Sissy Simone

My real name is Simon. My other name I go by is ‘Sissy’… by name and by nature.

My first experience of dressing was going through my sisters wardrobe and pulling out her short, red stretchy mini skirt. Also her black high heel knee high boots. I was so excited to try them on and just wanted to see what they looked like. I can’t remember what the impulse was to put them on, l just seemed to do it naturally. Looking at myself in the mirror instantly got my heart racing and became very excited by the experience.

I was in my late teens, possibly 19. I’m now 35 and have been dressing in various sexy femme items off and on ever since.

I started setting up a self timer on my camera, and taking photos. that then quickly led to posting photos online to see what others might think. I quickly realised that men particularly enjoyed looking at my photos, and knowing how much they enjoyed them, just spurred me on to dress more, chat to men and even the odd camming. I loved the idea that “real” men loved to see and enjoy my private pictures.

My favourite outfit to wear became a white lace stretchy chemise with matching holdups. The perfect combination of innocent sissy virgin, and sexy slut! 😉

I learned from chatting online that my slim smooth body was built more for men to enjoy than for women, and the sub role became a natural fit for me. This led me down the sissy maid exploration and a discrete purchase of my first satin  maid outfit; Black with pink ribbon trim, black choker with pink trim, matched with pink and black satin suspender belt and stockings with pink bows.
I’ve never felt more of a sissy wearing it!

After chatting to many men online over the years, camming became dull and frustrating, and eventually was inevitable that a physical meet was going to happen. I’m very selective on who I chat to at length, and even more so when it comes to meeting in real life.

Perhaps my first experience of meeting is for another time….


Sissy x