Cosplay

You decide that if you're going to have to dress like a girl, you're going to do it in style. You've always been a nerd, and cosplay has fascinated you since you first saw it. You've never done it, unless you count certain halloween costumes. You've looked at it before though, and masturbated to some of the cosplayers you saw online.

You search out a costume. It's expensive, at least, too expensive for someone who's broke. At least he'll pay for it. You decide which outfit you'll get, and text it to him, although he already knows, since he practically is your computer. You have to also send your measurements to the creator, and they respond with a winking emoji. You're not sure, but you think that means they've noticed from your measurements that "Doe" is a man. They asked you if you've ever worn something like this before, and when you say no, they send you a guide to crossdressing. You're surprised at how not embarassing it is to be found out. The costume maker gives the impression that it's very common. Normal, even.