Neighbor Affair (closed)

[Intensityrising]

https://lh3.googleusercontent.com/-bkJhUwds1Lk/Tvx7s_C_VTI/AAAAAAABc6o/-JSLuxIDIIQ/w800-h800/Curls.jpg

Jennifer Matthews was twenty seven years old, marries to a man nearly double her age and she was living the life she almost always wanted. Almost. Okay, her husband Grant was a fantastic man, kind, caring, rich, handsome, rich, and she loved him. He wasn't really that rich, they were comfortably middle class, that was all really. But Grant made enough money that Jennifer didn't have to work on anything but her body. Which made Grant happy.

Jennifer stayed in shape, did whatever she could to make sure she stayed sexy for Grant. Until the day she found herself making herself sexy for someone else. She wasn't quite sure how her affair with the neighbor got to such an uncontrollable level, but now that it was going full bore she was not about to stop it, despite how much shit could hit the fan should Grant find out.

This is the story of how it started.....

Jennifer met the neighbor boy one day when he came around trying to sell his services of lawn mowing to everyone on the block. Apparently he was trying to work for his own money to buy a new Xbox or something. He was a nice enough looking guy, very shy though, he seemed to be scared to look at her, despite clearly wanting too. It amused her, and she offered him ten bucks to mow the lawn and then further money to do a few extra things around her house.

This became a weekly thing, Saturday's when Grant was doing his business meetings on the golf course, Jennifer would pay the neighbor boy to come over and take care of some chores. As time went on they began to talk and get to know each other a little. Jennifer did what she could for his nerves around girls, unbeknownst to him. He was so shy and almost embarassed to look in her general direction when he first started coming by that she made it her mission to make him more at ease when talking to her. A few times she made him lunch and they sat together out on the padio to eat and talk about random things.

He told her about video games, and she mostly listened. He was a nice guy, and not bad looking although he could use a few style tips. Jennifer was convinced that with little help he could end his senior year of his school very popular with the girls if he should want them.

 

[StFornicate]

Tommy O'Brien couldn't believe he was really going to do this. Really, who does this kind of thing? A guy like him had absolutely zero chance with any ladies, much less the older, married woman next door. Who did he think he was, anyway? Some Rico Suave smooth motherfucker with huge brass balls? Nope. He was just the nerdy boy next door who did random chores around her house while her husband was away.

Tommy shook his head, and paced his room, before looking out the window again. Yep, her husband was working late again; the Cadillac SUV was gone, and just her fancy Camaro sat in the driveway. He took a deep breath, knowing how foolish this was. Did he really even want to go to prom? He'd never been to any other school dance in his four years of high school. But for some reason, this seemed important. And, well, he had no one else to ask. Besides, what was the worst that could happen? She'd turn him down?

Yeah, that would suck quite a bit, but... it wasn't like she wouldn't be without reason. She was twenty-seven, after all. Why would she want to go to some stupid high school prom, and with him of all people? He knew he wasn't much to look at. Tall, with a mop of curly brown hair, and skinny, in spite of how hard he might work out in her yard.

Still, she was his only last hope of having a date for prom. So he steeled himself, and went downstairs and out the front door, and marched over to her door, and knocked on it...

 

[Intensityrising]

Jennifer was enjoying a bit of Scotch, her husband was working late tonight as he did most nights which left her alone and free to do whatever she wanted to on whatever whim she felt. Lately she rather liked having a bit of Scotch and then taking a long hot bubble bath. She finished her glass of Glenfiditch and was about to head up to the bathroom when there was a knock on the door.

Confused she opened the door, wearing her tight tank top, and house shorty shorts. Tommy stood there looking like a tomato, red and chewing his lower lip like he was about to tell her the world had ended and he was the last man on Earth. Okay maybe not quite that serious, but still to an eighteen year old it might as well be, once she knew what the question was.

"Hey...Tommy...Wh...What are you doing here at this hour?" She asked, leaning against the frame of the door and trying to hide the alcohol on her breath.

 

[StFornicate]

"Hi, Miss Matth..."

