It Makes Me Smile to Know This

Here are several more paragraphs from the Lucky Boy about his experiences in chastity, getting a reward, disappointing me and my response to the disappointment. Enjoy!

Miss Ruby took me to her space, tied me and blindfolded me. Now, I had been told not to wear my chastity cage that night so, there I was blindfolded, pants around my legs and my cock hard, dripping and aching for Miss Ruby. I had no idea what would come next and her mastery at being in charge only fueled my sexual desires even more. Miss Ruby invaded my ass, stroked my cock, clamped my nipples and took complete control over my willing body. I wasn’t allowed to cum and she brought me closer and closer to the edge and then back again. I had such a desire to cum but my desire to be good overcame it. Then she gave me permission to and I couldn’t. I wanted to so bad, I was right there on the edge and I tried and tried and Miss Ruby was being so good to me and giving me everything and more than I should have needed to cum but I just wouldn’t. It was like this frustrating combination of all my insecurities and having not cum in almost three weeks and I never came. After we were done and I was left frustrated, feeling like I had been a disappointment, Miss Ruby informed me that I was not allowed to cum and she also gave me some new chastity rules.

Whether or not I had truly been a disappointment that night, only Miss Ruby knows. However, what undeniably was a disappointment was me, the following morning. Not only did I break the chastity rule while shortcutting but, while doing so I also broke the rule of not being allowed to cum. I was so frustrated with having not cum and still so heated with my desires for Miss Ruby that I took from her what was hers, what I had voluntarily given up control of. It was one of the worst orgasms I’ve ever had. It was painful and I felt like such a disappointment during and after. I felt pathetic. I chastised myself and argued with myself all morning between telling Miss Ruby and not telling her. I knew that I had to be honest so I sent her a text telling her what had happened. I waited and waited and since having met her I had the worst day at work. I was close to tears throughout that day. I mean, she had taken such good care of me the night before and I ruined it all with one little selfish action. I just knew that she would be angry and feared she wouldn’t even want to have anything to do with this pathetic submissive who was untrustworthy. She did forgive me but, she was worried and rightfully so. I was relieved that she forgave me and I got to go and see her again that evening.

We spent that evening visiting and discussing what I had done. I couldn’t even look at her unashamedly for the longest time and she could definitely tell. Miss Ruby seems to be able to peer into my soul and see exactly what I need, deserve, what I desire and if not, she certainly knows how to get it out of me. That evening I had the sincere pleasure of staying the night. It felt absolutely amazing sleeping next to her. Miss Ruby’s body not only looks perfect but it also feels perfect. Her soft skin, soothing voice and her touch, oh that touch, are all so amazingly delightful to be curled up next to. I got to lay there with my head on her chest for quite some time, listening to her heartbeat as it lulled me off to sleep. It was the best night’s sleep I’d had in quite some time and even though I only got a few hours I felt rejuvenated. I was the happiest boy at work the following day and people couldn’t figure out what was going on with me. I was goofy and playful and probably the most positive that I’d been in quite some time. Miss Ruby had forgiven me, I did have a punishment coming, but her forgiveness and her desire to still want to see me and not give up on me meant so much to me. I have this fear in relationships that I’m going to be tossed to the side, be given up on, or just suddenly and without warning cut off. It’s happened to me in the past and it frightens me to the point to where I pretty much just expect it. I’ve avoided some potentially meaningful relationships in the past or ended some because of this fear. I hate having that fear but, I have this trust, feeling or, whatever you want to call it that Miss Ruby’s not going to give up. She seems to want me to serve her, to be a good boy for her and I have every intention to do my best for her. 

I got to stay with her the following night as well and spent most of the next day by her side too. We slept in together, she held me, she teased me and, she made me feel safe. I enjoyed every moment with Miss Ruby. We worked on a project together and I got to see a really fun and funny side to her. There was barely a moment where we weren’t either laughing, touching or just simply enjoying each other’s company. All of the kink aside, it’s a real treat to be around someone you can have that kind of a connection with. She makes me feel not only like a good submissive but also like a special person who’s worth her time to be around and who is adding something to her life. I don’t ever want to take away from Miss Ruby. I hope that I can be just as good to her as she’s been to me. 

As for everything else, I’ve offered to take pain for Miss Ruby. I’ve always felt that BDSM was a two way street. There is a reason why Dom’s are Dom’s and sub’s are sub’s. I want to take her pain, I want to be her good boy, her whore, trustworthy boy, friend, submissive – whatever she needs. What I don’t ever want to be and what I will put every effort into; is to never be a disappointment again.