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How to Date a Pre-Op Transsexual Woman
-or- How to Date a Shemale or TS.

By- MichaelTSG

Are you seeking to date a pre-op transsexual woman, "shemale" or TS? Great!

Not all girls are born female. There is a special class of woman out there, with a different set of attributes than the "genetic girl," or GG. It's the transsexual woman, or "TS." A woman who used to be a male. "Pre-Op" refers to the fact that she has not had sexual reassignment surgery (SRS), the sex-change surgery.

Definitions: A "pre-op transsexual" is a woman in the wrong body, one who has breasts (through taking female hormones and/or breast implants), and a cock. A TS is almost always living full time as a woman. A "non-op transsexual" means that the TS will not have SRS. Usually that is also the case with a pre-op TS. I will be referring to both categories of TS as pre-op in this article, since it is a more widely used expression.

These are the topics that will be addressed in this article:

1. Why would a guy want to date a pre-op TS?
2. Sexual confusion and disorientation.
3. What does a TS look for in a guy?
4. How should a guy approach and treat a TS?
5. How does a TS regard herself?
6. The TS and the gay male community.
7. Sex with a TS.
8. Shemale escorts.

Let's address them one by one.

1. Why would a guy want to date a pre-op transsexual?

A lot of guys who show interest in TS's are, in fact, bisexual. Others are bi-curious. Still others are looking for cheap thrills. Some men find TS's to be more feminine than GG's. And then, of course, there are guys who seem to just plain connect better with a pre-op transsexual than a GG.

For the guys just seeking a sexual experience, there are plenty of shemale escorts available who will happily provide an exciting experience for a fee, without any danger of commitment. Don't know any escorts? Use a search engine, search under keywords "shemale escorts (enter name of your city or state)" -- odds are you will find what you need.

TS's tell me that most of the guys who contact them are, in fact, bisexual or bi-curious. They say these men are often looking for a same-sex experience but packaged in such a way that they have deniability. They seek to deny (to themselves, probably) that sex with a person who has both tits and a dick is homosexual in nature, when the guy is sucking that dick or getting fucked by it.

Some men find today's so-called independent woman to be not very feminine at all, overly assertive, argumentative, prone to characterizing a simple male advance as "harassment," and a general pain in the ass to be around. One guy told me dating a so-called independent woman "is like dating your brother." Who among the women of today delight in being extremely (and classically) feminine? The TS's.

Others find solace with a pre-op transsexual because she used to be a male and has a far better understanding of what it means to be male than most GG's ever will. Any guy who is chronically misunderstood by GG's will be able to appreciate the viewpoint of the TS.

2. Sexual confusion and disorientation.

Guys ask me for advice. "I met this transsexual woman at a club and I am really attracted to her but I am concerned that it means I am gay or something. Am I?"

Some careful dialogue with the guy usually uncovers the fact that he was very attracted to the TS's femininity. Her look, her voice, her movement, her laugh, her smile, her scent, and all those other feminine cues that trigger interest and a masculine response from a guy. Gay guys are not attracted to those attributes.

Therefore, if a straight man finds himself interested in a pre-op transsexual and is experiencing Missy Ann in Red some confusion as a result, then he needs to consider exactly what it is about her that is attracting him. If it's her femininity, then he's not responding like a gay man would, and thus shouldn't worry about whether he's "turning gay." If the guy can accept that he is attracted to a somewhat different kind of woman and still wants to pursue it, take it just one step at a time.

Take her out to dinner or a movie. Talk to her about whatever, listen to her words. Look into her eyes. Can he get lost in her eyes, as he can with a GG? Can he relax around her and just enjoy being with her, as if she were a GG? If so, take one more step. Hold hands, kiss her good-night. In other words, treat her like he would any GG date, at a pace that he can handle, given his concerns. Easy!

3. What does a transsexual woman look for in a guy?

What does any woman look for in a guy? A straight man, a guy who loves and appreciates women.

This quote came to me this evening as I was writing this article. A pretty TS said she wants "a man with class, respect, morals, intelligence, humor and loyalty." She is having great difficulty finding a man like that.

Why? Because most guys, she said, "are the same, they are just bi-curious or want their fantasy to come true." That is why god made "escorts." :-)

What a pre-op transsexual woman wants in a guy is what most any woman wants in a guy. Surprise, surprise! If a guy wants to develop a relationship with a TS (think this through carefully)…how should he approach her?

A TS who hangs out online gets a million instant messages and emails about sexual encounters. A TS who has the genuine sensibilities of the female will not respond to sexual adventure proposals any better than most GG's will.

