Dear Gabi, I’m a Young Crossdresser Confused About My Sexual Orientation

Dear Gabi,

I’ve just recently discovered your website and wish I would have earlier in my exploration of crossdressing. ;) I’m 18 now and have accepted who I am, been dressing up since I was young, 5 or 6. I’ve come to terms with a lot of stuff, and I’m no longer ashamed of who I am. I have a loving girlfriend for almost a year now who knows everything as well, she is very accepting and supportive =)

My problem deals with my sexual orientation, I know I’m attracted to girls, thus my girlfriend, but while dressed, I find I’m always craving guys, so for a while I just thought I was bisexual, until when I was 16 had my first relationship and sexual experience with a guy. Now he was a full time crossdresser, even during high school, I think that was the main attraction. I was so turned on being with him, and kissing him. Anything to do with touching or seeing his genitals didn’t turn me off, but didn’t turn me on. I love the feeling of anal sex (from a male), turns me on immensely.

So basically I’m kind of confused, I look at a normal guy and I’m not turned on, but I always find myself thinking about having sex with a male and strap-ons with my girlfriend just doesn’t feel the same. I know it’s a vague question as well, I’m still young and exploring and advice would be amazing :)



Gabrielle HermosaDear Angel,

Being a teenager is tough, period. When social taboos and sexual orientation uncertainty comes into play, it can make life that much more confusing and stressful.

Social “norms” vs. reality
In terms of your sexual orientation, your confusion is probably the result of feeling out of sync with the “social norms” that have been etched into your brain since birth. Your feelings are in conflict with that which you have been taught is “normal” and/or “acceptable” within society, hence the uncertainty.

Sexual preferences
You’ve expressed being attracted to both men and women. The definition of “bisexuality” (taken from Wikipedia) is sexual behavior or an orientation involving physical or romantic attraction to both males and females.

In terms of being attracted to woman as a man (not crossdressed) and being attracted to and/or fantasizing about men when you’re dressed as a female (crossdressed) – I’ve read many accounts of this kind of sexual preference expressed by other crossdressers. Categorically, it still falls under bisexuality. Exactly “how it works”, applicable terminology and semantics are often discussed to great length in transgender communities and message forums. There is a rather complex array of attraction preferences that may be explored and debated. My assessment and opinion is based on the context expressed in your letter.

It certainly sounds to me like you’re bisexual. Maybe pause for a moment and ponder that reality for a bit. There are literally millions of bisexual people, a percentage of which are crossdressers, too. You’re not alone in how you feel about men and women, sexually. People like what they like. Being bisexual is nothing to worry about or stress over. It’s just a very common (even if not always popular) personal trait, shared by many people.

Regardless of how or when you prefer romance with a female or male companion, perhaps what is most important is simply being with someone you love, enjoy, and are compatible with, who feels the same about you. It sounds like your current girlfriend is a pretty awesome gal, based on the little you’ve written. I hope you appreciate her and let her know how much she means to you.

Sexual curiosity, fantasy and monogamy
Whether you are involved romantically with a man or a woman, many partners tend to prefer a monogamous relationship. If your girlfriend (or future lover, be it girl or boy) is expecting an exclusive/faithful relationship, then it really doesn’t matter if you prefer women sometimes, and men other times, because you’re already taken. Even for straight couples, the question of “I’m with this person, but I really like that person, too. What should I do…” often pops up. It doesn’t matter if you’re attracted to another woman or a man. Cheating is just that – cheating. Unless you’re in an open relationship (as in you both agree that seeing other people is acceptable), feel free to look around and fantasize, but you’d best remain physically and emotionally loyal to your girlfriend (or current partner).

It sounds like you’re pretty happy with your girlfriend, even though you have a craving for men at times. Straight, gay, or bi, very few people ever have the opportunity to experience every sexual fantasy they desire. I’ve fantasized about many, many women over the years – far too many to count or even remember. Being married, I still look at and admire other women (and always will), but my wife and I enjoy a monogamous marriage. Point is, everyone fantasizes. You just happen to fantasize about women and men, but again, that is just how it works with bisexual people, trans or not.

Fear of the unknown
If you find yourself wondering “Where is this all leading?”, be it your sexual preference, gender identity, or anything related – try not to worry about it. Perhaps easier said than done, but it’s good advice, nonetheless. Remove sexuality and gender from the equation, and understand that most people still wonder where things are going in their lives. There are a zillion things we all sometimes feel very uncertain about. That’s not unique to trans folk, bisexuals, or any other segment of the population. It is common for people to make a bigger deal out of things when gender identity and sexual preference come into play, but that’s mainly due to those things being (generally considered) outside social “norms”.

