My high school class reunion weekend was such a wonderful dream. I told everyone how the reunion night went itself, but the next 2 days in town were just as fulfilling. On Sat the 9th was the small town event complete with a parade. The parade was to be at 3:30 pm and our cla...
Crossdressing experiences out in the world, at home and in life. Crossdressing situations that will make you laugh, cry and appreciate the wacky journey through life as a crossdresser.
Friday, 3/25/2022 (continued) From Col Bree’s seminar, Beverly and I made our way to Friday’s noon luncheon in the Commonwealth Ballroom, where the guest speaker was a trans-man. When Bev found a table, she waved me over, commenting, “I’ve got a surprise for you!.” She ...
If there is an angel who hands out blessings to crossdressers, then I received many in my lifetime. But, it seemed to me that every blessing also came with a curse. I was one of the lucky girls who had a mother who would play dress up with me as a child. The curse that came with ...
Hi ladies, As Australia moves out of the looong Covid lockdowns of ’20 and ’21, so too does the social life of us all. My beloved’s recent trips away helped Caty to achieve her long-standing and almost “last on the achievable CD list” of things to do whilst en femme. To...
A continuation… Up at 6:00 am, shaved, showered, dressed, put on my makeup, and excited, I head down to breakfast in the Dog and Pony. While waiting to be seated, I wondered if I would again eat alone. But, in walks a very tall CD.. I knew who she was after reading her nametag:...
Well, I did it! After a year of meticulous and detailed planning with my mentor, traveling companion, and all-around BFF Beverly (of CDH), we drove almost 600 miles to Harrisburg, Pa., and attended the 2022 Keystone Conference! And it was everything I had hoped it would be, and t...
I have never written an article during my time at Crossdresser Heaven nor had I experienced anything like the event I briefly attended last week. Attending the Keystone conference has changed my perception of our community, and my place in it. I made the decision to attend this e...
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,...
Preface: This happened about 10-12 years ago so the conversation is just from memory but as actual as I can remember. One evening I went out as Mary to do some shopping at a Fred Meyer store. I went there because it is close and had reasonable prices for cosmetics, not beca...
I have this very sweet genetic woman friend. She knows about Cassie. She is by nature a supportive and loving personality. And like all good friends among women, she is a superb listener. (Even if most of that “listening” is, in fact, back and forth emailing and instant messa...
Having reached what I call my “trombone” year, my seventy-sixth on the planet, and having been crossdressing since my eighth year – perhaps earlier – it is surprising to discover that there can still be things to be learned about this fascination that has with...
Hello Girls, I got the biggest surprise on a recent vacation. A little over a year ago my girlfriend asked me to stop cross-dressing if I wanted to stay in a relationship with her. She had wanted this in our relationship and encouraged it for more than a year. I had been cross dr...
A few weeks ago, I had the most interesting Sunday. Like many others here, in my male life, I do masculine things, as well as my love in dressing up to be the best woman I can be. Some know my love of cars, and I have a little red sports car which I spent quite a bit of time on i...
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Well, I guess it was a matter of time. Last Friday, a friend had a birthday party. This friend has seen Triesste perform, she has been amazingly helpful and supportive. My birthday was earlier this month. She and her friend whom I have also gotten to know took me to a surprise re...
I’ve been crossdressing on and off for 50 years. In the last five, I’ve been dressing quite frequently and have become aware of the effect it has had on my persona. Recently, I’ve been trying to ascertain a clearer, positive perspective on my crossdressing – the resul...
Throughout my crossdressing journey, there is one thing that I’ve found to be of paramount importance above all other things. You might perhaps think makeup. Getting that particular issue right is certainly important. I for one use enough foundation to plaster the walls of a la...
For nigh on 40 years, one of my crossdressing dreams has been to be hairless from the neck down. My beloved of 20 years plus complained a few years back about chest hair poking out the top of my t. shirts, so I fixed that and kept going until I hit my waist.!! Nothing more was sa...
As a closet crossdresser of many years, the opportunity to dress is not always available. The need for time alone with no disturbance is precious. Rarely get opportunity of more than a few hours these days so when chance of getting a few days alone at home arose I was so excited....
I could be wrong, but I got the feeling that the people I interacted with on this trip fell into two camps. One was very cheery and seemed really excited to be interacting with a crossdresser. The other comprised of people who treated me like any other person, not really paying m...
This is an article about my recent weekend trip, en femme. It was my first time dressing 24/7, and my first time out and about during the day. Without getting into too much backstory, I think it’s worth noting that this wasn’t actually my first time dressing in public. About ...
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