Babysitter Gets Boinked

Dan was thinking about the delectable barely legal babysitter through the entire date with his wife Sonja. Dinner was lagging in conversation, the movie was sold out and he wasn’t looking forward to the obligatory Friday night predictable fuck.

Dan's son Greg was eighteen. A reliable teen but not when it came to taking care of his two much younger siblings. He usually locked himself in his room when the sitter came over. Greg kept fairly to himself, didn't throw tantrums or pull stupid teenage shit. Dan couldn't quite grasp the punk thing his son was into or much 80s music, but he was fine with it.

Sonja wasn’t feeling well, asking him to hurry home because she may throw up. Dan didn’t have the chance to open the garage door, she bolted through the back door and headed for the bedroom. Usually she checked on the kids but tonight she didn’t. He knew if she threw up she'd pass out afterwards, it was a strange coping mechanism.

Dan walked into the living room, thinking about driving the hot little babysitter home. Trying to think of ways he could accidentally touch her.

She wasn’t in the living room. He checked on the little ones, they were deep asleep.

He approached Greg’s door and heard music. It wasn’t his son’s usual gloomy stuff it was R&B, soul. Sensual soul. And there were sensual sounds to go with it. Pressing his ear to the door he distinctly heard his son groan.

No fucking way. Greg’s getting some from Sherry? Carefully, he turned the doorknob, thankful it wasn’t locked. He was home three hours sooner than expected. He opened it a crack and had a view of his son getting head.

Greg was nude, lying on his back, his legs spread wide. Sherry was down to her panties, her ass in the air, her head between Greg's legs. Dan felt his cock grow harder than it had been in years. For the first time he was envious of his son.

“You like this Greg?” she asked as she stroked his dick. He nodded, his eyes barely open, his mouth gritted closed. “Is this really your first time?” He nodded again.

Dan found that surprising. He’s a handsome kid, a little timid but the punker thing probably put girls off. Who knows, who cares? He’s getting a blow job from the babysitter!

“Can I suck your tits more?” She nodded and he sat up. Suckling like a baby while a free hand cupped the other breast, lifting it, squeezing. She moaned with delight and he switched to the other.

Rubbing his head she sighed, “Oh Greg, you’re good at that. Mmmm.”

“ Can I feel  if you’re wet?” She nodded and he slid a hand into her knickers. “Oh. Uh Sherry, I think you’re ready. Can we fuck now?”

“First you need to rub my clit.” She guided his hand. “There. Oh yeah, Greg. Rub it, yesssss.” She was riding his hand, his eyes locked on her rapturous face. “That little spot, yes. Rub it until I come.”

“Okay.” Greg focused on working her clit but the breasts in his face were distracting. His tongue snaked out, flicking a nipple. She gasped, making him smile.

Dan was proud of his son and at the same time he wanted to kick him out of the room and take over. His cock was throbbing, he could feel pre-come sliding down his shaft.

“Greg. I’m coming. Don’t stop rubbing.” Sherry panted as Greg intensified pressure.

Dan watched as Sherry’s hips rocked his son’s hand. Greg was watching her face, trying not to come seeing the ecstasy he gave her. She was moaning, holding his shoulders, riding his fingers. Suddenly she threw her head back, cried out and bucked as she came.

Greg blurted, “You’re super wet.” He pushed her back, she easily fell, weak and loose from her orgasm. “Now we fuck.” As quick as he could he yanked her panties off and threw it to the side. “I’m gonna fuck you Sherry.”

Dan gaped as his son’s cock aimed at her cunt.

Her hands slapped his bare chest. “Be careful..I..I’ve never-“

“I’ll try not to hurt you.” Probing her slit with the head of his cock he asked, “Here?” She nodded and he pressed, “Oh. Oh fuck.” She whimpered as his cock head entered. “You’re all right, you’re all right. Girls do this all the time and don’t die.” Her face was pinched as he shoved in but he was blinded by the grip on his dick. “Oh fuck. It’s so warm. Oh fuck Sherry, I-“

Dan saw his son’s white ass suddenly pumping for all it was worth. Greg was groaning loud. Sherry was working on being brave, pain outshining pleasure.