Plan for the future, but live in today
Here you are today – not necessarily a physical location, but rather simply your place in life as it stands at this point in time. Did you have a good day? Was there something (hopefully many things) that made you smile? Did you make anyone else smile? Who knows what the future holds for any of us: trans, straight, gay, bi, or anything else. Life is a journey – one that is very unique for each of us. Try to enjoy each little pit stop along your journey and don’t stress over where your path leads. Enjoy the happy moments that each day holds. We all have bad days and hard times, but try to concentrate on the good times. Don’t loose any sleep over social “norms” or exactly what category [whatever] happens fall in to. Just be yourself and be a good person. You may experience changes in how you feel about or view things over time. That’s a part of the growth and evolution process we all experience, regardless of orientation or gender.

Teen life is a strange, strange place to be, so try not to let thoughts of being “outside the norm” get the best of you. In a few more years, you’ll realize that you are, in fact, very normal… or that no one is truly normal… or probably both.

Good luck!
Relax and make the best of things as they are. There’s nothing wrong with you. Seriously! Not based on anything you’ve written. Take things one day at a time and enjoy being young.

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13 thoughts on “Dear Gabi, I’m a Young Crossdresser Confused About My Sexual Orientation”

  1. When I see something like this a thought always enters my mind.

    That is the effect of social pressures, or norms upon your own thinking.

    What I mean is, why is the fact you are wearing clothing that women wear does the sex your are attracted to change?

    Could this just be a part of you? Or are social norms swaying you. The social norm is that which says “women are attracted to men” “If a man appears as a woman, then he must want to attract men” I know in my personal case this is FAR from the case. When I first went to Rocky Horror wearing a spandex minidress, hose, makeup, heels, and wig, I was MORE attracted to women. This is completely against the societal norms. But it is my case.

    The fact you like women when in male mode, but attracted to and fantasizing about men when in girl mode, makes me think you are at least partially being influenced by societal norms.

    Is this bad? Personally I have always thought there was something not healthy about group think. Group think is what leads to mob mentality. I know there are times it is unavoidable, and at times even beneficial, but most of the time it is restrictive on individual thought.

    What I suggest is that you test yourself. See if in male mode you find men in the least bit attractive. And really think about that, even the genitalia (sorry if that is graphic, but you need to think of all aspects of the physique of the sex you are attracted to). I know for me I am not attracted to the male physique.

    I hope this meandering post helps you. And Gabibrielle I look forward to your response :)

    1. Thanks for offering your perspective, Pythos. I’m sure Angel appreciates it. :)

      I understand your points. There are the social norms and expectations swaying how people think – both from an outside point of view to how we look at and feel about ourselves (as we’re all products of our society). The “herd mentality” often works in negative ways. People are uncertain of [whatever], talk to others who may be uncertain and/or dislike [whatever], then the they convince others in the group that [whatever] is a terrible thing as they build off of each other’s mounting negative feeling about [whatever], etc. Finally, the last point about re-assessing which sex is attractive and when.

      Whatever is at the heart how and why Angel is attracted to which sex and why, all I can say is that it is something I’ve read many times before. However it works, in terms of the complexities and underlying motivations, it simply is what it is. This is kind of a sloppy comparison, but it’s almost like asking someone who doesn’t like peanut butter to just try it again, but do so while thinking of it differently than before. Chances are, they still will not like peanut butter no matter how they think about it or what mood they’re in. I don’t think that (on the whole) bisexuals can manipulate, to any significant, how they feel about who they’re attracted to, regardless of gender or gender expression, nor do I think they should try to. If someone is in a very feminine state of being (ie: a bisexual male transgender/crossdresser) and in that feminine state of being finds themselves more attracted to the masculine side of things (a man), then that’s just how it works with them. If they’re in a more masculine state (ie: a bisexual male, trans or not) and find themselves attracted more to the feminine side of things (a woman), then that preference makes sense, too, in that context. If a bisexual is not trans at all, what motives them to be attracted to a man vs. a woman? It’s the kind of thing that I’m certain many psychologists and physiologists (and several other-ologists) study in great detail as part of the study of the human condition (as a whole). In the end, how we behave, feel, and view the world around us, in every conceivable sense, is just how our minds are wired – the neuron configuration, synapses, chemical balances, electrochemical reactions, etc. are all in different proportions for everyone. Those differences, compiled with different experiences everyone is subject to, equate to why people feel about things the we do, in terms of why it is different from one to the next. Two people eat the exact same meal prepared by the exact same chef – one loves it, the other is disgusted and cannot eat more than a bite or two. It’s all about the differences in chemistry (including outside influences). Again, it’s a sloppy analogy, but when it comes to sexual preferences, strait, gay, bi, or anything else people call it, that, too is going to vary from one to the next. It’s just that some of it falls outside the “social norms” of a given society, which is why it becomes confusing to people – both to those who are different than the “norm” and to those who make up the majority within the “norm” who cannot understand why others think/feel differently then they do.

