An open letter to my sister

I don’t know quite know how to begin this: there is so much that I want to say that the rods are jumbled in my mind. Let me start with the most important three words; “I love you!”. All the rest pale in comparison to those words. There are other important things I want to say but those three words encapsulate the others.

I have been living with my gender issues alone for so long and had kept them a secret for fear of people’s reactions. Society has just about gotten used to the gay movement becoming-if not ACCEPTING in all cases at least TOLERANT of it. While there are still pockets of people who are violent in their opposition to them, for the most part people take a live and let live attitude.
Such is NOT the case for those who are transgendered in one form or another. I use the term transgendered here to include the entire TG continuum-from heterosexual crossdresser to the transgenderist living and presenting part or full time as female but without HRT or surgery, and finally to those who partially or fully transition to female. (For the sake of simplicity, I am dealing only with males who have varying degrees of femininity in their lives.). Society does NOT truly accept or even tolerate those who don’t fit into the neat matching boxes of male and female for their sex, gender, and gender identity. There are signs that this is oh so slowly beginning to change particularly among the younger generations (though even some older folks are becoming more tolerant too)!

It is with that background that I felt like I needed to keep this part of me hidden from the world in general and from my family and friends in particular. I have not completely figured out where I lie on the TG continuum. I began as a crossdresser (hereafter CD) at age 11 trying on my sisters’ clothes. AS with many CDs, there was a fair amount of arousal and release involved but there was also a sense of comfort and normalcy when dressed. While I liked sports, I was never a “macho” type guy-I had none of the stereotypical teen guy desires to do stupid stunts to prove myself to other guys, or to look at naked pics of girls (or guys for that matter). I always thought of myself as more feminine in nature wanting to be in the female submissive role in a relationship. I named this part of me Cynthia after the name you and my other sisters gave me when you dressed me up around ages 4-6 and called me your little sister. I have no conscious memory of this earlier dressing whatsoever.

These dressing episodes continued in private through my high school and college years in varying frequency. I also did extensive research into crossdressing/transvestism, and transsexuals (TS) in the public library (there was no internet at that time!) Again at that time I thought I was a CD as I thought that I had little to no desires to actually change sexes (and this was further confirmed in my mind because of the arousal aspects which I thought meant that I couldn’t be TS because I had heard they typically do NOT feel the arousal aspects while dressing-just a feeling of normality and naturalness in dressing as a female. When I had first dressed up I was caught by Dad and he asked if I wanted to be a girl. I told him no (and wonder to this day what might have happened if I said yes!) that I just wondered what it felt like to wear a dress.

After graduating, I was working in restaurants when I met the woman whom I would marry. Since I was so shy, (and craved the feminine role) it was SHE who asked ME out. Long story short, we were married about 7 months later. I did NOT tell her about Cynthia because, like many if not most CD/TG folks I thought that the feelings would dissipate and disappear now that I had a “real” woman in my life. Obviously, as most of us know, this is NOT how things happen. The desires-stifled and forced underground by societal expectations-smoldered slowly waiting for the fuel to flow and bring new life to them. This happened in the form of massive stress in my life when I lost my job a month before my daughter was born. As dressing had always been a stress reliever for me in the past, I began to dress in my wife’s clothes and even bought myself some makeup, a pair of heels and a Halloween women’s wig. She caught me, almost left me, but stayed after I begged her not to leave and we remained married for another 12 years til she finally decided she could not live with my issues any longer.

So after we separated I moved to Mother’s house and have been there ever since. I did eventually tell another sister and Mother about my CD feelings and then told my then 15/16 yr old kids as well. They were all at least tolerant though none of them really wanted to see it at all. (kind of my own version of “don’t ask/don’t tell). I did NOT tell them of my TG feelings which were by now growing stronger Or perhaps better said I was beginning to acknowledge them somewhat instead of denying them to myself as I had done for decades of my life. My female wardrobe expanded dramatically and I continued to dress in the privacy of my bedroom many nights (probably at least 35-50% of the time at home in the evenings after work spent dressed).

After Mother died and I bought the house, we were dealing with the distribution of the stuff and I was constantly worried about folks finding Cynthia’s trousseau. I continued to dress as often as possible but had to worry about folks dropping by unexpectedly when I would have to get undressed in a panic-throwing things into a closet or cabinet and scrubbing off my makeup! Finally all that was done and the kids were on their own and I began to let Cynthia’s stuff continue to grow and spread out within the house. I STILL couldn’t be open about it because we had family events and folks still treated the house as if it were my parents’ home not mine-which while understandable –made it difficult/impossible to make the place Cynthia’s home as well as Kevin’s.

