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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
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
The act of squeezing the last glass of wine from a wine box.

In these tougher times, many of us are drinking Box wine, and there is always one more glass in the box after the normal process or using the spout/nozzle

Rip open the Box (use a a fire starter) and flatten out the plastic bag. Grab all four corners with the spout pointed down....Looks like a flying squirrel.

Drain out all the remaining wine to the spout/nozzle and pour into glass.
How are we doing with that box of Wine - "Looks like we are going to need a Flying Squirrel"

No more wine ? "No, I used the last, had to Flying Squirrel it"
by 007professor007 April 21, 2010
a girl is laying down on the bed and the male jumps on her injecting his penis into the girls pussa
Guy 1: Did you hear about the flying squirrel?

Guy 2: Ya. I did the flying squirrel last night and she was squirting acorns.
by XxCrackBabbiesxX October 15, 2011
Simply wack off with a window open, find your target, aim down and try and launch your shot and hit them right in the face. If you succeed then don't look back.
The flying squirrel can be done in almost any second story building and is extremely mean but hilarious
by ModzZilla March 29, 2010
A counter-rape tactic, in which the victim lies in wait in a spiderman-style pose, arms and legs spread, on the ceiling (on the underside of the top bunk of a bunkbed, etc.) above the rapist's bed. When the rapist returns to his/her sleeping area the victim lets out a battle cry and drops from the ceiling like a flying squirrel. Counter-rape ensues.
Anna always said that if someone raped her, she would flying squirrel their ass.
by gingerscholarbusinessman December 22, 2009
When you are cut off from the trail snowboarding and CRASH! into a tree.
At Dodge Ridge Odis cut Megan off the trail and she did a flying squirrel into a pine tree.
by Odis DeHart February 28, 2007