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JockMailed - Chapter 6
🕑 Added 2025-10-13 08:00:06 +0000 UTCHere's the next amended chapter of JockMailed - I hope you guys enjoy this one, and the JockMailed conclusion will be posted next month!
Jake looked at himself in the mirror and felt utterly ridiculous! After his humiliating gym session, Curtis had handed him a bag of clothes that he had to wear for their routine Saturday afternoon hike in the forest.
The white shirt was bursting at the seams, the buttons gaping so that unless he sucked his toned stomach in, you could see the bare flesh beneath. The leather trousers were like a second skin and barely covered his ample bubble butt. The purple silk bikini briefs were so tiny that it was similar to wearing a thong and they barely covered his butt either, so his ass crack was on show. What was making things more uncomfortable was the silver cock ring that he’d been told to put on. He’d never worn one before and it was keeping him in a constant state of arousal.
Curtis had then given him a pair of black leather lace up dress shoes that were a size too big with short laces that didn’t allow him to tie them very effectively and black socks.
‘You better hurry up, mate,’ Curtis said through the changing room door. ‘The girls will start coming in for Pilates soon and I doubt you want to be caught wearing that.’
With a resigned sigh, Jake opened the door and after a smile from Curtis, he followed him out of the gym and to the car.
Jake’s leather clad ass creaked on the leather seat as he got into the car and his shirt dug into his sides as the material pulled in even more tightly.
Curtis tried to make conversation on the drive to the forest layby they parked in, but Jake only responded when he had to. He still couldn’t believe that his best friend was blackmailing him. The other thing that kept playing on his mind was how much his cock seemed to be enjoying it. Twice now, Curtis had made Jake cum, and he just couldn’t stop himself from wondering what would happen next, which gave him a constant semi-erection.
When they pulled into the layby, Jake opened the door to get out, but Curtis didn’t move.
‘I have somewhere to be, so I’m not going to do all of the hike. However, here’s your instructions and I’ll be back to pick you up later.’
‘You mean, I’m hiking alone wearing this?’
‘You know what the alternative is.’
Jake snatched the piece of folded paper from Curtis’ hand and got out of the car as quickly as his restrictive outfit would allow. He left all of his stuff in Curtis’ car at Curtis’ instruction and watched as Curtis sped off, leaving him dressed in a ridiculous skintight outfit in the forest.
‘This is insane,’ Jake muttered to himself as he walked into the forest a little, so he was away from the road, before opening the piece of paper.
It’s time for your solo forest walk.
However, there’s a slight catch . . . I’ll pick you up from the West layby in 2 and a half hours. However, an hour into your walk when you reach the Oak Summit, you’re going to do a little task. You’ll find instructions taped to an oak tree when you get there and you better hurry because if the task isn’t completed and you aren’t there to be picked up, then you’ll have to make your own way home.
Enjoy!
Jake tossed the piece of paper into a bush and before he could process the enormity of what he had to do, he started walking towards Oak Summit, a hill that was crowned with a number of old oak trees.
Oak Summit took at least an hour to get to and it was a further hour to get to the West layby. If he had to do a task in the middle, he was going to have to really rush. The downside was that the tight outfit was incredibly restrictive, and Jake found himself unable to walk particularly quickly. It was made worse by the fact that his leather thighs creaked every time they rubbed together, the silk caressed his butt and his balls, and the cock ring was keeping him semi-erect.
It took nearly an hour and fifteen minutes before Jake reached the base of Oak Summit. The sun was up, and his white shirt was practically see through. He could feel how damp the purple silk bikini briefs were underneath his leather trousers and he was irritated by the loose dress shoes that kept slipping off his heels.
With a sigh, Jake started to walk up the steep incline to get to the top of the summit. The leather was now glued to his thighs from the sweat, and he could feel the moisture running down his back and into his butt crack. He couldn’t wait to get this hike over. It was making him so annoyed that he was half tempted to just let Curtis share the pictures. But every time that thought occurred to him, he felt sick and decided to keep going.
Just as he reached the top of the summit, his right dress shoe slipped off his heel and he stepped out of it. He twisted his upper body to turn around and put it back on, which was when two of the shirt buttons popped off, exposing his tanned, and muscular chest.
Cursing, Jake rammed his foot back into the shoe and shuffled along until it was back on properly. He found an envelope taped to one of the trees and tore it open.
The Task!
You’re going to hate this and I’m going to enjoy it! As you know, the path that leads down to the West layby is a curvy narrow path on a gradual decline.
Your task is this – after every 100 steps, you will remove an item of clothing and leave it in the middle of the path. The only items that can stay on are your socks and the cock ring.
Once you’re down to wearing just them, you will walk a further 300 steps before being able to run back and retrieve your clothes. Only then can you get dressed again.
