JockMailed - Chapter 3

My incredible higher tier patrons voted for a JockMailed story for their June Monthly Story, and I was more than happy to oblige - so much so that I've made it a new chapter in the full JockMailed story because it ended up being so much longer than planned.

I hope you guys enjoy this longer one!

When Jake arrived in the Art Room the following morning, he was expecting to find someone there waiting for him, but instead, there was just another infuriating envelope on one of the tables addressed to him. He tore it open and pulled out a solo sheet of paper.

“I thoroughly enjoyed the show you put on yesterday afternoon, nearly as much as those freshman guys did. Today’s task is a little different – there’s no undies or tight clothing for you; you can keep wearing whatever you’re in . . . for now.”

Jake was relieved that he wouldn’t have to change. He wasn’t sure he could handle another day of slutty teasing undies, or trousers so tight that they burst at the seams. Aside from the potential risk of embarrassment or humiliation at any minute, he wasn’t sure he could deal with being that horny again. He’d cum more times in the last couple of days than he had in the last week.

“Your task today is a cum challenge! You will have to cum three times during the school day, and you will find a list of locations below. I know this challenge may seem a little harsh, but hey – you get to cum at school and I know you’ve done that plenty of times before.

If you successfully complete today’s challenge, I will delete another 25% of the footage I have, and you might get a nice surprise tomorrow morning.”

The thought of having that much deleted felt like a relief to Jake, but when he looked at the list of locations, he wondered if he should just let it come out who he really was.

“Location 1 – 10:20 – Auditorium – you’ll have ten mins to blow your load on stage before the orchestra comes in for rehearsal – I expect you to be naked from the waist down for this one.

Location 2 – 12:55 – Locker Room – you’ll have fifteen mins to cum before you finish swim practice, and for this one, you need to put on the undies of one of the teammates you fancy.

Location 3 – 14:20 – History Class – there’s a storeroom behind your desk at the back of class – you will need to sneak in there, get naked and cum. Easy!”

Jake looked at the list of directions and felt a weird combination of terror and arousal. Whoever was bribing him had a serious public play fetish, and Jake couldn’t deny that he was into it.

His first class passed by in a blur, and before he knew it, he was excusing himself early and moving as quickly down the halls as he could to the auditorium. He was fairly certain it would be empty at that time of day, but it was already 10:15 and he didn’t want to risk someone from the orchestra arriving early for rehearsal.

The auditorium was dark except for a couple of lights on stage. Jake walked down the aisle between the rows of seats, being careful not to trip over his own feet. He was relieved to see that the sound and lighting box that was housed above the entrance was in darkness, which meant no one was up there watching him. He checked both wings and returned to the stage at 10:21.

He had nine minutes, possibly less.

“Okay, I can do this,” he whispered to himself as he toed off his dress shoes. His hands went straight for his belt, and he undid it, before popping the button on his grey uniform trousers. His hands stilled after he’d undone the fly. Was he seriously going to risk being naked from the waist down in the middle of the stage at school?

“Fuck it!”

Jake pushed his trousers down over his muscular bubble butt and thighs before kicking them off. Just his white boxer briefs remained. He was about to grab his trousers and put them back on when his cock throbbed and he looked down. He was already hard as a rock and tenting his boxer briefs, a wet patch in the material a clear sign that his body was definitely onboard with this challenge.

The sight of his cock tenting his undies was all Jake needed to push them down to his ankles and kick them away. The head of his cock glistened with precum, and he couldn’t resist swiping a finger through it before sliding the finger into his mouth and tasting his own juice. It was so good.

“Stop! You’re not supposed to enjoy this,” he chastised himself before wrapping his hand around his cock. He had six minutes remaining, but he was confident this would take no time at all.

Jake bit down on his full lower lip as he jerked himself fast and hard. He hadn’t cum yet that morning, and it was only seconds before he felt his balls starting to tighten.

“Ah fuck,” he gasped as the first rope of cum shot across the stage and splashed on to the hard wood floor. He milked his dick until he was dry but still panting for breath. He was just about to turn around and grab his boxer briefs when he heard voices.

“Oh no,” he hissed before bending over, grabbing his bag, his trousers, his boxer briefs and his shoes, and running off into the wings of the stage.

The lights in the auditorium flickered to life as a few of the seniors in the orchestra walked down the aisle towards the stage.

