Sissy tasks: The car ride!

This one is very simple but also a lot of fun!

Dress your sissy up and go all out (miniskirt/dress, makeup, fake nails, fake eyelashes, high heels; make him a little slut!). Wait until its dark outside and take him out for a car ride. Drive to an industrious zone or a highway parking lot or a nearby park/forest (a place very few people would visit at that hour). Stop and tell him to get out. He'll be shocked but explain to him you will pick him up
shortly after to soothe his feelings.

Drive around the block once and pick him back up. For fun you could pass by once and honk!
You can make this as daring as you want, for example tell him to stand under a street light or tell him if he moves away from his spot you will drive off and he needs to walk home.