I agree that trying to put a chastity device on is an awkward experience, especially if it's eating into session time. I wanted to experience a night sleeping with a cock cage on. I scheduled an early evening two hour session with Ava St. Marks and at the end of the session she was able to easily slip the cock cage on with no problems. Ava took the key, sealed in an envelope, wrote her name over the sealed section and gave the envelope to me with instructions to return in the late morning with the envelope still sealed for another two hour session. I had the key so if for some reason I HAD to take it off I could, but I enjoyed having it on so I didn't use the key.

Since the device was already on, we were able to immediately start the session. Eventually she said it was "in the way" when she wanted to move on to the CBT chair for some exquisite CBT. By splitting the session into 2 separate 2 hour experiences, and placing the device on at the end of the first session, I was able to experience a night in a chastity device without the awkwardness of trying to put the thing on with a raging hard on. While Ava has sine retired, I am very grateful to her for the experience and both sessions are lifetime memories for me