Hello all.
I should start out by saying I'm 62 and haven't had a girlfriend in ten years.
There was no intention on my part to have one ever again, and to just enjoy my single life and dressing.
Out of nowhere a woman twenty years younger has fallen for me. She is currently a co-worker, but has turned in her notice. She is best friends with my assistant at work, and they regularly text.
We haven't been intimate, but that's only because I'm torn on that subject. She would be in a second. She hasn't been to my place because my cross-dressing would be obvious, unless I hid everything, which I'd rather not do.
We have been going out as "friends" to this point, but I kind of blew that when I kissed her last week.
She has seen and liked "Hedwig and the Angry Inch". She identifies as a pirate, and often dresses up as a female one. She loves thrift stores and wants to go shopping with me at some point, now that Halloween clothing and wigs are being put out. She also told me out of clear blue sky that her ex-husband regularly wore women's underwear. My therapist said that was my opening...to ask how she felt about that...but I didn't say anything.
I really like this woman...although not as much as she likes me...and possibly getting some after ten years sounds good, but I really don't know how to proceed per the CDing subject.
Any suggestions or thoughts would be very appreciated!