Adventures of an American Girl Ch. 01

Anal

Jennifer – or Jenni, what essentially everyone called her – was a woman in her late 20’s. She lived by herself in Pittsburgh, PA, worked as an accountant and worked out in her spare time. Jenni liked to think she’d won the genetic lottery; she had a beautiful face, soft skin she tanned as often as she got the chance to, and wavy brunette hair going down to her chest.

Unfortunately, Jenni knew she had a weak spot; her horniness could easily get the better of her. She simply couldn’t be stopped when she was on the hunt for sex. And as a single woman living in a city filled to the brim with sleazy blue-collar workers, that became quite often

To help her even further, Jenni had grown a big ass during puberty. Calling it a bubble but wouldn’t be an understatement. What’s more, she decided to get a boob job as early as 19. Before, she was almost flat-chested and couldn’t wear anything larger than a 34A bra. After the surgery her boobs became much bigger and rounder, and took her bra size up to at least 34C. She’d deliberately gotten them to look fake – Jenni had always wanted a pair of proper bolt-ons.

Jenni’s family had become spread out across the world in recent years. Right after her younger sister Stephanie moved out, her parents had filed for divorce. Her mother moved across the country to Honolulu. Jenni’s relationship with Stephanie was complicated, so she didn’t really know what she was up to nowadays.

Her mother had invited Jenni to visit her in Hawaii and meet her new boyfriend. He was apparently some local celebrity who she had met at a friend’s birthday party, and owned a big house by the beach where her mother now had moved in. Apparently, he was also the one to come pick her up from the airport.

Jenni knew she would have a hard time containing herself on the visit. The fact that she hadn’t had proper sex for more than a month, combined with the hot surfers who tended to flock the Hawaiian beaches, meant her sexual drive could easily go way out of control. She’d have to be careful.

Knowing a long day was ahead of her, Jenni set her alarm for 7 AM. She woke up, took a shower, and had breakfast. Her bags were already packed, so all that was left was to pick an outfit and do her makeup. Jenni was feeling slutty today and let her outfit reflect that. She chose a sleeveless golden top showing just enough cleavage, which she tucked into a tight black skirt with a zipper down the back that went down just below her knees.

As for her makeup, it wasn’t anything special. Just the usual foundation, highlighter and bronzer; as well as a little brown eyeshadow, eyeliner and mascara. Some pink lip gloss finished the look off.

Jenni was ready to leave. She put on a pair of red heels, grabbed her suitcase, and grabbed a taxi to the airport.

*******************************

Almost 16 hours later, the plane landed at Honolulu International Airport. Jenni picked up her luggage and went to look for her ride. Her mom had texted her a vague description of what her boyfriend looked like – caucasian, tall, handsome, shaved head and muscles big enough to carry the fattest person in all of Hawaii. With nothing more than his name, Derek, and a description that might as well have been written a 13-year old talking about her favorite actor, Jenni thought this would be a challenge.

To her surprise, it wasn’t at all. Waiting in Arrivals was a man who perfectly fit her mom’s description. A middle-aged düzce escort man with a shaved head who towered everyone who dared stand next to him. He was wide as well – not from fat, but from muscles. His shaved head made him look somewhat like a bodybuilder. Jenni felt her pussy get wet at the sight, and she decided to ask if he really was her ride.

“Hi,” she asked in her most sultry voice. “Are you Derek?”

“That would be me,” he responded with a smile, and shook her hand. “I take it you’re Jennifer, Martha’s daughter?”

“Please, call me Jenni.”

“Fair enough. Let’s get going.”

They walked through the airport together, doing the usual small talk. Jenni pushed her chest out a little extra to give Derek the best possible view of her cleavage. She didn’t care if he was dating her mom – his dick was going inside her pussy before she flew home.

The drive home was nice. Derek was good company, and Jenni looked forward to spending some quality time with him before her mom got home from work. Even better, she could notice him occasionally glancing down at her cleavage.

