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His Partner’s Sister

Category: Anal Sex
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It wasn’t hot enough for the outfit she was wearing. You didn’t have to be a brain surgeon to know she was dressed to impress, and Derrick would have been less than a man if he hadn’t let his eyes wander over the delicious curves of her body. He watched as she strolled down the concourse, and wondered how her outfit had gone over on the plane. Everyone else that filed out behind her was dressed conservatively.

The women who passed her, in a hurry to get where they were headed, gave her outfit a ‘she must be easy’ glare; their husbands’ jaws were still on the ground. Considering the flight was over four hours long, it went without saying they loved everything she wasn’t wearing.

He supposed he shouldn’t be starring at her chestnut hair that hung, in sexy curls, almost past her tiny skirt. He knew for certain that starring at her mouth was out of the question. It made him think of all the dirty things she could be doing with it. Her lips were painted with a liberal smear of red gloss, but even that didn’t look quite as trashy as her outfit did. Her legs were endless. He wanted them wrapped around his hips in surrender. His groin tightened, and blood pumped between his legs; He wanted her. Derrick groaned slightly, and shifted his eyes from her fair complexion–before the bulge in his pants became noticeable to others. If he didn’t have other pressing issues right now, he would have made it his objective to have her face down, ass up, in the middle of his king size bed. Under these circumstances, he’d have to let the fantasy go.

He wasn’t here to find someone to fill his bed, though god knew it had been empty of late. He was here to pick up his partner’s little sister. He glanced at the picture he had forgotten was in his hand, and scanned the passengers coming his way again. There was no one who looked like her on the plane. The picture was a few years old, but no one could change that much, could they?

Scowling, he wondered how he’d ended up here anyway; John was supposed to be the one waiting in the airport, but he’d gotten laid up, or literally laid, and passed this job on to Derrick with a, “You know how hard it was for me to get her to bed.” mumble.

He had pressed the photo and flight itinerary in Derrick’s hand, and shut the door. So here he was waiting for his partner’s little sister, and salivating over a woman he had never heard speak. Derrick lifted his eyes to the ceiling for just a moment, but that was long enough. When he brought them back down she was there. She came to a stop right in front of him and with a smile that made him think it actually was hot enough for her outfit, and held out her hand for him to shake.

“I’m Leslie. You must be Derrick, right?” Her voice was quiet, but it had the power to make him want to strip her there in front of millions of people.

Taking a metal step back, Derrick held back a groan and simply offered, “You don’t look anything like your picture.” He held up the photo for her inspection.

Leslie laughed and Derrick felt his pants get tighter, “Oh my God! I think I was fifteen in that picture.” She laughed again.

Derrick refrained from pointing out she was closer to fifteen than she was to twenty-five, even if she was legal now.

“Well maybe we should get out of here,” Derrick shouldered away from the wall he’d been leaning against for well over thirty minutes, and took the small suitcase, he hadn’t noticed before, from her hand. Leslie smiled, “What a gentleman,” she rested her hand on his arm, and her green eyes that looked into his, had ‘take me to bed’ written all over them.

Derrick knew his muscle flexed under her arm, but didn’t say anything as he led the way out of the airport. He needed to get her into his car and to John’s house before he did something stupid– like drive to his house and fuck her until she couldn’t breathe or walk.

When they reached his car she let out a low whistle and ran her hand lovingly up the side of his black Mercedes, like she might caress a lover. God what he wouldn’t give to be his car at that moment. Her hand ran itself tenderly up the side, sliding over the sleek surface with reverence. Derrick almost shook with his need. He rested his own hand on the trunk to steady himself, and pushed the button to unlock the doors. She gave a little jump when the car doors unlocked and laughed self consciously.

“Sorry I’m not used to locking my car back home.”

Derrick eyed her over the top of his car, and wondered what she was used to back home. Was she used to boys who didn’t know the first thing about making a woman cum? Was she used to quick and sloppy back seat sex that was over before it started?

