Hello Alice!!!

I have read your Q&A files and I haven't run across the problem that I have had. Here's the scenario as follows: I am a twenty-two-year-old heterosexual male. I lived in a big city. I went out to find a girl to date with. I ran into this woman who was really very attractive, long hair, dressed very neatly, and had the body to go with it. So we chatted for a while and we ended up at her place. Well, everything seemed like all systems were go. We went into her bedroom and we took our clothes off in the dark. Then we got kind of hot and heavy, and I massaged her breasts and nipples and then reached down to finger her clitoris, only to find she did not have the stamp of a female but of a male. I immediately jumped out of the bed and turned on the light and saw that she was a he. He was a transvestite. Of course, I got the hell out of there.

Now, this was just the first time that had happened to me; this happened to me two other times and I was really out of my wits as to how I could have made such a mistake. I finally did find a girl through a church group and I confided to her and she showed me her female genitals and she was very female. My question is this. How can I find out if a girl is really a female? Do I have to ask every girl to show me her sex in order to be sure that she is female? I really don't know the answer to this situation. Please help...

— Really concerned and confused

Dear Really concerned and confused,

First, a couple definitions:

Cross-dressers are people who sometimes or always wear clothing and accessories traditionally sported by another gender — it's something they enjoy. Crossdressers usually identify as their biological sex, and many male crossdressers are heterosexual.

Transsexual folks feel their assigned or anatomical sex isn't the same as the gender and related roles they identify with. Some may undergo hormone therapy and/or surgery to cause biological and physical appearance changes.

Intersex people are born with an ambiguous biological sex. The old word for someone who is intersex is hermaphrodite, but intersex is now considered more respectful. People born with an intersex condition often have surgery as infants to assign them a sex, which may or may not agree with their gender identity.

Gender non-conforming or genderqueer individuals consider their gender identity to be outside the traditional male-female gender binary.

Transgender is used as an umbrella term for anyone whose gender identity or expression is different from the sex they were assigned at birth.

Cisgender is a term that refers to a person whose assigned gender at birth matches their gender identity.

Keep in mind that not everyone will agree on these words and definitions, so it's best to use the term(s) (and pronouns) that people use for themselves. Also, gender identity is separate from sexual orientation. People who are transgender can be gay, straight, bisexual, or may not want to categorize their sexuality with a label.

Now, where did you meet these women? Was it at the same bar, or at different bars, in the same area of town? In some locales, crossdressers, transsexuals, and/or transgender people frequent certain clubs and restaurants. Maybe you've been unintentionally visiting queer bars? If this is the case, try hanging out at new places and/or asking around to find out if your future social destinations are known to host specific clientele.

Asking potential partners point-blank if they're packing a penis or vagina might turn them off and, well, it's a pretty personal question. But hey, it sounds like it worked for you already. Such a question could show that you're a progressive guy who knows that the world is made up of all different kinds of people with varying interests, identities, and, yes,... genitalia.

It sounds like you were pretty upset at your discovery that your date's anatomy didn't match her outward presentation. It might seem a bit unfair for her to not give you any warning about what was going on, but you might want to think about things from her perspective. Transgender people face discrimination everywhere, and trying to explain the ins and outs of biology versus identity is tough on a first date. And, things may have gone faster than she had planned.

For those of you who're thinking, "This guy must be a moron," don't be so cocky. Lots of male-to-female crossdressers and transsexuals can pass as cisgender. Crossdressers and other transgender people might also ask why their privates need to be made public; in other words, maybe your experiences are another reminder that we shouldn't make assumptions based on appearance and behavior.


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