I have in the past for 2 reasons.
1: You don't have to worry about cleaning up/ catching the spooge.
and 2: Since condoms have been associated with sex from a young age, even putting one on is kinda sexually exciting.
I don't do it often, but it's kinda fun when I do.
He only used 1-2 condoms by himself and was incapable of cheating (in every sense). We only had one pack at home and they had expired, I had even suggested that I'd buy him condoms for masturbation so that he wouldn't use expired ones (he didn't use them again since the discussion). There's just no point using them to improve sex when you don't use them during sex. Plus, he hated condoms, couldn't keep an erection with them and didn't use them with his ex either. He had also mentioned that "they made him feel small", probably because they were the wrong size.
I just happened upon this forum and thought I might give you some info. I also masturbate with condoms sometimes. By making it slightly less sensitive, I not only prolong the act, but also help with future problems. You see, if guys masturbate a lot it can decrease sensitivity in the penis--sometimes even leading to minor ED. By masturbating with a condom, it limits this. If he then has sex without a condom, it is more sensitive than masturbating (which is almost impossible if he's masturbating wo a condom). A hand can always conform better than a vagina or anus, so this way he can masturbate but still keep the real sex sensation as the highest point, perhaps sustaining his erections.
Clean-up has been mentioned several times, and it is definitely a plus.
Finally, who cares if he's using expired condoms for this? An expiration date is important so it doesn't lead to breakage during intercourse, but for masturbation, it doesn't really matter. Use up the expired ones that way, and save the others for real intercourse (even though you're on birth control--you may find he lasts longer).
Its all good.. I would not worry about it.
My now ex boyfriend uses one because its less messy he said. But he likes it better with out it
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