“You feel so fucking good. It’s so hot. Oh fuck Sherry, I’m coming. I’m coming!” His back arched as shot after shot sprayed into the girl who never gave him a second thought.

But tonight, Greg thought to himself, Tonight I fucked her. I can see her at school and think about her hot pussy. How I tore her open her first time. How she sucked my cock. What her tits look and feel like.

Greg felt like a god. Sherry felt like a slut. Dan felt like taking over.

He opened the door, “Sherry what the hell are you doing to my son?” It took effort to keep a serious face.

“Oh! Mr. Wells, I’m so sorry. I- uh, Greg here was-“ Greg was still smiling over the fact that he filled the sitter. “He and I-“

“You were fucking. I saw. I saw you suck his cock too.” Her eyes were wide, she was spooked and Dan liked it. Greg pulled out and sat beside her, lost in his own little world of afterglow. Dan said, “I’ll make you a deal Sherry. You let me tap your sweet hole and I’ll call us even.”

“What?” she asked and then looked at Greg for help. Greg shrugged.

“Come on Sherry,” Dan said as he undid his trousers. “What’s another cock now that you’ve been broken in?” She eyed his hard on which sprang proudly upwards.

She was still on the bed, sitting up, her long legs straight before her. Dan came over and motioned for her to lie back, she moved slowly.

“Greg, you did all right your first time son. Getting a girl to come first is smart, getting her to come again when fucking is even better.” Dan pried her legs apart and bent over her. “Don’t move,” Dan said to Sherry. “Greg, you want to hit the gspot.” Greg watched his Dad slip a finger into her. “It’s toward the belly about a finger’s length in. It’s easiest to find it after she comes.” Dan smiled at his son. “Here, right now it’s swollen to about the size of a grape. It’s a little bumpy. Slide your finger in son, I’ll show you.”

“Hey, uh-“ Sherry tried to squeeze her legs closed, “-this is-“

“You’re fine Sherry,” Dan said. “You decided to fuck my son so at least let him learn the right way.” She relaxed her legs a little. “Go ahead, slide a finger in.” Greg did, following his Dad’s finger he found it and smiled. Two men in her twat, Sherry was embarrassed. “Now, some like it rubbed like this.” Sherry gasped.  “Some like it poked.” She whimpered. “She’s new, sometimes girls don’t like it at all. They may even feel like they have to piss, nerves are too close to the bladder or something. Hell, if they do piss who cares. Fucking is messy.” Greg chuckled as he watched Sherry’s face while he rubbed her gspot.

“Did I make it bigger?” Greg asked his Dad. He nodded. “Cool.”

“Best to mix it up. But if you get a girl to come that way she’s yours. She’ll never forget it. Watch.” Dan picked up Sherry’s legs and set her feet on his shoulders. “Hold them there girl. Don’t move.” He turned to Greg. “This is a good angle. I’ll show you others. But first I gotta get in. Was she tight?” Greg nodded. “If a girl takes care of herself, exercises her pussy she’ll stay pretty tight.”

 “Mr. Wells?” she asked timidly.

“Yeah?” He glanced at her face, although he’d rather be looking at her fresh looking tits.

“You really going to..”

“Sherry, you’re going to get fucked well. My son did an excellent job for his first time but I want to make sure you get fucked properly.” Unable to resist, he pinched her nipple making her gasp. “Nice tits.” He began to suck it, shocked he was milking the eighteen year old girl he was hoping to steal a grope from. Now he was lying on top of her, her nipple in his mouth and hand, his throbbing cock at the entrance of her fresh young pussy.

