Road Ahead Pt. 01 - Chastity Road

Hey everyone! This story is meant to be the first of many chronicling a young man's unintended chastity journey. It's mostly background info and setup to the upcoming parts, which I will try to be more consistent about posting. If a background story doesn't interest you, this may not be for you.

I've enjoyed writing this for you (admittedly while locked in chastity myself) and I love receiving feedback on my stories. Go easy on me! Feel free to respond to the question at the end. Who knows, you may influence future parts. ;) You can reach out via my profile!

Happy reading!

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Eric watched the delivery guy stride away, still processing everything. He turned and closed the door, holding the package in his hands. There it was -- addressed to him and all. He had spent so much time preparing for this -- the shaving, the measurements, the re-measurements. Every specific detail counted and needed to be perfect. And now it was finally here.

No time was wasted as Eric made his way to the kitchen and sliced the box open, tearing out his new ChastiBoy device. He had been so frustrated with past attempts at chastity where the cage was too large or too small or the ring didn't fit right or...insert endless list of chastity-related issues here. But this one was going to be different -- he spent so much time perfecting every single measurement so that this one could be -- no, would be -- perfect.

He opened the ChastiBoy box for the first time and placed inside atop the device was a 'WARNING' card. It read, 'Warning: For the chastity wearer seeking an enhanced chastity experience. Be cautious of connecting this device with online chastity software as...' "Blah, blah, blah," Eric said as he haphazardly tossed the warning card after barely glancing at it. "Who reads these things?" Eric exclaimed. He could hardly contain his excitement and giddiness at opening up what was sure to be his new favourite toy.

Eric hadn't always been into chastity, but it was an encounter a few years ago that he'd had with a guy online that had piqued his interest. He was still relatively new at kink and was cruising around the apps with a profile that had said 'sub looking for Dom man,' to which he had received a few replies. One in particular was from a guy named Tom, who had calmly explained that he'd like to be Eric's dominant. He would feminize him a little bit: chastity (short-term moving to longer moving to permanent), no hair other than on the head and the eyebrows/lashes, and some women's clothing under his regular wear (panties mostly). Eric had chickened out because he was still new, and he didn't like the idea of being feminized. He began to research chastity devices though, as it had intrigued him. He didn't realize that in that moment, the seed had been planted and he would be a chastity boy. Once the researching starts, it's only a matter of time before the lock clicks.

Eric carefully unboxed the device and basked in its beauty. The device was a gorgeous, sleek, and shiny black plastic with a nicely curved ring base and small LCD screen on the front for electronic control. The device had small openings throughout for cleaning potential, though Eric preferred the remove and replace-once-cleaned method. The LCD had two layers of tempered glass for protection and a charging port on the side, and was removeable for when the wearer needed to shower or be anywhere near water. Eric removed the LCD screen from the device and attempted to open it, but it was locked shut. "What the fuck? Why did they send it locked?" he said, mildly irritated. The locking mechanism was on the inside, behind the plastic cover once the LCD was removed -- there was no way to pry the lock open. He opened the instruction manual, which explained on the first page that to unlock the device, the initial setup needed to be complete with the app. "They don't want idiots like me locking it on with no way to remove it," he laughed.

After reconnecting the LCD screen to the device, Eric plugged it in to charge and began to lazily flip through the instruction manual. "Seems simple enough," Eric said taking out his phone and searching for the 'ChastiBoy' app and beginning the download. The new app appeared brightly on his phone screen as an unlocked padlock, under which the name said, 'Secure,' which made it look like a password storage app. "Nice," Eric said opening the app.

'Welcome to Chastiboy!' was the first message, alongside the 'Over 18' necessity. The warning from the warning card popped up almost immediately after and Eric dismissed it faster than the first time. "What are all these warnings for? Like guys don't know what they're about to lock on themselves?" Eric selected the option for setting up a new device and chose the pairing option. The LCD lit up with the same logo as the app and confirmed the pairing via similar codes in the app and on the LCD screen. Once the pairing was complete, the app updated to show all available options for Eric's new toy.

