Our Keystone Conference Adventure

Description of what Keystone is… Welcome to the Eleventh Annual Keystone Conference, “A Celebration of Gender Diversity,” hosted by TransCentralPA in Pennsylvania’s capital city of Harrisburg! You are in store for an informative, inspirational and joyous time among members and supporters of the Transgender community at the lovely Sheraton Harrisburg-Hershey Hotel.

“As the keystone bridges and holds together associated entities, Trans-identifying people do the same, and the Keystone Conference is a celebration of the unique diversity of gender and our central and unifying place in society. Pennsylvania is known as the Keystone State because of its significance in unifying the early colonies, and it is quite relevant that we hold this conference here in the state’s capital, ideally located within an easy drive from six major east coast cities.” From the Keystone-conference.org website.




My girlfriend, Judy, and I drove up from our home in the Upstate of South Carolina to Harrisburg, Pennsylvania for our freshman exposure to the Annual Keystone event. We spent a lot of the trip going over ways to best present our workshop material. It definitely helped to keep me awake as we drove. Eight hours later, we pulled into the hotel parking lot, brought in our luggage on one of those cart-thingies, checked in, took a deep breath as I took in all the other Trans-women who had already arrived… and was instantly intimidated.

Even though it was only Wednesday and the registration process was just getting under way, dozens of women had already arrived and were chatting away in the lobby and the hotel’s pub and restaurant as if they had known each other for a decade. I didn’t know any of them. How was I going to fit in? How was I going to be accepted? It was like my ten-year high school reunion all over again, feeling like an outsider who wasn’t accepted… even in the face of arriving at a conference where I had so many things in common with those in attendance. Maybe it was because of the eight-hour drive. Maybe it was just because I’m an admitted introvert when it comes to new public situations.


I was decked out in male-mode when we went to the pool area, sporting a red polish pedicure, shaved legs and upper chest to accent my old male-mode drab swim trunks. We bee-lined to the bubbles and steam of the hot tub, slipping in next to two young cis-women and one cis-man. (it does seem strange to have to label people as “cis” or “trans”). We soaked for a bit. They asked why we were there and we told them the truth. Gasp! What followed was a wonderful and open conversation about the trans-community and how the younger cis-generation sees it—and why they see it differently than the generations before them.

There was an ironic moment, though, when I told them I was a crossdresser that one of the women asked, “Isn’t that drag?” I found it ironic that crossdressing is still instantly and often coupled with the art form that is drag. I wasn’t offended or even stunned as I explained the sometimes-subtle difference in what distinguishes the two.


While Judy relaxed back in the room, I washed off the road weariness and started my transformation into what would be a three-full-day adventure as Savannah. We hopped on a charter bus and went to dinner. Still unsure of what we were in for, Judy and I caught a comfy booth and waited for company to join us. Company in the form of Jenny did slide in on the other side of the table and we got to start chatting and learning about each other, and having a yummy meal. We talked about our journeys and how it affected our personal lives and family. There was discussion about Maine Coon cats, communication companies, the upcoming presentations for the weekend, and how we were ready to go to bed after a long road trip.

Finally, back at the room, I disassembled back into male-mode and Judy checked out our conference book to plot our plan of attack for Thursday’s full day of panels and events.




I woke up at 5am in order to become Savannah for the day and get myself down to the lobby so I could focus on my continued re-edits and tweaks on our Saturday presentation slides and notes. Yeah, I’m a worry wart that way. I never seem to feel prepared enough, especially in a public speaking situation.

As 8am clicked by, Starbucks coffees and McDonald’s breakfasts sandwiches were the order of the day (addiction and thriftiness) to get us started. Going to the Target Starbucks as Savannah felt natural. I had no fear to be seen out-of-doors, even in the glaring morning of the rising sun.

Upon my return to the hotel (with only a few minutes to spare before the day’s first panel), Judy went one way to a workshop and I went to the first of two make-up tip classes. Brittney and Natalie from MAC started out nervously as they worked on the contouring and eye makeup of a willing model selected the night before, but quickly found their voice and their confidence. We jotted down notes on our phones or notepads anything we found of value from their expertise, just as they were incorporating some audience comments (as it applies to feminine cosmetics on the male face). I even went as far as scheduling a makeover for the afternoon before the gala event that upcoming Saturday night. They were both very sweet.

