The ultimate homosexual sexual conquest. This is where a gay man seeks to have sex with a straight man because of its almost impossible nature. The Holy Nail can be two things. One, it's the journey and desire to have sex with a straight man. The other is the actual act of having sex between a gay man and a straight fellow.
Loren: "Gay guys really want to do straight guys. They're the Holy Nail."
Shelby: "So gay guys like to do other gay guys?"
Corrine: "Yes, but they would rather do a straight guy. You know, the Holy Nail."
Matthew: "Damn, you see Fred over there? He's looking fine tonight."
Seth: "Yeah, too bad he is with his girlfriend."
Matthew: "I know! He's my Holy Nail."
Keith: "If I finally nail a straight dude, would that be considered a Holy Nail?"
Caitlin: "Not sure, because if he has sex with you he might be gay."
Keith: "Yeah, then it wouldn't be a Holy Nail."
Shelby: "So gay guys like to do other gay guys?"
Corrine: "Yes, but they would rather do a straight guy. You know, the Holy Nail."
Matthew: "Damn, you see Fred over there? He's looking fine tonight."
Seth: "Yeah, too bad he is with his girlfriend."
Matthew: "I know! He's my Holy Nail."
Keith: "If I finally nail a straight dude, would that be considered a Holy Nail?"
Caitlin: "Not sure, because if he has sex with you he might be gay."
Keith: "Yeah, then it wouldn't be a Holy Nail."
by Noullet776 November 30, 2013

by fiddlepop August 25, 2013

An ex-girlfriend/boyfriend that a person still has sexual relations with.
Originally derived from the italian "Vecchio Chiodo".
Originally derived from the italian "Vecchio Chiodo".
by Detective Scrote March 3, 2009

*ass nail*; pronounced (*ahs*)-(*nael*)
The occurence of being fingered up the anus too vigorously by another individual (or by yourself) where a shard or a whole nail is left behind inside your anus.
The occurence of being fingered up the anus too vigorously by another individual (or by yourself) where a shard or a whole nail is left behind inside your anus.
by DreyAndLanceTheAwesome. January 28, 2010

Anything that contributes to an early death, particularly....
(N.) Cigarette, usage pre-world war I and still continuing today.
(N.) Cigarette, usage pre-world war I and still continuing today.
by Kung-Fu Jesus June 21, 2004

I really need to nail someone tonight, it's been so long my balls are the size of oranges!
or
Yes! I finally nailed Jane last night!
or
Yes! I finally nailed Jane last night!
by Saffer77 April 13, 2014

Lesbians have short nails to have sex ;)
I mean it would hurt if they wouldn't have short nails... I guess
I mean it would hurt if they wouldn't have short nails... I guess
Boy:,, omg do u see her short nails?Those are lesbian nails!! That's why she rejected me! I'm dumb !! "
by Laurapaupaura July 16, 2019
