Well-Dressed #118
You know, I’ve been thinking…I always get asked about long-term male chastity, and I’ve always felt like a month is the longest period of having a guy locked up without orgasm that I would be able to stand, mainly because I love having sex and would want to have my holes penetrated, etc. But, upon further thought on the matter, I think I could probably push the max chastity time to 3 months, under a few conditions. He would be giving me lots of oral sex. For his health and safety, as well as my personal enjoyment, he would agree to periodic prostate milkings, either by my fingers or a toy. He would need to present himself to me on all fours, nude, on our bed for nightly inspections of both his caged cock and his ass. And, most importantly, he would need to learn how to use a strap-on very well, as he would need to fuck me whenever I needed to be filled and still be able to maintain his chastity. As long as I’m having orgasms and having my holes filled, several months of having my sub locked up actually sounds rather…enticing.
Tying him to the bed and ball gagging his mouth shut to keep him quiet while I edge him. Then pinching his nose shut every so often just to see him panic and start to struggle against his restraint. He’d look so cute doing all he can to fight back and I’d love to watch his eyes get all big and scared and watery the longer I hold it shut 🥰
https://i.redd.it/qwb9ww3pkeb91.jpg
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