Tag Archives: Sissy Penny

Exposed: Sissy Penny

I am a 35 years old closet sissy with an athletic body trying always to look as sexy as possible.

My goal is to look feminine and not just a man in lingerie.

I adore women and the main reason I crossdress is trying to look like the girlfriend i would love to have. I love skin tight clothes and i adore high heels.

I want to find a girlfriend that will love me the way i am.

I always fantasized about being in chastity by my girlfriend and where that could lead me. I do not like men and do not wish to serve one also.

I consider my self a man with fetishes one of which is crossdressing. It is not a mandatory fetish but one that can spice things up a bit. I don’t know why I made this submission, I guess I needed to confess my feelings.

One of my fantasies is to be dressed as a maid in ballet boots, on a locking corset and in an arm binder with a locking gag as well locked in chastity and forced to serve my girlfriend and her friends in a kinky party.

The need to be trained in becoming a better serving sissy is something that exists in my mind for quite some time now and hopefully in the near future this will be a reality.

I hope you all loved this diary submission and hopefully this will persuade many more to do the same.

With Love Sissy Penny. <3


Thank you for sharing! It’s important for everyone to understand that not all sissies/crossdressers/panty lovers/ etc are made alike. There is no such thing as a one size fits all box.

Many of us fetish lovers and seekers just do it because we like it, we want it and we are going to engage and enjoy.

I hope you make that connection you seek that goes above and beyond. Best of luck, Doll!