tagMatureTommy's Neighbourhood Ch. 05

Tommy's Neighbourhood Ch. 05


I didn't achieve all my goals for Chapter 4, so this is kind of a busy Chapter.

Reading comments and feedback has been great, I put out the call for some feedback and I got it. Including one incredibly detailed plan for how to progress the series, but unfortunately it was anonymous and besides, I do have my own plan. As I kind of expected, results were about 50/50 for potential incest, which is where I personally was at as well. I'm going to follow both my editor, EndOfStory and the commenter who said I should just write what feels right, which is pretty obvious really.

So without further ado...

* * *

Dramatis Personae (Prior Chapters),/B>

Thomas (Tommy) Johnson. Age 19. Due to a condition when he was a small child, his body's development was stunted, though doctors assured that his growth would eventually catch up. He's blessed with a 6" dick that becomes 10" hard.

Amy Johnson, Tommy's single mother. Age 36. Amy has silky, shoulder length blonde hair and blue eyes. She works hard to provide a decent life for Tommy despite being a single parent and is extremely proud of her son's intelligence though she is over-protective of him physically. Tommy feels guilty for having checked out his Mum once or twice.

Pam Johnson, Tommy's Aunt and Amy's sister. Age 26. Her blonde hair hangs halfway down her back with light blue piercing eyes. She possesses high cheekbones, thin lips that are very rarely seen without a mischievous smirk, and a thin nose which makes her whole face very slender. She is much more liberal than her sister.

Brian Cherry, Tommy's best friend. Age 18. He and Tommy have been friends for most of their lives.

Vicki Cherry, Brian's mother. Age 40. 38DD-25-36. Olive skin, wavy brown hair styled like Farrah Fawcett, with thick, dick-sucking lips, and brown eyes. Vicki appears to be the doting, reserved, single mother, but underneath is a wild child. She took Tommy's virginity.

Brenda Bush, Tommy's teacher. Age 27. 34DD-26-34. Dark brunette hair, brown, almost sleepy-looking eyes, slightly thick nose, high cheekbones, pouting lips. Brenda has a weakness for students that has resulted in her getting fired a few times. Most recently, she's taken a strong liking to Tommy, and was the second woman Tommy slept with.

Ms Stern, Tommy's principal. Age 48. 52F-28-38. Honey blonde hair with highlights, hanging loosely down her back in a sort of wavy, 50's style when free, but normally bound up in a bun, and soft, green eyes. She behaves much as her name, sternly, but once she had Tommy in her office, it became quite obvious that she is a submissive, wanton cumslut. She is the third woman Tommy has fucked.

Heather Hancock, Tommy's neighbour and his Mum's best friend, recently separated. Age 31. 36F-23-36. Tommy's fourth 'conquest', Heather lured Tommy into her house where she had dominant sex with him and made him call her Mistress. Tommy was very unsure of himself, but somehow survived. The sex was great, but he's not sure he enjoyed being submissive.

Sarah, the receptionist at Sadler, Chisholm & Associates, the law firm handling Tommy's trust fund and owner of a 'phat, ghetto booty'. Age 22. Tommy noticed that she was very giggly, and something about her seemed a little unhinged.

Marge Sadler, one of the partners at Sadler, Chisholm & Associates and a close friend of Tommy's deceased Grandpa.

* * *

Tommy looked at the clock again. This was terrible, he'd only been late once before, and that was because Ms Stern, the principal, pulled him out of class and made him late, although the introduction to her heavily busty charms had been extremely worth it.

Part of him knew it was cool to be late, but mostly, he knew he wasn't cool, and he didn't want to be late. If he was late, he'd stand out as he walked into class late and everyone would look at him.

At least his homework was all done.


He looked out the window noting that there were no students left outside at all.

Again, he looked at the clock. It was going on ten minutes late. What excuse could he possibly use?

He didn't particularly like chemistry, and he found it took a lot more effort to get above average grades, so missing part of the class would likely leave him with the task of catching up.


The scarf sort of worked, though she was still pretty loud, and he fervently hoped no-one walking past could overhear. He'd been triply sure to lock the door at the start of lunch, so they were safe from anyone wandering in.

Tommy huffed and drove himself harder into Miss Bush.