Shit. Already fucked it up. "I mean, Jennifer..." he corrected himself. She had made a point of insisting he call her by her first name, but it was a hard habit to break. "Uhmm, yeah, hi..." He couldn't help but get a glance of his neighbor's amazing body, in that tight tank top and tiny shorts; her cleavage was the type a guy could get lost in for days.

He blinked. "Okay, sorry, uhm, listen, I have this thing coming up, it's a dance, uhm, it's the prom and I don't have a date and you can't go without a date cuz of some stupid school policy so I was wondering if you weren't busy next Friday night if you would go with me?"'

He could feel himself blushing harder and harder as he spoke, his words running together until finally he got it out and he stopped and looked at her and said a little silent prayer to whatever sex god might be out there.

 

[Intensityrising]

Jennifer tried very hard to hold back her laughter. Not because his request was funny, but because of how adorable he was when he asked her. Speaking of asking her, did he just ask her to the prom? A high school prom? Good lord she would be so out of place with a bunch of high schoolers now. How long had it been since her prom....eight years? Nine?

Jennifer knew that she should say no, but if she did Tommy wouldn't get to experience prom at all. Poor little awkward kid wouldn't get anyone to go with him and if by some miracle one did, it would be a set-up to some evil Stephen King joke. So he was right about one thing, she was the only one he could dare even ask to go.

Still she should say no, it was almost as mean of her to go with him than not to go. If she went, Tommy would get his hopes up for a real prom experience, a kiss, a hummer, maybe even a cherry pop. But she couldn't do any of those things and her going to his prom would be the worst cock tease in history.

She opened her mouth to explain to Tommy why she couldn't go with him. To tell him that it was better to have no prom, than go with someone that would make the prom fake and boring.

That was what she was going to say. Honest.

What actually came out of her mouth. "Sure Tommy, what time do you want to pick me up?" The shock on her face, melted quickly into a smile.

Dear god what had she just done?

 

[StFornicate]

She said yes.

Wait, what? Really? Tommy's mind reeled from Jennifer's affirmative response. He had assumed she would decline, in the sweetest way possible, of course.

But she had said yes. Still flabbergasted from her affirmative response, he wasn't sure what to say. He had rehearsed over and over again what he would say when she turned him down! But she was actually going with him! It was too good to be true!

"Uhm, yeah, uhh, is six good? I think we're supposed to have dinner first or something..." he said. He'd never been to any of the other high school dances, and he had no idea what the protocol was.

But none of that mattered, really. He was elated, and a big smile spread across his face. He'd been utterly smitten with this woman ever since she and her older husband had moved in next door to him a few years ago. She was the subject of his every fantasy, even though he knew that none of them would ever come true. The fact that they had kind of, sort of become friends recently was the closest he would ever get to her. She was married, after all.

And she would never be interested in cheating on her husband with a kid like him!

"Hey, you wouldn't happen to have any extra jobs around the house for me to do this week, would ya?" he asked, realizing he was going to need the extra money!

 

[Intensityrising]

The shock on Tommy's face was amazing. Jennifer had to hold in laughter for fear that he would think she was just fucking with him. Tommy was a good kid, kind heart, just a little on the shy side. Perhaps he was a bit of a geeky kid too which didnt help his high school popularity but she figured that going with him would be a nice way to give him a treat.

Besides she was already thinking of the dress she would wear for him. She hadn't seen the girls in his school but she had seen herself in the mirror when she was all dolled up and she would make sure that Tommy would have the hottest date in that dance. Oh that looks he was going to get, hell no one was going to believe she was really there. It was going to be epic.

As tommy recovered from the shock of her agreement he stuttered out a time and mentioned dinner which made Jennifer smirk. "Actually you eat after prom Tommy. That way the spiked punch doesn't make you sick in the heat of dancing. That's a pro tip." She told him with a wink. "Prom starts at what eightish? Pick me up at seven and we will show up fashionably late."

She smiled at him. "You know pro tips from a Master and all that."

"As for housework I dont really have anything special this week buddy, sorry. Although I did talk to Mrs. Carl across the street and apparently her housekeeper quit. So she might be able to give you some extra work." She smiled.

