do you want to help me think of a specific dare to give him in the next few minutes?

One that involves anal and cum-eating. I was thinking of having him jerk off onto his face with his mouth wide open. But, what could we add on to that?

You can work a dildo in and out of him. Plus, you can have him pretend the cock isn't his, and beg for it , saying things like "please sir, cum all over my face, I'm A naughty slut.

Dressing him up like a slut should be obvious too.

Also if he misses at all, you can take a dildo, smear it in the cum, and shove it in his throat. Have fun! ;)

I need to start having my boyfriend work on his anal!

Can someone please help me?

for anal, a strap-on is a must for you; for maximum humiliation it should be larger than his dick, perhaps much larger. Then you have something to work towards. But start small, ice cubes, a few pencils, or a small plug are good starter options.

hmmmm, what should i make my boyfriend do tonight?

give him fake boobs, and make him hump something with them.

What should i use as fake boobs?

Hmmmm.... I can't think of anything -___-

Socks, balloons, oranges, ect.

I'm looking to get sissified

How is your sissy's progress so far

he has done a lot for me so far.

i do not think he is enjoying it however.

I am trying to figure out how i can make a household buttplug that is pretty big, but I can't figure anything out?

Would you like to help me?

I've always thought that submissive males were pretty much worthless. You should turn him into a cuckold.

Has he told you he doesnt like it? Maybe you should ask him whats wrong. You could be doing to much to little. write your name on him to remember who owns him and why he's doing it. And tuck his penis behind him so he feels like he doesn't have one.

hi, i'm not a big fan of sissyfication but i know a few things about domination, this is all about after all... first, anything you do to him it must take place gradually, he will not be able to accept at once everything you have in ur mind, but, if you make each task more diffcult than last one, he will do almost anything in the end.. second, you must play the game of punish and reward, for example if he did the last task really good and he prove devotion you might let him fuck you, if he did it good but not perfect, you ask him to get on his knees and masturbate on you (while you laugh of his effort of course), if he did i wrong, no cum of any type for him for a while or ass fuck for 5 minutes, or..... well, the possibilities are infinte, use ur imagination for punish and reward (reward should always involve him to cum one way or another tho)...btw, would be nice if you can make him wear all the time a handmaiden dress... but anything you choose to do just remember he's still a guy and he need to cum but he's also submissve so he need to be punished as well, if you take this step by step, each time go a bit further he will love to be your bitch in the end