I am 56, having crossdressed passionately since age 49 Will be retiring in the next year. I am not out of the closet only with GG GF and an BF admirer.
My story:
1st grade- Discover there are two anatomical genders, and their clothing is different. Wanted to wear the tights etc found in clothing dryer. Caught by my mother dressing and sent to counseling (epic failure).
Age 5-15- Take private moments to find and wear girl's clothes, testing out the feeling- exploring my urge but it is difficult and sparse. Realize that sexually I have feminine inclinations. I too enjoy being feminine in sex, I finding erotic stories in penthouse variations magazines. I could be a bi-sexual????!
Age 21- 40s Tried with ex wife and she was not supportive of dressing and underdressing and openly mocked at parties by her, when she drank too much, which was a lot. We break up because she cheated and meant to be.
Age 40-51 Married again 2001 and wore hose to bedroom with second wife to have fun etc. She allowed me to openly dress and told her while dressed I had a bisexual feelings while I was with the other gurls I met at the events. She too opened up and finally, she admittedly announced she was initially bi and eventually admitted she was gay. We divorced and she moved in with your new significant other. She feels so bad but I helped her find her inner person she had not yet understood and her years of confusion, as to mine.
Age 54-56 Met a new GF and I openly admitted while dating who I was and felt. The new live in GF supports and encourages me to dress. Other than my height, wide big shoulders/ "V" frame I rock out in skirt and hose/heels....I do and can go out and express my inner gurl but I am very cautious of co-workers finding out (JOB) to fakes to flakes.
To be continued as the arc of the world turns as Kara...