Help me start my sissy transformation 19M
 

Hello. Recently I've started embracing my sissy side more and more and I'm asking you all for help. I currently don't own anything in terms of clothing or toys but am willing to purchase the things necessary. One thing to keep in mind is that I don't live alone and thus visible clothing dares won't really work.

Please aid me by giving rules and tasks for me to complete. I'm currently away for a few days so the posts can build up and I'll get to it as soon as I get home in a few days so if you don't get a report immediately, that'swhy. Pics for things like crossdressing/shaving/bodywriting can be requested.

Are you a sissy or are you trans? Easy way to know is to look into gender dysphoria
Just saying bcc you worded that weird

Removed the last line which might have been the culprit haha. I'm a sissy, not trans

Bumping this.

Cmon give this sissy some rules and tasks uwu

Well lets start with obvious rules:
- Keep your body smooth at all time. Also, no facial hair allowed!
- Buy a chastity cage. Wear it all the time. You may only cum once a week after you have been following the rules perfectly.
- Buy 7 pair of panties (mix styles and colors). From now on you may only wear panties
- Buy a dildo and lube. Get used to fucking your ass 10 minutes every day.
- Spank your ass red every night before you go to bed.

Thank you! This all seems very reasonable. I've ordered a cage, a dildo and an assortment of different panties (actually got 14 haha). Everything will hopefully arrive sometime next week. I'll make sure to shave and start with the spanking even before then uwu

You should also throw out all your men's boxers, underwear. You won't be needing them any more. You may save one pair, but whenever you use them, you forfeit your week's one orgasm.

Also, practice your deepthroat game. 10 minutes daily.

Destroying all you male undies is important indeed ;).
Another thing, prove that you bought cute girly panties might be fun. When everything arrives, make sure your shaven and wear your chastity belt and model all panties. Hold a paper with your getdare username and make pics of the front and the back. Upload them to an album. This way we know in which undies your prancing around all day everyday ;)

Will do, as I said above, they'll arrive sometime next week probably