He might not be into it but it can't hurt to try. And don't be surprised if there are things written that you weren't expecting.

Well written journals should be praised and encouraged. He may understand his submissive journey and desires a lot more by engaging his brain to evaluate them. He might text to tell you but by writing a reflective journal entry after the event, it can be tantilising for the both of you. Whilst he is at work he may be feeling frustrated, horny, humiliated. For instance - you have him wear some panties whilst at work. Personally, I use the journal alongside other tasks. Every night before bed or maybe just once a week. The idea is that the submissive is being conditioned by having to write for you as part of their day.

Regarding the journal, it can either be vanilla or kinky. Hi Occhiverdi :) Glad you like the tasks. Punishments can be anything from a 'no masturbating' rule to restricted access and commication. For each task that is set and acheived, you should reward him with a sexy photo of yourself or promise of something for when you do see him. * Have him write a journal for you to read * Have him find an image online that depicts submission. You can make it easier or harder by specifying a theme (for an evening event or for day time wear) and give him a budget. He doesn't have to buy it but he must present it in word format via email with pictures and justification as to why he picked the items. * For some extra sissy play have him browse the internet and choose an outfit. * Workplace fun - sending them to work wearing nail varnish on toes or with panties on (sissy) and have him text you a picture from the toilets to prove it. You can make things harder for him by being on cam yourself. Vary the amounts and increase the intensity by having him do it on cam. They must masturbate to the point of orgasm X, Y, Z times for you and then stop completely and go on to do something else - most likely vanilla.

Sissy tasks for chastity