I think im ready for chastity and the next step

i think i want to take the next step and go in to chastity and start training my ass. i cant say i love the feeling of a dildo in my ass but i want another sissy fuckhole for use so i can get more cum. thinking about trying out anal with a condom as long as the guy promises to pull out and cum in my mouth. what do you think? i have been looking at @sissyjoyce's website sissymarket.com and could get one there, pink of course.