Yle's Dungeon Master's a Sissy Boy
Bdsm Story

Yle's Dungeon Master's a Sissy Boy

by Oddlove 18 min read 4.5 (7,100 views)
gay bdsm collar leash sissy boy roommates
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Introduction

Kyle just got to the airport and was taking an Uber home. He took two weeks off work to go visit his hometown and catch up with friends and family, but after two solid weeks of feeling like an awkward alien, Kyle was more then ready to go home.

He couldnt wait to go and hang out with his roommate Cody. Kyle met Cody when he started going to his coworkers house on the weekends to play Dungeon and Dragons. Cody was the dungeon master because he loved coming up with all the crazy ideas and insane plot twists to create intense moments for the players.

Cody had just gotten his two year Associates degree and he was looking for a roommate so he can live closer to the city. Kyle liked Cody's energy and enjoyed talking to him, so he offered to be Cody's roommate. Cody was younger, playful, proudly gay, and into creative things like digital art, photography, and writing. Kyle was a bit older, a closeted bisexual, and into things like pro wrestling, documentaries, and movies.

When Kyle first met Cody, Sure, he thought Cody was cute. But after living together and becoming friends, Kyle was starting to like Cody as much more then a friend. But as far as Cody and everyone else knew, Kyle was a very straight and very vanilla individual. So Kyle decided to keep his feelings and fantasies about Cody to himself. He spent so long hiding from the rainbow that it had become easy for him.

Chapter 1 - Kyle Discovers His Roommate

Kyle spent the whole ride home thinking about Cody, and when he finally got home Cody was at work. While Kyle was putting his clothes away. He stopped and starred at the plastic tote hiding in his closet, hoping that his roommate Cody didn't snoop around and discover his box of shame.

The box that contains things which he's deeply embarrassed about. The box full of his most secret desires. The box that causes him constant anxiety at the thought of others finding it and seeing what's inside. He moved his shoes off the box and lifted the lid to feel a rush of tension leaving his body as he discovered that everything was exactly how he left it.

After putting his clothes away, Kyle went to the kitchen to make a sandwich then went and sat down in the living room so he can watch something on the TV. He took a bite of his sandwich and reached to grab the remote off the coffee table and was shocked at what he saw.

Sitting right out in the open was a thick and heavy leather collar that said "Sissy Boy" along with a chain leash laying next to it. Kyle couldn't believe it, but the it was. Kyle knew he was looking at something Cody would be extremely embarrassed about someone seeing it.

Kyle knew Cody was gay, but he never imaged Cody was into anything... kinky. Kyle didn't know what to do. He didn't know if he should say something or leave and come back after Cody got home and had a chance to put his collar and leash away.

Kyle finished eating his sandwich and thought about it for awhile. He couldnt help but imagine Cody wearing his collar. But kyle didn't have time to sit around and fantasize for long. Cody was going be home soon and Kyle had to make a decision.

Kyle though about it then decided he wouldn't leave and come back in order to pretend he didnt see it. After spending years of his own life hiding his kinks and sexuality constantly worried someone might find out, Kyle didn't want Cody to have to worry about his own roommate finding out anymore. He decided that it's best to let Cody know that he saw his collar and leash, and that it wasn't a big deal.

Just in case Cody was having a friend over after work, Kyle moved Cody's toys to his bedroom and shut the door. then sat back down in the living room to watch TV until Cody got home.

Chapter 2 - Act Casual

Cody was finally home and Kyle was nervious but ready. Cody walked in and shut the door behind him. He saw Kyle on the couch and said "hey Kyle, I forgot you were getting back today. How was your vacation?".

Kyle told Cody all about his vacation and then after they were done catching up Kyle casually mentioned "oh I almost forgot, you left some of your toys in the living room, so I put them on your bed".

Cody didn't seem to know what to say, he appear speachless and embarrassed. After a long pause Cody apologized, but Kyle just responded with "you don't need to apologize, you didn't do anything wrong". Then Cody responded by thanking Kyle for being so chill about the whole situation and went to take a shower and change clothes.

The whole time Cody was showering, Kyle sat on the couch falling into his own thoughts, he found himself confused and excited. He was somehow even more attracted to Cody. after discovering Cody was into some freaky stuff, his mind was running a million miles per hour with ideas.

After taking a shower and throwing on some comfy shorts and a shirt, Cody walked into the kitchen to make something to eat. Kyle wanted to hang out with Cody, and he knew about a new comedy on Netflix. He asked Cody if he wanted to watch it, and Cody said "yeah I'd watch a movie with you, sounds like the perfect way to start the weekend".

