The Trials of Jack Matthews - Chapter 4 (Patreon)

You may be wondering . . . where's Chapter 3? Well, that is the new chapter that I added just for Kindle! If you want to see what happened before Carlos confronts Jack . . . I would recommend checking it out. 

When I was editing this story for Kindle, I expanded a lot of the Jack and Carlos scenes because I'd forgotten how much I enjoyed their dynamic and I wanted more. I'd love to hear what you guys think of this updated chapter and give this a post a like if you gave it a read :)

The first week of Jack’s holiday passed without incident. He ate gargantuan quantities of the wonderful food, drank copious amounts of alcohol and spent most of his time reading in his garden or drinking in his hot tub.

At the start of the second week, he received a message from the hotel advising him that his boss, Mr Jameson was coming to the hotel for a couple of days and had invited him for dinner.

He’s coming on Wednesday, so I have a couple of days, Jack thought to himself as he tossed the note on the table near the front door.

Jack went to his wardrobe and started rifling through his clothes. Since he’d arrived at the complex, he’d been somewhat reclusive. Part of him was too scared that he’d have another potentially embarrassing incident, so he’d stayed in his villa.

As much as he wanted to swim and visit one of the restaurants, he just couldn’t face the prospect of bursting out of another outfit.

Jack pulled out a pair of navy-blue suit trousers and a white shirt that he could wear with his brown brogues from the flight. Smart, but casual enough for a holiday.

It was only as Jack closed the wardrobe door that he noticed that his stomach seemed to have grown a little in his first week.

I guess I have eaten a lot from room service, he thought as he turned this way and that in the mirror, lifting his t-shirt to assess the damage.

I’ll just try the trousers on to make sure they fit.

Jack yanked down his baggy shorts that he’d lived in since arriving and pulled the navy trousers from the coat hanger. No sooner had Jack stepped into them and pulled them up to his muscular thighs that he encountered a serious problem. They just wouldn’t get up over his voluptuous bubble butt. With much tugging and struggling, Jack managed to get his ample arse covered by the trousers, but no matter how much he breathed in, laid down or struggled, he just couldn’t button them.

What the fuck am I going to do??

Jack pulled off the trousers and hunted through his wardrobe, but aside from chinos that he knew would be just as tight, he didn’t have anything that he could wear that was smart enough for the restaurant that he knew his boss would choose.

After a glass of wine, Jack decided that he’d have to use the 2 days before his boss arrived to work off some of the fat he’d gained. After all, how hard could it be? He didn’t want to risk going to the gym and making a fool of himself, but one of the pools wasn’t far from his villa and swimming would do wonders for flattening his stomach.

That was when Jack faced his next problem . . .

As he rifled through the drawers, the only swimwear he could find was the little red speedo, which he knew would barely cover him. Whenever he’d used the hot tub, he’d been wearing a pair of CK boxer briefs that were now stretched out to the point of being useless.

Jack filled another glass with wine and looked at the clock.

Okay, it’s nearly 7pm. Most people will be on their way to dinner or settling down for the night. If I go now, I should be able to get a good hour’s swim in and it won’t matter what I’m wearing.

Stealing himself, Jack yanked off his Calvin Klein briefs and pulled on the speedo. Getting the speedo over his thighs and butt was difficult enough, but there was so little material that he couldn’t comfortably fit his cock and balls into the pouch. If he got his cock in, one of his balls would flop out of the leg band, but if he got his balls in, his cock would pop out of the waistband.

After much repositioning, Jack started to harden and settled for letting his right ball hang out of the leg band. He pulled up his baggy shorts and grabbed a towel, before pushing his feet into his flip flops and heading to the pool.

The walk to the pool was about 3 minutes and Jack was relieved that he didn’t bump into anyone. When he reached the pool, it was completely empty and not wanting to wait for someone to arrive, he yanked off his t-shirt, shorts and flip flops and jumped into the pool, letting the warm water rush over him.

As Jack swam up and down the pool, the sun started to set, turning the sky a beautiful shade of purple.

‘Excuse me, Mr Matthews.’

Jack stopped in mid-stroke and turned to see the young man from reception stood by the pool.

