TS Dating Gude

America's Foremost Transgender Woman


Problems for Women Dating a Transsexual Female

A transgender partner can make for an ideal match with some women. However, we can come with some added challenges, including:

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

The Biggest Challenge: going through transition with her

One of the biggest challenges for women in a union with a transsexual woman is the “moving target” issue.


If she’s not done with transition? She’s still evolving. And with evolution often comes surprises.

By far the most challenging aspect you could face in this relationship is actually going through transition with your transgender girlfriend. There’s a monumental difference between dressing up as a woman plus taking some hormones versus becoming successful in a new life “as a woman” 24 / 7.
I wouldn’t wish going through a gender transition with someone on my worst enemy: it’s often that brutal.

Women with Transsexuals

A gender transition is overwhelming, exhausting & filled with pain from comments & insults nobody enjoys. There’s also the arduous process of finding a career that will work for a trans woman and dealing with family drama.

The most fun project? You get stuck in the role as mother - with a teenage girl - during the common occasions she tries wearing completely inappropriate outfits. Those heated arguments are as bad as you’ve ever seen with a teen girl and they can carry over into your bedroom.

As trans women we often like to espouse we’re “the best of both worlds”. However, after a heated exchange with your young trans woman over a skirt that’s much too short? You’re likely to argue we’re actually “the worst of both worlds”.

Guess what else teen girls usually want to explore? Yep - sex! Its only natural she’ll have some curiosity about flexing her newfound feminine mystique in front of others. Those aren’t the only risks. Some transgender girls find the whole process so overwhelming - they end up with deep emotional scars that cause them to be less than ideal for sustaining a healthy & loving post-transition relationship.

Make no mistake: transition sucks!

Being Viewed as Lesbian

Another challenge for some women is the fact they’ll be perceived as lesbian with friends, family and children. A transsexual might still have some male anatomy but the world around you will see two women together. For some? That’s not a bridge they’re able or willing to cross.

Transgender Girl

You’re note remotely bisexual

One of the more interesting interviews I did in this regard was between a trans-woman and natural female where the latter was 100% straight - and it was the trans-woman that ended up pulling away for that reason.

When we were intimate, it was obvious she was turned off by my breasts and body. I could feel her seeking and needing anything about me that was male. It made me feel ugly. I gained a whole new appreciation for how a woman must feel if her husband is actually a closeted gay guy. They touch you differently.

Will she someday want to get rid of her penis?

TS Relationship Questions

Most transgender women plan to eventually have GRS - they never feel complete as a woman without it. However, there’s still lots of transgender women that plan to keep their penis. However, a large number of those end up getting complete gender reassignment surgery due to the realities of living as a transgender female. In the beginning, dressing as a girl & taking HRT is a life-fulfilling odyssey & great source of pleasure. However, after a trans-woman evolves to going full-time, she quickly discovers that not being legally female is a huge source of drama in work & daily activities.


For some natural born women? This final step is not something they’re comfortable with in a relationship.

Erections & other matters of the bedroom

Perhaps the biggest disappointment for many women who were drawn to a transsexual based upon pornography is the fact many trans-girls can no longer achieve or sustain an erection after months and years of hormone therapy.

The only solution to this “condition” is shots of testosterone and EDS supplements like Viagra and Ciallis. Most trans-women aren’t comfortable getting testosterone injections since side effects like body hair growth minimize years of hard work with estrogen.

Less stable financially

Between the direct costs associated with a gender transition plus the inherent subsequent discrimination in the workplace for transsexuals, trans-women are often upside down financially. Lots of trans-women not only lose their job after starting transition - they often lose their ability to ever earn much of a living.

New and proposed laws are improving this dilemma but changes are slow to occur. Rarely is a transsexual an ideal candidate to be the primary financial provider for a household.


We’re often damaged goods

Dealing with transgenderism throughout ones life often creates a lot of negative emotional outcomes. A brutal transition only aggravates these outcomes. Finding someone without an overdose of detachment issues, emotional outbursts, narcissism or related insecurities - is difficult.

Gender Role Conflicts

Sometimes, two ladies possess all the core fundamentals for a solid relationship but struggle sharing feminine accolades & roles in they're loving union.

For instance?

Who holds open the door? Who is most often in the traditionally female role when it comes to sex? If these needs are in conflict? The relationship is often doomed from the start. Ideally, each partner is naturally comfortable in certain roles and the couple learns to share the rest equally.