Dating a Transgender Woman

In response to the popularity of this topic and these beautiful women, I have spent some time researching issues that affect transgender women and the men they are involved with. On this post I’ve featured some points-of-view from men who have dated or who seek transgender women. The quotes are from the Tevolve Network, a comprehensive site that is an excellent resource for anyone interested in the subject. (Some of the quotes have been edited for clarity.) For many men, for a number of reasons, a loving relationship with a transgender woman would be a match made in Heaven. Bear in mind, for those who would prefer a pre-op transgender woman, many of these ladies are eagerly awaiting the day they can have genital reassignment surgery. They would want the man they love to be supportive.



Note: Why these women are posing for these pictures, I wouldn’t know. I do know these images offer a glimpse of what transgender females look like. I also know they are beautiful and fascinating creatures. Obviously, the vast majority of transgender women, like most everyone else, would not pose nude on the Internet. However, it’s nice that these girls do.

From the guy’s point-of-view:

1. For me, I’ve recently just got into transgender women because of past situations with supposedly normal women(who turned out to be crazy or had some really big axe to grind) and I’ve found them to be pleasant, fun, and very sexually accepting in regards to being just as sexually aggressive as i am. and its funny but i never did once challenge my sexuality,lol. It’s like “um normal women can be dangerous, transgender women are fun. Let me try them out for a while.” Haven’t had a problem since.

2. I have found in my own trials and tribulations as a young man looking for what interests me in a romantic side is that transgendered women quite honestly make it easier to communicate or clarify how you’d like to date or pursue a relationship then if you were dating a genetic female. I’m a fan and respectful southern gent of the feminine prowess but seriously why is it that so many genetic girls make it harder to be able to communicate or understand what they’re issues are?! In retrospect I will say that it;’s always a great date for me to enjoy the company of a young woman who likes a respectful chivalrous guy to take her out cause that’s how it should be! Unfortunately I feel that with today’s society, the idea of the Audrey Hepburn styled ladies of old are a passing breed!

3. I have never been interested in men and don’t consider myself gay although I have always felt comfortable around gay men. I have always been attracted to sexy effeminate women and am now attracted to sexy effeminate TG (pre-op). In terms of personality, sex, everything else; I just love TG… I still consider myself heterosexual, however my woman has a penis and a wonderful personality to go with it.

4. I am married to a woman who is ts. We have been married for 3 months. We had a ceremony with family and friends where we exchanged vows. It was really beautiful.

So, the great question…..why? Well nobody asks, why did you marry a genetic woman so why ask the question of a woman who is ts.

We met and we clicked. We just had huge chemistry. I could not help but love this wonderful woman. When she told me she was ts, I didn’t think anything of it. I loved HER for who she was. I love her for who she is. Gender, sex or whatever has never come into it. We love each other and that is all that matters.

5. I believe trans women are very in tuned to who they are.To make that choice is a major decision in their life and shows who they are and want to be.I respect and applaud that.I would love date a trans woman.I’ve seen some beautiful trans women.I have no problem with my masculinity,and fully aware of who I am.

6. I’m a transgendered woman who’s really frustrated because I really don’t know where or how to find a boyfriend my age., or age group. I’m not into bars, and I want to find a man who isn’t looking for another man. I’ve dated gay men before and it’s not the same thing. A gay man wants another man. That isn’t me. I want him to be the man, and I’m the woman. If I go as far as being intimate with him and taking his cock inside me, I don’t to be rejected after e go to bed simply because he really wanted a man.

7. Your sexuality chooses you, you don’t choose it. You can ignore it though.

I always wondered why I wanted to have “gay sex” but wasn’t attracted to men. When I was growing up there wasn’t such a thing as a transsexual or shemale. There were transvestites, drag queens and cross-dressers. All these were obviously men dressed as women.

Advances in science and technology have allowed transgendered people to feminize their appearance permanently. Since the late 90s I have realized that I am “tranny bi”. I am innately attracted to the feminine form and I’m happy if that form has either a pussy or a cock. If I like her I will accept whatever she has downstairs. Most trannies used to think that guys like me were gay and couldn’t come to terms with it. When I say I’m tranny bi they think about it and realize it’s a new sub-sect of bisexuality. I’ve never had a t-girlfriend but would love to find one.

8. I have dated several trans-women, all non-op and am currently in a serious relationship. As others have said, it just feels right for me. It never quite felt right to be with women or gay men for me. I’m straight, acting and feeling, pretty much, no cross-dressing or autogynephelia tendencies, as seems to be common among one segment of trans-oriented men.