"Ill see you soon Tommy. I gotta run." Pee actually, stupid alcohol. She thought.

 

[StFornicate]

Tommy was a bit bummed that she didn't have anything for him to do, but he was so elated, and nervous, suddenly, about prom that it didn't really matter. She headed off and he headed over to Mrs Carl's to see what she had for him to do, and it turned out to be plenty of yardwork, which paid well.

He spent the next week doing as many odd jobs around the neighborhood as he could, saving up for the big night which was rapidly approaching. He even sold off some of the more expensive cards from his massive Magic: the Gathering collection for extra cash. That was hard, he had to admit, but every time he saw Jennifer in passing, he knew it was worth it.

Even better was now they had a little secret together. The little smiles she gave him were knowing, and shared. He knew he shouldn't get his hopes up that anything remotely sexual might happen between them, but a teenage guy's fantasies were vivid...

Of course it didn't help that he knew exactly what Jennifer looked like naked. It wasn't long after she and her husband had moved in that he had noticed one night that he could see clear across their yards, from his bedroom into hers. She almost always had the windows open, and seemed to have no qualms about undressing there... Certainly she didn't realize anyone could see inside. But he could. And did.

As often as he could. It was almost a nightly ritual for him, to watch as she sipped her wine and stripped down for her evening shower. It was just as much fun to watch her slip into her sexy little nighties, adjusting her glorious tits in them for maximum cleavage.

He wondered if she knew he was watching... Even as he jerked off with those images burned in his mind...

The big night arrived. He had his tuxedo, black with pinstripes, bowtie, the whole nine yards. And a limo. He got in the limo and instructed the driver to park in front of the house next door, got out, corsage in hand, and went up and knocked on Jennifer's front door...

 

[Intensityrising]

For the big day Jennifer had gone out and got herself a sexy yet modest bright red dress. She had taken the liberty of slipping into Tommy's school and found out what the color theme for the prom was. A traditional red and black which she rather liked because she looked absolutely stunning in red. This dress clung to her body like she was poured into it, yet left only the barest hint of her cleavage exposed, and the very bottom of her thighs. Teases of flesh, rather than leaving everything out to see, which made it perfect for a high school prom.

Tommy would love it she was certain. Then she found herself wondering why she cared how much Tommy liked her dress. Why did she care what he thought of her? Then she decided that if she was going to do this for him, she was damn well going to go all out.

She spent the entire afternoon doing her make-up and hair, changing her entire style no less than three times. At six fifty she stood before her mirror in her red dress, her hair fell in curvy waves around her face and shoulders, her lips a bright eager red, everything about it was just perfect.

The doorbell rang and she smiled, it was time for the big show. She couldn't wait to see the look on Tommy's face.

She opened the door and saw Tommy standing there with a beautiful corsage and a nicely styled little tuxedo, and top it all off with a limo that the kid had rented. She couldn't hide the grin from her lips. Then she saw the look on Tommy's face and she felt glowing.

"Hi Tommy." She said with a smile. "Do you think I'll look good at the dance?"

 

[StFornicate]

Tommy felt like his jaw had dropped clear down to the floor, and his eyes had probably bugged right out of his head, when he saw Jennifer open that door.

She was stunning. Elegant. Gorgeous. A cacophany of adjectives cascaded through his mind as he tried to find a proper response. That dress clung to her curves like it was painted on, accentuating her form and showing off how amazingly well she kept her body. And it wasn't slutty in the slightest.

"Wow... Jenn... You look really hot," he said, and promptly blushed hard. What a dolt!

"I, uh, I got you this corsage thingy..." he said, raising up the flowery decoration. In probably the boldest move he had ever made in his life, he reached forward and took her slender hand, and carefully slipped the corsage around her wrist.

His fingertips caressed the palm of her hand as he looked at her; her heels put them at eye level with each other. "I'm really happy you're coming with me," he said, softly, shyly.

 

[Intensityrising]

His nervousness was so unbelievably cute Jennifer almost felt bad as he took her hand. His hands were shaking so much he probably thought she would snap at him. The flower went on her wrist and she smiled and cupped the side of Tommy's face. "It is beautiful Tommy. Thank you."

