Late Ch. 02

Story Info
Freddie gets anally massaged by his shemale coach.
10.7k words
4.79
150.1k
330

Part 2 of the 7 part series

Updated 10/18/2023
Created 07/28/2017
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Author note: Apologies for not uploading much, I don't have time for much writing but I am very thankful for all the feedback, I assure you that the other stories are (slowly) being written, I just don't want to sound like too much of a broken record with the writing, hopefully that's not the case! Also still no editor so apologies for any mistakes. Hope you all enjoy...

*****

Thursday evening.

Game day. The light was fading and Freddie was getting ready. But more importantly, his... date?... with his coach. Coach Matherson. Just the name sent shivers of desire up Freddie's spine.

His hands fumbled as he finished lacing up his worn cleats and tried to focus himself. Eyes on the ball. Focus. He needed to be sharp. But her beautiful, intense gaze swam into view and he found himself wondering what it would be like again to be forcibly taken by her... held down and roughly made out with, getting bitten on the neck...

Stop it. Freddie shook his head. Surely she wouldn't want him being such a pussy? And besides, these were unhelpful thoughts. Focus on the match. THEN the date... or whatever it was they were doing. He wasn't sure. In fact she hadn't texted since that training session, despite the messages he had sent back.

He looked at his chest of drawers in his small bedroom where he kept her underwear hidden, folded under his own. He'd sniffed them every night. He had even sent a message back to Coach, saying he liked the smells, and would love to see her wearing them... but immediately felt like a fool when he got no response that day. Or the day after.

Maybe she didn't want a response. Maybe that was just her teasing him. Maybe she was embarrassed that she'd even done anything with him, and she just wanted him to not turn up... Damn it, his head was doing circles, he needed to FOCUS!

Freddie glanced at his clock... 6.10pm?! Oh shit, 20 minutes!! Freddie dashed out of his room, flying past his shared flatmates in the living room and slammed the door, off down the hallway. Where was the car, where was the car... SHIT. Freddie hadn't fixed his flat tyre. And he had 18 minutes!! He ran over to the bus stop... Ah! Just as one was pulling up... He hopped on board and squeezed himself in beside an old lady, apologizing when he accidentally trod on some of her shopping.

He reckoned he would make it, and traffic seemed okay after rush hour. The trip seemed to take forever but somehow he was there in just over 10 minutes. He jumped out of the bus and flew down the road... 5 minutes; his feet hurt. He shouldn't have worn cleats before the game... 3 minutes, he could see the front entrance...

Freddie barrelled into the park, wheezing a bit as he managed to survey the familiar scene. Teams warming up under the lights, Umpire setting the game up. People in the tiny stands getting ready to watch their friends and family.

He jogged over as best he could to his team, grabbing a jersey, and began stretching with the team. He looked for Coach Matherson, but she was in the away dugout with the opposition coach, discussing things. Even to a fellow sportsperson, she made them look ordinary, and the opposition coach was not exactly an out of shape guy. But her confident body language and strong demeanour always gave the impression that she was in control. The other coach looked like a human being standing next to a goddess. A goddess with a baseball cap and a West Springfield insignia on her tight team T-shirt. (The West Springfield insignia had a wildcat on the front surrounded by stars. Not a bad look for an amateur team.)

He finished off his stretches as the umpire got the captains to toss. Small chants of, "we love you wildcats!" could be heard as Kevin, their team captain, shook hands with his opposite number and ran back to his team. They'd be batting first.

Freddie felt the familiar worms in his stomach. That means he'd be up soon. He wasn't one of their starting main batters, but he was close behind in the order. A great hitter on his day, sometimes he could win them a game with his accuracy and ability to steal bases. Consistency however, wasn't his strength, and at times he had lost his focus in important games and moments.

But today would be different

He felt like he was in control. His eyes glancing briefly to his coach who was now chatting with the umpire, her legs clad in what seemed to be sporting yoga-pants. He shook his head. "Focus..." he muttered to himself.

He took his place in the dugout, between Terry and Dean. Dean smiled as he sat down.

"So Freddie... does last Sunday's performance in training mean your official nickname is 'Little Bitch' now?" he snickered, as did many of the others in the team.

