Gay Chastity Story
I was just about ready to delete my profile on the dating app when he messaged me.
I’d been active on the app for nearly a year, but in that entire time, I’d only gotten a small handful of dates. Even though my profile said “Reasonably Attractive Blonde Twink,” and was filled with flattering photos, mostly selfies I had taken in my free time, I just couldn’t catch anyone’s attention.
Well. I guess it was more that I couldn’t catch the kind of attention I wanted.
I was a natural submissive, had been since puberty. My tiny cock, barely over an inch long, thin, delicate body and curly pale blonde hair gave me the look of someone who was meant to serve on his knees. And I was certain that that was my purpose – to be someone’s perfect and ideal, completely obedient sexual slave.
I didn’t just want to be dominated for one night in bed. I wanted it to be my permanent lifestyle. I would do absolutely anything for a big, strong dominant Master who mixed kind treatment with cruel punishments as I served him every single day of my life.
And then he messaged me, and I got my wish.
His screen name was simply “Master L.” His profile was mostly pictures. Selfies, photos of him at the gym flexing his enormous muscles, even a few photos when he had just gotten out of the shower, his mane of spiky brown hair plastered to his muscular back by the water. Aside from the pictures, there was one simple statement: “Dominating Master looking for a permanent slave”.
He was perfect.
And he knew it, too. His first message to me was a nude photo, specifically a selfie. His muscles looked even more impressive up close. His cock was enormous – easily eight inches longer, and girthy too. It was longer and thicker than any toy I had ever had in my ass before.
His message was just like his profile. Short and to the point. It said:
“You’re looking for a master. I’m looking for a slave. But I have one condition. If you are to become my slave, you will spend the rest of your life locked up in permanent chastity.”
A shiver ran through my pale, lean body as I read Master L’s message over and over again. I’d heard about male chastity, of course – I’d been single for years, so my sex life mostly consisted of browsing the Internet for Dominant and submissive porn. But I’d never even considered trying it out for myself.
Despite my trepidation, I agreed to meet him.
Master L knew exactly what he wanted. He didn’t even delay things by setting up a date at a restaurant or the movies. He gave me his address and told me to meet him there in three days, at noon, wearing my laciest and frilliest pair of underwear.
Three days later, I was there. He lived in a luxurious penthouse apartment in one of the tallest skyscrapers in the city. Even in my nice suit and pink tie, I felt underdressed. Only the pale pink silk underwear decorated with frills, hidden beneath the layers of my outfit, felt fancy enough for this environment.
That turned out to be a good thing. I had barely entered the living room of his huge apartment when Master L commanded me to strip down to my underwear. I hurriedly complied.
“Acceptable,” he said with a lecherous glance at the frilly pink panties.
“Thank you, Sir,” I responded, instantly slipping into my role as his slave and submissive.
While I was only in my underwear, Master L was still fully dressed. Not that that meant he didn’t make an erotic picture to look at…because he most certainly did. He was wearing a tight button-up shirt in a deep crimson red and perfectly cut black slacks. I could see his every muscle clearly defined through the thin fabric. When he turned around to close the blinds on the living room windows, I could see that his ass was firm enough to rival a porn star’s.
“Did I say you could look, slave?” he growled. His commanding voice sent shivers down my spine.
I shook my head. “No Sir.”
His only response was another order: “Get on your knees”. Of course, I obeyed instantly.
The room wasn’t carpeted. Within seconds, my knees were in pain. But I didn’t move.
Master L stalked around me, moving in small, tight circles as he observed every part of me like I was a prize-winning cow. He roughly grasped my chin with his tanned, calloused fingers and pushed my head from side to side. He ran his hands up my thin arms and legs and over the flat planes of my stomach. He tugged on my blonde curls and I had to try not to mewl with arousal. This drew a low, dangerous chuckle from his lips. I wondered for the first time if I might be in over my head.
Finally, after what seemed like an eternity of examining the rest of my body, Master L placed a single finger on the wet spot that had formed on the front of my panties. He smirked, clearly knowing that it was his touches and his commands that had caused the spot to appear in the first place.
“You follow orders well, slave,” Master L told me, and a flush of pride ran through my body at the compliment. However, he immediately followed it up with a reprimand: “But your cock doesn’t.”
Without warning, he reared back and struck one of my silk-covered ass cheeks with his bare hand. “Did I say you could get hard, slave?”
With the third smack, I couldn’t resist crying out in pain. Luckily, he didn’t smack me again, just laughing again – that low, dangerous chuckle of his that I could already tell meant I was in for something equal amounts erotic and painful.
“Well then, we’re just going to have to train it, aren’t we?” Master L didn’t give me time to answer. Instead, he gave me another command: “Stand up, slave.”
I stood. Without warning, he roughly grasped the waistband of my panties and pulled them downwards. With one single tug, they fell to my ankles, leaving my round, red-marked ass and tiny cock on full display for his discerning stare.
To my surprise, Master L laughed again. He pinched my cock between two fingers of one of his massive hands. It was barely the size of one of his smallest fingers. “My, my, slave, I’ve fucked a lot of subs over the years since I first became a Dom, but you have absolutely the smallest cock I’ve ever seen! It’s like a little sissy boy clit! It’s absolutely pathetic!”
He pinched it tightly, causing another drop to leak from the tip. “From now on, slave, this cock belongs to me. Do you understand?”
“Yes, Master.” Already the words came as naturally to me as breathing.
