Let me start out by saying that everyone’s experiences are different. I can only provide you with my perspective. My first CD/TG conference experience was Southern Comfort (SCC) in Ft. Lauderdale, FL in September 2016. I had only made the first tentative forays out in public in full Cyn mode earlier that year, which I wrote about in (https://www.crossdresserheaven.com/it-all-started-with-a-vanilla-milkshake/ ). After a few more outings in the middle of the year, Samantha G and I gave each other the needed courage to go to that conference, and we had a blast. In 2017, I ventured to Washington State for Esprit, and in 2018 I went to both Esprit and Keystone.

The Keystone conference is held in March of each year in Harrisburg, PA. It’s within a 5-6 hour drive for tens of millions of people (and thousands of our community!). The conference itself lasts from Wednesday afternoon through Sunday morning. It’s a mix of experiences ranging from classes/seminars to social/dinner outings and speakers. There are opportunities to mix/match/mingle with others in the community. The classes/seminars run the gamut from deportment/makeup/fashion classes to medical consultations for those contemplating or planning transitioning as well as helping to deal with the emotional and social aspects of being CD/TG. There are SO (significant other) meetings to allow our partners to engage with other spouses as well as Big Sister programs to help the new attendees overcome their shyness and fears of being out for the first time. There are speakers at several luncheons, dinners host leaders from the national CD/TG community and from the medical practitioners who serve that community. Attendees can choose from various registration plans ranging from Saturday only to evenings only to full conference participation.

So what is it really like? I encourage you to read my articles about each of the conferences I, and many others, have attended for details of my personal experiences (which you can find by going to my profile page and clicking on articles and/or forum posts under my cover photo and scrolling for them). In general, the best part (to me) of the conferences is to push the limits of our comfort zones in expressing ourselves. If you are like most of us, you fall somewhere on the continuum of 1) never having gone out in public dressed, 2) made limited forays outside but not interacted with folks, 3) had some interactions but tend to avoid close contact with others, 4) confidently gone out and either blended in without notice or wasn’t worried about what anyone else thinks, or 5) live full time with or without medically transitioning. The conferences are valuable no matter where you fall on that continuum. For “rookies” it’s a chance to dip your toes in the water while surrounded by hundreds of fellow CD/TGs-helping to ease the anxiety that almost all of us experienced in the early days of our journeys. For those who are in the middle of their journeys, it’s a chance to step forward and “get comfortable in our own skin,” and to enjoy ourselves for an extended period of time without having to worry about being seen by other friends or families who aren’t aware about this side of us. And for the veterans, it’s a chance to work on perfecting our presentation and confidence, and to perhaps gain insights as to where our next steps will lead us.

Unleash Your Inner Woman

The social aspects of the conference are vital, as you will have the opportunity to go out in groups to eat at restaurants around town-mixing with the public in a safe environment. There are opportunities to put on your clubbing outfits and dance the night away in the hotel ballrooms. (While I don’t dance while in male mode, Cyn loves to dance –even though not particularly great at it). And of course, there are adult beverages available in the hotel bars and pre-dinner cocktail get-togethers. You will meet dozens, if not hundreds of other girls, which you’ll make friends with and possibly choose to stay in contact with over the rest of the year. You can dress as formally or as casually as you like-though for many, this is the chance to wear that glittery gown you’ve been saving for a special occasion. You might even meet some of your fellow Crossdresser Heaven friends who are attending. I know that I will be there, and at least five other members of the ambassador team (Cloe, Samantha G, Stephanie Flowers, Rhonda Roe, and the irrepressible Wanda Full!) will be attending. I’ve also heard from several other members that are planning to attend.

You will see a new feature starting soon on Crossdresser Heaven about Events. You can indicate that you are attending as well as seeing who else will be there. You might PM them to make plans to get together at some point during the conference. We will also be highlighting other upcoming conferences and also local/regional events. Stay tuned for more about the new Events Page in the coming weeks as it rolls out! In the meantime, you can go to the Polls Forum to indicate whether you’re attending and to see who else is going!


So… if you have always wanted to get out and have fun, but were afraid to do it alone, you don’t have to let an opportunity like this pass you by. Registration is already well under way and you can find the detailed information on the conference webpage http://www.keystone-conference.org/ .

