Time for a flashback that I’m sure many readers will love.

Since the last 24 hours have been a “slow day” here, it’s time to tackle one of the items from my “Future Topics” page.  Today’s item: “How she had me humiliate myself to others one day to get out of chastity”. This is a true story.

Last month we traveled out of town to attend a kinky weekend event. There were workshops during the day about all sorts of things like bondage, CBT, medical play, role-play, kinky toys, etc. There were vendors with all sorts of fun sex and BDSM related wares and clothing. And after dinner the dungeons were open for play. People were dressed in all manners of fetishwear. It was a really fun weekend.

When we arrived I had been locked in the CB-3000 for several days. This was pretty early on in the “chastity era” of our relationship — just a few weeks before I started this blog. My wife/mistress/keyholder had an evil, wonderful, nasty plan for me for the first evening.

She said I could get unlocked and have an orgasm if I could find someone to unlock me. But there were a few further requirements.

First she helped me get crossdressed. I had a plaid dress with a big pink belt/bow, white hose, and shiny Mary Jane shoes. She fixed my hair and makeup. I really did look quite good. Slutty, but fun.

Then she had me write a note that said: “My Mistress will allow me an orgasm if you will unlock me. I can give you a BJ. Will you please help?” She pinned this to my dress along with the key to my chastity lock. She was clear that I was not to touch the key for any reason.

Then she got ready. Soon she walked me from our hotel room, through the public hallways, to the private party area. There she allowed me to interact with people and to plead my case. At first I was really embarrassed and hesitant to approach anyone. The first few men read my note and actually laughed about it. They all declined.

We moved to another area, and I got a little more comfortable talking to people. However, man after man still turned me down, most of them laughing at my predicament. Some lifted the front of my dress to see my chastity device and lock for themselves. The evening went on and it seemed that I was not going to get unlocked. My wife was clear that she was ok with that outcome.

In the quiet dungeon we met a friend from our town who was also attending. She introduced us to her fiance, who was also dressed up pretty. Although we had not met before, it was clear that he was her submissive, so I asked her permission to offer my note to him. She agreed, he read it, and I gave them some time to discuss it. I sat next to my wife to wait for their decision. Soon our friend motioned me over and told me they would be glad to help.

For some reason this wasn’t quite the joyous moment I expected. I had been so focused on finding someone to unlock me that I had forgotten my part of the bargain. Now I had to suck this man’s cock! And not just that, but in front of my wife, in front of his Mistress, and in front of the other people in the dungeon.

Keeping the end of my penile captivity and my pending orgasm in mind, I knelt in front of this man I had just met. He lifted his skirt and revealed his cock to me. His Mistress handed me (!) a condom, which I carefully applied to his erection. I looked back at my wife, and she gave me a look that said “Well, what are you waiting for?”

I leaned forward and took his cock in my mouth. Although it wasn’t the first time my wife had put me in a position to suck a man’s cock, it had been years and it felt all new again. I worked him with my lips and mouth and tongue, and listened to his responses to help me gauge what he liked. Soon I became aware of his Mistress complementing my wife about what a good cocksucker I was, and how they both really seem to be enjoying it. But mostly I wasn’t aware of anyone or anything around me, as I was focused on pleasing his penis until it came so that I would get to cum.

Fortunately he didn’t last long, and his orgasm was clear to everyone. Once he finished I laid my head on his thigh, looked at his cum in the end of the condom, and thought happily to myself “I did it!” Both women commented that I seemed to be quite a slut, and that it looked like I really enjoyed sucking cock. This made me blush and, still on my knees, I acknowledged them both with a “Yes, Ma’am”.

I finally looked around, and it seemed to me that there were a few more people than before in the dungeon. My wife picked up on this and told me that “everyone” was watching me be a little cock whore. I didn’t care, it didn’t feel wrong to me, although I still felt somewhat embarrassed. I also felt somewhat fulfilled — that I had accomplished something and that I had pleased my wife. In hindsight I realize that she must have really enjoyed the entire evening of humiliation that she set up for me and made me endure.

And yes, an hour or so later back in our hotel room, she gave me a most wonderful orgasm.