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Dating A Man Who’s a First-timer with Transwomen

Are you a single trans woman trailing the journey to love? In that journey, do you often stumble upon first-timers who are novel to dating trans women? If so, this guide is tailor-made for you.

Why It’s Exciting

Everything’s exciting when it’s new. Queue up “Like a Virgin” by Madonna. However, how do you deal in a situation whereby you’re the one who’s going to show the ropes?

Simple, you have to take charge and see the situation as a silver lining. Others may call dating a first-timer a project. But you must see it as an opportunity instead.


If it’s their first time dating a transgender woman, the novelty will drive them to do almost everything. Excitement is similar to raging hormones and this feeling is quite contagious. While they’re excited about getting to know what it is in dating a trans woman, you’re also going to be excited about unfolding their real self.

smiling man

Although they have more to discover, it’s not going to be a boring ride for you. Added to that, you’re not only facilitating a new lifestyle to them. You will be more nurturing, understanding, and forgiving in the process.

Molding Them Into Your “Perfect” Partner

Just imagine the possibilities of turning someone into a perfect partner. Yes, it’s possible when you’re dating a first-timer. Because this person is treading carefully, they will be more cautious with their action. This caution will give you the power to turn them into an inclusive and accepting human-being.

happy couple

This is especially true if you’re planning to date a cisgender man who only dated cisgender women. Because these guys haven’t experienced the same level of discrimination and ostracization, they will truly learn a thing or two from you.

You’re Special To Them

Lastly, what’s going to make dating a first-timer gratifying is everything that you do will be special to them. Not only will your actions be very memorable, but you, just being yourself, will cement an irremovable dent into their memories. This is why it’s very important to make the experience positive for them.

couple holding hands

Because you’re their only example of what it’s like to have a trans-girlfriend, you have the upper hand. This is especially very good for trans women who don’t like being compared.

Why It’s Concerning

However, you must be open to the fact that not everything is rainbows and butterflies. There will be challenges in dating a first-timer. Buckle up because it’s going to be a rocky road.

They Might Change Their Mind

There are many reasons why a person will change their mind into being in a serious relationship with transgender women. These are as follows:

  • The sex may not be what they’re into.
  • They still prefer cisgender women after their “trial period” expires.
  • He’s a cisgender man who wants to live a “normal” life.
  • He’s a cisgender man who wants to have biological children with his future wife.
  • The arising challenges of how they’re going to explain the relationship to their family and friends may put them off.
  • They don’t feel “sparks” like it’s the fourth of July.
  • Or they simply may just not be that into you.

Don’t feel too bad the moment they change their minds. As long as you know that you are willing to give your whole self to the relationships, you should have ZERO regrets. This may feel redundant but the whole “It’s not you, it’s me” is simply true. It may not be precise but at the end of the day, it’s the truth.

He May Be Uncertain Of What He Wants

If you’re dating someone young or someone who’s in the LGBTQIA++ spectrum, this kind of situation may happen to you. Some gay men don’t want to admit to themselves that they’re gay and they ease in by dating transgender women. Others are simply too young and still finding out what they want.

thinking guy

This does not mean that you’re a bad girlfriend. It’s just that sadly, you’ve fallen for someone unsure of themselves. This doesn’t only apply to them, discovering their sexual orientation. Sometimes, they just don’t know what they’re attracted to and discover what they truly want later in life.

Others are so uncertain that they live double lives. Most of them are men who get married to cisgender women and cheat with people from the spectrum on the side. These guys are what people commonly call “being in the down-low”.

You May Be A Test Subject To Them

While dating someone confused is bad, it’s worse to be dating somebody who’s experimenting with you. The reason why experiments of dating trans women exist is because of porn. A lot of people get so deep with watching porn and their sexual desires that they start using other people.

Being objectified is one thing, but being used is another. You see, if a person pretends to be in love with you just so that you could fulfill their carnal desires, that’s where the problem arises. Before giving in to a first-timer, you must establish that you’re not a toy by doing the following.

  1. Be very clear that you are not EASY to get.
  2. You’re the prize and they should see you as such.
  3. Never chase them. Let them chase you.
  4. Have self-worth. Draw boundaries and be very clear with how you want the relationship to be.
  5. Don’t initiate conversations with them on the get-go. Let them do the required work and pass your “screening” method.
  6. Never make them feel that you’re desperate for their attention.
  7. Always let them know that they are not doing you a favor by showing their interest in you.
  8. You are a woman and men would be very lucky to be with you. Don’t give them the impression that you see yourself as something less.

Lastly, if you want to have lower chances of meeting a-holes, you must create a My Transsexual Date account. Doing so will give you access to decent men from around the world who are looking for the trans woman love of their life. Today is the perfect time to find love!

Posted in Love and Relationship, Uncategorized

About the author

Amanda Valentine Dela Cruz
Just a random trans woman playing with makeup and skincare. Loves bacon and the operating table. I'm also the author of the dating guide book Dating Transgender Women for Gentlemen. Know more ->

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One thought on “Dating A Man Who’s a First-timer with Transwomen

  1. Hallo Amanda,
    Ich bin nicht ganz einverstanden mit deinen Artikel.
    Du hast Recht, für einen”Anfänger” ist es eine große Aufregung das erste Mal eine Transgender Frau zu treffen.
    Nur in deiner Aufzählung an möglichen Männertypen ist fehlt ein Typ. Der Mann, der weiß was er will, offen ist und am Anfang steht, dieser Typ Mann wird etwas älter sein, möglicherweise Kinder haben und eine Cis Vergangenheit.
    Was denkst Du zu meiner Meinung?
    Lieben Gruß Torsten

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