The Trials of Jack Matthews - Chapter 1 (Patreon)

Here's the first chapter in the "The Trials of Jack Matthews" story. This is the updated and revised version that features in my newly published book on Kindle. 

Jack Matthews was based on a guy I used to work with. He was ridiculously attractive, but utterly unaware of how hot he was and I found that such a turn-on that I just had to write a story about him. 

Chapter 1

Jack Matthews needed a break! Being one of the top execs at his Marketing Agency gave him a massive bank balance and a fantastic lifestyle, but he was exhausted and had started making stupid mistakes.

Jack was 36 with a body that came from genetics and a light touch at the gym. His dark hair, blue eyes and strong jaw made him instantly appealing, and he played on his perfect bubble butt in tight trousers to help him seal a deal.

Unfortunately for Jack, he was so overworked that he was turning up to meetings late, forgetting to pick things up from the printers and leaving his house unlocked. Thankfully, a vacation was in sight and Jack had just one more day to get through before he had a blissful two-week break.

Jack had got his assistant to plan his schedule for his last day down to the finest detail. He had meetings back-to-back throughout the day with an hour break to pick his tux up from the drycleaners before heading to the Plaza to change and attend a gala dinner. As soon as the dinner was finished, he’d head home, sleep and then head straight to the airport the following morning.

On his last day, Jack woke up an hour late and raced into the office in a blind panic. In his haste to get ready, Jack wasn’t his usual immaculate self; wearing an older badly fitting suit and some briefs that were so worn and baggy that they weren’t really briefs anymore.  With some creative presentation skills, he managed to get half an hour back, but when the meetings were over, he only had 30 minutes to pick up his tux, get to the Plaza and change before he had to be at the gala dinner. Normally, he would try and sneak in a bit late, but his boss who was also attending the dinner would not accept anything less than him arriving dead on time.

Jack grabbed his briefcase and raced down the stairs to his car before flooring it to the drycleaners.

‘All ready for you, Mr Matthews.’

‘Thank you, Javier. You’re a life saver. You have no idea how much!’

Jack grabbed the suit bag with his tux and the garment bag and bolted for his car. Traffic was a little light and Jack arrived with ten minutes to change.

‘We have a room on the third floor for you to get changed, Mr Matthews,’ the receptionist said with a blushing smile as she handed him a key card.

Jack thanked her and took the card before diving into the lift and running down the corridor to room 352, the room furthest from the lift.

As soon as he got into the room, Jack wiped the sweat from his forehead after tossing everything down on the king size bed. He wasn’t looking forward to wearing his tux. He’d managed to escape most formal occasions for a few months and was disappointed that his boss had forced him in to this one.

Jack stripped naked and tore open the garment bag, pulling out his black patent leather shoes, a black silk cummerbund, socks and garters, cufflinks and a pair of red silk boxers.

If he’d had more time, Jack would have dived in the shower, but that just wasn’t going to be possible. Jack yanked on the red silk boxers and was a little surprised at how tight they were, particularly around his muscular thighs and his bubble butt. He put on the socks and garters before unzipping the bag with his tux and pulling on the white wing collar shirt.

As he buttoned the shirt, Jack had to breathe in and was surprised at how snug it was. He darted over to the full-length mirror, and it was, he realised, the first time he’d looked at himself properly for weeks.

With the heavy workloads, the late nights and the complete lack of time, Jack had completely neglected both the gym and his usual healthy diet. As much as he’d retained the muscles in his arms, thighs and chest, his six pack had disappeared behind a slight belly. This wouldn’t normally be an issue, but his tux had been tailored to him when he was at his fittest.

Trying not to feel too concerned about the slight paunch under his strained shirt, he pulled on the tux trousers with the black satin stripe down the sides and wrestled them up until he could do the button up. The trousers were exceptionally tight, digging into his thighs and waist and crushing his manhood.

After breathing in a number of times, Jack managed to get the cummerbund on, which just about hid how much his trousers dug into his stomach.

Jack tied his bowtie and pulled on his jacket, which was mercifully still a good fit on the shoulders, even if it was a little snug when buttoned. Deciding to go for comfort, Jack slipped his phone and car key into the inside jacket pocket and left the jacket unbuttoned.

