JockMailed - Chapter 4

I'm excited to share the edited and amended Chapter 4 (previously 3) of JockMailed. I hope you guys enjoy this one - give it some love if you do!

When Jake arrived in the old Art room at 8am the following morning, he was more than a little apprehensive at what, and who, he’d find. After the thong and the insanely tight trousers, not to mention the epic jerk off challenge, he was incredibly nervous at what he might end up having to do next, let alone who was behind the blackmail.

Jake sat down on the edge of one of the tables, finally feeling comfortable in a pair of grey trousers that fit and wearing a pair of boxer briefs that didn’t give him an instant hard-on or that he fell out of every few seconds.

It was nearly ten past eight when the door opened and Curtis Jakeson entered the room wearing an exceptionally smug grin. Curtis was one of Jake’s closest friends and had spent his entire school life being second best. Jake always seemed to get everything he wanted, including captain of the rugby club that Curtis had worked much harder for.

Jake couldn’t believe it when Curtis revealed himself as the blackmailer. He felt hurt more than anything, before the anger kicked in. Curtis has been his best friend for longer than he could remember. Why would he do this to him?

‘Don’t try anything, Jake or the material I have left will be all over the school and the internet, including the footage of your many jerk-off sessions yesterday.’

‘What the hell do you want from me, Curtis?’

Curtis just laughed. ‘To humiliate you and make you feel like you’ve spent years making me feel.’

Before Jake could respond, Curtis tossed him a manila envelope. Jake opened it with trepidation and pulled out a pair of black and purple silk bikini briefs.

‘What are these supposed to be?’

‘They’re silk bikini briefs,’ Curtis said with a grin. ‘You’re going to put them on underneath your uniform and you’ll be wearing them during practice after school. Oh, and I’ve taken care of your kit for you for practice. It’s ready and waiting in the locker room.’

Jake felt sick at the thought of what the kit could be for practice.

‘Fine, I’ll wear them.’

‘What? No arguing with me? I thought you’d have some fight left in you. Or are you happy to be wearing another pair of my undies?’

Jake blushed, the memory of jerking off in Curtis’ boxers flashing through his mind. He couldn’t believe that he’d picked Curtis’ undies. He didn’t think it was possible to feel even more humiliated.

‘What’s the point in arguing? You’ll just blackmail me.”

Jake went to leave, but Curtis stopped him. ‘You can put them on now. Be quick, I want to get coffee before first class.’

‘You want me to change in front of you?’

‘Yes. If I say change in front of me, you do it. If I grab that big arse of yours, you deal with it. If I tell you to get on your knees and suck my cock, you’ll do it. Either that, or your reputation is history.’

‘Since when did you turn gay?’

Curtis’ face coloured red and he closed the gap between him and Jake in seconds. ‘I’m not . . . Just do what you’re told. I’m just telling you how things are going to work. Now, put the briefs on.’

Jake held his hands up in surrender before kicking off his black leather slip on shoes. He unbuttoned his grey trousers, lowered the zipper and started to wriggle out of his trousers. His boxer briefs had ridden up his ample butt and the lower half of his cheeks was on show. He pulled them down too and kicked them and his trousers away.

The silk briefs were black silk with purple edging. They looked tiny and he was worried about how he’d get them on.

Jake stepped into them and got them as high as his muscular thighs before he had to really wrestle them up to this waist. He managed to get his cock and balls in the front, but the rear of the briefs barely covered his big butt. The bottom two thirds of his firm cheeks were on show, and he was worried that the line would show through his trousers and everyone would think he was wearing girl’s French knickers.

Jake turned around to pick up his trousers and jumped when Curtis stepped up behind him and groped his right butt cheek.

‘What the fuck are you doing, dude?’

‘I told you; I’ll do what I want! Now get dressed or do you want to suck my cock first?’

Jake wasn’t sure if Curtis was being serious or not, so he got his trousers back on as quickly as he could and slipped into his shoes.

Curtis left before Jake was dressed, so he just headed off to his first class, conscious of the fact that the soft silk felt amazingly sensual against his ample bulge.

