The Clothes Sale

[Robert Brooks]

I’m loving this story so far!
Great that you have changed the undies to briefs, I think he wore boxers in the clip you shared. Way more embarrassing this way!
I love that the bullies have even been to his house to steal all of his clothes & underwear. I’d be really interested to know how that bit happened.

[DrWhoFanJ]

I’m loving this story so far!
Great that you have changed the undies to briefs, I think he wore boxers in the clip you shared. Way more embarrassing this way!
I love that the bullies have even been to his house to steal all of his clothes & underwear. I’d be really interested to know how that bit happened.

Always nice to see new users on the site! Welcome, Robert; hope you enjoy your time here.

I’ve always wanted to see a story where getting dressed is leveraged as embarrassing (as opposed to the usual getting stripped!), and decided to get on and make one myself with inspiration from that clip I found.

Oh, don’t worry, that chapter’s definitely in the plans for to you enjoy when we reach it!

[DrWhoFanJ]

CHAPTER 5

“What’s next? Ah, yes, these ripped jeans. I’ll go easier on you this time, Shane. All we need of you this time is to keep your hands on your head for a whole two minutes. Do that, and we’ll let you have your jeans again. Fail, and it’ll cost you!”

Shane looked embarrassed already just at the thought of showing his revealing briefs again, but knew he had no real alternative any more.

“I’ll do it,” he mumbled after a moment.

“I’m sorry, what was that?”

“I said I’ll do it,” he replied, only a bit louder.

“Still can’t hear you. Speak up, or lose your jeans as well.”

“I’LL DO IT!” he screamed.

“OK, OK, don’t shout, Weeny! We heard you.

“Well, whenever you’re ready, just raise your hands to your head and we’ll start the timer.”

Setting the sports hall’s lap timer to one minute, Jack turned back to Shane, waiting for the nervous young boy to do as instructed.

Slowly raising his hands upwards to reveal his briefs was torture for the young lad, but he knew he had no choice if he wanted to leave here with any chance of being dressed again.

Once they were firmly placed against his crown, Jack started the timer. This was the cue for the girls in the front rows of each set of seating to start leaning forwards and flashing their cleavage at the terrified Shane, with obvious effect. Shane could only watch in horror as his flaccid four-centimetre dick steadily grew into an erect fifteen-centimetre cock that caused his briefs to bulge so far that the entirety of his balls and pubic hair (and slightly-squashed-by-the-fabric penis) was now exposed to anyone with a view of his sides.

Clearly torn between lasting the remaining 90 seconds like this (with the problem downstairs only getting worse) and having to lose his jeans permanently, Shane’s mental anguish was only getting worse and worse with every face and camera he saw. He had to close his eyes to help keep him calm and hopefully prevent his boner from getting any more noticeable (or even worse, breaking the briefs entirely!).

Realising Shane could no longer see anything happening in the room (and banking on him having lost the sense of time with the heightened emotional state), Jack decided now was the time to hatch the next stage of the plan for this section to embarrass him even further.

[NudeBaG]

Enjoying this

[Robert Brooks]

Agreed, this story is awesome!
I love the detail of the side view of his tented briefs. I remember seeing that a few times in the changing rooms at school. Occasionally someone would have a strong enough boner it pushed their briefs out so far you could see right into them side-on through the leg holes. Good memories

[DrWhoFanJ]

CHAPTER 6

Gently creeping up to the helpless boy, Jack gently placed his hands in the air above Shane’s stomach, and then unleashed a rush of tickles that sent him into a giggling, squirming fit. Even through all that, he still maintained the strength to keep his hands firmly placed against his head, so Jack now switched to Plan B.

Moving his hands lower on Shane’s body, Jack now landed on the briefs that were still his only cover, but they didn’t stop there. Now bringing the cotton underwear along for the ride, they continued downwards until the base of Shane’s cock emerged into Jack’s field of vision. Even that was not enough to force a movement from Shane’s head, so he kept going, knowing there must be a point somewhere that would be too much exposure to bear.

Unfortunately for Jack, what he had failed to realise was that Shane’s cock was now so big that it precluded any further movement beyond that point in the tight briefs.

Only now comprehending the flaw in that plan, Jack quickly recalculated and decided to announce that the two minutes had now expired, prompting Shane to hurriedly drop his hands and readjust his undies to a less-embarrassing position.