“Get in!” His voice sounded like someone had run it over a cheese grater and he grimaced.

If she were more experienced she’d know without asking that he wanted her on top of him, under him, or just any way at all as long as he was deep inside of her feeling her climax around him, feeling his cum shoot into her body. He jerked his door open, and got inside shutting it with too much force.

Leslie looked at him in surprise, “Is something wrong?”

He almost laughed at the question. Everything was wrong! His dick hadn’t been this hard for years, if ever. He’d never thought about sleeping with a nineteen year old before, and the one he’d happen to fuck in a heartbeat was John’s little sister. Everything was horribly wrong. He didn’t answer her; he started his car and backed out of his parking spot. He needed to get away from her before he flipped up that non-existent skirt, and showed her how a man fucked a woman. He was almost certain she didn’t know. Once on the freeway he glanced her way to see her staring out the window in fascination.

“I’ve never been to New York before.”

Derrick knew that already. Leslie was just trying to make conversation because she was nervous. She’d never actually met him, and he was being an asshole. He took a mental step back and took a stab at normal conversation.

“How long will you be here?”

Blinking, like someone who’d just come out of the fog she looked him over, “I’m staying, didn’t John tell you?” He may have, but Derrick didn’t remember him mentioning it.

“You’ll love it here.” He didn’t answer the question, but he glanced at her out of his peripheral vision.

She smiled at that and ran a palm up her thigh, which was beaded with cold chills.

“You really should have dressed for winter in New York.”

She raised her eyebrows in question.

“You look cold.”

Leslie rubbed her hand up her leg again, “It isn’t the cold that’s giving me chills.”

She pinned him with her bedroom eyes and a lazy smile. The car swerved, and Derrick looked at her like he didn’t believe he’d heard her. She couldn’t mean… her hand went to his crotch, and covered his hard flesh showing him she did mean exactly what it had sounded like.

“I’ve been waiting to ‘meet’ you for a long time.”

Derrick didn’t miss the hesitation around the word meet, and he glanced down to see her running her hand over his cock slowly. He knew he was hard enough to do more than please her, probably numerous times. He knew this wasn’t the best option, but with one caress she’d made it his only one; he didn’t care if she was John’s little sister anymore. He grabbed her wrist with his eyes glued to the road. He moved it back to her thigh, and saw the disappointment she couldn’t hide and had to stop himself from smiling. Hesitating just long enough to make her squirm, he ran his hand up her thigh until it rested just underneath the edge of her skirt. Her breathing hitched, and she glanced at him with lust in her eyes.

“That’s enough… for now,” But he didn’t make any effort to move his fingers from her thigh.

She looked him over curiously; a little nervous shiver ran through her body. Derrick smiled and set about driving to his condo. John could wait. He probably needed to rest after last night anyway. Derrick, on the other hand, was ready to explode. When they pulled up at his apartment she had the door open, and was waiting for him to come around the car. She shivered as he took her arm and led her past the doorman, who looked her over and gave Derrick a knowing smile.

“Have a nice day Mr. Larsen.”

Derrick waved him off, and gently pushed Leslie toward the elevator. Once the door had shut and he had pushed the button for the top floor, he pushed Leslie against the wall and put one arm on each side of her head. He leaned close enough that he could feel her breath on his neck, but wasn’t touching her.

“You know when we get to the condo I’m gonna fuck you, don’t you?” Leslie’s breath came out in a rush, and she fidgeted a little but didn’t back down. She looked him straight in the eye.

“That’s what I was hoping for.”

He grinned and brought one hand down to fondle her barely covered breast. “You’ll be lucky if you can walk when I’m done.”

The elevator came to a stop and Derrick herded Leslie into his house.

As soon as the door shut he picked her up, “Wrap your legs around my waist,” he headed toward his bedroom, “I want to feel that wet pussy against my cock.”

He heard her quiet moan and gripped her ass in both hands, “Your pussy is wet isn’t it?”