Chapter 3 - An Honest Coversation

Kyle and Cody sat on the couch to watch the movie, but Kyle couldn't focus on the movie. He was busy thinking about how Cody had been masturbating in the living room, and how Cody probably even masturbated on the couch they were sitting on.

Suddenly Cody let out a laugh from a scene in the movie, but Kyle wasnt paying attention and missed it. Cody noticed Kyle wasn't laughing during the movie, so he paused the movie and asked Kyle "did I weird you out?".

But Kyle wasn't weirded out... he was aroused. But he wasn't comfortable admiting that. He didn't want Cody to feel awkward about the situation though, so he fessed up and told Cody "you didn't weird me out at all. It was just surprising cause I never expected you had a kinky side".

Cody responded "Well if it's on your mind we should just talk about it. If you're not feeling weirded out about it, then how do you feel about it?".

Kyle explained "I'm just curious about the whole situation. I want to know more, but I wasn't sure if it's appropriate to ask you about it".

Cody let Kyle know that he's willing to answer any questions Kyle has, and that he's okay talking about it. He then explained to Kyle that he actually prefers having an open and honest conversatiom about it just so they can clear the air. Kyle was scared to make Cody uncomfortable, but he got the green light to ask questions, and he was too curious to pass up the opportunity.

The first question Kyle asked was "Do you like wearing a collar for like pet play stuff or is it more about being a slave".

Cody answered "it's more of a slave thing, but I think puppy play would be a lot of fun too".

Kyle asked "how long have you been into the slave/master stuff?".

Cody said "I've always been into it, but I haven't really explored it. My ex boyfriend was very vanilla and he didnt want to do anything like that. So it's just something I fantasize about when I jerk off".

Kyle said "Im surprised your boyfriend wasn't comfortable spicing things up, it sounds like a lot of fun".

Cody explained "Well he didn't mind me wearing my collar when I was servicing him, but he didn't like holding the leash, or the idea of being my master".

Kyle felt a little jealous and mad about Cody's ex. He was jealous the guy got to do such fun things with Cody, and he was mad the guy used Cody to recieve blow jobs but didn't bother giving Cody the space to satisfy his own needs.

Chapter 4 - So Many Questions

Kyle wanted to know more, he had always been into the dominant and submissive dynamics, and he always wanted a friend or partner that likes being an obedient slave who's always eager to please, a slave he could tease and play with, use and satisfy, reward and punish.

He was getting horny just thinking about it and he still had so many questions. So he asked Cody "Are you into other types of BDSM like handcuffs or spanking?".

Cody let out a little smile and said "I'm into most of it, but it's a little embarrassing. So if you want me to tell you about it then you have tell me some of the things you're into first. It's only fair".

Kyle being so secretive and ashamed about his kinks decided he would finally open up a little bit about it, he was talking to a freaky little Sissy Boy after all.

So Kyle told Cody a little bit about the kind of things he was into, stating "well umm.. I really like leather a lot, I've always thought the "Leather Daddy" stuff is really sexy and fun".

Kyle's confession made Cody excited, and Cody replied "Oh Leather Daddys are so hot, it's a shame you're not gay cause that's exactly the type of man gay Sissy Boys want."

Cody continued by asking "is the Leather Daddy stuff something you've done before?".

Kyle answered "I've never told anyone before, so I haven't done anything with it. But I've bought a few leather things over time that I've used while masturbating".

Kyle continued "it's pretty much all I think about though. All my sexual desires revolve around kink and BDSM. it's been frustrating in past relationships because I've had difficult times trying to get excited and stay excited during vanilla sex".

Cody felt the same way, he was unable to get horny or stay horny without at the least thinking about being kinky and getting dominated or punished. And after hearing Kyle express his desire to be a Leather Daddy, Cody couldn't help but imagine Kyle dressed up wearing leather, and he couldnt help by think about how much he'd enjoy being Kyle's Sissy Boy.

Cody was extremely nervious but decided that he would offer his obedience and service to Kyle anyways. Despite being afraid that he might be taking things too far, Cody made his proposal and said "Well if you ever want to play around and have some fun I could be your slave".

To Cody's surprise, Kyle was very receptive to the idea.

Chapter 5 - Cody Surrenders

Kyle told Cody that he would love to play around whenever Cody was in the mood. But Cody didn't want that much control over their activities, plus Cody was always horny and didnt want to overwhelm Kyle with his sex drive. But Cody had a perfect way to surrender that control to back to Kyle.

