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Mary from Long Island Blog
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Some time ago, there was a blog run by a woman calling herself "Mary from Long Island" (presumably suburban New York City). She had a son in his late teens (legally an adult, but still fully dependent on her) who had some severe behavioral problems. When he crashed her car due to his recklessness, she had enough. She and her daughter put him in a chastity device and began feminizing him. His punishments also got very severe. After a brief period of resentment the son settled into his new lifestyle and became very obedient, doting, and a good student. The blog later included some statements from the son who defended his mother and claimed that chastity, feminization, and strict discipline were what he needed, it all worked for him.

I of course don't know if all this was fiction or not. The blogger did get some hate mail and eventually the blog went private and seems to have disappeared. Perhaps someone here saved a cache or knows where the blog is today.

I think that a good percentage of boys really do crave a rigid structure in their lives (that's why many join the military) and also do enjoy beauty, femininity, and would rather seek the approval of a woman than conquer one. Or play the cat-and-mouse courtship ritual game of wooing and being approved, rejected, and approved again at an exercise that has no real rules and no real measure of success. Women who have firm expectations and set rigid rules can be very desirable, and I think some boys feel that way (I did), even at very young ages.
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