The Trials of Jack Matthews - Chapter 2 (Patreon)

Here's chapter 2 of the Jack story. It's been so great to see people downloading this on Kindle and enjoying the changes. This airplane scenario is actually based on a fairly real life event - let me know if you want to hear more and I might do a separate post ;) 

Jack Matthews woke up to the sound of his alarm and was more than relieved that he would be getting up to head to the airport.

The previous night, Jack had experienced both the most disastrous evening of his life as his tuxedo had nearly fallen apart, but equally one of the best orgasms he’d ever had in his ripped boxers in the middle of the car park. He still couldn’t believe he’d jerked off in that state so close to so many people he worked with. But the memory was clearly having an effect as his cock throbbed looking for attention.

‘Nope. I need to get ready,’ he said as he climbed out of bed and turned on the shower to a colder than normal temperature.

Jack had bought the clothes for his holiday a few weeks before and had everything ready to go by the front door. With his hectic work schedule, he knew he wouldn’t find time to pack, so he’d done it in advance.

Having spent so much time at the office in recent weeks, Jack didn’t have a great deal of clean clothes to wear for the flight, but he found a pale blue shirt that was on the snug side, a pair of old jeans that had seen better days and a pair of black mesh briefs. He finished the outfit with a pair of brown leather brogues.

When he looked in the mirror, Jack couldn’t help but notice how his body had changed over the last few weeks and he hadn’t even realised. His flat, toned stomach was now a paunch and his jeans and shirt clung to his body, outlining the muscle in his thighs, and making his ample bubble butt look even bigger than it usually did.

Jack called for a taxi and waited by the door with his case as he fired off a few last emails on his phone.

‘Heathrow Airport, please,’ Jack said as he opened the door of the cab and tossed his case on to the seat.

He dropped down in the seat next to it and realised that one of the buttons had come undone on his shirt. Sighing, he discreetly did it up and returned to his emails as the taxi carried him to the airport.

The dull process of checking in and going through security was as uneventful as it could be and before long, Jack was sat in Departures taking calls and doing emails. Jack opted to stand up as he knew he’d be sat for several hours on the plane ride.

When the gate opened, Jack queued with the others and quickly stowed his carry on and took his seat. He was relieved that the flight seemed to be fairly empty, and no one was sat on either of the seats next to his window seat.

By the time the other passengers were settled, and the plane started to taxi to the runway, Jack shifted uncomfortably in his seat. Since he’d left the house, he’d barely sat down except for the taxi ride, but now that he was seated properly, without any distractions, he realised how uncomfortable the mesh briefs were that he’d stupidly thrown on.

The thin net of the mesh dug uncomfortably into his ample butt cheeks, whilst also pulling tightly on his manhood. Jack shifted back and forth in his seat, but no matter what position he tried, he couldn’t get comfortable.

By the time, the plane had taken off and levelled out, Jack jumped out of his seat and headed for the restroom.

I’ll just take them off and go commando, he thought to himself as he walked down the aisle. At least I’ll be comfortable then.

Jack stepped into the rest room and locked the door behind him. His hands flew to the button and fly on his jeans and in no time, he’d got his jeans to his ankles, before kicking them off.

Jack looked down at the mesh briefs and hadn’t realised before how tight they were on him. As he peeled them off and down, they left an imprint in his skin where they’d dug into his flesh so much.

Breathing a sigh of relief, Jack stepped back into his jeans and pulled them back up before tucking himself in and breathing in to button them. Jack balled up the mesh briefs and put them in his pocket so that he could discreetly put them into his carry-on bag later on. The only slight problem was that Jack’s jeans were so tight that he didn’t have much pocket space to hold a balled-up pair of briefs, so they stuck out of the top of his pocket slightly, but he hoped, not noticeably.

As Jack headed back to his seat, his briefs were pushed out of his pocket by the pressure of his thigh moving back and forth. The briefs dropped to the floor and feeling the change in his jeans, Jack turned around and quickly bent down to retrieve them before anyone noticed.

However, as he did so, two things happened – two buttons burst off of his shirt and there was a muted popping sound that came from his crotch.

Ignoring what could have happened to his clothes, Jack grabbed the briefs and dived back into his seat. As he sat down, he discreetly felt the crotch of his jeans and realised that there was small hole the size of his thumb nail. When he looked at his shirt, he realised that they’d come off of the top of his shirt where it was so tight over his chest. Thankfully, it looked like he just hadn’t buttoned them and was flashing a little bit of chest.