I like that there is a little yin in the yang of some trans-women. I prefer a penis to a vagina. Am I bit gay? Maybe, but different. The women I liked, were athletic as another commented here. Beyond the sexual aspect, I just adore the expressiveness of trans-women and enjoy the company and friendship of quite a few. I’ve nothing against post or wannabe post ops, I can also fall for them, as they share many of the characteristics I find attractive, but it’s just not my preference so I doubt I’d date one as I wouldn’t want to hurt her. However, love can outweigh our sexual preferences. No one is perfect and love is about appreciation and acceptance, not perfect buns and so on.

9. Why do I find transgendered women so attractive? I hadn’t actually asked myself that question, it was something mainly subconscious.

Maybe some information about my own sexuality is in order here. I’m bisexual, I’ve been sexually attracted to both men and women since puberty, although it happens a lot more with women. Whether this preference is natural or a result of “cultural conditioning” is something I don’t know. I don’t ponder too much on it. I am what I am and enjoy my sexuality to the fullest. Because of this, I’m afraid I fall in the “men who like transgendered women are bisexual” category, as someone else put it here. ?

I first came into contact with transgendered, pre-op women through transsexual porn, like so many men I guess. I know I was dumbstruck. It was like a sudden revelation, a world beyond the vanilla male-female divide. Suddenly, there were girls that bridged that border, that combined both male and female elements in their physique. To me, such a woman was like a dream come true, a focal point of all my sexual fantasies.

So, from a selfish point of view, transgender women – and I have always seen pre-op transgender women as 100% female with “additional allure” – to me are the ideal sexual partner. A transgender woman to me is someone with whom I can be completely sexually satisfied. I would be able to live with a partner that offered the very cliched “best of both worlds”. (A horrible expression, I know)

Of course this is a fantasy. Only a minority of girls is comfortable with still partly masculine aspect. Experience has taught me many girls do not consider their status such a blessing as I do. Their male genitals are an unhappy reminder of their condition and they’d rather you don’t insist on it too much. I also understand men like me who find them attractive for this are seen as strange, even perverted “chasers”. I’m not a mind reader, but I always feel I make them feel less complete. (Whereas I consider them “more complete”, to put it awkwardly)

Finally, what I see as this “bonus” can never be the basis for a solid, long-term relationship. Sure, it’s an added attraction to me, but in the end, you fall in love with someone for the person they are. So the fact whether your transgender girlfriend decides to go for SRS should not affect the love you feel for each other.

10. As a man who does prefer TG women although also dated and married natural women I think reasons include:

Yes TG women embrace a feminine side in a way that natural women don’t – natural women seem confused about their own feminine side and want to play it down to complete with men.

I do love the shared secret that my partner is TG – if we are in normal environment

I think one of the great attractions of a pre op is that unlike a natural woman you have a obvious physical signal of when you partner is aroused and when she has an orgasm.

Also see Accommodating Women

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7 thoughts on “Dating a Transgender Woman

  1. I have had the privilege of dating many beautiful woman in my life. Contrary to what most women say, a larger penis is high on the list of preferred attributes for a man to have. When alone and after a couple of drinks, most women will admit me they just dont want to commit to a man with a small penis. Life is to short they say.
    My current TG girlfriend (my first and perhaps last) is more understanding of being born with a condition you have no control over than any woman i have ever know.
    My advice for any man: consider a transgender girl. She is simply a woman who was born in a male body, and is working her way back.

  2. Feeling so late to this….Thank you for this information. I am divorced man that feels a complete enlightenment reading this information. Thanks, hope I am not too late to read info. post 2013! Thanks again.

  3. You guys are just dumb. I am dating a transgendered girl(2+ years now) and they, well at least my baby, don’t like to be sexual objects. If you do that, then you will never find love(with one). You should remove the nude pictures author. Sure, you can get off to them, but the purpose for your post is null and void, especially when you are seeking to date one.

    Similar to what the author said, my experience was unique. My first experience with a trans girl was random. I met her online in an anime art forum. We talked for months and around the 6-8 month period we began to talk on the phone. She began to tell me about her problems at home and I would try to alliviate her pain. Around the 1 year mark we started exchanging pics and then I found out she was trans. That was the first time I ever knew about trans woman. This girl was extremely passable, I didn’t know about her being trans until we exchanged nude pics and I saw something weird with her panties. Before that I also thought that trans girls, like the author posted, were merely men who dressed in drag. You can imagine what happened to my brain when I first realized that men can undergo a hormone transition and look just like a girl, if not better. We continued talking for several more months and I ultimately lost contact with her ( I was 17 when I first met her and she was 14). I found her again when I was 19 after she contacted me by accident and she had just turned 17. She remembered me and we talked again, but I was dating another girl at that time.