This past summer I found the online community at Crossdresserheaven.com (CDH). Here was a place I could open up about my feelings without fear of rejection or ridicule. I became more and more active in the community and began to acknowledge that the feminine feelings I had would not be satisfied with Cynthia remaining furtively at home dressing only occasionally. I began to dress almost every night after work and even went out driving while dressed several times (but I’ll let you read those stories elsewhere).
So now we get to what I am writing for you here. I knew the moment would come when others would need to learn about Cynthia especially if she were going to come out into the light and at the LEAST be out in public. The story of the first person I admitted it to (your daughter-and by extension her husband and a few of her closest friends) and then my friend from pool (a female friend and by extension her boyfriend who is also my friend too) are written elsewhere as well so I won’t repeat them here. It was easier to share with your daughter and my pool friend because I was fairly certain they would both be receptive and accepting about it right away and that was indeed the case. Far less certain was how the rest of the family would react (sisters and my kids (and their SOs) and nieces and nephews) and especially you.

I say that not to be mean or critical but because you had (in the past) made several comments about transgender people and the lifestyle that came across as disparaging and almost transphobic. I am not saying you MEANT them to come across that way but that is how they felt. It really hurt at times to hear you and my other sister and her son talking about how only what you were born with between your legs determined if you were male or female and that anyone who had TG feelings/issues were pretty much sick or mentally ill in some way. (that they would be lurking in the women’s room like predators.) Each comment was like a little stab to my heart as I wondered what you would think if you only knew that your own sibling was one of the people you were talking about. I was so afraid that once you discovered the truth about me that you would hate me and want me gone from your life as an abomination. It was for those reasons that I didn’t confide my secret life to you.
So it was with some trepidation and skepticism that I heard the news from my nephew-in-law last week that you had pondered it out while talking with your daughter that I was (and am) trans and had ended up being not only tolerant but accepting of me. And so when I called/texted you on Monday about coming over to talk, I was still prepared mentally to hear that after thinking more about it that you were NOT really OK with me and would still not want anything to do with me. When I asked if you wanted to see me dressed, you said “sure why not?” so I nervously got myself ready and then answered the door when you rang. You looked a bit shocked and surprised but then you embraced me and kissed hello and told me I looked great! Years of fear and doubt fell off like shackles being released at the end of a long prison sentence. That evening was WONDERFUL as we sat and had a conversation and looked at my pics and we discussed the whole situation. All the while, I felt comfortable and natural in my bra and breastforms, undies and heels, full makeup and wig. This was Cynthia’s first long term exposure to someone else in person and she was delighted at how it went and how she felt! That was entirely due to the absolute and total love and acceptance you gave me despite what likely seemed to be cognitive dissonance at seeing me your brother appearing as a woman-the girl who had been hiding inside Kevin for lo these many decades.

I am still trying to figure out where my life journey is leading. I know I do NOT want Cynthia to be confined to furtive solitary evenings at home. She needs and deserves the opportunity to let her light shine in the world as she gets out and interacts with others. Now whether being out dressed is enough to make me happy and satisfied with life or whether I have indeed been denying my TG feelings and need to begin my journey toward living part or full time as female-(with or without hormone replacement therapy and/or sexual res-assignment surgery(SRS)), only time will tell. I plan to try and get Cynthia out into the world this year to see how comfortable I am with being out as her. If I AM comfortable then I will have to examine my next steps.

Most importantly I know now that no matter what my path, I will always have your love and acceptance and nothing that happens can take that away. That realization too made me weep with joy as I move forward in the rest of my life. Thank you for loving me as the sister you never realized you had! I cherish our relationship and look forward to it deepening even more as I discover who I truly am. It just goes to show that love is indeed stronger than prejudice or hate and that family is the most important thing in life! Below is a poem that tries to capture the above narrative.

Love,
Cynthia (Cyn)
PS I can’t wait for you to join the CDH site to meet Cynthia’s friends!

For oh so many years I felt as lonely as could be-
The secret burden weighed me down and drove me to my knee.
The female soul inside of me was screaming to come out
But fear of your reactions filled my heart with so much doubt.

If I revealed that inner girl who hid within the shell
Trapped deep within the manly life-a special kind of Hell;
I risked the loss of everyone who might not understand
Why anyone would give up living as an ordinary man.

They can’t imagine how it feels to be so out of place
To act as though I didn’t care for beauty and for grace.
The girl inside me cringed at times at jokes that she would hear
From boys who laughed and ridiculed and say that she was queer.

As years went by, I learned to hide all signs of who I was-
I had to watch so carefully each action just because
To show the female side of me in any little ways
Could mean a life of solitude for my remaining days

But recently, I came to feel that I could wait no more.
I had to let the girl within to come into the fore.
No longer would she be content to dwell within the night
For she deserved to boldly step into the morning light.

And so she started telling folks about her deepest soul
And slowly oh slowly she was starting to feel whole.
But there were those she feared would not accept this side of her
And so she hesitated opening up to her sister.

