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My Sister Taught Me To Crossdress Mother Taught Me To Love It.

At first, it was just a game. My sister wanted a girlfriend to play with and I was the only one around the house. I was 8 and Cin was probably 10. We had fun pretending and all day she dressed me in different skirts and dresses even though most were too big. At the end of the day getting ready for bed, sis wanted me to pretend I was visiting her for a week and she wanted me to wear some of her jammys. We lived at home with my stepmother as a single parent family and she thought it was harmless fun and was happy to see her real daughter, Cin, out of her mood. It was probably then that I began to feel closer to them than I ever felt before. And it gave me someone to bond with since my dad had passed. Somewhere along the line, mostly with my mother's encouragement, I learned to love how girl's clothes felt.  Eventually, I even learned to find comfort in my mother teaching both my sister and I to be proper young girls.

Before "vacation" was over, I discovered the embarrassment and excitement of shopping for a new wardrobe of all new girlish clothes for me. By that time, Mother had put curls in my somewhat long hair and dressed me in a bright yellow sundress, flip-flops and pink painted toenails and eventually, even panties and a bra. I was embarrassed as she pulled me to the car ...then very definitely ashamed for the first time in my life as I stumbled through the mall seeing so many young boys my own age in jeans and tennis shoes. At some point, probably once I realized my secret was safe and with Cin pulling excitedly at my arm, it would be fair to say my emotions moved to being excited ...and then nothing less than thrilling. I think i remember every single store we went into that day.

Through the teenage years I was home schooled and learned to be comfortable in all sorts of girlish attire, and more importantly, with myself. Yes, of course, there were times I wanted to be a boy again, but my mother always found a way to remind me how much I loved being a girl. Now I am a few months out of my teen years living with my sister and trying to find where my heart will lead me.
kayleew2000 kayleew2000 18-21 32 Responses Mar 27, 2012

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Lovely story. I wish I had an "aunt" as nice as your mom.

Life with my mom wasn't all sugar and spice but we ultimately found our happy place. Thank you for your comment and I hope you get your wish next time around. :-)

Love this. Lucky girl.

You had a wonderful start to your dressing! A family who loves you! They are pure gold the both of them!

Thank you. Actually, my life is more than just about "dressing" now ...its about finding my way as a girl.

You are so fortunate to have such a loving and close relationship with your sister. The fact that you live with her tells me that she is still very involved in your transition, that's wonderful!! Keep us updated, we are waiting to hear more

I remember starting to dress when I was around 8. For the longest time I thought something was wrong with me. When my mom found part of my panty stash she said it was just a phase. When the internet finally came around I realized. I'm surrounded by people just like me.

You have a wonderful family and your mom has given you a wonderful gift of her acceptance and her knowledge of being a woman. What you do with it now is up to you. Enjoy your journey. Your in such a great place and a lot of us wish we learned what you know and had the chance to be able to dress growing up.

Thank you for sharing

It sounds like you had a pretty supportive mother. I would have imagined you continued to dress up since you mother was willing to look the other way ...but it sounds as if you gave it up for a while. When did you finally let the girl inside come back out and play? For the most part I have enjoyed the journey ...and with support from my family I got through the trying times.

I forgot to say after she found my stash she threw them away. Lucky I had more stashed in the back of my speakers. Lol. I did slow down a little when I joined the military. Always had panties and some other things with me. It was kind of hard to dress when you have a roommate. When I got married I had a place to put stuff again and came out to my now ex she was fine with it. It started again after that

Was it the dressing that lead to your wife becoming your ex?

No not the dressing. She didn't care and I could wear what I wanted when ever I wanted.

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I wish I could dress up for my sister and have my family approve. So far I am still a closeted crossdresser, and will probably remain that way.

You might consider just dropping a little hint to your sister and see how she responds. Isn't it worth taking a little chance for the opportunity of discovering something greater about yourself?

I wish my mother would have encouraged my femininity when I was young. It would have been so helpful.

