Transgender/Transsexual/Gay crossdresser


I am a 25 year old man living in Kolkatta, India. I am gay and in a relationship with another man for the past 7 years. Ever since the Indian Supreme Court struck down the order of a lower court which had decriminalized gay sex, me and my boyfriend have been living in constant fear of the authorities. One of my friends recently got arrested by the police and we are planning to change our residence soon to avoid the same fate.

My boyfriend has requested me to become a full time crossdresser when we move to our new residence. He is worried that our neighbors might give us away. I have been a crossdresser for most of my life. Ever since I was a young kid I have enjoyed wearing my mother's sarees. My mother was a single parent and raised me alone. She would love applying make up on me and treating me as a girl when I would dress up. She would even call me by the female version of my name, 'Anisha' when I wore her sarees. I continued this practice of wearing sarees at home and dressing in feminine clothing even when I moved in with my boyfriend 4 years ago. He would love it when I dressed up and since I always took the passive role in our relationship and when we have sex, I felt normal and comfortable in female clothing.

But to date I have never worn my sarees in public. I have been sort of a closet crossdresser. But last year after being persuaded by my boyfriend I had electrolysis treatment to remove unwanted body hair. Dressed as a woman I generally appear to be, (atleast my boyfriend says this) to be quite feminine with a slim body and rather large hips. I am still learning how to speak in a feminine voice though. But the question of living full time in female clothing still makes me a bit nervous. In the place where I live there is a significant difference between the way women and men dress. It's not as if I can wear jeans and a shirt and get away with it. Women of my age are generally expected to wear sarees.

So I want to ask you about how to present myself as a woman in public so that no one is suspicious about my gender. I still break into a nervous sweat when I think about walking in a saree in public. Also please give me some tips on how to walk in a saree if you can or the closest equivalent of a saree in the west, which would be a long gown, I think. I want to appear as natural as possible. Add any other suggestions you think would be helpful in my situation.

Also living abroad to escape the discrimination against gays is not an option as my boyfriend has his business here and all my friends and my mother stay here as well. So I have to continue living here for the foreseeable future.

Anish / Anisha,

Sorry I haven't gotten back to you sooner. You contacted me the day before the Christmas holiday here and I haven't had much time to get on my e-mails. I'm just catching up today.

This is an interesting predicament you are in. I can understand your need to crossdress and appear as a female in public for the sake of your relationship. However your desire to crossdress is another matter. Most men who transition or take on a female role do so as they feel they were born in the wrong body. Someone just doesn't wake up one day and decide they want to change gender. It's a life long struggle that starts at a young age. Based on the way you worded your question, I'm not sure if you fit that role. As you dressed at home when you were younger and I assume this was before you met your current boyfriend, you may have some trans-gender traits. Also it's important to acknowledge that not all "trans-gender" people are "trans-sexual". It is a common assumption that all crossdressers want to become women and they are gay. The exact opposite is closer to the truth. Most crossdressers are in fact hetero-sexual and have families, raise kids, etc and appear to have normal lives. Only every now and then they step out of that role and will dress in feminine clothing. Then there are some "men" who feel they should have been born as women and live their lives as women and are attracted to and want to marry men. There are "men" who consider themselves as trans-lesbian and prefer the company of biological females but will live as a woman. Then there are of course gay men who are not attracted to anything feminine at all and prefer the company of men and of course have no desire to cross-dress. What it comes down to is there is no hard or fast rule as what is the correct relationship between gender and sexual preference. Just because you were born into a body does not mean you accept that body or the perceived normal relationship you are expected to have. You should be able to live your life the way you choose and don't allow the public to dictate otherwise.

Now saying that it's not always that simple. Here in the United States we are seeing more and more acceptance and understanding regarding the difficulties transgender people have. In the past transgender people were just seen as another aspect of gay culture. That seems to be changing slowly as more and more people become aware of us. However there is still a long way to go and there is still a huge amount of arrogance and hate regarding gay and transgender people. In other countries, especially eastern cultures including India, gender roles are much more defined and crossing gender boundaries is much less accepted. Please understand my knowledge of Indian and Hindu culture is limited to what I've been able to read, absorb through television and the people I've met here in the U.S. I understand in India there are deities which are worshiped who are both male and female and those who worship them are somewhat accepted into Hindu culture. I don't know if you would fall into that group or if you are Hindu. I'm just putting that option out there as a possibility.

Now to answer some of your most direct questions and how to present yourself in public without anyone noticing. Here we refer to this as "passing" meaning you pass as a female even though you are not. I've been told many times that I pass very well when I'm dressed as a female even though when I look in the mirror I see the "man" more than the girl. That is a common problem as we all feel we can be more feminine. Even women will obsess over this thinking there is always a way to be prettier and more attractive. So what we do is normal female like behavior. The key to passing is confidence. If you are in public dressed as a woman and you want people to accept you as a woman you just have to be confident that you need to be there. What you may want to do is find sometime when you can go out and just watch people. You don't have to be dressed, just go out in guy mode and notice that most people are oblivious to what is really going on around them. They are just to busy with their day to day things to notice the little details. Unless you are trying to draw attention to yourself it's very likely others will just ignore you. They will see the female attire and assume you are female unless they look very closely. Most will not. The more time you spend in female attire the more comfortable and confident you will become.