Jake hurriedly yanked his boxers briefs on over his still leaking cock, dragged on his trousers and pushed his feet into his shoes as he zipped up. His load was still on the stage, but he couldn’t do anything about that. He threw his bag over his shoulder and followed the narrow corridor that led from the stage to a corridor that passed two dressing rooms and led back out into one of the school hallways.

“Fuck, that was close,” he said with a sigh as he tucked his shirt back in.

Feeling relieved that he’d completed one of the three, Jake headed over to the library for an hour before going to the sports facility so that he could get changed for swim practice. He had no idea how he was going to manage leaving the pool and jerking off, but he’d have to think of something.

It was just after 12:15 when he dived into the pool with the rest of his class. His best buddy made a comment about being hungry for lunch and Jake agreed that he’d get showered and head to the café as soon as coach blew the last whistle.

But first, Jake had something more pressing to take care of.

As he swam the laps and tried not to focus on the time, Jake couldn’t believe that he was chubbing up inside his speedo. How was it possible to be so horny when he’d only just cum?

At 12:50, Jake climbed out of the pool and asked coach if he could be excused to use the toilet for a bit, claiming that he had an upset stomach. Given that Jake had never made such a request before, coach just nodded and sent him on his way.

The changing room was three lines of benches and various pegs and coat hooks. The school didn’t believe in lockers for sports as students were expected to use their main locker to store anything when they weren’t in class. This meant that Jake had easy access to his team’s undies, and he knew exactly who’s he’d be wearing.

Curtis has been his best mate for years and although their relationship was completely platonic, Jake had always fancied him. He was muscular and handsome, and Jake knew that he was always wore boxer shorts – sometimes silk, sometimes satin, sometimes cotton, but they always had a button fly, and Jake had dreamed of popping those buttons and sliding his hand inside.

Curtis had changed next to him and Jake easily found his bag. He zipped it open and found Curtis’ silk boxers, a navy pair with gold trumpets and tubas printed on them. Jake wrestled his speedo off, his cock already hard from retrieving Curtis’ boxers. He grabbed his towel and dried himself off before stepping into the boxers and pulling them up. Curtis was a little slimmer than him, and the combination of the tighter boxers on his damp skin felt incredible.

Jake had been thinking all morning about how he’d do this, and he undid the buttons on the silk boxers before fishing his hard cock out through the fly. Fuck, he wished he was doing this to Curtis. Thinking about his best mate whilst he was wearing his boxers, Jake wrapped his hand around his cock and started to stroke.

The combination of the silk teasing the base of his cock and his balls, his damp skin and the knowledge that he was jerking off in his best mate’s boxers was enough to make Jake cum in seconds, but he wanted to enjoy it. Yes, he was being forced to do this, but there was no reason he couldn’t enjoy it, and fuck did it feel good.

The team could walk in at any point, but Jake was past caring as he fucked his own fist, visions of ripping Curtis’ trousers open and sliding his hand inside the fly of his boxers bringing him closer and closer to the edge.

Jake would have dragged it out even longer had it not been for the loud sharp blast of coach’s whistle.

“Oh shit,” Jake gasped, fucking his hand faster as he chased his orgasm.

Thankfully, he’d been on the edge for a few minutes, and it only took a matter of seconds before the first splatter of cum landed on his right foot.

Without any time to fully enjoy the orgasm, Jake yanked down the boxers, praying that he hadn’t gotten cum on them, before wrapping his towel around his waist. He shoved the boxers back in Curtis’ bag and hastily zipped it up just as the first of the team entered the changing rooms.

Jake immediately sat down on the bench, hoping that no one would notice his still hard cock or the fact that he was still leaking cum.

“You doing okay, Jake?” Curtis asked as he came over and grabbed his towel. “You’re looking a little flushed.”

“Yeah, just feeling a little rough. I’ll be fine after some food I reckon.”

Jake did his utmost to act casual as he showered and tried not to watch as Curtis dropped his towel and pulled on his silk boxers. Jake was praying that Curtis wouldn’t notice anything because if anyone had been in the changing rooms touching his undies, it would have to be Jake as he was the only one in there unaccompanied.

Thankfully, Curtis didn’t notice a thing, and they headed off to lunch, leaving Jake to wonder how the hell he’d manage to get naked in his history teacher’s storeroom.

History was Jake’s least favourite class, and he always sat on a desk at the back of the room with Curtis, but for some reason, Curtis hadn’t turned up to the lesson, leaving Jake alone at the back of the class.

