← Back to u/4wardplanning

Long hot summer - part 15

After much pleading and begging Jordan was untied from the table. A solid 4” metal cage encased his cock. All things considered, he thought he’d done pretty well, all he had really traded for a bigger cage was the complete and utter betrayal of his dickhead older brother…and anyway, the dude had it coming.

Who knew sore, aching balls and a 4” chastity cage could make a man feel so happy. Regardless, Jordan counted his blessings and got out of the house as quick as he could, not even stopping to shower Maddie’s cum off his face.

Caleb meanwhile, was racing towards the house. In the past week he’d changed beyond recognition, no longer swaggering around fucking any sizequeen he could find, he was instead struggling to contain his anticipation to strip off at Maddie’s and let her peg his ass. The urge to resist Maddie’s sadistic rules has ceased, his mind was clear, the only way he could cum this month was anally, so dildos were the solution.

After another painfully, horny night, Celeb had plucked up the courage, he was going to ask to use a bigger dildo, and ideally take it home to enjoy it in peace, rather than have Maddie rail him like a cumslut.

“Hey baby boy” Maddie called across the drive as Caleb walked up to the house. He approached her on the front porch, instantly he could tell Maddie had a game to play by the evil grin on her face “how comes you’re wearing so many clothes?” Maddie asked sweetly.

“Err, I’m just in shorts and a vest?” Celeb responded blankly.

“Yeh, you should be naked around me babe” Maddie was deadly serious.

“Umm, Maddie, like” Caleb looked over his shoulder, “you want me to get naked here? Where your neighbours could see?” Caleb hesitated, one hand already moving to pull his shirt off.

“I think little boys should be proud of their cages”

Caleb stripped off his shirt, shoes and socks.

“I’ll just take these to the car for you” Maddie grabbed them out his hands and rushed past him.

“Woah, Maddie, wait” Caleb followed her to the car where she was already dumping his clothes in the trunk.

“Go on baby, these are the new rules. Your clothes stay in the car, shorts too baby boy”.

Caleb was torn, he could just get in the car right now and go home, although she was his key holder…so in the long term a happy Maddie was an easier month…and he really wanted to try out a new dildo. Taking one more look up and down the quiet suburb street Caleb let out a sigh.

“Fine.” In a flash Caleb whipped down his shorts and boxers, threw them in the car and shut the trunk. As the breeze caught his bare arse Caleb realised how incredibly exposed he was, cock stuffed into a 2” cage, his ripe red balls bulging through the ring, instinctively his hands went to his package. A short shake of Maddie’s head confirmed this would not be permitted, forcing his hands to his sides he turned and scurried towards the house.

“Oh babe, it’s such nice weather, why don’t we spend a bit of time in the garden” Maddie called, walking round to the side of the house, where a gate led back to the garden. Flustered, Caleb hurried after her, all the while staring up and down the street anyone who might see him completely naked.

“Maddie” he hissed “ can we please get inside?!”

“On such a lovely sunny day like today? I thought you might want to help me rub some suncream in.” Maddie unlocked the gate and Caleb darted inside. At the back of the house the garden was generally secluded, however, neighbours on both sides would easily be able to see most of the garden from their upstairs bedrooms. On one side lived a Frat house, although it was generally vacant for the summer.

Once inside the garden, Caleb relaxed slightly and spent the next half hour gently massaging suncream onto every part of Maddie’s body she asked for. Soon his cock was pressing painfully against the cage, straining from the near constant teasing of Maddie’s sexy, tanned body and juicy ass.

“Are you hungry babe?” Maddie asked, smiling up at him from the sun lounger. Even though he was, Caleb knew this wouldn’t be a substantial meal.

“Yes Maddie, ass or pussy?” He asked dutifully.

“I was going to say 8” of silicone cock…but since you are being so well behaved I’ll let you eat my pussy like it’s your last ever meal” and with that she laid back and pulled off her bikini bottoms, spread her legs and let Caleb get stuck in. True to instruction, Caleb gave it his all, starting gently and building up, bringing Maddie to climax and back again a second time before she finally called him off.

“What has got into you? You turn up like a perfectly whipped little bitch and do everything I say…you couldn’t have actually grown to enjoy caged life have you?” Maddie questioned.