How fortunate for you. When I was your age I had to toss all my silky long nightgowns and panty's as I was entering the USAF for 4 years. While in the service I married and sadly never told her of my adolescent love of sleeping in nightgowns and wearing panties as I; 1.) never thought of telling her and 2.) had pretty much forgotten all about it. We raised 3 wonderful children and when our 3rd had grown and left the house she announced she no longer wanted physical relations! I suspected there was something going on as sex was a very rare experience after his birth. Eventually my feminine feelings and needs began to resurface. My employer began sending me on overnight week long business trips about this time. It wasn't long before I was spending my off work time away shopping in lingerie shops in the malls. What a nervous time this was at first and eventually as clerks got to know me it was a truly thrilling experience. Oh the joy of those nights after a shopping trip trying all those silky satin items on back in my hotel room! After one trip my wife discovered my stash in my suitcase and all h _ _ l broke out. To this day she hates the idea of my satin nightgown wearing and sleeping in, my full time satin (colder weather) or silky nylon (warmer weather) panty wearing! I doubt she has any idea of the extent of my Berta things, sadly. You and the many others we read about on EP that have accepting and supportive folks in your lives are the envy of all of us who are not so fortunate!

Please, please enjoy your femininity and make the most of it as you have your whole adult life still before you quite unlike this 73 year old "closeted" CD'er!

Berta, 9-23-2013, 2:29 AM EDT

I am so sorry that Berta has had to remain in the closet all these years. Of course, I've had the support of my sister and mother for most of my life ...well, they were more than just support. They actually promoted the idea with me until I embraced it on my own. Now, I can't imagine having to live my natural feminine persona by myself. If we are favored with another life, I wish you get to enjoy yours as the pretty little girl you imagine yourself to be in your dreams.

Thank you Kayleew,
How fortunate you were to have such an enjoyable life with the support of your mom & sister! You've shared a very sweet and kind message and I've often wondered if I was a female in a previous life and sure to hope to be one in another life if such is possible!

Berta, 10-22-2013, 7:40 PM EDT

If you are content with the way things are, you don't need to go any farther unless you would just want to do the surgery. There are some things I would really like to change but I am very happy with myself right now.

There is nothing better or more beautiful than seeing the world from the feminine side if you are a male. Although I have lived my life as male, it would not be hard for me to live it as a female. I've been on hormones for twenty years and life is sweet.

I have also been on hormones for some time and can\'t possibly see myself anymore as that little boy from years ago. Thank you for your thoughts.

I wish I could have lived your experience when I was young. Actually I wish I would have come clean with my mom about my feminine desires when I was young. I had ample chances but always denied I had been wearing the clothes. To this day I am sure she knows or at least has her suspicions about my feminine desires. I always have to wonder if I could have lived my life as a girl had I told my mom. I am contemplating on telling her now. I think it would lift another ton of weight from my shoulders. You are young enough to go what ever direction fits you best. I wish you the best of luck and much happiness on your path through life be it male or female or somewhere in between.

Thank you, Kay. I never thought my childhood was all that enviable but I do think it would be nice if all kids had an opportunity to explore their inner fantasies. It sounds like you at least dabbled in dressing at an early age. Perhaps you would have been someone who could have embraced a feminine lifestyle from an early age. Maybe in your next life you will have the chance :-). As for me, I know my road will always be walked wearing heels and rose-colored glasses ...I just haven\'t decided yet if I\'m ready to give up all aspects of being a boy.

Well from this side looking in it might be enviable. From your perspective maybe not, I totally get that. I agree all kids should be allowed to be who they feel they are within their soul.

I have been dressing since at least age seven. It has always been a huge part of me. I wish I would have come out about it as a child so I could have gone puberty as a girl rather than a boy. Now it is to the point I need to express my inner female. I can no longer keep her under lock and key. The inner conflict has come to a head and I am learning to embrace my inner femininity.

I wish I had your courage, especially at such a young age. My older sister used to dress me up in her panties & nighties and I loved it but daddy did not when he caught us. I was 5 and my sister 7 when it started.
I still regret not experiencing life as a girl. Had a chance with a hot, sexy buddy and his overly sexual girl when we were all 20 to take off for several weeks. I know she would have loved a ********* and especially dressing me up girlie, shaving my body ect..... I still fantasize about that. I am jealous of the life you lead!

Thank you for your comments. It didn't really take courage for me to do what my mother wanted. In fact, it might be argued for the opposite. Certainly I learned to accept and even enjoy the new relationship with my mother and sister, but I have on occasion wondered where my life would be if I had the "courage" to resist the excitement of being one of the girls. Isn't it amazing that your brief introduction to panties and nighties at a young age still drives your fantasies. Can you imagine where our world would be if all boys spent a year in skirts and panties?