Okay, Jack thought, this isn’t bad. It’s not like the gala dinner. I don’t have to move from this seat and the hole in the jeans is too tiny to worry about. I’m fine.

The rest of the flight passed uneventfully. Jack was slightly worried about being commando in a pair of jeans with a rip, but before long, he started to relax and as the plane came in to land, he’d forgotten about it.

When the plane had arrived at the terminal, Jack unclipped his seat belt, jumped up from his seat and grabbed his bag before following the other passengers, unaware that he’d never bothered to put his mesh briefs in his bag and had left them on the seat.

There was a long queue to get through security and the temperature in the airport was stifling. Jack hadn’t realised how humid it would be and was hoping it was just the airport. When he eventually reached baggage claim, his suitcase was already circling the carousel, so he grabbed it and headed outside, almost relieved that his shirt buttons had popped off so that he could get a bit more air to his skin.

When he stepped outside into the Spanish heat, he was relieved that the humidity seemed to be from the airport and not the country. It was hot outside, but there was a warm breeze.

Jack was staying in a high-priced resort about an hour from the airport. The resort was a villa complex that boosted privacy and luxury. Each villa was isolated with its own private garden and hot tub, whilst providing a range of decadent restaurants and relaxing pools and spas.

After flagging down a taxi, Jack gratefully handed his luggage over to the driver, whilst he slipped into the rear seat and breathed a sigh of relief that he was nearly at his destination. It was only as he got comfortable that he realised that he’d left his mesh briefs on his airplane seat, but deciding that they wouldn’t be missed, he rested his head back and let the warm breeze relax him as the taxi pulled away.

The drive was as uneventful as most of the flight and in no time at all, Jack was standing with his luggage in the luxurious atrium of the resort reception area.

‘Jack Matthews, checking in,’ he told the ridiculously handsome man behind the highly polished desk.

‘A pleasure to meet you, Mr Matthews. Mr Jameson told us that you were coming,’ the man said with a heavy Spanish accent. ‘Do you have your passport?’

Jack was hypnotised by the beautiful dark eyes, the chiselled jaw, and the broad shoulders of the guy across from him.

‘I’m sorry. What did you say?’

The man chuckled and the rumble of it made Jack shiver.

‘Your passport please, Mr Matthews.’

‘Ah, yes, it’s here somewhere,’ Jack said with a frown as he rifled through his carryon bag that hung over his shoulder, but after much opening and closing, he remembered that he’d tucked it into the front pouch of his suitcase.

‘Just a second,’ he said with an apologetic smile.

Jack squatted down to face his suitcase and heard the unmistakable and somewhat familiar RRRRRIIIPPPP that indicated that his tight jeans had given up against the strain.

‘’Is everything alright, sir?’

Jack jumped up and sheepishly handed over his passport, praying that the damage to his jeans wasn’t too severe or obvious.

As the young man called for the porter, Jack spun around so that his back was to the chest height desk.

‘Thank you,’ Jack said with a smile to the porter who happily took his carryon bag and his suitcase.

With the porter gone and an empty room in front of him, Jack turned back to the hunky receptionist and smiled like everything was perfectly fine. Except for the fact that he’d just ripped his tight jeans, whilst he was commando, in the resort that his boss frequented on a quarterly basis. To make matters worse, memories of the gala were fresh in Jack’s mind and the sound of the rip was making his cock harden.

‘Your villa is one of our best, sir,’ the sexy Spanish guy said as he held out a beautifully printed map. ‘You are in villa 55 on the outskirts of the complex with your own terrace, gardens and hot tub. It backs on to our wonderful forest, so it is perfect if you wish to take long walks.’

‘Thank you,’ Jack said as he scribbled his signature on the reservations form that was presented to him.

The receptionist handed him a key attached to an engraved plaque of wood that bore the number “55”.

‘Would you like someone to show you the way?’

‘No!’ Jack barked at him. ‘I mean, thank you, but I can find my way.’

The handsome receptionist smiled and nodded. ‘Very well, sir. However, please let us know if there is anything at all we can do for you.’

Jack forced a smile to his face as he realised that he’d have to escape the atrium without the receptionist seeing the back of the jeans.

‘Thanks for your help,’ Jack said again. ‘But can I just ask . . . can you . . . ummm . . . point me in the direction of the Laguna Restaurant? Just so that I know for tonight.’

The receptionist came out from behind the desk and Jack turned so that he was constantly facing him. The guy had an incredible chest, and muscular legs that were highlighted by his tan slacks.

Jack followed him to a door that led out on to a wide terrace with wicker chairs and small tables.

