You see I hang out with these guys( they are all straight cis-gender males) on a regular basis to role play dungeons and dragons, play video games, and or just general hanging out. I want talk to them about me needing to start the Outward part of my transition to female. Clothing, make-up, the works. They all know I'm going to transition sometime in the future when I can afford to. I told them about two years ago and sense then I've lost money due losing hours at work.

I don't want to come off as a (insert bad word here) with an agenda to them. Giving them an ultimatum which in turn will get them really mad. These guys are the only friends I've know since high school and are the only friends I hang out with on a regular basis. A couple of them have family/their friends, that they live with. To whom are uncomfortable with me "turning" female and yes they know as well. I do dress very androgynously when I'm around them. For me that is not enough. I want to go over and hang out in a skirt and heels or a dress if I want to. On days that I want to feel that little bit more girly. 

I guess what I'm asking if anyone has any experience with this kind of problem and how did you over come it?
I also talk to them quite often in Skype. What can I say, we enjoy each others company.

Hi Amrisa,

I guess you are nearing the cross roads with these friendships, that in some time soon, may undergo a massive transition within itself, due to your transition. What I'm saying is, that for very change you make towards your final goal, will determine and test the resolve these friendships can sustain.

This will be the litmus paper to your future support network. Bearing that in mind, now may be a good time to start looking for a support network that will out last your transition and propel you into what may seem an unbelievable future for you.

You could 'test the water' by asking each individually, how your wardrobe affects your relationship with them. You could also add, how would they feel if you dressed more appropriately to the gender of your choice, and observe their reaction. For this you'll know, who is for you, and who isn't.

Hope this helps to some degree, and it works out for you. Embrace and enjoy your journey. Let us know how it works out.

Be safe, well and happy
Lotsa huggs
Catherine

I handle peoples discomfort by voicing what I think they are thinking in a joking and relaxed way. I try to get them to open up and talk to me... then I can find out what the real issue is, and figure out a way to make things work. Humor is a GREAT way to get people to drop their guard

Basically, you gotta find out WHY (if) your friends have a problem with things. Also, try to understand things from their point of view... and try to understand the level of "normalcy" within the group.

Are the things you want to wear actually going to work with your body? Or will they make you stand out as they create a conflict of presentation?

Most likely your friends just think if you start wearing super girly stuff you will just look strange (and honestly, that is a very valid train of thought! I don't dress in girls clothes yet because I really can't pull it off atm).

Talk to them about it, get their input on what they think might work on you. Say you want to update your look, but trying to figure out what to go with.

When you pull them into the decision process they will naturally feel more a part of the outcome... and that means they are less likely to fight against it (since they will feel as if they have some ownership of the new outfit choice).

I think that you should just be up front and ask them what they think. Since they already know it's coming, and seem to have fully accepted it, I bet that they'll be fine with it. Discuss their concerns, possible boundaries, etc. Assure them that you'll be tastefully dressed, in any case.

Are you wanting to do this because it's time to start the RLE, or do you just want to start being outwardly female more?

I agree with rabbit, look at it with a slight sense of humour, so nobody is too freaked out or surprised by it. If they have laughter to relieve they're tension then they'll relax and the first time(s) will go much more smoothly.

I'd also suggest making small changes at first - dont go the whole go for the whole "disney princess" look straight away. Gradually introduce more feminine clothing into your general appearance. A pair of jeans and nice heels can look very modern and female, and wont freak many people out. Maybe another day you could wear a feminine top, instead of the typical androgynic baggy clothing that mtfs tend to favour at first (sorry, this is a generalization - i dont know if it applies to you!), so that the top reveals your new feminine body shape? If you make small changes, it will be less of an abrupt shock to them and i'm sure they'll start to associate you with these new items of clothing and when you finally feel comfortable enough to wear what you want to wear, im sure they'll be supportive and positive about it.

x