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Getting Comfortable with Shemales – What You Need to Know

If you are interested in dating a trans woman, or just having a fling with one., there are certain rules of engagement that you should consider. Sure, following a T-girl Snapchat account might be fun and it even might feel like you are dabbling in taboo, but that is a far cry from dating or having amazing sex with a trans woman.

This is precisely why we wanted to make sure that you know what to expect, how to act, and what is not permissible once a gorgeous trans lady decides to grant you her time and, quite possibly her love. So, let’ start explaining.

Don’t be in it just for the sex, or at least be open about it

Let’s start from the beginning, a lot of people, men specifically, tend to oversexualize transgender women as these rare, mystical beings who are always horny and ready to have sex. Sadly, many guys, consider trans ladies to be "good enough" for sex but not to be seen out with in public. If you are one of those, you should not be getting comfortable with a trans lady.

However, if you are direct and open about what you are looking for, there are a lot of T-girls who just like to have fun. Jut check out the transsexual Snapchat usernames, and you will see the ones willing to DM and even meet up. No false expectations, just good old-fashioned fun, and games.

However, if it is dating that you are looking for. There is a bit more learning that you need to do. 

Be sure about what you want and expect

This usually means that you need to be sure about your choices before making them. Are you comfortable being seen with a trans girl in public? That is something you need to ask yourself. This is what trans women had to say about this particular issue – “If you are only comfortable with me in the bedroom, then you are not comfortable with yourself. You should be able to be secure at the beach, coffee shop, and anywhere else. Trans women can sense when men are insecure about dating us because they don't show affection like they would behind closed doors. A friend of mine told me that a guy she was seeing would intentionally walk ahead of her and not show any form of PDA, and only wanted to do takeout from restaurants. She asked him why he kept doing this and he said he didn't want anyone to know they were together because she was not very "passable." This, my friends, is the definition of a true asshole.”

This is why being open and honest first with yourself than with your desired partner is an absolute must. It is just not fair to waste anyone’s time. 

It is not about “passability” 

If your criteria for dating a trans woman is just how much they look like a woman in your eyes or according to socially acceptable parameters, then you should not be considering it at all. First of all, a shemale chose to become a woman. In making the transition, she is finally where she wants to be, and she loves it. She embraces it. In fact, you’ll be surprised at how much she loves to be a woman.


Shemales love to flaunt their bodies. (There’s a reason that shemale porn is very popular because these ladies know how to work it!) When you have a shemale on your arm, people will notice the beautiful woman with you, and they’ll be talking. 

You should be ready to deal with the ‘stigma’ surrounding dating shemales. The fact of the matter is that one of the most common issues that men face when they date transgender women is the stigma that they’re “gay.” If a man is with a shemale, and she used to be a man, doesn’t that mean he’s gay? Of course not. You are not gay because you enjoy being with transgender women. At least, you don’t have to be. It all depends on your personal choices. 

And if you are dating a trans girl who is just transitioning, you need to be there for her as she is now and not wait for here to fully transform in order to be comfortable dating her. 

Finally, make having fun your main priority

Yes, it might not be exactly as what you see on TS Snapchat accounts, but your shemale lady is all yours and you get the pleasure of getting to know her, grow with her and enjoy her company. That is the major benefit of getting comfortable with a T-girl. 

Remember, dating a shemale is incredibly rewarding because she knows that you have chosen her. Most transgender women have experienced a lot of emotional trauma growing up differently, and they will cherish a man who treats her well and worships her for being the gift that she is. 

The best thing you can do is just not pay attention, you have this great girl by your side, you two are having fun and enjoying each other’s company, what more can a man ask for. It all comes down to someone’s character and what they can bring to the relationship. If you don’t focus on transness but rather on how great your date is, you will be pleasantly surprised with everything that comes next. 

Always remember that the key to any relationship is open communication, so if you are uncomfortable or uncertain in any way about being with a trans lady, make sure you let her know. But also make sure that you inform her that you’re willing to be open-minded and that you want to learn and grow as a person. That kind of attitude can really go a long way.