"Fuck" thought Freddie. He had hoped they wouldn't remember Coach's little wager with him for being late. God knows what they would think if they had seen them in the clubhouse.

Terry leaned over him and hissed, "Fuck you Dean, you're just jealous because you wish Coach would pay you any attention at all, limp dick!"

Dean grinned back but slightly less jovial then before, his team-mate's sudden language filled tirade (a particular trait of hers that friends like Freddie enjoyed) catching him off guard.

Freddie smiled at her. "Thanks noob"

Terry laughed and punched him on the arm. "No problem-o bitch"

Freddie sighed. It was definitely catching on...

"Alright people! Let's have a good game, and play to win!" Coach Matherson's voice cut across the conversations in the dugout, making everyone sit a little straighter. Freddie was caught up in her strong, charismatic aura, her foot planted firmly on the bench and her hands on her hips as she spoke.

"Kevin... you're up!"

The young man next to her in the dugout nodded and stood up.

Kevin was the best batsman in the team, and also team captain. He also happened to be solid, dependable, and an all round good person to have on your side. Walking calmly from the dugout, he took his position opposite the pitcher, who was also the opposing team's captain. The small crowd showed their appreciation for him. They were anticipating a good show, as he almost always made a decent score. Reliable, formidable, and a great captain; Kevin was one of their lynchpins.

First pitch... missed. The small crowd hollered in excitement. Nothing to worry about.

Second pitch... missed. The crowd still noisy, but there was a slight edge to that enthusiasm.

Third pitch... spooned. The ball travelled high, right above the opposition pitcher, the other team's captain. He caught it nonchalantly, smiling as he did so.

The stands, full of families and local friends, groaned. Kevin gripped his bat in frustration and made his way back to the dugout to polite applause. Terry up next.

"You got this," said Freddie, punching her lightly on the shoulder.

"Always!" she replied, winking at him as she got up.

She took her place and put a few practice swings in before settling into her pose. She was ready.

The pitch came in. Terry slammed it low, but one the of the fielders put a brilliant dive in to prevent it running away. She reached first base and realised it wasn't worth risking second. Not great. They were under pressure.

And then Dean walked up to the plate. Pitch, THWACK... and the ball sailed into the waiting hands of a fielder. The crowd groaned. Dean looked dumbstruck. They were in trouble. And Freddie was next.

Freddie needed a hit for his team to get points on the board in their first innings. He had been so engrossed in the game that he hadn't noticed Coach Matherson walking over to him.

"Get out there and show them what you've got," she said, her stare intense and serious.

He smiled at her but she walked away. Freddie's smile dropped as he realised that right now she was in no mood for games, although he was unable to take his eyes of her swaying ass as she walked back down the dugout.

He breathed out slowly and turned his head, making his way to the pitch.

Shouts of "come on Freddie!" were coming from some members of the crowd; who were starting to worry that this could be a horrendous afternoon for their team if someone didn't put a score in their first innings.

Freddie got in position and rolled his wrists a few times before crouching slightly into his familiar batting pose. He looked over at the opposition's captain, who was smirking slightly as he readied himself.

Pitch. A blur. THWACK. The ball hit the gloves behind him and he realised this guy was good. Hard to make a softball go that fast.

The ball went back and the pitcher readied himself.

Freddie rolled his wrists again and focused. He could do this.

His eyes flicked to the bench. There she was, emotionless.

He looked back in time to see the blur as the ball thwacked into the keeper's gloves again.

Freddie cursed himself and straightened up, breathing deeply as he shut out the crowd's nervous groans. He looked back. The Pitcher was sniggering slightly.

Freddie's lips tightened together and he placed both feet hard in position and rolled his wrists as the ball was put back to their captain. He threw the ball up a few times before turning...and firing in a fast low pitch.

THWACK!

Was the sound of Freddie's bat connecting like a thunderbolt to the ball, which was smacked straight back over the head of the pitcher. The crowd cheered as he began to run, his bench urging him on. Terry was already at second base as Freddie kept his head down, glancing only to see how far he'd hit. It was good, between two fielders, and he reckoned he could get the home run. He flew past second, trying not to spend any time looking at whether they had the ball yet. Third now, he looked over his left shoulder...the ball was in the hands of the pitcher! He was already past now and he watched agonizingly as the ball flew towards 4th base, and he realized he was going to lose this innings. "God what will Coach think now!" he thought, as he watched the ball fly in slow motion into the hands of the keeper... who, unbelievably, fumbled it.

