I’m 39 years old and for the first time I’m considering dating a man as a woman. It is a little intimidating if I’m honest. I’ve dated men before, of course, but always under the label of gay or gender non-conforming, this is my first time entertaining a relationship as a woman, just me.

I tip-toed into coming out as trans, first I admitted that I liked men, then that I didn’t feel like a man, more like a woman, then I came out as a woman, shedding the mask of masculinity and showing my true self, Ruth.

What’s odd about this guy is I know it’s not going to work. I tell him so. He obviously doesn’t like it when I say things like that but he also doesn’t work to change that viewpoint either. He’s a player. He hates it when I say that, but it doesn’t mean it’s not true. I’m okay with him being a player. Oddly enough, when I call him on that and tell him he’s not boyfriend material he reacts in strange ways. He opens up…

He goes from a smooth talking hottie to a vulnerable adult. And it is SUCH a turn on. I like him best in those moments. For instance, he’s admitted that he’s worried that once we…you know…that I’ll leave. That confused me, a lot. I have had to ask him why does it matter because he’s a player, I’m the perfect match in that regard. Hit it and bounce, everyone’s happy. But apparently that’s not the entirety of his character.

I’m not one to use anyone. I find him attractive sexually, physically, and mentally. But just as soon as I begin to melt that icy heart I’m so famous for he seems to be kinda smug about it and begins to talk once more about his I’m both a “girl” and a “friend” but not necessarily a “girlfriend”. Always followed up by a comment about how attractive I am. He’s good, I’ll give him that.

I don’t mind simple, uncomplicated sex. So long as it’s completely healthy, sober, consenting and well communicated…let’s have at it. But I get a little insecure when the other person does what this guy does. I legitimately cannot tell if he’s playing a game to hustle me in some fashion or if he’s just trying to have sex or if he’s just reserved about his own true feelings of attraction. Perhaps my transness is a bigger factor than he let’s on.

I don’t know. I do know this, I expect nothing. Just chill. I try not to think about it too much. He’s fun to flirt with, cook for and call him my man. He calls me beautiful and affirms my body as not only mine but sexually desirable, attractive and that feels good. He calls me smart and encourages me while at the same time finding me attractive.

Okay, so maybe this is a little more complicated than I’d like to admit and that I’m just a bit beyond my comfort zone. Okay, I’m in my own proverbial deep end. I know that I have no expectations but I do have hopes. IDK.

To help support or share in my release, please visit my gofundme created by some unusually wonderful folx in the community at:



With Love