****************************

Derek’s house was just as extravagant as her mom had described it. It was two floors high, with numerous balconies and a big swimming pool out the back. On the way to what would be her bedroom for the next couple of night, Jenni counted at least three bathrooms, four bedrooms and a couple of living rooms.

“This’ll be your room,” Derek finally said as he opened a door.

The room had a perfect view over both the swimming pool and the nearby beach. A queen size bed was standing against one wall, and next to it was a black dresser. The bed was neatly made with patterned sheets. Jenni decided this was the time to take things up a notch.

“God,” she complained loudly after taking in the view for a moment. “My back is so sore after the flight.”

“Really?” Derked asked. “Which airline did you fly? I’ve never heard anyone complain before.”

“American. I’ve never complained before, either. Strange, right?”

Derek nodded in response.

“You know any good massage places nearby?” Jenni asked.

“Can’t say that I do. I’ve got a massage license back home in New York State, though.”

“Mind giving me a massage?” Jenni smirked, knowing this was her chance.

“I’m not sure how your mother would feel about that, Jenni. What if she walked in on me massaging her daughter?”

“She won’t be home from work in at least two hours. We’ve got time.”

“What if she decides to come home early?”

“My mom’s not one for surprises, Derek. Please?”

Jenni asked in her sweetest voice, and hoped things would go as she wanted them to.

“Alright,” he sighed after a moment’s thought. “Where do you need massaging?”

Jenni laid on her stomach in the bed, and placed her hands on her lower back.

“Right here,” she said. “Maybe even lower than that.”

“I’ll see what I can do.”

Derek sat down on the bed next to Jenni, and began rubbing her back. He started soft but slowly started putting more and more pressure on her muscles.

“Better?” he asked after a minute’s massaging.

“Nah,” Jenni said and shook her head. “It’s lower than where you were.”

Jenni turned her head to the side and could see the puzzled look on Derek’s face.

“Your skirt’s kinda in the way of anything lower than this,” edirne escort he eventually said.

This was her chance.

“I’ll fix that,” Jenni said and reached behind her back.

She fumbled around until she felt the zipper. She pulled it down a little bit, revealing the back thong she wore underneath. Derek swallowed somewhat uncomfortably.

“Much better,” she laughed.

He resumed massaging on the spots previously covered by her skirt.

“Better?” he eventually asked again.

“Nope. Lower still.”

“I really shouldn’t go any further than this,” Derek complained.

Jenni knew he would essentially be squeezing her ass if she unzipped her skirt any more. But that was just what she wanted.

“I won’t mind,” she said and pulled the zipper down even further.

Her ass was almost completely exposed. The skirt wasn’t covering anything more than her thighs by this point. After a little hesitation, Derek placed his hands on her ass and got back to massaging. Jenni could almost sense that he knew where she was taking this.

“You’re getting closer,” Jenni purred after a minute of massaging. “Here, I’ll show you.”

She once again reached behind her back. This time, she grabbed his hand and guided it between her ass cheeks. She helped him to start rubbing, until he was rubbing her ass crack on his own.

“That’s it,” Jenni moaned. “That’s the spot.”

Suddenly, Derek stopped. He got off the bed and leaned against the dresser.

“I can’t do this. I’m dating your mom, for God’s sake!”

Jenni stood on her knees in the bed, and pulled her skirt all the way off.

“C’mon, Derek. You know you want to.”

She pulled her top over her head, leaving her in only underwear and heels. She walked over to Derek and put a finger on his chest.

“I won’t tell her,” she whispered in his ear.

Jenni leaned back to look him in the eyes, and could see how she was struggling to resist her seduction. Eventually, he gave in.

“Fuck it,” he mumbled and started kissing Jenni.

She couldn’t help but laugh before returning his kisses. They held each other tight as they made out. Derek eventually began fumbling around behind her back, until he found her bra and unhooked it. Jenni took a step back and let it fall to the floor.

“My God,” Derek mumbled.

Jenni let out a small laugh as he began kissing them. She placed a hand on the back of his head, pushing him even closer. Derek sucked and slobbered all across them, occasionally biting her nipples lightly and pulling them. It hurt just to the point where it increased the pleasure.

