tagMatureTommy's Neighbourhood Ch. 06

Tommy's Neighbourhood Ch. 06


Thanks to EndOfStory my forgiving and tireless editor.

Feedback is always so important, so remember to comment or send me direct feedback, no matter how long the gap is between me posting the story and you reading it. Getting feedback often draws me into writing a bit more on one of these stories, so if you like it, make your contribution by dropping a bit of feedback. And to all those who have, my sincere thanks to all of you.

Longest chapter so far. If that's disappointing, I apologise. I can't promise they'll get shorter, longer or stay the same; they are as long as they are.

In case you haven't noticed, Tommy usually gets some action from more than one lovely female each chapter and that continues here. Mostly they are ladies who are older than him, so Tommy will remain under Mature, but he won't only be into Mature ladies.

So without further ado...

* * *

Dramatis Personae (Prior Chapters)

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 is feels guilty for having checked out his Mum once or twice.

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. 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 is the receptionist at Sadler, Chisholm & Associates. Age 22. 44F-30-42. She works at the law firm handling Tommy's trust fund and is the owner of a 'phat, ghetto booty'. She has a very vivid imagination and derives pleasure out of living them out, without letting her partners know.

Janine is a dirty-blond service station cashier that graduated from Tommy's High School last year. Age 19.

* * *

This was amazing.

There was simply no way to describe the feeling.

The bliss Tommy was experiencing was simply out of this world.

Absolutely no doubt about it, driving his car along this winding road was awesome.

Tommy had passed his test and received his licence, and had now been driving for about a week.

This was his first chance to get out into some winding roads and simply drive, rather than transitioning between locations, and he was thoroughly enjoying it.

He was still a little scared by it all, driving out on his own, and there was no denying the power that rested just below his right foot. He was still extremely careful when pushing down the accelerator, but despite that he'd had a couple of close calls already. He was getting better though.

Oh well, time to actually get something done today, he thought as he headed back towards home.

* * *

"I didn't even know she liked me," Brian was telling him, "until Josie slipped me the note in Maths."

Tommy continued to listen, smiling at his friend's confusion.

"I mean, she is a little nerdy, with those glasses, but I think she's cute, right?"

"Sure," Tommy replied, grinning.

"Do you think... do you think I should ask her out?" Brian asked, tentatively.

"Are you kidding me? We've never had a date, and now a girl sends you a note telling you she likes you? Of course you should ask her out! If you don't you're an idiot."

"Right... of course," Brian replied, looking nervous. "But how? I don't want to look like an idiot."

They both stopped to think about it.

"Maybe you could ask her after school? Wait until she says goodbye to her friends?" Tommy suggested.

"That could work, making sure no-one's around to laugh if she says no... What if she says no Tommy?" Brian worried.

"She won't. She sent you a note already saying she liked you," Tommy said.

Melissa, or Lissa, as everyone called her, was part of the female group of nerds at school. Despite the fact that they had a lot in common, Brian and Tommy had never really paid too much attention to them. But now Brian was all aflutter over one of them, thinking himself into knots.

* * *

Tommy was driving Brian home from school that day when they had one of their worst disagreements.

"No way! I can't believe we're even having this discussion!" Tommy all but shouted.

"I don't see what the big deal is, I lend you my games all the time," Brian pleaded.

"That is not even remotely the same Brian!" Tommy shouted, getting angry.

Suddenly a car pulled out ahead of them and Tommy slammed on the brakes, swerving to the side. He mounted the footpath and the car bounced a bit before coming to a stop, miraculously avoiding all hazards.

Tommy and Brian both stared ahead for a moment before looking at each other.

Tommy switched off the engine and hopped out to meet the elderly lady who'd been driving the other car.

"I'm so sorry. I didn't see you," she said.

Tommy was angry, but seeing the apologetic lady caused his anger to dissipate, especially since there was no damage.

"That's ok. Just be more careful." He thought about telling her he was a new driver, but didn't see the point. She didn't say that he did anything wrong after all.

He wondered if he could have done things better if he hadn't been arguing with Brian. His Mum hadn't wanted him to take any passengers at all for a while, saying that they'd be a distraction, and he was starting to believe her.

He got back in the car and turned to Brian.

"I'm sorry Tommy. I shouldn't have asked, let's just forget about it."

"That's ok, Brian. But I'm just not ready to lend you my car, I only just got my licence and besides, this car was my Grandpa's and he left it to me, I have to respect that."

"No worries."

Tommy started the car and carefully backed back onto the street and drove on.

After a few minutes of silence he asked, "Hey, what about if you gave us a lift? I know that's a big favour, but I really don't want to have to get my Mum to drive us."

On the whole, it wasn't a big deal. It was kind of lame to act as his friend's chauffeur for his first date, but it was better than lending out his car, so he agreed, "Ok, I'll drive you both."

"Thanks Tommy."

* * *

"Brian told me what you're doing for him, Tommy," Vicki told him, with a wide, warm smile on her face. "I'm so proud of you; you really are a very nice boy. Brian is very lucky to have you as a friend."