‘The Laguna is down that path ahead and to the right.’ The guy placed his hand on Jack’s back and turned him slightly in the other direction. ‘Your villa is down the left path here. Follow it down and through the gardens and your villa is the one on the edge of the forest.’

Jack stepped back abruptly so that his firm bubble butt was pressed against the door and thanked the receptionist who opened his mouth, changed his mind, and then headed inside.

Jack pretended to busy himself looking at his phone until the receptionist was back behind the desk. Aside from wanting to keep his ripped jeans hidden, the guy was making Jack’s brain short circuit. Once he could escape without being seen, Jack pocketed his phone and headed across the terrace and down a short flight of steps to the pathway that led to his villa.

I can’t believe I’ve ripped these damn jeans. Mr Jameson recommended this villa and if I show him up, he’ll kill me. I just need to get to my villa, and I’ll be fine.

Jack walked as quickly as he could without looking too suspicious. He was doing his best to look natural whilst using his right hand to hold the torn denim together over his bubble butt – to little avail given the size of the massive rip that ran from waistband to crotch.

As Jack rounded the corner and passed another villa, he heard voices up ahead and dodged down a path to his right. The path clearly led to someone else’s villa, but he couldn’t see anyone, so he backed around a corner and ducked down behind a huge plant covered in bright pink flowers.

As he ducked down, Jack felt the rip spread down his right thigh at the back and realised that his jeans had ripped next to the seam, instead of the seam itself.

Oh god, this could get really bad.

Despite his angst at getting caught, he couldn’t ignore the fact that his cock was now fully erect and causing a damp patch on the front of the faded denim.

When the voices had passed, Jack jumped up from his spot and continued on to his villa. He managed to pass another 5 villas, before he turned a corner and saw his villa. It was nestled against the edge of the forest and was surrounded by luscious plants and a manicured lawn.

Confident that he could now run, Jack picked up his pace to a jog until he got to the end of the path that led to the front door, by which time, the rip had spread down his right thigh to his knee so that his bare muscled leg was on show.

As Jack turned on to the path to head to the front door, the door started to open and Jack immediately retreated and dashed into the forest, where he squatted down again – ignoring the loud RRRRRIIIIPPPPPP as the crotch tore open on his jeans – and watched as the porter emerged from his villa and locked the door.

Whilst Jack watched the porter lock up and leave, his hand ran down his chest to the destroyed crotch of his jeans where his fingers brushed the damp head of his throbbing cock.

Not again, Jack thought to himself as he gripped his cock in his hand.

Jack stood up and took a step backwards, his hand still glued to his erection. He knew he had to get inside his villa, but the thought of another open-air jack off session was too hot to resist.

It’ll only take a matter of seconds. No one will see me.

Jack’s hand started to slowly move up and down his hot shaft as he bit his lip to stop himself from moaning.

It was then that he saw the porter returning to his villa and he quickly dropped to his knees to avoid being seen. However, that was all it took for his jeans to completely give up and the waistband ripped open leaving his jeans to drop to his knees, exposing his firm bubble butt and his muscled thighs.

No, no, no, no, no!!! I can’t get caught like this.

The porter came out of the villa with a frown on his face, before locking up again and heading away. Jack stood up and tried to pull his jeans together, but his hands connected with his cock rather than the waistband and he couldn’t fight back the moan that escaped his lips.

I can’t do this again . . . can I?

Jack gripped the shaft of his dick and the sight of his exposed lower body, and the outside setting brought back the memory of the night before.

Before he could question whether there were cameras or if there was someone in the vicinity, Jack started to stroke his dick as fast as he could. He wanted to cum so bad. The thought of being commando on the plane, his jeans ripping in reception, the sexy receptionist . . . it was all too much. Jack groaned as he came all over himself, panting for breath.

Coming to his senses, Jack held up his jeans, grabbed the key and ran to the door, before unlocking it and slamming it behind him.

Once he’d got his breath back, Jack kicked off his shoes and the remnants of his jeans, before cleaning himself up with a towel and throwing on a white cotton robe. He cleaned up the mess he’d made in the hall before setting to the task of unpacking his case that had been laid out by the porter in the walk-in wardrobe.

Oh no!

As Jack rifled through his suitcase, he couldn’t believe how stupid he’d been. Not only had he bought the clothes several weeks before in his usual size AKA the size he was before he’d gained a little weight, but some of the clothes were a size smaller as Jack had convinced himself when he’d bought them that he’d have plenty of time to shape up his beach body in preparation for his vacation.

This is going to be a seriously interesting vacation, he thought as he held up a tiny red speedo.