Q. I was wondering if there are any issues having to do with transporting sex toys on an airplane. I need to bring a few along on a trip to visit someone who needs a bit of punishment. ;)
A. In order to avoid to prevent the likelihood of emptying out your clamps, whips or dildos in front of security staff - and the hundred or so people behind you in line - leave it all in your checked luggage.
Since most airlines prohibit travelers from locking their suitcases, pack your checked baggage securely. Hard suitcases are great for travel because they can withstand potential rough handling; they're also less likely to rip, which prevents your special items from falling out or getting damaged.
Pack items in plastic Ziploc bags or see through containers. If you're taking battery operated devices, make sure to remove their batteries for the journey. If you're dead set on keeping the batteries in their chambers, cut and place small pieces of cardboard so as to interrupt the circuit. As a last resort, insert batteries the wrong way in, but do so for each one; many toys can still turn on even when one or more batteries aren't functioning.
If you've got rechargeable sex toys, reload them up in advance and bring the charger along. It's a lot easier for these ones to accidentally turn on by themselves, so if it came with a travel case now is the time to use it, especially when you bring them into the plane cabin with you.
Many manufacturers produce sex toys that are disguised as inconspicuous objects such as lipstick tubes, rubber duckies and so on. Although they seem the least likely to raise suspicion, leave these in your checked baggage too.
If don't want to risk your favorite pieces going missing from your case, bring them along in your carry-on luggage, but prepare an explanation in advance in case one of your pleasure/pain paraphernalia gets flagged in the x-ray machine. You can crack a wry smile if you think it'll help your cause but nonetheless, be confident and straight to the point, "They're for sex".
Unfortunately, there's always a chance that your stuff may be confiscated if it's perceived as a threat. So to avoid a sour start to your vacation, leave the heavy artillery (e.g. handcuffs, sharp items, steel objects … you get the point?) in the safe confines of your home.