By Kendra Holliday | June 22, 2018
You know you’re in a sex-positive environment when a woman can doze off nude on a day bed outdoors by herself, and not worry about anyone molesting her.
And, of course, at other times you can see a bunch of people fucking in every one of the beds, in all sorts of fun combinations. That’s also very sex-positive.
My week at Desire with the Life on the Swingset crew was better than I imagined it would be. And I have a pretty good imagination!
I was nervous and excited to travel all by myself to a couples only lifestyle resort in a different country. I only knew a few of the people who would be my naked neighbors for the week (out of 120 rooms, the Swingset had booked 88 of them – next year, they’re booking ALL of them!) But I was determined to embark on this adventure with a positive mindset – after all, what did I have to lose? Just my clothes!
As inspiration, I brought this book along with me on audio – it’s all about discovering your personal legend, and has great quotes such as, “There’s a language in the world that everyone understands – it is the language of Enthusiasm – of things accomplished with love and purpose, and part of a search for something believed in and desired.”
I highly recommend it!
When I arrived, Cooper gleefully greeted me naked, with an espresso martini in hand.
The staff served me a glass of sparkling wine and a cool towel to refresh myself from my travels. I would continue to drink sparkling wine for the rest of the week! And other cocktails, and sushi, and guacamole, and cake, and lord knows what else! Eat, drink, and be merry!
I made a name tag charm necklace (helpful when you aren’t wearing clothes!) – it’s my Twitter header.
— Kendra Holliday (@TBK365) November 9, 2015
After my necklace was made (festooned with love and good charms!) I stripped naked and joined the group. A super nice couple gave me a tour of the resort. It’s not very big, but it’s laid out in a meandering fashion, right on the beach. Speaking of, my room had an ocean view!
Here is the first sunrise – I got up every morning at dawn and watched each sunrise naked, sipping sparkling wine, contemplating how I got here, marveling at my hard-earned, exhilarating sexual freedom.
I took this sunrise photo while standing naked on the beach. Clothing optional is THE BEST! pic.twitter.com/nm2r97jOsV
— Kendra Holliday (@TBK365) November 8, 2015
The first couple days, I acclimated to the culture. It was easy to mingle and make friends, even without all the planned events and activities. While there were a few younger couples there in their 20’s/30’s, it’s not cheap, so you need to be able to afford a trip like this. As a result, most of the guests were in their 40’s and 50’s, with some 60’s as well. I’d say 90% of the guests were white, but there were people of all body types and abilities. Sure, some were traditionally attractive, but what makes a person most attractive to me is their personality and energy. I was surrounded by intelligent, respectful, SEXY people with good energy. People were relaxed and confident, comfortable in their own skin, kind and supportive of each other. It was like being in the garden of Eden! I hit it off with one couple right away when we started talking about books. The husband knew about The Alchemist and The Way of the Superior Man. I told him about Cowboy Ethics, and he told me about Gottman’s Four Horsemen of the Apocalypse, which symbolize the four things that really destroy relationships. The wife was an animal lover like me, and shared some great stories. Sure, they were attractive, but the more I talked to them, the more attractive they were! We sparked with intelligent conversation and good energy! He reminded me of cool water/Sean Connery, and she reminded me of a spirited, fiery red mare:
. . . . . . . . . . After a couple days of getting to know each other, I asked them if they would like to play, but warned them that I wasn’t a late night gal, so we’d need to book some sexy time in the morning. They agreed to meet at 8am! Can you imagine – a breakfast threesome! That night I danced around naked for about ten minutes (they had live music every night and theme parties that would go until 4am), then scurried off to bed early, like I am wont to do. The next morning, I woke and got ready – the early bird gets the worm! When I arrived at their room, I was so surprised to see them lounging in robes, breakfast in bed, soft music playing. I got the royal treatment! There were experienced swingers, but had never had an mff, so that was fun. We all took turns being in the middle, receiving worship and orgasms! Even though I was only a little bit younger than them, it was easy to pretend they were a mom and dad figure, and I was their little girl. They took such good care of me – I told them what I liked, and they listened and were perfect lovers. When I came, they both pet me and murmured, “Good girl! Good girl!” After we finished playing, he had to leave for a scuba dive lesson, so she and I hung out on the beach and talked some more. Girl bonding – she braided my hair. 🙂
