Story: Skin part 5

(continued from part 4)

In my last update, I said it would only be a matter of time before I got in some sort of trouble that would get me a hard punishment, and that's what happened. About three weeks in my new chastity period, I was getting seriously bored and annoyed at my cock being locked up. So I straight up asked Master Thomas if I had to be in chastity any longer. I knew it would very likely get me into trouble, but I was so annoyed and I guess angry as well. "Boy, you're getting punished for that, I told you not to complain about anything chastity related unless you're having a medical problem with it". Before I knew it, I blurted out "But I didn't complain, I just ASKED."



I knew I made another big mistake by saying that, as one of the rules of being his boy was that I wasn't allowed to talk back to him, unless it was done in a very respectable way, and I wasn't allowed to start a sentence with "But" if it involved a decision he made.
The thing that hurt me the most was that after I apologised, he said nothing and just sighed. I knew I had disappointed him, and I really did feel bad about myself.

Later that day, he called me with him while he was sitting in the sofa. I was ordered to lie down on the sofa, with my head in his lap, while he asked how I felt about what happened. I told him I felt terrible for letting him down. He sympathised and said I needed a hard punishment, if only to get rid of these negative feelings, and to "come clean" about the whole thing. He also said that maybe we were moving a bit too fast, and that I had to re-learn the basics and know my place.

A moment later I was on my knees in front of him. He pulled me closer by my collar and said "What does this collar mean, boy? Tell me."
"It means I'm your boy, it means I have to obey you and that I'm loved and protected by you."
"Good." He started fondling my nipples, and quickly started playing with them more roughly. I softly moaned and closed my eyes. "No boy, look at me, and tell me, who do these belong to?"
"They're yours Sir..."
"That's right boy, and will use them as I see fit. I like torturing them, and that is something you'll have to accept when you wear my collar".

While still working on my nipples with one hand, he moved his other hand down to my (still locked) cock and balls. He squeezed my balls, first softly, then more firmly. This is a pain I very much dislike, of course he was aware of this.
"Tell me, this cock, these balls, who do they belong to, and why is your cock locked up?"
It was starting to get hard to answer him, the pain and discomfort was numbing my ability to think normally, but I was still able to say, albeit in bits and pieces, "They're yours Sir...I'm locked up because, being a boy, I would otherwise masturbate all the time...it makes me focus on your sexual pleasure rather than mine, Sir."
"That's right boy. You must always keep in mind that this is for your own good, because it helps you to be a better boy." He stopped his assault and allowed me to catch my breath.

My next order was to turn around, and stay on my knees and elbows, so that my ass was facing him. He started spanking me, not hard but holding a steady rhythm, while he asked me who these ass cheeks belong to. "They're yours Sir."
"That's right boy, and I love to see them when they have a nice red and pink glow to them...so I will spank, paddle, cane and whip you when I want, because it will please me. Remember that boy".

Then he got up; a moment later I could hear him fetch some items in the bedroom. From the familiar sounds I could tell that he put on some latex gloves, which in all likelihood meant that he would be fingering my hole shortly. He did, gently at first, but rather roughly after a few minutes. "Who does this boy-hole belong to, boy?"
"It's yours Sir."
"That's right, and I love fingering you like this, because I know it makes you uncomfortable both physically and mentally... and you know, one day, I will fuck you. You need to make your peace with that. It will happen. I want you to give up your resistance, and let go. Not easy I know, but it will help you, trust me."

After that he allowed me to rest, and brought me something to drink, while he warned me that my punishment hasn't even started yet. For just one nanosecond I thought about running away, or telling him that I can't take any more of this, but my submissiveness and loyalty to him took over. He sensed that I was anxious, so he pulled me close and hugged and kissed me. "Scared, boy? You might need that adrenaline later on. But you will feel better after the punishment, trust me."



I had to get back in my earlier position - on my knees and elbows - while he started whipping my ass. He used all sorts of instruments of pain on my ass; whips, paddles, the cane, and possibly even more. His rhythmic hitting, together with him encouraging me to "let go" and "give up", sent me in a strange headspace. Much deeper and darker than I experienced before, even if it wasn't completely unpleasant. It sound weird but at some point I had a vision of a crystal vase or something, and with every hit, there appeared a new crack in the vase. I was so fascinated with the vase and how it changed that I hardly felt any pain anymore. I guess it was some sort of self-defence system against pain that my brain came up with. I was still conscious through all this, it was just a very strong visual imprint.

It actually took me some time to notice Master had stopped hitting me."Where have you been, space boy?" He took off my blindfold, and helped me to the sofa. The ball weight and nipple clamps were taken away, and he hugged and kissed me and said he was proud I took the punishment so well. "Well, the first part, we're not done yet." I was too tired to make a remark about that. He held me in his arms for a while longer, and after asking if I was okay and if I wanted to go on, he told me to stand up straight again.

This time, I had another ballweight attached to me, but a heavier one than before. And the new nipple clamps had extra weights on them as well. I wasn't sure how long I would be able to take this... Master first ordered me to walk around with my new "decorations", and when I was almost outside the room I had to crawl back to him. This was even worse - gravity is a real bitch you know! The weights on the nipple clamps moved around with every motion I made. I tried to move very slowly towards the sofa, but Master noticed this and said I now had two seconds to get to him, otherwise I had to crawl back from where I started and do the entire distance again.

When I was with him, he told me to stay like that, while he put his laptop in front of me. He put on the video that was taken the last time he locked the chastity device on me - the one where he made me beg to be locked up and that I wouldn't complain about being in chastity. It was embarrassing to see myself like that - not just the begging, but the video also had footage of me cumming, and Master feeding me my own cum. He kept the video on loop, while physically and verbally humiliating me as well. He used the cane to move the weights on the nipple clamps around a bit, and lightly spanked my balls, and all sorts of stuff to make me physically uncomfortable. He kept making comments and asking questions, just to further humiliate me. Like asking me if I regret asking him to lock me up ("no"), and then saying "well maybe you'll regret it if I deny you orgasm for a year or so. Then if you feel sad about getting no orgasm, you can watch this video again to see that it was you who asked to be locked up". Not just that, but he also made comments about my balls, how they are "so small, they're really boy-balls aren't they?" and that my cock is so small, it should be in a much smaller chastity device.
 Knowing him, he would make sure that some of the things he said would get a follow up - he already casually mentioned that Dan was wearing a custom-made device, and that I would need one as well since "your little cock has too much space in that cb2000".

After finally deciding that I had enough, he removed my "decorations" and put my chastity device back on. We had a light meal and went to bed, as we were rather tired. Hmm, I wonder why. I fell asleep almost instantly, but not before hearing Master say "Hey you know what, since you've been naughty, maybe I should start treating you like a little boy, like I sometimes do with James. Ha ha, it's always funny to see that look on his face when I tell him he's going to be in diapers all weekend. And it's even more fun to put him in front of a mirror to confront him with his little boy status. Yeah I think that would be good for you as well.  Anyway...goodnight boy!"

Wait, what?

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Hope you enjoyed it, as this was the last story for a while (and possibly the last ever in this series).