The best part? I’m currently sat in my car in the West layby watching you read this on my laptop. I stole a loud of equipment from the media studies department and the path is rigged so I can watch you complete your task.
If you fail to comply, you know the rules.
Now, get moving, you don’t want to be left stranded in that outfit. Let’s just hope that no one wanders down that path, if you have to hide or stray into the forest then you might miss your lift.
Good luck . . . mate!
Jake looked around to try and see the cameras, but with the time limits in place, he knew he couldn’t afford to hunt them down.
The path to the West layby was usually deserted as it was further to drive to than any of the others, so there wasn’t usually anyone wandering around there.
‘Okay, I can do this,’ Jake said to himself.
Jake started the count to 100 as he made his way down the long winding path to the West layby. The path was only four feet across, and dense bushes and trees grew up the sides the whole way along.
When Jake reached 100, he kicked off the left dress shoe and left it in the middle of the path. After another 100 steps, he kicked off the right dress shoe, leaving it on its side.
Jake was now sweating profusely and was almost looking forward to getting naked so that his legs and ass would get some air.
After another 100 steps in his socks, Jake went to undo the remaining buttons on his shirt, but two of them came off in his hands leaving only one button still attached. He undid it and with some difficulty, he managed to pull the skintight, wet material from his sticky upper body.
With a quick glance around, Jake dropped the shirt into the middle of the path and continued on.
When he reached 100 again, he was already starting to feel a bit cooler. He undid the button and fly on the leather pants and started to pull them down, but they wouldn’t budge. The sweat was making the leather stick to his legs and butt like glue, and they just wouldn’t move.
Cursing under his breath, Jake bent over to tug them down from the knee and as he did so, he heard a small ripping sound. He ran his fingers along the rear seam and felt a small hole in centre of the seam.
With some effort, Jake managed to get the leather trousers to his knees, the cool air on his thighs making him sigh with relief. He kicked them off and left them on the path before pulling the silk bikini briefs out of his butt crack. The silk was sodden and his balls were hanging out of the side of the pouch.
After tucking himself back in, Jake started to get hard again and the cock ring made his dick jump and pulse with arousal.
By the time Jake had completed the next 100 steps, his purple briefs had crept back up his ass and he yanked them out before sliding them to his ankles. He stepped out of them, his hard cock swinging free.
Leaving the briefs behind wasn’t as easy as he was now naked except for his socks and the cock ring. He couldn’t stop wondering what would happen if someone came along. What the hell would he do?
Jake stood up resolutely and carried on walking forwards, counting to 300 and moving as quickly as he could.
Just as Jake reached 234 steps, he heard a sound and stopped in his tracks. He got as far as 239 when he heard the unmistakable sound of voices. At 252, he knew the voices were coming towards him and he dived into the trees on his right-hand side and crouched down, thankful that he’d be hidden from sight.
The voices became clearer, and his heart sank when he realised it was three guys from the rugby team.
‘Curtis was right, this is a better route,’ one of them said.
‘Yeah, I always wondered why him and Jake did their weekly hike. It’s not bad.’
Jake couldn’t believe it. Curtis had set him up and now he was naked in the forest with three of the guys from his rugby team. He still had another 48 steps to do before he could go back and retrieve his clothes.
As the voices disappeared, Jake stuck his head out of the bushes and was relieved to see that the path was empty. The guys were obviously heading up to the summit so he should have plenty of time.
Jake completed his last 42 steps before turning around and running back in the direction of his clothes. As his socked feet padded along the dusty forest floor, he had the shocking realisation that the three guys from the rugby team would have had to have walked past his clothes.
Jake felt sick.
What if they took them? Or ripped them? Or threw them somewhere?
As Jake approached a corner on the path, he stuck his head around to make sure the path was clear and he was relieved to see his purple silk bikini briefs crumpled at the side of the path.
Jake grabbed them and pulled them up, relieved to no longer be naked. His hard cock was starting to hurt from being solid for so long and it barely fit into the small silk pouch of the briefs.
Feeling a little happier and praying he wasn’t out of time yet, Jake continued to run down the path, but when he reached the place he’d left his leather pants, they were no longer there. Panicked, Jake ran further along the path, but aside from two buttons, his shirt was gone as well.
‘This can’t be happening,’ he said in a whisper as he ran further along the path.
As he approached the next bend in the path, he heard voices again and held back.
‘There’s the other shoe,’ one of the guys laughed.
‘Who the fuck would leave their clothes out here?’ another said.
‘Dunno,’ the third one said. ‘What shall we do with them?’
‘You don’t know where they’ve been, mate. Just toss them in the trees and leave them.’
The boys muttered their agreement and Jake waited impatiently for them to move on.
