Self-Made Man

2006 Book -  My Year Disguised as a Man is a book written by journalist Norah Vincent, recounting an 18-month experiment in which she disguised herself as a man—"Ned"—and then integrated into traditionally male-only venues, such as a bowling league and a monastery. She described this as "a human project" about learning. She states at the beginning that she is a lesbian but not transgender.

Norah Vincent spent 18 months disguised as a man. She relives the boys nights out, the bad dates - and what happened when she ended up in bed with another woman (The Guardian) 

In the book, she describes her experiences as a man in strip clubs, on dates, in a monastery, and as part of a men's support group.

In order to effectively pose as a male, Vincent acquired a buzz cut and flattened her chest using a small sports bra. She also hired a makeup artist to fake a five o'clock shadow and trained for months to imitate a deeper male voice. She changed her diet and exercise regime to "bulk up" with more upper-body muscle.

Vincent joined a men's bowling team, where she says "[the men] just took me in ... no questions asked." She eventually became friends with them, even coming along to strip clubs and dating women who had no idea of her true gender. She later revealed that she was actually female to the men, who "took it well."[4]

Vincent also recorded her book as a audiobook for Penguin Highbridge.

Vincent writes about how the only time she has ever been considered excessively feminine was during her stint as a man: her alter ego, Ned, was assumed to be gay on several occasions, and features which in her as a woman had been seen as "butch" became oddly effeminate when seen in a man. Vincent asserts that, since the experiment, she has gained more sympathy for the male condition, stating, "Men are suffering. They have different problems than women have but they don't have it better. They need our sympathy, they need our love, and they need each other more than anything else. They need to be together."  Source (Wikipedia) 

Also see the Guardian article entitled "Double Agent".

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I remember reading the New Yorker article back in 2006 and it was fascinating.  Here is someone who documented male privilege by switching gender. What a concept. The book is out-of-print but can be found used on Amazon. If I remember correctly the experience had profound physiological repercussions on Nora. Here is a YouTube that provide more background:

 ABC 20/20