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.