The main layout was very simple -- it was a list with all of the options available. At the top, there was a locked padlock, and when clicked, the symbol unlocked, and the LCD on the cage lit up showing the same unlocked symbol. Eric attempted to take the cage apart and it worked! "Cool!" Eric said. He replaced the cage and clicked the symbol again, locking the device shut. The page had some useful information such as the battery life of the device, which was already 97% charged and a few other settings Eric wasn't overly interested in at the moment. One that caught his eye was 'Vibration Settings,' which was toggled off. Eric toggled it on, at which time the device vibrated three times on the counter. "Damn! They thought of everything." He adjusted the limits to the maximum, meaning that he could set it to vibrate as lightly or as fiercely as he wanted while wearing. "That could be fun for edging and stuff."

He didn't bother to search through the rest of the settings because he was so eager to check the actual fit of the device. Unfortunately, he'd already gotten a little excited at playing, so he needed a nice shower to calm his dick down just a little.

After a nice, but slightly cold, shower, Eric did a very quick once-over of hair removal cream to pick up any strays in the area. He applied lotion to his dick, his balls, and all the surrounding area before beginning the process of putting on his newest toy. He slipped his balls through the ring, which he noticed was a very comfortable fit. With a thin sock, he was able to get his dick situated nicely in the new cage, which was also very comfortable. Everything was a nice fit -- nothing felt too tight, but it was clear he would not be given any growing room in this cage either. "This is the best fitting cage I've ever put on!" Eric said admiring the fit of everything. He took his phone, opened the 'Secure' app, and clicked the little padlock to lock the device in place, which it did immediately. The device vibrated strongly three times and showed the locked sign on the LCD. "Fuuuuuuuck," Eric moaned as a small drop of precum formed at the tip of his now locked cock. He noticed that the app recognized that he was now actually wearing the device -- it didn't vibrate from being locked before.

Eric threw on a loose pair of sweats for lounging around and when he put them on, the device was only slightly bulging out, but was otherwise unnoticeable. He went back to his laptop in the living room to start cruising the online chastity sites. Obviously, he already had a profile, but it needed a little updating. He opened the settings for his profile and started to make a few adjustments given that it was mostly blank. Eric began selecting all the options to update his profile, "Gender? Male. Age? 31. Role? Wearer. Submissive. Holder Preference? Male." He updated his location down to the city. "Hopefully there's someone close to me," he wished aloud. "Device? ChastiBoy." With this selection, a new option appeared saying, 'Link ChastiBoy'. Eric was curious, so he selected the option, which asked for the device serial number, which he was able to get from the app. The device vibrated on Eric's locked cock twice and Eric pulled it out of his pants to see, along with the leaking from the tip, that the device had successfully linked with his profile. "Nice."

Eric's locked dick was straining in its prison quite nicely and he immediately noticed that there was no uncomfortable tug at his balls or feeling of pinching or circulation-stopping squeezing anywhere. It was a perfect fit. "All that time spent measuring was worth it," he said, relieved that it was actually fitting well.

Eric wasted no time in his newfound not-freedom looking through potential locks to make the lock more official. "These people are fucking crazy. Like, seriously, who actually locks up in these holds with no time limits set?" He set the settings to look for people in his general area and the surrounding areas. "Maybe I can find someone close by who isn't a fucking psycho." He loaded the search with the new area settings and the sessions popped up immediately, which Eric began to open and read.

Session: I AM YOUR MASTER

Description: BOW DOWN BEFORE YOUR MASTER SLAVE!

Initial Duration: Random -- 60-90 Days

Time Limit: None

"Nope."

Session: It's How You Belong

Description: We all know that the best cock is a caged one. Just a locked guy here helping other guys keep that cage on. You know it belongs there anyway, so why wait?

Initial Duration: 3-5 Days

Time Limit: 2 Weeks

"It's not a bad lock...could be fun..." Eric started before moving on. He viewed the profile of MysteryMikey. "Wearer." Eric didn't want another sub to lock him -- it needed to be an actual keyholder.

Session: A short lockup

Description: Don't check here often. Idea is if I catch you in the lock in the first 24 hours, I'll extend the timer and you'll be locked for as long as I say.

Initial Duration: 24 Hours

Time Limit: None

"Short lockup my ass. It notifies you when someone joins your locks," Eric said rolling his eyes.

