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Thanks everyone for your great replies, you've all been very helpful as always.
Daniel: I'm certain at this point there is a psychological element, since I can feel the worry build up even before we get anywhere. This has happened enough that now I feel tremendous pressure to perform, and that added stress certainly doesn't help in this situation. All this only adds to the fact that I do feel discouraged and embarrassed, which definitely blocks the erogenous parts of my brain from sparking. I'll try to relax and keep it from my mind. Thanks for the advice, I'll write some companies like you said to see if they help out.
Seaver: I had heard that before so I did stop/greatly reduce the amount of masturbation when I started getting comfortable with women. School and life are factors, so we typically have (read: attempt) sex at least twice a day every other day, and more on weekends. I don't masturbate in any appreciable frequency anymore, maybe once or twice a month, and even less when I have someone to do the actual act with. That's why I doubt it's a matter of desensitization.
Plan9: This has never happened to me with anyone else, so I know the capacity is all there; normally I too can gear up for the second run almost effortlessly. I believe the frustration and embarrassment of going flaccid in the middle of the act are too discouraging, and the obelisk stands no chance in the face of psychological stress. As for her, I can quite easily fit 3 fingers, so her bearing capacity is at least 4; I'm used to 1 or 2 at most. The fact that my buddy is no Behemoth himself means that this may also be a factor. I figure a different cycle of strategic positions may also be necessary.
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