When their voices had disappeared into the distance, he rounded the corner and raced along the path, desperately trying to see where they’d thrown his clothes.
Jake spotted a shoe at the side of the path and bent down to pick it up, the purple silk sliding into the deep crevice of his crack. He looked around like a mad man trying to spot his clothes and was relieved when he saw his leather pants and the shirt caught up on a tree.
Jake pushed his way into the bushes around the base of the tree and stepped on the other dress shoe. He pushed his foot into it before jumping up and grabbing the trousers and the shirt.
Jake pulled the shirt on and left the buttons undone, before slipping off the dress shoe he’d put on and pulling on the leather trousers. The inside of the trousers was still damp, and it was no easy task to get them back up. His throbbing hard cock made matters even more difficult, and he could only get the fly halfway up thanks to the tent in the purple briefs. The trousers were still unbuttoned, but they were so tight that they weren’t likely to fall down so Jake slipped the shoes back on and ran in the direction of the West layby.
When Jake was most of the way there, the right dress shoe flicked off of his foot and skidded away from him. Dripping with sweat, Jake turned around and bent down to retrieve it, but that was the worst thing he could have done. His leather trousers had been stretched to their limits since he put them on and with a small hole in the rear seam, they finally gave up. With an almighty loud rip, the trousers shredded open with a loud RRRRIIIPPPPP, and the rear seam burst open from crotch to waistband, his purple silk clad butt coming into view.
‘Oh, shit!’ Jake said as his hands flew to his butt to inspect the damage.
He stood up and the leather trousers fell down at the front revealing the tent in the briefs.
Jake pushed his foot back in the shoe and holding on to the leather trousers at the front, he continued the run to the car park. However, with the leather trousers already ripped open, the pressure of his bulging thigh muscles as he ran caused the ripping to spread slowly down the inside thigh seams and by the time he got to the layby, they were ripped down to the knee on both sides.
‘He’s still here,’ Jake said with a sigh of relief.
‘Looks like you made it,’ Curtis said as he got out of the car.
‘I can’t believe you set me up like that – what the fuck would I have done if the guys had seen me?’
Curtis just laughed. ‘You should see the video – it was a great show.’
‘You’re an arse hole. Take me home.’
Curtis locked the car by pressing the button on his key. ‘You don’t seriously think you’re just going home?’
‘What more do you want?’ Jake yelled.
‘I’d be quieter if I were you. The guys from the rugby team are probably heading back about now and you wouldn’t want them to see you like this.’
Jake hadn’t thought of that and started to panic at the thought of it. ‘What do I have to do?’
‘Simple! Get naked and Jake off until you cum. Then I’ll give you some proper clothes and take you home, but if we start to hear the guys coming back, I leave you here.’
Jake didn’t hesitate. He pulled the shirt off, flicked the shoes off of his feet and kicked off the torn remnants of the leather trousers. He tugged the briefs down and his cock slapped against his stomach as it came free from its silk prison.
Jake groaned as he grabbed his cock. He’d never known it to be so hard in his entire life and it was almost sore from being hard for so long. He jerked off as fast as he could, his free hand going from his butt to his balls and back again.
‘Slap your arse a bit,’ Curtis instructed, and Jake didn’t miss the bulge in Curtis’ jeans.
Jake did as he was told and gently slapped his bubble butt, the cheeks bouncing slightly with each smack. His slaps got harder, and he started to moan more loudly as he felt his balls tighten. Part of him was terrified of getting caught, but he couldn’t deny that the whole situation was turning him on.
Jake was on the brink of blowing his load everywhere when Curtis stepped towards him and grabbed his wrist.
‘You can stop now.’
Jake’s cock throbbed and pulsed as if it was looking for the hand that had been stroking it.
‘What do you mean? I’m nearly there.’
Curtis shook his head and smiled. ‘I don’t think we’ll let you cum just yet.’
Curtis unlocked the car, opened the door and tossed Jake a pair of navy satin shorts and a black vest. ‘Put those on and get in.’
Jake’s hand went back to his cock, but Curtis shook his head. ‘If you cum, you’re finished.’
Jake had never felt so frustrated in his life and he practically let out a sob as he pulled the shorts up over his painfully throbbing hard on. He pulled on the vest and climbed into the car, the shorts tenting obscenely.
‘Now what?’ Jake asked.
‘Now, we’re going to mine to change and then head out to the movies, just like we always do.’
‘You want me to Jake off at your house?’
Curtis laughed. ‘I never said that but enjoy the rest of the evening with that hard on.’
Jake gritted his teeth in frustration and desperation. What had started off as something terrifying had become fun and sexual, but it was now turning into something torturous. How the hell was he going to get through the evening?