“Your pitiful little cock will be locked up in a chastity cage. Lucky for you, I happen to have one in my collection small enough to fit you. You will be allowed to remove the cage once per week for cleaning, but that’s it. You will no longer be permitted to masturbate or reach orgasm from having your cock stimulated. Do you understand, slave?”
I nodded, the mix of nerves and arousal forming a lump in my throat that made it impossible to sleep.
“I will promise to keep you safe and healthy and not permanently damage your body in any way. In return, you will promise to be completely obedient to me for the rest of your life. You will also turn over possession of both your body and mind to me. I will decide everything about your life, from what you eat to what you wear to how often your slutty little ass will be taking my cock. Do you understand? Later, I will prepare a contract for you and I to sign, but for now, I want a verbal agreement from you. Do I have it?”
“Oh, yes, Master.” I knew I should leave it at that, but it was like I physically couldn’t prevent the words from bubbling out of me. “Oh Master this is what I have waited for for so long. I was born to be a submissive slave to someone Dominant like you.”
My ass received another smack, still on the same cheek as before. Forget red marks – by the time we were done, I was going to have a full black and blue bruise that would take days to heal! “I’m glad to hear that, slave, but you need to learn not to speak unless spoken to or expressly granted permission. Are you going to be a disobedient little brat, or a good slave? You may answer.”
“Good slave! Oh Master all I want is to be your good slave!” I bowed my head, not making eye contact so as not to make Master L any angrier than he already was.
He gripped my shoulder tightly, leaving yet another set of marks, this time in the shapes of his individual strong fingers. “Very very good. Now, come with me.”
He led me into what had to be his bedroom. It was just as lavish as the rest of the apartment – the bed was a full king size, with plush covers and an entire pile of pillows. Of course, Master L did not lead me to the comfortable bed. Instead, he roughly raised my hands over my head and tied them to a hook set in the ceiling.
It was far from comfortable. I could still stand, but just barely. I had to stand on my tiptoes while I desperately struggled to keep my balance. I realized that Master L had probably had many other slaves tied to that hook. I doubted I was far from the only man he had introduced to the pleasures of being his chaste slave.
Master L walked in front of me so I could see the small object that he was holding. It was a pink chastity device, made from hard silicone. It had a shape that made it obvious it would cover my entire cock, except for a narrow slit which would allow me to pee normally. I would not be able to touch a single bit of my tiny little penis once I was locked into that cage.
My new Master did not need to kneel to reach my tiny cock. Still standing proudly in front of me, he began to rub thick lubricant all over my cock and balls. “Putting on the cage for the first time can be uncomfortable,” he told me. “This is one of the few bits of mercy which I will show you, so you’d best appreciate it, slave.”
“Thank you Master.” I responded.
Slowly, he began to slide the ring at the base of the cage over my balls. The silicone was cool, but not uncomfortably so. The feeling of tightness around my sack was perfect. I loved it already. I knew that this was what I had been missing my entire life, why I had never felt sexually fulfilled until today. It was my destiny to be a sissy chastity slave to a dominating man like Master L.
“I can’t keep calling you ‘slave’ forever,” my master told me. “I think I’ll give you a new name, to mark the day that you became my chastity pet. How about…Hmm. “N”. It stands for nothing and nobody, to remind you that you are nothing without your Master. Do you like that, N?”
“Yes, Master!” I responded eagerly, gladly accepting my new name. Already, I felt all memories of my old name slipping away. It was like my master had stolen it simply by assigning me this new one. From now on, I would be “N” forever.
“Get ready, slave N,” Master L warned me as he slipped the body of the chastity device over my tiny cock. I was so small that the device slid on easily, covering up every bit of my miniscule length. I knew that for the rest of my life, I would only be granted the honor of touching or even seeing my cock when my Master allowed it.
I heard a click as he fastened the old-fashioned metal padlock which held the cage closed. It was done. I could not escape. The weight hung, unfamiliar but secure, against my legs. I knew that, with my pitiful strength, I could not break out of the cage even if I wanted to.
Master L threaded the small golden key through a chain and fastened the chain around his neck. I understood what that meant. Every moment for the rest of my life, I would be reminded of his control over me. I would be reminded that my cock – and the rest of me – belonged to him.
“Chastity will be good for you, slave,” my Master informed me, still without untying the bonds that held my wrists suspended high above my head. “It will teach you to become perfectly submissive and obedient. You will learn to fulfill my every whim as quickly as possible if you want to have even the slightest hope of getting an orgasm. But soon, as I train you in the proper ways, your libido will shrink and your sexual desire will decrease. You will no longer crave orgasms of the ‘traditional’ kind and will instead long only to have your prostate milked or your orgasm ruined. Your only sources of pleasure will come from taking my cock and my toy collection, or being punished by me. Do you understand?”
I nodded, too overwhelmed to speak. My tiny cock twitched inside its new home, but nothing else happened. Every word he was saying was turning me on more and more, but I couldn’t do anything about it. Just like he had said, the cage didn’t only prevent me from coming, it prevented me from getting an erection entirely. The cock inside that cage didn’t even belong to me anymore. I belonged to him.
“Very good, slave N. You’re learning already.” Giving my cage an affectionate pat, Master L walked around me until he was facing my pert, round behind instead. He began rubbing the cheek that he had slapped. My hole twitched with anticipation of what was coming next.
“Now, let’s find the perfect butt plug and get started with your training, shall we? Your ass is pathetically tight. You look like you could barely take my finger right now – but you have two weeks to be able to take my cock without whining or moaning if you want to have even the tiniest chance of earning an orgasm this month. So you’d better get started right away, shouldn’t you, slave?”