>> So here we have a guy with a body that's pretty much "female" except for his genitals winding up stuck in a set of biking gear (spandex shorts and top) with no underwear. and it's rather obvious that he's got breasts and a penis. <<

That's quite a scene.

In addition to transfolk who can transition in various ways, there are medical conditions that may leave a person with breasts and a penis. Usually they are forcibly carved into the shape of one or the other sex, but not all of them have been.