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First off the rank is thanks to HMauthor for their work on the editing.
Secondly, my profoundest apologies for how long this next chapter has taken. Chapter 6 was monstrous as those of you who read through it can attest, and I also understand I was testing a lot of fans’ tolerances for long stories too. It also took a lot of effort for me. To a degree, I needed to step away from Tommy for a little while. If you read any of my other stories you’ll see I’ve certainly spread my wings literately.
In an effort to address the long chapter, I’m going to try a different approach and split this chapter up into sub chapters. So far, Tommy has bedded a new woman each chapter, as well as meeting a new woman he usually beds in the next chapter. Plus Tommy stories are a bit more than wham-bam stroke stories, there’s a lot of plot and character development. In addition, some of you expressed an interest in continuing adventures with prior women, where my original plan was almost a one-night-stand arrangement. This means that each chapter needs to be bigger than the last, even if I don’t get to every woman in the ‘stable’ every chapter.
Some of you may ask why each sub chapter is not simply a chapter by itself? I don’t have a good answer to this question, but mentally I plan to achieve certain things in each chapter and if I think of a sub chapter as a full chapter, they will be monstrous every time. You’ll also understand from the structure I’ll explain below.
So, this will be Chapter 7.01. The first sub chapter in each chapter will attempt to stick to my original plan, introduce a new woman and bed a new woman. This will also likely be the chapter with the most plot and character development. Following sub chapters will hopefully be shorter, throwaway romps with some of the various women Tommy has met. I’m sure there’s a better term than throwaway, but what I mean is you should be able to skip them without missing any plot developments. That’s the plan anyway.
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 you. In fact, this current resurgence was due to your feedback.
This is, as with most of Tommy’s adventures, a mature adventure, however, since it included his first anal encounter, I thought the category should reflect that.
* * *
Dramatis Personae (Prior Chapters)
Thomas (Tommy) Johnson. Age 19. Due to a condition when he was young his body’s development was stunted, though doctors predicted 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 physically over-protective of him. Tommy feels guilty for having checked out his Mum once or twice.
Janine is a dirty-blond service station cashier and clothing store retail assistant. Age 19. Janine graduated from Tommy’s High School last year. Her parents are quite wealthy, but due to Janine being punished, she no longer has access to that wealth aside from a place to live. She’s working two jobs to have spending money before she decides what she wants to do with her life. She saved her number into Tommy’s phone as J-Star.
Miss Tait is the head Librarian at Tommy’s local library. Tommy often thought of her as his “mother at the library” when he was little as she often kept a close eye on him while he was at the library and always took an interest in him.
* * *
Tommy drove home, struggling to stay under the speed limit. He was so excited about getting Janine, or J-Star’s number that his excitement was bubbling out through his foot to the accelerator. A small part of him felt a bit lame for being excited over something so trivial, but it was a tiny voice overshadowed by an orchestra of jubilation. Tommy had no context to realise having sex with a woman was often the goal of a date, so by most guys’ standards he had been incredibly successful with women so far. Regardless, he now had a sniff of a proper date.
Before driving away he’d texted his Mum to say he was driving home. If she’d been calling about something super urgent she’d call again and he’d pull over and take the call, but so far silence.
* * *
When he got home his Mum was clearly agitated, pacing around the kitchen.
“Alright,” she began, “I know you’re not a little kid anymore and that car gives you freedom. And believe me I really am trying to let go a little; to let you grow up and be the man you’re going to be. But this isn’t easy, Thomas.”
“Mum, I—” he replied before being cut off.
“I’m still your Mother, illegal bahis and you could have a bit of respect for me. The shops shut hours ago and you never came home. I was worried about you. Where were you? I thought maybe you might have had an accident and been lying on the side of the road or tangled in a wreck waiting to die.”
She was starting to tear up, so Tommy stepped forward and embraced her. Feeling his comfort, she let the tears flow and started sobbing.
“I know I’m overreacting,” she told him between sobs, “but for a long time you’ve been the most, if not the only important thing in my life, Tommy. I can’t just switch that off overnight. You have to give me something to work with.”
