To grab a person from behind by surprise, bending the person over and apply anal sex, consented or non consented. Commonly used as a humor comment rather than the actual deed. The term derives from men being raped anally when introduced to a correctional facility. The term evokes on male on male rape and violent anal intercourse. The term can also be applied to women.
"When i finally caught up with Joey I jailhugged him so hard I doubt he will take my tv without permission ever aain."
by cafetero June 25, 2009