Guest House

Dylan Raport drove his beat up Honda up the sprawling driveway. Parking out front of the affluent house, he got out and knocked on the door. A well-dressed middle aged man with salt and peppered hair answered the door.

"Come in. You must be Dylan," the man said, stepping aside to let him in.

"Thank you," Dylan replied, stepping into the spacious estate.

"I'm Carl. Can I offer you a drink?"

"Thank you but I'm all set."

"All business I see," he said and walked over to the liquor cabinet, clinked two ice cubes into a glass, and poured in some scotch. "I suppose that you want to see the guest house?"

"If it isn't too much of a bother. I have some clients I need to see this afternoon."

"What do you do?" Carl asked, as he opened a sliding glass door that led to the swimming pool.

"I'm a photojournalist. Mostly for the local papers, weddings, and magazines. You know, free-lancing."

They walked beside the pool, opened a gate, and approached a two story building. Traversing up a staircase that ran along the side of the building, Carl fumbled for a key and opened up the door.

"Well this is it," he said and they stepped inside.

It wasn't big, but it would do, consisting of one large room with a king size bed, a sink, fridge, and a small standing shower.

"It's perfect," Dylan said. He pulled out an envelope that had the first and second months rent and handed it to him. Carl didn't open it and just put it in his jacket pocket. "I don't have much to move, just some clothes and stuff for my work."

"Not a problem, you can park in the garage underneath and private entrance so that you can have as much privacy as you want."

"I can't thank you enough," Dylan replied and they shook hands, cementing the deal. Carl dropped two sets of keys into Dylan's hands.

"I'll leave you to your business."

Dylan returned to his new pad a little after seven at night. His clothes and cameras filled his Honda. On his second trip up and down the stairs, he smelled cigarette smoke. He turned to find a young woman, probably 19, puffing away and eyeing him.

"So you're the new guy," she said. Her blonde hair was tied back and she wore a tight tee-shirt and yoga pants that hugged her curves. She eyed the box of cameras. "What are you, some kind of pervert?"

"No. Just a photographer," he said and gave her his best smile. "And you must be?"

"Samantha." She finished her cigarette and flicked it to the side.

"It's nice to meet you, neighbor."

He walked up the stairs and dropped the box off. When he returned a stunning woman stood next to Samantha. She saw Dylan and came up to him. She was an absolute knock out. Long blonde hair, big breasts, and she had a sultry sway to her hips. Her heals clicked on the driveway as she approached him.

"You must be Dylan," she said and gave her his hand. "I'm Cindy, Carl's wife."

"Glad to meet you. I want to thank you for renting this place out to me on such short notice."

"No problem. It was just sitting there ever since Tara went to college. I wanted to extend an invitation for dinner."

"I'm sorry but I already ate," he said and dangled an empty Taco Bell bag from box in his hand. "Thank you though."

"Well if you need anything, please feel free to knock."

She gave Samantha a quick stare and they both headed through the gate, but not before Samantha turned around and caught Dylan checking them out. He quickly walked up the stairs.

Exhausted, Dylan sprawled out on his new bed, reading a book when he saw a light go on in the window next door. From his vantage he could see into Samantha's room. She wore a matching set of pink bra and panties. Dylan quickly shut his light off and watched her unhook her bra, displaying two pert breasts. She then crawled over the end of the bed showing her barely covered ass in lacy underwear. He stroked his now hard cock, watching her go under her bed and reach for a laptop and a vibrator. She flipped it open and began rubbing the vibrator over her pussy. She writhed to a climax and Dylan had to stop stroking his own cock before exploding onto the bed. She reached over to her stand lamp and turned it off.

Dylan was a morning person and had risen just before five in the morning to go running. It was his first time checking out the neighborhood which was filled with monolithic structures of decadence. High end cars passed him on their way to doctor's offices or corporate high-rises. After his hour long run, he ran back up the drive way and saw Carl placing two suitcases into the back of his Mercedes Benz.

"Need help with anything?" Dylan asked.

"All set. How's the guest house?"

"I can't thank you enough. It's perfect. Heading on a trip?"

"Insurance seminar over in Spokane," he said and closed the trunk. "Got to hurry in order to make the plane."

"Have a safe trip," Dylan said and jogged back to the house.