Tommy struggled coming up with an excuse for where he was. Should he tell her he was with a girl? Would that make her happy or suspicious? He tried to think of an excuse.
“I’m sorry, Mum, I just went driving around for a while.” Flimsy, but didn’t require any corroboration.
She squeezed him extra tight and again his attention was drawn to the fact that her big tits were pressed, bulging, between them. Tommy immediately started trying to think unsexy thoughts but came up empty.
Amy sniffed as she held onto her son. Part of her wished she could go back in time and somehow freeze Tommy at 17 and keep him her diligent, loving, caring son, but she knew that was unrealistic. She didn’t really want to limit her son that way, but this was one of the toughest things she’d ever faced as a mother. She did have a fleeting thought that she was lucky in that there were a lot of problem children out there with behavioural and drug-related issues. She was proud that she’d raised Tommy right and that he’d never had such issues. Her tears slowed. She realised that Tommy was twisting strangely, a habit he’d exhibited lately when they hugged. Didn’t he want to hug her anymore? Using her emotional state as a bit of an excuse, she grabbed him tightly and pulled him in unprepared for what she’d encounter.
Tommy performed what was becoming a practised manoeuvre to keep his Mum from feeling his slowly erecting cock. As her tears dwindled though, she suddenly pulled him in tight and his eyes shot open in shock as there was simply no possible way she’d not be able to feel his erection against her leg. He froze, not moving and wishing for there to be some way for it to be over without embarrassment.
‘Oh,’ Amy thought, ‘so that’s what’s going on. He’s trying not to let me feel his stiffy. But that would mean that…’ Amy’s mind began to run with all kinds of thoughts, such as the fact that he’d been having stiffies for a while now; and wondering, since he was getting them or at least having them while the two of them were hugging, was he attracted to her?
Her grip slackened, and Tommy gingerly extricated himself from her embrace. He pulled back, keeping his eyes down at the floor, not wanting to meet her gaze, completely unsure of how she would react.
“Okay, well, I’ll try to remember to call you next time, or at least send you a text. G’night, Mum,” he said as he slunk away to his room.
It was a long time before Amy realised that her son, and his stiffy, had left the room.
* * *
Tommy stared at his phone for hours that night, working up the courage to call or text Janine. He wasn’t an idiot, he’d seen plenty of TV shows and films that suggested the rule was to wait three days before contacting the other party.
Finally, Tommy worked up the courage and pressed the button on his phone to dial her number. Before he even got the phone to his ear though he realised he had no idea what to say. He hurriedly cancelled the call, hopeful that he’d cancelled it before the call went through to her phone.
The excitement had him breathing heavily.
What the hell would he say? He’d left her house with a vague agreement that they would go to a movie, following a brief conversation as she lay sexually exhausted in her bed. Maybe, ‘Hey, great sex tonight, how are you?’ Maybe that three day rule wasn’t so ridiculous after all.
* * *
Later that week, Tommy was hanging out in his room, still struggling to call Janine. He’d put it off past the three days now, which was causing him grief, but he’d poorly justified it by saying that the three days was just a guideline. He’d slept with some women but hadn’t had a real relationship, and now here was the beginning of an actual relationship and he found himself unable to even call her. It was making him feel like a real loser but he just couldn’t bring himself to make that call.
Looking for something to distract himself, he noticed the books he’d borrowed from the library. They weren’t due back yet, but he needed something to do so he decided to return them. He picked them up and headed out towards his car.
He was just about to open the door when he remembered something important.
“Mum, I’m going to return some books and then I’m probably going to drive around a bit, so don’t worry about me.”
“Ok, illegal bahis siteleri but be careful and don’t stay out too late. If I get worried, I’m going to call you, and if you don’t answer I’ll worry and start calling hospitals and the police,” she answered as she walked out of the lounge with a smirk on her face. “You wouldn’t want me to worry like that would you?”
Exaggeratedly rolling his eyes, having picked up on his Mum’s jovial tone, he replied, “Mum, you’re so embarrassing… god… jeez… but no, I won’t let you worry.”
