At the recent Keystone Conference, it was my pleasure to take several of their wonderful workshops, including the one entitled “Telling Your Children and Family Members” moderated by Dr. Michele Angello. More of a discussion than a “how to” workshop, I found it fascinatin...
Crossdressing and the Family
Crossdressing stories, advice and encouragement for crossdressers and their family members.
First, I wish to say how thankful I am to everyone here at CDH. Just being here and sharing with one another has been a large part of my therapy over the last few years. I know I am not alone, as so many are afflicted/blessed with this desire to CD. THANKS!!! Around four years ag...
Mirror on the wall showing my time spent preparing for my venture out; to maybe getting my nails done and a quick shopping run. Stop by for a quick lunch at a nearby restaurant before heading back home… before I get caught in my crossdressing. The only problem is that even thou...
The picture above is the first one I have submitted to this forum without any alterations. On the previous two, I used a SnapChat feminization filter that made me look younger and prettier than I actually am. I used it for two reasons: I liked the way it made me look, and my wife...
As some of you may know from my past posts, I have been slowly introducing myself en femme at work since the beginning of the year. About 2 months ago, I started dressing full female (make-up, clothes, nails, wigs, etc.) every day. It felt liberating, exciting, and it simply felt...
Growing up in the 60s and 70s was a different realm than the more modern world of today. Access to such things as my mother’s clothing was simply a matter of walking into her room, opening the “treasure chests” known as her drawers containing the objects of my d...
I took the picture accompanying this article with the Snapchat My Twin filter. It makes me look decidedly younger and prettier than I really am. I start with this because I did the same with my previous Crossdresser Heaven article and received flattering responses. I do not want ...
Stephanie: I am putting pen to paper to share a recent milestone and life changing experience. I had a full weekend planned to celebrate my 60th birthday, but it became much more than that. My 60th birthday celebration included a lovely open house party on Saturday and time with ...
In the movie “City Slickers” the character played by Billy Crystal asked his friends to talk about their best day ever (other than the birth of their children). So, this is the story of my best day ever as a crossdresser. A few months ago, through the wonders of social media,...
“You’re not a girl, but you are girly,” said my wife. I looked up from my crossword, puzzled about what had motivated her comment. She was pointing at my legs. In accordance with our negotiated rules, I wore guy clothes in front of her, but I had absentmindedly double-c...
As I sit here (in my LBD, wig, light make-up, and my favorite heels) on the cusp of my 68th birthday, I’ve come to the place, as I explained to my grandkids, known as the fork in the road. Which road do I take? I’m in relatively good heath, have been married for 35 year...
My journey to telling my wife and not being alone anymore

So I’m a long time crossdresser who has decided to come out to his wife after 23 years of marriage. So why now you might ask. There are two reasons, the first being me going through a health scare which caused me to accept my mortality and the second being that I retired e...
Love Yourself for Who You Are Ladies, Everyone loves a good story so I hope you find this one fulfilling and helpful. I will share a few thoughts on my journey from being a lifelong crossdresser to now accepting that I am a transgender woman (who cannot transition or come out to ...
Like most boys, I started cross-dressing by wearing my mom’s panties and nylon stockings. Doing so was both erotic and enjoyable, but being a pre-puberty 8 year old child, I was not sure of the reasons why. Eventually, with puberty, came the desire to wear my quintessential i...
As a kid, I was always fascinated about what women wore, including dresses and makeup. I was born in an Indian family that settled in Australia long ago. I have always been a straight guy until a moment changed everything. It was 3 years ago when I was at home with my then girlfr...
When I was 12 or 13, I convinced a very stubborn and old-school mother that girl jeans fit better than boys did. We argued but I got my way because I absolutely hated boy jeans and shirts and refused to wear either, which meant I wouldn’t be going to school, which also led...
I started Crossdressing in my teenage years. I would sneak into Mum’s room when she was not home and try on some clothes; loved the feel of Satin and Silk clothes. This Continued when I moved out of home, but I am ashamed to say (now) that when I lived with female flat mates, I...
This is a story of the first time I met my wife, how she found out about Bobbi and what she did when Bobbi came out. It started when I was living in Sacramento. I was bored one day and ended up calling the LiveLinks date line. At first it was just to kill some time, but then I he...
Hi ladies I wanted to share a brief history of where I was and where I’m going. My journey started around age five, I spent a lot of time with my female cousin. We would always play dress up. I loved it; the joy of being able to try on all her amazing clothes. This went on unti...
We are all possessed with both the yin and the yang, or the female and the male. It is when we are born that one of them dominates and that is what our outward appearance is going to be. But that is not to say the one that is not the dominant trait will not come alive at one time...
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