This Part of The Vicarious Woman Six-Part Series will not be my strongest suit because I stopped reading crossdressing and transitioning biographies several years ago.  And I know that there have been several good ones in the last several years.  I hope some of you will strengthen this wiki-bibliography with their favorites in the comments section.

I’ll start off with one classic that is not even in print any longer; but if you can find a copy in a library or used bookstore, you might want to try it.  SECOND SERVE is the memoir of the transitioning of an eye surgeon who was also a world class tennis player.  It’s an early example of the experience of transitioning while already a person in the public eye (not unlike Caitlyn Jenner).

A better written classic by a famous person, though, is CONUNDRUM.  It takes an author with sharp observational skills to be considered one of the best travel writers of all time.  (Don’t even think about going to Venice without reading one of her Venice books.)  But what happens when the “travel” she is recounting is her own transition: you get one of the best written transgender memoirs ever:

Similarly, if you want to find a place where brilliant “political” scholarship meets a “personal” story of transition, try Diedre McCloskey’s CROSSING.  A much-published, brilliant scholar and tenured professor at the University of Illinois’s storied economics department in Chicago, Ms. McCloskey’s account of how “the system” and her own family tried to interfere with what she saw (and believed as a world-famous libertarian) as her inalienable rights over her own body to transition as she pleased is fascinating.  I never fully agreed with her libertarian arguments that, to me, discounted too much established protocols like the “Benjamin Standards,” but the history of how she had to battle to become her true self makes for fascinating reading:


Another professor and prolific author has become probably one the best (certainly most famous) advocate for transgender rights.  Her books, her regular columns in The New York Times, and her common appearances on talk shows (and as a regular part of the Jenner television posse) are all deserved because she thinks, writes, and talks so well.  Her original book on her transitioning has become a standard, a seminal memoir of transition: SHE’S NOT THERE by Jennifer Finney Boylan:   (An interesting aside: I once had some extended correspondence with Ms. Boylan.  I think I was wrong in my arguments at that time.  I had shortly before read McCloskey’s book and felt her pain and admired her fortitude in her strained relationships.  But, in my opinion, in SHE’S NOT THERE, Ms. Boylan all but brags about how well she managed her relationships as she came out and then transitioned.  At the time, that management struck me as terribly manipulative especially as to keeping alive her marriage to her previously heterosexual wife.  We argued back and forth about it a few times; and finally agreed to disagree.  Now, nearly two decades later, that marriage and family is still successfully whole.  In short, then, I guess I was wrong: her wife made her own considered decision: and it seems to have been the right one.   I would love to hear the opinion of other CDH members who have read SHE’S NOT THERE on this point.)

 I’m not exactly sure why I am so put off by Helen Boyd’s success at making a whole career, a whole mini-industry, out of the crossdressing and then later the transition of her husband: books and websites and speaking engagements, etc.  Nevertheless, I guess, her books cannot be left out of this bibliography:   MY HUSBAND BETTY: and SHE’S NOT THE MAN I MARRIED:

Another fine memoir of a crossdresser has already been reviewed by Erica in CDH.  Erica’s essay on ALICE IN GENDERLAND is erudite and a great read in itself; it is here:  The book, itself, by Richard Novic, MD, can be found on Amazon here:

I started this essay with the disclaimer that I’m out of touch on this Part of the series; but I do have one that I have on my must-read list.  The reviews have been fabulous; and I will get to it soon.  It’s a biography of one of the stars of the hit television series Supergirl, the transgender actress and activist, Nicole Maines.  BECOMING NICOLE by Amy Nutt tells Nicole’s story, along with that of her family, including her identical twin brother, Jonas.  (Identical twins usually have to be the same gender, right?!?!); but what happens when the are not:

I do hope that my CDH sisters will enrich this wiki-bibliography by telling us in the comment section below about their favorite CD and TG biographies, autobiographies and memoirs.

(From Brina, Managing Editor: Cassie has again given us a glimpse of what could be and what is tasteful. That is what is expected when commenting. You may list those you like, but as before any links will be deleted. I have neither the time nor the desire to police inappropriate postings. I sincerely ask for your cooperation. Thank you!)


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Cheryl Ann (Cassie) Sanders

Currently sliding from senior citizen into elderly. Dressing for almost 60 years, but rarely in last dozen. Fairly famous TG author, usually under one of two pen names (Alan Barrie or Cheryl Ann "Cassie" Sanders.) Many books in Lee Brewster's classic publishing line, Mardi Gras Press. And a long-time bestseller on Amazon, A WOMAN'S PASSION. (Those sales were eclipsed in recent years by all the $2.99 tg junk writing on Amazon; however, I recently got back the publishing rights and arranged for an inexpensive Kindle Edition and sales have picked right back up.) Also just added a new Kindle Edition of an old nugget to Amazon: THE SUNDAY GAME by Alan Barrie. Although always closeted to my family, I used to travel heavily for business, so had a lot of time to dress. Back in the day, could pass easily even in places like a White House tour or a hotel bar. Have been to a couple of the New England groups first events at Provincetown, but, again, not for a few years.

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Gianna Bonita
Gianna Bonita
3 years ago

Thankyou for this series. I have read over 20 books on Amazon Kindle over the past two years. They are so much more affordable as a download to a device as compared to the paper version. Also, the shipping costs from USA to NZ are outrageous. I encourage all ladies to explore transgender material on Amazon it’s a huge resource to access. At the moment I am reading, How To Not Know You are Trans by Bethany Beeler. Published in 2019 so it’s quite recent. It’s a different take on the subject and personally, I found many comments in it… Read more »

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