She almost didn’t answer; he felt her hesitation before she nodded and buried her face in his neck. He chuckled and walked into his bedroom. He walked to his bed, and let her slide down his body to land on his comforter. She fell backwards, her glorious hair sprawling around her on the bed, and her legs spread reveling for the first time she wasn’t wearing any panties.

Derrick groaned and lowered himself to the bed on top of her.

“Fuck Leslie, you pussy looks like it tastes great. Does it?”

She buried her face in his neck again but he pushed it back and looked into her eyes, “Does it?”

She lifted her shoulders to indicate she didn’t know, and Derrick’s dick got even harder.

“You’ve never tasted yourself?”

She shook her head slowly as Derrick’s hand went in-between her legs to feel the juices her pussy had spewed forth to ready her for his taking. Looking her in the eye, he pushed two fingers inside her tight cunt slowly.

“Before we’re done here you’ll have tasted yourself.”

She shivered from a wave of pleasure, and Derrick pushed her down on the bed and spread her legs wider in one smooth motion. He watched his fingers slide in and out of her freshly shaved cunt. He could hear her cries and moans as he pushed harder, invaded her deeper, then added two more fingers. She groaned at the invasion because she wasn’t ready for the added girth, and he slowed his movement till she was again moaning and heaving her body towards his fingers in earnest. Looking over her scantily clad body and then back to her pussy, Derrick knew he had to taste it. He pulled his fingers out of her cunt and quickly pulled her skirt over her hips, and off her long legs. He didn’t look where he threw it; he pulled her to a sitting position, and got rid of her shirt too.

His hands went to her tits for a moment, but not too long. He flipped her over onto her hands and knees so he could see her red pussy dripping wet, and her tightly closed asshole. He knew without asking that no one had invaded her there yet. He would change that though, he knew looking at that hole that he would fuck all three of her holes today. He reached into his bedside drawer for the bottle of lube he kept there, and set it beside them on the bed. Leslie looked at it curiously but didn’t question him.

Having everything he needed at hand, Derrick bent toward her pussy. When he was close enough she could feel his breath on the lips of her cunt, she moaned softly. He began to lick her in earnest, not giving her a chance to work up to it. He threw her into a kaleidoscope of sensations, and she came apart as soon as he inserted his fingers again. He felt her climax around him, her muscles grasping at his fingers over and over. When her orgasm let up he pulled his fingers from her pussy, and let her slide to the bed in a gasping heap.

Standing, Derrick undid his belt and unzipped his pants. Leslie rolled over to watch him tug off his shirt, and push his pants off his legs. When he stood again he was naked, and his cock was protruding proudly away from his body. He saw her eyes widen a bit and she smiled softly. Coming down on the bed he slapped her tits so they swayed back and forth on her chest. He shoved his dick in her face, and she took it in both her hands. Derrick let his head fall back as put her lips around him, and began sucking his cock in earnest.

“Ummm babe, you sure know how to suck a cock.”

She looked up at him with her lips around the head of his cock.

“Deep throat it Leslie. I wanna feel my cock hitting the back of your throat.”

Leslie did as she was told and was rewarded with his growl when he felt his dick hit the back wall of her throat, and keep going until it was as far down her throat as it would go. He grabbed hold of her long hair to hold her there for a minute, and when he let her go she came up gasping for air. Derrick reached down to hold her tits as she took him into her mouth again. Her tight throat was getting to him fast; she pulled him out of her throat to look at him for a second. His dick was rigid, wanting relief; a drop of pre-cum was sitting on the tip. Leslie leaned forward and licked it from his head, and hummed her approval. He almost came in a rush, and pulled himself out of her mouth before he lost it.

After a moment he was back in control and he moved over her and in between her legs, “Open your legs babe. I want to be buried inside you.”

Her legs fell open at his words, and he climbed on top of her placing the head of his cock at her pussy entrance. He gripped the base of his cock in one hand, and slid slowly inch by inch inside her. She was so tight; they were both groaning by the time he was inside her all the way.