He turned off the hot water to the shower, grabbed his towel that hung over the shower door and wrapped it around him. When he opened the door, he saw Samantha holding a picture. She was wearing tight blue shorts that read Pink on them and a matching sports bra. She eyed him as she put the picture back.

"Is that your mother?"

"Yes. What are you doing in here?"

"Being friendly."

"That usually means knocking before coming in."

"I did but I guess you didn't hear me." She ran her finger down his desk eyeing the pictures. "What are you working on now?"

She leaned over to a picture at the far end of my desk and her shorts rode up to reveal the bottom curve of her ass.

"I'm putting together a wedding album and some pictures for the local nature magazine."

"Were you up late last night?" she asked and turned around, leaning against the desk.

"I turned in pretty early. Do you mind giving me some privacy. I need to get changed."

"Don't mind me."

"I kind of do right now," he said and ushered her towards the door. He opened it with one hand and guided her out with the other but just as he was about to close the door, she grabbed the end of the towel and yanked. He slammed the door closed and her eyes bulged in surprise, leaving her outside holding the towel. That girl is a wild-child, he said to himself. He hurried to get dressed. He needed to meet his client in a few hours or he'll be out of a few hundred dollars. He buttoned up his dress shirt, combed back his hair, and started assembling the wedding album that he needed to bring to his client. When he had all the pictures in there proper place, he put the album into a manila envelope, and headed out.

He opened the garage door and started up his Honda but as he backed out something didn't feel right with the car. He stopped in the driveway and got out and noticed his back two tires were flat. Great, he thought. Behind him a white Volkswagen beeped and Samantha ran out of the house with his towel over her shoulder. She saw him looking at his car, said something through the window to her friend, and then came over to him.

"Is something wrong?"

"I've have two flat tires and need to get downtown to drop this off," he said, holding up the envelope.

"We can give you a lift."

"That's alright. I'll call a cab."

"Don't be a fool and I'll be on my best behavior," she said and gave him a mischievous smile.

"Damn it. Okay."

She skipped back over to the car and leaned into the passenger window and he couldn't resist staring at her assets. When he walked over, he saw two teenage girls in the front seats.

"This is Dylan. He's renting the guest house," she said and they smiled at him.

"Sorry to be a bother," he said as Samantha opened the backdoor and slid in. "I just need a lift downtown near Belvadeer's Bridal Shop."

"No problem," said the driver, a cute brunette girl wearing a white tank top that showed off a yellow bikini top underneath. "I'm Ashley. Hop in."

They backed out of the driveway and towards downtown, blaring John Mayer. Samantha leaned over the middle console and skipped a song, but in doing so put her ass right in his face. He fought himself to not stare and looked out the window.

"So what do you need to do downtown, Dylan? Getting married?" asked Ashley. She smiled at him through the rearview mirror.

"I have to drop this photo album off for them. They hired me to take some photos for one of their weddings."

It was a fifteen minute drive and Samantha was true to her word and remained well behaved. They pulled into the parking space in front of the bridal shop and Dylan got out.

"Thanks for the lift. I'll take a cab back," he said and headed into the shop.

He met Mr. Belvadeer and they quickly exchanged the envelope for a check. When he grabbed his cell phone to call for a cab, he noticed the Volkswagen still idled in the parking spot. He walked out and Samantha stuck her head out the window.

"Come on. We'll drive you back," she said.

He turned the cell phone off and got back in.

"Thanks. I owe you one." For some reason all three girls had wide grins like they were trying to hide something but before he could protest, they sped out of the parking lot blaring pop tunes.

They drove for a ways and came to a stop outside a house. They beeped the horn and a thin girl carrying a towel and a handbag rushed out the door, piling into the car and sandwiching Dylan in-between the two.

"Whose the guy?" the new girl asked as they sped away.

"He's a friend of mine," Samantha said.

When they stopped at another house and beeped the horn, Dylan knew something was up. A pretty girl ran out and opened the door. Samantha rose off the seat and planted herself right in Dylan's lap. He didn't have time to adjust and his cock and it pinned under her ass.

"Whose he?" asked the new girl.

"He's Samantha's new boyfriend," said the thin one and before he could argue, Ashley turned up the radio and hit the gas.

The girls bobbed heads to the music and Samantha began gyrating her hips. His cock instantly responded and pressed up against her ass. She leaned back so that their faces were side by side and said, "Seems like your big friend likes me." She then bit my ear.

