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1.
Skydiving involves jumping from an airplane at altitudes typically ranging from 12,000 feet to 14,000 feet…freefalling for about a minute, then deploying a parachute at typically 3,500 feet…and flying the parachute to a designated landing area. Skydiving has become safer in recent years due to a device that will deploy a parachute automatically at a certain altitude for you if you cannot. Skydiving is an extremely fun sport that is challenging and is best suited for the fast thinking, mature, and open minded individual that enjoys doing things with other people. Skydivers are some of the most fun loving people you will ever meet and very few of them are “crazy”. This sport is often called "crazy" by individuals who are not open minded, live vicariously, or simply do not have the balls to try it.
Skydiving is the most fun sport anyone could ever do and you should try it...this summer!
by Joe Bates April 09, 2008
 
2.
A sexual action involving a pregnant woman and one or more male partners. The woman lies on her stomach with her hands and legs out in a "skydiving position" while the man kneels behind her. If there are multiple men they kneel in a circle around the victim. The men proceeds to fuck the living shit out of the woman in either hole, whatever the male prefers. After 30 seconds he pulls out and spins the woman on her stomach. The woman spins until coming to the next man, or the same man who then proceeds to fuck her.

A variation of this position is possible. The man across from the man screwing the skydivee shoves his cock down the woman's throat which mimics the low oxygen at high altitudes. Note: this is only possible with multiple men. Note: Possible for flamers to participate in as well all that is required is a basketball, pillow, or another similar object.
Hey Sally, your walking a little awkwardly. Is that from your pregnancy or is it because of the skydiving you did yesterday at the local bar with the High School football team?
by xRockSolidx March 08, 2011
 
3.
An activity where one jumps out of a plane with a parachute on their back and falls thousands of feet before opening their chute (most of the time without any "aggravations") and land back on the ground just as if they had jumped down from a 5MPH moving truck (again, results vary.)
White boy: I think I'll go skydiving this weekend.
Marcus: You be crazy.
by Anonymous November 08, 2003
 
4.
A modern sport involving parties, bragging, mass consumption of alcohol, sexual excesses, and on rare occasions, parachuting from aircraft.
Skydiving is about much more than jumping from a plane. You might be a skydiver if you forget to lower your voice when talking to your jumper friends in a restaurant about the weekend's lost dildos, loose leg straps and lack of penetration.
by Mike Roman October 20, 2005
 
5.
An activity viewed by most as suicidal or crazy. Those people are just too chicken shit to do it themselves.
Guy 1:
Jason blaw blaw might forget to pull his chute while skydiving

Guy 2: Grow a pair and jump before pretending to know anything about it.

Guy 1: Yeah, I just looked like a real retard for saying that. I wish I had courage that didn't come in a bottle.
by A Sky God August 27, 2009
 
6.
getting high by hitting a homemade parachute; the highest you will possibly get

Originated in the 301: DC metropolitian area, adapted in St. Augustine, FL.
yo, u tryna sky dive?

No wonder yo ass is baked as shit son, you've been sky diving.
by KingMePLZ September 19, 2009
 
7.
Muff diving when you're high
Did you hear about Pat? Yeah, he smoked for two hours and then went sky diving on some unconscious whore he found in the street.
by Paul Daniel December 06, 2006