She gestured to the limo. "You went all out for me tonight huh?" She asked with a smile. "I suppose we better get going. I am going to make everyone so jealous of you it wont even be funny." She promised, stepping out of the house and shutting the door behind her. She took Tommy's hand and pulled him toward the car trying to help him calm his nerves.

 

[StFornicate]

Her words were enough to make him beam with pride; no one had ever in the history of ever been jealous of him! Why would they be? He was a nerd, a virgin no less, terribly shy and self-conscious and...

And he found himself being pulled along the walkway towards a limousine by the most beautiful woman he had ever known!

"Yeah, I guess I did," he said as they got to the limo, and he opened the door for her and let her slip inside, and he followed behind. "Let's go, Marty!" he called out to the limo driver, and the stretch limo slowly took off.

Her touch still burned on the side of his face. He found his heart was racing. The night was young. Still, he knew nothing would come of it, really, except a good time with a woman who would always, always be just a friend.

"Nobody's ever been jealous of me," he confided in her.

 

[Intensityrising]

Jennifer sat in the limo and smiled at Tommy as he quite literally beamed at all of this. Clearly he was incredibly excited just to be going to the dance with a dance, let alone a woman who he thought was as beautiful as she was to him. It made her feel special, a lot more special than she thought she should feel, but still it was rather nice and she really liked Tommy.

They got to the prom and most of the party-goers were already inside. She smiled nudged Tommy's side, "You ready Champ, time to face the world."

The driver opened the door and let them out, Tommy first so that he could turn and take Jennifer by the arm and lead her into the dance where the music could be felt pounding from outside the building. "At least t sounds hoping." She told him pleasantly.

Inside was a different matter all together. People mingled as the prom had not reached the stage where people were outright dancing randomly about. Most of the couples were still getting eased into the situation, and of course the wild kids were already going to town on the dance floor.

They hadn't made it two feet into the room when a big jock looking guy came rolling up. "I don't believe my fucking eyes. Lame ass Tommy rolls in with a fine ass.....holy shit Tommy how much did this bitch cost you?" The guy looked her up and down which made her angry and she sneered at him. "Damn baby how about you come hand out with a real man."

She glared at him, "Seriously fucker? We have literally been here two seconds and you think you are a tough guy because you try to punk my date the second we roll in? I don't know you but I already don't like you so how about you back the fuck off me and him before I take you outside and curb stomp your ass pussy!" She yelled at him.

The bully just blinked and stared, the response so unexpected he didn't know what to do with it.

She pulled on Tommy and said, "Let's go get a drink baby."

 

[StFornicate]

"Umm, okay, baby," Tommy replied, rather in shock at Jennifer's visceral reaction to the bully's advances. Almost naturally, his hand slipped into hers and they moved along to the table where there were a few big bowls of punch and assorted plastic cups.

Tommy's mind reeled, as he watched the bully stomp off. The bully, Lance Dryden, had been picking on Tommy for basically all his life. A linebacker for the football team, and general all-around popular d-bag, Lance had always made life miserable for Tommy.

Tommy's heart raced as they got to the punch, and he realized things would get a lot worse now. "Fuck fuck fuck," he muttered, casting nervous glances around. He could see Lance commiserating with a few other football players across the gym.

"This is gonna be bad," he said. He started to feel paranoia creep up on him. He saw a small group of girls looking at them, giggling. Popular girls.

Another pair of girls slipped past behind them and he could have sworn one of them said "that's gotta be his aunt or something! What a loser!"

He felt his chest tighten up. Dear God, not an asthma attack, not now, please...

 

[Intensityrising]

Holy shit high school kids were evil. They didnt even hide the insults or the remarks. Jennifer could literally hear all the insults and evil looks coming Tommy's way. It was completely bullshit. Is this what he had to deal with all day long? Everyday? It would be a miracle if Tommy didnt kill himself or shoot up the school or something.