‘I’m sorry to bother you, sir, but the pool area closed at 7:30. I need to lock the gates up.’

Jack suddenly became very conscious of the fact that under the water, his right ball was hanging out of the speedo and his arse crack was definitely on display.

‘Could you give me ten minutes and come back?’ Jack asked with his best smile.

The young man smiled back. ‘I’m afraid not, Mr Matthews. It’s a health and safety requirement. We wouldn’t want any inebriated guests to wander in here and drown.’

Jack felt the colour drain from his face. Even though the sun was setting, it was still light enough for the young man to see everything.

‘I completely understand, but if you could just give me ten minutes so I can finish my swim, I’ll . . .’

The young man folded his arms. ‘I’m sorry, sir, but you need to get out of the pool now. I would hate to embarrass you by having to call security.’

The thought of more people seeing his predicament made Jack feel sick, so he headed to the small ladder that led out of the pool.

‘Could you possibly turn around?’

The young man frowned. ‘Mr Matthews, are you skinny dipping in one of our pools?’

‘No, no, of course I’m not. It’s just . . .’

‘I don’t know what’s going on here, but I suggest you vacate the pool now or I will call security.’

The young man pulled his phone from his pocket and Jack grabbed the ladder. With a sigh, he grabbed the back of his speedo and pulled as hard as he could to try and at least cover his butt crack.

Hoping it had worked, Jack climbed up the ladder and stepped on to the patio.

‘Mr Matthews, do you think that is appropriate?’

Jack felt the draft before he looked down and saw that where he’d tugged his speedo up at the back, his cock had popped out at the front. Jack immediately tried to shove his now stiffening cock back into his speedo, but the more he manhandled it, the harder he got.

Why now? Why does this keep happening to me?!?

As Jack blushed and babbled an apology, he looked up just in time to see the flash of the young man’s camera.

‘What the hell are you doing?’ Jack stuttered.

‘Let me introduce myself. I’m Carlos Ravenshaw. I believe your boss, Mr Jameson is good friends with my father, George Ravenshaw, the owner of this complex.’

‘Please, I’m sorry, this isn’t my fault. My speedo is too small and I . . .’

‘I don’t care. You’re hot and I’ve been wanting to track you down since you ripped your jeans open in reception when you checked in.’

Carlos’ Spanish accent had now completely vanished, and Jack was in a state of panic.

‘What do you want?’ Jack said as he took in Carlos’ dark hair, dark eyes and tanned, muscular body.

‘I want you to do whatever I want. You may have managed to get away with hiding those ripped jeans from me, but I now have a very incriminating photo of you. If you want me to delete it at the end of your stay, then you’re going to stop hiding in your villa and provide me with some amusement.’

Jack couldn’t believe his ears. His cock was no longer hard, and he took the opportunity to tuck himself in and grab his shorts.

‘Leave the shorts off or this photo goes to your boss with a lovely email about how much you’ve upset the guests at my father’s establishment.’

Jack dropped his shorts and turned to face Carlos with his hands on his hips. ‘Fine, what do I have to do?’

‘Tomorrow morning, I’m running a forest walk and you’ll be coming along.’

Jack shrugged. ‘Fine.’

‘There’s a catch. You’ll have to wear tight trousers of some shape or form, and I’ll have the underwear sent to your room.’

‘What’s wrong with my underwear?’

Carlos just laughed. ‘I’m sure your boxer briefs are just fine but, I have something a little more humiliating in mind.’

‘So, I just have to go on this forest walk?’

Carlos nodded. ‘That’s it for now.’

‘Can I please go back to my room now?’

Carlos laughed again. ‘Not just yet. First off, you can show me how grateful you are that I’m not going to report your indecent exposure to my father.’

Jack wondered what he meant, but as Carlos unzipped the fly of his cream-coloured slacks, Jack knew exactly what he meant.

‘I’m not gay,’ Jack blurted.

It was a blatant lie, but Jack couldn’t risk this guy telling his boss. If Mr Jameson ever found out, then he would lose his job in a heartbeat.

‘Ha! I’m sure. Just suck my cock.’

