The Teddy, or Armpit Hold - Straddle is a great trick to incorporate into your routine as it demonstrates strength and ability to hold your body weight without the use of your legs...you basically are using your upper body, core and hip to hold yourself on the pole. This looks awesome performed aerially, also.
There are a few basic steps to performing this trick:
Gripping the pole with both hands in baseball grip, release your legs and get your hips in front of the pole.
The pole should be in position between your inside arm and your rib cage in the start of an Inside Arm Grip.
Holding onto the pole with your outside arm and simultaneously creating a grip between your inside arm and rib cage, reach with the inside arm to hold the inside of your thigh (of the inside leg)
Start extending your legs out, toes pointed
Once the inside arm grip is secure, leg go with your outside arm and reach down to hold the inside thigh of your outside leg and splay your legs apart.
Hold the position.
To get out of the position, extend both arms out holding your hands together, one on top of the other, and hold them like this while you extend your legs out straight in front of you, feet together, toes pointed.
Let your legs go down first then your arms hold the pole and slide down.
Remember, your hips need to be in FRONT of the pole
You can use your outside arm to hold the pole until you are strong enough to hold with just your inside arm
There is also an "easier" way to perform this trick: Reach behind and hold the pole with your outside arm and 'recline' on it while you do the trick. This supporting arm takes some weight off of your armpit hold until you become stronger and used to holding with that part of your arm
You can start to learn this trick by extending both of your arms out in front of you, grasping your hands together and then start lifting your legs a little at a time, even if its only inches off the floor at first, until your grip under your inside arm gets strong enough to hold your weight (See the video below)