Judy met up with me for the second of the two make-up tutorial workshops and sat next to me… awwwww! After a while—since she doesn’t need all that many makeup tips—Judy returned to the hotel room for a bit of quiet reflection and solitude. We had already discussed about how this conference needed to be the most beneficial for the both of us, whether that meant to find separate workshops to attend, different people to chat with, or just have a quiet moment to ourselves. The point of the conference was to learn and strengthen our bonds of love and understanding.

After lunch and more conversation with the people immediately to our right and left, Judy and I decided on a workshop entitled, “Gender Dysphoria & Transgender: A Short Primer to Understanding Sex, Sexuality and Gender Identity”. Randi Sue Potter discussed chromosomes and genes, and how there is not just two specific ways (Male, Female) to see ourselves based on biological science. Afterward, Judy and I divided and conquered again when I split off to attend Dr. Gennifer Herley’s discussion on “Relationships Within the Context of Gender and Sexuality”. We were given an opportunity to tell our stories in a safe space as it applied to the session’s theme.



Thursday night’s festivities included a shuttle to the Hollywood Casino a dozen or so miles away. It was a welcome distraction from the thought-provoking day… workshop topics to be replaced with the silliness of slot machine gambling and buffet food. Judy was set to beat the odds by getting casino player cards and free $10 each of slot spend. We ate at the buffet so we got $10 more on the players’ card. The buffet was $26, so we, in reality, got $14 in free house money. I parlayed that fortune to $0.31 worth of winnings. Judy took my winnings (and her free money) and parlayed that into $43. So, we were able to wander around for an hour or two, and managed to come out with some cash.

Once we were bored, we wandered back to one of the lounges and ran into our shuttle driver at the bar. We asked about his life from before being a professional driver, and he asked about our lives and experiences. Looking like a slimmed down cross between Michael Chiklis and Rick Harrison from Pawn Stars, John was happy to learn all about us and enjoy his experience doing it.


One downside to this specific outing came in the form of Judy—my cis-female girlfriend—being misgendered. She is tall and slender, built with beautiful attributes. While I had my back turned talking with a fellow crossdresser, Judy was being chatted up by someone who took her for a transwoman. I would never mistake her for a transitioned MTF. And, while I can understand that we were in a venue predominately ruled by the trans community, it was a fairly blunt and insensitive act for someone to just make those assumptions of other people. Just as some people in the trans community feel very hurt when cis-people mis-pronoun or mis-gender them, the same rules do still apply to all people.

We got back from the casino around 11pm and called it a night. Savannah was washed away—I’m sure with mascara and eyeliner still clinging to life—and we set about reflecting about the day and hoping for a better tomorrow.




The next day Judy and I again parted ways for our own pursuits of knowledge. Judy wanted to focus on herself and other Significant One-centric events for the early part of the day, taking in a yoga class, “Ask a Spouse/SO” moderated by Mrs. Karen Lehman, Ms. Susan Bienvenu, and Ms. Kate Weber, and finishing with a luncheon entitled “Cis-Gender Spouse/SO Luncheon at the Lancaster Brewing Company”. Her focus was for herself and for those with stories similar to hers.

I spent my morning with Mrs. Jennifer White and her talk, “What about Part Time Trans Women—We are Trans, too.” She discussed her journey with her spouse and the balance to be found as a part-time feminine dresser. We gave our input and told our own “part-time” stories, reveling in the fact that I could find so much solidarity with like-minded individuals and supportive partners. The day was shaping up for me.


As much as I love Judy, it was important that I sought my own path for the morning—just as she was. The next workshop, moderated by Dr. Gennifer Herley and entitled “Coming Out… The Good, The Bad, and the Indifferent”, was a well-attended look at trans individuals of all types and the stories of their coming out. It is so important to remember that as each of us “come out” or transition, our families and loved ones also transition with us. There is no putting the genie back into the proverbial bottle after a reveal. There is only ever moving forward to becoming our most-balanced and most authentic self. I met several wonderful people in that workshop, including two transwomen, Missy and Trinity, from my adopted Upstate South Carolina, and an ever-smiling spouse of a crossdresser, Patricia.