But then as fate would have it, you were able to find out
And though my greatest fear had been that you would scream and shout,
Instead you were accepting and embraced me with a kiss
And let me know you didn’t mind your ‘bro’ was now your ‘sis’!

Now whether I transition is a choice to still be made
Or if I stay the way I am- a part time comely maid.
No matter what I know that I won’t walk that pat alone.
My sister will be there with me to make me feel at home.

So thank you sis for loving me no matter who I am
And calling me by name or by the pronoun sir or ma’am!
I am so blessed to have you that my heart still swells with pride
That you ignore the outer shell and love the one inside!

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skippy1965(Cynthia)

The Original Cyn, or OC for short. Cynthia is from Richmond Virginia, she crossdresses every day (lucky gal!) and has a knack for tracking down niggling technical issues so we can fix them. She is also on a journey of self-examination to figure out where her feminine journey will lead her, and is always willing to talk with others about their feelings and questions or her own.

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  1. carrie 9 months ago

    I recently moved in with my sister,she is 7 years younger than me,i m 62 and just couldn’t take hiding any longer,i have been crossdressing since I was 12,an d have always enjoyed being the nughty little girl during my encounters,when I dress I become carrie the little girl and I have found that most people love it,men go nuts and love me role playing as her,well I finally broke down and told my sister all this,to my surprise she doesn’t mind me crossdressing and likes it w,hen I’m in my girl clothes,panties and a short nitey in the living room in the evening she l we areets me wear in front of her,she complaments how I look,helps me get dressed,and she is fine with it,my point is my fears were unfounded and there are some very intimate conversations about my life and my sexual encounter,i have never been so close to her I love sharing with her,we talk about things some would say a sister and brother shouldn’t,that its perverted but I feel we are not hurting any one

  2. Abby Lauren 11 months ago

    Thank you so much, Cynthia, for such an articulate expression of what so many of us have endured for decades in the absence of tolerance and acceptance of our “differentness”.
    I, too, came out to my only sibling, my older sister, and her first words (which I shall never forget) were: “I will always love you as a brother or a sister or both -whichever you would like to be.” We wound up spending lots of time together as 2 sisters going out everywhere and still do.

  3. Rhae 1 year ago

    oh Cyn i can’t stop weeping i do’nt talk to my sister because she is not a nice person she is just mean to everyone. but i told my little brother who happens to be gay and showed him some of my pictures and all he said was sis you needi to dress in clothes that compliment you better and that his husband who does hair and makeup professionly wold help me with my makeup. i am such a lucky gurl. Cyn i love you your articles bring me so nuch peace and joy. peace love and lots of hugs Rhae

  4. Wanda Shirkey 1 year ago

    Cynthia,

    Thank you so much for that. I have been thinking about telling my sister as well. I think she would be supportive. What a touching story. Thank you for sharing.

    Wanda

  5. OMG Cyn, how many more parallels are we going to have! I just came out to my big sister and she is totally cool with it and continues to love her little brother now sister!
    I am soooo happy for you and wish you all my love as a sister on the same journey!
    Xxx

  6. ABCDF 1 year ago

    I am a new crossdressing and I need to be as a member in crossdresThanksser heaven

  7. stacey s 1 year ago

    Cynthia, That was a beautiful letter and thank you for posting it.
    Hope other family members and friends will appreciate it.
    Love & Hugs,
    Stacey S

  8. So happy for you..I always have you in my thoughts, and hope you find your true path really soon! Please tell your sister she is a wonderful, loving ladie that I respect and admire!

  9. Jenna 1 year ago

    Nice to see you have your sister to share your true self with now. I have thought about telling my sister about my crossdressing , but I hesitate to expose such an intimate part of myself to her without knowing how she might react. I have told my fiance about it and she is totally supportive. We even share clothes! I hope someday to be able to come out to my sister. I applaud your courage!

    • Author
      skippy1965(Cynthia) 1 year ago

      Jenna,
      I hope you are able to as well. Family is SO important and she might really enjoy having another sister!(even if only part time!)

  10. Heather Song 1 year ago

    Cynthia, glad you have a supportive sister. Thank you for sharing your story.

    • Author
      skippy1965(Cynthia) 1 year ago

      Thank YOU for the kind comments Heather. I have enjoyed reading some of your posts too!

  11. JamieLeeChainz 1 year ago

    Wow very empowering Cyn and touching the tears where rolling half way through.

    • Author
      skippy1965(Cynthia) 1 year ago

      Aww I didn’t mean to make you cry! 🙂 but thank you so much for the kind words. It just goes to show that our fears are often far greater than the reality that occurs!

  12. JaneS 1 year ago

    I just love jumbled rods. 😉

    Great letter Cyn and I’m glad things worked out well between you and your sister.

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