Oct 25th, 2009
I travel to Mexico once again with my chastity device locked into place. Going through security this time didn't seem to be as big a deal. I figured if they scan me and notice something underneath my clothes and ask I'll simply tell them and I guess the worse case is they have a story to tell. For that matter I suppose I would have a story to tell myself. My flights I'm happy to say where all in all uneventful.
When I arrived to my place of work I went to sleep almost right away seeing I had just took a redeye to get there and I had to work that night. Sometimes I wake up with a hard-on (many times) and when this happens it tends to burn on the back of my balls from the cock ring pulling on them. If I can relax fast enough this isn't a big deal. But I notice I was having trouble staying asleep so I took it off early then I was suppose to. I'm suppose to wait one hour before I go to work to take it off. When I get home I will tell my DD as I will not try and get away with anything. I'm enjoying her guidance in all this.
After work I showered and put back on my chastity as agreed. That night I slept and kept waking up again and again with the rubbing and the burning and finally said screw it and released myself once again from the chastity. And went back to sleep. I slept so much better. In the morning I wasn't sure weather or not to put it back on. I decided that I will leave it off and let my testicles heel a bit more. I made a deal with myself that as long as I was out and about of my cabin that I could leave it off. I was out of my cabin all day and night, lol. I simply knew that I wasn't going to have an orgasm when I was out of my cabin is why I made this deal with myself. The temptation would only come when I was sitting alone in my room. I am now back in my chastity once again and so far everything feels great and I was able to do all this without orgasm. To my surprise I really didn't give a whole lot of though to masturbating.
Last night for the first time I tried milking myself via prostate massage. I was successful a little bit. I can see where this would work well under the right conditions as well as being very arousing. Doing it myself though I found it to be very hard. I will try and get toys specially made for this and see if that helps and give any readers I have here an update when I do.
Sorry for a boring read. I'm just keeping this as real as possible.
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