Lucky Babysitter

Jenna glanced at her watch. It was almost 11:30pm and Troy still hadn't come home yet. It was Saturday night and Jenna had been hoping to be done babysitting her neighbour's three year old son by now. She impatiently paced around the living room, texting her friends and letting them know she would be late. She walked outside onto the front porch, into the cool Miami air with the August breeze blowing through her hair. Jenna was a college junior about to enter her senior year and during the summer breaks, she lived with her parents at home to save money and spend time with them since she went to school on the west coast.

Troy had moved into the house next door a few years ago with his now ex-wife and son. He was only 31 but seemed to be getting along okay. The divorce was drawn out and long but in the end, he won custody and got to keep the house. Troy was always nice to Jenna as she grew up from a teenager into a young woman and she always had a slight crush on him. He stood six feet tall, worked out almost every day, and was unbelievable charming. He was a devoted husband and father but got married too young to his high school sweetheart. Now that a year had passed since his divorce was finalized, he decided to finally get back out there and start dating again.

Troy had met a woman at the coffee shop in the lobby of his office building and they were out on a date tonight. Jenna had seen Troy off and spent the evening watching his son, Tyler, and watching television. Two unanswered texts and one unanswered call later, Jenna started to get worried. She was sitting on the couch contemplating whether or not she should call Troy again when she heard him pull up in the driveway and hurry up the front steps into the house.

"I'm SO sorry! You will NOT believe what happened," Troy walked in directly to the fridge and grabbed a beer. Twisting it open, he dropped his jacket on the couch and sat down beside Jenna.

"Troy, you're over an hour late and you weren't picking up! What the fuck?"

"Jenna. My date. Holy shit. We were at dinner and having a nice time.. she's talking about work and her friends and travel.."

"Get to the point." Jenna was trying to hurry this story along. She wanted to head out immediately and meet up with her friends before last call at the bar. It was one of the last nights all of her high school group of friends would be together before everyone started heading back to school all over the country.

"Okay, okay. Yeah. So her ex shows up and then I realize that hey, she's not single, he's not her ex, he's her FIANCE. So he tried to kick my ass, we were removed from the restaurant, he drove off and she followed me. Tried to persuade me that it wasn't what it looked like... all of the classic lines."

Jenna started laughing. "That's hilarious. Shit. Did you get hurt?"

Troy polished off his beer and got another one from the fridge. He leaned against the door as he took a sip. "No, but he got a pretty good punch into my ribs. Just a bit sore though."

"Ok well I'm glad you're okay but I need to go. My friends are waiting for me so that'll be $50 for tonight. BUT you owe me though, for staying so late." Jenna picked up her cell phone and walked towards the door where Troy was standing. He pulled out his wallet and handed her a $50 and waited to see her reaction. Jenna looked at him and teasingly coughed as if to shake him down for some extra cash.

Troy set his beer down on the table and took a step closer to Jenna. He leaned his face closer to hers and put his lips up to her ear and whispered, "You didn't say how you want me to owe you."

Jenna was caught off guard. Was Troy coming onto her? He only had one beer so she couldn't pretend to blame it on alcohol. Suddenly she didn't care about her waiting friends because she was distracted by the sudden twitch of her pussy and became aware that she was feeling a little damp.

"What did you have in mind?" Jenna couldn't believe that she uttered those words in response. She felt Troy's hands cup her firm round ass through her sweatpants as he pulled her closer to him, pushing her pelvis against his. Troy hadn't moved his head from beside Jenna's as they started to slowly grind against the other. Jenna could feel a bulge in his jeans forming as Troy continued to squeeze her ass in his hands. They began to breathe heavier and the sound of each other panting in the other's ear turned them both on even more.

Troy pulled back so that he was looking into the eyes of his sexy 22 year old next door neighbour. After he had gotten divorced, Troy didn't have a shortage of dates but he was preoccupied with work and spent a lot of time playing sports. He had been hoping to break a six month dry spell tonight when he went out but clearly it didn't pan out. Troy felt a pang of guilt that he was corrupting Jenna but she seemed to be game for it. Because he had seen no action in the last six months, he had a massive amount of sexual tension built up in his body that no amount of basketball or hockey or volleyball would help relieve. Over the years, he had watched Jenna grow up and he couldn't deny that there were more than a few masturbation sessions where he had fantasized about her perfect ass that defied gravity, wondering what it'd be like to stick his thick rod into her tight pussy.

Tonight, Troy decided he was just going to go for it. He had spent too long being a good guy and he couldn't deny temptation any longer. He leaned in without saying anything and kissed Jenna's soft lips. Jenna wrapped her arms around his neck as she started to kiss him back and pushed her tongue into his mouth, flicking his tongue and massaging it with hers. Troy continued to grind his crotch against hers when suddenly he pulled away and looked at her, both of them panting slightly. She stared into his crystal blue eyes and he stared into her warm green eyes.

"Bedroom." Troy whispered. It wasn't a question but Jenna had no intention of saying no. Her pussy had completely soaked her thong and she was afraid that she was going to soak through her sweatpants. Even in her sweats, Troy found her sexy as ever and loved that he was about to hook up with the girl next door.

Jenna followed Troy to his bedroom where they resumed kissing as they fell onto his bed. Troy finally pulled his hands away from Jenna's ass and moved them onto her tits, groping and massaging as she moaned into his mouth. It didn't take long before he reached under her shirt and took it off, quickly followed by her bra. He started to play with her hard dark brown nipples and tugged on them without breaking their kiss. Wanting to return the favour, Jenna ran her hands down Troy's chest and stomach until she reached his crotch. She rubbed her hand along the large bulge that had formed and it was Troy's turn to moan into her mouth. Jenna started to undo the button to Troy's jeans but he pushed her hands away making her whimper in protest.

