Transgender, Trans-Attracted…And…Over 50

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Once when visiting The Philippines, I spied a man –– probably in his sixties –– who was walking hand-in-hand with a woman. Not only was this woman less than half his size (and a quarter his girth), she was clearly a quarter his age.

Now I don’t have any issue with people dating whoever they want. That’s not the point.

The point is, while some transgender women may think all trans-attracted men are looking for relationships with young transgender women –– significantly younger –– there are trans-attracted and transamorous men out there who would prefer a transgender woman from the same generation.

And, guys, there are transgender women of mature age looking for guys their age too.

I know for sure this is the case, because both groups are writing me emails.

And while it’s probably ego-boosting, guys, to think about being with a very young transgender woman for the sex appeal perhaps, or the beauty maybe, listen up.  A long term, meaningful relationship that isn’t based on some kind of unstated, commercial exchange, is more likely with someone who has some life experience. Someone with common beliefs, and, likely, common desires.

In other words: someone whose stories match yours.

It’s highly unlikely a 58 year old’s and a 20 year old’s stories are going to match.

Unless, again, a commercial exchange is the story bringing two together. After all, there are plenty of older men out there willing to pay for the company of a younger woman. Including a transgender woman.

Happens all the time, right?


I’ve commented on social media accounts featuring transgender women asking moderators how come they don’t feature older transgender women.

I haven’t got a response from any of them.


I speculate mature, senior transgender women are likely too busy living their lives to post as regularly as young ones do on social media. Perhaps young transgender women who are prominent on social media find telling their stories on social media as natural. About as natural as, say a senior transgender woman sharing her stories in person.


Whatever the case, middle-age and senior transgender women’s and trans-attracted men’s relative absence online may cause these groups to think their matches aren’t out there, when, actually, there are lots of women in that age range. And guys too.

Interestingly, research by UCLA’s Williams Institute found that there are almost as many elderly transgender people as young. The study estimated that 0.5% (or one in every 200) of Americans aged 65 or over identified as transgender, compared to 0.7% among 13- to 24-year-olds.

So there are bound to be transgender women of all ages in your town.

Same goes with trans-attracted/transamorous men.

And remember, guys (and gals), you only need one.

It’s not surprising older men (and many older transgender women) who write us ask “is there anyone out there for me?”

That’s why we don’t encourage online dating, cruising social media or trying to find your partner anywhere other than in your hometown. Or at least nearby. But always in person. Because online dating can be brutal to one’s positive stories.

CNN recently featured a story about a person who is photographing and chronicling the joys and struggles of senior-age transgender people (yes transgender men as well). I loved stumbling onto this article because it confirmed for me there are transgender people of all ages out there.

You don’t have to settle. You can have what you want.

17 Replies to “Transgender, Trans-Attracted…And…Over 50”

  1. whoah this blog is wonderful i really like reading your articles. Keep up the great paintings! You realize, a lot of people are hunting round for this info, you could help them greatly.

    1. Thanks Rama. Now sure what you mean by “keep up the great paintings”, but I appreciate the recognition. yes, a lot of people are looking for this and we are helping people a lot!

  2. Im a 60 year man living alone for about 15yr.,
    But have read all about trans beautiful women
    And I love what trans love having a partner forever
    Im very submissive, love to watch movies at night and cuddle, very out going, so know in my very crazy past life, I would love to meet a trans woman and settle down for the rest of my life, just loving and being loved.

    1. Wow that sounds like me but I am very busy with my business i am a black pre-op trans woman just turned 60 i also live alone i haven’t been in a relationship in about 7 yrs i would love to meet a older man and at least start trying to settle down, plus I am a wonderful cook and love to take care of my man

  3. As a 60 year old guy it’s been difficult to find THE person for me. While I’ve had 2 trans girlfriends and must admit to a certain attraction to trans women; I just would like to find the Ms RIGHT. If she is trans great, if not, great. What does it take to be Ms Right? I imagine at least close to my generation.

    1. It’s interesting to think about what “Ms Right” actually means. I say that because there are SO MANY “Ms Right”s out there.

      The problem is, when a person tries to FIND “Ms Right”, what usually happens is they’re focusing on all the things that are wrong with he people they’re meeting. So “Ms Right” never comes along. That’s why I created The Transamorous Network. To help people like us Max, actually FIND “Ms Right”. Not keep meeting all those Ms. Wrongs! LOL