    I never re-approached her. I had found her online 2 years later and found out that during the time we had lost contact, she became an escort and cam girl which turned me off. I lost all respect for her. Haha, now you are wondering where the hell is my story about my current trans girlfriend. Well my relationship with the previous girl failed. I was a full time college student and worked full time. The girl I was dating didn’t like my heavy work schedule and we broke up. I got back into the dating scene shortly after but this time I tried online dating. I found 2 girls, both black. 1 was an old high school friend that I had a crush on. We went out a couple of times and it turned out she had a boyfriend, so I just stopped talking to her. The second chick was also a random encounter, but was trans!

    When I found my baby I was merely giving her depression advice(I had been in 2 previous depressions). I never expected that from my simple advice we would continue talking and ultimately falling in love with each other. I knew she was trans, but the reason why I wasn’t weirded out was because of my previous encounter with a trans girl. My girlfriend is so cute and she’s been transitioning for 3-4 years now. I am so freaking lucky to have found her. She has a super cute face, a really nice body and a really cute voice. She was born with a high pitch voice and her voice is so feminine. Not to steer off topic, but just imagine a very feminine voice during an orgasm. She makes me go crazy with her voice. One advice I can tell you guys is that if you approach a trans girl with a biased view on trans woman you will be put down faster than it takes you to blink. Both my baby and the previous trans girl always got offended whenever I mentioned the word tranny or shemale. Those words have negative sexual connotations and I always got my ass chewed whenever I mentioned them or implied them.

    Trans girls/woman are born with a gender identity disorder that makes them feel like girls stuck with boy’s body. They always feel like woman and like to be addressed like one. The second you mention anything about their private areas, such as if you could-you know-suck her off, she will slap you! They don’t like that crap, well at least my girl. If you want to experience that, then I suggest letting it happen naturally. Like during sex, but do not ask for permission or mention that you will suck you know what. Just do it and chances are that she will be orgasm’ing and won’t care. They like to be treated like woman though, even during sex. Do not forget that! Do her like you would a woman. Oh and a straight trans girl will never “DO” you, they only like to be “DONE”. That is a huge turn off lol My baby let me know what to do and not to do with her within the first couple of months, that was one of her NO NOs. Not like I am into that, but I have read a lot of comments on youtube and porn vids with guys posting that stuff.

    OMgawd, I just wish you guys could experience that. I don’t typically like to express sexual stuff since its private, but it is so crazy when I sweet talk to my baby and/or kiss her and I see her panties bulge up. That is a huge turn on to me, when I know that she is going crazy for me I just begin to undress her and kiss her. She grabs my junk and I grab her boobs and butt cheeks. I feel like I am going to orgasm just from that. I never felt like this with other actual girls. Not that they don’t turn me on, its just that with a trans girl you know when she is horny when her panties bulge up. With a regular girl you have to pleasure her with your hand first before they go crazy. Once my girl gets hard and knows I want to do her she grabs my junk and just knows how to play with it. Its not like the porn though guys. Do not immidiately get on your knees and expect her to put her stuff in your mouth. Ain’t going to happen. You can’t always get her hard/aroused all the time. Because of the hormones trans girls take, sexual urges are much lower than a guy’s.

    Sorry for expanding the above paragraph, just thought I’d share a quick story. One day me and my girl where sitting on a bench talking. I kissed her and told her that she means so much to me and how I am all hers. She got really hard and made me touch her down there. I told her “no, don’t get horny here in public”. Suffice to say that the second we got home she threw me in bed, undressed me and just started to ride me. She came on my stomach and it was so crazy. She rushed me to get home that day because she just couldn’t get soft. LOL

    Lastly, don’t be a douche! Do not feel intimidated or make her feel like you are too scared to let people know/learn that you are with a trans girl. Some trans girls are very passable and are hard to identify, others are not. My girl is very passable, except maybe with her feet. She’s kinda big for a woman. Hold her hand and make her feel like she is your world(important to you)! Hug her and kiss her and tell her you love her. And for future purposes, some trans girls have a goal to fully transition and have SRS, so embrace that with your girl.

    I have been with my baby for 2+ years and I would very much love to marry her someday. Sure we fight sometimes but we love each other so much that we always forgive each other. I wish you guys the best and if you are lucky like me and others, don’t be foolish and lose her. Trans girls, especially those seeking only love, are extremely hard to find. They are like diamonds or the next purest rare element.

  4. extreme beauty. They have been blessed with free life – being who they are and want to be. I wish I could be as courageous. I love you all – thank you for your love, hope, beauty and freedom. Love you always…Peace – Bill

  5. They are lovely and exotic, and as they offer what some may see as the best of both worlds, I don’t know why anyone would not embrace them fully as the treasures they are.

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