Session: Sissy Training

Description: You'll be the best sissy you can be when this session is done. Lock will last around 30 days for full training with tasks. Maybe longer.

Initial Duration: 30-120 Days

Time Limit: None

Eric thought about that Dom that had wanted to feminize him that originally got him interested in chastity. His cock strained in its prison.

Session: Dream Come True

Description: Make sure to read EVERYTHING before accepting this session.

Eric looked at the description, which he was sure was longer than some books he'd read. "Shame." Initial time of 3 days and max of 7." He moved on not wanting to turn his chastity session into study hall.

Session: Time to lock up

Description: Upon accepting this session, transfer $50-

Eric didn't bother continuing to read. He knew that financial domination was for some people, which he respected, but he wasn't one of them.

Session: Chastity Road

Description: Please be sure to read what's written here. I have no interest in holding for someone who doesn't bother to read and then messages me to tell me they want the exact opposite of what I'm offering.

The description was detailed, but at least it wasn't a novel. Eric read through.

This session is designed to meet you where you are, so it will be different for different people. I am VERY communicative, so please don't sign up for this session unless you are open to communicating a few times daily. Also, if we're near each other, I'd love to take this virtual session and add some non-virtual components. Make no mistake -- you will feel dominated by me during this session. You will remember who owns your caged dicklet and will be leaky and horny for the full duration.

There can be games set up with all of the normal stuff and a bit of the abnormal stuff: add time, subtract time, pillory, tasks (your choice or mine), extra verifications, etc. I can also set up tasks to either play further into the horniness -- hole training is important for any good boy. Need to make sure you can take any size in any way any time for when a man wants to use you. He might want you to go slowly up and down the full length of his manly cock while you live in the ecstasy of frustration, or maybe he'll want to use you roughly or have you deepthroat him longer and longer until you're gasping for air. Maybe he'll tie you up and use your ass or maybe he'll have you fuck yourself on him trying so hard to hit that spot just right for the chance to cum from being used. Trust me, you'll be begging to be used with how horny you will be. ;) Tell me about your toy collection. You will be required to verify daily at least once and upon request -- I don't care where you are or what you're doing. Everywhere has a bathroom. You will have to earn hygiene releases -- I don't like the idea of you unlocked with no supervision. Prove to me I can trust you. Other settings we can play around with. Feel free to take a drive on chastity road, baby boy, and who knows? You may never want the ride to end.

Eric sat there, stunned in silence, leaking profusely and straining quite clearly in his cage, which still sat outside his pants. "Fuck," he mouthed breathlessly. "It's perfect. I mean, I'll have to see how much wiggle room there is on that hygiene thing. Can't go too long without washing. How long-," but Eric stopped as he read:

Initial Duration: 3 Days

Time Limit: None

"Of course. No time limit. What the fuck is wrong with the people on here thinking of having people lock up with potentially no chance for unlocking? I don't want to abandon any sessions," Eric said slightly annoyed. "For once, I'd like something realistic!" What frustrated him more was the fact that he was so horny for this session. He was leaking and straining like crazy reading through everything, but without the time limit, it didn't matter. He opened up the profile of the holder 'DominAnthony' and looked through it. "Male holder...seeking submissive boys...34 years old...lives in my city!" The green dot next to his profile name..."He's online! I'll shoot him a message and see if we can just fix up a few details."

Eric opened up a new message. "Here goes," he said as he began typing.

Subject: Hey

Message: Hey! I'm Eric. I saw your chastity road session and was straining in my cage just reading the description. I love everything about it -- the games, the tasks, using my holes, and verifications. And we're in the same city! I'd definitely be down to meet and see if some of that hole training could be a little more pleasurable for you...;) I was hoping to chat about the time limit and hygiene thing though. I need to remove my cage daily for a shower at least (I promise you can trust me!). Also, can we set a max time on the session? Like 30 days? I don't feel comfortable with sessions with no max time limit. Only willing if we can make those changes -- let me know, seems like we'd have fun. Eric

After sending the message, Eric went back to look at the session again. He was transfixed, his mouse hovering over the 'Adopt Session' button where another option appeared, which read, 'Accept session by tapping the green checkmark on your ChastiBoy device.' He looked down for the first time and realized a large green checkmark had appeared on the LCD of his device. His cock leaked tear after tear of precum onto the front of his track pants. He hadn't even noticed that for all the sessions he was clicking through. "Fuck," he laughed. "I better be careful -- one mis-click and I'm doomed."