She was bent over her desk, with a few papers and pens and things scattered around. Her skirt was flipped up over her back, with her panties having been discarded along with Tommy's pants and underwear. Her blouse had been unbuttoned and her front-clasping bra undone and thrown open wide. Her small, hardened nipples dragged across the top of her desk as her tits shook back and forth to the rhythm of Tommy's strokes. She pushed back against Tommy, helping him pound into her. Tommy alternated between taking a firm hold of her hips and sliding his hands around, caressing all over her hips.

He thrust his hips back and forth, sliding his rigid rod back and forth within her snug pussy. His pounding caused her to tire, and lower her chest to the desk, forcing her breasts to bulge out to her sides. Eventually, she went limp, her legs hung loose and floundered with her movements. Her spectacles clung, desperately to the end of her nose, threatening to fall off each time Tommy bottomed out.

But the most important thing, to both of them, was that Tommy's long, ten-inch, hard, solid slab of pussy-pleasing meat, was sliding ferociously in and out of his teacher, Brenda Bush's, desperate, clinging, sucking, slurping cock-sheath.

Tommy had her class that morning, and as he left, she'd dropped a piece of crushed paper and told him he'd dropped something. It told him to meet her in her office at the beginning of lunch. For the last hour they'd been fooling around in her office. She'd blown Tommy, he'd played with her tits, eaten her out, and now they were both furiously working towards their finale, but Tommy felt they were running low on time. When she'd started moaning louder and louder, he'd gotten worried and grabbed her scarf, trying to muffle her. She hadn't resisted and had even helped him push the scarf into her mouth.

Tommy bent over her back, cupping her buns and rubbing his body against hers. He reached forward, taking the tops of her big tits into his hands and using them to pull her back against him. He struggled to contain his own cries of pleasure, and somehow succeeded.

It was no good though, they needed to finish this now, but neither of them were quite there yet, they needed a push.

Tommy looked at her cute little rosebud arsehole. He'd never been too fascinated with it before, but he figured this might be just what they needed. He let go of her right breast and put his finger in his mouth to suck on it.

He stared, transfixed, with pumping hips, as his finger neared her little rosebud.

The moment he touched it, Brenda went rigid, cumming and screaming into her scarf. Her pussy fluttered, milking Tommy's rocket, and causing it to launch a semen assault against the depths of her love-tunnel. He again took hold of her hips, forcefully shoving himself against her, and his cock deep inside her. His eyes rolled back at the pleasure, as his cock lurched, firing blast after blast of potent seed.

They both lay still.

Suddenly Tommy remembered he was late. He unceremoniously pulled out of Brenda, causing her moan of protest to be heard through her scarf. Quickly, he pulled up his pants, before realising he'd forgotten his underwear. No time. He shoved his underwear into his bag and readied to leave.

"Sorry Miss Bush, I'm late, I have to go. You really are the most beautiful, awesome, sexy person I've ever met," he complimented as apology for running out.

Tommy fled down the hallway to class.

Having sex in her office was so extremely risky, Brenda thought to herself, but it made sex so hot. This was the first time she had managed to catch Tommy since the time she'd been confronted by Ms Stern. It had been a huge risk to slip Tommy a note the way she did, but she'd been careful to word it in a way that wouldn't be suspicious, and she hadn't even signed it. She'd known Tommy would work it out though, he was pretty sharp. She did her best to clean herself up, though Tommy had pumped a lot of his seed inside her, and it would take a while to drain out. She picked up her skirt to get dressed to use the restroom. She looked for her panties, they weren't on the floor, and they weren't wrapped up in her skirt. She searched the floor and they weren't there either. Her heart rate climbed. She'd lost her panties. Not for the first time, but it had cost her a job once before. She panted anxiously as she thought through possible scenarios. Tommy wouldn't do to her what Chris had done though, would he? Chris had turned out to be a spoiled snot who'd just wanted to have his cake and eat it too. Tommy was genuine, and honest, with integrity; he wouldn't try to have her fired. There was, of course, Ms Stern's involvement to consider. Still, she had to see Tommy again, and quickly at that.

* * *

Tommy scribbled furiously, taking notes, trying to get his head around the new chemistry formula, when there was a knock at the door. Mr Gregson went over to open it though Tommy paid it no mind until he heard her voice and looked up, shocked.

"Sorry to bother you Mr Gregson, and sorry for keeping Tommy and making him late, I'm not sure what he told you he was doing to make him late, but he was with me. He rushed off so quickly I didn't have time to give him a late pass," Miss Bush explained to her colleague.

