>>2661182In my personal experience it happens naturally over time once you're consistent with chastity and keep using your hole frequently. When I only did chastity occasionally I could make myself ejaculate handsfree while fully flaccid if I went at it really hard for a long time. Now about 2 years later it happens much quicker and with much gentler stimulation, meaning I can do it more than once before I get exhausted. It also happens pretty consistently with real cocks now instead of only under the perfect conditions like when I masturbate. I don't mean that squirting from anal is the end all be all btw, but because it's hard to quantify otherwise it should at least give you an idea.
If you maintain peak sexual tension without having your cock available for relief, your body will be eager to learn and adjust to getting fucked and over time will start activating the muscles required to take anal from feeling good to feeling amazing. After that it's about strengthening those muscles further, so I definitely recommend kegels as well but just getting fucked more does the job too. Mindset also plays a major role. The simple fact is that anal can feel incredibly pleasurable but the nerve endings in your hole just aren't the same as in your dick. The better you're able to distance yourself from what stroking felt like, the more steadily your progress will be in finding more pleasure from the feelings of stretching, contracting, warmth, depth and fullness.
Let me know if you have any specific questions, I don't wanna go too hard on the walls of text.
