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.

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!









  1. Jackie 6 months ago

    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 😉

  2. Scarlett398 6 months ago

    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 off of the assembly line at whatever time were were purchasing the weapons to mate up with the software in the jets. I taught for six years and raise two boys who are now 43 and 40 and that’s why I’m allergic to kids now! Every time my sexy redhead and I go out to eat and the hostess at the front asks us where we want to be seated, we always tell her or him as far away from kids as we can possibly get! They usually do a super job honoring our request! HA HA!

    I wish I could join you and the girls at one of these huge events that sound like a real blast to be at! But it won’t ever happen. The wife would never let me disappear to anything having to do with my cross dressing into sexy Scarlett for a single day much less four or five days. She’s still not into my cross dressing at all so I have to do my biweekly photo shoots of Scarlett here in private at our dream home and then share the photos with you girls and that’s my way of getting Scarlett out of the house every other week or so! I’m lucky I get to do that. At least she lets me keep all of Scarlett’s things inside this spacious new palace of ours and will call or text me with a two hour heads up if she’s coming home from work early instead of just walking in and surprising me with some cute or sexy dress or outfit on with some sexy heels and my makeup on. So my meeting with you girls will never happen unfortunately.

    I loved reading your article and I so happy you get to partake in all of the fanfare going down at these get togethers/parties!

    Well that’s it for now Cyn! See ya in the chat room funny girl! XOXOXO Scarlett

    P.S. Big photo shoot with lots of new stuff happening this Wednesday or Thursday so be on the lookout for some super new photos coming up by Friday of this week!

    • Author
      *skippy1965(Cynthia) 6 months ago

      Thank you for your kind words-I DO love to write. It helps me express my thoughts, and (I HOPE at least) that it gives encouragement to others who are trying to push their envelope in expressing themselves-whatever that entails! I have written many thing here over the years (and posted even more pics than you LOL(just in my private photo page). Glad that your wife accepts your need to dress even if she doesn’t want to SEE it herself. TTYL.

      • Scarlett398 6 months ago

        You’re welcome Cyn and I love our time together in the chat room. We have a lot of fun in there!

        Have a wonderful weekend girl friend! XOXOXO Scarlett

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


  4. Sidney Silver 6 months ago

    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 so damn happy — truly the happiest I’ve ever been—that I’ve finally discovered who I am. Every day is a gift to me. I can’t wait to spend time with other girls and have some great times!

    Thanks again,

    • Samantha G..... 6 months ago

      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 only pack what I need. Anyway that’s my 2 cents. Hope you have a blast at Esprit.


      • Sidney Silver 6 months ago

        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!

    • Author
      *skippy1965(Cynthia) 6 months ago

      I have to laugh cause at my first conference (2016 SCC in Lauderdale) I had eight suitcases (two nothing but shoes) and five wardrobe bags! (Needless to say I drove there not flying). Mixing and matching is great advice-leggings and skirts and tops that you can switch up saves space and gives variety. And yes you’ll want some dresses for dancing! Don’t forget accessories! Most important , have fun! Be confident! And I will be at Esprit this May for the third time so look for me and April Showers(another ambassador who is going)! I will look similar to my pics here cause that’s all me LOL!

  5. Melissa Davis 6 months ago

    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 toward and shared a table with three well turned out ladies who were more or less of my generation, crossdressers with families in which the children were now out on their own. We tossed around questions like, Should we come out to our families if they don’t already know? The consensus was, more or less, if your kids don’t know now, maybe they never will.

    I pass along the anecdote because it might be encouraging to younger crossdressers. When you are older, some problems may be easier to handle. The wives of my new friends didn’t like crossdressing, but they willingly accepted it. Life is normal, even for the wife who discovered her husband’s other identity when she stumbled on his video file.


    • Author
      *skippy1965(Cynthia) 6 months ago

      Thanks for sharing! We are going to be starting an Events Page soon here (stay tuned 🙂 !) And First Event will definitely be on that. When the Events Page launches please do PM me with more details and I will at that time also encourage you to write an article about it! We are hoping to encourage folks to get out and attend these events to foster a sense of community AND to show the world that we are just regular folks with an added flair!(and a great fashion sense! LOL)

      • Melissa Davis 6 months ago

        Thanks, Cyn. I’ll watch for the events page.


  6. Brenda Maidenform 6 months ago

    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?

  7. Penny 6 months ago

    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.

  8. Leah Santini 6 months ago

    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!


  9. m2fantasy 5 months ago

    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!

  10. Dot (Donna B) 5 months ago

    Thanks Cyn for sharing you experiences.

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