Cody told Kyle he had an idea, then he got up and went to his bedroom. He came back with his collar, then handed it to Kyle and said "you can hold on to this, and whenever you want to use me or play with me, you can just collar me. And when you're sick of me calling you Sir, you can put my collar away till you're horny again".

Kyle joked "what if I dont let you out of your collar though?".

Cody responded "then I will remain under your power" and he pulled a small bronze padlock and two keys out of his pocket and handed them to Kyle.

A little confused, Kyle asked "why's there two keys?"

Cody told Kyle "one is for my collar, and the other is for my cage", then he pulled down the front of his shorts just enough to reveal a metal chastity device restricting his soft penis from getting hard.

Chapter 6 - Cody's First Proper Collaring

Kyle looked at Cody's chastity device, looked at the keys in his hand, then looked at the thick and heavy leather Sissy Boy collar in his other hand. He felt a wave of heat crashing into his body, then he stood up and walked behind Cody.

He reached around and placed his hand over the front of Cody's throat then ran his other hand down the front of Cody's shorts and began exploring Cody's private area while getting his own hand drenched from all the precum dripping out of Cody's chastity cage. Kyle knew Cody must've been desperately horny for a long time.

Kyle grabbed Cody's collar a wrapped it around his neck, putting the strap through the buckle and pulling it until it was nice and snug. Then he fastened the collar and stuck his finger between the collar and Cody's neck in order to make sure it wasn't to tight.

He took the small bronze padlock and clicked it closed, locking Cody in his collar. While still standing behind him, Kyle grabbed Cody's shirt and starting pulling it up. Cody lifted his arms to let Kyle remove his shirt.

Kyle continued running his hands up and down Cody's body several times before pushing Cody's shorts down and letting them drop all the way to the floor. Then he walked around Cody a few more times admiring his body and thinking about all the fun things he could do to him.

Chapter 7 - Begging For It

Kyle asked Cody "Are you ready to be a good boy?", and Cody said "yes Sir". After hearing Cody call him Sir for the first time, Kyle felt his cock getting hard and pushing up against his own underwear. He lifted Cody's chin up, and as their eyes met Kyle demanded Cody to "bring me your leash".

Cody said "yes Sir", then went to go get his leash. Kyle couldn't believe what was happening, but he had been fantasizing about these kinds of scenarios for so long that he knew it was finally time to put his fantasies into practice.

Cody came back and placed his leash into Kyle's hand, then stood in the the living room fully naked and exposed. Wearing nothing but his collar and chastity device, he was ready to obey all his masters commands.

Kyle then commanded Cody to get down on his knees. Cody got down on his knees and looked up at his master towering above him. Kyle reached down and attached the chain leash to Cody's collar, then he told Cody "I have a special reward for you, do you want a special reward?".

Cody nodded and said "yes Sir", then Kyle informed him "you'll have to earn your reward by sucking my cock to completion. Do you want to suck my cock?"

Cody was so excited to suck Kyles cock, and couldn't wait to find out what Kyle's warm cum tasted like. He's only tasted cum before, but he couldnt wait to taste Kyle's. Ready to finally find out, Cody answered with "yes Sir, I want to suck your cock".

But that wasn't a good enough answer for Kyle.. he tugged on Cody's leash and demanded "you better to ask nicely then".

Cody said "Sir, may a please suck your cock?"

Kyle responded "you will need to ask more nicely then that"

Cody tried again, asking "Sir, may I please suck your cuck and swallow your cum?, please?"

Kyle thought that was pretty good, but he was getting too much enjoyment. He wanted to see how desperate Cody really was and how bad Cody wanted to suck his masters cock. So Kyle told him "I'm not convinced, if you want to suck my cock you're going to have to beg me".

Cody never begged for anything before, it's was so embarrassing and shameful. But he had locked himself into chastity several days ago, and now Kyle was the only one who could let him out. Having not cummed for days, Cody was so horny and hungry for cock that he was willing to beg like a pathetic little Sissy Boy until he got what he wanted.

He looked up at Kyle and started begging for it, saying "Sir, may I please suck your cuck? I want to suck your cock so bad, I promise I'll be a good boy and swallow all your cum. I'll lick it clean afterwards. Please Sir! I'll do anything you want".

Kyle chuckled, and was amused and satisfied with Cody's begging. Looking down at his desperate Sissy Boy, Kyle said "you may suck my cock".