He replaced his fingers with his mouth on her right nipple and slid his hands down right past the waistband of her sweatpants. Heat radiated from her crotch as Troy's fingers made contact with her wet thong and Jenna gasped. He stopped sucking on her nipple and brought his lips back to hers. They resumed their embrace as Troy's fingers explored Jenna's wet area but he was careful to avoid her clit or part her lips to reveal her hole. His fingertips were soaked in her juices and after a few minutes of teasing and Jenna attempting to grind herself against his hand, he gently spread her lips apart and ran his finger up the length of her slit. Wetness was leaking out of Jenna and Troy used some of it to lubricate her clit. He gently began to move his fingers in circles around her sensitive nub as Jenna began to moan. Right before Jenna's body was about to climax, he stopped and in one swift movement, pulled her sweatpants and thong off. Troy pushed her legs apart and Jenna held her ankles up in the air, exposing her perfectly pink hole and showing Troy how turned on she was.

Troy leaned over and put his face up to examine her glistening pussy. Her hole was still leaking and Troy stuck his tongue out and gently licked up some of the wetness. He trailed his tongue up to her clit and began to gently suck on it, causing Jenna to moan louder. He continued to suck and began to flick her clit with his tongue. Troy brought his right hand up to his face and started to play with her hole with his index and middle finger. He was working magic on her sensitive spot and sent Jenna to the next level of pleasure when he started to pump his fingers in and out of her hole. The wet sound of his fingers penetrating her warm box turned him on and he felt his cock strain against his jeans, begging to be let out, but not before he brought Jenna to orgasm first.

"Shit, I'm going to cum! Troy! Fuck!" Jenna started bucking her hips and grinding her pussy against his face. She hit her orgasm and covered Troy's mouth and chin with her sweet nectar that was pouring out of her. Troy lapped up as much as he could into her mouth, swallowing all of her hot juices. He sat up with a grin on his cum covered face. He pulled his shirt over his head and started to undo his pants. He stripped down and when he pulled off his underwear, he revealed his raging nine inch hard on. Pre-cum was covering his shiny mushroom tip and Troy used his thumb to move it around his cock head.

Jenna still had her legs spread apart and she felt her pussy twitch a few times as she stared at Troy's manhood. His cock was sticking straight up and his big balls were twitching in anticipation. She reached down and started to finger herself. Following her cue, Troy started to jerk himself off using his pre-cum as lube. The wet smacking sounds of both of them masturbating filled the room and soon, Jenna was ramming her fingers into her pussy and rubbing her clit furiously while Troy pumped his meat stick with both hands pushing more pre-cum out with each stroke. Jenna's second orgasm hit her and her body went stiff for a second before going limp. More nectar dripped out of her hole as her pussy walls convulsed, taking her to another orgasm.

Troy was so turned on that he felt his balls were going to explode at any second. He watched Jenna cum and as she was coming down, he moved closer and helped her rub out another orgasm with the tip of his dick on her clit. The mixture of his pre-cum and her juices made her whole slit slippery and Troy started to rub the length of his shaft along her soaked crotch.

"Will you fuck me already?" Jenna panted as she spread her legs even more. Troy winked at her and reached down and started to expertly finger her pussy, using his fingers to go in and out of her tight and wet hole. He could feel her pussy walls spasming again and as she was about to hit climax, he withdrew his fingers and slammed his whole shaft into her pussy and began to immediately drill his thick cock in and out of her. Jenna screamed out Troy's name as he humped her, his balls slapping her ass as he continued to plow her.

"Harder... fuck me harder..." Jenna begged and moaned. Troy flipped her over with his dick still inside of her and started to fuck her from behind. He grabbed her hair and pulled on it as he continued to piston in and out of Jenna's sopping wetness.

"I haven't had sex in six months," Troy grunted, "I'm going to cum soon."

Jenna moaned as Troy fucked her with his engorged man meat. His balls were tightening with each thrust and he knew he couldn't last much longer. Jenna pushed him onto his back without breaking their rhythm and started to bounce up and down his hard tool. Her slit was oozing with wetness mixing with his pre-cum inside of her hot love tunnel.

"I'm going to shoot! FUCK!" Troy's balls seized up and he started to cum inside of Jenna. She pulled his cock out and jerked him off, her hand moving in a blur, as she coaxed more creamy white cum ropes out of him. Troy was grunting and moaning with his eyes closed but Jenna didn't want to stop as she stuffed his jizz covered cock back into her and used her pussy walls to continue to massage his throbbing member. She started riding his dick again which was still hard as a steel rod. Troy knew his second orgasm wasn't far behind as he fucked his last load out of Jenna.

Troy shifted so that they were both leaning back and thrusting their crotches together. He watched his penis disappear in and out of Jenna and spunk drip out of her.

"Come on Troy. Fuck my cunt. You know you love it. Give it to me!" Jenna encouraged Troy as he picked up pace and started to move his hips faster and faster, pounding his twitching cock into Jenna's fuck hole towards another orgasm.

"Shit! I'm going to blow!" Somehow, Troy managed to fuck Jenna even faster and his balls slapped her ass loudly as he approached his final act of the night. His large balls tightened and Troy unloaded eight streams of thick, creamy white cum into Jenna, coating her spasming pussy walls. He slowly withdrew his cock and a large amount of cum dripped out of Jenna's drenched pussy. The two of them lay on the bed panting for a few minutes before Jenna got up and went to the bathroom to clean herself up. When she came out, Troy had put on shorts and he walked her to the front door.

"Thanks for babysitting. And sorry again for being late." Troy grinned at Jenna.

"You can be late anytime so long as you know you owe me." With that, Jenna winked and left Troy's house. She couldn't wait for the next time he needed a babysitter.