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The word nailing is another word for picking up a one night stand.
For example you are out with the boys on a Saturday night at a seedy Irish pub necking stubbies with the boys, it's about 2 am and your toey as a Roman sandle. Your standards are very weak at this time and you settle for the easiest target which is usually a larger girl, an older one, or one with red hair and many freckles. Once you have picked up this fine young lady you then take her back to your mates and give her a good nailing, once done you send your mates a text message saying nailed.
Nailing by Victor Small September 11, 2005

Nailing 50 yarders

Secret gay code for engaging in Coitus with old men.
Ian is really feeling himself. I heard he’s nailing 50 yarders every weekend.
Nailing 50 yarders by Haywood Jblome November 12, 2020

Nailing the shingle 

When you are getting a blow job and right when you are about to finish you smack her on the head like you are nailing in the last shingle
Stacey is so good at BJ’s that I thumped her on the head, like I was nailing the shingle on a roof , just so she knew how awesome she was at it.

nailing jello to a wall 

What Shreya does when she's not surfing couches or committing domestic terrorism
Shreya: "Did you see that, I was totally nailing jello to a wall just now"
Judge: "Ma'am you're facing six life sentences"

wet nailing 

the act of performing intercousre in the bath/shower.
fancy staying in. get a take away. and let me do some wet nailing on/in your sweet little arse.
wet nailing by scottie massive January 25, 2009

Like nailing jello to a cat.

The ultimate in complexity and difficulty. This is a combination of two other analogies:

- Like herding cats
- Like nailing jello to a tree
"Getting the House of Representatives to agree on a topic is like nailing jello to a cat."