Chapter 8 - Service

Cody stared at Kyle's bulge for a moment, then looked back up, and Kyle reminded him "I gave you permission to suck my cock".

So Cody took a deep breath, then nervously reached forward and slowly unbuckled Kyle's belt, unbuttoned his pants, and unzipped his pants. Cody started pulling down Kyle's pants, exposing the shaft of Kyle's penis. He pulled down a little more and Kyle's half erect cock flopped all the way out.

Kyle's cock was covered and dripping with precum just a few inches away from Cody's mouth. Cody was salivating to the point of almost drooling. He did want to rush, but he couldnt wait any longer. He leaned in and opened his mouth, putting his lips around the tip of Kyle's cock and begin sucking on it.

It tasted even better then Cody though it would. Cody spent a little time enjoying the tip. When Kyle said "you like having my cock in your mouth huh", Cody didn't want to stop sucking Kyle's cock so he looked up and nodded, mumbling "mm-hmm".

Cody could feel Kyles cock growing bigger in his mouth and he desperately wanted more. He placed his hands on Kyle's outer thighs for leverage, then he opened his mouth as wide as possible and began shoving Kyle's cock all the way in. Cody gagged a when Kyle's cock pushed against the back of his throat, but Cody could see that Kyle was enjoying it.

Cody was having amazing experience gagging on Kyle's cock, but Kyle had ideas of his own so he pulled his cock out of Cody's Sissy mouth. Cody looked up wondering why Kyle stopped him and Kyle leaned over firmly gripping Cody's throat, then he gently slid two fingers into Cody's mouth and began pushing them in and out, going deeper and harder each time.

Gagging on Kyle's fingers, Cody was struggling to keep his mouth open. He was fighting the instinct to pull away because he didn't want to disappoint his Master. After a few minutes of fingering Cody's throat, Kyle slowly removed his fingers.

Cody remained on his knees looking up at Kyle with his mouth wide open like a good boy, so Kyle leaned in and let his saliva slowly drip out of his mouth into Cody's mouth. But Cody didn't swallow it. Kyle realized Cody was waiting for permission to swallow, so instead of giving Cody permission to swallow, he spit into Cody's mouth two more times.

Kyle ran out of saliva so he ordered his Sissy Boy to swallow. Cody closed his mouth and swallowed it all in one gulp then opened his mouth to show it was all gone. Afterwards Kyle removed his pants from around his ankles, walked over to the couch, and sat down.

Tugging on Cody's leash, Kyle simply said "come" and Cody crawled on all fours to his master and waited for his next order. Kyle said "you're not done, finish sucking my cock".

Cody grabbed his masters cock, inserted it into his mouth, and began sucking and stroking it. Kyle reached down and removed Cody's hand, telling him "just your mouth". Cody was more then happy to obey, he knew that it would take Kyle longer to cum if he couldnt use his hands, and Cody didn't want the fun to stop.

Kyle put one hand on the back of Cody's head, guiding him and slowly increasing the speed while shoving his cock in a little bit deeper each time. Eventually Cody started to struggle again, but it only made Kyle more excited. Cody was struggling pretty bad and instinctively put his hands on Kyle's thighs and pushed away. Kyle stopped for a moment while Cody caught his breath.

Then Kyle asked Cody if he's needs a break. Cody said "I want continue Sir, I'm sorry I used my hands, I just need to get wrist restraints for next time". Kyle was surprised by Cody's willingness to struggle for him. It somehow made Kyle even more horny than he already was.

Before continuing to fuck Cody's throat, Kyle came up with a solution for for both of them. He pushed Cody's head to the ground and ordered him to stay. Cody heard Kyle set his leash down and get off the couch. Then he heard Kyle fumbling around with his pants. Cody was worried Kyle was disappointed that he push away after choking on Kyle's cock.

Just as Cody was starting to over think it, Kyle grabbed both of Cody's arms and pulled them behind his back. Then Kyle bound Cody's wrist together with his belt. He walked back around and sat down on the couch. He grabbed Cody's leash and pulled him back up.

Kyle told Cody "I'm going to be really rough with you and make you gag and choke on my cock until I'm finished", then he asked Cody "Do you want to continue?".

Cody, without hesitation, responded "yes Sir".

Then Kyle said "you've been a really good boy today, but before we continue, I'm giving you a safe word. If you want to stop, you say the word.", then he asked "Can a trust you to use your safe word if you need me to stop?".

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