2 definitions by Cafetero
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 26, 2009
Sex act. When you put a crown on your partner and perform anal sex until they ask for help, then you turn the around, make them call you their hero and take your reward... anal sex.
by Cafetero October 1, 2019