    2. The only reason I am here is information, proper etiquette and basically to not be a heal. I met this woman just in passing, beautiful and 54, I’m 59. We are at the same apt. complex and just a hey and a couple of stupid laughs. We older folks see the beauty in what young-uns see as just old. Well the conversations eventually grew over time and I asked her to lunch, where she accepted. This is when she informed me of her situation and it surprised me. I am, what I have learned through my last week of research, a cismale. She did get upset with me but whatever I did or say I don’t know but she calmed down and she actually let me walk her back to her room and I left. It seemed a little shady for the next few days and with the help of some on-line talk rooms they convinced me to just go and ask her if she likes me which I did and she did. I took her to a silly show, not many to chose from with COVID, and it included diner so we spent about three hours together and not talking about trans or cis world but just work and family. I told the girls I met someone and did not feel I should label her and just gave her name. I do not feel it is a secret but I never introduced my wife as a cis. I took a shot in the dark and invited her to a one day trip, 3hrs. one way, and join me to take my granddaughter shopping. She accepted and it relieved my tension since she would be better at this than me. Both girls really enjoyed each other while I was basically stuck on the man bench. To make a longer story shorter, people feel that they have to announce to the world of the situation. Why? And I have yet to find anyone who can answer this simple question. This was not a fetish, I just saw an older woman that I thought might be good company. It does get lonely since my wife’s passing and it scares me that I might be too forward just wanting company. Widows and widowers have issues with folks thinking they have to compete since we do keep our family photos around. They think we are creating a shrine when they are just the same ones that have always been there. I don’t see her as a label and if she feels she has to say anything it’s up to her not me. Telling me I understand, I might have been that nice guy who has bad intentions. We have only dated outside of the bedroom so I don’t know. But if we do decide to get closer then I will let you know. Does she look better with or without makeup?

      1. And so many think, past a certain age, it’s impossible to find a match. I’m telling everyone here: your match depends not at all on what age you are, where you live, what you do for a living, or even how you look.

        It only depends on what stories you’re telling (what you believe is possible). Change your stories so they match what you want and watch what happens.

        Thanks for sharing Virgil. Yours is a wonderful story.

        The answer to your “why?” is: each person lives their own life and in the living of that they are inspired to certain actions. It’s easier living your own life and enjoying what it brings that trying to understand why others are creating what they are creating. It really is no one’s business what another does. Poking noses in others’ businesses, only messes up the life you’re wanting to live.

        Have fun with your new friend. Enjoy her. Love her if it comes to that and see what comes of it for the both of you.

        1. You have very inspiring words Perry. I like how you don’t beat around the bush. It’s strange how some of the chat room (learned a new phrase not talk room) don’t want to help but cause havoc. Eventually I found the good ones because I basically just hang-up. I’m too old to worry about stupidity and I like being like you. I find enough hate in this world when they find out I vote Democrat. Keep up the good work and thanks for the great words which are far and few between these days.

  4. Sorry, but the reality is trans woman are only a sexual fantasy for most men. The media has Also created the problem because they sexualize trans woman from an early age. Just look at Dragqueen story time and the promotion of children not old enough to drive, being feminized – usually in an erotic or “over the top” way. Being trans female seems to be associated with being a perfect, georgous woman that would make any cis woman feel “ugly”. Rarely do we see the TRUE difficulties in “passing” and the challenge to meet up with internet porn, photoshopped phots and that “perfect” photo that makes her look fantastic.

    And the “rich girl”, candy girl, and Hollywood trans woman have probably spend $50, 000 in plastic surgery, implants, vocal work etc. If you think all mature woman look as flawless as Katlin Jenner, you have been misled. The fact is, most trans woman, especially mature trans woman struggle and work hard to look passable. The internet and Media has turned being trans into some perfect , flawless beauty queen fantasy. What we often are is slightly masculine looking men who sound like men. If you have $ 60, 000 to donate to me to get implants, new teeth veneers, hair replacement for my thin, masculine hairline, liposuction , lip and butt implants , etc etc etc..then MAYBE you can get the kind on non sexualize relationship the public is being led to beige is the “norm”.

    And as someone who knows many pre-op trans woman in relationships dropped by their boyfriends after their bottom surgery, ask yourself this; why wouldn’t he rather be with a Woman that looks, feels and reacts like a nature female? Your special attraction has been eliminated and your now in competion with many many more biologically correct woman.

    The trans woman rave in pop culture is a manufactured fad. All the young trans kids will discover, after the attention and party is over, after they start to,age like every other woman, and after they are now faced with double the challenges of aging woman- that of your male genetics, and that your an aging woman…well, there is going to be a lot of pain, heartbreak and depression in the future Trans community.

    So….Plan on a relationship NOT because your trans and a fad, not because you have a special appendage “situation”, not because you will be someone’s storybook wife , but ONLY because to remain male is painful To YOU ONLY and your prepared to live a lonely life to do it . Yes, there are exceptions. But make sure he introduces you to his family and friends before you “open the store”. If he has excuses, it’s for the kink and sex…and that ok too…just don’t expect a marriage proposal anytime soon.

