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I do that, too... the penis up thing. It's just more comfortable, even without sporting wood. As for the shirt... I tuck my undershirt into my boxers as well, though since I wear boxers, it doesn't come out of the bottom of the leg. As metioned above, it keep things looking neater under dress shirts and even polo shirts. My wife thought it was strange the first time or two she saw me do it, but it's just my normal thing. I actually only started doing that part a few years ago.
As for horizontal penises... that's gravity doing it's work. it's like a hinge... it can be pushed UP and it's just fine. If it get's pushed DOWN, that's like going against the hinge... and it's not pleasant. Even sideways (against the leg) is generally MUCH more comfortable than straight down. Two parts to that, as well... the hinge is one. The second is that what is down? Pants! The penis can't go through them. What is up? Space. The penis can grow about more freely. Just a thought...
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