With only a minute to spare, Jack threw his clothes and the empty garment bag into the tux bag, zipped it up, grabbed the room key and ran to the lifts to take him back to reception. His run was somewhat restricted due to the tightness of his trousers and by the time, he’d dropped his stuff off at reception and handed back the key, he could feel the sweat on his chest and back.

He mopped his brow with a tissue from the reception desk and entered the ballroom, dead on 7:30.

‘Good to see you on time, Matthews.’

‘Of course, sir,’ Jack said as he shook hands with his boss, Mr Jameson, a man in his late fifties who was well and truly stuck in the 1970’s.

Jack took a glass of champagne and stood with his boss and his wife as they welcomed people to the gala dinner. After half an hour, Mr Jameson released him to go and enjoy the evening and Jack gratefully headed out to the terrace to get some fresh air. He could feel that his tight shirt was glued to his back with sweat and was grateful to be outside.

Jack leaned against the railing as he began to cool off when he felt, more than heard, a slight snap. Realising his right garter had come undone and fallen to his ankle, Jack was about to bend down and fix it when Mr Jameson came outside.

‘We’ll be calling everyone to dinner in a moment and I wondered if you might introduce me so that I can kick off the evening’s festivities?’

Jack forced a smile to his face. ‘Certainly, sir. I’d be delighted.’

‘Good chap. Better head inside.’

Conscious of the sock and garter that was sitting around his ankle, Jack followed Mr Jameson inside as the bell was rung to call everyone to dinner.

Mr Jameson led Jack through the tables to the small stage and asked Jack to stand behind the podium.

‘Once everyone is seated, you can thank them for coming and introduce me.’

Jack nodded and stood behind the podium as Mr Jameson disappeared off to fetch his wife.

With everyone distracted, Jack squatted down to sort out his garter, but as he did so, he heard the unmistakable sound of something ripping. It made his blood run cold as he gingerly felt around the back of his trousers, but he couldn’t feel any holes at all.

‘Thank god for that,’ he whispered to himself as he tried to roll up his trouser leg to re-clip his garter. With the trousers so tight, he could barely roll them higher than mid-calf so had to settle for re-clipping his garter mid-calf, which he knew wouldn’t stay put for long.

Jack stood back up and it was only as he did so, that he realised how much more comfortable he suddenly felt. That was when he noticed that his shirt had split down one of the side seams. No one would be able to see the rip, but it certainly made him a bit more comfortable.

After straightening his jacket, Jack breathed a sigh of relief and rested against the podium.

As soon as everyone was seated, he clapped his hands for silence.

‘Ladies and Gentlemen, we would like to thank you for attending our wonderful event this evening and it gives me great pleasure to introduce to you, the man who made it all possible, Mr Cyril Jameson.’

The room burst into applause and Jack stepped back from the podium as Mr Jameson climbed up on to the stage. As the applause continued, Jack stepped down from the stage and made his way around the top table, to the left, to his seat. He felt his garter fall to his ankle, but was unconcerned as he dropped down into his chair. However, as he did so, there was yet another ripping sound.

Jack subtly checked his shirt but was sure it hadn’t ripped further.

The applause seemed to drown the sound out for the other 4 guests at his table, but Jack was sure that his tight tux trousers must have split. However, without standing up, he couldn’t assess the damage and he didn’t want to draw any attention to, what could potentially be, an embarrassing incident.

Jack applauded with the others as Mr Jameson delivered his speech. The prospect of how badly ruined his trousers might be brought Jack out in another sweat and by the time Mr Jameson took his seat and the starter was served, he was using his napkin to blot the perspiration from his forehead.

‘Thanks for the introduction, Matthews. Good job. I can always rely on you to maintain our company’s exceptional standards.’

Jack dreaded to think what Mr Jameson would think if he found out he’d ripped his tux trousers with some silky red boxers underneath. Mr Jameson was a homophobe, and a dinosaur, and men, in his book, wouldn’t wear such feminine underclothes. Mr Jameson had been known to send men home just for wearing a pink shirt. Red silky boxer shorts were sure to bring Jack trouble if discovered.