Freddie flew across the base as the opposite team went from celebrating to gobsmacked to remonstrated angrily at their unfortunate keeper, whose head went down as the wildcats team cheered. Freddie slowed himself down, elated at having his second home run of the season.

He smiled as he came back, and looked up at Coach Matherson at the entrance to the dugouts. She looked at him without reaction, pausing only to turn to the rest of the bench and call up Stacey to the pitch. His smile dropped as he walked past, before being surrounded by his team-mates congratulating him. He managed to laugh as they shook him. He'd got them back in it!

The game continued, and with the momentum behind them, they began accruing runs, edging the first 2 innings but getting pegged back in the 3rd. And Coach Matherson was still acting like he didn't exist, even when he contributed well to the team. Her behaviour was beginning to irk him, despite him having no real grounds to feel that way. Maybe she regretted what had happened back in training. He brought his mind back to events on the pitch, which were approaching the final moments.

The last innings. The points were close... 10-9 to the West-Springfield wildcats. But the opposition still had a batter left to get out, and it was none other than the captain up next, the self-assured pitcher...a decent batsman, but not as formidable as the other side of his game.

Freddie was positioned in the outfield, as an okay catcher, but usually not needed when they had better natural catchers in the team. He watched as the first strike went in. Good. They were almost there.

Another glance at the bench to the Coach. She was focused on the pitcher, and hadn't noticed him watching. Damn she looked incredible.

Dean threw a curveball...and the batsman hammered it. God he loved it when she flicked her hair out of her face. Up and away. Ugh those sports yoga pants. Right for where Freddie was fielding... Oh shit.

He snapped back to the game and began back-tracking as he tried to place it's trajectory...it was going to land too far past him! He began to sprint, and launched himself up high and back, his glove high in the air.

He stretched.

Time slowed.

And the ball fell just inside his outstretched palm and he clenched it as he fell, hitting the deck hard on his back which made him cry out in pain.

But he had it. He had made the catch, the ball nestling in his glove. He lay there gasping. His back was aching hard, but they had won. His team were sprinting over to him, screaming and shouting to celebrate, and he laughed as they came down to congratulate him, wincing as they tried to pull him up before realising he was injured.

And then Coach was there. Stood tall, staring, still expressionless. He felt a pang of annoyance at her lack of enthusiasm. Did she even care that he had won them the game?

"Good catch Freddie... now what's the problem."

Freddie winced again. "My back... it's my back."

She raised an eyebrow before speaking. "Kevin, take him to one of the masseuses at the sports centre, probably a back spasm or muscle tension."

And with that she was gone, marching over to the opposition dugout, probably to shake hands with the opposition coach as she always did straight after a game. Kevin looked over at her as she walked away. "Huh, she didn't even smile and we just won!" he said confused.

He turned back to Freddie. "Don't sweat it man, you did great." He grinned as the rest of the team agreed with him. "Now let's get our coach's little bitch a back rub!" The team cheered, laughing at the use of his new nickname from the previous training session. Freddie's face went red and he was about to get annoyed but the team were still cheering as Kevin and Terry helped him up onto their shoulders despite his aching protests and began carrying him over to the sports centre in a walk of victory as dusk settled.

MEANWHILE

Coach Matherson cursed as she busied herself with packing the equipment away.

She was getting distracted. Every time she watched the field her eyes couldn't help but flick to him. His delicate features, his cute little butt... God she was going insane.

A bat left on the floor received a particularly harsh storage as she slammed it into the cupboard with the others.

He would never like a woman like her. No-one would like a woman like her. Water came to her eyes but she wiped them away and her expression became unreadable once more. She was stronger than that. She didn't need anyone.

She looked back out onto the field to see Freddie being helped towards the sports centre by her players, who were chanting and cheering. She wished she could think about sport right now.

