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JockMailed - Chapter 5
🕑 Added 2025-09-07 15:34:17 +0000 UTCI'm excited to share the next updated instalment of JockMailed - fans of thongs and gym fails will love this one! If you enjoy this chapter, please give it some love.
Jake awoke the following morning and looked down at the list of instructions that Curtis had given him the day before. He still couldn’t believe he was being blackmailed. His best friend, Curtis had discovered that he was gay and had taken God knows how many photos of him getting fucked in the woods. Curtis was slowly deleting the photos, but that meant Jake completing certain tasks, like wearing trousers to school that were 2 sizes too small when he was freeballing underneath.
Jake showered and came back to his room with a towel wrapped around his waist, his muscular upper body still glistening with droplets of water. He picked up the sheet of paper with the instructions and felt the knot in his stomach tighten.
“Saturday has always consisted of a session at the gym and a hike in the forest. This week is not much different.
However . . .
That thong you wore on the first day needs to be worn under your gym shorts and make sure you wear those baggy black gym shorts.
For the hike, you don’t need to bring clothes as I’ve got them ready and waiting for you . . . along with a few extras! Let’s hope you’ve got plenty of energy!”
Jake pulled out the silk thong and felt a wave of arousal rush over him. He remembered the struggles the day he’d worn it – constantly falling out of the pouch, the tight feel of the string between his meaty arse cheeks . . .
Jake dropped his towel and struggled to get the thong around his waist. As he was pulling it up, he noticed the small rip in the waistband, right at the place where the rear string met the band. He pulled his cheeks apart so that the string could rest a bit more comfortably, and spent some time trying to adjust his bulge so it stayed in place, before pulling on a white sleeveless tee and his baggy black gym shorts and trainers.
Since they were 15, Jake and Curtis had gone to the gym every Saturday morning. They always did a long workout, showered and then went for a hike in the forest – no matter what the weather. It had been one of Jake’s favourite times of the week, but now it was tainted and he was dreading it. To make matters worse, Jake couldn’t stop thinking about the mind-blowing orgasm Curtis had given him the previous day in the storage locker at school. It had been the most phenomenal hand job he’d ever had.
‘Ready to hit the weights?’ Curtis asked when Jake arrived at the gym.
Jake kept quiet as they did their usual cardio workout. He was fine on the bikes, but when they got on the treadmill, his ample cock and large balls flopped out of the small pouch of the thong after just a couple of steps. Curtis barely took his eyes off of Jake’s crotch as he watched Jake bounce around in the thin black material.
‘Okay, weight time!’
Jake followed Curtis to the free weight’s area and they both started with some light bicep curls, before moving on to some heavier arm work.
‘I reckon it’s time for squats with the barbell.’
Jake got into position and squatted down to lift the barbell. He wrapped his fingers around the metal bar and making sure his back was straight, he pushed through his legs and stood up before raising it above his head and then resting it over his shoulders.
‘I reckon you can manage 5 sets of 10 today,’ Curtis said with a grin.
Jake steadied his breathing before dropping into the first squat, but no sooner had he reached the bottom of the squat, there was a loud snapping sound and Jake felt the waistband of the thong give way.
Oh no, the rip – he thought.
Curtis had heard the snap and guessed what had happened, but watched Jake continue. As he did, the front of the thong fell away from his manhood and slowly worked its way between his legs before it was hanging out of the right leg of his shorts. The only thing keeping the thong on at all was the rear strap that was buried between his ample cheeks.
As Jake continued his squats, Curtis grabbed the material hanging from Jake’s short leg and slowly started to tug on it. The feel of the material being tugged between his cheeks made Jake hard in a matter of seconds and he soon had an extremely obvious tent in his shorts.
Jake lowered the weights and stood up, his hands rushing to his crotch in an attempt to hide his hard on.
‘I need to go and change,’ Jake said, his face blushing red from embarrassment at being in the middle of the gym with a hard on, whilst wearing nothing but baggy shorts.
Curtis looked around and with no one in their vicinity, he stepped closer to Jake and grabbed his cock through his shorts.
‘Looks like someone is enjoying themselves again!’
‘Curtis, please, not here,’ Jake moaned, the grip on his cock making his eyes close.
‘You’re right, let’s go shower and head off early.’
Jake was amazed at this and had to hurry to catch Curtis up.
Curtis pulled down the door handle, opened the door and stepped through, before stepping to the side and holding it open for Jake.
Jake hesitantly stepped through, unsure what Curtis was playing at.
‘After you, dude.’
Jake stepped through the doorway, but before he got any further, Curtis grabbed the waistband of his shorts at the back, flipped them over the door handle on the inside of the gym and slammed the door shut.
It happened so quickly that Jake barely realised what was going on as he continued to walk forward. There was an almighty rip as the thin, baggy shorts shredded from his body, freeing his rock-hard cock that slapped loudly against his stomach.
Jake grabbed his sleeveless tee and tried to pull it down to cover himself, but it only just reached the bottom of his stomach and was so tight that there wasn’t much material to play with.
Luckily for Jake, there was no one in the hallway, but the thought of someone coming at any moment was terrifying, but inexplicably, at the same time, incredibly arousing.
Curtis grabbed his meaty arse and bent forward to whisper in his ear.
‘Looks like you enjoy being naked in public places.’
Before Jake could utter a word, Curtis grabbed the shoulders of Jake’s tee and tore it from his body in one swift movement, leaving a stunned Jake in nothing but his white socks and trainers.
Jake was frozen to the spot in complete confusion. He knew he needed to run before someone came, but he was in shock that Curtis had stripped him naked right there in the hallway.
Suddenly, they could both hear voices coming towards them down the corridor. There was a corner about twelve feet from them, and the voices were getting louder.
Curtis saw how stunned Jake was and decided to go the whole way. He grabbed Jake’s dick in his hand and with just a couple of strokes, Jake started to shoot his load all over himself and the carpet. Thick ropes of cum shot from his throbbing cock and he was panting like a dog.
As soon as he started to cum, Curtis slipped past him and dived into the changing room. Jake managed to gather his senses just as two guys walked around the corner. Jake couldn’t be sure if he’d been seen naked or not, but he just prayed the guys didn’t look on the floor where he’d left a puddle of cum.
‘Your clothes are in there,’ Curtis said, tossing him a bag as Jake wrapped a towel around his waist.
Jake ignored him and dumped the bag on the bench before heading for the shower.
Curtis was already dressed when Jake emerged, and he took great pleasure watching his friend dry off.
Jake opened the bag and pulled out a white shirt that looked way too small for him, a pair of leather jeans that would definitely be on the tight side, a pair of purple silk bikini briefs that wouldn’t cover his bubble butt in a million years and a thick silver ring that he recognised as a cock ring.
‘Are you kidding me with this? You expect me to wear this in the forest. We bump into people on our hikes sometimes?’
‘Wear them or your reputation is history. Your choice, mate.’
Jake prayed that no one at the gym would see him leaving, but knowing he had no choice, he started to dress, praying that the day wouldn’t get any worse. Or perhaps it was better . . . he just wasn’t sure.
