Bad Little Boy Ch. 01

Tonight was a night like any other, and yet, unlike any other night, there was an electricity that hung in the air. Sometimes, the most opportune exchanges can be made at exactly the right moment, and there was no moment better than now.

Toby's heart was racing, and the blood was pounding in his ears. Tonight, of all nights, he was going to finally meet someone. He appraised himself in the mirror, going over every minor detail.

He was a perfectly average boy of 19; a decent build, an ordinary height. His light brown hair was cropped short and formed a fauxhawk tip at the point of his head, with light sideburns and a goatee accompanying it. He tried to force a smile, and bring out an endearing look. He wasn't an unhandsome youth, but his confidence had always been somewhat lacking when it came to girls.

It had been months since he had been in bed with anybody. Not that his sexual encounters were unsatisfying; he liked to think that he knew something about girls that other guys simply couldn't understand. No, Toby always had a problem with confidence. He had been the loaner throughout High School, and was still trying to break out of his shell before he graduated in his Senior class.

He checked his phone, waiting for a sign. It had been only three hours since he had made a message to a want ad for a casual partner on Craigslist, and he was eager to hear back from her.

"Lonely Housewife -- 33", the heading had stated. The opportunity to get with an older woman was something considered fairly legendary among Toby's circle of friends; it was an impossibly high standard to reach for many guys his age. Only his friend Joe had ever succeeded in bedding an older woman, and he rarely shared any of his wisdom.

There was something about the girls his age he had found to be simply unappealing. They never acted very mature around Toby. That is, whenever he mustered up the strength to talk to them. He frowned. So much for ever being a ladies' man.

In the throes of his hormone-addled youth, Toby was seeking out a complete stranger. His mind raced to think of the possibilities of the night ahead.

A green light blinked on his phone, and he quickly flipped open his email application.

"Error in State.AccessHandlerException(33)" the message title read. He sighed, slightly crestfallen. Of all the evenings he had wanted to hear from this mystery woman, he instead was getting error messages from a developer mailing list. He hated that his hobbies could somehow get in the way of pursuing what he really wanted. Rather, what he really needed.

Throwing on his jacket, he stormed out to the deck for a smoke. The cool air blew past him on this solitary November eve, as he looked over the fence at the suburbs around him. He silently prayed that he would have somebody to hold onto tonight. He needed this.

The light on his phone went off again, contrasting against the red glow of his cigarette. He flipped it open again.

"Re: Fun For This Evening" it read. He opened it, and read over it several times.

"Hi,

My husband leaves in the next half hour. I see that you're just across town from me. He'll be gone tonight until midnight. Come soon, and show yourself in.

-Alice <3"

Attached was an address. He grinned. That was only three streets over! Whoever this woman was, she was as good as his. Now he only had to count down the minutes.

He checked his watch. 8:25. He began to grow nervous. What if she didn't like him? What if her husband caught him in the act? What if she was unattractive? She had only sent a description, and he had never thought to ask for a picture.

Toby opened his Camel Crush cigarettes, and continued to smoke stick after stick. The minutes were passing by at a snail's pace, and he was only getting more eager to meet this woman. Thoughts of the nasty things he could do to Alice flashed before his eyes. He hadn't gotten any since April, he needed this.

It felt like an eternity had passed before 9 had rolled around. Finally, he threw down his last cigarette, and ventured into the suburbs.

Dimly-lit lamps illuminated the cracked pavement underneath his feet, as the breeze blew against his chest. No matter. Tonight was going to be a night to remember. His heart continued to race in his chest. Every step felt like it simply took too long. Toby found himself sprinting across the sidewalks and streets, making his way to this trophy-wife's abode.

He finally came to what could only be the correct doorstep. 1303 White Stallion Drive. It was a well-to-do sort of house, and yet, it had an oddly familiar look to it. He just couldn't quite put his finger on it. Looking over into the driveway, he noticed a distinctive lack of any sort of car, so he showed himself in.

The first thing he noticed as he walked through the front door was a sign pointing up the stairs. Obviously she was waiting for him. As he began his descent up the stairwell, he noticed that every portrait had been turned around to face the wall. This struck him as unusual, but he thought little of it. Perhaps she just didn't want him getting too involved in her personal life.

A second sign on a door at the top of the stairs simply said "Knock". He sucked in his breath, took a moment, and knocked on the door gently.

"Come in!" a woman's voice rang out sweetly.

He opened the door quietly, and walked in with a start. She was laying on the bed, completely naked, with her face against the pillow. Her arms and legs were fastened to the frame of the bed, and her back was arched, ready for action. It was odd, not seeing her face, but Toby was oddly aroused.

She was in decent shape. She was just slightly chubby, and her curves wrapped around her body beautifully. For someone her age, someone like her was an obvious choice.

"Hi..."he began, "I'm Toby..."

She motioned her slender fingers in a circular motion, indicating to him that she wanted him to undress. Toby quickly stripped off his hoodie and jeans, and prepared himself mentally. This was actually happening, and he needed to get into the right mindset. It's not everyday a young man gets to enjoy an older woman like this.

An idea crept up in the back of his mind, and he sat on the floor behind the bed. He tilted himself up slowly, until her slit was level with his face. She was moist with anticipation. Her aroma wafted down to him, and he breathed it in deeply.

He could feel the gap in her legs start to close around him, daring him to make a move. He ran his tongue around the edges of her pussy, and tasted her for the first time. He could feel her letting out a breath, so be began to make motions with his tongue against her clit. The flat of his tongue was against her, licking over and over again. He hummed against her opening and kissed it, and he noticed her toes beginning to curl.

She was delicious. He continued to lap her up as she let out moan after moan.

"Aagh, Toby...a little higher...use the...OH! THERE! JUST LIKE THAT! OHHHH."

Some of her juices squired into his mouth and onto his face, and he lapped it up like a champ. He continued kissing his way up her abdomen and belly, and made his way to her breasts.

He grabbed both in his hands and squeezed her nipples gently. She let out a soft moan of pleasure, and so her greedily sucked one while he played with the other. Using his free hand, he fingered her, and she let out gasps of euphoria. He felt like a switchboard operator, moving from one tit to the other while he was knuckle-deep inside of her.

Toby caressed her back and began to kiss and suck on her neck. As his face grew closer to his, she used one of her bound hands to cover his eyes. His mind swam in darkness for a moment, as he felt her mouth against his. Their tongues joined one another, and danced in harmony.

"Fuck me, Toby." she said in his ear. "Make me your girl tonight."

Still blind, he could feel the space in her legs open slightly and make their way around the area of his crotch. This was it, and he was absolutely ready. He felt himself penetrate deep into her all the way down. Her vessel stretched tightly over his cock, and he could feel her pushing against him to get him even deeper inside.

They began to pick up the pace, and he could hear her breathing grow louder and faster. She was kissing his cheek, and his neck, and her breasts were pressing against him.

"Oh, Toby! Oh! OH, FUCK ME!" she cried. He kept penetrating deeper and deeper into her, faster and harder. She was on the verge of a climax, and so was he. He felt himself in the moment, riding a complete stranger bound to a bed. He had never felt so alive before.

He couldn't hold it any longer. Toby felt himself shooting load after load inside this woman. They were in complete euphoria together, basking in the afterglow of an incredible encounter. Suddenly, her hand slipped off of his face, and he gasped.

Alice. Alice Harker. Mrs. Harker. Toby had just fucked his English teacher.

TO BE CONTINUED...