We discussed this in PM, but for others who may be reading:
You should be able to request a name change on your high school transcripts with the public school system that you were in (Fairfax County, Bland County, City of Falls Church, etc.). You will probably have to pay extra if you want a re-printed copy of your diploma, but all that you really need from them is the transcript. To do all of this, you would first need to have your name legally changed and be able to provide them with a certified copy of your court order. Your local court system will give you I believe 2 copies of these for free, but it may be a good idea to buy a few extra. You should also make copies of them yourself and hang onto the original.
When you apply to colleges, they will just need a copy of your high school transcripts. As long as your name is updated on there, they won't have any issues. If for some reason you are unable to update your high school transcripts, most universities and colleges will probably be fine if you submit to them a copy of your court order for the name change in order to register.
If you have completed college and want to change your name there, you just need to contact the Registrar with a copy of your name change. They can update you in the system and that will update the name on your transcripts which you would then take to employers.
Hope this helps! I didn't update my high school stuff because I already had 2 degrees by that point, but I would be surprised if there was any resistance to it.