With that he headed out to his car, fired it up and luxuriated in its throaty rumble before letting it idle to warm up. Sure, a more modern car wouldn’t need such extra special care and attention, but it also wouldn’t have as much character, or be a treasured gift from his grandfather.
* * *
Tommy looked over at the clock and realised he was going to miss the library. Driving his car was such an enjoyable experience that occasionally, once he started driving he found himself completely distracted from tasks if they weren’t important.
Still, he could just drop the books in the after-hours return chute anyway. With that in mind, he started making his way towards the library.
As he expected, a lot of the lights had been turned off, but it still looked like someone was there as there were more lights on than he’d expect to see if it was closed.
He pulled up and turned off the engine, and then realised he wasn’t going to be long and could have left the engine running. He approached the chute in the window, books in hand.
“AHHHH!” he yelled, startled.
As he got close to the chute, someone had appeared in front of him, inside the library, as if from thin air. The shock had caused him to cry out. He recognised Miss Tait waving at him. Her usually perfectly straight brunette hair was a little messed and hanging from a slowly failing ponytail. Her deep green eyes were a little alert, and to be honest, she looked a little harried.
“Thomas!” he assumed she shouted, but he couldn’t hear anything through the glass. The soundproofing at the library was impressive.
He waved at her and pushed the books through the chute, before pointing to his ears, shaking his head and shrugging his shoulders.
Miss Tait lifted both her hands and signalled to Tommy to stop or stay or something, before she hurried away in the direction of the front door.
Curious, Tommy headed that way too.
She hurriedly unlocked the door and it opened automatically.
“Thomas, I’m so glad to see you. I know this is unusual, but I was hoping you might be able to give me a hand?” she asked, clasping her hands in front of her around the level of her crotch.
Before he could reply, Tommy was distracted by the sight of her. The overall impression Miss Tait gave was that she was hot and had been working hard. Her face was just slightly sweaty, and he was pretty sure he could see slightly dark patches under her arms. Her ponytail was clearly failing with strands and wisps of hair already having made a break for freedom. She wore a high-collared white blouse with a ruffle along either side of the buttons. Not a button was undone, not an inch of cleavage was visible. But that didn’t matter, because the blouse was tight, it ballooned out to accommodate her prodigious bust before sloping back in to be tightly tucked in to the high waist of her skirt. Her sleeves were rolled up to her forearms. Her grey, speckled skirt hung down to just above her ankles and looked to be quite billowy and diaphanous. Her wide hips were clearly outlined by the skirt.
“Erm, sure. What with?” he asked.
“Well, it’s actually pretty mundane stuff, mostly returning books to shelves. There’s an inspection tomorrow and unfortunately this week we’ve had non-stop excursions through the library which has put a huge backlog through the return to shelves function. On top of that, I’ve had several staff call in sick this week. The inspection usually wouldn’t matter, but I’ve heard that I’m up for review this year and one woman in particular would like to see me ousted to make room for her sister in this role. I worked so hard for this, Thomas, that I really don’t want to lose it. Unfortunately it’s just me left and there’re a few things I need help with.”
Tommy put his hand on her arm comfortingly and said, “No problem, Miss Tait, I’ll help you. I know how much you care about the library.”
She led him to the room that held the books waiting to be returned. Frankly, he was a little astonished at the volume.
“Sorry, I tried to get a few of the staff to stay back, but so many of them have children.”
“That’s ok. Where do we start?”
Miss Tait got him a trolley and showed him how to work through the piles. Fortunately, a couple of volunteers had organised the stacks so that aside from the occasional maverick, out-of-place book that was stacked on the wrong pile, they were well grouped. They both got to work.
* * *
Kat knew canlı bahis siteleri she was returning books at about twice the rate that Thomas was, but it was still a third that she wouldn’t have to do herself. She was a little bit miffed at the staff and had wondered many times over the last day or so if some of them were trying to sabotage her. Perhaps she was less respected or liked than she had always thought. She would normally have expected a few of them to help out in a time of need like this. Thomas driving up was a god-send. After he helped her return all the books there were still a few things she had to do so his help was invaluable.