'Boy' hurt him just a bit, but this was still his friend's Mum, so it wasn't that unusual. Although they'd had sex a couple of times now, so surely he rated something more than 'boy'.

He shrugged and said, "That's ok, I don't mind."

"He also told me he asked to borrow your car and you let him know he couldn't. You did the right thing. Now, what are you going to do while they're at the movie?" she asked.

"I don't know, hang around the mall? Maybe take a book to read or something? I really don't want to see that chick flick and besides, he doesn't want me in on his first date, and I wouldn't want to be there for that anyway."

"Well, maybe I could come to the mall as well."

For just a moment, the thought of them together at the mall, on a date appeared in Tommy's mind. He looked at her, but couldn't fathom whether or not that is what she was suggesting.

"Ok," he said, guardedly.

She smiled, "I actually thought we could do some shopping?"

He imagined following her through clothing stores and underwear stores, watching her model different outfits. That definitely sounded better than when he used to have to follow his Mum around as a kid.

"I really think you could use some new clothes."

She meant shopping for him? Tommy inadvertently rolled his eyes, but Vicki saw it immediately.

"Now don't be like that Tommy. You're going to Uni soon, and eventually you might want to take a nice college girl out on a date too, and your Spiderman and Serenity T-shirts, despite how cool you think they are, aren't up to the task of attracting a hot college chick."

Tommy winced inwardly when she mentioned taking a girl on a date. It had been a growing, nagging issue for him without having someone else point it out to him. While he never really pictured himself and Vicki on a date, it still hurt a bit to hear that from her.

"Okay," he said.

Vicki grinned at him and punched him lightly on the arm, "Buck up stud, I'm sure you'll enjoy it."

"It's your turn Tommy!" Brian yelled from the den.

"Coming," Tommy called back and gave Vicki a lopsided smile before heading back down the hallway.

* * *

Vicki had given some thought to her proposed mall visit with Tommy. She'd been feeling a little guilty for using him, and had decided to do something for him. She was going to take him shopping, really shopping, and give him some style tips. She was a bit of a social butterfly and always took note of style and fashion that she observed when she was out and about, so she was confident she could help Tommy like that.

However, she was a little worried about being seen shopping at the mall with one of her son's friends, so she'd decided to make a phone call.


"Hi Amy, it's Vicki Cherry, how are you?"

"Hi Vicki, good actually. Yourself?"

"Yes, not too bad, still adjusting a little bit to having scumbag gone... oh, please don't tell Brian or Tommy I called him that."

Amy laughed, "Ha ha ha, your secret is safe with me. So how is Brian and how is he coping?"

Vicki sighed, "Not too bad. We've both tried to make this about us and not let Brian feel in any way involved, but all divorcing couples says that, and every child always feels involved, how can they not. Brian seems to be doing ok though, he just misses his father. Although to be honest, he probably sees his father a little more these days anyway. Personally though, it's hard not to feel bitter at him."

"Well he certainly doesn't appear to be acting any different around here, still eating me out of fridge and pantry," she giggled.

"I'm so sorry Amy," Vicki apologised.

"No, no, not at all Amy, I love having him over here, although they definitely seem to be at your place more often."

Vicki was sure Amy knew it was because Brian simply had more stuff, but there was no need to discuss that.

"It's fine. Anyway, the reason I was calling is kind of exciting."


"Yes, I found out that Brian asked a girl out to the movies on Friday."

"Really?" Amy knew that neither of their sons had dated at all in High School, and Vicki had always seen that as a problem. She gathered that Vicki had been a bit of a wild child until she married. Their sons had been friends throughout High School, and so they'd gotten to know one another on a casual basis, occasionally getting together for a barbeque or something similar, but they certainly weren't close friends. She'd also heard that perhaps Vicki wasn't finished being wild, now that she was divorced. She was happy that Brian was going on a date, although she was just a tad jealous that it wasn't her Tommy dating, not that she wanted him hanging around some trollop.

"Yes, I'm so excited for him. He actually asked to borrow Tommy's new car for the occasion-" Amy gasped, "-but Tommy put a stop to that, and rightly so. But Tommy did agree to chauffeur them for the night. Apparently Brian doesn't want his cool Mum getting in the way and showing his girl how he can't compete on coolness with his Mum."

That sounded exactly like a Vicki thing to say, Amy thought.

"So, I asked Tommy what he was doing while they were at the movies, and he didn't have a very good answer. So I suggested we go shopping."

Why was Vicki trying to take her son shopping? Did she think Tommy needed some kind of handout? How dare she stick her nose in like this!

Vicki knew how sensitive and independent Amy could be, so had prepared to cover her bases.

"He was just telling me how he wanted to take you shopping because you've been so busy working lately. Then he didn't want to ask you and make you feel obliged to go with him, so he was just going to go without you. But I knew you wouldn't want him spending all that trust money, so I was going to go along and keep an eye on him. Then I thought it would be a great surprise if you were there as well. What do you think?"

It sounded a bit flimsy, but she could see Tommy behaving that way.

"Well, I'm actually free on Friday night."

"Great. Tommy is picking Brian up about 6:00PM; I'll pick you up at 6:30PM. See you then Amy. Bye."