Greg said, “It’s okay Sherry. We won’t tell anyone.” That seemed to reassure her some. “Go on Dad.”

Dan pressed his cock against her hole, his son’s leftovers and her wetness made it easy. Her tight little opening did not. Sherry whimpered as her sore pussy was being stretched yet again.

Greg stroked her forehead. “It’s okay baby. He’ll make sure you like it.”

Dan would have been moved by his son’s thoughtfulness but all he could think was- I’m fucking the sitter! My cock is in her tight little cunt!

Greg bent over so they were face to face and said quietly, “I haven’t kissed you.” When his mouth met hers he realized that he had wanted to kiss her as much as he wanted to fuck her. Holding her face in his hands he slipped his tongue into her mouth. Sherry quietly groaned, it was a happy one. Sherry, do you like me?”

 “Yeah,” she looked away. “That’s why I babysat. I think you’re cute.”

He grinned ear to ear. “Me?” She nodded. “You’re so pretty.” He kissed her again. Dan cleared his throat. “Oh.  My Dad’s going to show me how to make you come more. Okay?”

Before she could say anything Dan said, “Okay son, now watch how I do it.” She’s so tight. Feels twice as hot as my wife’s cunt. “Put a pillow under her ass. Good. This angle, watch her face.” Sherry watched Dan’s large cock slide in and out of her. Greg touched her face and held her hand. “She’s all right. They just need to warm up.”

Holding her slim, smooth legs, Dan bent over her, folding her in half. His ass pumping just like his son’s had earlier. Sherry made small moans as Dan grunted.

Greg fondled her breast. “You’re so soft Sherry.”

Dan was trying not to come. This young girl, his son watching like it’s an educational video and his dick getting squeezed was too much.

Sherry was getting close. If her little cunt began to dance on him, he was done. Dan changed positions. Back onto his knees he held her legs wide, spread apart as he leaned back. When he thrusted upwards Sherry’s groans changed. She liked this even better.

“I think she’s almost there,” Greg said to himself.

Dan doubled his effort and hoped he could hold off. He really wanted to fuck her on all fours. Slamming into her, the meaty sound of his thirty-eight year old body smacking her young flesh was so erotic he almost blew his load before she did.

“I think-“ Sherry’s voice cracked. Greg moved to get a closer look of his Dad’s cock piercing his new girlfriend. “I’m coming!”

She wasn’t the only one. Dan growled as his balls pulled, shooting his wad so hard he thought it had to sting. Sherry’s legs hooked themselves over Dan’s shoulders as he finished.

 I’m blowing my cream into a girl! A young girl! Dan was screaming in his head. The sitter! I’ve fucked the sitter! Feeling victorious he smiled as he caught his breath.

Sherry was panting, Greg was mesmerized by the amount of fluid that spilled as his Dad withdrew.

 “Get me a towel son.” Greg dashed from the room. His rigid dick comically smacking his stomach as he went.

“Good job Sherry.” Dan smiled at her. She was uncertain how to respond. “I’ve been wanting to fuck you for awhile. Thought of pulling the car over and doing it on the side of the road.” Her eyes were wide. “We’re not done. A couple more tricks before I call it a night.” He bent over her bringing them face to face. “Don’t worry sweetie, you’ll come again. So will I. So will Greg. You’re going to make my boy very happy.” He sat up.

Greg came in smiling, carrying a couple towels. “Thought we might need some extras.”

“Good thinking son.” Dan tucked a towel under Sherry’s ass. “It’s messy. Watch how much she drips.” Dan and Greg watched white slide from Sherry’s very red slash. “Come for girls is clear. Usually watery. Sometimes they squirt. Now, when they get older, they don’t get as wet easily. Then you need lube. It’s not that they aren’t turned on, it’s just what happens to their bodies. But we never stop leaking pre-come.” Dan clapped his hands. “Now that Sherry’s come twice. Should we try a third?”

Greg nodded. “Can I do it and you tell me?”