But this boy had driven her wild. She had been completely unprofessional...she had nearly raped the boy in the clubhouse... even if he had enjoyed it, she noted. She had taken advantage of her position, and her powerful hold over him. It had taken serious self control to avoid ripping his pants off and taking him on the medical table.

But he had been erect because of her... She could see it every time she flattered him, or touched him... he would almost be ready to pop! And she was just his coach...he was still a full grown 23 year old man, and she was a 32 year old full grown woman (with a bit more growth besides). They were consenting adults, there was nothing in an Amateur league that said she COULDN'T have sexual relations with a member of her team...

She threw the last of the gear roughly into the store-room and locked it.

A sigh escaped her, and her eyes travelled down, feeling the urge to release her hidden desires. Her hand snaked her way into her pants and inside her thigh and she groaned as she released the beast tucked out of sight. Her boxers filled as a bulge appeared in her crotch, and she rubbed the material, feeling the heat from the thing inside it, thinking about all the things she could do with Freddie's body and her steadily growing organ.

She needed release...

Jane looked in the mirror at the toned calves, supple thighs... and boxers, tightly clinging to the massive shape trying to escape.

She smiled as she took in the sight. She loved her body. It made her feel good. But others didn't share the same excitement when she showed them how SHE preferred to use it. She wanted to be dominant... use her assets on a sexy, beautiful, submissive man. But it wasn't something that had really worked out well so far relationships-wise... ever.

She glumly kicked a softball into the cupboard, nearly taking out an old framed clubhouse photo in the process. She hadn't felt this excited about a man in months... or was it years? Ah what did it matter, she thought...he would never like her once he saw who she really was. What she really was...

She stared at herself in the mirror and sniffed, hands on hips.

She knew she was beautiful. She thought she deserved a man to make her happy on her terms.

Just one. Just one was all she needed.

But it will just be the same as before with Freddie. She could already see them getting scared away all over again. Her mind wandered as she her brain began to cycle through the small moments spent with him. He was reserved perhaps, but quietly handsome... capable of skill on the field if he pulled his finger out, brave when he needed to be, and would rise to a challenge given time. He had displayed so many of those qualities today. Not to mention his fine, fine ass...

Despite herself she bit her lip softly as she remembered staring at his derrier like an eagle as he had made his way up from the dugout. My God, she had needed to mentally chastise herself to prevent her from spanking his butt like the coaches from the movies... although if she had then everyone would want a fucking spank. She would probably have had them and half the opposition bench lining up for her one by one.

She decided to check on Freddie, but to say in no uncertain terms that nothing sexual would be happening between them. It was only a road to nowhere, and she'd gone down it too many times to expect a different outcome.

A vivid memory came up of her fingering him hard in the medical room, Freddie mewling as she finger-fucked his asshole. Coach shivered in pleasure.

Pushing it aside and steeling herself, she left the clubhouse and headed over to the sports centre.

MEANWHILE

Kevin and Terry finally took Freddie off their shoulders, having carried him all the way from the pitch to the sports centre via the club-house to drop his equipment off.

Elated, he breathed a few times to collect himself on the come-down from the game.

"Thanks guys... today's been awesome, and you guys were great..."

The team nodded in appreciation, smiles all round.

"But... I think I'll be able to get up the stairs okay," he said gently.

Kevin laughed at the words. "Haha, fair enough buddy. Good job today."

The team gave a smattering of applause and hearty agreements.

"Right chaps, let's get the warm down sorted!" he said as they began to move back to the club house. Freddie knew exactly what sort of warm down he was talking about. A healthy number of beers at the nearest bar most likely.

Terry remained, and slapped him on the shoulder which made him wince a bit.

"You da man Fred!" she said, before leaning in close and whispering: "Little Bitch."

She grinned like a maniac as she jogged off to join the others. Fred hadn't managed a comeback and sighed, thinking he'd have to do so at some point if he wanted the next few months to not be extremely damaging for his self-esteem.

He moved up the stairs gingerly, but the back seemed okay. Coach was probably right, just a spasm, hopefully some physio would do the trick. Thank God that's included in their monthly sports centre membership. He walked into the massage space, which seemed pretty quiet, and up to the small reception which housed a small girl with mousey red hair behind it.