This may not sound like much of a record, but where would you even get 250 chequered flags in the first place? How about on the beach at Abu Dhabi. It seems a second world record was achieved inadvertently for the greatest number of chequered flags simultaneously indulging in bondage and sunbathing.
For aspirant chequered-flag-world-record-breakers, here is a slightly easier one to go for.
Go on, you know you want to...