My first official male chastity photo shoot was with a massuesse who modeled part time.

I was both nervous and excited by the prospect of working with her. Even though we had discussed it, allowing her to see me in my chastity cage made me apprehensive.

Before the shoot, I browsed over all my favorite chastity pictures on Tumblr, trying to get a feel for the type of images I might shoot.

Not a photographer by any means, I was looking for interesting angles and ways to frame my shots.

Thinking back on this, I should have created a list, because once I arrived all my thoughts flew out the window.

The shoot was to be no physical contact in any sexual way. She agreed to massage near my cage, still we wouldn’t be doing anything illegal.

Consensual things happened, but they were not agreed to in advance.

The bonus here was that she didn’t mind having her face in the shots. That really excited me because some of my favorite images included the keyholder gazing up into the eyes of her chastity slave.

We met at a little motel in an out of town place for the shoot. She put me at ease as I set up my video cameras and we decided we would start with me on the bed and her teasing my groin area.

One shot was to be POV. Another camera caught a different angle and a third was trained on my chastity.

Weeks of planning the shoot and years of fantasizing about having these types of things happen to me collided.

She barely touched me on the leg and I suddenly had an orgasm in my cage. This premature orgasm was hot when I watched it back on video.

After cleaning up, the rest of the shoot went extremely well. She turned out to be a very kinky lady with some hot ideas of her own.

I ended up releasing the premature clip on my PornHub account. (I wasn’t Tiny Chaste yet.) The clip got over 100,000 views while it was online.

I ended up taking it down when I discovered someone had downloaded it and put it up on their own account. Later I closed that account and opened my current Pornhub profile to show previews of my clips.

You may remember the image if you watched videos back then. I also got some great stills that started being shared on Tumblr.

People began to ask me if I would be sharing more. But that is a story for the next post.

By the way – be sure to check out our new Male Chastity Photos Gallery