Tiffany arrived only a couple short months ago (2/21). It has been short and sweet so far. Discovering Crossdresser Heaven accelerated her evolution. Thank you Girls.

The beginning.

It’s not your typical start, as my thoughts and feelings did not come to the surface until late in life. But there was one instance as a child that I experienced dressing as a woman. It was a school Halloween party when I was 8 or 9 years old. Two friends and I thought it would be neat to go as women. Our mothers said it was all right and the three of us went dressed. The costume consisted of a wig (they were the thing back in the day), shoes, hat, maybe a bra, not sure and her coat. That was it.

The only thing that came close for me to be interested in women’s underwear was paging through the Monkey Wards, JC Penny’s and Sears catalog in the bras section. I was infatuated about that. Too young at the time to do anything about it, if you get my drift. I had opportunities to rummage through my mom’s drawers and never had the urge to try on her underwear or wear her bra again. For me it was ‘yuck’.

Years later.

The years went by with no desire to wear women’s underwear. Not even my wife’s. Then in the summer of 2019 everything changed. My wife went to see her mother and spent the summer with her. That meant I had five months being a bachelor. Believe me I was in heaven. Watch TV with just a shirt and shorts going commando, ah the freedom.

For years I struggled with men’s underwear. I could not get any two out of a pack of six to fit comfortably or the same. That was crazy and frustrating to pay for a pack of underwear and only have a couple to keep, then throw the rest away. The frustration built and with my wife gone for the summer I came across a blog or a comment basically stating ‘try women’s panties’. I thought well I have nothing to lose. So on-line I went and looked at size charts and took my best shot on the size. When I got them and put them on it was wonderful. There is nothing like it. I went conservative with color and style, gray plain hi-cut. And what are panties without a bra. Again on-line I went and looked at bras, sizes, styles, pocketed, T-shirt and strapless. I had some time to get the ones that fit and then I needed breast forms. I bought a couple different sizes and wore them at home and at night. The bras and forms were not mentioned to my wife until the beginning of this year. That part of the story is further down the article. At the end of the summer I went and picked up my wife. I had a couple pairs of panties with me but went in men’s just encase my wife thought I was crazy. As it turned out, she said ‘if it works for you, not a problem’. So off went the men’s undies and on went the panties. So it was an innocent and legitimate reason to wear panties. After some time had passed the same old color and style was getting boring. It was time to expand my collection. That meant the pink, white and white with patterns were introduced. I just love the pink ones.

January 2021.

My birthday was approaching so we went out for dinner. During dinner I said I had a surprise for her when we got home. I explained to her that I looked into this (the surprise). We arrived home and told her wait one minute. I entered the bedroom wearing a cheap bra that I ordered then explained that I like to wear them. The discussion went well and I didn’t sense any withdraw or bad vibes. At this point it was just under dressing. So the days and weeks rolled along and that’s when I joined FetLife and found a group called ‘Guys who like to wear bras’. My time was spent there participating in the discussions. It was determined that this is ok, nothing wrong with it and conveyed it to my wife to re-enforce that this is something guys like to do. While on the sight I saw quite a few CDers and thought Hmmm. It was time for some more education and looked up Cross Dressing and what it was about. That peaked my curiosity and that started the journey down the road to Cross Dressing. With a few more discussions with my wife it began.

It was only February when I started buying clothes on-line. After a few items it was time to look for wigs, shoes and makeup. My wife has some makeup so we looked through what she has and went to a couple stores to fill in what I was missing. With everything needed it was time to put it all together. Not knowing how to apply makeup to a male face the very first attempt was utter failure. YouTube became a big help about makeup application.

Exceptional Voice

In the meantime, my wife asked me what my name was. I had not thought about it much. But realized I needed a name. Tiffany was a name I just liked. Smith comes from an Angle. (I’ll let you figure that one out). So there you have it, Tiffany Smith was created and has only seen the world before her for a couple of months.

  • When you first told your wife you were a cross dresser, was she 1) Very accepting, 2) Accepting with limitations, or 3) Not accepting at all.
  • About how old were you when you first became a cross dresser?
  • Are you more into dresses, tops and jeans or slacks, or skirts and tops?

Thank you girls for reading my article. Please take the time to either respond to my article or answer one or more of the above questions I’ve posed to you.

Love all you Girls,



More Articles by Tiffany Smith

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    Bettylou Cox
    Active Member
    25 days ago

    Hi Tiffany, And thanks for posting your story. Your timeline is similar to mine, except that I became a “real”CD at a much later age (80), after suppressing Bettylou all of my adult life. I played “dress up” with playmates around age 9, and Dressed briefly around age 15; then only a few isolated incidents until the Pink Fog found me buying ladies’ jeans and tees a few years ago. I was alone and deep in the closet until I found CDH, exactly 2 years ago. Then, Bettylou developed rapidly; I came out to my wife, began buying shoes, clothes… Read more »

    Sandy Jayson
    Active Member
    24 days ago

    Hi Tiffany Loved your story, hope all keeps going well between you and your SO. For me when my X found out the first thing she did was to tell our 3 grown kids and then threatened to tell my 4 brothers. So I ended telling my brothers myself and so far all has gone well. I have been dressing of and on for all my life. But back about 1980 I got very heavy into CD, with nothing like CDH to help me I quit after a couple years. Go to March of 2019 and something came over me… Read more »

    Robin Snow
    22 days ago

    Hi Tiffany, While I’ve always known about my feminine side for my entire life, I choose to ignore her. By the time I hit my mid 50’s and 20 years into my marriage the woman within me wanted out. In order not to go crazy, I decided to accept her into my life. I immediately told my wife. I can’t say she was thrilled with the idea. While she accepts this side of me she certainly doesn’t do anything to encourage it. To keep things good with the wife, I limit my dressing to jeans, leggings, shorts and of course… Read more »

    Carolyn Kay
    Active Member
    15 days ago

    Halloween parties have jumped started a lot of us. I was about 16 when I went to one dressed as a girl. I was a big hit at the party, I felt so comfortable. I didn’t understand it it back then but all I knew is that it was somehow me. Now I have a closet full of women’s clothing and an understanding wife. She does not embrace who I am but has told me she knows it is part of who I am. Carolyn

    Carolyn Kay
    Active Member
    14 days ago
    Reply to  Tiffany Smith

    That is my closet pictured as a backdrop on my profile page, please note, that is just a small part, lol.

    Would love your thoughts, please comment.x
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