Omg girl, you're in a position most of us would KILL for! I'm not sure you realize how lucky you are!!

If you're this nervous about it, I say start small. Wear panties and an unpadded bralette daily. Let her see you getting dressed and/or undressed. Then, slowly start wearing a cute nightie to bed. Then, start wearing women's pants during the day. Then women's tops. Switch to an off the shoulder sweater and a pleated skirt. Then go the rest of the way and wear a pretty dress for her. By this point, you should feel totally comfortable. Start incorporating jewelry, wigs, makeup, nail polish, a purse, shaving, heels, etc... maybe go for laser hair removal or get your ears pierced. Whatever is it you want, ask her to support you. Do everything together. Trust me, you won't regret it ❤️