Mmmmmm monie, it sounds like you could be a regular guy on either side of "straight & gay" street. LOL
Have ya ever thought of dressing as a guy in that fantasy? Perhaps telling your gay guy friend you need to slip into something else and walking back into the room moments later
dressed in jeans, boots, a black and red checkered flannel shirt and wearing a white baseball hat? You may need to wear a tight sports bra to get the flatter chested look of a guy.
Consider getting dressed up like this in the day time on a pretty day, and having a guy you know with a nice pick-up Truck to allow you to pose around it "lookin macho" like the proud guy who owns it, where some digital photos can be taken for you(best at low resolution). Get the best cutest guy pics you can get and take them over to:
Lesbian Personals Online
or any of the other personal's like it where you can join free and upload your best photo and describe your fantasy. Just to see what kind of response you could get. I'd bet you would meet some people who share your taste in fun and fancy.
I used to post a girl friends photo at LPO just to meet and cyber with bi and lesbian women when I was learning to write as a natural and convincing bi/lesbian female character. I stopped when I had this one woman to beg me to hook up with her and come live with her. She claimed to be a lawyer
and her kids had grown up and found work and now wanted to be a full time lesbian....with ME.(or the photo she thought was me) ....oops I did it again.
eDJ