Sissy masturbation means sissy eats her own cum.
This is basic sissy masturbation assignment, omitted if Mistress is feeling merciful.
However, since this is also sissy masturbation punishment, it isn't likely that this Mistress will ever show leniency to an errant sissy. Humiliation, especially after coming, when desire and submissiveness is at its lowest level,
is difficult for many, but you will learn.
No begging, ever!
When the sissy has not cum for a length of time, Mistress demands that he squirt his cum all over his meal before eating it. Sissy might have to be very creative if he is having his meal in the presence of others who are unaware of what's going on. Mistress's demands must be met so begging will be met with scorn. Your masturbation punishment will be increased.
Failure is a NO NO!
Mistress becomes angry when a sissy fails, she could dress him up and put on a show for her friends. Sissy might be ordered to dance to music in a provocative way while playing with himself and dancing around the room.
the humiliating punishment would be even worse if Mistress's friends were not in the scene and had no idea that men would do such things.
You will enjoy some strange things!
Sissy is ordered to save his cum in a small container such as a 35mm film canister (wash throughly before using) and then freeze after each deposit. For a full-sized cube, several orgasms would be needed. Mistress has him suck on the cum cube while he masturbates and if the cum cube melts before he is allowed release, he must hold the goo in his mouth until given permission to cum. Only then is he allowed to swallow the cum in his mouth.
How many different positions can I put you in?
The sissy must masturbate lying on his back, with his legs raised and down over his head so the tip of his cock is as close to his face as possible. It is Mistress's choice whether she has her sissy shoot all over his face or into his open mouth. Of course this is a ridiculous position for sissy and Mistress is sure to laugh and make fun of him.
Does your chewing gum lose its flavor overnight?
Sissy is ordered to masturbate while wearing an nonlubricated condom. When he's cum, he must remove it being careful to not spill any. Sissy is then ordered to put it in his mouth and chew it like a piece of bubble gum until he has sucked all of the flavor out of it.
I might heat things up a bit!
If sissy has been particularly bad, Mistress might command him to coat his cock and balls with Capsaicin, an arthritis cream that contains the derivative of cayenne pepper. It has very long lasting effects and does not wash off. He will feel like his cock and balls have been placed in a bed of red hot coals!
Mistress listens well and can be very directive!
One very humiliating masturbation punishment for a disobedient sissy is for Mistress to have a man call him on the phone so that sissy has to have phone sex with him. Mistress might choose to listen in and give instructions to her sissy so that he doesn't disgrace her by an inadequate performance. Of course, when sissy cums, he must moan and groan loudly which humiliates him even more, knowing that he has been turned on by having phone sex with a man.