Dan smiled at his son, “Cock about to burst again?” Greg blushed and nodded. “I bet. I’m ready to go again too.” Only because I’m going to fuck this girl again. Dan sat on the bed with his feet on the floor. “Sherry, this time you do the work. Come spread your legs over my lap. Good, now Greg, you can see her sweet little ass from there. While she rides me you can rub her tits or kiss her or whatever. Slide my cock back inside you Sherry. Good. Oh yeah, good. Now you can-“ Sherry figured it out and began moving up and down. Dan hugged her breasts to his face. “Yeah. Like that.” His mouth grazed over nipples and the fleshy part of her breasts. “Keep rubbing your tits on my face.” Sherry wrapped her arms around his neck while his hands slid to her buttocks. He pulled them apart knowing his son was getting a new view.

Sherry gasped. Greg asked, “You like that?”

“Yeah.”

Dan’s finger was headed toward her untouched muscle when Greg said, “No Dad. That’s mine.” Dan smiled and went back to holding her cheeks open.

Greg whispered in her ear while he rubbed her little anus. Telling her how pretty she was, how he liked her hair.

He curled his fingers into her hair and gently pulled her head backward. His tone changed, “You wanted me to see you naked. You wanted me to touch your tits. Lick them. Make you wet. You wanted to suck my dick and make it harder than it already was. Then you teased me. Said we couldn’t fuck. You made me beg Sherry but you wanted to fuck me just as bad. Didn’t you?” She whimpered and nodded. “And now you’re fucking my Dad. I’m going to fuck you again.”

Dan had enough of this position. Lifting her from his lap he noticed Greg’s finger didn’t want to leave. “On hands and knees,” Dan said.

“Doggy style.” Greg said and took out his finger. “What am I-“

“She can suck your cock while I fuck her.” Greg bounced to the bed, eagerly walking on his knees toward her face. “Don’t shove it down her throat unless you want her to puke. Gagging is all right but puking can ruin her mood.” Greg nodded and stroked her face as he guided his hard on to her mouth. He sighed as it slipped in. “Okay Sherry,” Dan said lining his rock hard cock up with her slit, “welcome to getting fucked like a bitch.” Dan began pumping slowly, letting Sherry get her balance so she didn’t get teeth in his son’s rod. “Mmm Sherry. You’re so tight. Suck my boy well. Treat him like the prince he is.” Greg nodded, his eyes closed as he stroked her hair.

“Will you swallow?” Greg asked. She shrugged. “You should. You should try.” Eyes closed he enjoyed her mouth nursing his flesh.

“Son, if you want, hold her head and use it like a steering wheel. Make her go deeper, or shallower, fast or slow.” Dan watched as his son curled his fingers into her hair and set a slower pace. “Yeah, like that.”

“Ooooh,” Greg groaned. “Good Sherry. Do that again- that-“ Greg shuddered. “Fuck, I’m gonna come. Baby I’m coming, drink it. Swallow.” He thrusted in her mouth, his spunk hitting the back of her throat. Sherry coughed and pulled away so his last few shots got her forehead and cheek. “You okay?” he asked wheezily as he rubbed her back.

“She’s fine.” Dan groaned. “Lie down son, rest. Sherry, drop your head and lick his nuts.” The angle made Dan’s balls tighten. It also made Sherry groan. “Watch son, she’s going to come.” Dan held off, pummeling her until she screamed, her body quaking with an intense orgasm. The little pussy began contracting, Dan moaned, “My turn to blow.” I can’t believe I’m going to fill her cunt again! Dan grunted as he slammed into her a few more times. “Fuck,” he growled as his balls shoved cream deep inside.

Dan collapsed onto her back, reaching beneath her to stroke her tits. “Thanks Sherry. That was a good one.” Dan flopped onto his back. Covered in sweat, his pants still around his ankles. He slipped off his shoes.