      Ok… and I have no idea if I addressed the points you were looking forward to my response on. lol I kind of got caught up in a riff and just kept going. Hope it reads well for what it is, because out of time now. Oh well – I tried. :)

  2. I’ve experienced something like this too. I cross dress via online virtual worlds because I haven’t told my family about my cross dressing side yet. In games, I chat with normal girls, and they chat back (Don’t worry, I’ll get to the point soon). People treat me like a girl, including boys. Some flirt with me, I return some flirting back. When I’m not cross dressed, I;m not attracted to boys at all. But when I’m in female mode, I can be flirty, joking, and boy-crazy. It’s kind of weird, really, but it happens. If I’m not presenting myself as a girl, I’m attracted to girls, not guys. But, if I’m cross dressing, I flirt with the guys, and the girls are just people like me to chat with.

  3. OMG!!!!! This is EXACTLY what my SO is going through!!! … only he’s 42. I just learned about his desire to CD 6 months ago. I took the news just fine and thought “whatever gets you going…” but then he delivered the news that he’s NOT attracted to other men, but he IS highly turned on by looking at other CDs. Top that off with he’s not sure if he’s bi, gay or WHAT and he may want to try being with another CD but he’s not sure in what capacity. Oy Vey! He says he loves our sex and he loves me but then, fast forward 6 months and he’s texting some other CD “stuff” and sharing pics. This broke my heart. I don’t care if he CDs but I DO care if he’s turned on by another CD and WANTS to be with him/her. To me, it’s cheating and he has broken my heart. In the meantime, he’s depressed and sullen. Very withdrawn for days at a time…but then will be fine for a while. I asked him to get therapy (for depression) but he refused. I just don’t know what to do or how to help or..or…or…

    Thank you for posting this, Gabby. I couldn’t believe that someone was brave enough to express the same situation my SO is going through.

    I wish I knew how “long” his process will take…but the more important issue is I can’t tolerate the websites and flirting contact with other CDs…

    Any other words of advice??? Much appreciated!

    1. Hi Kim, thanks for sharing your situation. I’m so sorry to hear about the difficult position you find yourself in. I can certainly understand your “broken heart”. The news that a romantic love interest is flirting with someone else and has expressed the diesire to experiment sexually would be devastating news to most people, I’m sure, regardless of gender expression or sexual preference.

      The bottom line is that if two people are in a monogamous relationship and committed to each other to some mutually agreed extent, there should *not* be any outside flirting/communication with another potential sexual partner, period. The factors really don’t matter – there is being faithful and there is being not faithful. Whether or not the reason for being not faithful (or the expressed potential to be with another sexually) is an acceptable condition is really up to you.

      If your significant other is confused about his sexual preference, that is something he should probably be discussing with a therapist who is well trained in this area. This kind of confusion exists in many people, crossdressers and non, and heavily fueled by the notion that people are expected to fall neatly into this category or that. In reality, many more people have pondered the idea of same sex relationships than admit it. Most often, they sort out their feelings on their own and go with what they feel is right for them (either having experimented or just thought about it). For many people, it’s a difficult thing to work out and professional help should really be sought. The sooner these feelings can be sorted out and worked through, the sooner the individual may get through unnecessary bouts of confusion and depression caused by the uncertainty.

      Living in a world that punishes people for deviating from the social “norms” is a very difficult thing for most of us (trans folk) and often takes years to work through. I hope that your significant other will choose to work through his confusion with some professional guidance. If you can be there for him in some supportive capacity, even if only as a friend, I’m sure that would be a big help. At the same time, you deserve to be loved and treated by your partner (with full monogamous devotion, etc.) as you offer them. If the troubles with your current significant other are causing you great emotional distress, which is most understandable, you may need to get out of the relationship in order to deal with your own pain and move on with your life.

      I hope that the two of you can both work through the things that you need to work through and eventually find the love and happiness you both deserve, whether it be together, or aprart.

      On a side note, if this doesn’t work out, Kim, I certainly hope that you will not think poorly of all trans folk because of the pain caused to you by one. I’ve said it many times – trans folk are as varied and different as non-trans folk. There is the best and worst of any segment of the population out there, and one should not to try and sum up or pre-judge people based on the actions of *another* who happens to have one or two things in common with them on the surface.

