I think new glasses will help in the long run, I myself am buying new ones this month and hope to find a more masculine frame.... it seems to be an issue for those of us with glasses. My fiancee is MTF and she has the same issue, we are also buying her new glasses this month haha.
I agree with what has been said so far about the first picture, it wasn't the smile, it was the hair. I was actually surprised to see how short your hair was before you cut it in the second picture, the first one did seem like it was just pulled back in a ponytail and that made it seem more female to me. And I do like the new hair cut, I think it went well and didn't get so short that you have that butch lesbian look.
One thing I did before I began T (since I too look like a younger guy) was to use men's facial hair dye to make my fuzz look more like a young man's fuzz when they first start growing their facial hair. It will still be fine and soft (so it will add to the young appearance sadly) but it will also create less doubt at the same time. Especially if you shave the parts of your face that you don't dye.
I personally don't see the hip problem that was mentioned by someone earlier, but the pictures don't really show enough. If you feel this is an issue for you experiment with different cuts of pants and shirts in the dressing room next time you go shopping. I've found for me it works best to wear pants lower on my hips (just above the crotch hair line) and then to wear a shirt that reaches just past the top of my pants. It helps me look like I have less curves, you may find a way to wear clothing that does the same for you, but we have very different body types so I don't have any specific suggestions for you. I personally am very thin so I had a big problem with the hip area, since it is pretty much the only place on my body that appears very female. There are also different kinds of control top under garments for men including long under shirts or even bike style shorts that some of my bigger friends swear by to help shape their body into a masculine look. If you are interested I can ask them what they use or if there is a good site online that sells the items for you to look at. Just let me know