Jennifer raged at the comment she heard about possibly being his aunt. Little fucking bitches. Then she glance at Tommy who looked on the verge of a panic attack and she had to think quickly. She grabbed Tommy and pulled him against her. Her lips locked against his, kissing him madly and passionately. She made a show of shoving her tongue down his throat, wanting to make sure that everyone saw her pushing inside of him. She pulled his hand up to her breast and encouraged him to squeeze and molest her in front of everyone because fuck them.

Tommy deserved better than them. He deserved something better than just this fucking dance. She grabbed Tommy and said, "fuck these people and fuck this place Tommy. Lets get out of here, I wanna take you somewhere."

She pulled him from the prom and back out to the limo where she ushered him into the back. Thedriver looked confused and Jennifer said, "Gate street hotel, fuck this dance." The driver grinned and pulled away.

 

[StFornicate]

Tommy thought he was about to hyperventilate; all eyes on them, and then suddenly, the feel of her breasts pushing into his chest, her slender form pressing against him... And then...

Heaven. Her lips on his, aggressively, hungrily, lustily, better than he had ever dreamed it could be! Her tongue invading his mouth, and he was only too happy to return the favor, even if he had no idea what he was doing. Her hand grasping his and guiding him to her chest, encouraging him to grope her with her moans in his mouth...

And grope her he did! His hand closed down on her tit, grasping her flesh over the skin-tight red dress, and he immediately felt a reaction down below, a familiar rush of blood to his loins, his cock filling and stiffening...

And then she pulled away, and was pulling him along with her, and then they were in the limo again. Tommy looked at her, shocked. So many questions ran rampant through his mind, but the only one he could spit out in that moment was the dumbest one he could possibly ask: "a hotel? Why are we going to a hotel?"

 

[Intensityrising]

Jennifer looked at Tommy when he asked his question. She turned toward him and leaned over to him. She cupped his face in her hand and smiled, "because I understand what you have suffered through. I was a bully in school myself. I picked on kids who were ugly or nerdy. To see it happening to you has made me realize how evil I was and how hurtful it is to someone who never deserved it."

She kissed him again. "So I am going to make you very happy tonight. To repay you and the universe for all the bullshit you have dealt with."

The limo pulled into the park in lot of the hotel and she ushered Tommy out of the car. She told the driver he could take off as they wouldn't need him for the rest of the night. Jennifer smiled at Tommy as he watched the car drive away. "Wait here I will be right back."

Five minutes later she returned with a room key in her hand. "Come on we are in room 104."

 

[StFornicate]

Her words struck a chord deep within him. She had been a bully! How was that even possible? She had always been so nice to him! His mind boggled as she continued, explaining that she was going to make it up to him, to make him very happy, and his imagination ran wild with just what she could mean.

She went in and got a room, and the limo drove off. He didn't even care about the money he'd spent on this night. Could this really be happening? He pinched himself, but didn't wake up from the dream.

It was real. She came back out, jingling a key in her hand, resplendent in that tight red dress, and a devilish smile across her bright red lips. Their hands found each other, naturally, and made their way down a hallway before quickly coming to their room for the night. As she unlocked the door, he put a hand on her arm.

"Jen... Are you sure you really want to do this? I mean, you're married, and I'm... I'm just the kid next door..."

 

[Intensityrising]

Jennifer slipped the key into the door and opened it. She turned to him and held up her left hand. "I dont know what you're talking about baby. All I see on this hand is a lovely corsage that my boyfriend got me for prom." She smiled and slipped into the room. "Coming?"

She knew this was dangerous and risky but it was the only thing she could think of to give Tommy. He deserved something special and this was something he wouldn't get for a while yet, unless he got very lucky in college. No he needed that courage to face girls and the only way to do that was to get some experience. Frankly it was better that she do this than some girl who might laugh if he did something weird or blew his load prematurely.

Jennifer turned toward him and smiled. "Well Tommy. We are here in a private room all along. What would you like to do?" She teased.

 

[StFornicate]

Tommy blushed when she referred to him as her "boyfriend", and followed her into the room. He jumped a bit when the door shut behind him, and looked at her.

What did he want to do? What didn't he want to do? He had envisioned a thousand different ways to fuck this woman... and didn't have the slightest clue how to articulate a single one of them.

