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1.
Similar to the motor boating, where you smother your face in a woman's large boobs, the Paddle Boating is when you use your tongue to "paddle" a girls vagina.
(Guy) "Where you going today with your girlfriend?"

(Guy2) "Hopefully we'll go Paddle Boating, but if she's on her period, it's a no go."
door sublimegirl209 29 april 2012
 
2.
(verb)

Similar to 'motorboating', a person rapidly jostles another's chest area with their face. However, in cases where breasts are too small, unsavory, or the target of the 'boating' is a male with defined pecs or gross 'moobs', this is met with the urge to throw up, cry, or play in traffic.
"I went to motorboat Joe's girlfriend but I ended up paddleboating her non-existant tits"
"I think Greg was drunk when he decided to paddleboat fat Steve"
"Chris's pecs were so hard I felt like I was paddleboating two boulders"
door Ragehound 16 december 2013
 
3.
Like motor boating, except when the girl has small boobs.
Guy 1: Heard you motor boated Susie last night.
Guy2: More like paddle boating. Chick was flat.
door MMP38 19 oktober 2011
 
4.
The extreme outdoor sport. Usually resulting in boat ramming and intense competitiveness. Builds great calf and quad muscles which usually implies the paddle boaters are unusually good looking.
Johnny: "I went paddle boating yesterday."
Anna: "Wow, I want you."
door JohnDeer 29 mei 2007
 
5.
When someone masturbates.
I had a nice session of paddle boating last night.
door Andrea E 7 september 2007