I'm a 23 y/o str8 male crossdresser. My GF is a wonderful 38 y/o woman who not only tolerates my crossdressing, but encourages it. Which is major because I spend almoct all of my non-work time dressed as a woman. I started tryin on my mom;s clothes when I was about 8. Mom had me when she was 42, and always wanted a daughter, so she always let me dress up. She even bought me my own female clothes starting when I was a tween, and by age 10 I could easily walk in heels. My current GF was our neighbor who had a daughter, Tia. Since both our moms worked, I looked after Tia after school starting from when she was 8 and I was 15. I never hid my crossdressing from Tia, and she thought it was cool because I was just like a girl. She also never told her mom that I crossdressed. As she got older, our friendship grew to where we were BFFs. When she hit 13, her mom felt it was no longer necessary for me to 'babysit', but Tia and I continued to hang out together. Tia was also my size and 2" taller than me (I'm 5'6").
She sometimes let me wear her clothes and shoes and practiced make up on my face. We were like sisters as well as best friends, and her mom adored me. I finally came out to her mom that I was a serious crossdresser. Tia's mom assumed I was gay, which was OK because I wasnt seen as a threat to her teen daughter. I got very friendly with Tia's mom, and she would confide in me very personal stuff about her relationships. She also helped me refine my makeup and style skills, and helped me realize that I could EASILY pass as a woman in public. I now had 2 BFFs who accepted me as Linda.
Tia's mom had a bad relationship with her BF, and finally broke up with him last year. I was there to help her thru the aftermath, basically by being a really good friend. We would hug, and I would be reminded that altho I am very female acting, I'm still str8. And Tia's mom is a tall, very attractive woman. I'm 22 and still a virgin, so I finally confessed to Tia's mom that I was str8 and found her very desirable. After much convincing, we started dating, with me actually dressed as a man. We finally got intimate, and she took my virginity. We are lovers, and she loves having me as a a BF and best 'female' friend too. Tia, now 16, loves that her mom and I are a couple, and Tia and I share many clothes and shoes.