With me being a sissy prostitute for 14 years I have many. But one of the ones that sticks in my head is the 1st Time being used by the pro domme at her home, she was my best friends auntie so that added to the excitement, but the memory is having me in full sissy maids outfit with fake breasts on, heels locked on my feet the full outfit, make up, wig chastity cage which was on show from under the short maids dress and she had my hands cuffed behind my back and standing in her floor to ceiling window in her 3rd floor apartment which was directly over looking a 4 lane road with shops opposite in the early evening when it was just going dark and had a lamp shining on me so I really got attention. I had so many people looking and pointing and laughing this was 23 years ago when the world wasnt as open minded and even seeing a crossdresser was unusual, that was my 1st public exposure as a sissy and I was leaking cum from my cage. Then after 20 minutes of standing there she bend me over and put a butt plug in me infront of the window and told me to stand again looking out. She then went out and spoke to a few people who where passing and told them I was a sissy slut and asked a few men if they wanted to come and have their cocks sucked by me but the deal was it was in the window. Well this is what she told me she had done I couldn't hear her, but one man did come up and I did suck him off in the window on my knees with hands cuffed behind my back, when he came he pulled out my mouth half way through and covered my face. Then when I'd finished there was a group of men my age all shouting up and laughing and humiliating me. To this day they never knew it was me and I knew 2 of them. So ever since that when I was with them the memory always came back and sometimes it made me hard.

A second confession is when I worked in a brothel as a sissy slut one of my good friends fathers came and paid to use a sissy whore under the control of a dominatrix. I was in full sissy clothing, wig and full make up and really didn't look like myself. I knew he was married to my friends mother and He wanted a sissy bitch to suck him off and take his load in my mouth when he was tied down then to kiss him and let his own load pour into his mouth. He paid to be kept tied down after this and the sissy, me, to put my sissy clit/cock in his mouth until I came and then again to kiss and I swallow my own load, by this point he was hard again and wanted me to ride his 10 inch cock just after I'd came and for him to cum in my sissy pussy then sit on his face so he eat his own load again.
After this he wanted to be untied and then was at the dominatrix merch and she knew I knew him.
so she got him to piss in my mouth and kiss him, then she got him to tie me up bent over a sex horse and got him to put huge anal beads inside me then to leave. I still to this day don't know if he ever knew it was me and I've never spoke about it when I've seen him and I see him often. he did come back often after this and we did a lot more but that 1st time with him was so erotic and exciting but humiliating at the same time. But truly amazing for sissy whore.