She looked over at him with an anxious expression, probably worried that she'd made him late and gotten him into trouble.

"I see. Tommy hadn't really given an excuse and I was going to give him detention for it, but since he was with you, fair enough."

"Again, sorry for making him late, I'll let you get back to it," with that, she left.

Mr Gregson closed the door and looked over at Tommy, "Saved by Miss Bush it seems Mr Johnson. Let's not make a habit of tardiness though, shall we?"

"No Mr Gregson," Tommy answered, relieved, and got back to work.

He hadn't looked at her unusually in any way, Brenda thought. There was no malice, no smugness, and no humour in his expression. In fact, he'd looked relieved that she'd saved him from Mr Gregson. There was very little doubt in her mind now, that Tommy could be trusted. She'd have to ask him about her panties the next time she saw him though.

* * *

When Tommy got home he unpacked his bag, remembering his underwear was in his bag. It was strange, going commando, at first all he could think about was the breeze and the 'free' feeling, until he started thinking of other stuff, and then just forgot all about it. At least until he was hit by a draught of wind or something. It was also a bit harder to hide his erections, but Tommy always had to go out of his way to do that anyway.

As he pulled them out of his bag, something dropped to the floor. Suddenly the scent of Miss Bush had him remembering his passionate lunch time tryst with her. It was almost as if he could smell her perfume again. He looked down and noticed a crumpled piece of fabric on the floor.

Oh god, it was her panties. He remembered them well, white, with a T-string back. His room was quickly filling with the aroma of both her perfume and her natural scent. Or was that all in his head? Panicking, Tommy went to his dresser and stuffed them down in the bottom of the bottom drawer, where he kept a collection of clothes that he'd either outgrown or didn't like wearing.

There, they joined the blue pair of tiny panties he'd picked up when he left Ms Stern's office the other day.

He had two pairs of women's panties, hidden in his drawer. Was that wrong? Was he a perv? It wasn't like he'd stolen them. Miss Bush's were an accident, and Ms Stern's were to hide them from her bosses. He hadn't taken them out or looked at them, but he had to admit he'd thought about Ms Stern's panties in his drawer a couple of times at night, when he'd been jerking off. Maybe he was a perv, but he was a little scared of bringing the topic up to Ms Stern, not knowing if he'd be dealing with Ms Stern the principal or Ms Stern the cumslut. As for Miss Bush, he could return them and tell her it was an accident. He just had to hide them for now.

* * *

"I'm telling you Tommy, get an iPhone, everyone has one," Brian insisted.

"I don't know, I think the Samsung is better. It's newer and the apps aren't stuffed up by Apple's red tape," Tommy argued.

"That's half the problem with Android, they'll let any cowboy make an app, and the result is they don't work properly or they're designed to steal stuff off you."

They'd been discussing it all day, since Tommy was planning to buy a new phone with some of his trust money. They sat in Brian's den playing video games. Tommy was only half paying attention to Brian's game, the rest of his attention was alert for any signals that Brian's Mum may give him. He was hankering for another shot at Vicki. Despite the fact that he'd had fun with Miss Bush today, he was still pretty keen for some time with Vicki. But so far, he wasn't getting much from her.

"Maybe, I'll think about it," he answered. "Be right back."

"Ok." Something on the TV exploded, "Yeah! Take that you scum-sucking alien!" Brian shouted.

Tommy found Vicki in the kitchen, putting tea towels away. She was bent over, rummaging in the cupboard, causing her skirt to pull tight across her delicious buns. Tommy couldn't see a panty line anywhere. She turned to appraise him with a mischievous smile and stood up. She looked furtively towards the hall before lifting her arms wide and Tommy rushed forward to her, answering her smile with one of his own.

He wrapped his arms around her and filled his hands with her buns, giving them a squeeze.

She laughed softly, not wanting to alert Brian, "Frisky Tommy?" She herself gave Tommy's tush a squeeze.

Tommy whispered back to her, "Yes Vicki, you're so beautiful. I think about you all the time."

She chuckled again as Tommy felt her hand fondle the bulge in the front of his pants, "And does this tend to happen when you do?"

Tommy closed his eyes, bit his bottom lip and moaned softly, "MMmmmmmm."

Vicki stepped forward, pressing her big breasts into Tommy, and he moaned again as they pressed into his upper chest, "Mmmmm... Oh Vicki, I miss you."