“Sherry,” Greg said, “now lick my Dad’s balls.” She hesitated. “Go on. He’s earned it.” Sherry moved to kneel between Dan’s legs. “I want to try what he did.” Greg moved between her legs and slid in easily. “Now it’s mushy in there.” She started to sit up but he patted her butt cheek. “It’s good, it’s good. Just different.”

Dan was in heaven. He’d fucked the girl good and was rewarded with a tongue bath. He couldn’t believe his cock was growing yet again. He smiled when he thought of where he wanted to put it. Taking her by the hair in one hand, he lifted his cock with the other. “Suck me. I know it’s messy but so is sex. Suck it.” Sherry obeyed and started with gentle licks.

She felt Greg’s finger, wet with come begin to rub her asshole. “You like that?” he asked. She nodded as she sucked his Dad’s cock. She gasped when his finger pushed past the tight ring and slowly slid in. He pumped his finger. “It’s hotter than... I think it’s hotter. I’m going to put in another one.” Sherry groaned as the finger pulled out. “If one felt good this..” Two fingers slipped inside. “So tight.” He humped her pussy and asshole making her moan around the swollen rod in her mouth.

“Oh yeah,” Dan groaned, “make noise. It’s good during sex. Especially blow jobs.” Sherry made noise, not to please Dan but because Greg inspired her to do so.

“I’m going to put my cock in your ass.” She froze. “My fingers didn’t hurt. It won’t.” His fingers pulled out.

Sherry let go of Dan to balk but Dan was instantly on his knees, pushing his cock into her mouth. Her protests were muffled by his dick.

“Greg won’t hurt you Sherry. Let him break you in proper. He’s had all of you so far, don’t stop now. Focus on sucking me.” With his hand on her head he carefully thrust in her mouth. “Yeah, think about this. Mmmm.”

Greg ran his fingers up her leg, scooping up fluid and wiping it on his stiff flesh. “I’ve had all your virginity once I do this,” he said. “Okay,” he spit on her hole, “I’ll be careful.” He wasn’t too careful. Once the head of his dick popped in he couldn’t help but shove it in all the way. Greg groaned with pleasure. Sherry cried out with surprise and a hint of pain.

Dan pushed firmly into her mouth, gagging her. That distracted her for a moment. Once Greg took a breath, he began wildly fucking her. Fingers digging into her hips, rabid with sensation. The energy in the room changed into something animal.

“Fuck her ass son,” Dan hissed, blood thudding even harder in the veins of his shaft. “Fuck her good.”

Greg was deaf. Sherry grunted every time he fully connected. Greg started chanting, “I’m fucking your ass. I’m fucking your ass Sherry. I fucked your mouth, your pussy and now your ass. I fucked all of you.”

Dan marveled at the raw fervor of his son, and was envious. His cock was incredibly rigid with the show he was getting. He wanted the same piece his boy was pegging. He slowed Sherry’s sucking, making long and slow strokes. He wanted to blow his wad in her butt not her mouth.

Greg’s face pinched and he growled, “I’m coming in your ass! Your virgin ass!”

Dan was worried that Greg’s holler might wake his mother. But Dan didn’t care, he was feeling like an alpha male caveman. He’d knock her to the floor and fuck her ass if she interrupted.

Greg gurgled gibberish as he filled her dark pipes. Panting, he fell off of her and onto his side.

Dan pulled his cock from her mouth and moved behind her. Sherry was dizzy with sex, not sure what was happening. Dan’s cock pushed into her asshole which was somewhat stretched out. He felt the tight walls close in around his cock. He stood her on her knees with her back against his chest. Rubbing her clit with one hand, he rubbed her tit with the other as he gently fucked her ass.

Greg watched with interest even though he was wilted. “I want to try something,” he said. “Move your hand Dad.” Greg pushed his Dad’s hand away from her clit and moved his face close.  He picked up a towel and wiped the mess of fluids off her clit. “I’m going to lick your pussy. You licked my cock, I owe you.” That said, he buried his face into her cunt and flicked her clit.