Jake’s morning was fairly uneventful. Curtis acted like nothing was different between them and classes were as dull as ever. The only issue was that Jake was becoming increasingly aroused by the silk briefs, which wasn’t being helped by the fact that he had to constantly pull them out of his arse crack every time he moved.

When Jake sat down for his double English class in the afternoon, he couldn’t wait for the day to be over so he could get home and Jake off. He had a constant semi-hard on and couldn’t concentrate on anything other than the soft silky feeling of the briefs.

The bell finally rang, and Jake remembered that he had practice. Not just practice, but practice wearing kit that Curtis had chosen.

He purposely dawdled on the way to the locker room so that most of the boys would be out on the pitch. He dreaded the thought of having to get changed in front of any of them whilst he was wearing the skimpy silk briefs.

When he pushed the door open, Curtis was the only one left. He was lacing his boots and had a devilish grin on his face. Jake opted to ignore him and opened his locker to find his rugby shirt and a pair of white shorts that didn’t belong to him.

The shorts were standard white rugby shorts, but they felt stiffer than normal, and they stunk of some sort of chemical.

Deciding that he didn’t want to give Curtis the satisfaction by asking questions, Jake stripped off and pulled his kit on. The shorts were fitted on his ample butt and thighs, but they weren’t skintight, which surprised him. He put his rugby boots on and headed out to the pitch, with Curtis following closely behind him, taking in the view of Jake’s thick arse in the bright white shorts.

Practice was hard. The coach had them doing some serious cardio warmups before they even started on scrum formation and passing. By the time practice was done, the whole team were dripping with sweat and Jake could feel the sweaty silk briefs wedged in his butt crack.

‘Hit the showers boys,’ Coach yelled after another passing run up the field. ‘Jake, Curtis, can you boys collect the cones up for me and drop them off in the storage locker?’

Jake watched the other guys leave and started to wonder why Curtis had wanted him to wear the white shorts or the silk briefs all day. The white shorts were a bit stiff and uncomfortable, but that didn’t bother him a great deal, and aside from being in a state of arousal for most of the day, he loved the briefs. Not that he’d admit it.

Jake started bending down to pick up the cones, whilst Curtis just stood and watched him with a grin on his face.

It was when Jake bent over to pick up the sixth cone that he heard a rip and felt the shorts tear open down the right-hand seam exposing his muscular thigh. After the issues he’d had the day before with his trousers, a flash of his perfect thighs wasn’t going to bother him.

Curtis continued to watch as Jake kept retrieving cones and the more he bent down, the more his shorts continued to rip apart. It started on the side seams, but by the time Jake got to the thirteenth cone, he bent down, and the shorts burst open at the rear, exposing his barely covered rump in the sweaty silk briefs.

Jake jumped up and grabbed his arse to inspect the damage, but as soon as his fingers touched the material of the shorts, they just disintegrated. The more Jake tried to grab at them, the more the material just fell away in his hands.

Curtis couldn’t stop himself laughing as he watched Jake pulling his shorts to shreds. By the time he was finished, he was stood in his silk briefs with only a waistband and a flap of white material.

‘What the fuck did you do to these, Curtis?’

‘Oh, I may have accidentally soaked them in bleach. I guess that’s not good for the material. Nice briefs, silk boy!’

Jake was suddenly very aware of the fact that he was in the middle of the rugby pitch wearing his rugby shirt and a pair of skimpy silk briefs. He grabbed the last couple of cones and carried the stack in front of him to try and hide the fact that he had no shorts on.

Jake ran across the rugby pitch, his bubble butt bouncing with each step and Curtis following closely behind him enjoying the view.

The storage locker was a large metal shed to the side of the building and Jake decided to hide out there until he was sure the locker room would be empty.

He threw open the door and dropped the cones inside before Curtis came in behind him.

‘I think that rugby shirt looks a bit tatty to me.’

‘What are you talking about?’ Jake asked as he looked down at the shirt.

