In theory you might have it easier with the strapon on your head. First of all it covers your face..to some degree..unless you are wearing a non-satisfactory strap-on...secondly..it separates you from the crowd..so people might ask "Why the hell are you wearing a strapon on your head?"
Come up with a great comeback and you might be in. Keyword in this is having a sense of humor I guess. Right now I'm quite tired and non-inventive but...
"It's national penis-celebration day, why arent you wearing one? Ehh never mind, I know you celebrate it on the inside
Let's grab a drink..but since I'm wearing the penis on penis-day, you're buying.."
"I didn't find a hat that matched my outfit better, what do you think? Looks good on me tho, don't it ? "Well then you take me to a store they sell better ones, right now miss, and we'll talk it over there..."
"All the women I ever meet only want me for my penis, so I figured..if I put in on my head at least I get eye-contact..seeing as Im currently talking to you eye to eye..guess it works, lets grab a drink while you are still able to focus up here..."
"I'm actually a secret agent, this is my disguise..you woulda never guessed I was a secret agent would you, wearing this ? Nuh-uh...oh man. now I told you too much, we need to grab a coffee before someone sees us talking together"
.::: ______This is my world now_____ :::.
.:::_____D____A____M____O____N_____:::.
~Fight for your freedom or die enslaved~
~Lemming, Fft, Blue Wing, Viking, Nomad~