TS Dating Gude

America's Foremost Transgender Woman


A Woman’s Greatest Fear: Will my transgender girlfriend end up wanting a man?

Received more than one letter from born-woman now in love with a MTF transsexual gal. Noticed a constant concern over their love’s potential future shift in sexual orientation.

Additional chapters Included in This Section Include:

Natural Women Attracted to Transsexuals
Lesbian Women Attracted to Transsexuals
Women Who First Fell in Love with the Man Before Transition
Problems for Women Dating Transsexual
Trans Love Concerns: Will She End Up Wanting a Man?
Transgender Lesbians: Trans Women with Trans Women

Lesbian Transsexuals

Following is a letter I received from an adorable lady in Phoenix regarding her newfound love and related concerns regarding her transsexual partner.

I address each of her issues - and opportunities to improve matters - in the sections that follow.

Letter from a Woman in Love with a Transsexual Female

Hi Renee,

I hope you had a great weekend! It was warm and sunny here in Phoenix. I took my girlfriend Madeline on a hike yesterday, and it couldn't have been a better way to spend a day. I attached a photo... two very happy girls! (Madeline is on the right)

I found your article titled Problems for Women Dating a Transsexual Female. It's been one of the few pieces I've found on the internet talking about women dating trans women. Thank you for writing one of the few pieces that I can relate to!

Everything you state in your article is absolutely true. I can also add a lot more to the list, if you're ever interested in hearing my perspectives.

The issue that weighs heavily on my mind is whether being in a relationship with a man is ultimately what Madeline needs to fully feel like a woman... as in, it would be one of the greatest sources of validation to her that she is a woman (and after that, having children with a man).

Sometimes I wonder if she's with me because before she transitioned, women was what she was used to. So by staying with a woman, she's staying in her comfort zone. Also, I wonder if she's staying with me because she hasn't yet gotten the bottom surgery. She knows there are very few cisgender men that would be comfortable getting in bed with her right now, when she has both male and female parts. I wonder if after GRS and she is finally passable anatomically as a woman, if she will want to start dating men. Where will that leave me? Potentially heartbroken and feeling used.

Do you have actionable advice for how we can work through this concern? One idea that I've had is to keep the relationship an open one, and allow ourselves the option to date others. This way the heartbreak wouldn't be nearly as painful if what I described previously was to come true.

Thank you for reading and listening,


Answers to Questions and Concerns About a Lesbian Transsexual

Dear Tatiana,

Wish I could answer your questions with simple yes and no responses, alas - almost every issue is dependent upon other circumstance.

Post-Op vs. Pre-Op Transsexual: Which do most men prefer?

Let’s clear up one big misconception: a pre-op transsexual usually has 1,000X more straight male dating opportunities than post operative transsexuals. Surprised? Yeah, leave it to straight guys sexual leanings to put a twist in every scenario. Do me a favor: please read my article about
women wondering if their husband is gay is she she finds out he likes shemale porn. The number of straight men drawn to pre-operative or non-operative TS women is astronomically high: and there’s just not enough to go around who are passable, not a prostitute and into men. To a large segment of those same men: a post-op TS is like a car with a flood title: they're not eating anything extra and still have to explain to their family and buddies why they chose a chick who used to be a man. A post op female must be extraordinary to secure a high quality guy: kind of like Carmen Carrera. Pre-op? Much easier!

Now that we have that straight?
Let’s move on!

Transgender Lesbians: What Makes Them Tick
Transgender Sexual Orientation
By and large, most people’s sexual orientation doesn’t change - even with gender transition. If you’re wired to women - you tend to stay that way. Wired to men? That sticks. Like both? A bisexual transgender woman will tend to find herself with lots more opportunities to explore bisexuality than ever before. Alas, the fundamentals don’t change.


Particularly with trans-lesbians - that absolute determination of sexual orientation isn’t always a straight line - no pun intended! Almost every TS lesbian woman
explored with men - at least a bit. It's only natural. You already observed one reason: a sense of validation of their womanhood. Alas, that’s but one reason they’ll struggle with a final decision of being lesbian for life.

Reasons some transgender lesbians end up with straight men
Not enough suitable female partners: Not every trans women is highly feminine and attractive in their new gender. Some lack confidence and sex appeal. We’ve all seen those that act and dress inappropriate as women. Lots of these same trans women struggle finding appealing female partners. Some trans-girls - while most attracted to women: struggle with the “Who does what?” in such relationships - both at a dinner or in a bedroom. Additionally, about half the lesbian world is completely vag-driven in their choice of mate - add in cultural, race, geographic barriers? The candidate list gets smaller and smaller. Considering the fact there’s usually a ton of straight guys knocking on the door? Some gals give up the lesbian path out of sheer frustration.

It's easier to live a straight life. We just spent our whole childhood knowing we were different, tried to muster courage to face this demon. Before we know it - we’re a gender queer: nobody is sure exactly what we are: stick out like an oddity every day. We finally push past the endless challenges off changing our appearance, rebuild our life and family relationships, get our career back on track - and now? We’re going to endure fresh sets of public stares and comments because we’re lesbian? For some - this journey makes them even more devout in the drive for personal standards. Others get tired of being different: crave traditional for once in their life.

Female validation: You mentioned this aspect in your letter and I agree: it’s a real issue - until it's not. What do I men by that? New trans women can be liked to teen girls: learning their feminine empowerment from the attention and accolades of men and boys. Usually, every girl learns being beautiful comes from the narrow tunnel of true-love: not sex appeal. Sadly, they usually learn this important lesson through painful experience. It’s a short term concern: not long term - since the problem is based in a lie.