Missy and Trinity joined me for the luncheon in the Commonwealth Ballroom where we heard from transgender male athlete guest speaker Chris Mosier. He is a trailblazing hall of fame triathlete, All-American Duathlete, and a 5-time member of Team USA and first transgender man to make a men’s US National Team. He has been instrumental and at the heart of change for the International Olympic Committee policy on transgender athletes. He dispelled many assumptions about what hormones do and how they “affect” the ability of trans-athletes.


Judy finally reappeared after lunch. She was still raring to go and positive about her morning. In fact, she had already established a short-hand with the significant one leading the workshop, “An Unedited Life: A Couple’s Journey Into the Open” we were heading to next. Mrs. Peg Fram and her trans husband Bree Fram talked about their trials and tribulations as a couple in the United States military at a time where trans wasn’t accepted and where “Don’t Ask, Don’t Tell” was still in effect.

Their story was stirring and the stakes they faced (and still face) were almost too high and too painful to bear. Peg told the story of their reveal… and how she was the one who was bombarded with questions about her trans husband… how she was the one who lost contact with the majority of her family and friends as a result… how she was the one who was trolled and pitied and looked down upon. That part of the story really sunk in and resonated for Judy—who was nearly at a point of being ready to execute her own reveal of me to her family before this workshop. She was emotionally rocked back on her heels with the thought that she could lose everything by admitting who she was living with.


In fact, those somber words put a fork in us for the afternoon. We skipped the day’s last workshop session and decided to enjoy the amenities of the hotel. So, it was back to the hot tub for us. This time, I was dressed as Savannah. I brought an older wig specific to the task of getting wet. We had both bought new one-piece bathing suits for the occasion. It was the first time I was in a public space as a spa-going Savannah. Even though the other people were most likely going to also be part of the conference, it was still a first for Savannah. Since my makeup needed to be redone anyway for the evening’s affairs, I wasn’t worried if it melted off too much.

There was a very beautiful crossdresser who chatted with us about work and her kids. She offered everyone a variety of drink options. We talked for some time, offering questions and answers about each other’s lives. That was the highlight… plus, simply being in the hot tub as Savannah in the first place.

The hot tub was filled with several of us, all of us just trying to relax and soak a bit. The good feelings didn’t last for Judy as she was again mis-gendered by one of the bathers. For the second time in two days, my beautiful cis-female girlfriend was hurt by someone’s assumptions, poor choice of words, and lack of manners. Just as a transman or transwoman deserves to be acknowledged in the way they feel most comfortable, Judy wanted the same for herself. That interchange soured her experience in the pool area and we packed up and went back to the room.


We skipped our off-site dinner plans in favor of dining in the hotel’s restaurant. Someplace quiet. Someplace away from the crowds. Someplace where we could reflect on our experiences. We had showered and got all dolled up again, washing away the hot tub chemicals and replacing them with fresh dresses and foundation. At the restaurant, we talked about everything we had learned and had experienced. Our conversation was laced with the hurt that Judy still felt from her misidentification, her worry about losing her entire family in her effort to support me as a trans individual, and a general stress-laced doggedness and tiredness from two full days of being around trans folks and situations that are outside her general and typical norms.

Upon returning to the room, my wig was quickly removed (so my head could breathe again – lol). We continued to talk about the day and evening’s events, but the stress wasn’t so easily dissipated by words or support. What we needed was time to recover. We lay on the bed, Judy ready for relaxation and me on my back so that my makeup didn’t get wiped on the pillows or sheets. I promptly fell asleep at 8:20pm—until my own snoring woke me up.

The Keystone dance party that was to begin at 9pm was not in the cards for me. I was tired. We were raw emotionally—for good and not so good. Judy felt she was holding me back and told me that I should go to the party. But I was weary, too—like she was. The result was a quick deconstruction from Savannah back into my male-mode and a prompt lights-out at 9pm. Tomorrow was going to be another day.




The next day was the day for our workshop, “Living with Crossdressing: After the Reveal – Realizations in the Relationship”. While I had woken up at 5am Thursday and Friday to go over the presentation and get Starbucks coffee for me and Judy, Saturday was a sleep-in day until an astonishingly late 6:30am!! I snuck our banner and books down to the conference room we were to workshop in before anyone was milling around. The box of books went under the table and the banner was partially put together so that it could quickly be erected before our scheduled workshop. I was as ready as I could be prior to our actual afternoon seminar.

