New Year Chastity Day 1

With the coming of a new year, I planned on starting a new chastity cycle. For a few weeks in late-November/early-December I had a dom who told me I need to ask permission before jerking off. I was allowed to cum if I played with other guys, I just couldn't get myself off. This was fine and a great way to start things off, but I did this with the expectation that he and I would be meeting soon. Distance and schedules have caused us to still not meet. Knowing that I would be going out of town for the holidays and he wouldn't be available to meet any of the couple weeks before Christmas and the New Year, I took control of my body again.

Updates and Dilemmas

I've been a bad little sub boy lately. Actually, I haven't been much of a sub boy at all. I've been busy working mostly and having a non-sexual life hanging out with friends, meeting new guys, and just going on dates. I've talked to a few kinky guys here and there, but have yet to go anywhere. Guys on Recon are lame and flakey for the most part; and another guy I accidentally ran into from Scruff, after talking on and off forever, wasn't sexually interested. Why not? I'm hot shit!

Working in Chastity

Going to work during the 30 days of chastity was quite interesting. I work part time in mostly office environments. I'm sort of a freelance or temp employee, and don't work everyday. During this time I was in a work setting where the other temps and I had developed a really strong and close-knit group. Some are my best friends. One is the same girl who had the pool party I attended my first day in chastity. You might recall that I was worried about her possibly sitting on my lap. She is a flirty red-head in an open relationship with her dom boyfriend. Sitting on a gay man's lap was nothing. She'd also sometimes "boop" you from behind with her pretend penis.

30 Days and Done

It was fun and definitely an achievement, but after 30 days in and out of chastity not cumming, it was time for this all to end. With two Sirs in different locations, all of us in different time zones, and different schedules it was hard to keep up. I was pretty busy with work and couldn't keep up with the readings either. Sir Rich and Sir Rob were proud of my accomplishment. Who goes that long their first time in chastity?

Crime & Punishment

I was a bad boy. I didn't do what I was supposed to do, and now I must face the punishment. This is the course of life for a sub boy - Sirs order you to do things, and you either follow them or you don't. Follow them and successfully accomplish the task, then be reward. Don't or fail, then risk punishment. Sometimes it can't be helped.

The Pool Party

My second day of chastity and I had a pool party I was supposed to go to. This is the day I was talking to Sir Rob, before he officially came on. I hadn't heard from Sir Rich yet that day and asked them both whether I should wear the device to the party. They, of course, both ended up telling me a resounding "yes!" What's a boy to do? He has to do as he's told, right? 

Sir Rob Joins The Fun

I first met Sir Rob years back in my hometown of Chicago and he lived near my work. He and I had a couple sessions, and they were always fun. He's in his mid-40s and very sexy. I met him on recon and we met out for a drink first. He had a natural dominance about him that immediately turned me on and made me want to submit. I didn't care that he wasn't into leather, which I really love. There may  have been one time that we played where he was in leather, but it was so long ago I can't really remember.

Sirs' First Assignments

Sir Rich was happy to take control of my adventure in chastity. First job was to trim my pubes down when I arrived home from work and to let him know when my CB-6000 arrived. I knew it would be either that evening or the following day. To my delight, it was waiting for me when I got home. I immediately trimmed my pubes and locked it on. I sent Sir Rich the photos and let him know his boy was locked up.

Locked Away in Chastity

It had been weeks since I came. My body reminded me of this late last Wednesday during a dream that ended with me filling my pajama pants with a hot load that ran down my leg. I had thought about jerking off a million times before then, but I'd always get distracted or busy with work and too exhausted. Or maybe I just know that my cock is such a worthless little fag dick that I don't have any business using it. I know it doesn't really belong to me. There's someone out there who really owns it. Maybe everyone else owns it but me. I'm a submissive, and I need to be controlled. I didn't need nor deserve to cum, and that leads you to being a horny, more obedient sub willing to do anything and please a Master in anyway. I knew I shouldn't cum by my own hand and had to make sure I wouldn't.