Vicki then hung up before Amy could protest about driving herself.

* * *

Tommy picked up Brian on time. He was a mess of nerves. He even suggested they should just go back home, sure that she would have already gone out to do something else.

Tommy just did his best to assure his friend that it would all work out ok.

When they got to Lissa's house, Brian again suggested they just go to the movies themselves, but Tommy forced him out.

He watched Brian ring the doorbell and look back at the car, like he was considering making a run for it.

Instead, Lissa came out wearing a very nice dress, and she was even wearing a pair of glasses that were much more stylish than those she wore at school.

Brian had started to hop in the front of the car after Lissa got in the back but Tommy motioned with his head that he should sit in the back with Lissa.

Before he left, a man came out and spoke to him through the open passenger window.

"You drive carefully now Tommy. If you don't, you'll have to deal with me," he warned.

"Yes sir," Tommy replied, sincerely.

"Okay Dad, can we go now?" Lissa asked petulantly.

"Okay. Back by 10:30PM," he reminded her.

"I'll do my best Dad," she answered him.

It was obvious there had been a few long discussions. He stepped back from the car and allowed Tommy to drive away. Tommy did his best to drive those first few hundred metres the best he ever had.

In the car, it was obvious they were both nervous. Tommy stayed completely silent though, beyond responding to a couple of questions Lissa asked him. He paid attention though, as he knew this was a proper date, not what he'd been experiencing.

Lissa asked Brian if he liked her glasses and explained that after having broken a few pairs when she was younger, her 'nice' glasses were reserved for special occasions. Her Mum had allowed them out tonight.

When he got to the mall, Tommy decided to let them out before he found a parking space, since that would make things a little less awkward since they were splitting up.

Once he had parked the car in the shopping complex, locked the car and armed the alarm, he headed inside.

Vicki had suggested they meet by the juice bar.

As he waited, he recognised Janine, the service station attendant, going into a lingerie store. He immediately pictured her trying on bras, struggling to close them around her large breasts. His cock stirred and he realised he had to think of something boring, and quickly.

His phone beeped with a text from Vicki, 'On our way.'

Our way? Who was she with?

He was soon answered when he saw his Mum walking with Vicki.

"Hi Mum, I didn't know you were coming?"

"Mrs Cherry thought it would be a nice surprise," she replied.

He could tell she wasn't too sure that this was a good idea. To be honest, he was happy she wasn't working. He actually thought it would be a good chance to pick her up something special.

"I'm glad you're here," he told her, and she seemed to brighten a bit at that.

They started going into stores, and Vicki soon showed her shopping prowess, directing the Johnsons around like a pro. She even coerced Tommy into some clothes that at first he said he hated.

About an hour into it, Tommy found himself in a changing room having just taken off the store clothes and getting ready to get back into his own.

Suddenly the door burst open and Vicki slipped inside.

Tommy was shocked, "What--"

"Shhhh, we don't have long. Your Mum stepped out to use the bathroom, so I have to make this quick," she told him.

Tommy was standing in nothing but his green y-fronts, when Vicki dropped quietly to her knees and gently held his softened cock, which was currently aligned towards his left hip. She gave it a light squeeze.

Then she pulled his underwear all the way down to his ankles.

Tommy spoke anxiously, but tried to keep it to a whisper, "What are you doing? Someone will catch us!"

Vicki wasted no time talking to him, instead slipping the head of his cock into her mouth and caressing it with her tongue.

"Ohhhhhhh..." he moaned.

"Mmm," she moaned trying to grab his attention. 'Oh of course,' he thought, 'be quiet'.

His rod hardened up quickly, and Vicki started to take more of it in.

Her soft lips slid back and forth, caressing his shaft, while her tongue tickled his flared helmet on every backstroke.

Tommy's head dropped back and he brought his hands up to slide his fingers through her wavy, middle-of-her-back length, brunette locks.

"Mmmm," he moaned.

In response, he felt Vicki nip him with her teeth.

"Oh!" he gasped. It wasn't hard at all; merely enough to let him know her teeth were there. He took the point that he had to be completely silent.

It was a challenge to remain completely silent while Vicki worked her soft mouth up and down on his rod, sucking on it and trying to pull out his cream.

He looked down at her, he could see her arse filling out the tight, denim jeans she wore, with just the barest hint of the black panties she wore, only visible because of his high vantage point. Her brunette hair swung to and fro with her motions, obscuring her neck. Her stretchy, black top left only a thin midriff visible, mostly covering her up.

He reached down to give her breasts a light squeeze, and caress their rounded shapes.

"Everything ok in there?" she shop assistant called into the changing area.

Oh shit, they were busted! She wasn't ordering them out though. Okay, she really only asked if he was okay. He should answer.

"Yep," he said, his voice several octaves too high and breaking as well.

He might have heard a light giggle but couldn't be too sure. "Okay, just call out if you need anything," she said, before silence resumed.

Silence, aside from the faint, wet slurping Vicki was making as she worked back and forth along Tommy's cock, ensued.

Report Story

byTheTitLover© 19 comments/ 129457 views/ 104 favorites

Share the love

Report a Bug

10 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: