HeartlandTG Revisited

| May 22, 2023
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Not since weeks BC (before Covid) hit, have I ventured out fully dressed for a gala event. Let’s see, I think that’s approximately four years ago.

And four years ago, is when I last attended HeartlandTG (HTG), a three-day crossdressing gathering in Oklahoma City. On May 4, 5, and 6 of this year the time finally arrived when I had to gather my feminine wear hanging in my closet and folded neatly in drawers to party with girls in attendance from many states and countries. 

Shelley Anne

Some may question why such an event happens in the State of Oklahoma. It’s a State not all that welcoming to transgender and transsexual folks. Simply, it’s where the original organizer, Hanna Olsen, hails from. And Hanna is still at it, albeit with the help of new board members.

This year’s event, the 17th annual transgender spring soiree and music jam, was moved to a new location in OKC providing a much larger venue for all activities. Approximately 50-plus girls were in attendance, and not just from OKC. Ladies from California to Connecticut, as well as Canada made their way to an event which has become somewhat of a family affair. Many girls have attended year after year. And there were several first timers. Everyone is welcome.

Held annually in early May and November, HTG now features everything from cocktail receptions and dinners to pool gatherings and live after-dinner music. HTG is billed as the largest transgender live music event in America. All musical performing bands must have a minimum of one transgender or transsexual performer for them to be invited to perform. Carol and the Cougars were this year’s performers, and they rocked the house.

For those who need help with their makeup, hair and nails, HTG provides an

onsite beauty salon to help ladies get dolled up for evening gatherings. Portrait photography is also available.

There are many fun activities. The May soiree is always held on the weekend of the Kentucky Derby. So that means a Kentucky Derby party at HTG. All girls are requested to dress for the occasion and wear their favorite hat too.

Prom Night is another special gathering and provides another opportunity to show off one’s feminine style.

And to continue partying until the very end, one must participate in HTG’s pajama party, held on the last night from midnight to at least 3 a.m. Not everyone is invited. Just those presenting as female (including cis females) and transmen. No cismen are allowed.

?The dress code consists of nighties and lingerie. No fleece or flannel is allowed. This activity is a BYOB and toys are allowed.  If requested, guests can be escorted to and from their room. 

And there are rules for pajama parties. No sexual exposure or contact is allowed, including between consenting or married partners.

Overall, HeartlandTG prides itself on being a safe and fun venue. Personally, I have never felt threatened, intimidated or out of place. I was parting with my peers, so to speak. If this is an event you may consider attending in November 2023 or next year, here are a few thoughts that will help you have a marvelous experience.


That is the goal at HTG events.


It shouldn’t have to be said, but respect other’s rights to have fun, be polite, be fun, don’t try to make yourself an issue.


HTG can’t cover all the event details on its website, or even when all get together at.  If you have a question, ask around or find a hostess and ask.


This is something that is very personal to a lot of guests. If someone presents as male, refer to them as such.  If someone presents as female, refer to them as such.  If you’re unsure, introduce yourself and deduce for yourself how to proceed. If you must ask, be tactful, a great way to get this information is an introduction such as “Hi, I’m Jane, my pronouns are She/Her.” They will usually respond in kind.


Don’t just go taking pictures nilly-willy, this makes some people nervous.  Some, because they have a lot on the line personally, others, because they just don’t like cameras.  If you are out and about and want to take pictures, please be mindful of whom you are capturing in the shot.


It is like being in a bar and one must be very careful about who you talk to about anything relating to any of these three categories. Guests come from all over the world, and we are in the middle of the nastiest political races in recent history, new local laws, have sports preferences, and participate in various religious traditions. Avoid having hurt feelings and anger erupt in the middle of a collective serenity.


The HTG venue is relatively safe, especially regarding sexual and gender identity, however, you can never be too safe.  As a woman it is important to take the little precautions like watching your drink. If you must leave it, ask a friend to watch it for you.  If there is ever a situation that develops that raises your suspicions, say something to a friend, a hostess, or security.

?Hotel security circulates around the property, so they are never far away, however, when going to your room, have your room key in your hand to minimize the time standing in front of your door. Keep the curtains closed unless you seek attention from passersby.  Many of guests were raised as males and were never taught these things, but as women, the risk of harm is very real.


If you don’t, you will have a hard time with Rule #1.  We all have social anxiety to one degree or another, and we share the same fears, so all should be able to relate to that. Do not let the fear of the unknown rule you. Nobody at HTG knows you from “back home,” and everyone will treat you as you. If you relax, smile, and chat, you will have a great time.

9. PLUS 1s

Feel free to bring friends and significant others with you, if they are respectful to transgender people. Everyone is responsible for their behavior, and they will be expected to follow the rules like everyone else.

10. 18+ UP

The new HTG venue is friendly to all ages however the event has activities that are quite adult. Alcohol being one of them. Sometimes it can be very difficult to make Rule #8 happen without following Rule #10.


The venue has specific areas for smoking marked on maps given to attendees at sign-in. Another area where respect must be shown.


HTG asks that all use discretion, so they don’t have to use theirs. There is a time and a place for everything from prom dresses to negligees. A schedule of events is always provided listing times and places. 

?For more information about HeartlandTG events, visit their website.

Here’s a side note about the State of Oklahoma.

Recently, much-amended legislation to ban gender-affirming treatments for minors was kept alive in the Oklahoma House of Representatives.

In its current form, Senate Bill 613, by Sen. Julie Daniels, R-Bartlesville, would prohibit providing “gender transition procedures” to minors under penalty of a felony.

“Gender transition procedures” are defined as medical or surgical services intended to “affirm the minor’s perception of his or her gender or biological sex, if that perception is inconsistent with the minor’s biological sex,” surgical procedures that “alter or remove physical or anatomical characteristics or features that are typical for the individual’s biological sex,” or administration of “puberty-blocking drugs, cross-sex hormones, or other drugs to suppress or delay normal puberty or to promote the development of feminizing or masculinizing features consistent with the opposite biological sex.”

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Category: Out & About


About the Author ()

Shelley Anne Baker has been part of the transsexual and transgender community for six years. Wandering about the California BDSM community, she finally found her stride in making the transition to dresses and high heels. Today, her women’s apparel, and shoes outnumbers her male apparel (that she just has to have for certain occasions, but such is life). She has seriously considered HRT, but now feels life has passed her by on that count. She is a professional writer and experienced corporate brand marketing and public relations consultant. For interview consideration and participation email Shelley Anne at contact@the420areacode.com.

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