Chase's Dive into Chastity Ch. 01

I awoke to the harsh wailing of my morning alarm. With groggy annoyance I rolled over and switched it off. I had the urge to just cover my head with my pillow and go back to sleep but something kept nagging at the back of my mind as i lay there eyes closed. Whatever. Just ten more minutes.

Have you ever had that feeling of worry even when you are asleep? The worry you had forgotten something or someone important so you just drift restlessly in and out of consciousness never quite able to come to a completed thought? That's what i was going through until all of a sudden it hit me. I had my first day of training!

"SHIT!" I exclaimed as i suddenly bolted out of bed and checked the time. It was about 10:30 and I was supposed to show up as Ash's house at 11 sharp. I hurriedly threw on some clothes and brushed my teeth. I combed my hair the best that i could but it was still slightly messy. I didn't have time for food so i just grabbed a bottle of water from my fridge and headed out the door.

I was nervous as i sped down the street and turned onto Dogwood drive. This was a serious date I had and being late on the first day would surely land me in a world of shit with my new Dom. His name was Ashery. Ash for short. We had known each other our whole lives but not until recently had I told him how I felt about him. I had been scared shitless for years about losing him as a friend but i really loved the guy and it was torture holding in my feelings. The thing he had managed to keep from me all those years though was that he was into the D/s lifestyle and at the time i had no clue what that was. After some talking and reading a few articles online, i realized the thought of being a submissive scared and excited me. The thought of pleasing Ash made me happy so we had talked and discussed my limits and his and set up a day of training and setting up some rules.

I didn't really know what to expect as I pulled into the driveway. I glanced at my watch. It was 11:05. Well, it was only 5 minutes. Maybe he wouldn't notice. I pulled the keys out of the ignition and fumbled with them to get my door to lock. I made my way to the door and as i lifted my hand to knock the door swung open. The tall raven headed boy that stood before me cast his disproving gaze down at me.

"Hey man, how's it going?" I tried to sound nonchalant but I could tell he wasn't happy.

"You're late Chase. I told you 11:00 sharp." His tone was stern and i shifted uncomfortably as his gaze seemed to pierce through me.

"I'm sorry, I sort of overslept." I said in a soft, apologetic tone. His expression shifted to a lighter form of annoyance and he sighed.

"It's okay, but next time I expect you to be here on time or else there will be consequences for your actions."

He invited me inside and I shut the door behind us. His house was pretty warm and inviting all things considered. He lead me through the living room to the kitchen and on the counter was a black chain choke collar with a little pink tag hanging from it. He smiled coyly as he handed it to me. The text on the tag read "Ash's toy"

I couldn't help but shyly smile as my cheeks flushed. It felt heavy in my hands and was cold to the touch.

"I want you to strip right now. Strip and put on your collar. But just know the moment you decide to put that chain around your neck you are not allowed to take it off yourself. It is a symbol that you are mine and mine alone and you will do as i say for your pleasure and my pleasure as well as your safety. You are relinquishing all your power to me to take care of you and your needs and that is not a light commitment. Do you understand Chase?"

I thought about it only a moment before I nodded in agreement. I was ready for this. I wanted this. I could also feel my cock already straining against my jeans which I was sure he noticed. I shyly removed my shirt and then pants and after a moment or two my briefs. I then handed him the collar insisting that he put it on me. He fastened it and stepped back smiling. I felt my face flush at his pleased expression.

"Alright then my pet, I do believe you are ready. I've decided that today instead of training we are going to do something a bit different. I want to see just how sensitive your body is as we haven't played together before in a sexual way. You're a virgin aren't you?"

"You know I am. We have talked about it before." I said embarrassed. Ash was a few years older than me and had more experience dating and having sex than I did. He was 23 and I just turned 19. He just smiled and led me to his bedroom. It was larger than I had imagined. A master bedroom with a Master bath as well as a king sized bed and a large flatscreen T.v. Instead of a normal frame under his bed he had one of those things where the whole underside was a human sized cage and attached to top of his bed were little leather cuffs for tying someone eagle spread. Hanging on the wall was an assortment of paddles, whips, canes and a lot of toys I had never seen and couldn't quite identify. It was no wonder he had never let me come into his bedroom until now.

He ordered me to lay on the bed while he cuffed my hands and feet. He then produced a blind fold and tied it behind my head. I was feeling a bit nervous but my cock was throbbing with anticipation.

"So listen pet, I want to establish a safe word so that way if things are too intense for you I will stop. I want to work you up but I do not want to push you past your limit. Green means you are good, Yellow means to slow down or ease up slightly and Red mean stop. Do you understand?"

"Yes Sir." I replied.

"Good boy. I'm going to have so much fun with you. You've never been played with before so I imagine this is going to be fun for the both of us. I have a lot of exploring to do."

I felt him jam something into each of my ears... Foam ear plugs. Shit. I wasn't going to be able to see or hear... It felt like forever passed with nothing happening. I was trying to predict what he would do but after a few moments I was relaxed. That's when I felt something soft feather my balls. I couldn't help but squirm a little. I then felt my balls being lifted to the side exposing the crevice between my sack and my thigh. What i assumed to be a feather inserted itself there moving up and down maddeningly. I was now giggling and squirming trying to avoid it as much as possible but My legs were spread decently far apart so to no avail.

As abruptly as the tickling started it stopped. I took moment to catch my breath relieved but hornier than ever. Suddenly I felt something cold being dribbled on my cock. lube I think. I felt his warm hand grab me and he started slowly stroking me, spreading the lube and making my dick jump with surprise. I was now moaning and twitching in his hand. I desperately wanted to cum but he just slowly kept stoking me.

I felt his other hand trail up my body to my nipples. He circled them with one finger going back and forth getting them nice and hard. I was making more desperate noises as he started jacking me off faster and faster. I was about to shoot... Then he stopped touching me all together. Fuck! Fuck! I had been so damn close!!

"Please make me cum Sir, I need to cum!" I whined. He took my blind fold off and removed the ear plugs.

"Look pet, this isn't about making you cum. This is about seeing how far i can push your buttons before you break. You are begging now but we've only begun. I Edge most of my subs weeks or months at a time before letting them cum. I make them so horny that all they can think about is me and they would do anything to make me suck them off or fuck them silly. Have you ever heard of male chastity?"

"No Sir, what is male chastity?" I asked feeling on edge at my new predicament.

"It's where i get to lock your horny little boy cock in this cage here," He pulled out a metal device i had never seen before, "and make sure that you aren't cumming without my permission. It even has a little key with it so you don't get any ideas about trying to remove it."

My cock twitched desperately at his words and I knew this was going to be one wild and frustrating ride.