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Transitioning from Straight Male to Lesbian

Transitioning from Straight Male to Lesbian

I have always loved women.  Their beauty and grace, their connection and compassion, their communication and loquaciousness are all qualities that I have greatly admired.  My mother is a strong feminist who worked hard years ago for the Equal Rights Amendment.  Her women friends in the League of Women Voters that I met were singular in that most had a specific look of intelligence in their eyes that pierced my consciousness.  I wanted to be all those things, too.  The challenge was that I was assigned male at birth.

I was socialized as a male during my childhood and any transgression towards the feminine was quickly discouraged by gender police; those in society that force adherence to a gender binary: male vs. female.  The sexism that values male behavior, yet devalues feminine behavior is acutely felt by male bodied persons who express “feminine traits.” Feminine boys, cross-dressers, gender non-conforming male bodied people, male-to-female (MTF) transgender people face intense disapproval from many in society if they stray from the gender binary and show their feminine side.   Our society does not like deviation from the binary gender norm.  Stern looks or language from a parent, a teacher, a classmate usually attempt to stuff that incongruous feminine behavior back in the closet.  Transgender people face rejection, verbal abuse, increased suicide rate (41% have attempted suicide), job loss, homelessness, physical violence and even murder.

I could only fantasize about becoming female.  However, in real life, I learned to function as a male during my youth.  Growing up in conservative Utah during the 1960-70’s, there really wasn’t any other choice.  I began dating women in high school.  I dated as a straight heterosexual male. I loved the soft kisses of the women I dated.  Yet I felt self-conscious and acted passively as a male in initiating relations with women.  Eventually, I learned how to make love with women.  It felt so right to be intimate with a woman, but despite this pleasure I had discomfort with my male body.

Decades later, after trying to suppress my feminine side with psychotherapy, seminars, and self-hypnosis I became increasingly depressed.  I took estrogen periodically, rather than continuously, so that I could maintain sexual relations with my girlfriends, yet indulge my increasingly strong drive to feminize my body.  Confessing my gender incongruity to my girlfriends resulted in break ups.  I had hoped my last relationship would survive gender transition, but my girlfriend was heterosexual.  It was just as unrealistic for her to changer her sexual preference from heterosexual to bisexual, as it was for me to deny my internal female gender identity.  In 2005, I finally decided to embrace my feminine gender identity and see where that led me.

I transitioned openly from male to female in March 2011.  I am fortunate to have a supportive family, open-minded friends, an enlightened chairman, and live in liberal Seattle with a large LGBT population.  My transition has gone exceptionally smoothly and I have had no problems with my colleagues.  My depression has disappeared.  Unfortunately, a success story like mine is often not the case for those transitioning on the job, with many transgender people being let go.

Interestingly, slightly more than half of MTF transgender women are attracted to men after their transition.  The remaining are attracted to women.  Many are also bisexual.  MTF trans-women may be attracted to men both before and after transition.  Some MTF trans-women were married as men, yet appear to change their attraction from women to men after transition.  Some don’t.  Is this fluidity in sexual preference or suppressed bisexuality?

So here I am today: a lesbian transgender woman.  I have zero interest in dating men.  How do I date other lesbian women?  What are the dating rules in the lesbian community?  I didn’t know!  I have a few lesbian friends, but I did not delve into the LGB culture until recently.  It is new learning curve that I am negotiating.

I’m learning about the gender spectrum within the lesbian community:  lipstick lesbians, femmes, butches, dykes, etc.  Many lesbians prefer a gender polarity of female vs. male energy in their relationships.  For example, femmes dating butches seems to be the norm. So how do I as a femme lesbian transgender woman attract a femme lesbian?  Can I date cis-gender lesbians (women born women) or should I date other transgender lesbians?  Is there a bias by cis-gender lesbians against dating transgender MTF lesbians? How can I meet other lesbians?  Do I go to lesbian bars, organizations, meet-up groups or try on-line dating sites?

It’s a work in progress…

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  • Hi Bobby. The story of your transition sounded very familiar to me, and something like that forms the basis for the fictional transition of my character Tazio in “Sarah, Son of God.” I am not trying to peddle my novel to you, just letting you know that there is a story now being widely read by lesbians (and others) of a beautiful man who became a beautiful lesbian — in Venice, of all places. You can Google it if you are interested. Good luck — and good friends — on your difficult path.

  • Ann Soucy (West) says:


    I loved your story and personally have no less than 40 Trans-friends either FTM or MTF; I applaud the courage of you and every individual who walks this path.

    I am a Queer woman in Connecticut and see you as a gorgeous woman of today. I’ve visited Seattle several times and have friends in the area; I wish you all the best in your search and know that while it can be challenging, it can also be incredibly rewarding. Good luck!

  • Susan says:

    I am a pre-op lesbian transwoman living in Salt Lake, and I identify strongly with your story. It’s been over six months since my “heterosexual” marriage fell apart, and though I’m not looking for a new and serious relationship, it would be nice to go out with a woman, develop a friendship, and maybe even experience some physical and emotional affection again.

    I’m very stable in my career and life. I’m very easy to get along with. I think I have a lot to offer a woman, but like you, I’m not sure where or how to develop a lesbian relationship. I can’t seem to find online dating sites. I pass as a woman very well, so I’ll have to disclose… and I’m not sure how or when is the appropriate time to do so.

    Complicated and frustrating, isn’t it!?! The awkwardness doesn’t end after transition, it just changes. What I am certain of, however, is that having a relationship with a woman AS a woman will be 100% better than muddling through a heterosexual relationship as a “man”.

    Good luck!!