A cross-dresser’s story – Getting to know Rachael

If this is your first time reading about Rachael, please refer to her first installment to learn more about her – A cross-dresser’s story – The beginning

I have kept the existence of Rachael from my family members, especially my children although it is fair to say that many of the younger people today tend to shrug such things off with a casual ‘OK.’


However, my long-time girlfriend (we have been together for over 6 years), does know about her and although she has bought me items from stockings, shoes and dresses, she wants nothing to do with her.

She found out about 4 years ago, when I had inadvertently left some of my photos on my laptop and she was looking through it for photos of her Grandson.  Whilst I had deleted them from the main library, I had forgotten to do so from the recycle bin.  I received a rather terse text from her whilst I was at work saying ‘We Have to Talk!’  Don’t ask me how but I knew instantly that I had been rumbled and the following hours at work were filled with dread.


Ultimately, after we had retired to bed that evening she dragged it out of me that I was a cross-dresser and I thought that would be the end of our relationship.  It hasn’t been but I cannot ever see her fully accepting Rachael.

I completely accept that it must be incredibly difficult for a woman to find out that her other half likes to get all dressed up in feminine clothing and make-up and present himself as a female, and then be expected to accept it as the norm.

Although my girlfriend would probably not acknowledge it, because of my love of all things feminine, I have helped her choose dresses, coats and other clothing which have been more suited to her than other items she has been looking at.  And a previous girlfriend always appreciated me being with her when shopping for clothes, as she put it ‘You have an eye for what suits me.’


I have never been able to explain to my girlfriend in concise terms why it is I love presenting as Rachael, hell, I don’t even know why!  I just know I NEED to as I previously mentioned.

Personally, I dislike the term ‘Tranny’ when others refer to CD’s even though it is shortened from Transvestite.  But that term refers to anyone who wears clothing meant for the opposite gender.  Women wear trousers/pants and jeans, all items originally designed for males but no one calls a woman so dressed, a Tranny!

I guess that because I have kept Rachael well under the radar I have never experienced name calling or physical attacks and am thankful for that as so many CD’s and TGirls have suffered badly, even to the point of suicide.


Another question I would expect to be asked is ‘Are you planning to go for realignment surgery?’  Answer, No.

Even though I adore being fully feminised, I have no desire to be a woman.  I don’t think I could cope being 24/7.  But I do respect completely, those people who suffer the trauma of being ‘In the wrong body.’  And trauma it must be as so many seem to take their own lives after struggling for years with their place in society.

To me, as more and more people transition from female to male, and of course vice versa, it is simply a sign that humans are continuing to evolve.  Embrace this evolution.


6 thoughts on “A cross-dresser’s story – Getting to know Rachael

  1. Its your story but it echoes so many others, me included. I just wish I had your freedom I am truly closeted and will have to remain so. Any mention of people Dessing the “Wrong” way causes a load retort.
    Best wishes Riat nee Richard

  2. I also have kept my dressing secret from my family. Wife has known for years and now we have told our child who identifies as non-binary. Their reaction was pretty much the same as you said for younger people, “Cool” was their answer.

  3. Thank you Rachael for your blog on your journey re who you are. I am much like you; a 62 year old Male who has felt much the same need as yourself. I also am very hetero and have absolutely no Bi interests or tendencies, nor any desire for ‘reassignment’ surgery whatsoever. However, ever since I was around 10 years of age there has been the awareness that there was a small part of me that was Feminine.

    As the years passed I found that feeling grow more and more insistent and eventually became impossible and I now firmly believe, unhealthy to try to suppress.

    There was still always feelings of unease and embarrassment but reading your blog has, for the first time in my life, totally dispelled those notions and I am now totally at ease with this trait in my character. Like you, I need to do this!

    I have over the last few years assembled a modestly sized Feminine wardrobe but as you mentioned, they are not Female as such, they are mine! I fully intend to increase this wardrobe in due course.

    Regrettably I will never ever be able to look as fantastic as you! I wish I could but then again, it’s nice to dream!

    (On behalf of Johannah)

  4. Ahh yes our conundrum of a 55+ Crossdresser. I to have cross dressed forever. My wife tolerates it, used to participate some but not so much now. We did go to a transformation service for New Years and it was fun, but not exciting. There was more excitement in the anticipation. For me most of the time there is a sexual component to it. I think for most there is. I would love a friend to really talk to about it. But, as many I remain closeted. I have put on weight so I no longer look as good, but it still is a major part of me that I have long since stopped “purging” or getting wrapped up (Getting my panties in a knot! Ha) about. Hope you all have fun dressing. Steph

  5. Pingback: A cross-dresser’s story – Rachael’s wardrobe | The Nylon Swish

  6. I have enjoyed reading your blogs. You have some great outfits , and look good. I do prefer the longer lighter colour hair on you , suits you colouring better , well I think so .
    Keep up the good work and I look forward to reading more from you .

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