I was shopping at the mall run into a guy I recognize from class. Technically I saw him first standing outside a dressing room looking at a mirror and holding a pair of panties to his crotch. He thought he was alone but I just came up at the right time. My giggling gave me away, and he looked so embarrassed. I told him not to because truthfully he had a lot of great feminine features. So I encouraged him to come into the dressing room with me as I was going to try on some clothes.
I pulled him back with me and the first thing I did was rip the tag off the panties and told him to put them on. Once on I adjusted his oversized clitty to help the panties feel more comfortable. He told me he never had a girl help him with panties before, or anything sissy related. So I asked if he had ever had a sissygasm before. Wasn’t surprised to find out the answer was no, but I was prepared. I reached in my purse and pulled out the little pocket rocket that I keep on me on certain occasions. Then I encouraged him to bend over for me.
I set the vibe on low and teased it up and down his little taint area from under his balls to his sissy faggot pussy. Giggling as he trembled. Then slowly turned it up to a medium vibe and pushed it inside him. Angling it up to press his little sissy g-stop, he moaned loudly rubbing his clitty. Gently I began pulling it in and out faster and faster until I made him cum like a good sissy slut who lets strangers take advantage of them.