He began moving in and out of her, picking up his pace as her body slowly began to stretch and accept him better. When he was going at a steady pace he stopped, slid out of her body, and flipped her over onto her hands and knees again.

He slid back into her dripping wet pussy in one fluid motion and pulled her into him with force, “Do like my cock inside you Leslie?”

She moaned her answer and he slowed his pace, “what was that? I didn’t hear you.”

She gave a frustrated cry, and tried to wiggle down his dick but his hands held her firmly in place.

“Do you like my cock inside you?”


He smiled as her scream filled his bedroom and let her drop back onto his cock, and started fucking her hard again. She was delirious; he could tell she was close to an orgasm. Picking up the lube, he squirted some into his hand but she didn’t notice. When the cool liquid hit her asshole she froze. He ran his other hand over her back to reassure her, and used the hand with the lube on it to run over her asshole. He kept moving inside her pussy, but worked her asshole though she tried to squeeze it shut. He could hear her groan as he forced his finger into her asshole, and it tried to push him back out. He felt it slip past the muscles that were trying to push him out, and even though she was whimpering he felt her convulse around his dick. Groaning, he held back his own release and pulled his cock from her pussy lips. He pulled her around a little roughly by her hair, and shoved his cock back into her mouth making her look at him as she tasted herself for the first time.

“See sweetie, you taste good.”

She moaned around his cock sending vibrations up and down his cock, while she lapped herself off of him. Pulling out of her mouth wasn’t an easy thing to do, but Derrick wanted his cum seeping out of her asshole when this was over. He let her head go and moistened himself with some lube, as well as her asshole. It tightened up again, and he smiled knowing he would be invading that hole within minutes and her muscles weren’t about to keep him out.

“I’m going to put my cock in your ass now Leslie.”

Her eyes flew to his in horror.

“Don’t worry sweetie, I won’t do anything you won’t like.”

She eyed him warily as he placed the head of his cock at her entrance. Smiling, Derrick slid her own hand around her to find her clit and stroke it. Soon she moved her hips like she had a cock inside her, and moaned again. Derrick moved his hand back around to open her ass cheeks wider, and placed his other hand at the base of his dick. Pushing slowly forward, he began invading her. Her muscles were trying their hardest to push him out, and her legs were shaking underneath her. Frustrated tears seeped out from beneath closed lids, as he reached back around to play with her clit again. She relaxed a little as he played with her clit softly, and he was pulled deeper into her asshole.

Giving a little screech she moved her hips to get away, “You too big for me!”

Derrick grinned, “That’s okay babe, if you don’t want me in you then use your muscle to push me out.”

Leslie did as she was told and in one fluid motion, Derrick had slid all the way inside her.

“Fuck babe, your ass is so tight,” Derrick gave her a moment to get used to the feel of him before he began to pull out a little way, and then pushed himself back inside her.

He felt her legs give out, and held her up so that he could continue to fuck her asshole.

“I’m going to make you come this way Leslie.”

Leslie sighed at his words and he chuckled. She liked the dirty talk.

“Only sluts come this way Leslie. Are you my little slut?”

Leslie nodded and shrieked her approval, as Derrick started pounding her ass in earnest.

“Come on slut I wanna give you my cum. Sluts like you want all the cum they can get don’t they?”

Leslie shrieked and came apart, as Derrick continued to pound her ass. It only took a few more thrusts as Derrick had a hard on for way too long, and the cum in his testicles was more than ready to be flushed out. He jerked himself as far as he could get, and let his come hit her insides in spurts. Letting her go, they both fell to the bed. Derrick looked her over, and knew this wouldn’t be the last time he fucked Leslie. He wanted to come in every hole he could fit into on her body.

Running his hand slowly over her tits he looked into her beautiful green eyes, “Fuck I’m glad you’re staying in New York Leslie!

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