Tommy crossed paths with Miss Tait several times, and every time he did so he was taking the opportunity to check her out. Her skirt had turned out to be very see-through and he had to wonder if this was normal library attire.
He was doing his best not to count or keep track of how much they had done or how much was left as he knew that would make the whole task seem endless. He couldn’t help but notice it seemed like they were getting to the end of the piles though.
She divided up a few more tasks, giving Tommy the simpler ones of course.
About 15 minutes later he returned and it seemed Miss Tait was waiting for him.
“Thomas, great, I just need your help with one more thing and then we’ll be done. These books go up high and I really hate climbing the ladder without someone to steady it, so off we go,” she directed, before leading Tommy back into the labyrinth of shelves.
She led the way through the reference section.
“These have been off the shelves for weeks and really should have been put back a long time ago.”
She positioned a ladder that she must have left in the row earlier. She climbed up before Tommy even had a chance to offer to climb up. He held the ladder steady and slowly passed up the six or so books.
Miss Tait bustled around up at the top of the ladder. In hindsight, he really should have been the one up the ladder while she steadied it for him. Standing this close to her, with his upward view, he was able to see a lot that he figured he wasn’t supposed to. He could see the crease in her leg, where her thick, curvy thigh ran smack-bang into her bulging shelf of an ass. From close up he could also see the way her skirt dipped at the back, defining the precise location of her undoubtedly deep arse-crack. He was in awe of the size of her arse. Her waist was really quite skinny, yet her bum ballooned out and almost defined what people meant when they used the term ‘shelf’.
“Okay,” she said as she suddenly started descending the ladder.
Tommy wasn’t prepared for her sudden movement, and as she moved the ladder lurched to the side. She lost her balance and slipped down the ladder.
“Ah!” she yelped as she fell.
Tommy managed to halt the ladder’s movement, and she was able to slow her fall quite a lot as she scrabbled to grip or stand on the rungs. Tommy kept his place beneath Miss Tait as she dropped.
As she fell, her skirt billowed up quite quickly and exposed her legs to Tommy’s gawking eyesight. To top it off, her panties quickly came into view, a tight pair of yellow, Lycra panties. He wasn’t so experienced or knowledgeable, but he’d heard of boyshorts, and they didn’t seem to fit, as they seemed very high up her leg, and the back was almost like a thong or something, as he could see a lot of her arse, but unlike a thong, there was a lot of material at the back, covering the small of her back really. Her arse was divine.
It was almost like something from a slapstick comedy, as Miss Tait’s round, voluminous arse dove towards Tommy. It happened to Tommy as if it were in slow-motion. Each of her cheeks collided with one of his own cheeks, although it was her arse to Tommy’s face. His nose went deep, exploring the depths of her bum crack in which her panties disappeared. He got the briefest whiff of her scent as her rump continued its grind down his face. Involuntarily, with reflexes he didn’t know he possessed, his tongue shot from his mouth to taste the slightly sweaty, salty skin of her delicious buns.
The sheer shelf of her arse stuck out so far that as she continued to slide down in front of Tommy, it was only her arse that touched him. The soft, plushy cushions of her tush passed down, slipping from Tommy’s chin to collide with his chest. Each globe bulged against his chest, the near-naked flesh caressed its way down to his abdomen.
By the time Miss Tait was able to catch herself, her tantalising arse was wrapped tightly around Tommy’s hardened cock, with his pants providing the only insulation from feeling her pale, soft skin against his turgid rod.
“Oh Tommy, thank… god… you…” she said before tapering off to stunned silence.
Clearly she could feel his big hard-on between her supple arse cheeks.
“Thank you for catching me, Thomas,” she said, recovering.
He felt her start to rise and try to twist within his arms, as he still held the ladder, arms either side of her skinny waist.
Tommy didn’t release her though. Her skirt was still hiked up and he was enjoying the view of her massive derriere caressing his cock through his pants.
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