4. How should a guy approach and treat a TS?

A male-to-female transsexual is generally defined as a woman in a man's body. The key thing to bear in mind here is: WOMAN in a man's body. If a guy wants to get past her suspicions about the nature of his interest in her, don't offer her a dick. Offer her flowers and a dinner date. He needs to express his interest the same way he would with any GG.

What genetic females will appreciate, so will the TS. Don't treat her like a freak. Chances are excellent she will resent being treated as a curiosity. She has endured a lot of pain and derision over gender issues, and has spent a lot of money trying to correct a mistake by nature. Be understanding and appreciative of her ordeal. Be a gentleman. Get past the plumbing issues and think in terms of her femininity. It's not that hard to do and she will greatly appreciate it.

Reading the articles at this website will satisfy your curiosity about what a TS is, what she needs and how she thinks. Therefore, a man doesn't need to bring up TS issues on the first date. Instead, he should focus on her, her life and her interests. He shouldn't treat her any differently than he would any other woman. She craves to be treated like any other woman, but she fully expects her date to ask inappropriate sex- and TS-related questions, because it happens all the time. Surprise and delight her! Don't even bring the subject up. Let her be the one to bring it up, if she wants. Doing things this way will likely make a very big impression. And that could put the guy miles ahead of everyone else vying for her attention.

Odds are, she's taking female hormones. That often results in feminine mood swings. Expect that. The pre-op TS may still have a dick, but psychologically she's a girl.

5. How does a pre-op transsexual woman regard herself?

She responds as a woman, therefore she regards herself as a woman. But being female for her is likely a whole lot more difficult than it is for the GG. Why? Imagine how men she meets react when she tells them she is a TS who hasn't had the sex change. Usually the guy immediately loses interest. He might even react with disgust. Or worse. This will impact on her sense of self-worth and esteem.

The pre-op TS will often adopt an image that is clearly, unmistakably feminine as she seeks to define herself as a woman. Probably she will not care to dress in a way that could be construed as masculine. A male appearance is in her past. The TS wants to immerse herself into something warmly and clearly feminine, which accounts for the clearly feminine clothing and heels. The TS is unlikely to identify with female Marines, Abrams tank drivers and fighter jet pilots.

Who is attracted to her? Mostly bi guys and thrill seekers. Finding a man who will accept her as a woman with a dick is very difficult indeed. But the man who can appreciate her femaleness, accept and love her is in for a huge benefit. He will be on the receiving end of a whole lot of attention, affection, and desire to please. His girl will probably go all out to look very desirable. She will wear very feminine clothing and shoes. She will work hard to perfect her makeup. After all, she loves being a girl. And she (finally) has a man who appreciates her. She is very unlikely to take him for granted. Interestingly enough, this approach to pleasing a man and adopting a feminine appearance is rather sadly lacking today among genetic women.

When my girlfriend and I go off to the movies or a restaurant, she is almost always the only female in the place in a blouse and skirt, or a dress -- and both the men and women notice her. You can see the envy in the men's eyes. They want their women to dress in a more feminine manner too, and it isn't happening for them. The TS's often have a better understanding of what men want, a better grip on how to be female.

6. The TS and the gay male community.

Often they are at odds. Gay men respond to masculinity, not femininity. A TS is very likely looking for a straight man, for it is a man who will make her feel like the woman she is, which is something to which most any GG can attest. Gay men will generally not find a TS of interest. There is often friction between the transgendered and gay communities. Some gay men accuse transgendered women as being unable to decide what they want. Although transgendered and gay communities ally themselves for political purposes, they otherwise have little in common.

7. Sex with a pre-op TS.

For those men who find themselves attracted to a pre-op TS but wary of the prospect of sex, here's a solution. Assuming that guy has read the earlier remarks in Section 2, then the solution is to think of having sex with a TS as just a plumbing issue. Forget about her penis. The guy has a girlfriend with a simple plumbing issue. There's no pussy, so get over it. What are the options? I'm sure any guy thinking of sex with a pre-op transsexual woman has quickly inventoried all the places he can stick his cock.

A TS on hormones may not have a functional penis. And a TS with the sensibilities of a SeaShore genetic woman is very unlikely to want to fuck a guy in the ass or stuff it down his throat anyway, so a straight guy need not be concerned about it.

Time for the orifice inventory. Will a TS want to suck cock? Get fucked in the ass? It's very likely she will. Can she cum? Many do cum from anal sex. TS's on hormones tend to cum repeatedly, much as GG's can, but without the usual male-type ejaculation.

