Top 10 Sissy Humiliation Tasks

Today you will be going out for a jog. Put on your cutest pink athletic wear and load your phone up with your favorite girl bands. You’ll be jogging, walking, or running through your neighborhood while listening to your music. Make sure to sing along to any of the words out loud as you do so.

Task Requirements: 20 second video of you jogging in your sissy outfit and singing to your favorite girly band.

You will be giving yourself a sperm face mask today. When you go to edge yourself, you must masturbate to shemale/sissy pictures, videos, or porn. When you feel you are almost ready to cum, take a cup, stick your sissy clit into it and fill it up with your hot cum. After you fill it up with every drop, you need to scoop out your cum from the cup and rub it all over your face. You are to let it slowly dry before you go to wash it off.

Task Requirements: 2 Photos. 1 Photo of your cum covered face (wet), and 1 photo of your dried cum covered face.

You will ruin an orgasm into a shot glass, then pull up your panties and get dressed to head to the store. Dump your cum in your mouth, then go shopping. Do not swallow the cum until you are back in your car.

Task Requirements: Photo of the cum in your mouth before shopping, a photo of it still in your mouth while shopping, and a photo back in your car, holding the receipt, with your mouth open showing the cum.

This next sissy training task, you will be required to go out and purchase a prepaid cell phone. Every time you go into a new bathroom at a restaurant, mall, or public place, write your number in a stall along with an offer to give out free blowjobs. You’ll need to carry your prepaid phone with you at all times in case you receive any calls or texts wanting your service. Depending on how brave you are, you can reply accordingly.

Task Requirements: Photo of your new phone and the number given to it, as well as 3 photos showing your message written at three different locations.

Go to a gay bar and enjoy a couple drinks to loosen yourself up. If you do not drink, you may skip that part. Head to the bathroom and check everywhere for a glory hole. When you find one, knock a couple times to let anyone on the other side know that you are there and willing to perform. Give them a blowjob or hand job and let them cum all over your face or in your mouth. Make sure to get a video or a couple photos of you doing this.
If there is no glory hole, or if no one puts their cock through for you to play with, ask a couple people at the bar if they know a place with an active glory hole you can go to.

Task Requirements: 30 Second video showing you pleasuring the random cock, and getting a face full of cum.