Caleb knew he had to play the part, let her think he was a changed man and ride out the rest of the month. Then once free he could ditch the act and get back to bachelor life.

“Hah nahh Maddie, it’s just, I’m crazy horny, like, even more so than the last time I let that dildo go up my ass so, umm, I was kinda wondering if we might…try like a different one?” Caleb flushed red, you had to give it to him, 21 years of being a fuckboy and the man knew how to manipulate.

“Awww baby yes of course, I’ll run and fetch one right now and pound you out here in the garden!” Maddie was half way to the house before Caleb had recovered from the shock to speak.

“Here?!” Caleb panicked, “babe I liked the bed last time, it’ll be kinda exposed out here no?”

“I think you liked the bed because you wanted to be tied down and pegged on it, didn’t you?” Maddie said with a glint in her eye, Caleb could see where that was going.

“Can I at least come up and pick the dildo with you?” Caleb almost begged. They stood in Maddie’s room surrounded by her collection of weird and wonderful toys and cages.

“So how many of those are moulded from guys dicks?” Celeb enquired.

“Most” replied Maddie casually, “I don’t really mould anything below 7inch though, so the one you used last time was just shop bought.” She picked up the big black dildo Caleb had fought so hard not to be fucked by last time, the girth was threatening and nearly matched Maddie’s wrist, but the length was probably 7inch exactly.

“I think this ought to do the trick”

Caleb gulped, as much as he wanted to cum, now he was confronted with the hefty cock he didn’t feel quite so keen to get it inside his ass. “Hm babe, remember we need a lot of lube and going real slow?”

Maddie chuckled and reached out to grab his swollen full balls, “aww don’t worry baby, you’re not the first straight boy I’d broken in. Shall I tie you to the bed then?”

Caleb considered, “I think a little sex in the garden might be fun, and the weather is perfect for it right?” Maddie was busying herself with the hardness and screwing the girthy cock into place.

“Fine, but I want your hands cuffed behind your back, if you’re getting fucked by me, you’re doing it like a good slut.” Maddie’s suddenly dominant tone caught him off guard again, the switch in her really was shocking sometimes.

For the second time in his life, Caleb found himself bent over as Maddie fingered his tight hole, lubing him up like her own personal fleshlight. Hands cuffed behind his back and bent over a sun lounger, his caged dick began to leak precum again. The immense girth of the black cock meant it took much longer to get comfortable with the rhythm of Maddie pushing deep into his ass. Caleb tried hard not to think of which local black stud’s cock had been cloned to allow this to happen.

As he loosened up the pleasure began to grow, and as it did Maddie became rougher and more dominant, yanking hard on the handcuffs so his back arched and the dildo slammed hard inside him. She began hate fucking his ass, his little cage swinging wildly with the rhythm of each pound. After 15 more minutes of Maddie’s relentless railing, Caleb’s hair was sore from being wrenched back, twice she’d covered his mouth for so long he’d been pretty sure he was going to pass out.

Despite letting Maddie stretch out his ass to accommodate the girthiest black dildo, he was no closer to coming. The anal orgasm remained just out of reach and soon his body was screaming with the desire to get out of the handcuffs and stop the ass pounding.

————————

At the house next door, Damo was flooded with relief. The anonymous tip off that someone had broken in to their frat house was sus, and whilst he knew it was most likely to be a prank call, he hadn’t been able to resist coming to check on the building. Before he locked the house back up, he did one final sweep of the rooms to check all was well.

Passing through the back bedroom something caught his eye, ‘ooofc the neighbours are used to having the place to themselves huh’ he thought, ‘going at it like rabbits in the garden’.

It was the harness that first caught Damo’s attention, ‘lmao the dude is getting PEGGED’.

Without a second thought, Damo whipped out his phone and started filming, the dude was getting thoroughly ploughed by a chick using a huge black dildo. Damo watched for a few minutes, capturing the roughest bit of the BDSM show in the neighbours garden before posting the best bits on TikTok. He’d even caught footage of the guy running to his car stark naked, nothing but a couple of inches of chastity cage covering a tiny, cut soaked dick.

‘With any luck, that might just make the frat account go viral for the worst walk of shame’, he thought.