The front door suddenly opened. "Yo! You here, Eric?" Eric heard footsteps moving toward the living room where he was sitting. He forgot his best friend Mike was coming over to pick up some camping gear! They had stopped knocking on each other's doors back in high school and Mike even started calling Eric's mother, 'Mom.' They'd been best friends for almost twenty years.

"Shit!" Eric whispered. He quickly put his hand over the device to grab it and shove it back into his track pants. He tried to quickly rub the precum off the front of his pants. "Thank fuck these are black," he whispered as Mike rounded the corner.

"Woah!" Mike jokingly yelled throwing his hand over his eyes, but making sure to leave peeking room in between his fingers. "Am I interrupting something?" Mike asked looking through the gaps in his fingers and suggestively raising his eyebrows.

"Fuck off," Eric said closing the laptop. Just then, his device vibrated strongly twice, eliciting a small gasp and some precum from Eric. Mike pulled his phone out to check it but put it away just as quick.

Mike looked pointedly at Eric's unknowingly locked cock, which appeared only as a large bulge under his pants and said, "I know a little fun when I see it," raising his eyebrow. "Guess we're even now," Mike said using his smuggest voice.

Mike was referring to the time Eric had walked in on Mike changing and his dick standing at full attention. That time, they both froze and Mike looked down at his fully erect cock, looked up at Eric, and said with all the confidence in the world and as if he wasn't straight as an arrow, "Guess he likes you!" Since then, Eric made a point of making as much noise as possible when approaching Mike's room -- just in case.

"Yeah. This is completely the same as me being stared down by your hard-on," Eric said laughing. He wasn't embarrassed -- they moved past being embarrassed around each other a long time ago. He was admittedly relieved that Mike thought he was just jerking off. For a second, he was worried Mike had seen his dick all caged up. They'd seen each other naked before having changed in front of each other, but this was different. Mike was like a brother to Eric and he wasn't sure he was ready to have the 'this is a chastity device so I can surrender control of my dick to another man while not being able to cum or even get hard,' conversation.

"Come on! Slamming your laptop shut on me? Not cool bro -- share the love," Mike suggestively teased. Eric took the bait.

"You wanna come cuddle and watch a guy choke on another man's big...meaty...veiny...juicy cock?" Eric said slowly emphasizing each word.

"No need my friend," Mike said confidently. "I have lived experience with girls doing it in real life all the time. Much better to feel it than watch it," he said winking at Eric.

"Like I said, fuck off," and they both laughed.

He was really thankful for his friendship with Mike. Eric had been worried to come out to Mike and lose his best friend -- it was honestly harder than telling his parents. It was years ago but he remembered it clearly. Mike was in the process of talking about his latest sexual conquest describing every detail in horrifyingly vivid detail, "Just close your eyes and picture her just bucking up and down bro. Let your dick-," "I'm gay, Mike," Eric had said before he could stop himself. Without missing a beat, Mike continued, "Then picture the hottest guy you know just riding you like a fucking bull man. Let your dick whisk you away." And that was it -- he had his best friend still.

"The camping gear's in the hall for you," Eric said moving toward Mike.

"I get it man," Mike said turning with him, "You wanna get back to your imaginary friends," he said matter-of-factly while making a jerking off motion with his hand. Eric rolled his eyes.

"Let me help you get this shit in your car," Eric said grabbing some of the gear and walking it out to Mike's car. Between the two of them, it was only one trip.

"Thanks man. Sure you don't want to come?" Mike offered again. "I'm sure we can find a sexy guy in the woods to choke on your-"

"NO!...thank you," Eric cut him off getting a laugh from Mike. "I..." Eric started but got stuck on that one letter as his cage strongly vibrated one single time. It was drawn out this time and felt like it lasted an eternity. He focused all his energy at not letting his eyes roll back at the sensation and trying not to let the river of precum through. Mike checked his phone again as the vibration stopped.