The Trials of Jack Matthews - Chapter 5 (Patreon)

When I was editing this for the Kindle edition, I really wanted to amend this chapter to focus on more on the chemistry between Carlos and Jack, rather than Jack just having another wardrobe malfunction. I'd love to hear what you guys think of the revised chapter! 

When Jack woke the next day, the first thing he saw was the pair of black silk bikini briefs on the nightstand.

Oh god – the forest walk!

Jack dragged himself out of bed and after a mug of coffee, he hit the shower before returning to his room to get dressed. After a quick check of the time, he realised that he only had 5 minutes before he had to be outside. He certainly didn’t want to make matters worse for himself with Carlos by being late.

Jack grabbed the pair of bikini briefs and after much struggling, pulled them up. In the few steps over to the mirror, the silk had ridden up his massive butt and was sliding between his cheeks making his cock twitch.

As he looked in the mirror, Jack couldn’t help but gasp at the sight that met him. The bikini briefs barely contained his ample cock and balls at the front causing the small piece of silk to dip down at the front and display his trimmed pubes. From the back, it was even worse. The black silk barely covered his arse at all and with the few steps he’d walked, they’d ridden up so much that they looked like a thong.

Knowing that he had no choice but to wear them, Jack opened his wardrobe and pulled out the tan chinos and a navy-blue t-shirt. He didn’t need to pick something tight on purpose as he knew that anything in the wardrobe was tight on him thanks to his weight gain.

After much wrestling around on the bed, Jack managed to get the chinos on and buttoned, but to say they were strained was a vast understatement. The seams were pushed to the limit, Jack’s bulge looked obscene being outlined so clearly in the tan material and the chinos didn’t quite cover the crack of his huge backside.

Unable to do much to hide his exposure below the waist due to the short t-shirt he was wearing, Jack pushed his socked feet into a pair of trainers, grabbed his key and headed out of the door.

Jack walked over to the forest entrance with a bit of difficulty. The chinos were so tight that they completely restricted his legs from moving, whilst the bikini briefs had ridden up his crack again and the constant sliding of the silk was making him semi erect.

Carlos was waiting for him and grinned when he saw how tight Jack’s trousers were. ‘Glad you could make it, Mr Matthews. We’re just waiting for a few more guests.’

Jack stood next to Carlos with his back to the forest, hoping that no one would see his butt crack hanging out. He tried repeatedly to yank the chinos up, but there just wasn’t enough material.

As they stood and waited, Carlos talked about the route they’d be taking whilst rubbing his hand across Jack’s bubble butt, occasionally running his finger into the crevice between his massive cheeks.

‘I guess those undies were too small. I would never have guessed it.’

‘You knew full well that they’d be too small,’ Jack said through gritted teeth.

Before Carlos could respond, 4 men came down the path. All of them were in their late fifties and early sixties and were dressed in cargo shorts, t-shirts and walking boots.

‘Nice to see you, gentlemen,’ Carlos said as he shook their hands. ‘Let’s get going.’

Jack waited for the men to walk past him so that he could follow at the back. As they wound their way through the narrow forest trail, Jack’s t-shirt was soon damp with sweat. When he’d seen the 4 men, he’d assumed that they would be taking a leisurely pace, but he couldn’t have been more wrong. They were speeding along, and Jack was struggling to keep up with his restricted movement.

‘How’s it going?’ Carlos said as he let the men go ahead and dropped back to walk next to Jack.

‘Fine thanks,’ Jack said as he wiped the sweat from his forehead.

‘You look a little flustered,’ Carlos said as he placed his hand on Jack’s butt and gave it a squeeze.

‘I’d be fine if I was in a shorts like the rest of you.’

Jack felt as pissed off as he sounded. It was bad enough that Carlos was effectively blackmailing him, but having to do a walk in the Spanish heat in a skin-tight pair of chinos was like torture. And to make matters worse, the silk bikini briefs were sliding over his balls and between his cheeks, which was keeping his cock semi-hard the entire time.

‘Maybe you should take your trousers off if you’re too hot?’

‘Oh, what a genius idea,’ Jack said in his iciest tone.

‘You might want to remember what I have on you before you start on the sarcasm. Or would you like to lose your job?’

