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Questions not to ask your TG Date

Amanda Valentine Dela Cruz
This post was last updated on .

We were all once novices in the world of transgender dating. Today, I’ve enlisted some questions in random order that you should avoid asking on the first conversation if you want to proceed to the next level.

Everyone’s individuality varies in enormous degrees but just know that the tips here are applicable in general as to not potentially hurt someone you really fancy.

You better not take risks, John!

Are you a virgin?

Stop right there! My or anyone’s virginity is none of your business. Nobody’s asking you how many holes your wiener has entered. I don’t know if this is common amongst western men but this is a very common question from men in my country.  This is so outdated and inappropriate. Polish your communication skills and think of something better.

Are you a top or a bottom?

How much are you going to pay me?!

Get the hell out of here with that Grindr-esque question.  My Transgender Date is a transgender dating website for transwomen and it’s not an app for one-night stands.  You will eventually get there when you finally meet your transgender date or have known her for a period of time. Never ever ask this on the get-go if you don’t want to potentially be blocked.

How big is yours?

The audacity is too much!

First of all, not every transgender woman is comfortable with her genitalia. Gender dysphoria levels differentiate. I personally have no problem with what I have between my legs but I have a lot of friends who don’t find their tails appealing.  I have a friend who can’t even look at hers and cleaning it feels like a battle for her.  Please be sensitive about this issue. Even if you think it’s trivial or irrelevant because you’ve seen a lot of transgender women playing with their girltoys in adult films, this is REALITY.  It’s fun to live in fantasy from time to time but you have to know that transgenderism is a constant battle to a big chunk of us trans women.

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Do you have a vagina?

Now this question comes a lot from men who have never tried making love with a transgender woman. I cheekily tell them how I don’t have a vagina and how I want to see them bend over for me and take my shenis like a man but in all honesty, it’s just as offensive as being asked about how big my girltoy is. Literally speaking though, I have about 8 adopted pussies and I’m actually looking for someone to take care of some of them because they can be a handful most of the time.

Just… avoid asking this Juanito.

Have you ever made love with a girl?

I charge $50 on the first minute and $20 on the following minutes.

No, Brad, I’ve never slept with a girl. Get the hell away from me.  Not only are you using me as a fantasy fulfiller to your current “no shower just ate pizza and drank beer plus it’s Sunday today and I wanna kill time by doing a jerk-fest on my couch” disposition, but you’re also playing with my sexual orientation.  My past sensual relationships have nothing to do with me signing up on this wonderful transgender dating website.

What I’m looking for is a man who makes 6 figures (not in Indonesian Rupiah) a month, 6ft 4, and exactly looks like Robert De Niro in Godfather 2. Just kidding (maybe or maybe not).

Well genius, transwomen here are looking for LOVE.

Now let me ask you something…

Why are you here?



Posted in Love and Relationships
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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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