Dating a Shemale: Things to Know, Pros, and Cons in 2019

There are some men who really enjoy dating shemales. A shemale is a transgender woman who has not had gender reassignment surgery, so even though she’s a woman she still has her male genitalia.

Some transgender women choose to keep their male genitalia rather than go through the surgery, or they can’t do the surgery because of the cost or because of other limitations. And some transgender women choose to keep their male genitalia because they are more appealing to men that way.

Dating a shemale can be an adventure for men who have never done it before, but most men who have experienced it can’t say enough about it. No matter their concerns beforehand, they end up loving it. It becomes more than a taboo or fetish and simply becomes their dating preference.

If you are new to the idea, we have everything you need to know about it, including the pros and cons of dating a shemale.

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Things To Know about Shemale

Transgender women identify as women. In most cases, you’d never know that she was once a man until she tells you about her transition. However, transitioning from a man to a woman is very different than undergoing sex reassignment surgery. That’s usually the last step in the journey to fully become a woman.

By that point, though, even though she hasn’t undergone the surgery to remove her male genitalia, she identifies as a woman already and regardless of the surgery she is legally recognized as a woman. That’s why some transgender women decide against the surgery, as they are already acknowledged to be women in the eyes of the law.

On the other hand, some transgender women know that there are straight men who fantasize about being with shemales. They have fantasies about dominating a shemale in the bedroom and while those fantasies don’t always play out in real life, there is still something there that inspires men to pursue relationships with transgender women.

Whether you’re new to dating a transgender woman, or your are hoping to learn more about dating a shemale, we have a list of the pros and cons that can give you a better understanding of what it’s like and what you can expect when it comes to dating a shemale.


Pros of Dating a Shemale

Love Being Women

With a shemale, she chose to become a woman

Some cis women are uncomfortable in their own skin. Self-confidence is a big issue for them.

With a shemale, she 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. 

Lots Of Intimacy

Being comfortable with their bodies help shemales to be very passionate in the bedroom. They know what their men like and they know how to make it all happen. Like any other woman, they crave intimacy and when they find the ideal mate they love to bring the intimacy into the bedroom.

Shemales Know How To Please A Man

Shemales Know How To Please A Man

Transgender women know how to please their boyfriends because they understand the male anatomy and what feels good. The reality is that she might not have wanted any part of being a man before, but that doesn’t mean she doesn’t understand what men like. They know what turns a man on, and they know how to use that knowledge to bring the most pleasure to the men they love.

In some cases, shemales are very well versed in various sexual techniques that come from having the experience of being a man. What might be taboo with a straight woman is par for the course with a shemale, and many shemales are very open to experimentation.

Shemales often understand that most men they encounter either haven’t been with another man or with another shemale, so expect her to be very patient when it comes to showing him the way.

New Experience For Both

For many men, dating a shemale is an adventure. Eventually, what starts out as something that men experiment with becomes something that they crave. Similarly, it can be a whole new experience for newly transitioning shemales as well.

Many men harbor fantasies of being dominated in the bedroom. While they might not be open to having a sexual encounter with another man, having those experiences with a shemale is much different. And once they try it, lots of men find that they want it.

Some men enjoy being with shemales who are transitioning. She might not have breasts yet, or she might be starting out on this journey. It’s very new, and it’s something that can make a relationship feel very adventurous. It’s almost like she’s a young girl and he’s the man in her life. This can turn the heat up in any relationship, and he will always have a special place in her heart because he was there for her through the hardest part of her journey.


Cons of Dating a Shemale

Hormones Can Make Things Difficult

Hormones Can Make Things Difficult for shemales

Transgender females must take hormones to counteract the testosterone in their bodies to keep hair from growing on their faces and to help their bodies adapt to being a woman. The more hormones she takes, especially early on in the process, the moodier she can be. It’s outside of her control, of course, but it can put a strain on a relationship.

Think back to puberty and the hormones working overtime through your body. Now think of what it would be like to take hormones to counteract the hormones that have been in your body for years and years. These hormones are constantly working to change her body and it can take a toll, mentally and physically.

This can be especially challenging in the early stages of her transition. She might not have had her breast augmentation surgery, so she will resemble a man more than a woman physically. These will be difficult times for her, and she will need someone around her who can support her emotionally.

If you are dating a shemale, know that there will be moments that are tense, and the tension comes from those hormones. It’s not you, it’s not her, it’s the hormones. Talk to her and find out how you can support her through the peaks and valleys of her emotions.

She Could Have Past Trauma

we live in a world where life for transgender folks is usually very challenging

Unfortunately, we live in a world where life for transgender folks is usually very challenging. They are the subject of attacks and discrimination all the time, going all the way back to when they first started to transition. Not all transgender women get to have the Caitlyn Jenner experience.

You might find that your partner has been the victim of hate crimes in the past, or that she wasn’t able to afford some of the surgeries right away and so she had to live in flux for a while, which is also challenging from a mental standpoint as her mind reflects her being a woman while certain parts of her body are still male.

Sadly, past trauma can make current relationships difficult because she might still be working through her experience and that can impact where she is with you.

Dealing With Stigma

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?

The answer, of course, is not at all. You are not gay because you enjoy being with transgender women. At least, you don’t have to be. (And does it really matter – no!)

The reality is that just as there are men who enjoy the fact that being with a shemale means lots of anal sex, which is taboo for many cis women, there are also men who enjoy the idea of a shemale performing anal sex on them. Short of using a sex toy, that’s not an experience that can be achieved with a woman.

Despite the fact that this is about dating and pleasure, the stigma surrounding it can make it difficult to be open about your relationship if your transgender girlfriend is open about being transgender.


Final Thoughts

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 different, and they will cherish a man who treats her well and worships her for being the gift that she is.

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 shemale, make sure you let her know. Let her know that you’re willing to be open minded, and that you want to learn. Let her show you how amazing being with a shemale can be. When you have clear lines of communication, and an understanding of how your relationship works, dating a shemale can be the best experience of your life.


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