Want to learn about some sexy things, new techniques, and things to try? (All workshops from 2018 trip, most will carry over to 2019)

Pegging & Anal Discussion & Workshop

Tristan Taormino, Cooper, and Ophilia, will be your guides to an anal discussion, live demonstrations of anal sex on both those with prostates and without. While demonstrating, they will discuss the act, preparation, and the elusive prostate orgasm. You’re encouraged to bring your own dildos and harnesses and participate alongside. In the past, it has happened, that this turns into a pegging train on Cooper, so that’s always possible.

Rum, Ropes, & Red Bottoms

A workshop covering mostly rope bondage and impact play like flogging and spanking. Demos will include bedroom bondage and impact play, and who knows what might happen once people start making requests! You’re encouraged to bring your own toys if you have them, and there will be time set aside for mentoring and open play. It will also be an opportunity to meet the Dungeon Night service tops as most/all will be there.

How To Plan a Gang Bang Workshop

Tristan Taormino will be bringing her vast experience to a workshop and discussion of the act that has become the most talked about and asked about on our trips, the gang bang. She’ll tell you how to plan and prepare, so you can throw one of your own before the week is out!

Energy Play

Ginger and the Professor discuss Reiki and energy play, including the philosophy behind it, the whys and hows, will demonstrate and assist.

Toy Show & Tell

Bring your toys to share and discuss with you fellow travelers, especially things that others may not have seen before.


Includes parties, dancing, singing, and flogging. (All events from 2018 trip, most will carry over to 2019.)

Cocktail Social/Welcome

The Swingset crew will be on hand to welcome you to the resort, raise some glasses, and welcome you to the resort in spectacular fashion.

Courtyard Karaoke

One of the surprisingly most popular events last year was Courtyard Karaoke, making a triumphant return with Dylan as your KJ and a collection of nearly 100,000 songs, your request is his Desire.

Disco Dungeon Night

The kinkiest of Swingsetters invite you to an evening takeover of the disco and playroom that will fulfill your deepest BDSM desires. Everyone is welcome, and you can get much more info from the first part of this guidebook. Monday’s kinky toy show/tell and workshop are highly recommended for anyone new to or curious about kink. – Click here for more info on this event.

Foam Party

Twice during our week, the resort fills the pool with foam from a massive foam machine. Dance and play to your heart’s content. Cooper recommends you indulge your steampunk know-how with goggles and a mask. Because Cooper…is weird.

Low Light Hot-Tub Stargazing

Multiple times during the week, after midnight, we’ll be dimming the lights at the hot tub to get some stargazing in. The Leonid meteor shower is, after all, the following week, and meteors are often spottable. The hot tub will still be host to its regular shenanigans. Just darker. So be careful.

Wine and Beer Social

Wine and beer aficionados among us gather in the rotunda to sip wine, and discuss whatever is on our minds (which may be a lot by Friday!)  You are encouraged to bring spirits from home, from the Airport duty free, or from the resort.

Bourbon Tasting

Long time Swingsetter Ginger Snap will present, discuss, and guide a tasting of a variety of bourbons.

Beach Workouts

Workouts on the beach consisting of mobility work, body-weight exercise circuits, and high-intensity interval training. Each session should last between 40 and 50 minutes.

Morning Meditation

Guided meditations to start your day.

Live Podcasts

Podcasts from our hosts recorded live in the courtyard.

Life on the Swingset

Cooper, Ginger, and Dylan podcast live and welcome you to be part of the audience and participate in the show.

Ending The Sexual Dark Age

JV and Shara host a live version of their kink themed podcast and welcome you to be part of the audience and participate in the show.

Sex Out Loud

Tristan Taormino hosts a live version of her Sex Out Loud podcast, asking questions and inviting participation from the audience.

As events are added, they will be added to this list. You can view the full schedule here.

Book Now!

Desire 2019
Our trip runs 11/2-11/9, if you need fewer nights, or a different week, please enter that.
Pricing is based on a FULL WEEK FOR 2 GUESTS, shorter stays will be adjusted.
Copyright 2018 Life on the Swingset | All Rights Reserved