He wanted to look up at her, at her amazing, sexy body in that little dress, but his eyes seemed glued to his shoes. Nervousness and apprehension wracked him. "I... Jen you know I've never..." he muttered, wanting desperately to be the strong, dominant man in all the sexy stories he read online, wanting to sweep her off her feet, or throw her down on the bed and pull her dress up and get her from behind, or demand she get down on her knees and suck his cock.

He took a deep breath.

"Jennifer," he said, still looking down. Look at her dammit.

He looked up at her. God she was amazing. That dress was made for her. Now say it goddammit! His heart pounded so hard in his chest he could hear it in his ears.

"I... I want you. To... Suck. My. Dick."

 

[Intensityrising]

Jennifer smirked, he was so nervous but she could tell how much he wanted her. How long had he been dreaming of a moment like this, a moment in which he would be able to do anything he wanted to her. She moved toward him like a lion stalking its prey, and right as she reached him she dropped to her knees in front of him.

Her hand came up and caressed the front of his pants, she could feel he was already hardening under there. "That what you want baby? You want me to pull your cock out and shove it into my mouth." She cooed to him. Her hands worked open his fly and jerked his pants down before he could say anything.

AS wrong as this was, she would be lying if she didn't say she was getting wet. She smiled up at him and took his boxers down, letting his cock spring free. "Look at that." She said, admiring the nice cock she had revealed before her.

She grabbed the base of his cock and slapped herself in the face with his dick. "I'm so bad, you know I shouldn't be doing this Tommy. But I can't help it. I gotta suck your dick." She stared up at his face as she opened her mouth and wrapped her lips around his fat mushroom tip. Her tongue licking and flicking across him as she simply sucked on the tip of him.

 

[StFornicate]

Tommy's cock throbbed in his pants as he watched Jennifer approach him, and drop to her knees. She unzipped his pants and grasped at his turgid member, pulling his cock out and smacking her face with it!

He felt like a fucking porn star as she started talked dirty and took his cockhead into her mouth, suckling him, her tongue swirling. His big dick throbbed and spasmed in response; he'd never known such intense pleasure!

And this was just the beginning!

And there was something else welling up inside him. Something he'd never experienced before. Something truly exhilerating.

Power. Confidence. Strength!

As he looked down upon the gorgeous woman on her knees before him, worshipping his cock with her mouth, he felt, for the first time in his life, like a man.

"Fuck yes," he said, running his hands through her red curls... "Suck my dick you little slut..."

 

[Intensityrising]

She looked up at him as he ran his fingers through her hair. She took more of him into her mouth and then he called her a slut. It threw her off really, and she glanced up to see a different look in his eyes than ever before. Something had clicked it seemed, and he was finally getting what he had always dreamt about. A girl with her mouth wrapped around his cock.

Jennifer bobbed her head up and down the first couple of inches of his shaft and her hand gripped his base and stroked him in a twist motion. She pulled back and spit on his dick. "Did you just call me a slut?" She asked raising her eyebrow at him, "Don't call me a slut or I will use my teeth mister." She told him sliding him back into her mouth.

She moved her head up and down faster, trying to urge his load forth. She figured it would be best to get his premature virgin load out of the way, before play could begin for the main event.

 

[StFornicate]

Just about all Tommy could to do was groan and moan in pleasure as she worked him, and he nodded in response to her request, blushing a bit; apparently he'd watched a bit too much porn and fantasized about her!

She was aggressively sucking on him, her hand jerking him as she went to town, and he held her bouncing curls back to watch. It was a most erotic sight. Her lips stretched wide around his girth, her face moving back and forth, his cock plunging into her face again and again.

It was almost natural for his hips to get involved, and he started thrusting his cock a bit into her, even as his grip on her hair tightened...

"God that feels so good baby..." he said to her.

 

[Intensityrising]

Tommy was getting into it, moving his hips into her mouth. He told her it felt good and she fought back a smile. Instead she just kept sucking and stroking, moving faster and faster. For a virgin she was surprised that he hadn't blown his load already.

"Cum in my mouth Tommy. Let me drink you down." She moaned for him, her hand pumping him hard and fast.