My Sister And My Cross Dressing

At first, my sister wasn't please about me cross dressing. It took a few months and my two week visit to my aunt's house in Cleveland.

When we returned from our vacation, we still about 7 weeks before school started. I began setting my hair more often. The first Friday after we got back, we were going out for dinner. I had set my hair during the day and brushed it into a really nice style. When it was time to get ready to go to dinner, I went up to my room to pick out some clothes. I looked in the closet, and I had dresses and boy's clothes. I was going to have to make a choice.

When I came down for dinner, I had one of my new dresses on that we bought in Cleveland. It was a light blue flowery print that went just to my knees. I also had a new pair of white shoes and white purse. I put my makeup on after getting dressed. I didn't know what my mom or sister would think about me going out with them as Mary Beth.

My sister, who's opinion I feared the most, just smiled. I'll remember her words forever. "I realize now, that I have a little sister that I can love. Nothing's going to change that, is it, Mary Beth?"

"I hope not," was all I could get out as I felt like crying at the time.

My mom seemed unfazed by my appearance. "You look nice, Mary Beth. You going to be okay going out in town like that?"

"Mom, I'd been setting my hair all day. I think it would look odd if I went out as a boy."

So we had dinner at Roma's, our favorite Italian restaurant. The waitress didn't seem put off with me there, and I think she just thought I was a friend of my sisters. After dinner, we went to the mall and walked around. I stopped in a Penny's to look at some dresses, and my mother bought me a couple of night gowns and a new robe. She thought I should start wearing them instead of the pajamas I'd been wearing.

There was a makeup store at the mall and we popped in. I bought a new shade of lipstick, but that was about it.

When we got home, we all commented on what a nice evening it had been. I went upstairs to get ready for bed. I put night gown on and the pink rob my mom bought me.

We spent the rest of the evening watching TV, all in our night gowns and robes. I kept my makeup on, just because. I took it off with cold cream before I went to bed. Moisturizing had become a regular part of my routine, and my sister is the one who had gotten me to start.

My sister and I got very close that summer, best friends, really. It really made a difference as I probably got to where I spent at least of third of my time dressed as a girl, weekends and nights.

I see where so many of our community have to live in secret. I'm sorry that's how it is. It's really a shame. If my family could contribute, I think they'd say being out in the open is best for every one around. Maybe I'll have my sister write one of these to let everyone know how important it is.
marybethme marybethme
51-55, T
7 Responses Jan 21, 2013


My sister was the same, when my sis found out she kept teasing me and I kept right on wearing her clothes, Sis finally gave in and made wear all girls clothes and finally made me a girl full time.

Thanks for the story, it is nice to hear that some of us get to be out of the closet. Will look for the story by your sister, I really want to get her perspective.

A wonderful feeling to be yourself..;-)

My mom and sister accepted me as a sissy at 8yrs old and we grew up in the 50 & 60's. In my teen years, I had girls and guy friends at school and they did not accept me at all once they saw me at home in my dresses.
My sister told everyone she knew and they all disowned me. It hurt at first, but I'd been a girl for several years and I decided I didn't care what they thot, I was gonna do what I liked.
In my senior school year I was laughed at, called sissy names, even some of the teachers called me names. I graduated in a cap and gown like everyone else, except I was wearing a bra,panties and nylons underneath.
I sure hope eventually people will except us more. I still get a lot of crap from being the girl I am today.

That's a horrible thing to go through for just being yourself. I hope opinions of CD and TG people change to more tolerance and acceptance over the years so young versions of us don't have to feel like outcasts. Hugs hon

Thank you for caring. I hope so too. It's too late for me, but I hope those younger will have a better experience that I had.

I am with PHSensi on this- I think tolerance is improving. Many parents are now accepting of gender and sexuality differences because what really matters is that you love your kids. You want your kids to be happy.
In contrast to your situation, Mary Beth's mom and sister were fully supportive and welcomed their new daughter and sister more than 30 years ago.
Things were very different in the 50's and 60's as you accurately note, but your sister was disloyal to you as a brother who needed a friend, which is a shame. Consideration and support for others is so important. I wish you had the same support network as Mary Beth is still able to rely upon.
What matters is whether a person is kind and thoughtful. Who would I rather have as a friend or colleague- a jerk who is straight or a kind soul who is, well, let's just say different. Easy call for me every time.

Be yourself and ignore people that complain, wear what you are happy in.

The world would be a much better place if everyone thought that way. If would could let people be themselves; be they different or not. Hugs to you all!

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I also wonder how accepted cross dressing would really be if more people were able to be open about it. Growing up I remember knowing at a gut level that my dressing was wrong. Later I realized that it wasn't wrong, but it wasn't accepted either. It took me years to realize that I'm not a freak, but just different. And different is good in many ways.

Thanks for your comment, I think open dressing won't come for a while.

Yeah, I think you are unfortunately correct. But the younger generations seem to be more accepting so there's hope :-)

I didn't know I was a freak when I grew up, I just thot that's the way I was supposed to be. As I got older, I knew other guys didn't dress as I did, but by then I was already hooked on the dressing.

You were not a freak then or now. You were yourself.
Some of those guys undoubtedly dressed, but just weren't willing to admit it.

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That's so neat that you were able to develop such a close relationship with your sister. I sense your entire family was something special.

I had no idea how, until joining here, and seeing how many people have to dress in private. I feel so bad that more can't just go out as they choose. Just think, if every cross dresser went out in public or came out, it wouldn't be such a taboo. Maybe.

Many of us grew up with Dads and Moms that didn't understand boys who had some girl (all girl in some instances) inside them. And didn't have a sister. Your Mom was remarkable. In the late 50s and early 60s, parents had no clue about cross-dressing and gender. Not that it's easy now for a boy growing up, but I do think parents better appreciate in 2013 that there are many variations in a boy's experience and can address them and support their boys.

I agree with Kim1girl too. My mom and sister didn't know anything about "cross dressing, but they didn't feel any shame at what they did to me. In the 50's most girls and ladies wore lots of lingerie than they do now. If you look at the girls today, They don't wear dresses, they are wearing skinny jeans and cotton tops and some even cotton underwear.
Not much nylons or slips anymore, I wonder how some of the younger boys get interested on the cross dressing today.

I think that just shows us that the girl inside is already there. Pantyhose etc may have been the gateway for us, but that girl screams to get out. The younger cd’s have their own trigger mechanisms from a culture that defines femininity in a slightly different way these days. I knew a young CD that was really into black rights, but more so into white KED sneakers

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