The world would be a much better place! I believe we are all inherently bisexual but limited by societal norms.

I can't argue with that. Seeing the world from both sides of the gender fence has given me an appreciation and attraction to people based on who they are and not whether they stand up or sit down when they pee.

You are still young so take each day as it comes,enjoy new experiences and when you really know what you want then go for it.

would like to be your daddy and have a family like yours

Since you feel so comfortable in all sorts of girlish attire do you have your ears pierced? How did you feel when they were pierced? If your ears are not pierced, have you ever thought about gettting them pierced?

My wiife pierced my ears for me many years ago. I felt that was a very defining moment in my life. I had worn screw on earrings for several years, but when I was not wearing them there was no evidence I had ever worn them. But having my ears pierced was a permanent commitment to my feminine persona. No matter where I went or what I was doing, whether I was wearing earrings or not, I would always have those little holes in my ears. I could go without earrings, but I could never "unpierce" my ears.

Thank you for your comment GWE. I completely agree with you that earrings have a profound affect on one's life whether they are a boy or a girl. I wrote a story a few months ago called "I Think Earrings Were the Last Straw" which recalls how piercing my ears really reshaped my own image of myself it obviously has for you. It sounds like you have a wonderful, if not interesting relationship with your wife. How much farther did she let you take your feminine persona?

It is not a question of how far my wife LET me take my feminine persona as how much she ENCOURAGED me to take my femine persona. When my wife and I were dating and things were getting serious between us I felt I had to tell her about my feminine persona. I was very nervous about that because I had no idea how she would react, but I knew I could never give up my feminine side. To my surprise she replied by telling me she had had some lesbian experiences before we met and that she was attracted to me because of my feminine persona. When pierced ears were becoming popular and it was getting difficult to find screw on earrings that I liked, my wife was the one who suggested I get my ears pierced and in the end she was the one who actually pierced my ears. I won't go into details, but I will just say that some of our most treasured memories, both in and out of the bedroom, are from times when I was dressed completely en femme.

It sounds like a wonderful relationship!

nice story i would love it if my mother would have said me to be girl and wear girly clothes at the age of 10

If we get a chance at a next life ...I hope your dreams come true.

you are fortunate to have a support group as close as family...good for you.

Thank you ...I suppose it was fortunate to have family there to show me the way ...and a mindset to accept a girlish path.

I grew up all boy and was punished when I was caught by my mom in my sisters clothes.
My sister caught and punished me for wearing some of her discarded clothes too. Her girlfriend thought it was cute and had me dress up at her house on an off for 4-5 years.
My high-school girlfriend, fiancee & eventual wife (#1) was 100% in favor of my crossdressing. She encouraged me and even outed me to a lingerie store clerk in SF.
We are all unique individuals, but share similar thoughts and emotions none the less. Divorced, I remarried wife #2 20+ years ago. She knows off but does not encourage my crossdressing as a general rule. I still look forward to dressing, in private, when I can.
Take it slow and be patient because you will find your place in this world ...

I can't say my introduction to crossdressing was slow but my mother and sister were patient in bringing me along as one of the girls. Today, at 20, I have accepted who I am and where I am in the world and I have family and friends that support me ...although most only know me as my feminine self.

That's so great...I'm sat dressed in my sisters clothes right now. I honestly wish my mom would take me shopping and buy me some dresses or some sexy underwear to wear around the're so lucky babe xxx

I keep reading your life story and your responses to others and continue to be amazed.

What seems to be to be the most important facet, you like looking at the mirror and what you see. Good for you.

Many of us say we would love to trade places with you. But most of us got to move back and forth beyond boy and girl.

Yes, we would have probably loved our mom saying to us "little girls don't sit like that" and other remarks to reinforce our femininity. But constantly? And when we wanted to go outside to play ball again, that was no longer an option because we were now, all in , a little girl.

You handle what life has presented you with such class and grace.

Yes, I am one of those who would have loved to trade places and to have grown up as you- BUT only if I had your make-up and fortitude so I could emerge as such a confident, wonderful person, you have.

I think I'm blushing ...thank you!

