Sissy That Swing

08/25/2026

See you in Columbus!! 🥎🏳️‍🌈🏳️‍⚧️🫶🏼

⚾ GSWS is coming. Are you ready?

The Gay Softball World Series is almost here, and we can’t wait to be part of the celebration!

Mark your calendar for August 31 and come find Ally Nearby at registration. Stop by, say hi, and grab a limited edition Ally Nearby shirt while supplies last. ✨

We’re excited to celebrate the players, teams, supporters, and LGBTQ+ community coming together for an incredible week of softball, friendship, and Pride.

See you there! 🏳️‍🌈

08/23/2026

Thank you everyone who came out to support our last fundraiser before we head out to Columbus. 🥎🏳️‍🌈🏳️‍⚧️🫶🏼

08/17/2026

Pool Play Assignments!!! The excitement is definitely building up!!

08/14/2026

TONIGHT!!!

Come out and support Sissy That Swing! We are raising funds to help offset our travel cost to Columbus. 🥎🏳️‍🌈🏳️‍⚧️

Don’t forget those💵💵💵💵for our Sissy That Swing Go-Go Dancers!!!!

Theme: Sexy As F**k Beachware 🩲

08/14/2026

🚨📢 Two more weeks!!! 🥎🏳️‍🌈🏳️‍⚧️

Huge congratulations to Sissy That Swing from Orlando on punching their ticket to the Gay Softball World Series! We can't wait to watch them compete and represent their city in the E Division.

Drop some love in the comments below to wish them luck on their journey to the GSWS! 👇✨

07/01/2026

Sissy That Swing has earned the incredible opportunity to represent the Central Florida Softball League at our first-ever iPride Gay Softball World Series in Columbus, Ohio! 🏳️‍🌈✨

To help get us there, we’re hosting a 50/50 Raffle Fundraiser—and every ticket purchased helps support our team’s travel expenses while giving you a chance to win some cash!

🎟️ Ticket Packages:
💵 $10 = 12 tickets
💵 $15 = 20 tickets
💵 $20 = 28 tickets
💵 $25 = 35 tickets
💵 $50 = 75 tickets

📅 Tickets available through July 11
🎉 Winner drawn July 12

Whether you’re a teammate, friend, family member, or just someone who believes in supporting LGBTQ+ athletes and our community, we’d be so grateful for your support. Every ticket, every share, and every bit of encouragement helps us get one step closer to Columbus.

Please share this post and the flyer to help us reach as many people as possible!

Thank you for helping us reach our goals! 🥎🏳️‍🌈🏳️‍⚧️❤️

06/04/2026

Sissy That Swing E is taking on GSWS 2026 in Columbus, OH!!

We are looking for some additional sponsors to help cut down on our travel cost so we can focus on preparing for this week long tournament.

A few other fundraisers will start to roll out soon.

In the meantime, don’t forget to show our year round sponsors some love. Whether it’s healthcare, testing, huge Pride parties, or even a local bar with themed nights, including leather night. Pineapple Healthcare and Barcodes Orlando serve our community AND are LGBTQIA+ owned. The best kind of businesses to support this Pride month!! 🏳️‍🌈🏳️‍⚧️🫶🏼

06/04/2026

Now boarding: One Magical Weekend ✈️🌈

Visit us at the One Magical Weekend Expo and check in with our providers for no-cost DoxyPEP, free Pineapple swag, photo ops, and some more surprises! 🍍

Stop by our Pineapple Airlines experience and get ready for a first-class weekend 😎

04/03/2026

Thank you Pineapple Healthcare for supporting our community in every way possible.