      If you don’t mind – please give us an update at some point in the future, or message me personally, if you prefer (contact link is up too). I wish you both much luck as you work through difficult times.

  4. I long to dress as a woman everyday and do wear panties, bras and women’s shorts daily. I can’t get any positive feedback from my wife because she doesn’t really know I am trying to transgender with hormones naturally and really prefer to see myself as a woman. I fantasize about me in bed with a man and he treats me like a woman with my lingerie and all. I wish I knew how to get her to accept the real me like other wives I read about. Any ideas?

    1. Larry – if I understand correctly, you are fantasizing about being in bed with someone other than your wife, and you want your wife to accept that as the “real you” or a significant part there of? All transgender aspects aside, most married women tend to prefer monogamy and loyalty in a marriage. In “open” marriages, both partners generally have an understanding that they may have extra-marital relationships, and there are usually some kind of mutually agreed upon terms to that kind of openness. It doesn’t sound like your marriage falls into that category based on the little you’ve written. I think the transgender issue is the least of your concerns when it comes to your wife “accepting the real you”. Married women tend not to don’t take the news of their husband fantasizing about being with another partner very well.

      If you feel the need to be feminine, period, and would like your wife to accept *that* as the “real you”, you’ll need to share how you feel with your wife. You’ll also need to understand than not all women will be open and accepting of their husband being feminine, and that’s their prerogative. You cannot force your wife, or anyone for that matter, to be open to, and accepting of that which makes you feel best. Just like no one can force or talk you into being happy being anything other than how you feel you should be. People like what they like, and the same goes for dislikes. In terms of marriage, if there is a lack of mutual compatibility, whatever the major factors may be, there’s going to be trouble. Marriage counseling may offer a healthy, controlled environment in which both parties can express how they feel about things and decide which direction is best to move forward in life from that point, be it together, or apart.

  5. I just came across this site via a Google search, and it is *really* incredible. Angel’s question sums up in many ways the way that I feel about myself. Not precise, each individual is unique, et-cetera, but it’s close. I don’t feel quite “bi-sexual”, since I’m not really turned on by men, but I am REALLY turned on by the idea of playing a female role with another man. Let’s just say, I’m definitely NOT conventionally straight. Either way, Gabrielle, I admire your courage tremendously to put up a site like this, and I hope to read more on it. Be well.

    1. Hi knickerbocker, thanks for chiming in. :)  I think I understand how you feel.  I’ve heard similar accounts from other tgirls.  For some, the attraction is not to the *man*, but in being the “girl” with a man in a romantic sense, much like you describe.  Bisexuality is kind of a sloppy term in that sense.  The point of attraction seems more self-focused, even if engaged in activity with a man.

      Regardless of what the motivation is, it’s not something that one should be worried or concerned about.  The “how” things work is not as important as finding that which is the most meaningful in your life and has the chance of brining happiness to both you AND your partner.  The focus should be placed on mutual interest, respect, love, and potential for long-term partnership.  Unless of course, both parties are just looking for some temporary fun in the moment.  It all depends on what the goals are.  So long as no one is being mislead or harmed or cheated on, there is usually nothing wrong with what consenting adults willing choose to do with their time together.

  6. Wow, I can actually relate to the poster a lot. I was kind of in the same boat. Heck, I’m still in the same boat. But I don’t really worry about it too much, is all.

  7. omg thank you soo much angel for posting this on here because this is exactly how i feel, like when im dressed and am in girl mode all i can think about is being with a guy and having him treat me like a real women, but when im in guy mode i never think about guys at all and for a long time it was really confuseing me :( and im just so glad to see that there are other people out there going threw the same thoughts and feelings as me :)

    and i also thank you gabi for posting this sight up here because your sight here really inspires and also helps out alot to people who are confused and are woundering about Dressing and i was also confused for a while (ergo im oly 18) but now i do understand alot of things better :) and i am proud to be able to say that i am me and i am a Crossdresser

  8. when i desire to dress up in female mode, its like a switch in my brain that goes to female mode and she dresses me all up pretty from head to toe. i am a straight heterosexual, but when in female mode its like i am all female and want to have fun as a female in every way.when i have time to dress up pretty, i start with taking off male clothing and then its all over my feminine side kicks in and dresses me up,panties, pad, bra, nylons,slip, sexy dress, jewelry,make up, perfume, heels, wig, when she is all done getting pretty she feels free, stress free, but paranoid,i my self enjoy dressing up as a female. feeling the sexiness of the clothing and seeing how pretty my face is when wearing make up and jewelry.some times i don’t get enough of being dressed up and feeling feminine at times. just thought i would let other cross dressers know. thanks for your time to read this. hope it helps others out

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