My senior year of college I took a class called "American Narratives of Passing" and as part of that class, I read Stone Butch Blues, and an article by Sandy Stone called "The Empire Strikes Back: A Posttransexual Manifesto." This book called those two pieces to mind.
In her article, Stone critiques some previous pieces and memoirs written by transsexual and transgendered people. Some of her issues include that the narratives "reinforce a binary, oppositional mode of gender identification. They go from being unambiguous men, albeit unhappy men, to unambiguous women. There is no territory between." Stone also suggests that the "authors replicate the stereotypical male account of the constitution of woman," such as "fainting at the sight of blood." In some ways, Stone Butch Blues fell into the same trap, in other ways it did not.
What I really enjoyed about Boylan's account is that she doesn't have a definite moment of "now, I am truly a woman." While she feels that she is a woman her whole life, when she begins her transition, it is faster than expected but still gradual. There is a long period where she can go back and forth between man and woman, and depending upon who is around her, she might be identified as either. Additionally, as an English professor, Boylan has perhaps more tools to truly reflect on her actions. She recognizes that she starts acting in oddly stereotypical feminine ways, to the annoyance of the women around her and herself as well. She admits that perhaps her desire to suddenly lose five pounds was a way of trying to belong. She also compares transitioning to puberty - even though she is over forty, being a woman is still new so in ways she acts like a teenager, taking time to paint her nails and other things that her wife has long since moved on from. Boylan even addresses some of the issues with other transsexual/transgendered memoirs, and states this as a reason that perhaps some of them can occasionally seem a little adolescent with certain descriptions.
As she says, it is difficult to find a balance, describing some of her activities:
Had I been born female, no one would remark upon these things - but since I was not, any masculine affect is considered a vestigial link to a previous life; conversely, any feminine affect that seems excessive can be hauled out as evidence that I, like Morris, have arrived at middle age just in time to be fourteen years old. (247)
It was an interesting story, and Boylan herself shows that in many ways she was fortunate - her background and her family support her through this and while I'm sure she glosses over some of the more unpleasant issues (for example, her sister refuses to speak to her), for the most part, she seems to have had a lot of support with her decision, even if it was painful for some, such as her wife. Additionally, as she herself states, since she works at a liberal college with a focus on diversity, she didn't need to be as worried about losing her job, and could afford to get the transition done with the best care available.