That, at least, made his life a lot easier.

Once the lesson had started, their teacher did his usual and put on some hideous world war video. For once, Jake was thankful for the video, and as the clock hit 14:20, he slowly stood up, stepped backwards and wrapped his hand around the door handle. He did a quick sweep of the room to make sure no one was looking in his direction before he pulled it open, stepped inside and closed it as quickly and quietly as possible.

Sighing with relief, Jake waited for a minute in case someone had seen him and came to see what he was up to. But when he was confident that no one was coming his way, he toed off his dress shoes, pulled off his blazer and unknotted his tie before pulling it free from his shirt.

He couldn’t believe that he was about to get naked in a storeroom just a few feet away from his classmates. He really had reached a level of insanity that he didn’t know was possible. Sure, he was being blackmailed, and he had no choice, but his already throbbing dick was more than enough to tell him that he was enjoying this.

Jake unbuttoned his shirt and couldn’t resist giving his nipples some attention before he pulled it off and dropped it on the floor with his blazer, tie and shoes. Next, he undid his belt, unbuttoned and unzipped his trousers and removed them, before adding them to the pile.

Finally, he yanked down his boxer briefs, noticing a new damp patch next to the dried one from earlier. He’d have to sneak those into the wash when he got home.

Jake looked down and realised he still had his socks on. Not wanting to risk failing the challenge, he pulled off both socks and tossed them on the pile.

And that was it – he was butt naked in a storeroom, hidden from the rest of his class by a door that had no lock. He was insane!

Not wanting to focus too much on the risk, Jake started jerking off. After cumming twice that day, he was still horny, but he knew he’d something to make him cum quickly, and there was only way that he knew he could do that. With his free hand, Jake sucked on his index finger before sliding it between his cheeks and pressing it against his hole.

Jake forced down a moan as his dick throbbed his hand and his hole twitched against his finger. He couldn’t believe he was going this far, but he needed to cum already. There was no clock in the storeroom, and he couldn’t risk being in here when the lesson ended as everyone would notice he’d gone, and his stuff wasn’t.

Putting more pressure against his hole, his finger pressed against the ring of muscle. Jake tried to relax but he was jerking his cock too fast to focus on two things at once and settled for just rolling his finger around his entrance. The sensitive nerves there were more than enough to make his body hum, and he felt his balls start to tighten.

“Oh, fuck, fuck, fuck,” Jake whimpered as his entire body tensed and a rope of cum shot from his cock and splattered on to one of his shoes, quickly dribbling down the polished leather.

Jake continued to fuck his hand as he fingered his hole, cum continuing to leak from his cock as he did his utmost to keep quiet. The last thing he needed was to get caught in that position.

Once he’d finished one of the most incredible orgasms, Jake grabbed his boxers from the pile. Thankfully, they’d been on top, but they’d caught most of his load and were soaked.

“Fuck it,” he sighed, putting them aside on one of the shelves. He’d just have to go commando again.

Jake got dressed as quickly as he could, trying to be silent. He zipped up carefully, praying that his cock wouldn’t leak anymore, tied the laces on his now sticky dress shoes and after taking a deep breath, he opened the door and stepped back into the classroom.

No one paid him the slightest attention as he sat back down, just as the bell rang to signal the end of class, and the end of the day.

Jake sagged in his seat, sighing with relief. He’d done it. He’d actually done it. He waited for everyone else to leave before heading to his locker where he found Curtis grabbing stuff from his own locker.

“You feeling any better? You look flushed.”

Jake coughed. “Yeah, just need some sleep maybe. Uh, catch you later.”

Jake opened his locker and sighed when he found another envelope that he stashed in his bag, along with a couple of books he needed for homework. He left school and made sure he was alone, before ripping open the envelope.

“You certainly surprised me today! Not only did you complete the challenge, but there was no mistaking how much you enjoyed it. Tomorrow, you need to be at the art studio for 8am again. I think it’s time we met!

P.S. I’ve deleted an additional 25% so 57% has now been deleted.

P.P.S. Don’t worry, I’ve retrieved your boxers from the storage room for you. I’ll keep hold of those."

Jake blushed when he realised that he’d left his boxers behind in history. Not only had he forgotten them but now his blackmailer had them. Some pervert had his cum stained undies. Why did that thought make his exhausted cock twitch?

And he’d finally get to meet his blackmailer? Who the hell could it be?