Your attire "at least at the beginning" needs to be simple and understated. I'm not saying you shouldn't try to be pretty but observe and study the women around you who are the same age and see how they dress. One of the things we often tell new cross-dressers is to dress "age-appropriate". Women will dress differently at different point in their lives. Young women tend to wear tighter fitting clothes to show off their body shape where older women who have had children tend to hide it more. The saree is a very diverse style and there are many options so you need to find what will work best for you and your body shape. You may be able to add accessories such as scarves, necklaces, and jewelry etc. The purpose of jewelry is to draw attention to certain places on the body. For example rings will draw attention to the hands, bracelets to the wrist, ear rings to the face and neck. How you accessories will be a mater of personal taste and style. In time you will find what works best for you.

Then there is make up. For a crossdresser, make up is going to be a must. How you wear it and the amount will be dictated by your features. But the general rule is, less is more. There are many excellent tutorials on line for crossdressers learning to apply make up.  

I've known many cross-dressers who come out for the first time dressed like a 2 bit whore with supper short skirts, bigger than big breast, overdone makeup, and sky high heels thinking they are dressed like a woman. That is really a fantasy and there may be a time and place to dress like that but it's not in public. As a cross-dresser who needs to pass you need to make sure you don't call yourself out. It's not just the saree or the dress, but little things you can do. For example women tend to eat smaller portions then men. Women tend to touch themselves and others more than men. Buy this I mean they touch their arms and shoulders and body when they talk. They also will touch others more than men will. As men we don't do this and it is really a difficult thing to learn to do and be comfortable with. Women walk differently than men. Due to the fact that a womans hips are wider they tend to have more of a sway or "wiggle" in their walk. Men can learn to do this by placing one foot directly in front of the other. Also wearing high heels will help as the increased height will cause the calf muscles to flex thus lift the buttocks a bit. Also don't go overboard with the boobs. Women come in all shapes and sizes. The breast size you choose should fit your body shape. If you are small and slender than an A or B cup bra should be fine. If you are larger a C cup may be necessary but I wouldn't go much bigger. I've known a few cross-dressers who can pull off a D cup or bigger but that takes some time and practice to get the confidence to put them out there.

What I would recommend you do is find any type of cross-dresser or alternative lifestyle support group you can find and get to know other cross-dressers. As I said there is a deity in India that is bi-gender and worshipers will cross-dress so that may be a good place to start. Get to know others and learn from their experiences. Over time you will gain confidence and one day you may find yourself becoming the teacher rather than the student.

The last thing I can say about cross-dressing is have fun with it. There is an old song from the 1980's by Cindy Lauper called "Girls Just Want to Have Fun". That is very true. Try different styles and outfits. Play with make up, lingerie, shoes, etc. Find what works for you. Just remember at the end of the day the clothes come off and go back in the closet and the make up washes down the sink and you are still you. You don't have to be anyone at the end of the day you don't want to be.

Again I'm sorry I took this long to get back to you.... If you have any more questions please feel free to send an E-mail to me direct at

I hope this helps.
Cheryl H.  


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Cheryl H


I can answer questions regarding male to female cross dressing and related issues. I will not answer any question dealing with pornography. If you are a minor and are asking adult related questions be prepared for me to either reject the question or tell you to ask an adult. Run on questions and that go on and on with various amounts of unrelated details will likely be rejected. I don't have the attention span to read 14 paragraphs crammed in to one about your high school crush before you get to the point. Fantasy and fetish inspired aka (Too good to be true) situations will likely be rejected. I wasn't born yesterday and I've encountered my share of TG fantasy. I can recognize the themes. Fictionmania exist for a reason. I'm a hetro cross dresser, this means I do not date men! I'm happily married with 2 sons. So don't bother asking me for a date... It's not going to happen and I will reject your question.


I am a life long cross dresser (male to female) and have been presenting in public for the past 10 years. I'm a member of Tri-Ess (Society for the Second Self). I've had the opportunity to get to know 100's of transgender people and have worked though and with those that are new to the transgender community. I have assisted many young and new "girls" when venturing out for the first time and worked with their families to help come to terms with many of the issues related to this life style. I am not a doctor or have any type of degree in this field, but I have cross-dreesed my entire life. Who better to ask a question about transgender issues than a transgender person. I am willing to answer any question I can concerning the Transgender lifestyle however there are some areas I will avoid.

Member of Tri-Ess, and Sigma Epsilon. (Society for the Second Self, Atlanta Chapter.)

No formal "education" but I have 40 years of experience being a cross dresser. Who better to speak with than someone who has been there, done that, and has the t-shirt. I'm willing to lend an open ear "and shoulder" when necessary to who ever has the need.

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