    I would date and marry a trans woman, ( as a trans woman or a man) but I’d understand and love the person. As a trans woman who lives as male because I realize how much money it takes to look like the public and media’s view of a trans woman, I would suggest you stop selling a relationship as “trans” and simply selll yourself as a male cross dresser- that way there is no disappointment, no fantasy, no pretending- and if you find a mate who accepts that,, then even better, as a transitioned woman…oh, amd if your looking for an in emend project to make your “media -internet” version of a hot, mature pre-op trans woman- I’m your girl and willing to relocate!

    1. You’re right Kimmie about one thing: the reality IS that trans women are only a sexual fantasy for most men.

      But that reality is only “true” for trans women and other people who believe that. Like I mentioned in my last reply to your comment on our Alex Jones post, you might want to do some more reading about what we talk about at The Transamorous Network.

      There are plenty of trans women for whom men do NOT feel that way about trans women. Those women don’t need to indulge in the “reality” you’re talking about. They’ve got the reality they want. 🤷🏽‍♂️

      The media doesn’t create problems. They talk about problems people create. What people? Well, every person creates their own reality, so every person creates their own problems….So the media is not creating problems. Trans women (and trans attracted men) are creating the problems. Their own problems.

      I don’t know what “Dragqueen story time” is. So I won’t comment on that. But I will say, again, that you’re right. Being a trans female IS associated with ” being a perfect, georgous woman that would make any cis woman feel “ugly”.”

      But only for trans women who believe that. In other words, only trans women who tell that story have that experience.

      I don’t know what your point is about the “TRUE difficulties”. For some trans women there are no “difficulties”. So “difficulties” is a subjective experience. As all experience is.

      You seem to be focused on the appearance aspects of being trans. Why is that? Passability has nothing to do with being happy. Unless a person makes passability equal to being happy. If they do, then they’re in trouble. Because for that person, being passable will never be achieved. And so you see what you see in the world: many women spending so much on their physical appearance.

      That’s not necessary to be happy. A trans woman can be happy and not be passable.

      You write: “What we often are is slightly masculine looking men who sound like men. If you have $ 60, 000 to donate to me to get implants, new teeth veneers, hair replacement for my thin, masculine hairline, liposuction , lip and butt implants , etc etc etc..then MAYBE you can get the kind on non sexualize relationship the public is being led to beige is the “norm”.”

      There are a lot of stories you’re telling that are limiting your life experience. Many of them are expressed throughout your comments (both about our Alex Jones post, and about this post you’re commenting on). I understand why a lot of trans women share frustrations you’re expressing here.

      But really Kimmie, those frustrations don’t have to be both for you and for other trans women (and trans-attracted men). You can be happy. And when you get happy consistently enough, hell, many of the frustrations you’re expressing here take care of themselves. You’ll find your self having a happy life. With everything in it you want and none of what you don’t want.

      It sounds like you’re experiencing a lot of what you’re not wanting, all perpetrated at the hands of “other people”: men, the media, other trans women, society…I hear the anger…which is what happens when powerlessness boils over. It gets projected as anger towards others you may feel are responsible for your experience.

      I was just talking this morning with a trans-attracted man who is doing the exact same thing you are doing. He’s blaming trans women for his sorry life experience. Meanwhile, all that complaining just perpetrates the life experience he’s complaining about.

      You’re doing the same thing.

      You did ask a question, so I’ll answer it directly. Although you may not (probably won’t) like the answer:

      You asked: why would a man drop a trans woman after she gets bottom surgery?

      The answer is because he wasn’t honest up front about the kind of trans woman he wanted. He wasn’t willing to wait until he got what he wanted. So he compromised. And when the trans woman he was with lived her life experience the way she wanted to, she became something he doesn’t want. So he left.

      That should be no surprise. Had the guy been honest with what he wants (to himself and others) that wouldn’t have happened. But the trans woman isn’t off the hook either. She had a story going on too. One that had her meet and get into a relationship with someone who matches those stories.

      So that’s why. It’s not because she (or you) are “in competition” with “many more biologically correct [women]”. No one is in competition for anything. You create your OWN reality. No one creates it for you.

      You’ve written here a lot of complaints about life. They are your complaints. About YOUR life. Although you’re talking about others experiences, you’re really venting your frustrations about you.

      And, like with the guy I talked with today, the more you repeat these stories, the more bitter, angry or frustrated you’re going to become….

      But there’s a way out of that Kimmie. You can be happy. No matter what. And have the life you want. But not if you keep telling the same stories you’re currently telling.

    2. As a senior who’s been through the rigors of a trans woman all my life, I totally agree. You’re right on the mark. Best of life to you.

  5. I’ve been single for 13 years just can’t find a man that wants to be with me due to being a trans woman

    1. Hey Sarah. This is Perry. I’ve heart this story often. It can be frustrating to end up with bupkis after 13 years. But I assure you, with just a little shifting in the stories you are telling yourself about this situation, you can find a man who wants to be with you so fast, it will make your head spin.

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