‘How could I forget? Just get this walk over already.’

Carlos laughed. ‘We’ll play it that way then.’

Carlos jogged ahead to the men and brought them to a halt. ‘I think we’ll take a slightly different route today. Are you guys up for a route that’s a little more energetic?’

The men all happily agreed, and Carlos gave Jack a dirty look before turning to the left and leading the group down a much narrower path that was on a steady incline.

As the walk continued, the incline got steeper, and Jack was finding it more and more difficult to keep up. His trousers were so tight that walking on flat ground was hard, but uphill was nearly impossible as he just couldn’t spread his legs enough.

As they rounded another bend, the gradient got even more severe, and Jack lifted his right leg to step up on to a ridge. As he did so, there was loud rip, and his chinos tore open from the knee to the crotch along the inner seam.

Carlos suddenly appeared with a huge grin on his face. ‘Oh dear, have you ripped your trousers?’

Jack just rolled his eyes as he tried to pull the material closed with little success, his muscular thigh on show through the rip.

‘Let’s hope you can keep up with the rest of the walk,’ Carlos said as he gave Jack another slap on the arse.

Carlos jogged ahead and Jack followed, relieved that he could at least move more freely. Granted, he was now considering what Carlos would do with him now that his trousers had ripped, but he’d be lying if he said that they were negative thoughts.

After all, Carlos particularly sexy in his white shorts as he led the group. His arse was packed into them, and it was almost hypnotic to follow.

Jack shook his head and tried to block those thoughts before his dick got to full mast.

Jack managed to just about keep up with the group as they reached the top of the incline and came to a stop for photos of the view.

Jack stayed behind the group with his legs clamped shut to try and hide his predicament, whilst keeping his hands casually in front of the obvious bulge in his trousers.

‘Okay, it’s a simple route back now,’ Carlos said to them. ‘We just duck under this fence and then head straight down the path to the complex, so head back when you’re ready.’

Jack breathed a sigh of relief as the 4 men instantly headed for the fence with talks of getting back for a drink before lunch.

‘After you, Mr Matthews,’ Carlos said with an expectant smile.

The fence was about chest height, but Jack guessed he’d have to pretty much double over to be able to fit underneath and through the gap.

Jack was desperate to get back to his villa so he could get naked and jerk-off. The sun was scorching, and he was sweaty and horny. He approached the fence and bent over so that he could step underneath, but Carlos suddenly stopped him.

‘Now I think about it, I think you could probably do with an outfit change before we head back.’

Jack raised his eyebrows in question as Carlos closed the distance between them. His lips were just inches from Jack’s and Jack couldn’t help but lean forward slightly. As much as he didn’t appreciate the blackmail, he couldn’t deny his attraction to Carlos.

‘Do you want something?’ Carlos asked with a grin as he closed the distance a little more.

“I . . .’ Jack couldn’t finish his sentence because Carlos put a hand over his mouth.

‘Like I said, you need an outfit adjustment.’

Carlos undid the waistband on Jack’s chinos and the sound of the zipper being pulled down sent shivers through Jack.

‘Get them off,’ Carlos said, his lips against Jack’s ear.

Jack kicked off his trainers and yanked the chinos down, not caring that they ripped even more as he did so. Once they were off, he pushed his feet back into his trainers.

Carlos ran his hands down Jack’s back to his arse and Jack was surprised when Carlos groped his bare cheeks. The silk briefs had ridden up so much that they were wedged between his cheeks, not to mention the now throbbing tent in the front.

Carlos tossed the trousers into a clump of trees and ducked under the fence.

‘I suggest you walk back to your villa before someone sees you.’

Jack’s cock throbbed and he felt a dribble of pre-cum leak into the slinky silk.

‘Although, I think you want someone to see you,’ Carlos said with a shrug.

‘No, I don’t. I want to get back to my villa and pretend this never happened.’

Carlos laughed and stepped in front of Jack. ‘Then we’d better make things better for you.’

Carlos grabbed the front of Jack’s t-shirt and tore it from his body with a loud rip.

Jack’s cock twitched in the bikini briefs and the damp spot spread. ‘Carlos, stop! What the fuck am I supposed to do now?’

