his hands into Heady's hair, "We've got all night, you don't have to save me-you know I've got endless reserves for your pussy."

Heady picked up speed, applying light pressure to his dick by gently squeezing it between the roof of her mouth and her tongue.

Scott started to moan, but pushed Heady onto her back on the floor. She instinctively straddled her legs and he tore off her bathing suit bottom. He stroked his cock, once, twice before cuming on her pussy. He rubbed the cum into her wet hole, then pushed 3 fingers into her twat and began to finger fuck her rapidly.

Heady cried with pleasure, "Ay, Papi, oh, ohhhhhhhhh."

Just as quickly Scott lowered his face to her pussy and began sucking on her swollen, engorged clit. Heady was crying out loud, "Please, please, Papi, fuck my pussy, fuck my pussy."

He picked her up, and she wrapped her legs around his hips, trying to find his cock with her hands. He held her in one arm, restraining her arms with the other hand.

"Where are they boys, Heady?"

"They're at a movie."

"Good." He carried her into the kitchen and put her naked ass on the crux of the kitchen countertop. Pussy juice ran down her thighs, her legs spread wide, one foot resting on the stovetop. Scott bumped around in the fridge, returning to Heady with a cool, slim, cucumber. He pressed his mouth to her swollen clit.

"Please, Scott," she whined, "now, fuck my fucking pussy!"

He kissed her and pulled back so he could watch her face. He pressed the rounded tip of the cucumber into her pussy, slowly, listening to her moan, watching the muscles in her face twitch with nerve-racking pleasure.

She humped against his hand, arching her back to force the vegetable deeper into her. Scott dropped down, and suckled her clit.

Heady humped his hand, and he began to slowly pull the cucumber out of her before pushing it back in quickly.

"Ahhhhh! Papi, fuck me! I'm-Ahhhhhhhhhhh!"

Scott pulled the cucumber out, Heady's vaginal juices dripping from it. He bit off the wet end of the cucumber, and crunched into the vegetable. "You're worth every penny, sitter. Good thing the boys are at the movies, we'll watch a movie of our own."

He picked her up and carried her upstairs to the master bedroom.