I know that many of us out there did not grow up in the same supportive and loving family and life remains a struggle. I think it was different for me because my mother and sister taught me to accept and appreciate who I am. Although the origins of my feminine life are sometimes in question, (and yes I still occasionly fantasize the "what-ifs" of my life) ...there is no doubt that I have learned to love being the girl I have become.

It's so wonderful for me to know you are finding your true self at such a young age. Remember to follow your heart and never settle for anything short of what you want to achieve! Candice

Thank you Candy. I am only now beginning to realize how exciting ...and frightening it is being in the real adult world. ...Kaylee.

We share alot of the same early years, they were soo much fun and enjoyable

Yes ...there were many good memories of those early years ...although I hope the best are yet to come! : )

I think you probably already know where your heart is leading you, at least in this area of your life. Have you thought of having your sister get you a date with a guy?

It is well past the "thinking" stage Since moving in with my sister earlier this year my eyes have been opened to all sorts of new things. She brought me on to EP which has been a virtual support group for learning how I belong. She also previewed a couple online dating sites for me to began some social interaction. As a result I have met and am dating a beautiful girl ...and at my sister's urging, have gone on dates with 2 young gentlemen (2 cute guys). I have discovered my feelings are drawn more to the person than the gender although I respond with distinctively different emotions when I am with guys or girls. I guess time will tell who I ultimately want to prepare dinner for at night.

I understand completely what you are saying. I am much more comfortable in the company of females, but for me it is not for any sexual reasons. I feel I relate better to females because our likes and interests are the same. The things I like to talk about are the same generally as what females want to talk about. However, for me, I am sexually drawn to men. I love the strength of real men and how they make me feel on the inside. Oh, and I love their genitals as well. ;)

What a touching story! i'm a crossdresser too I'm 55 i started crossdressing as a teenager i never knew my Birth mother or father maybe that has somethinto do with it! i did'nt crossdress again until i turned 53! i'm married with 2 adult children! i never thougt i would be crossdressing again at my age! Now it seems i am addicted! i hope things work out ok for you! love u kayleew 2000

Thank you for your comment and I am sorry that you missed out on what could have been a lifetime of wonderful memories. I am happy to be chasing my rainbow now.

i trully am connected to you... i am a 49 year old man that has been a girl in private since my mom and my aunt started dressing me as a girl when i was 2 or 3... i was raised in an all girl house 2 sisters and 3 cousins. my earlyest memories are of half naked girls and panties... they kept me in diapers and ruffled plastic panties till i was 12. breast fed from my mother and aunt til 10

IYou are probably right. I'll bet we shared many of the same emotions growing up ...from excitement to embarrassment, from happiness to apprehension and back again. I am just now living away from home with so many choices to make in my life ...but I just can't get myself to add any boy's clothes to my closet full of skirts and dresses.

I wish I had a mother that would have done that for me you are very lucky

Thank you. I remember being one of the girls around the house was a comfortable fit for me after some normal boyish resistance. There were other times when I was about 14 or so that I dreamed about being a boy again ...probably about the time I felt some attraction to other girls. My Mother and sister encouraged me through those times and today I am just happy to be me.

Hi Kay, great story! I can certainly related to being embarrassed and at the same time thrilled about going out. The first time I went out to the mall (by myself), I was terrified, but as normal teen I just hung out at the food court and window shopped. After a while, I didn't notice that I was going from store to store...and even started conversing with other people. Somewhere along the way, you feel comfortable in girls clothes and it becomes so natural. Please write more...I would love to hear about your experiences.

Thank you for your comments. In the early years my mother would always take sis and me to the mall shopping. That must be why i love to go shopping even today. But still, I find embarrassment and excitement closely woven in my heart two sides of the same girlish coin.

My mom was a single mom also. Lived with her and my sister. My mom put me in a pink wallpapered room. With womans clothes in my closet and drawers. That she stored in there. I would tell her all the time to move it and give me my space but she would not do it. So i started to lock my door alot and try it all on. Then even started to go up stairs to her room for more fashions she had stored. Its a small world really.

Isn't it amazing what a cute skirt and a pair of panties can do to a little boy's heart. Do you think your mom put those clothes in your room hoping you would try them on?