Carlos tossed the t-shirt behind him. ‘How humiliating for you. Stranded in the forest in just your trainers and a slutty pair of bikini briefs that don’t even fit you.’

Carlos ran his fingers over Jack’s nipples making him moan loudly.

‘Carlos, please. What if someone comes?’

‘Oh, someone is going to cum,’ Carlos said with a chuckle as he grabbed a hold of Jack’s silk clad cock. ‘Looks like you’re a bit wet.’

Jack had never been so conflicted in life. He was totally exposed in public, but he was so horny and desperate that he didn’t know what to do with himself.

‘Carlos, let’s just go back to my villa. I don’t want to get caught.’

Carlos took his hands away from Jack and raised an eyebrow. ‘What happened to not being gay?’

Jack blushed as Carlos chuckled. ‘A straight boy wouldn’t suck cock the way you did. Not to mention the way you react every time I touch you.’

Jack opened his mouth to deny that, but he couldn’t get the words out.

‘Now, we’re going to walk back to your villa and when we reach the forest entrance, you’re going to get down on the path and jerk off whilst I watch. Now, get moving.’

Jack protested the whole way down the path as he kept his hands tightly over his cock, praying that he could convince Carlos to change his mind. Carlos ignored Jack completely and aside from the odd occasion where he’d grope Jack, he didn’t talk to him at all.

When they neared the forest entrance, Jack stopped dead in his tracks.

‘I didn’t tell you to stop,’ Carlos said to him.

‘What if there’s someone out there?’

Carlos stepped up behind Jack and placed his hands on Jack’s biceps, before grinding his crotch against Jack’s bubble butt. Carlos put his lips against Jack’s ear. ‘I hope there is someone out there to watch you on your knees jerking that big dick. Now get to it or I’ll make your next task even more public.’

‘I’ll do it, I’ll do it,’ Jack said breathlessly, as he tried to block out the thoughts of Carlos fucking him right there and then.

‘Now go to the entrance, remove the undies, get down on your knees and jerk off until you cum.’

Jack took a deep breath and tentatively headed towards the forest entrance, relieved that he couldn’t hear any voices.

As Jack emerged from the trees and the sunshine hit him, he suddenly realised how much trouble he could be in. What if someone did see him? What if he got arrested?

‘I didn’t think you’d want to take your time,’ Carlos laughed behind him.

Jack gripped the waistband of the bikini briefs and with some difficulty, he dragged them to his ankles and kicked them away, letting his cock throb at its full eight inches.

Jack dropped to his knees on the dusty ground and immediately grabbed his cock in both hands.

‘Better be quick, Jack,’ Carlos said from somewhere behind him.

Jack didn’t need much more encouragement and his hand gripped his dick more tightly, pre-cum running over his fingers as he tensed his thighs and groaned through his bared teeth.

As Jack started to jerk-off, he was completely unaware of Carlos rubbing his cock through his shorts behind him. The sight of Jack naked and on his knees, exposed to the world, was too much for Carlos and as Jack moaned, Carlos felt his cock shoot inside his undies.

‘Ah fuck,’ Jack hissed through his teeth as thick ropes of cum shot all over his chest and stomach.

Jack panted for breath, his pupils blown, and his entire body tensed.

Carlos appeared at Jack’s side as he got to his feet. ‘Looks like someone enjoyed that.’

‘Yes, I . . . no . . .’ Jack muttered.

Carlos laughed and the sound made Jack’s dick twitch. ‘You better get that sexy arse inside and I’ll send you further instructions.’

Carlos closed the gap between them, their lips so close to touching that Jack had to stifle a moan of desperation. How could he want someone who was tormenting him so much?

Carlos ran a finger down Jack’s cum covered chest and pushed it into Jack’s mouth, forcing him to clean up his own cum. ‘Laters, Matthews.’

And with that, Carlos walked away, leaving Jack to run back inside his villa, totally confused about what he’d just done, what he wanted and why.

It was later that day that a letter appeared under his door.

“Your boss arrives tomorrow afternoon and wants to see you for dinner. My father and I will be joining you as I’ve told Mr Jameson what mates we’ve become. I suggest you make sure you have something decent to wear. I don’t want to be shown up! However, I expect you to be commando. See you at 7pm!”