The starter and main courses went by with little problem, but Jack avoided most of his main as the waistband of his trousers was digging in more and more uncomfortably to his stomach.

‘God, I’ll be glad to get these off later,’ he thought as he finished his third glass of wine.

‘There’s a wonderful Lemon Soufflé for dessert,’ Mrs Jameson said as she necked her sixth or seventh glass of wine. ‘You’ll adore it, Jack.’

Jack smiled and nodded.

‘And I do hope you’ll join me for a dance after dinner. Cyril never bothers himself with dancing and I do so love to dance.’

‘He’ll be happy to oblige, I’m sure,’ Mr Matheson said with wink in Jack’s direction.

Jack paled as he realised how desperately he needed to check his trousers. He tried sitting up slightly but without rummaging underneath him, there was just no discrete way to do it.

Assessing his surroundings, Jack was relieved that he was sat on the outside of the room and there was a door leading to a service stairwell just a few feet behind him. If he could excuse himself, he could walk backwards and get into the stairwell and to somewhere private to assess the damage. After all, the rip could have sounded far worse than it really was.

Just as dessert was being served, Jack got the perfect opportunity when one of the other guests spilt their wine and everyone jumped back from the table. Jack didn’t waste a second and backed up until he felt the stairwell door behind him. He threw it open and stepped into a mercifully empty corridor.

Breathing a sigh of relief, Jack immediately ran his hands down the back of his tux trousers and was surprised that they were perfectly intact. Confused, he looked down and tried to see where the rip had come from. His shirt hadn’t ripped any further, his jacket felt like it was still in one piece and his trousers seemed to be fine.

It was just as Jack put his right leg forward to head back into the ballroom that he felt something amiss. He put his hand in his pocket and with a bit of feeling around in the constricted space, he realised that the seam down his outer thigh had split from just below the waistband to mid-way down his thigh, but by some miracle the satin stripe down the side of his trousers had stayed together and was doing an excellent job of hiding the rip.

‘Thank God for that,’ Jack said with a sigh of relief and feeling much more relaxed, he slipped back to his seat without even being noticed.

The Lemon Soufflé was served and coffee followed quickly afterwards. Jack was still feeling incredibly uncomfortable in his tight trousers, but he was so relieved that his trousers weren’t visibly ripped that he was happy to put up with it.

‘Oh, Jack, it’s nearly time for a dance,’ Mrs Jameson said with a tipsy grin as the waiters flocked to the table to clear away the coffee cups.

Jack just smiled and took another sip of wine. He was hoping that he’d be able to sneak away as soon as he’d done his dance with Mrs Jameson. Mr Jameson was already nicely tipsy so Jack hoped he wouldn’t notice.

The dancefloor was in front of the stage surrounded by the tables. As soon as the last of the dinner things had been cleared, a band took to the stage and the lights dimmed slightly. A few people immediately took to the floor and Mrs Jameson quickly got to her feet.

‘Come on, Jack – time for a dance.’

Jack stood up and followed her on to the dance floor as Mr Jameson necked another glass of whisky. As Jack followed Mrs Jameson, he wove between the chairs of the table next to them and felt something tug on his trousers. He quickly turned around to see that they’d snagged on the sequins of a woman’s jacket that was over the back of her chair.

As he stepped on to the dancefloor, Jack discreetly ran his hand over his firm bubble butt, but the only thing amiss was a loose thread.

‘Another lucky escape,’ he whispered to himself as he took Mrs Jameson by the hand and hip and started to dance with her.

As the band increased the tempo and moved on to a new song, Jack felt his garter slip down to his ankle once again. Not wanting to tempt fate with his precarious outfit, he left the garter and sock to roll down over the heel of his patent leather dress shoe and opted to step only on the ball of his foot instead of the heel.

Mrs Jameson had become utterly engrossed in the dance and was twirling merrily around Jack as he steered her around the floor. Her exuberance made Jack stumble slightly and his right foot slipped out where his sock was now wrapped around the heel of his shoe. He managed to regain his balance without falling, but it caused Mrs Jameson to fall against his back as he’d been in the middle of spinning her around him.

‘I think it’s time for a breather,’ she said with a gasp. ‘Thank you, Jack.’