"You promised to behave. You're going to get me kicked out of my new place."

"I am behaving. Plus I won't tell if you won't," she whispered and grinded her ass into his cock.

He noticed that they were heading in the opposite direction to his place.

"Where are we going?" he asked.

"Just going swimming."

"Damn it, Samantha. I've got things to do. My car needs to get fixed."

The car came to a screeching halt as the light ahead turned red and he grabbed Samantha by her slim waist, his forearms touching the underside of her breasts. She slammed back down on his lap and squirmed back into position.

"Don't be a party pooper," she said. "You can have a little fun can't you." His erection slid up and down her ass and she took his hands to her breasts. "Besides, you seem to be enjoying yourself already."

"You're going to get me in trouble."

"You're a big boy," she whispered in his ear and bit his earlobe again.

They pulled two wheels onto a sidewalk next to three other cars. As they piled out, bass blared from the back of a up-scale home. Samantha grabbed his arm and dragged him up the driveway and behind the house. The backyard had an enormous pool with a water slide, a diving board and a hot tub. A few eighteen year old boys and girls played in the shallow end of the pool and a radio on the deck blared tunes. Dylan felt out of place here in his dress clothes. Samantha led him to a set of girls that were sipping on a drink through a straw.

"Hey Tracy," she said. "This is Dylan."

She tipped down her shades at him. Her white bikini with black polka dots could barely contain her enormous breasts "He's cute but a bit over dressed."

"I didn't know I was going swimming," he said and glared at Samantha.

"Can he borrow a pair of your brother's swim trunks?" she asked.

"Sure. You've know where to look."

"Thanks, Tracy," she said, hooking her arm through his and they went inside.

The large house was decked out with statues, fancy paintings, and expensive looking vases. Samantha slid her arm from his and rushed up the stairs. He couldn't help but stare at her ass in her brown bikini bottoms. She did have one of the best asses he had ever seen. She got to the top of the stairs and looked back, grinning. They entered a teenage boy's room. Tony Hawk and various heavy metal band posters plastered the walls and anime models lined several shelves. After rifling through several drawers, she threw him a pair of swimming trunks. He held them up and picked the biggest pair. The one with skull and crossbones on it.

"Well?" he asked.

"Well what?"

"Are you going to leave so I can change?"

"No," she said and leaned against the door. "I missed out on it the first time."

He took his digital camera, that he always carried in his pocket, and wallet and set it on the dresser. He then unbuttoned his pants, pulling them down. Samantha moved from the door and closer to him, putting her hands on his boxers. She looked up into his eyes as she pulled them down. His cock sprang out, smacked against her belly and she wrapped both hands around it.

"I don't think we should..." he tried to protest but Samantha kissed him, darting her tongue into his mouth. Their tongues danced and she stroked his cock. She then got down on her knees and flicked her tongue over his tip. He moaned, leaned back against the dresser and closed his eyes. She then took his mushroom tip into her mouth and ran her tongue in circles over it.

"This is a monster," she said and then put the first inch back into her mouth. She worked her head back and forth but could only take a quarter of his cock before she gagged. His body tingled and he knew that he was on the verge of cumming, so he pushed her back. He grabbed her shoulders, lifted her to her feet and turned her around. Pushing her head down to the bed, he moved behind her. Her beautiful bikini clad ass wiggled at him. He pulled the bottoms down and ran his massive cock up and down her slit. She moaned as her pussy juice glistened his manhood. The tip of his cock pulled her lips apart and as he was about to thrust into her a knock came to the door.

"Samantha are you in here?" asked Tracy.

"Yeah. We found some swim trunks and he's putting them on," Samantha said. She stood up and put her bikini bottoms back on.

Dylan pulled his swim trunks on, pinning his hard on into the elastic band of the trunks and put his undershirt over it. Samantha opened the door and Tracy looked at her suspiciously. He grabbed the camera, stuffed it into his pants pockets with his wallet and key and followed the girls down the stairs. He found a nice spot to stash his clothes and went to the pool. He needed to get into the water and cool down his hormones. He went into the shallow end of the pool and submerged himself. When no one was looking he readjusted his penis and relaxed. Ashley floated by on a raft.

"Hey there," Dylan said. "I wanted to thank you for the lift."