"I miss you too Tommy. But we have to stop. I can't have Brian catch us," she said, apologetically as she stepped back and released Tommy's burgeoning manhood.

"I know," and he did, he didn't want to lose Brian's friendship.

Tommy looked down at the tent in the front of his pants. Vicki's eyes followed his. "But now I've got this problem..."

They grinned at each other.

"Sorry. I really shouldn't tease you. I don't mean to. I just wish we were alone."

"Me too," he replied.

Another explosion sounded from the game Brian was playing. "I should get back. Thanks Vicki."

Tommy placed his hand on her bum, leaned forwards and stretched upwards to place a kiss on her cheek. She took his head in her hands and placed a more sensual kiss on his lips.

"Don't worry, we'll get another chance soon. I'll make sure of it," Vicki said with a lopsided grin.

Smiling, they parted.

On the way down the hall Tommy adjusted his pants to try and hide his hard-on.

"Oh cool, you're already up to the mother ship!" Tommy exclaimed as he entered the room.

"Yeah, and check this out," Brian replied. His character switched weapons to an alien one Tommy hadn't seen before.

Ten minutes later, Tommy was finally focused on the game and his friendship with Brian. Occasionally, thoughts of his secret affair with Brian's Mum caused him a bit of guilt, but he justified it by thinking of the hurt and pain he'd cause both Brian and his Mum if it came out, and that thought chased away any temptation to tell Brian the truth.

* * *

"Okay, that's good, now keep easing the clutch out gradually until you're not putting any pressure on the pedal at all," his instructor continued.

Tommy grinned so wide his cheeks hurt. He was getting it now.

After he'd found out that he'd inherited his Grandpa's Charger, he knew he'd have to get his licence. Passing the learner test had been a piece of cake, as study and theory came easily to him.

The practical side of driving however was proving difficult.

Now he was taking lessons. His instructor often brought up how much easier it would be to drive a car with an automatic transmission, but Tommy was determined. He was showing progress now as well, and he couldn't be prouder.

They were nearly finished for the day. So far Tommy had just been learning on the big yard the instructors had. His Mum did let him drive her car, grudgingly, as she had accepted he had to learn how to drive in general, she was just worried about him driving a muscle car, especially an older model without modern features such as airbags.

He pulled up safely, and managed not to stall the car.

When he looked over the instructor was smiling at him, "You did well today. You're getting the hang of it. We might even get out on the road next time."

Tommy was still grinning, "Thanks." He unbuckled his belt and started to get out. "See you next time Jeff."

His Mum was waiting for him. For a moment he could see her expression trying to remain neutral, but when she saw him she succeeded at looking encouraging and supportive, though he knew she was forcing at least some of it.

"How'd you go today?" she asked.

"Great! I didn't stall it once, and I was much, much smoother," he replied excitedly.

"It's true, I think he's ready for the road in a manual now," Jeff added.

She smiled at him, "Okay, well let's get going."

They left the office and hopped into the car.

"Well, I need to get fuel, so you may as well learn how to do that today," she was letting a bit more of her true feelings show now, being a little terser.

They pulled into the local gas station. Tommy had sat in the car numerous times while his Mum pumped the gas, but today it was to be his turn.

It took him a moment of fumbling around to find the catch to the petrol filler tube, making him feel a little foolish, though his Mum didn't seem to notice.

Pumping the gas was pretty straightforward, surprisingly.

He clutched the $20 his Mum had given him and went into the store to pay.

He went up to the counter, feeling a little strange for being there to pay for gas instead of soft drinks or chips.

The girl at the counter was reading a magazine, one of those trendy fashion ones from what Tommy could see. Her hair was blonde, but had been dyed all different shades in streaks, giving her a sort of dirty look. That's what Tommy thought anyway. Her expression was very open, honest, but her makeup tried to subvert that, dark eye shadow and lipstick. She was wearing a tight, black sweater, with a deep v-neck which would have shown quite a lot of cleavage if she hadn't been wearing a pink T-shirt underneath, which covered most of her cleavage but left some on display.

She noticed Tommy and put aside her magazine to face Tommy. Her face looked familiar. Her name tag read Janine, and Tommy realised that she'd graduated from his school last year, as he'd seen her in the halls. That made her about Tommy's age.

She had bright blue, shining, open eyes.

"Just the gas?" she asked.

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