Essentially, the "rick roll" of sex positions. It is done from the missionary position, although can be managed from doggy style, by extending arms and legs outward in the position of a flying squirrel or a skydiver. Upon doing the "flying squirrel" you must scream "FLYING SQUIRREL" while balancing on your mate. This has been known to stop sex immediately, ruining all chances of a climax.
"this is going to feel great...FLYING SQUIRREL!!!!!!"
-end sex-
by Special Ops Squirrel October 01, 2009
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Stretching your scrotum and balls over a person's face, and laying your penis on their forehead, resembling a flying squirrel with its arms spread. Done properly, this will cover the person's mouth and nose completely. To create a good suction, make sure your balls are warm before proceeding. Injury can occur if the person was sleeping and wakes up being suffocated by your massive nuts and sac.
"Dude, Candace passed out so I gave her a flyng squirrel. She woke up totally choking on my sac!"
by Mugatu-san October 08, 2004
The "flying squirrel" is: grabbing ones testicle bag with the tips of ones fingers (both hands), and stretching the skin into the opposite dirrections. This should resemble a flying squirrel. Your "flying squirrel" is best displayed for people when tightly pressed against a glass window or door typically found in computer labs or a lobby of a public building where there is lots of glass pannels.
"Ohh my Gosh you know that crazy guy Jake?, he pulled a flying squirrel in computer class"
Sex position, when the female in on her stomach while holding her ankles with her knees fully bent. The Male holds her knees up while spreading her legs, to hit it from the back.
While executing the flying squirrel Andrew got rug burn on his knees and Nicole got it on her face.
by Andrew D. July 16, 2006
Sex position in which the female is sprawled on the bed, face up. The man stands up on the bed and proceeds to wrestling jump on her, aiming for the vagina.
I totally flying squirreled this bitch last night. I missed the first 26 times, but it was totally worth it.
by grass itch November 13, 2014
When your left testicle is stuck to the inside of your left inner thigh and your right testicle is stuck to the inside of your right inner thigh. As a result your testicles resembles the image of a flying squirrel's arms spread far apart with your scrotum and its skin being the skin on the flying squirrel's arms that droops down.
This happens often when you have been sitting down for a long time (like on an airplane or cramped bus/car) and your thighs, testicles, and scrotum start sweating and since you're so cramped and your legs aren't spread far apart, they adhesively stick to both thighs.
Person 1: Wow we've been sitting on this bus for 8 hours.
Person 2: Yeah both of my testicles are sticking to my thighs.

Person 1: Yeah me too, I've got the worst flying squirrel right now.
Person 2: Yeah I wish I could stand up and pry my testicles/scrotum off my thighs.
by yallreadyknowduke April 06, 2015
Humble, but stunningly talented. Starts off on the ground, but reaches impressive heights.
At first, I wasn't very interested in the job, but then I found out that the company is flying squirrel.
by Clara Anderson April 19, 2011
A penis trick where the erect penis is tucked firmly between the legs far back into the ass-crack in a spring loaded position. The legs are then opened with a flourish and depending on the turgidity of the member, a satisfying slap is heard against the belly.
Watch out for that flying squirrel boys...whhapppp.
by Sansastic May 11, 2010
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