Seems this has already been done - at least once.
On August 27, 2009 Abdullah Asieri, one of Saudi Arabia's most wanted men, detonated a pound of explosives apparently hidden in his rectum in an effort to assassinate Prince Mohammed Bin Nayef, head of Saudi
Arabia's counter terrorism operations. Although the attempt was unsuccessful it revealed a gaping hole in current security efforts aimed at thwarting terrorist attacks. Abdullah Asieri passed through security checks at two airports and the palace security of Prince Mohammed Bin Nayef. He then spent 30 hours in the close company of Saudi secret service agents without raising suspicion. (CBSnews.com)
The assassination attempt did not succeed but security experts have suggested the amount of explosives detonated by Abdullah Asieri would have been enough to bring down an airliner in flight.
According to Chris Yates, an aviation security consultant, the only way the explosives could have been detected is if Abdullah Asieri had been stripped naked and subject to a cavity search.
source






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