i've never purposefully planned or orchestrated the embarassment of any girlfriends i've had, but a number of them have embarassed themselves, sometimes while i'm there, sometimes while i'm not and i just heard about it.
the most memorable wad definitely a girl i was dating who worked at a photo developing place (this would've been just before digicams became the norm). i'd taken some nude photos of her and she developed them herself at work and somehow, even though you'd think she'd know this better than anyone as it's her job, she left the photos in the machine and forgot about them, where they were of course discovered by a male co-worker who proceeded to let the other guys working there in on it. he ended up being fired and she quit out of embarassment, and i had to hide how turned on i was when she was telling me what happened...
another time involved a different ex who was into some mildly kinkier things. let's just say this particular enf involved bondage, a revealing outfit, and a roommate coming home unexpectedly a day earlier than planned from her trip, with her boyfriend and friend in tow, and i'll leave the rest to your imagination...
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