My wife has always known about me being a crossdresser. We started dating after being introduced by a mutual friend I was swapping clothes with. She was okay with it. However, due to living so close to parents (apartment attached to their house) and budgetary constraints, I never got to explore much. Eventually I pushed things a bit too far and ended up purging and practically going into hibernation because I didn't want to upset my wife. This lasted for probably 2-3 years. The furthest we got after that was her buying me panties for valentines day about 3 years back now (so it's been around 6 years since I've done anything beyond panties, and even that became less frequent)
Well, early last month I brought it up to her again (as I had before) and told her I was sorry I had pushed too far before. How upon reflection I found that I wasn't interested in going that far, but I did want to explore crossdressing.
So she grudgingly agreed to a DADT relationship. She wouldn't freak out if she found clothes in the laundry, and I could ask her to go shopping if I wanted some dressing up time. Also, we're much better off financially now, so my allowance can go toward almost anything I want.
After a week or so of DADT I mentioned I appreciated it, but I don't care for hiding things. I felt like I had to be sneaky about it. Our relationship is built on 100% honesty, and sneaking around isn't what I wanted to be doing. She took that to heart, and we had a great discussion. Mostly about the where I had tried to take it before, and other things I had been interested in at that time. I think that put her mind at ease. One night while watching TV she said "do you want to get dressed up?"
After that she decided to let me try on some of her clothes (off limits, normally). And then a few days later she said "do you want me to do your makeup tomorrow?" That was two weeks ago. Now she seems practically fine about all of it. She's helped me do a bit of waxing, and even said I look good. Wow. I never thought I would hear that, lol.
Well, on Sunday we went out and did some shopping. She picked up a few things, and even picked up a pair of shoes for me. In the last year I've gone from a size 13 to a 12, mostly due to width (losing weight) and now I've managed to slip into a women's 12. There are a few places around that have that size.
When we got home she said she couldn't wait to show me my valentine's gift, but I couldn't actually have it until Valentines day.
She picked out an entire outfit for me! Shirt, jacket, skirt, shoes and even a necklace. Along with it she bought me a new movie and some "spa day" items. We'll be having a girls day watching movies, doing makeup and face masks on this coming Saturday!
I know it's a long read, but I had to share. Call it bragging, I'm just excited that my wife knows me so well and has gone out of her way to accept this. I try not to press it, but I try to make sure she's not just doing this all the while torturing herself. I can tell she's actually starting to get into it, and I can only hope it keeps up. I just have to remember to let her move the line, not me.
Thanks for reading!
Originally Posted by FeliciaMCD
I hope you enjoy your present! Make sure to spoil her too though! 