Hope to see you there!









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skippy1965 Cynthia

The Original Cyn, or OC for short. Cynthia is from Richmond Virginia, she crossdresses every day (lucky gal!) and has a knack for tracking down niggling technical issues so we can fix them. She is also on a journey of self-examination to figure out where her feminine journey will lead her, and is always willing to talk with others about their feelings and questions or her own.

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Dot (Donna B)m2fantasyLeah SantiniPennyMelissa Davis Recent comment authors
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Active Member

Nice informational article Cun. I’ve never been to a conference but hear they and similar events are a perfect way to meet other like minded people. I wouldn’t mind attending one myself. I would even go 1/2 conservative lol. Thanks Cyn for such a informative article. Jackie 😉

Trusted Member

Hi Cyn it’s Scarlett! Loved reading your entire article. You have an astute command of the English language and really know how to throw sentences and paragraphs together which leads me to believe you, like me, have some sort of formal education behind you or maybe sitting up on the wall in a frame or two. I used to teach regular Math and Algebra at the middle school level and later English Grammar at the high school level after retiring from civil service purchasing all of those high tech missiles that went underneath the latest jet aircraft that were rolling… Read more »

April (Pacific Princess)
Active Member

Wish I could join you guys at Keystone this year. I had a blast last year! Have fun!


Samantha G.....

We will miss you this year April !!!

Sidney Silver
Active Member

Hi Cyn! Thanks so much for sharing about Keystone! It indeed sounds like a blast! My wife and I are going to attend Esprit this year and I can hardly stand it I’m so excited! I swear I’m going to have 10 suitcases if I’m not careful! I have already planned out 5-6 solid outfits, and I have my sparkly dresses all set! I know for sure that I’m going to go to other similar gatherings around the county, and its nice to hear some firsthand experience. Any tips or advice you care to share would be most appreciated! I’m… Read more »

Samantha G.....

Hi Syd, my advice would be really plan ahead your outfits for each day. I’m trying to do that for Keystone and I’ll be happy if I can keep it to just 2 bags. For me the shoes will be the hardest to choose from, I’d like to keep it to 6 pairs for a 4 day event. We’ll see, LOL I’ve packed so much stuff for previous conferences but never use half of it. Just packed it all and decided once I got there what I wanted to wear. I’m gonna try to be more strategic this time and… Read more »

Sidney Silver
Active Member

Thanks for the advice and reply Samantha, really do appreciate it girl! I’ve been trying to do what you say-two outfits a day sounds realistic…but yes, shoes! For one who loves my shoes, that is gonna be tough girlfriend!
Had a look st your profile and pics – you’re GORG girl! So put together, and so much the aesthetic I want to achieve – classy and sexy. You inspire!

Thanks again for the reply!

Melissa Davis

Cyn, thanks for your thorough piece on the Keystone meeting in Harrisburg. I’d like to put in a word for a similar event that has been mounted for years in the Boston area. see http://www.firstevent.org. It may be smaller than Keystone (though it boasted 1,000 attendees, enough to sell out the suburban hotel), but the location might be good for those living in New England and New York. And it is by no means parochial. At the January event I made friends with girls from as far away as North Carolina , LA and Atlanta. And in particular I gravitated… Read more »

Brenda Maidenform

Can’t make Pa one but interested in Farmington Ct. April 27 But link not working for that one can you find out what is wrong?


Thanks for the article, Cyn! I’ve been back and forth about whether I should go this year, and you’ve tipped the balance. So, Penny’s going to town! See you in March.

Leah Santini

I’ll echo your sentiments, Cynthia! I went last year as my first time, was nervous and awkward but was immediately accepted and by the end of the week had come to relax and just be ME in that situation! The panels were informative, the people supportive and I’m already signed up and eager to attend again this year!

I’ve volunteered to be a Big Sister there, so if anyone wants some support and assistance, just let me know and we can chat about what to expect.

Hope to see a bunch of y’all there!



Oh I LOVE IT! One of my favorite conferences.
I will be there as a makeup artist vendor.
So excited to see all the girls again!

Dot (Donna B)

Thanks Cyn for sharing you experiences.

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