Have you considered the SOFA(r) Swinger, the new and improved Scotz/OldFart Appliance? This is a pair of suspenders shaped to clip to the condom and hold it on.

While this still has some developmental issues to meet and surpass, it is probably still more comfortable than thumbtacks or velcro.

It has pockets for lube and a cellphone preset for 911 (just in case).

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