I attended Ms. Ann Murdoch’s “Celebrating Trans and Nonbinary Identities” workshop, even helping her put together a frame and curtain assembly prior to her own scheduled start time. We participated in a lively discussion about how we should celebrate our true selves. While I am still coming to terms with whether I fit into terms like “trans” and “nonbinary”, I still felt like I belonged in the periphery of these strong and capable individuals. In truth, I see myself as a gender-fluid, binary, transgender male-to-female crossdresser. That is what I celebrate.

While Judy was set to attend Peg Fram’s “Spouse’s Circle of Positivity”, I decided to take a chance on Mr. Noah Lewis’ “Making Cisness Visible: Naming Cis Ideals That Shape Trans Lives”. I am glad I did. Not only was I given something to think about as it related to tangible brain patterning reasons for why a trans person may detest the body they were born in, I was able to sit next to a remarkable woman. She was the mother of an adult male-to-female trans daughter. This mother, Susan, was set and determined to learn all that she could about the trans experience so that she could better be supportive of her daughter. Even as the group broke up after the workshop ended, we continued to chat about crossdressing and transgenderism.


There was one last luncheon to attend with Judy’s new friend Jill and her crossdresser husband Ronee… there was time needed to shave (yes, a second shave for the day) and freshen up my makeup in our hotel room… there was another workshop to attend focused on understanding blame and shame. All of that was a wonderful blur because my heart was pounding with nervousness and my hands were sweating with anticipation for our own workshop. I wanted to make a good impression.


“Living with Crossdressing: Defining a New Normal” is the book that I wrote and Judy contributed to. It was the subject matter for our workshop. With minutes to go, I tried to connect with the crowd (warm them up). I tried to think about all of the bullet points I had written out (and were written in the notes in my hand) but couldn’t even commit any of the words to memory. Judy, on the other hand, was rock steady. Every topic point we were to discuss was simply a PowerPoint slide of something we had already lived through.

Before the bottom of the 3 o’clock hour arrived, Susan (the mother of the adult trans-daughter) from earlier in the day came in. She had promised me that she would sit in on our presentation. Her eyes were glistening with tears because she felt torn about keeping her promise to me and going to another panel that was more geared to what she needed to learn for her daughter. We looked at the catalog for the conference and I told her that she needed to go to the other workshop. We hugged and I told her to reach out to me anytime.

Jill and Ronee were there for us. Patricia, who I had talked to after Dr. Gennifer Herley’s workshop, was there. There were couples with long-standing marriages and those with a crossdresser who had only been out twice in her life sitting alongside a wife who just been told.

I won’t go deep into the presentation itself as I will be posting it as its own resource on the website shortly. [https://livingwithcrossdressing.com/our-keystone-conference-workshop/]. I will say that Judy and I made a great team and created a solid experience for those in attendance. Many came up to buy the book that the workshop. Many congratulated us on a job well done. Our presentation was complete. There were no more workshops to attend this year. We were the last. Only the gala remained.


The gala event was attended by hundreds of beautifully dressed men and women, all lined up to venture into the Commonwealth Ballroom for the dinner, comradery, reflection, and, maybe, a deep exhale for all that had come before. The Keynote speaker, Kimberly Shappley, delivered a message of acceptance and unconditional love for a child who declared in a loud voice at an early age that she was meant to be a girl. To try and recreate the moment and emotions we experienced would be a tall order, indeed, so I will just let you know that we were moved by her words.

The dinner commenced and was consumed. Stories were shared. Selfies were shot. The plates were removed and the dancing and music began. It had been an engrossing and emotional few days. The crowds ebbed and flowed to and from the ballroom. The night went by too quickly and we were left with a final deconstruction of Savannah back to a male-mode that hadn’t been seen in the sunlight since late in the afternoon of the previous Wednesday. No more shaving… no more padding… no more extra time needed to set aside in order to become her.

Yes, Savannah involves work to become. Yes, she is heavy to carry around from place to place in my luggage. Yes, she takes time and dedication and practice. And, as with anything worth pursuing, Savannah will always be a worthy and important part of my life.

Author: livingwithcrossdressing

I am many things. I am a life-long male-to-female crossdresser and author. I hope my journey is of value for those who may need help to foster, support, and understand who they feel themselves to be.

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