Chastity and orgasm denial discussion

member_4873d3336c · 2026-08-31T11:55:45.000Z · 0 replies

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member_4873d3336c Member Thread starter
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2026-08-31T11:55:45.000Z #1

Hi everyone,

Recently this boy tried for the third time to milk himself off for his Mistress, aiming to keep everything in good shape. The issue is that despite prior experience, he hasn’t managed to make much real headway yet. He can usually get a decent initial leak at the start of the process, but that’s mostly it.

He has experimented with a small plug, a medium-sized plug, and even his own finger to properly stimulate the prostate. Often, near the beginning of the routine, he feels that strong urge to pee, which is typical for effective milking. However, after that first drop, essentially nothing else happens. Sometimes he can build up another urge later in the session, but it doesn’t result in any more leakage.

Does anyone here have experience with this? Whether you milk yourself or do someone else? This boy would really appreciate any advice or insights on how to improve, as he is finding it quite a struggle right now.

Cheers, Penny’s Property

member_2d998cb471 and member_c8510e65b2

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