I'm very new here (joined today in fact) but I do believe this is the best place to discuss this so here goes:
I'm mid 50's been in a LTR with a woman. I have always felt like (at a minimum) a crossdresser edging toward trans. I know they aren't the same but I also think its a giant area of gray. A long time ago I made the decision not to do much about it because of my personal life. It's a decision I am frustratingly comfortable with.
About a year ago i had a bit of a health scare and found my leg was swollen, they checked for a clot and it was all good (whew) but the doctor suggested i wear compression stockings. I started wearing those but they pulled the hair from my legs so I started shaving them. I always wanted to, but this gave me an excuse. My SO was okay with it too. well.. I have skinny legs and they kept slipping so I decided to wear a garter belt and also found some compression stockings that were def more feminine and more sheer and just felt better, so daily I started wearing stockings and a garter belt. My SO was just fine with it. In fact, she suggested I become intimate with her while wearing those. I told her how much that excited me and soon she bought me 5" heels to add to the fun.
I was having trouble with my underwear bunching up so she suggested panties. She had some hipsters that fit me pretty well and I told her how much better they felt on me than my old male underwear. I now have a drawer full of them that she helped me pick out
We got on the subject of clothing and I told her that I loved crossing my legs with my stockings on. I asked if I could try on her skirt, we both chuckled for a bit as I did, but i told her I really liked it. She said she was okay if I bought some stuff for myself.
Currently, I sleep mostly in nightgowns and panties, I have a dress of my own and a couple pairs of heels.
She has put a line up though (that I want to cross so much) that I am respecting
*No Bra (that is a huge turn off for her)
*nothing above the shoulder (no make up or wig)
*no shaving my stomach, chest or arms
Since we have started this in earnest (prob last 3 months or so) I have been super amorous to her. I want to make sure that she knows that the more we go this direction, the better it can be for her as well
I am curious if this is something that others have experienced?
What might I expect from my SO?
Do you think she might relent on her restrictions or is this a fair compromise?
I know everyone's experience is different but I am afraid if I rush it, she will ask me to put a stop to it and this Genie is out of the bottle now...
Heather
edit:spelling and grammer