Well, first of all, venous leakage can be caused by a variety of issues, including injury or trauma to the penis. However, "classic" venous leakage occurs from the atrophy and hardening of the internal structures of the penis, including nerves, connective tissue and so on. This is a very common battle for many middle-aged guys and the studies show low T accelerates this and testosterone therapy can partially reverse it. (Of course, I can't advice you on whether or not to go on HRT - that's between you and your doctor since it involves discussions about risk factors, your medical history, side effects, etc.)
Now there are undoubtedly other things that also contribute to this same general "hardening" process, such as AGE's, high glucose, hypertension, oxidative damage, inflammation and aging. Personally, I believe that the body can significantly heal itself if you turn off all the things that are causing injury.
As far as Pynogenol, it has been shown to help with venous insufficiency, which I think is where the confusion lies:http://www.ncbi.nlm.nih.gov/pubmed/11081989
That's a little different animal than venous leakage, although they do have some overlap. However, Pycnogenol likely helps somewhat with venous leakage as well (although I don't know of any study that proves that). Why do I say that? Because Pycnogenol lowers inflammation, improves lipids, lowers blood pressure and, perhaps most importantly, improves collagen synthesis.
I cover that in this link:http://www.peaktestosterone.com/Pycnogenol_Erectile_Dysfunction.aspx
Also, if you have venous leakage, get checked by a urologist as there are other solutions to some of the organic problems as well...