Cock humiliation and Sissification (ideas needed)

[Sayuri]

Hi All,
Thanks again for all your support and advice for my venture into FemDom.
Things are going very well and my guy really enjoyed our pegging experience. I'm sure this must be normal that as we explore these kinks new ones arise.
Im sorry if there are already posts regarding this (I did do a search). My guy has expressed an interest in sissification and humiliation. I've already had him shave his legs and dressed him up in stockings and suspenders and he really enjoyed it. He wants me to sissify him and degrade his masculinity, (tell him his cock is tiny and useless etc.)

Please can you give me some ideas on how to degrade him, things I can call him. Things I can have him do when I'm not there.
I have bought a cock cage too which he can't wait to try so seems like we're getting deeper into this and I would just like some guidance so that it's enjoyable and not harmful.

Thanks again,
Sayuri

 

[paddledmale28]

Get a feather duster and have him clean while in stockings and suspenders.

 

[paddledmale28]

Paint toe, finger nails, wear make up, put a tampon in his ass during his ‘period’

 

[Blackhart666]

Now the you know the direction you want this to go
You need to teach your sissy how to do toe and finger nails
guessing he must be totally male to out side world so he can paint his toe nail nice pinks etc and clear coat his /her finger nails this will not only help with his transformation once he is good at he can start to do your
Make sure that you always refer to his penis as a clit
and asshole as boi hole or pussy
since penis humiliation is one thing you mentioned think about getting a cock cage. locking up a sissy clit dose a few things it will make them more focused on you with most cages it will force them to have to sit to pee and give you total control over their release
You need to send your sissy out or take him shopping to replace is under pants with proper panties
since you pegging your girl already get her a enema kit so she knows to clean her pussy on days you plan to use it
when you leaving her home give a list of chores you want done
when you get back praise her if you like how they were done punish if not to the standards you want
you need her in heels also
and you find a butt plug will give a nice sway when she walks
a sissy needs to learn to do make up again when good at she can do your for you a sissy should be her mistresses hand maiden
bath you help shave etc
also if you cage his clit then remember that you can use his mouth anytime
you watching tv and feel a little horny tell to lick etc
teach you sissy to cook
be trying to act female a sissy there to make your life easier
if you want more please inbox me I have trained a few sissies over the years

 

[Sayuri]

Now the you know the direction you want this to go
You need to teach your sissy how to do toe and finger nails
guessing he must be totally male to out side world so he can paint his toe nail nice pinks etc and clear coat his /her finger nails this will not only help with his transformation once he is good at he can start to do your
Make sure that you always refer to his penis as a clit
and asshole as boi hole or pussy
since penis humiliation is one thing you mentioned think about getting a cock cage. locking up a sissy clit dose a few things it will make them more focused on you with most cages it will force them to have to sit to pee and give you total control over their release
You need to send your sissy out or take him shopping to replace is under pants with proper panties
since you pegging your girl already get her a enema kit so she knows to clean her pussy on days you plan to use it
when you leaving her home give a list of chores you want done
when you get back praise her if you like how they were done punish if not to the standards you want
you need her in heels also
and you find a butt plug will give a nice sway when she walks
a sissy needs to learn to do make up again when good at she can do your for you a sissy should be her mistresses hand maiden
bath you help shave etc
also if you cage his clit then remember that you can use his mouth anytime
you watching tv and feel a little horny tell to lick etc
teach you sissy to cook
be trying to act female a sissy there to make your life easier
if you want more please inbox me I have trained a few sissies over the years

Thank you so much this is great and yes very happy to chat.
So he already had 2 butt plugs and a few satin thongs (he wears daily now) but hid them from his ex. (He said he could never tell her) I'm still quite surprised that he told me and wants to explore this with me.
I've actually been out to buy some nail polish today lol and I already have a cock cage for him but we haven't put it on yet. I've already got him sitting to pee as I knee the cock cage would force him to sit to pee. He said he felt very girly and humiliated when he sat to pee in work lol
I know he wants cock humiliation but I just want to make sure it doesn't actually psychologically hurt him. He gets a week every 4 ish months where he goes quiet and feels a bit depressed and I don't want to compound that.

 

[JacksinBucks]

Bring a male friend home & have him watch you make out & fuck him, then have him lick you clean as the bull humiliates him. Then have him lick you clean all over while the bull watches & comments. Letting this happen would degrade any man.

 

[mr smith]

Have him wear the cock cage and thong. Make him go buy nail polish for himself. Take him bra and pantie shopping and if its ok at the place have him try them on at the store. Get him locked up in a cock cage for a week and then tell him the only way out is if he gives you 50 orgasms with hos tongue. If you want to be mean you can tell him no and make him a wait a day in between orgasms. Buy him a maid costume complete with high heels ( 4 inch high or more) and make him clean the house in that outfit. Occassionally walking up and give him a spank on the ass with some sort of implement.