Message: Anal Only With Trans Girlfriend

Steven: Hello. First of all, thank you for all your work, I’ve been a big fan for years. I’m seeking advice. It’ll be a bit long, and quite peculiar to explain…

I’m a 32yo male who’s been into anal for a long, long time (my first time at 16yo was anal, we had no condom and no birth pill, and it’s been my favorite way to fuck ever since). Four years ago, I met a girl through a dating site. Both our profiles mentioned “anal only”, our mutual pictures pleased each other very much, and we got a very good contact through chatting. We met at a bar and connected immediately: she’s smart, funny, extremely sexy and feminine, classy. She offered me to go to her place (you bet I will), and we jumped at each other as soon as the door closed.

When I got to her last layer of clothes, I had two surprises: she was wearing beautiful backless panties and a jewel plug in her ass (yum), and there was an unmistakable bulge on the front of her panties – a small bulge, yet one which shape was very obvious… I had previously never slept with a Tgirl and it wasn’t something I was particularly seeking, but I’m open-minded, I loved absolutely everything else about her, and I hadn’t been planning to do anything with her crotch anyway – my attention was focused on everything else, particularly her beautiful ass and its beautiful hole…

We had a very intense and wild night, so good in fact that we spent the next day together. Two months later, she was selling her apartment and moving to my place. Four years later, here we are, still a couple, and enjoying the Hell out of it.

During all this time, you have to understand we never, ever talked about what she used to be. All her appearance, behaviour, friends, etc. indicate she’s always been a woman. Even her parents (who love me, I have the “ideal son-in-law” type) never mentioned it, all the pictures they keep of her show a cute girl. In our everyday lives, she always wears something that hides her crotch – she has a very large assortment of backless panties to wear during sex (and jewel plugs to go with it). She never touches her crotch during sex, and I certainly don’t. The only thing that may happen is that she cums in her panties without any stimulation while I fuck her (sometimes she cums even while deepthroating me), and that rather turns me on (it has no consequence, I can keep fucking her as long and as hard as I want after she cums, and I generally do just that).

So, it’s been quite a shock when she talked about her past for the first time last night. She’s been brooding lately, which is unusual for her, so I asked her if everything was OK. She answered that when she started her transition (!) years ago, she swore to herself she would be a complete woman at 30yo. Now, she was 29yo, the only missing thing was to turn her genitals into a pussy (from what I understand, her balls stopped producing hormones years ago), but she wasn’t sure she wanted to get a pussy any more: I’m anal only, she’s always been anal only/ignoring her genitals (and loved it that way), and she didn’t feel like going through a long and painful and risky surgical procedure to get something we wouldn’t use anyway. But on the other hand, she did promise to turn into a “complete woman” by 30yo, and she still wanted to be one, so she didn’t know what to do.

And then, she asked me what I felt about it. I told her it was a very complex matter, and I needed some time to phrase my feelings correctly.

To you, I’ll say what I feel very bluntly: the idea that she gets her cock and balls removed pleases and turns me on a lot (much more than I thought it would), but I’d rather have her keep those if her alternative is to get a vagina and clitoris instead.

The thing that makes our sex so perfect is how obvious it is: from the very start of her sexuality, she ignored her genitals and focused on her ass, she’s completely disinhibited about it (for example, from day one she does ass to mouth like it’s the most natural thing in the world, it doesn’t even feel naughty). That makes her ideal for my own sexuality – there’s only one hole to fuck down there, nothing on her front to act as distraction, no orgasm but anal orgasms, we complete each other totally. Her getting a vagina and clitoris would ruin that balance: either she doesn’t use them and what’s the point, or she does, and it breaks what she’s always been and what we are.

I’d rather have her keep her boy genitals, which are so much smaller than mine that it actually arouses me. I thought a lot about it, and ideally, it’d probably be the best for her to get a “fake pussy”: no vagina hole, no clitoris, but no cock or balls either, just a stylized pussy shape that’d be a lot simpler and safer to build surgically. That way, she’d be at ease in a bathing suit/if she has to take a shower naked in front of people, and she could feel more like a “complete woman” (which, frankly, she already is to me), but without breaking our balance. I would love that very much. But I don’t know if it’s legal/where to get that safely, and how she’d react to my suggestion.

And another thing: do I have the right to tell her how I feel? It’s not my body. I’m just her boyfriend, and we only know each other for four years. Who am I to decide?

Everything I read from you make me feel we have similar views on things, I think you can understand me, and I really could use your opinion. Thanks!

Ultimately, it’s her body and she has the right to do what she wants with it, but she’s also asking your opinion. I think you should be honest with her, but preface your thoughts by saying that most of all you want her to do what she wants for herself. Tell her that you love that she is anal only and that she doesn’t have anything else to get distracted by. Tell her that you think she’s wonderful the way she is, but that if were to change, you still would want to stay anal only with her. You could even tell her about the idea of a decorative but nonfunctional vulva as a compromise, and see what she thinks about it. If she likes the idea, then she could start talking to surgeons who perform such procedures and see whether it’s an option.

Be honest, be open, and be supportive of her. Try to just have a good, healthy conversation about it together and listen to each other. Good luck, and let us know where you end up.

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