I have!
It was the very first sissy task I had ever been given. I actually didn't even know that's what it was called at the time. I told a girl I met on a local chatting app and liked, and had a sort of "flirtationship" with in college, I fantasized about being in the middle of a mmf. Our conversation led from one thing to another and she convinced me to let her paint my toes and wear pantyhose the next day to work (call center). I did it, and throughout the day she texted, asking me asking for me to go to the restroom and send her pictures. In the end, I never did get into a real relationship with her. She convinced me to download Grindr, it's because of her I ended up sucking cock for the first time. She had told me to set something up and send her a picture of my mouth full of cum, which I did. And then i swallowed it (it didn't cross my mind that spitting was an option), when I told her that later she laughed, like, a lot. She ghosted me shortly after. The last task she ever gave me was to pick up a banana from the store and put it into my ass and send a picture. That was the last picture I ever got to send her. I kind of wish I could find a way to contact her again and thank her, I never would have started my journey without someone like her giving me tasks to get me started. I didn't even realize what was happening at the time, "sissy" wasn't a word that meant anything to me back then. Thank you 'BYUIBOOB', for helping me discover so much about myself
