Weird Results Using the Transform Tool

So, in trying to create a shortcut to drawing a thick rim around a glove (like a cartoon hand), I thought I'd creat a circle, 22 Stroke Thickness, split it down the midle and then, using the tool, be able to squash it/reshape it to correlate with the angle of the glove/hand I'm drawing.

However, with either the Free, Scale, or Distort Transform Tool I get this PINCHING effect at either end of the half circle.

Strangely enough, if I cut the circle at a 45° angle, only angle I've tride, select the Distort Transform Tool, and grab the upper right anchor, I can then get something close to what I want; unfortunately, I loose the diameter of the circle and thus the proper curviture of the rim.

Has anyone else experienced this?

Is it a Bug?

Would like to hear from the experts on this phenomenon, one way or the other.

Peace,

ElementX