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
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"
by Crazybread (thanx to Damian you know who you are) October 04, 2006
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
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
Sexual act where a man is engaging in sexual intercourse in the doggy-style position and shifts his weight on top of his partner, while keeping his penis inserted, to the point of where he is balancing on top of her with arms and legs out-stretched (not touching the ground or holding on to anything) but is still able to pump.
Man, that guy in the porno pulled a flying squirrel!
by MJizzelness August 12, 2010