Unfortunately it was now Shane’s turn to only realise something too late:…

[DrWhoFanJ]

CHAPTER 7

Unfortunately it was now Shane’s turn to only realise something too late: Jack had lied and the clock still had a mere 2 seconds remaining.

As he looked desperately around the room, all he could see on all sides were the laughing faces of his peers.

“Aww, bless. Is 118 seconds all you can bear? Tough luck. No jeans for you and your big boner, Weeny. Guess you’ll just have to hope those briefs of yours don’t break!” teased Jack, guffawing at how perfectly the spur-of-the-moment plan had worked.

“Or maybe you could swap them? Undies for trousers? Seem fair enough to you?”

Realising it was at least better he had his whole lower half covered, even if only by one layer, Shane agreed to the swap.

Carefully lowering his undies (the boner having subsided again from the shame), Shane gingerly exchanged them for the proffered jeans and hurriedly went about getting them up his legs without exposing himself any more than he already had.

“Well, while you were busy doing all that, we were also doing the auctioning for when you failed (as we all knew you would) and the winning bid, at a whopping $250, and now getting these briefs of yours was…”

Everyone (except Shane, obviously!) drummed their fingers on the nearest surface for suspense.

“…James in the middle row behind you! Come down here and collect your prize, young man!”

While James was making his way down through the auditorium seating, Jack thought of another little idea.

“James, while you’re here, if you want, you can also purchase a one-time voucher to make poor Shane here strip butt naked at a time and place of your choosing. Yours for only a $50 extra charge. Whaddya say?”

Now, James wasn’t gay in the slightest, but, having seen how terrified Shane was wearing just his undies (and now commando in rather loose jeans) with a raging boner in them, he saw what a huge leverage these vouchers could have on the poor boy.

“Yes, OK, I’ll get one. So you’d best be on your best behaviour in our science classes, Shane, or I might just volunteer you as our male specimen for biology!”

“Now then, what’s next? Ah, yes, one large school T-shirt with collar. What shall it be for this one, Shane? What are you prepared to do for us now?”

Taking his silence as confirmation of complete submission, Jack announced that, in order to recover his shirt, Shane would simply have to lose the boner tenting his pants within the next 10 minutes.

Relieved at having gotten a simpler task than the previous ones, Shane heaved a sigh of (relative) relief. Unfortunately, he didn’t realise Jack had already planned a very specific form of entertainment for this section that would make even the devoutest of monks struggle to maintain anything less than a semi-hardon.

[DrWhoFanJ]

CHAPTER 8

As soon as the timer started, all the swim team burst from their seats wearing their European-style swimsuits and shimmied alluringly in Shane’s direction.

Only now realising how drastically he’d been snared in Jack’s trap, Shane resigned himself to the fact that he would not be recovering his shirt either. The best he could hope for now was briefs and jumper with the possibility of offering some of his prized possessions for more coverage. In the meantime, he may as well enjoy the performance from all these brave girls showing him their tits and pussies in their long-controversial attire.

Fortunately for him, Jack had a deal planned for the young boy whose jeans were clearly insufficient to contain his regrowing boner, albeit one with an unfair balance against the latter.

Sidling up to him, he opened, “What do you think of our swim team? Hot enough for you? Any favourites?”

Too stunlocked at all the exposed female flesh on display, Shane could only just stutter an answer. “Er, y-y-n-n-no, n-n-not y-yet.”

“Well, I’ll remind you you only had to lose the boner, and there are two ways of doing that, but I suspect only one is possible now. We really don’t mind. Go ahead and touch yourself at this display. I know I’m struggling with not doing that myself!”

Shane looked aghast at the suggestion, but knew he had very little choice in the matter.

What will Shane do now? Which is more embarrassing: being stuck commando in only his jeans for yet another round (assuming they don’t break from the strain of the boner growing inside them), or having to jack off (pun not intended) in front of the whole school just to get his shirt?

Swimsuits from Thornwood series used with permission of Ribeye98.

[Robert Brooks]

Still loving this story! Please do continue soon.
I would definitely say the jacking off option is the more embarrassing one.

[DrWhoFanJ]

Still loving this story! Please do continue soon.
I would definitely say the jacking off option is the more embarrassing one.

Thanks very much for the praise and I will take your suggestion on board. Sorry I haven’t updated the story in a while; college work has been swamping my schedule rather more than I had planned, so my writing has unfortunately had to be relegated to a “when I can find the time” activity. Hopefully shouldn’t be too much longer!