Bren in the beginning

Hi everyone!! My name is Bren. I want to introduce myself and share my crossdressing story.

My journey began at age five, 53 years ago. My best friend was the girl who lived next door. We played together all the time and I would wear her ruffled black dress in our backyards. We planned to get married when we grew up; she wanted to be the groom and I would be the bride. (How I wish she was in my life now!).

As I entered into puberty, I did a lot of experimenting with my mom’s clothes and makeup. I loved the way silky lingerie felt against my skin. Around 13 or 14, I’d already acquired my own pantyhose, high heels, bra, and a 2 piece outfit—skirt and halter top. I began practicing with makeup, but never mastered it to look good. I would go to the local park and dress up in the woods where I would walk around outdoors, and it felt great! It was so exciting and free.

Slowly, I gathered my courage and began walking closer to the road where I could be seen. I was very skinny, about 130 pounds and had very long blond, thick curly hair. I’m sure I didn’t look like a girl up close, but I loved doing it. Once, an older man approached me and propositioned me. I admit, I considered it, but declined.

One night, while my parents went to dinner, I went all out and got dolled up and sat watching TV in the living room, where I ended up falling asleep. The next thing I knew, my folks came walking through the door and freaked out. They made me sit at the kitchen table in my dress, heels and make up while they screamed at me. My older brother and sister listened. My Dad, he was a he man, beer drinking, bar fighting Construction worker. He called me a fag, and that he wasn’t raising me as his daughter. The banter went on for what seemed like hours.

I was so humiliated; I began thinking something was wrong with me. I cried for hours. They made me go see a shrink, who also said that something must be wrong with my chemistry. I hated him and finally refused to go anymore, telling my parents I was cured. But I wasn’t. I learned to hide my secret better.

When I was 23, I told my live-in girlfriend my secret. I wanted so badly to let my inner female out and share it with someone. At first she objected, but I used my dressing up as a way to spice up our sex life. Soon we were dress shopping together, and she planned her weekend dates with Brenda. We loved garter belts, stockings, and lacy bras. We’d wear matching Victoria Secret lingerie to work. It was a great time in my life, but eventually we broke up.

I went through a short period of time were I began to think I might be gay. Brenda “dated” a couple guys. It was fun, but I found out that I am truly attracted to woman. My next live-in girlfriend found out my secret right away. I took the same approach with her, explaining that it would spice up our sex life. My biggest mistake was in allowing her to film me dressed with no makeup or wig. A couple years later, after we split, she showed the film to everyone we knew out of spite.

Once again, I was humiliated, feeling as low as low as one could go. You must understand, I lived at a time when crossdressers were considered to be sexual perverts, something weird that was not acceptable. This is what I’d been told that by my parents and the shrink. We had no internet, no Jenner, no outlet to express who we really were. Although there’s still a lot of stigma attached in being a crossdresser, things are so much better now. Thank God for this website!!

I stuck Brenda in a closet for the past 23 years, but she’s knocking loudly on the door, wanting to get out and express herself. I’ll be back to share more of more story; thanks for reading!

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Bren Whyme

I am a 58 year old Crossdresser who has not actively dressed in 23 years. I thought I had overcome this desire by locking up my femme self in the deepest recesses of my soul. For some reason she's knocking on the door demanding to be set free, again. She overwhelms me, I loved her like no other woman but she also brought me pain and humiliation. Has my self confidence developed enough over the years to embrace her? Only time will tell...

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Glenda BingyiChrissie CrossErin Hastings*skippy1965(Cynthia)April (Pacific Princess) Recent comment authors
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Glenda Bingyi

Hi Bren it was lovely to read your story adn in certain parts we could swap Bren for Glenda and it would read my life story as well. Like you I had a massive hiatus where Glenda was denied for a long time but she is here and a part of me so I have to acknowledge her. My SO has found me out in the past and like you I have told her it was all a phase and past history but and some will think me evil but I live Glenda when ever I can sometimes in private… Read more »

Chrissie Cross

Hi Bren and thank you for sharing your story. Mine isnt exactly the same, but it rhymes! I hope to submit it for publication soon and I hope you will give it a read.
All the best,

Erin Hastings

Thank you Bren, I am so sorry about your pain. I cant imagine a video outing at the hands of a vindictive soul. I am almost 50. Been dressing since I was 9. Started on a dare from an older sister. Little boys dont turn down dares. I too have had periods of neglecting my sexy side. About 5 yrs ago I went thru some personal trials (divorce). Found myself wearing my girlfriends things when she was working. Then I discovered internet shopping! Oh boy! Or girl. I have a huge wardrobe now. Way more female clothes than male. My… Read more »


Bren-thanks for sharing your story. I’m a few years behind you (I’ll b 54 soon) but still remember those pre-internet days well to. My parents weren’t abusive when they discoverd me but could tell it wasn’t something they were happy about. Cyn went underground and (I thought/hoped) disappeared when I got married but it was less than a year before my wife caught me dressed. She almost left but stayed after I begged and promised to stop. Didn’t happen of course so after holding the marriage together for another 12 years we split. Cyn took a bit to come out… Read more »

April (Pacific Princess)

Bren – I can so relate. I suppressed my crossdressing for over 30 years, from my mid 20s until my late 50s. I’m 61 now and have been dressing again for the past 2-1/2 years. It has been a blessing to finally be able to be myself. I don’t dress all the time, but it is nice to be able to dress when the urge is there. My wife is understanding to a point, and for that I am grateful, but it would be nice to have a partner that wants to be a part of April’s life. I hope… Read more »

Micah Dean

Touching story Bren. I am of your era and have found myself dressing more and and more of late. Agreed, it is an inner struggle to understand your own sexuality. I ask myself as you do l, am I gay or straight, but I see my wife and how beautiful women are and know I am heterosexual. I helped my wife a lot today pick out some new make up today. Little does she know I work on my own technique through her trials and tribulations. In any event the world has changed since we we were young. You were… Read more »


Yes, many elements of your story resonate with my own memories. I hope you’ll soon be able to get dolled up and proudly join other CD’s and Trans women for an event, even if it’s just an informal Girls Night Out. It’s so important to have the support of other gurls. God luck sweet Bren!

Rochelle Mooney

I Love your story, it is all so familiar. Hugs Rochelle.

Lucinda Hawkns

hello Bren, thanks for sharing your journey. sorry to hear all the dis appointments in this journey. yes back then x dressing was not allowed, or never heard of. but know we see it on T.V. the internet{ thank God got the internet } society is not willing to accept the x dressing for some reason. but we hear about woman getting married to woman and men marring men, we see it on T.V men wearing female cloths, men are gay, { i hate that word } but we see it on a daily basis. woman wearing men clothing and… Read more »

fiona moss

Oh Bren, nice story. You sure have had your ups and downs, but you have fought through it all. Dressing femme is a thing which never goes away, sure, some people can supress it for a while, but the desires keep coming back and why shouldn’t they? they are part of you, after all. It was rather unfortunate falling asleep and your mum and dad finding out the way they did but maybe these thing happen for a reason, to make us stronger and more determined perhaps. Your girlfriend showing the film to everyone was a cruel thing to do,… Read more »