I am a 21 year old person. When I was 10 years old my genitals were amputated due to an auto accident which killed my parents. My urethra was diverted to a small opening just below where my scrotum used to be so that I have to squat to urinate. As a result of the amputation I didn't go through male puberty and now only take low doses of testosterone to keep myself from becoming frigid but not enough to change my external appearance which is quite feminine.
I identified myself as a male after the accident for many years and went through high school and college as a male. It was difficult sometimes to live as a boy since I didn't develop a deep voice or an Adam's apple and have naturally rounded buttocks. All of this contributed to people frequently mistaking me for a girl. Sometimes it was fun to lead them on and pretend that I was a girl and they would only realize their folly when they noticed the complete absence of breasts.
Now I am 21 years old and I have never been in a relationship. Due to the absence of genitals I have never been able to even pleasure myself. I am still undecided on sex reassignment surgery. My doctor has told me that I have a much better chance of achieving a satisfactory sexual relationship as a woman than as a man. He has asked me to try and live as a woman for some time to see if I am able to adjust to being female. I have decided to act on his advice and that's where I wanted to ask you for some help.
Firstly what kind of clothing should I buy at first? I have little to no knowledge of female clothes. I have never worn a skirt but I have always wondered what it would feel like to wear one. Then what about make up? Do women always wear some amount of makeup? Also shoes. What should be the height of the heels? I would also like to know something about feminine mannerisms. If you can describe some of the etiquette that women follow especially when they are in a dress that would be very helpful. And anything else that you may want to add for someone who is cross-dressing for the first time.
Your situation seems a bit unusual. I can understand how at your age never having been in a relationship and due to your medical condition it is difficult or nearly impossible to have intercourse with another person. However there is much more to a relationship than just sex. Being a friend first is the most important and if you can be a friend first than the person you find (male or female) will understand your condition and the 2 of you can decide on the best way to proceed that accommodates the 2 of you. If you still have a desire to be a parent than adoption is always available. There are many children looking for parents.
Something that does concern me is your perceived gender. If you had not had the accident, would you still have feelings of being female? Transgender people don't just wake up one morning and decide to switch. It's a life long struggle that they deal with from a very early age. Although you may have a more feminine appearance, you seem to identify as male. Making the transition just because you want to be satisfied physically makes me question the reasoning of your doctor. Also what type of doctor are you seeing? Is this someone who specializes in transgender issues, is this a psychologist or a medical doctor? You may find being a female very fulfilling than again you may not.
If you want to try living as a female, the best place to start is to make yourself appear female. The easiest way to do so is with make up, clothing, a bit of padding and a wig. What I would recommend you do is find a close female friend you are comfortable talking to and if she is not aware of your condition tell her and let her know what you are planning and you would like her help. With a little time and practice you can devolve a look that works for you. In years past a womans wardrobe was limited to dresses, skirts and heels however today it is much more open and women can wear just about anything from pants, dresses, shorts, etc. So if you don't want to wear a skirt or dress there is no reason you have to. When I cross-dress in public I will often wear pants, although in a womans style. Begin studying the women around you and notice how they dress and how they carry themselves. It's not uncommon for male to female transgender to start out by trying to look all sexy and end up dressing like a 2 bit whore. It's a very common mistake and this is why I recommend you find a female friend who can help you find a look you will like, fit's your body type and is age appropriate.
Regarding make up, it should fit the occasion. A woman will rarely wear full make up if she is going about her day to day activities. Her job and responsibilities will dictate how much she might wear. Just a little lip gloss and maybe some light eye shadow or blush is enough for day to day stuff. When she is going out for a date or special event she may choose to wear full foundation and a more sophisticated look. This is why women often talk about going from "day to night" regarding their wardrobe and make up. However for many TG people and cross-dressers make up isn't just an accessory, it's required! Beard cover is a must. I don't know how much if any beard you have but women don't have a beard shadow. You will have to cover it up and there are many techniques to do so. Products such as Dermablend or MAC full coverage foundation are fantastic for beard cover.
