Into the Nitty Gritty of a Male of Transgender Experience (Female to Male)

No!

A huge NO I should add.

For the purpose of this article when I reference transmen I am talking about people who identify as men with transgender experience. This does not include non-binary transmasculine people.

This is my opinion and it may be controversial. People can date whoever they want. However just by definition, a lesbian is a woman EXCLUSIVELY attracted to other women. If a woman is not JUST attracted to other woman she is not a lesbian. She could be queer, pansexual, bisexual etc.

I don’t think you could be a lesbian and date a transman unless:

1. You don’t fully see him as a man. Because he was assigned female at birth it’s rationalized in your head that he is a woman and “safe” to date. If you still don’t like men or penis in some way that’s a red flag to me.
2. Maybe you also think “well he was at least socialized as a woman” so he is somehow more in touch with women. This is not fully true as I’ve met some very toxic studs/femmes in my day and they’ve shit on people just like toxic men do.
3. He isn’t on hormones or is in the earlier stages of his transition. His body hasn’t physically changed much with testosterone or surgery so his parts ideally align with what you’re used to.
4. He is still going to live a somewhat queer lifestyle.

The first 3 out of the 4 of these ideals would not be okay with me as a transgender man.

I have had top surgery, robotic hysterectomy and been on testosterone for 14 years this year in 2025. Read about my surgeries here. Scroll to the bottom of that page.

I still do go to Pride events once in a blue and have not completely severed ties with the LGBTQ+ community. However I do know some transmen personally who live stealth and have just blended into society. They live without coming out to people around them. I am not completely stealth as I’ve told the people that I’m trans who matter like close friends and even my employer/coworkers at the moment.

Talking with my girlfriend recently made me realize that when I was first setting up a date with her I only asked if she liked penetration. I never mentioned if I was going to use a strap on or had phalloplasty. If a trans-guy was out dating lesbians and he had bottom surgery that could be an issue if the woman he is trying to get with does not like penises.

Anyway I do understand that sexual orientation is fluid and can change over a lifetime. But for me visualizing dating a woman who is a self proclaimed “gold star” loud and proud lesbian would fuck with my head.

Personally I’ve dated multiple lesbians so I’m talking with some experience.

Back in 2021 I used Lex, Taimi and HER dating apps to meet women and non-binary femmes across the sexuality spectrum.

Before any interaction I would make it known that I was not a step up from a masculine woman or a super stud of any kind as a disclaimer. People would still agree to meet up. With lesbians is where I had the mind fucking going on and problematic meetings.

What I saw in a couple of interactions with lesbians are as follows:

1. One woman said ” you’re a whole man” when she chose to meet up with me and take me to her house. We did not fuck because of that. Uh yea shorty a transman is a man.
2. I had sex with another multiple times. During some of those interactions she would get weird when I pulled out my strap on. I used to ask every woman before I met them if they liked penetration so she knew how I got down. I ghosted her afterwards because sex for me is only good if it’s fully consensual. She would proceed with sex but be thinking about being fucked by a man the whole time. So parts of it would be uncomfortable for her and I could sense it. I couldn’t keep having sex with someone like that. Sex I believe should be pleasurable mentally and physically for the people participating.
3. Another gave me her number but didn’t set up dates because I found out later she’s not really attracted to men like that. This woman here could just be an example of an attention seeker. But she saw me as a man and wasn’t interested.

Those are a few examples I can think of off the top of my head. I’ve talked to hundreds of women in my life so I can’t remember every interaction I’ve had but I won’t forget the feeling of “ick” that I now have for dating lesbians.

I will acquiesce that I do live a somewhat hetero-normative lifestyle where I believe in some gender roles and embrace my masculinity. I’m sure that can be off putting for some people in the LGBTQ+ and/or feminism community.

For example I do want to be a provider man and solid rock for my family. My goal is to pay all of the bills so the woman I’m with doesn’t have to work unless she chooses. But she won’t just be sitting around. My woman will bring value to our relationship in whatever way that she can. But this talk is for another blog.

Regardless of how I feel two people of any identity can get together and love each other. As long as both individuals fully respect one another it doesn’t matter. I am sure there are examples of transmen and lesbians that successfully date. My hope is that everyone can find real love at least once in our short lifetimes.

If I was still single though I would not date any woman who identifies as a lesbian. It would fuck with my head for real. That’s my standard and those people just aren’t for me.

*If you’re looking for transition related material click here.

*If you’re interested in my Entrepreneurial endeavors, take the next step here.