Jack smiled and politely nodded as she moved away from the dancefloor. With Mrs Jameson gone, Jack quickly inspected the loose thread at the rear of his trousers and was surprised to find that it was longer than before. The seam was mercifully intact, but he yanked the thread off just to be sure it didn’t get caught and get even longer.

‘Time to get out of here before my luck runs out,’ Jack thought to himself.

Without even thinking, Jack stepped forward on to his right foot, which skidded on the polished wooden floor with his sock and garter still wrapped around the heel. He managed to remain standing, but not before his leg slid sharply forward and he felt a definite loosening in the crotch area of his trousers.

Not wanting to draw any attention to himself, Jack quickly headed for the nearest door, which was the one that led to the service stairwell. He was glad that no one stopped him, and he quickly threw open the door and slammed it shut behind him. His hands flew to his crotch and felt a hole from the bottom of his fly that ran about four inches to the rear seam.

‘Okay, I need to get my stuff and go!’

Jack gingerly leaned forward and managed to get his sock and garter back to halfway up his calf before he opened the door and stepped out quickly, letting the door close against his back so that it looked like he’d been stood there the whole time.

Comfortable that no one had seen him, Jack decided to walk around the outside of the ballroom to the entrance. That way no one should notice him sneaking out. Jack was just about to head off when he noticed Mr Jameson returning to his seat from the bar.

‘If he sees me, he’ll wave me over,’ Jack thought with a panic. ‘I better be quick.’

Jack made a quick walk to his left away from Mr Jameson, but when he’d gone no more than about 3 feet, his heart sank as he felt a familiar tugging at his rear. Jack glanced behind him and saw the loose thread from his trousers pulled taught where it was trapped in the door behind him.

After a quick check in Mr Jameson’s direction, he grabbed the thread and yanked it away from the door, but instead of coming free from the door or snapping where it was pulled taught, he felt another hard tug before the tight tux trousers suddenly felt much looser where they’d previously felt glued to his ample bubble butt.

Jack tried to do his utmost not to panic, but with a brief feel of his butt, he only felt split trousers and his silk clad cheeks.

Deciding to pray that no one would see him, he kept his back to the wall and did a quick sidestep around the outside of the room. Just as he reached the double doors, he was relieved that no one was loitering in the hallway, and he ducked around the doors and out of the ballroom.

As Jack dashed down the corridor, he felt his garter once more slip down to his ankle, but he ignored it as he was now safely on carpeted floor and less likely to slip.

‘Can I grab my things? Jack Matthews,’ Jack said as he got to reception and prayed that they wouldn’t realise his predicament.

The young man looked confused. ‘We don’t have anything behind here for you, Mr Matthews. I believe your things were sent over to your house, as you requested.’

Jack could have kicked himself. He remembered making that exact request when he’d asked for a room to change. He didn’t want to risk getting drunk and leaving his stuff behind.

‘Ah yes, thank you. Good evening.’

Jack tried to do his most subtle walk towards the revolving door, praying that the young man on reception wouldn’t notice his silk clad bubble butt peeking out of the huge rip in his trousers.

As he stepped into the revolving door, he couldn’t believe his luck when he saw Mrs Jameson descending the stairs to the car park in front of him, talking to another woman. Jack stepped out of the door and noticed a narrow path to his right that led around the side of the building. It was away from the car park, but it was also away from Mrs Jameson.

The path circled the main hotel building and was flanked on both sides by waist high hedges.

‘Where the hell does this lead?’ Jack muttered to himself as he tried to hold his ripped trousers closed over his ample bubble butt.

As Jack continued to walk around the building, he started to hear voices and as he turned a corner, his jaw dropped when he realised that the path led around to the terrace behind the ballroom.

Hoping that Mrs Jameson had gone back inside, Jack turned around and headed back towards the main entrance and the car park. Even though the car park was just on the other side of the thick hedge, there was no path through, and he didn’t want to risk his tux further by jumping over it or attempting to wade through it.

As Jack rounded the last corner, feeling more pumped on adrenaline than he could ever remember, he couldn’t believe how bad his luck was. Coming towards him were Mrs Jameson and the woman from before.