Thats a good question kaylee. After my parents divorce i feel my mom was upset with men in general. She could of put my sister in there lol. There were drawers of everything that a woman would use. Makeup of all sorts on the dressers top. She keep me in there for 2 years. I begged her to move it all alot. She would not though. I was only 10. I am okay that she did though. I felt wonderful from doing it. Nothing sexual at all. Just very girly. It gave me a peace. Cant really explain it. I am not gay or bi at all. I feel i need a woman in the future to help me with it all. I feel there is more to it than sexual feelings by far. She did move it after 2 years but keep me in the room still. She must of wanted her stuff back. I feel she feminized me with out the pressure of making me or telling me. By giving me a choice.

I totally understand what you are saying. Particularly in my younger years, being my mother's daughter gave me a sense of peace and belonging. Now, at 20, I still find my attention drawn to pretty girls so I probably was never genetically inclined to be feminine was more of a learned process. However, I can't deny after so many years in skirts, that I appreciate when a cute boy looks my way.

Thankyou kaylee:) I am still learning. I have a peace now. I have a chance to be very happy as a girl now. I feel so much better. I am a natural sissy girly. So the clothes just bring it out more. I am very shy and quiet. If i went out dressed i would prob. Start to notice guys more. I am not sure on my sexuality completely. I just know that i am happy being a girl:)

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Fabulous story that reminds me so much of my own development.<br />
Hugs<br />

Thank you Sammi, From the stories i read, i think we have walked a similar path in heels once or twice. :)

I added you hon. I ask these questions just to help you really, not to pry. If you feel a B cup I would say you have been on estrogen at some point. What are your measurements?

Last night laying in bed, i thought about it. Oh I am sure somewhere around 16 or 17 that i realized I must have been on something but really didn't have anyone to talk to about it other than my mother or sister. I specifically don't remember asking her about it but then maybe it just seemed more normal at the time that we all looked and acted like girls. Assuming you are right, I still like who I am and I am not sure I could handle or even want a drastic change at this time in my life..

I think you have your answer dear. You look like a girl, feel like a girl, are happy as a girl. So next step go on a date with a guy and see how you feel about men.

That's what my sister says too. Perhaps ...if the right one comes along...

As a 40 year old life long crossdresser my advice is relax a little. I have been married to my wife for 16 years. You are young and have plenty of time to figure out your likes and dislikes. I doubt you were ever on hormones. I never was and have always preferred girlie stuff. I would always rather be in female clothes than in male clothes. To bad society doesn't allow for that.

Thank you for your thoughts, Sissy. I think at a dna level, I can always appreciate a pretty girl walking by and maybe someday I will find the right woman like you seem to have done. On the other hand, having dressed as a girl from such a young age, I have learned to appreciate the attention from a cute guy. I may have to take a step or two down both paths to see where my heart will lead me.

One question no has seemed to ask on your other stories. Did your mom give you hormones? Did you develop like a girl, you know, curves, hips, breasts? If so, that puts a different spin on things. One you may be sterile if you have been on hormones for any length of time over a year. Two the hormones may have influenced your brain in ways that would make it difficult to being a guy again. No impossible mind you, but difficult. Try and figure it out now while you are young waiting to you are older is so, so much harder!

We haven't talked directly, but you have posed one of the more difficult question for me to answer. The honest answer is that I don't know for sure if i had ever taken hormones at an early age because it was never discussed. Of course, when you are 9 or 10 or12 or 13, you don't really know about such things. I have always been quite thin and small was my real mother and father and i didn't show any growth in my hips or such. On the other hand, yes, both my sister and I were on vitamins and herbal supplements for our teen years. Perhaps out of force of habit I still take them today. I don't know if I am being naive but I don't believe i was on an estrogen therapy because I am still quite thin. Of course I would like to think I don't have brain problems like you mentioned, at least no one has put that idea to me quite like that ...although i do have certain views towards both pretty women and, on occassion, cute guys. Hasn't everyone? right? I am only 20 and I have lead a pretty sheltered life so i never have have had a chance to experiment with my feeling like most kids. So what could i tell you without going to the doctor and reporting things that i maybe might not want to hear? Here is one I guess I have learned to face with mixed feelings ...I am currently wearing a very cute little pastel blue bra with scalloped lace trim ...and presently, it doesn't need any padding whatsoever to fill out its B cup. Please don't hold that against me.

I think it would be nice if you and I could be friends. What do you think?