Take a pillow, go to a wall of your choice, put the pillow between your crotch and the wall and hold it there by pressing it against the wall. Now put both hands against the wall as well, and cum just by humping the pillow

Let’s go with a sissy classic. Legs over head and aim for your mouth. Every minute it took you to cum is a minute you must hold it. You may spit after, but a true sissy would swallow

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On your knees, lean back such that you need to have a hand behind you to support you and try to cum all over your chest

You may only touch yourself while in doggy position

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You must orgasm in front of a mirror with the largest dildo you have in your mouth

Looking in the mirror fully crossdressed in a pink skirt and crop top with thigh highs or maid dress. Cum into your hand and lick it up if you’re daring

Strip naked lay on your back legs open wide and up in the air, put two Very messy substances in plastic bowls one on each foot cum like that hope you don't spill the mess on your face.

Hog tie yourself and cum while humping the bed

You must start with plugging your ass with a small plug once done you have to either piss into your mouth or into a cup then drink it but hold your piss in your mouth don't swallow it! Now remove the small plug and put a medium sized one in aswell as attempting to put your ball gag on without spilling any piss! If you spill any of your piss you must use it as lube for your next plug the biggest one you can take. So now you should have the biggest butt plug in your ass, piss in your mouth with your ball gag on.

Now you can cum but with your legs over your head/shoulders so you give yourself a self facial. If that's a limit you may cum normally but swallow your piss at the same time.