Curtis stepped forward, grabbed the shirt in both hands and literally tore the shirt from Jake’s body, exposing his broad shoulders, muscular arms, pecs and toned stomach.

‘What the fuck is wrong with you?’

‘I don’t know why you’re complaining, Jake. It looks like you’re enjoying it.’

Jake reddened as he looked down at his crotch and saw that his cock was getting harder by the second and was straining against the silk of the briefs.

He couldn’t deny that the adrenaline rush of losing his shorts and now his shirt was making him horny. The loss of clothing combined with the sensual feel of the silk and a day of arousal was too much for him to bear.

‘Maybe we should see just how much you enjoy it?’ Curtis said as he stepped forward into the small space and grabbed a hold of Jake’s throbbing cock through the briefs.

Before Jake could argue, Curtis put his finger on Jake’s lips. ‘You’re my bitch, remember? You argue, your reputation is gone. Your choice.’

Jake was torn. He’d fancied Curtis for years and, had this been happening under natural normal circumstances, it would be hot as hell, but Curtis was blackmailing him. Surely, he should hate him, not be enjoying the feel of his hand on his dick, whilst silently begging for release.  

Curtis slowly started to jerk Jake’s cock through the briefs and before long, the head of his large dick popped up above the waistband.

Jake’s breathing quickened when he heard the other guys leaving, but no one came near the storage locker.

Curtis continued to jerk him off as his other hand travelled up to tweak and play with Jake’s nipple. Jake groaned and started to buck his hips as he let go of the situation and just enjoyed the stimulating feeling of Curtis’ hands.

Jake was getting close, and he could feel his large balls starting to tighten. He bucked his hips harder until Curtis suddenly let go. They both heard footsteps pounding down the path and Curtis dived out of the storage locker and pushed the door to behind him.

Jake’s heart thudded in his chest when he stopped thinking about his cock and realised the position he was in. He was wearing nothing but his rugby boots and socks and the skimpy silk briefs that were not only damp with sweat but were now slick with his pre-cum across the front. His cock head was still above the waistband, and he was breathing heavily.

Jake heard Curtis talking to coach and he suddenly panicked that the coach might try and come into the storage locker. There was nowhere for him to hide and there was no way he wanted to get caught with his hard cock on full view.  

‘Jake went back for the last of the cones, Coach. He probably detoured to chat to some girl. I just thought I’d tidy up a bit while I waited.’

Curtis stepped closer to the doors and subtly opened one of them a few inches, just enough so that he could slide a hand inside, where he groped at the empty air before his fingers found Jake’s stomach.

Jake held his breath as Curtis ran his fingers down his stomach to his cock and started to slowly jerk him off, whilst he continued to talk to Coach.

Despite the panic he felt, Jake couldn’t help himself and he was soon thrusting into Curtis’ hand, his own hands over his mouth to try and hush his ragged breathing.

‘Well, I’m going to head off. I’ll leave you to lock up the storage locker before you go, Curtis.’

Jake was on the brink of an orgasm as Curtis increased the speed and ran his thumb over the head of Jake’s throbbing cock, his pre-cum acting as lubricant.

‘See ya, Coach.’

Before the sound of Coach’s footsteps had disappeared, Jake exploded. Thick ribbons of cum shot over his stomach, thighs and all over Curtis’ hand.

Curtis pulled the door open and grinned at the result. ‘Looks like someone enjoyed himself.’

‘Is Coach gone? I need to get dressed.’

Jake couldn’t even look Curtis in the eye. He’d just experienced one of the best orgasms of his life, at the hands of his best friend who was blackmailing him for being gay. It was an insane situation to be in, and he couldn’t deal with in that moment. He needed to leave.

‘Yeah, he’s gone. After you.’

Curtis stepped aside so that Jake could step outside and as he walked past, Curtis slammed his hand down on to Jake’s beefy butt with a loud slap.

‘Once you’re dressed, I’ll give you tomorrow’s instructions.’

‘Tomorrow is Saturday!’

Curtis laughed. ‘Yeah, and you’re going to hate it!’