If you decide to transition, you should consider having electrolysis or laser to have the beard removed. Laser is a faster and less expensive option over electrolysis however it does not work on all skin types. Caucasian individuals with lighter skin and darker hair are the best candidates for laser. If your skin is darker or your hair is red or blonde than you will have to go with electrolysis. This is a time intensive and expensive procedure. Plus it's not reversible.
As for shoes, make them comfortable. If you are not comfortable in heels, than you don't have to wear them. There are plenty of styles of shoes for women in all heel heights. If you want to try heels there is nothing wrong or right about wearing them. Just make sure they match the outfit and are comfortable for what you are doing. If you are planning on being on your feet all day than a 4 inch stiletto is not going to be the best option. However if you plan on sitting most of the night and looking pretty than that might be a nice choice.
Hair style is also important. In most cultures men keep their hair shorter while women will grow it long. So you will likely be allowing your hair to grow. If you are like most men, and your hair is what we refer to as a business or "normal" length, it is going to take about 18 months to grow out to a length where it can easily be styled in a womans style. However you do have the option in the mean time for wearing a wig and there are several types. There are of course full cap wigs that completely cover your own hair and this is likely where you would start. Then there are half wigs which allow the front of your own hair to be visible but gives you a much longer style in the back and the sides. There is the fall, which is more like a clip that gives you more volume in the back but allows your full scalp to be visible. Then there are inserts that clip into your own hair in strategic places and creates the illusion your hair is longer and fuller. Finally there is the weave. A weave is small pieces of individual hairs that are weaved into your own hair. They look and feel very natural. Women who get weaves usually wear them for weeks or months as they are considered semi-permanent. They are very popular with women of African decent, but can be worn by anyone. Having a weave installed is a lengthy procedure requiring most of a day at a salon.
You mention mannerisms and I think it's great you are thinking about that. Women carry themselves differently than men. As you watch and study women notice how they move, stand, sit, etc. Women tend to touch their bodies more and touch others. Women tend to have more physical contact with other women than men have with other men, (i.e. touching arms or shoulders, giving hugs, etc.) However the most important thing is confidence. If you are out in public it's inevitable you will be read as a man at some point. You will give yourself away as a TG. This is where you have to be comfortable in your own skin. If someone reads you at TG than the best thing is not to try to hide or deny it but be truthful and acknowledge they are correct. You don't have to explain why you are the way you are but you can use the opportunity to teach them a bit about your situation. It's been my experience people are more open to those who transition once they meet a transgender person for the first time.
Beyond clothing there are the other issues of developing a female body. Due to your condition it sounds like you never fully masculinized due to lower than normal testosterone levels. This means you will likely respond rather quickly to the female hormones and you will not need any type of testosterone blockers. If you decide to live as a woman you will need to develop breast and hormones will do that. In addition they will cause your body fat to settle into a more feminine pattern, giving you fuller hips and butt. This may give you the illusion of having a smaller waist as well. As your body fat will be more evenly distributed this will include a very small layer on your face. This will help soften your facial features and you will look more female. For most M2F transgenders the breast development is about one cup size smaller than most women in your family. So compared to your mother, sisters and aunts, you will be a bit smaller. The most I've ever seen a M2F reach naturally was a full C cup. Most are in the large A to B cups and therefore require breast augmentation to reach a breast size that complements their body shape.
The direction and how much you choose is up to you. There is nothing that says you have to have any type of surgery to live as a woman. You don't have to change your body or take hormones if you don't want to. If you find after a few months to a year that you are more comfortable in a female role, than you may decide to take the next step. But give yourself time and don't rush anything. There are safe places for cross-dressers to go. Do an internet search and I'm sure you will find some in your area. As you become more comfortable in the female role, you will find more places you will be comfortable going to.
If you have any more questions please feel free to contact me. My e-mail is firstname.lastname@example.org