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My Sister Taught Me To Crossdress ...my 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.
Posted by kayleew2000 at 5:37PM on Mar 27th, 2012
33 comments | 45 recommendations
I Am a Crossdresser (Mobile)
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Recent Comments
Lovely story. I wish I had an "aunt" as nice as your mom.
Posted by priebecl on Apr 20th, 2015 at 6:10PM | 0 recommendations
Love this. Lucky girl.
Posted by GinaYorktown on Dec 8th, 2014 at 2:28PM | 0 recommendations
You had a wonderful start to your dressing! A family who loves you! They are pure gold the both of them!
Posted by foronenightonly on Oct 6th, 2014 at 2:42AM | 0 recommendations
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
Posted by Ddsmen on Sep 21st, 2014 at 2:53AM | 1 recommendation
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
Posted by sissyjolene on Aug 19th, 2014 at 3:35AM | 1 recommendation
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.
Posted by like2cd on Aug 11th, 2014 at 8:49AM | 1 recommendation
cute story!
Posted by tvCorinne on Jun 8th, 2014 at 9:35AM | 1 recommendation
I wish my mother would have encouraged my femininity when I was young. It would have been so helpful.
Posted by rwtopv on Dec 8th, 2013 at 3:10PM | 2 recommendations
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
Posted by BertaCD on Sep 23rd, 2013 at 1:29AM | 5 recommendations
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.
Posted by luvtheestrogen on Sep 5th, 2013 at 3:16PM | 2 recommendations
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.
Posted by luvtheestrogen on Sep 4th, 2013 at 10:02AM | 3 recommendations
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.
Posted by VelvetKay77 on Aug 9th, 2013 at 9:50AM | 5 recommendations
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!
Posted by iluvsatinpanties2 on Jul 11th, 2013 at 10:50AM | 3 recommendations
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.
Posted by thecarer on Jun 15th, 2013 at 2:12PM | 2 recommendations
would like to be your daddy and have a family like yours
Posted by dad4sissybabe on Jun 15th, 2013 at 1:41PM | 2 recommendations
Since you feel so comfortable in all sorts of girlish attire do you have your ears piercedr How did you feel when they were piercedr If your ears are not pierced, have you ever thought about gettting them piercedr 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.
Posted by Guywearingearrings on Feb 14th, 2013 at 1:35PM | 7 recommendations
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
Posted by radhaparag on Jan 24th, 2013 at 7:26PM | 3 recommendations
you are fortunate to have a support group as close as family...good for you.
Posted by tempestcd on Jan 21st, 2013 at 9:00PM | 2 recommendations
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 ...
Posted by SDC92374 on Jan 21st, 2013 at 6:16PM | 2 recommendations
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 house...you're so lucky babe xxx
Posted by Lushgurl21 on Nov 19th, 2012 at 7:24PM | 4 recommendations
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 constantlyr 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, ....like you have.
Posted by Kim1girl on Nov 19th, 2012 at 7:35AM | 4 recommendations
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
Posted by Candicegirl on Oct 28th, 2012 at 3:31PM | 2 recommendations
We share alot of the same early years, they were soo much fun and enjoyable Michelle
Posted by dressedyung on Oct 18th, 2012 at 10:11PM | 2 recommendations
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 guyr
Posted by AndiSissy on Oct 18th, 2012 at 8:19PM | 2 recommendations
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
Posted by crossdress55 on Oct 18th, 2012 at 6:29PM | 3 recommendations
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
Posted by lilgrl164 on Jun 2nd, 2012 at 8:52PM | 1 recommendation
I wish I had a mother that would have done that for me you are very lucky
Posted by della23 on May 13th, 2012 at 3:51PM | 3 recommendations
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.
Posted by PinkISpunk on Apr 6th, 2012 at 12:42PM | 2 recommendations
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.
Posted by Girlyfashion on Mar 31st, 2012 at 2:13PM | 4 recommendations
Fabulous story that reminds me so much of my own development. Hugs Sammi
Posted by sammi11 on Mar 29th, 2012 at 8:05AM | 2 recommendations
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 measurementsr
Posted by Ellefem on Mar 29th, 2012 at 7:30AM | 1 recommendation
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.
Posted by Sissy4her on Mar 28th, 2012 at 11:56PM | 2 recommendations
One question no has seemed to ask on your other stories. Did your mom give you hormonesr Did you develop like a girl, you know, curves, hips, breastsr 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!
Posted by Ellefem on Mar 28th, 2012 at 10:00PM | 1 recommendation
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