I'm a 58 y/o man, who is a crossdresser. Not once in a blue moon, not sneaking into my wife's or daughter's ill fitting clothes, not just panties or heels. I crossdress fully, with makeup, jewelry, accessories and wigs. I have a complete female wardrobe, and I'm a stylish size 12 dress and 10 shoe. I am 5'5", 130 lbs, and can comfortably and confidantly go out in public as Marianne (my female name) and not be detected or read as a man. I truly love my life, and have a responsible, well paying, white collar job, co-own a home, have a nice car, and many friends. And being Marianne is a big part of my life.
I was probably 8 when I first tried on my mom's high heels. She wore a size 6 shoe, which fit me perfect. I was always careful to hide this from mom. It was just me, her and her sister (my aunt), who was 16. My aunt caught me trying on moms clothes or her clothes a few times, but she was always cool about it. She always kept my secret, and by time I was 12, was helping me play dressup in her clothes. She taught me makeup and how to walk and talk, and when I look back, I was a 12 y/o boy dressing like an 18-19 y/o woman! When I was 11, I summoned up the nerve to ask mom if I could dress like a woman for Halloween. She allowed it, and I did it again at age 12, lookin oh-so-Lolita-like! Since my aunt was taller than mom, her clothes and shoes were just right for me, those nice early 60s fashions my college age aunt wore. At 13, I wore my aunts prom dress from HS, lloking oh so feminine. Mom was curious, but never made an issue of it.
Meanwhile, I was playing dressup at least 3 times a week with my aunts help. My aunt went out on her own when she was 25 and I was 17. I made excuses to visit her when I could to dress up, and become "Evelyn", the same name of a girl I had a crush on in HS, but was way too shy to ask out. I had a pair of size 10 black 4" heel pumps at my aunts house, as her size 8 shoes were now killing my feet. Eventually my aunt got married, and I went on my own, and was crossdressing regularly, building a wardroce. By 32, I got married. My aunt and I remained close all the way thru.
My mistake was not telling my wife ahead of time that I crossdressed. When my wife found out my secret, it was the beginning of the end. We divorced when I was 35. I remarried at 40 to a 30 y/o woman I met when I was in drag, so she was cool with it. Until she grew tired of good-girl 'Marianne', the fem name I adopted in my 20s. Her level of kink proved to be too much for me, who was always more of a lady, the girly-girl who wears a nice dress, pearls and heels to clean the house, like 1950s-60s sitcom wives. Who wears hose until it hits 90 degrees, and sandalfoot hose with sandals. Who gets pedicures, reads Cosmo, and occasionally watches Lifetime and We. When she insisted on tieing me up, paddling me, making me do 100% of the housework, or that I do 3-somes with another man, I resisted. I kinda knew she was cheating on me when we divorced 5 years ago.
My aunt divorced 7 years ago after almost 29 years married, with 2 daughters in their 20s. They know their cousin has a strong feminine side, and are as cool as their mom. 3 years ago, with my aunt divorced and an 'empty-nester', we discussed living together. As 2 going-solo divorcees, it made total sense. Since she was in an apartment, after selling her house, she moved in with me. She is a spry, active, young looking, young acting 66, and we make 2 very cool mature ladies.
I look like I'm in my mid 40s, and my aunt looks no more than 50. She marvelled at my makeup/vanity table and my killer wardrobe, plus the fact that I sleep in nightgowns or lingerie, and wear panties 100% of the time. It's almost like we turned back the clock 45 years. We go out as women, to a movie, dinner or the mall, devoted high heel wearers! And this past summer we went on vacation to Fire Island for a week, a trip where I took NO mens clothes with me. We musta looked like 2 mature lesbians! Since my mom is deceased, never knowing I crossdressed, my aunt is my closest, most beloved relative. My cousins are a total delight, very liberal and openminded, and I have told them not to hide the fact their cousin likes to work his female side. They have even introduced 'Marianne' to their friends! I'm also looking to get back into dating, but all I attract are men!! I mean I love being that femininely attractive, but I am still straight. Living with my best friend, my mentor, my fave relative!!