As he was worshipping her tits, Jenni pulled her panties off and tossed them across the room. She pushed Derek’s head up and kneeled down in front of him.

“Let’s see what you’ve got for me,” she said as he pulled his white t-shirt over his head.

Jenni unbuckled his belt and pulled his pants to the floor. Derek kicked them off his legs and pulled his boxers down, revealing his rock-hard eight-inch cock.

“Looks like you’ve been thinking about this as much as I,” Jenni laughed.

Wasting no time, she immediately started licking it. Treating it like an ice cream, she gave it long licks going all the way from his ballsack up to the tip, before starting over again. Derek seemed to enjoy it.

After a minute’s licking, Jenni decided to put it in her mouth. She started elazığ escort with just the tip and gathered all the precum she could with her tongue. She swallowed it before giving his dick a kiss.

This time, she put her entire mouth around his cock and let Derek take control. He began thrusting in and out of her mouth, essentially facefucking her. Jenni fondled her nipples with her hands and let Derek do the work. As he thrusted, Jenni just flicked her tongue across the bottom of his dick.

Jenni was getting horny. She moved her head back, forcing Derek to stop thrusting. She gave his dick a kiss before standing up. Derek kissed her on the mouth before lifting her up, and walking over to the bed. He laid Jenni on her back with her pussy facing him, and placed his dick right by her entrance.

“Fuck m-,” Jenni begged.

Derek didn’t even let her finish her sentence before sliding his cock inside her pussy. He didn’t go far at first, but his dick was thick enough for it to stretch her hole considerably. Jenni screamed in surprise as he entered again, this time going even deeper. Derek kept fucking her like this for a good minute before settling into a steady rhythm.

Jenni arched her back as she laid on the bed, allowing Derek’s dick to go even deeper inside her. Her tits were on show as well, showing the roundness of her implants as her body was rocked back and forward by Derek’s thrust.

“Fuck, you’re hot,” Derek moaned.

“Hotter than mom?” Jenni laughed.

For some reason, it turned her on to compare herself to her mother in bed. She’d never tried it before!

Derek just laughed in response. He then placed under her back, and pulled her up towards him. He got on his back, held Jenni’s body in place with his strong arms, and resumed fucking her. Jenni was impressed by the smooth position change, and leaned down to give him a kiss.

“I bet you my pussy is tighter than hers,” she whispered into his ear.

Once again, Derek didn’t respond in words. He instead increased the pace of his thrusts to the point where Jenni’s screams of pleasure must have echoed across the entire island. What if her mother was to come home early? The thought just turned her on even more.

Jenni straightened her back as Derek slowed down. He reached up to grab her tits as Jenni began riding him. She lifted her ass up and down his shaft, while keeping her boobs in place for Derek to squeeze.

“I’m gonna cum, baby,” he panted after a while.

“Spray your cum all over my face, Derek,” Jenni said and rolled off him.

She laid on her back and let Derek move to the side of her face. He grabbed his dick, aimed it at her mouth and closed his eyes. The moment Jenni stuck her tongue out, he began shooting. His load was mediocre, with just a few shots of jizz in total. The cum that didn’t land on her tongue formed a sexy ring around her mouth.

When his shooting began to turn into dribbles, Jenni reached up to give his dick a kiss. She licked it clean before laying down again.

“Holy shit,” she said while catching her breath. “That was awesome, baby.”

“You can never tell Martha about this,” he grunted while slapping his cock across her tits to shake off the excess drops of jizz.

“I won’t,” Jenni laughed. “So what’s the verdict?”

“Huh?”

“Who’s best in bed, me or mom?”

“You. Without a doubt.”

“Thanks,” Jenni said, and began scooping up the cum splattered across her face with her fingers. “You have a shower I can borrow?”

“Sure do. Second door to the right of your’s.”

“Perfect. I think I’ll relax here for a minute first, though.”

“As you wish.”

Derek got off the bed and left the room without saying another word.

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