I have been dressing in secret on and off since I was thirteen. My sissy self is a virgin apart from having worn a butt plug and pushed a few objects up there.
I have a bit of an addiction to the fantasy of entering into a blackmail agreement with a few limits included. I and possibly others would be being blackmailed remotely to create videos performing more and more humiliating tasks in each on with the consequence for not completing the task being that all of the clips are uploaded. I don’t find financial blackmail to be a turn on at all so would not be willing to enter into this. There would be an exit path for this which would be to perform a rather painful and very humiliating task which would be published.
I also like the idea of having a master or daddy which I would share with another sissy slave. This would mean that we could do things together and play with each other for his amusement. And then we could each pleasure him, either individually or together. If doing this I would really like the other sissy to be an experienced one who could take on a teaching role. I also think that it would be the ultimate turn on and humiliation for the master or daddy to then when he was done with me give me away to someone else.