Anal sex need not be messy. An experienced TS will know how to make it a great experience. Lubrication is a necessity. Keep some handy.

What is the essence of femininity? Females are nurturers and pleasers by nature. They are warm, loving beings who love to please. Sex tends to be tied up with romantic love. Women love to be "taken" by a masculine man, since it is the act of erotic surrender that centers them, that makes them feel like "a real woman." Therefore, hardly any TS with the sensibilities of a woman will be looking to "top" a guy or will be looking for a guy who wants to suck her dick.

Foreplay? Remember, treat her like a woman. She is going to respond the same way.

8. Shemale escorts.

The term "shemale" came out of the porn business, and it refers to a person with breasts and a dick.

I keep using the expression, "a TS with the sensibilities of a GG..." for a reason, to distinguish the TS who wants to be treated as a woman, who fully identifies with being a Missy Shoeswoman, from those who cater to the submissive male crowd, the bi-male crowd and the thrill-seeking crowd for money.

The genuine TS -- one with the sensibilities of a GG -- won't likely be promoting herself as a shemale any more than a GG seeking a real relationship will be promoting herself as an "escort." That means, one who advertises herself as a shemale or shemale escort likely has a viewpoint not very compatible with developing a sound relationship. Act accordingly.

A man needs to clarify his interests and goals. If he's just looking for a blowjob from a TS, or wants to suck some TS dick, cool. Pay an escort for some fun. If he wants to get something real going, then forget about the escorts. Why forget about them? Those girls get lied to every hour of every day and have heard it all. They aren't likely to believe that the average Joe asking for a simple date is serious. For most, the gateway to getting to know them is to first become a client.

That's it. Good luck. Feedback is appreciated.


"Great article. I am actually going on a date with a very classy TS next week. I hope to take her to a very nice dinner and just enjoy her company. If there is no sex then I don't mind because I will have got to know a very cool lady. I will remember what you wrote so I will not act like a fool and ask her about sex all the time and respect her as a true woman. Thanks and I will tell you how the date went." -from a man.

"Thanks for this. Made me feel good." -from a TS woman.

"I love that article. Very impressive." -from a TS woman.

"Excellent! That will save me hours of explaining things to these freaks. The points you make are well put. Most people are so clueless when it comes to a transsexual." -from a TS woman.

"That was one of the most awesome articles I have read. I myself have limited experience in this matter, I have only dated one, and it didn't last very long. She called it off due to what she said was her not being ready to commit. We are still friends and I call her every now and then. So I am a 43-year-old male still in search of the right 'girl.' The points you made in the article are great. I think it will open many eyes. Thank you, well done." -from a man.

"Your article hits all the issues dead on. Dating for us is such a minefield, strewn with so many issues, to tell, not to tell. Is he married, is he a gentleman, is he a jerk? The only issue you don't touch is violence, with is done to us a lot. At least it was to me.

"I'm a little older than most of the TS's you probably send it to and I really don't look my age. So another issue for me has been age, so many young kids looking for thrills. I personally have given up ever meeting online or in the GLBT bars around town. And with my own surgery this week, hopefully I can meet someone just living my life.

"I do think you're right, we tend to be a better partner and understand the men's issues better. We also tend to be as feminine as we can be, a result of going through this process. Thank you." -from a TS woman.

"Indeed very interesting...you hit it all on the head." -from a TS woman.

"I don't really know you but I read what you wrote about TS's, GG's and men and I think it was very well written and had a lot of validity to it." -from a TS woman.

"Great info, it answered a lot of my questions. OK now I just have to find someone in the central Florida area." -from a man.

"Hi, that's very good. Thank you for putting most of my thoughts into print. I think you should clean up the choice of words a tad, but I think it's wonderful. In fact, I sent a copy to a guy who was rude with me a few minutes ago. I loved it. Again, thanks." -from a TS woman.

"I loved your article. You handled a difficult subject with candor and sensitivity. Your girlfriend is a lucky woman!" -from a crossdresser.

"I just wanted to say I enjoyed your articles and to say thank you." -from a TS woman.

Ver. 1.2
Original creation date: January 8, 2003
Latest version date: February 24, 2003.

Mail to: Tsgirlfriend4me@aol.com

I reserve all publication rights on this article, but feel free to forward it to anyone you like. Copyright 2003, all publication rights reserved.


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The topic of this page is how to date a pre-op transsexual woman, how to date a shemale, and how to date a TS.