Sherry was unraveling. Her nerves vividly alive, overloaded with sensations. She could hardly breathe. Greg’s tongue was on target, flicking her just right. When he slid a finger into her pussy she whimpered.

“Yes Greg, yes,” she panted. She held his jaw, supporting his head while he licked her. “You’re so good at that.” She could feel him smiling on her palm.

Dan was pinching her pink nipples, making her writhe even more. “You think you’ll come again?” He whispered in her ear as he fucked harder.

“Don’t know.”

“I will,” Dan chuckled. “Fucking your sweet little butt. I’m going to come hard.” Dan felt her body start to tighten. “You are going to come, you sweet little thing. My boy licking you right?” She nodded. Dan was nearing the edge. “Son, I’m going to start fucking her hard, use your hand on her clit.” Greg sat up, Dan set Sherry onto all fours and waited for Greg to find her clit again. He found it and began rubbing her tit with his other hand. “Good job son. Drive girls crazy. If they find out how good you are you’ll be very busy.”

Greg grinned and rested the side of his face on her shoulder. He whispered to Sherry, “I just want you Sherry. I’ll make you come anytime you want. Okay?” She pecked a kiss on his forehead, they smiled.

How sweet, now I’m going to fuck the sweet right out of her. Dan thrust hard making her back arch. Oh yeah, you’re going to walk funny all day tomorrow. He thrust again and again while Greg worked his hands, making her cry out his name. Greg liked it and kissed her neck.

“Hope she’s close son, I’m about to cream her asshole.” Greg sat up, letting go of her nipple but still working her clit. He saw his Dad spread her cheeks with his massive hands and watched his froth covered cock slide in and out of her hole which seemed to try to pinch him. Greg watched as he fucked her harder and faster.

Sherry groaned, it was Dan’s cue. He was stunned he felt he could come again, he wasn't exactly young but he knew there were a few drops left. “Rub harder son. Faster too.”  Sherry broke out short, loud moans. “She’s coming. My turn.” Dan was screaming in his head, I’m fucking the babysitter’s ass! Fucking my son’s girlfriend! My wife’s asleep while I’m buttfucking the sitter! I’m filling her tubes with come! Her tight little ass has been broken in!

Dan roared as he came for the third time that night. Gasping for air, he kneeled in place, using his hands to pump her hips. Making sure his balls really were empty for the night, maybe empty for a week. Finally, he pulled away and settled on the floor, letting the love birds kiss, cuddle and coo.

Dan sighed and asked Greg for the phone. Greg reached to his desk and tossed him the cordless.

Dan dialed and waited. “Good evening, this is Mr. Wells. Sorry to call so late Mrs. Cage, but Sherry’s deep asleep in our guest room and I don’t have the heart to wake her.” Greg hung his head over the edge of the bed, grinning widely at his Dad. “We’ll bring her home in the morning. After breakfast. All right. Good evening to you. Goodbye.” He clicked his phone shut and smiled at his son. “Well, kiddo. Make sure you lock your door. I’ll go unmake the bed in the guestroom so your Mom thinks Sherry slept in there.”

“Thanks Dad,” Greg’s eyes were bright with admiration. “You’re so cool.”

“I’m just glad to have gotten a fuck like that. Never thought it’d happen. So thank you son, Sherry. And congrats on your new girlfriend.” Dan stood, tucking himself back in his pants. “I’m going to shower and go to bed. I’ll give your Mom a sleeping pill. She’ll sleep past noon that way. And I’ll send the little ones to the neighbor in the morning. You can have the morning together.” Dan smiled, “Oh, you two should take a shower together. You’ll love it.” He kissed each one of them on the forehead and went to his room.

And maybe, I’ll join you in the morning to teach you a couple more lessons.