I once worked in an adult bookshop in a fairly liberal part of Sydney, we sold anything from magazines with naked ladies through to videos of naked men doing things to each others behinds. We had books about cannabis for sale next to vibrating latex blow up people.
It was a bizarre shop to be counter kid at. Especially late on weekend nights.
A few memorable purchases that caught me of guard:
(Not all have three items so apologies if that doesn't meet the question criteria)
A big black man once came in and bee-lined straight to our wall with phallic toys, grabbed the first largest blackest rubberest dong, then he proceeded to our “"interracial gay” section and quickly chose a DVD (I'll let you imagine what it was about) and then came right up to the counter, grabbed a large bottle of strawberry scented lube and placed all three items on the counter.
With his 8 feet tall hieght and huge build he intimidated me somewhat,
“"How much?” He boomed.
I quickly rang up the total, gave it to him, he promptly paid, I wrapped the items and he was off.
Needless to say I was both a bit shocked and also had no need to guess what his late night activities may involve.
A few other examples I can think of:
A lady purchased a 5 litre bottle of lube and drag shoes
Three kids bought two dildos to have a sword fight with
One guy once bought a water pipe, cigarettes and animal pornography. (I KNOW. Animal porn is illegal, but so is a lot of stuff and you can still find it- also the shop I worked at no longer exists so maybe they were caught)
A couple once bought a double ended vibrator and walked out before I had a chance to place it in a dark non see through bag. Embarrassing…
An old lady used to come in and buy LOTS of big boob porn. I really still have no idea why.
A guy used to come in once a week and buy nothing, just stand there and tell me which movies and girls he really likes for at least 45 mins each time.
Another guy was quite regular and used to buy a hell of a lot of porn but was always in a disguise(scarf or hoodie and dark glasses- I always assumed it was a councillor or statesperson who didn't want to be recognised)
Needless to say there were a lot of interesting purchases that really shocked me, but I eventually just got used it.
One thing is for certain, I am now VERY aware of just how sick and twisted the human race CAN and WILL be.