Jack looked at Carlos’ hard 7-inch cock hanging out of the fly of his trousers and slowly got down on his knees. Without any prompting, Jack took the cock in his mouth and felt his own cock quickly harden and burst out of his speedo.

‘You like that, don’t you?’ Carlos grunted as he grabbed the back of Jack’s head.

Jack had to admit that he did. He couldn’t remember the last time he’d been with a guy. Was it really more than a year? Was it two? The last guy had been his ex and that was . . . far longer than Jack wanted to think about.

As he started to taste the salty pre-cum that was leaking from Carlos’ throbbing cock, Jack couldn’t stop himself from moaning. Carlos’ cock tasted phenomenal and Jack was eager to feel him explode in his mouth.

Carlos gripped Jack’s hair tighter as he started to rock his hips back and forth, taking over some of the work. Jack eagerly took up the new rhythm and relaxed his throat to take as much as he could.

As Carlos growled in his throat, Jack swirled his tongue around the head of his cock and was pleased to feel the muscles in Carlos’ legs tighten.

‘Oh fuck, I’m gonna . . .’

Carlos slammed his cock into the back of Jack’s throat one last time as his whole body tensed and he shot one of the biggest loads of his life. Jack swallowed down every drop greedily and couldn’t stop himself from groping Carlos’ thighs and arse as he did.

‘I think someone enjoyed that,’ Carlos said with a smile as he dragged Jack to his feet. ‘And I’m certain that you’ve done that before.’

Jack tried to ignore the heat in his face as he coughed. ‘I won’t dignify that with a response.’

Carlos just laughed and grabbed hold of Jack’s throbbing hard 8-inch cock. ‘I think you’re lying. Take off your speedo.’

Jack looked around him quickly, expecting to see a full audience. ‘What if someone walks in?’

‘Off!’

Jack grunted as he wrestled the speedo down to his knees, before it dropped to his ankles, and he kicked it off.

‘Here’s the deal,’ Carlos said as he grabbed hold of Jack’s cock again and started jacking him off. ‘I’m going to jerk you off until you cum all over yourself and then you’re going to walk back to your villa with nothing but your key.’

Jack moaned as Carlos tightened his grip and increased the speed. ‘But what if someone sees me?’

‘I reckon you want someone to see you. Just imagine being butt naked and covered in your hot, sticky cum as someone rounds the corner and sees you. You’ll have nowhere to hide as you desperately try to cover your meaty cock with your hands.’

‘Oh, oh, fuck!’

That was all it took as Jack shoot seven thick ropes of cum up and over his chest and stomach. Cum trickled down his body on to his thighs as Carlos pulled his hand away.

‘Enjoy getting back to your villa,’ he said as he grabbed Jack’s clothes and towel and tossed him his key. ‘The walk starts at 10am at the forest entrance near your villa. See you then.’

Jack just stood there in a post-orgasm haze as he watched Carlos walk away with his clothes.

A breeze over his cum covered body made Jack shudder and he clutched the key to his villa tightly in his hand as he realised that he’d have to walk back naked. He wasn’t sure what time it was, but with a deep breath, he opened the gate and briskly walked back to his villa, his cock starting to harden again already.

When Jack got back to the villa, he was fully erect again and couldn’t believe that he’d thought about getting caught. Had he wanted to be caught? He wasn’t sure.

Shaking away the thought, he headed for a shower and washed away the whole evening, praying that Carlos had got what he wanted and would leave him alone. As much as he certainly wouldn’t say not to another round with Carlos, he loved his job and couldn’t stand the thought of losing it. To make matters worse, Jack was becoming more and more confused by his arousal over the embarrassing situations he had started to find himself in. He’d never considered himself to be an exhibitionist before, but maybe he was? Did he want to be exposed?

As he emerged from the shower and pulled on a white cotton robe, there was a knock at the door. Jack pulled it open and was handed a small box by a porter. As soon as he closed the door, Jack tore into the box and pulled out a note.

“Make sure you’re wearing these on the walk. I will check!”

Jack pulled out a pair of black silk bikini briefs, which were exceptionally small, and he was unsure how he would even get them on.

This is going to be some walk . . .