"No problem," she said.

All of a sudden a boy cannon balled off the diving board and Ashley tipped over. Dylan instinctively reached out and grabbed her before her head could go under. The raft flipped and drifted away. She reached it and pushed it over the side of the pool, but in doing so, pressed herself against him. Her breasts squeezed against his chest and when she turned around, she rubbed her ass against his groin. She gave his dick a squeeze before moving away.

"Samantha wasn't lying," she said and walked up the steps. "Come on, let's go in the Jacuzzi."

He followed her. There were two other boys in the pool already and Ashley sat between Dylan and one of them. They eyed him and made him a bit nervous.

"Whose this guy?" asked one of the boys.

"Samantha's friend."

"Is there room for us?" asked Samantha. She had Tracy, a boy, and the thin girl with them.

The boy didn't wait for an answer and dropped in, making Ashley have to get up and sit on Dylan's lap. Samantha got in and sat on the boy's lap to Dylan's right and soon each boy had a girl on their lap. The music blared and the Ashley began wiggling her ass on his cock as she danced. Soon all the other girls began dancing like strippers. Dylan's cock throbbed and Ashley reached out, stroking it under the water. When the music stopped, Samantha pushed Ashley off of him.

"Time to switch spots," she said and each girl moved clockwise to another lap.

The music started up again and Samantha turned around and straddled Dylan. One of the girls followed suit. Samantha slid her pussy up and down Dylan's rod and smashed her mouth against his, driving her tongue into him. Their tongues battled each other. With one of her hands, she ripped open the Velcro on his shorts and snaked his dick out. Dylan had to scoot down to give her room. He broke his kiss and stared up at the sky as she jerked him off. Samantha was about to turn around when the music stopped and Tracy shoved her off his lap and she reluctantly climbed onto the lap of the boy next to him.

Dylan tried to fish his cock back into his shorts, but the nubile girl straddled him. When her crotch felt his girth against her, her eyes widened and she almost gasped. Then she smiled, pinched both his nipples and began rubbing herself on him. Samantha was putting her tits in the face of the shocked teenage boy and Ashley wiggled her body against the kid opposite him, but eyed Dylan hungrily. Two hands rubbed the top of Dylan's mushroom tip and Tracy ran her womanhood up until it met her hands. She let out a moan as the fabric of her bikini began to stretch, stopping his cock from entering her. She rose up again and he grabbed her glorious tits and squeezed them together. He pinched the nipples between thumb and forefinger and she shivered as she lowered herself back onto his cock, but this time she had slid her bikini to the side and he felt her warmth even through the Jacuzzi water.

He was about to impale her when the music stopped and Samantha quickly got off her partner and onto the next, moving the line of women around, but Tracy needed a bit more incentive before she reluctantly left. The thin girl with small breasts hopped onto Dylan's lap, she let out a yelp.

"Holy shit," she said and the boys stared at him and Dylan shrugged. All three girls smirked. The thin girl turned around and her hair fell in his face. She rubbed up and down his shaft and he held her waist. She shivered with enjoyment as his thick member rubbed against her. The boy next to him had lowered Ashley's bikini and two perfect nipples popped out between his fingers. The thin girl was a bit shier than the others and merely jerked him off until the next song began.

Ashley wasted no time and nudged her out of the way. She turned around and pinned her ass against his exposed groin. She slid her ass crack up his shaft until his cock popped up between her thighs. She pinned it there and grabbed the head with both hands, gently twisting and turning her hands over it. He bit his lip and concentrated on not blowing his load. She then slid forward and forced his hard-on down. She was on his knee, his cock pushing up on her womanhood and she began moving back and forth in short thrusts.

As soon as the song ended, Samantha pushed her off of Dylan. She wasted no time and grabbed his dick under the water with one hand, pulled her bikini to the side with the other and slid his member into her. Her pussy clenched as his cock tried to fill every inch of her and she eased herself down into his lap. He reached in with his right hand and rubbed the top of her clit. She moaned and slowly began bobbing up and down on his shaft. Water splashed in his face and he had to control himself with the tightness of her. She bit her lip to not scream in ecstasy as his cock engulfed her. Her nails dug into his thighs as she climaxed. He was about to join her when Tracy pushed Samantha off of him before the music had changed and Samantha fell into the lap of the boy next to him.