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10
The longest chastity of my life has begun
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So the wife is leaving today for vacation. She’ll be gone for 9 days. I have been instructed that i will be in chastity while she is gone (shes leaving me with a key). I have been given strict instructions on when and under what circumstances i can unlock. Every other day i am allowed to unlock to clean myself. I have also been given a window of time next week that i can pleasure myself but if i want to cum is the real question for me. Part of me wants to actually pass up on the opportunity just to see what happens. But if she said i am allowed to cum, will i be punished if i dont? In the past when Ive literally failed to cum(i tried for over an hour once while we were having sex and STILL failed!) she locked me as a result, “since i couldnt cum i obviously didnt need to”. And oh god the shame if i attempt to masturbate and cant make myself cum and then she extends me beyond the set end date.

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6 months ago