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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."
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When someone masturbates.
I had a nice session of paddle boating last night.
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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.
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When someone works your sack like a punching bag, but with their feet, while you piss in their face (displaying the spurts of water that accompany paddle boating)
"Dude, you think the Dutch Rudder kicks ass?? Wait till some chick gives you the Paddle Boat... with cashmere socks on."
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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."
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Placing you face/head between a woman's breasts and manually slapping yourself with her breasts.
Hunny my tits hurt from last night paddle boating adventure
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To perform oral sex on a woman. Specifically in a fashion to make her fall madly for you due to your 'paddle boating' skills.
Your Friend: "Why is she still obsessed with you even though you broke up 3 months ago?"
You: "I gave her the pink paddle boat before we had sex for the first time. It kept her coming back for more."
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