Jack stepped back around the corner, and with a heavy sigh, he knew he had no choice other than to go through the hedge, as he realised, he wouldn’t be able to jump over it without some sort of assistance.

Not wanting to waste any time, Jack found a section of the hedge that seemed to be a little less dense and started to push through it, but the branches were so tangled that there was just no way to get through it, but under the light of one of the lamps, he saw that there was probably enough space to crawl underneath.

With the sound of Mrs Jameson’s drunken tones getting louder, Jack dropped to his knees and tried to ignore the slight rip that met his ears. He leaned forward and with as much as strength as he had, he started to crawl through the small gap. The hedge scratched his back mercilessly, but he soon had his upper body on the side of the car park.

Hearing Mrs Jameson’s voice as if he was stood next to her, he yanked himself through the hedge, praying that the hushed rip wasn’t too much damage. But as he tried to yank his feet through, his sock and garter that were caught around his heel tangled in the hedge and his shoe came clean off of his foot.

‘I suppose we’ll be here until the end,’ Mrs Jameson said as she rounded the corner.

Jack stayed as still as possible and prayed that his shoe was out of sight. His heart hammered in his chest as he listened to Mrs Jameson and her friend as they walked past. The adrenaline was taking over, and Jack noticed that despite his terror at getting caught, he was starting to get aroused, and his cock was hardening quickly in the tight confines of his silk boxers.

When Mrs Jameson’s voice had eventually faded away, Jack got to his hands and knees. But he was stunned to see his trousers fall away from his body and he looked behind him to see that his trousers had shredded straight up to the waistband.

Feeling frustrated and annoyed at the predicament he found himself in, Jack tore the tattered remains of his trousers from his legs before reaching through the hedge to retrieve his garter, sock, and shoe. As he bent down to put them back on, his cummerbund popped loose and dropped to the ground. Jack kicked it into the hedge with the remnants of his trousers. Stood with nothing below the waist except his tight silk boxer shorts, his garters, socks and shoes, Jack straightened his jacket.

Not wanting to risk getting caught with no trousers on in the car park, Jack walked quickly towards his car, praying that no one would see him. But, just as he crossed into the next row of cars, he heard the unmistakable CLICK of someone electronically unlocking their car, accompanied by the flash of lights.

Jack quickly squatted to the ground, but as soon as he did so, there was an almighty RRRRRRIIIPPPPP and his skin-tight silk boxers ripped from the waistband, down the rear seam and up the button fly to the waistband. Jack’s semi-erect cock burst free from its silk prison and quickly started to harden to its full eight inches.

Embarrassed by his state of undress and arousal, Jack blushed as he heard footsteps approaching a car a short distance away. The door opened and closed, the engine started, and the car pulled away.

Jack jumped to his feet and ran the rest of the way to his car, his garters sliding down his muscled calves to his ankles and his cock slapping against his leg and stomach.

By the time he reached the car, his cock was throbbing at full mast. He grabbed his shaft and tried to wrestle his dick back inside the ripped silk, but the only thing he achieved was a string of precum that coated his fingers.

It was at this moment of heightened arousal that Jack’s cock completely took over his brain. He glanced around, and being fairly certain that he was alone, he gripped the front of his shirt and ripped it wide open, exposing his slightly furry pecs.

Jack ran a hand down his stomach to his glistening cock before wrapping a hard around the length and starting to stroke back and forth. A moan slipped out as his fingers connected with his overly sensitive head.

I can’t believe I’m doing this! What if I get caught? I’m practically naked.

Jack increased the speed on his dick, his free hand teasing his nipples as his bubble butt clenched with each thrust.

Within a matter of seconds, Jack was past the point of no return, and he grunted loudly as he shot his load over the side of his car. Cum coated his cock, his legs, and his shoes, but Jack could barely stand, let alone care.

‘Oh, that was so . . . wow.’

As soon as the orgasm subsided, Jack came back to reality with a crash. He looked down at his naked body, except for a bowtie, socks and garters around his ankles and patent leather dress shoes.

‘What the fuck is wrong with me!’

Jack dived into the driver’s seat, slammed the door and accelerated out of the car park, praying that the CCTV hadn’t caught him and that he wouldn’t get pulled over on his way home.