Gender nuances in the face of a lifelong struggle: There’s also the male-female relationship nuances that lesbians and gay men must sort out: whose the male-role on this issue, whose the female character in that project? Having waited her whole life to become female? Having to share that femininity sometimes feels frustrating. A dear TS girlfriend of mine was on vacation with her female partner and lugged three heavy trips worth of weighty luggage to their car upon departing the hotel. On her last trek back to the room - a man who had been watching by the pool commented: “You need to find yourself a man to take care of all of that”. When she made her way back to the room & found her girlfriend doing those final room checks for remaining items: she went off on her. It was one of many such arguments that eventually doomed their relationship. Nowadays? My dear friend is happily married to a lovely gal whom she cherishes.

What changed for my old friend?

First, she explored and discovered that were lots of things about loving and dating men that didn’t work for her. Second, she become more secure in her femininity over time. Finally, she owned her lesbianism. Embraced this - is who she is and thus, become more willing to share various aspects of masculine and feminine roles without a sense of loss.

What Lesbian Transexuals Often Hate About a Potential Male Partner

As discussed, there’s lots of reasons why a transgender woman might end up with a man. Alas, there’s a bunch of equally compelling reasons she won’t: assuming her orientation is mostly towards other women.

It’s all about him. The biggest shock and adjustment trans-women often face when dating men is the what every straight female long ago embraced as gender reality: it’s all about men - the relationship, the sex, where its all going, what you’re doing. For a trans-woman that’s only dated women? This is often the biggest cold, hard reality that sends them running back to females.

Slender hips and a hairy behind: Male and female bodies are different: duh! Sexual orientation is rooted in these differences far more than the genitalia aspect - hence the number of straight guys that are drawn to highly feminine pre-op TS women. A gay person at heart and orientation rarely finds the same joy and pleasure touching a body outside their predisposition. One trans gal I know summed it up like this: “If I came upon five way-hot nude guys and one average-looking naked girl seated across a room: my eyes would always first land upon that average chick. When I realized that? I realized I was wasting my time trying out men.”

Putting-out on demand: The concept of feeling pressured to provide sexual attention as a prerequisite for relationship satisfaction -is a new experience for a woman, who was once a man. She’s more accustomed to being on the other side of that fence. Conditional love pressure - in this arena is a new experience. Some such trans-women detest this aspect of straight love more than all else.

Some girls don’t enjoy anal: Here’s an interesting irony: few trans-woman don’t get at least somewhat turned on by imagery of a straight guy screwing a tranny in her booty. Probably a role-validation thing: not quite sure. However, some gals discover its not a source of great pleasure in real-time. My old friend Clarissa explained how she was beyond aroused by such imagery: even ended a long-standing love with a woman to pursue it without conscious. The first encounter? “It was terrible - thought I was going to die from pain”. She had other girls explain she was just doing it wrong - read two books on how to make it all better. After developing those newfound skills and trying again? Was still very distracting - never a source of pleasure. The idea was completely intoxicating, the reality was very different.”

We’re not done until I orgasm: Feeling compelled to perform sex regardless of circumstances is a new burden - but feeling you must always complete the deed? That sends lots of straight-leaning trans woman over the edge. Get a guy excited and don’t finish the job? You’re a prick tease. Finishing a guy off when its not your imminent desire or natural leaning? Seen more than one trans-woman drop the “guy thing” short;y after such a demeaning, unromantic experience.

Women love differently. Alas, it’s certainly not without its own set of challenges but if female-love is your inner preference? Everything else feels awkward: doesn’t feel like real love! Men and women love uniquely: trans women are aware of all these subtleties better than most because of their unique life perspective. It includes everything I just described - and much more. Female-Female love is more complicated - that higher intensity is the only thing that can feel like true-love to a bona-fide lesbian. To others? Its way too extorting and exhausting.

The Final Analysis: Transgender Women and Female Partners
Whew - took the long way around the barn to answer this simple question, no? Sorry: it happens!
Transsexuals and Lesbians
So simply stated: Does your Madeline prefer/need/want a man? Based upon both what I just shared and what you described about her and your relationship? Seems very unlikely.

If she never “experimented” with men during her transition, she might be feeling a need for what she perceives as solutions to her female confidence or life life leanings - but it’s a hollow shell. A lesbian, is a lesbian. Straight, is straight, gay guys - are gay guys.

A couple of final thoughts and opinions as you two move forward...

First, I’m not a fan of any idea that includes an “open” relationship. Just my personal opinion. Seen people make it work - was intimate was more than one such married couple earlier in my evolution. Alas, commitment is sacred, fragile. People who make open-relationships successful are usually less 100% commitment-driven at the onset. Love between two people is always challenging. Add other people’s drama? Its often impossible. I wouldn’t even consider trying that option going forward. If Madeline has to try this out with a man to sort things out? Break up first - know that’s hard but don’t try having your cake and eating it too - usually results in deadly food poisoning. It also most clearly compares the value of a desire to the worth of true-love.

Second, some trans-lesbians find fulfillment
fantasizing about men - but that doesn’t mean its their new orientation reality. Lots of straight women get turned on by the thought of being with another woman: act on it? Change sexual orientation? Not typically. Had two dear trans friends open about this issue last year - each professed transgender lesbians. Both admitted to getting most aroused by watching transgender porn of men with tranny’s: imagining themselves as that girl. One of them discussed this sensation with her female partner: developed their own unique role play fun to scratch the itch.

If you encounter this fantasy from Madeline? Don’t be threatened by it or read more into it’s meaning. Men are often driven to turn healthy fantasies into less than ideal realities. Women tend to just enjoy them for what they are: a playful distraction and potential source of fun.

You guys need to find that just-right opportunity to speak openly about all of this. Your hidden fears, her hidden desires - whatever’s creating a less than ideal basis to develop the sort of life-lasting love and commitment we all crave: and deserve!

Wish you
both the very best in your love and life.