PM me if you want to Skype we can set up a time. Probably Sunday.
So to start lets address your photo. Their are some easy fixes we can make. First off always smile in photos. Frowning, and non smiles give a more rigidity, and thus more masculine feel to photos. A smile does add some femininity to a photo. Enough to begin tipping the scales. Takes photos with the camera above you so the camera looks down on you. This gives a forced perspective of smallness. It makes you look smaller, and more feminine. In photos try and wear something distracting not flashy but distracting. http://imgur.com/GVXSyo7 This is a really good example of the clothing I am talking about. Layers, clean lines, designs, all make for a distracting more thought out look. Remember that females usually look like they have more thought put into their outfit than guys. Simple tricks like wearing things with designs , and patterns can create that illusion.
Next we can talk about some simple gender neutral changes you can make by yourself to your face. Doing your eyebrows or simple thinning them can take away a lot of masculinity from a face. Start wearing chapstick and lip balm everyday to heal your lips. If you can see the chapping in a photo you need chapstick. It softens the lips making them smoother, and even glossier looking. Again adding femininity while erasing masculinity.
If possible get a hold of some more gender neutral glasses, yours work but they do have a slight masculine lean to them. Anything with color is wonderful blues, greens, yellows, reds all gender neutral colors that can also add some femininity.
Your hair in my opinion is actually OK. I can kind of see a 80's geeky girl style to it. If you don't like it go to a salon and ask them for something gender neutral with a feminine lean. Or find a look online you like. Call around and find a salon that is ok with MTF transgender client if your nervous.
As for some basic things you can do to ease yourself into transition I have several ideas.
Buy and wear shape wear. This is a type of underwear woman wear to help them shape their bodies. It can help give you subtle lines, and help hold a tuck in place. If you are small enough it can eliminate the need for a tuck as well.
The next thing you can do is actually in my ideas above. Wear chapstick and lip balm everyday. Literally every single day. They are clear, and glossy not enough to tip any one off though. They allow you to have the felling of something on your lips though which is wonderful.
Next up is clear nail polish. Wear this stuff everyday. Remove and reapply once a week minimum to help you learn applying techniques. It will hive you the feeling of something on your finger nails which can act as a huge confidence booster.
Woman's T-shirts are a transgender girls best friend in early transition. You can buy them for cheap, and no one will ever know the difference. You will though and it will be amazing.
Woman's under shirts, and underwear. Both of these will not be see by most people and hopefully anyone your intimate enough with to see them is ok with your gender identity. Make these as girly as you want. I often wear girl tank tops under my shirts on a everyday bases now.
Girl jeans can be wonderful or scary. I have a pair of Levi Comfort fit waist band jeans. They look just like guy jeans. In fact i wear them every single day almost and no one has ever asked me a question about them. They have smaller pockets so if someone is watching you like ridiculously close than they might question that. Pocket size is not a gender Que for clothing though. I have male jeans with no and tiny pockets. You need to be careful with this one though as if you buy something to tight, or with a girly desgine on the back or something you could tip someone off that they are girl jeans.
Toe, and ankle jelery can be easily hidden with shoes and socks. Giving you another layer of femininity that you can show off or hide to your hearts content.
concealer, and foundation are not girls makeup. Their isn't really girl makeup. I have been making indie movies since i was a kid. Trust me when I say that if two 13 year old boys can go buy cover girl blush, and nail polish makeup is gender neutral. Foundation in particular is amazing It can give you the appearance of smooth skin, small pours, and just help you look amazing. You and me have about the same skin tone, and I have worse acne spots than you do so trust me foundation is awesome. Plus no one really notices it. I have worn it out many times and no one not even my family has said anything.
If would be ok with pushing it a little getting your ears pierced is an option. I have a totally cis, and straight friend who has his ears pierced. Its super hip, and rock and roll, and just plain cool! or so he says >.< It can be feminine though and in your case that is what would matter.
Anyway I hope this helps some please feel free to PM me if you want to Skype sometime. I am not free everyday but I am free a lot of the time.