And here’s a boob shot:
— Kendra Holliday (@TBK365) November 11, 2015
I also had a friend take a pic of me fucking a champagne bottle like a coked out rock star, but you’ll have to track that pic down somewhere else… 😉 Speaking of drugs, I sure did drink all week, but didn’t do any other drugs, but often felt like I did! In a very calm, in-touch-with-the-earth way. For example, often as I walked along the shore, I would feel liquid running down my legs, so much so that I would look to make sure I wasn’t peeing or something! It was my body connecting with the female energy of the ocean, I guess. And I’d sometimes have floaty, out-of-body glimmers, like real life dreams… The following night, they made a liar out of me and kept me up until 1am talking about so many great topics! I was shocked to look at the time – I thought we hung out for a couple hours, but it was actually five hours! We topped the fulfilling evening off with some stargazing – she held me in her arms on the beach and pointed out the Seven Sisters shimmering over the sea, and we saw some shooting stars! The sky was brilliant and alive!
I had plenty of solitude – time to reflect and relax.
Sipping champagne naked on the beach, watching the sunrise 🍾⛅ pic.twitter.com/86o6pTGJVX
— Kendra Holliday (@TBK365) November 12, 2015
I brought books to read, but kept plenty occupied and only got a few pages in.
During my sunrise meditations, I would sometimes listen to classical music, and other times just get in tune with the lulling waves of the ocean. There was always a warm breeze playing on my comfortable skin. Lizards scampered every where; tropical birds called out to each other, high in the palm trees. There was even a coati creeping around! but anytime I felt like I needed company, I could venture out and connect with others. There was another couple I kept having amazing conversation with – sexual history, sex-positive parenting. He was pale with sparkling obsidian eyes, and she was tan with the most brilliant blue eyes. Together, they reminded me of a white tiger:
They had calm, assured healing energy. In fact, the next morning, he gave me a full body adjustment on the beach! I wore only a pair of lacy red, crotchless panties.
They’ve been in the lifestyle for a couple years, and had never had an mff, so I asked them what they would like to experience, and they suggested him going down on me, while she goes down on him. We also took turns with each other, both of us sucking his dick at the same time, that kind of hot fun stuff. (You can read the wife’s life transforming essay here!)
I also sat with them during some of the incredible workshops and demos – they played with my hair as we watched toy show-and-tells, sex swing 101, flogging, and the most intense demo – a pegging demo.
Cooper and his partner Ophilia showed us how to safely fuck a guy with a strap-on. It was so amazing and intense to watch a man assume the vulnerable position of being penetrated. He experienced these powerful prostate orgasms that shook his entire body for several minutes. You don’t get to see THAT every day! Here is a slice of the experiences – I watched this Life on the Swingset podcast recorded live. I’m impressed they got through it – they were passing around a bottle of tequila!
Finally, I also hit it off with an Indian couple who were new to the lifestyle.
Their marriage was arranged 20 years ago, when they were both virgins. They had to figure sex out on their own. Their wedding night was awkward, but it kept getting better and better. Still, the wife struggled with jealousy issues, and it’s a miracle to me that they ended up at a swinger resort! She was the first Indian woman I’ve ever seen in the lifestyle. I marveled at their courageous journey. They were experimenting with tantra and extended orgasms, and not just feeling erotic energy rush down their bodies and out their genitals, but also up their body and through their extremities, radiating and connecting them.
I was honored to be her first kiss with a woman. She was SOOO soft and exuded goddess maternal vibes. I laid on top of her, my head nestled in her pillowy breasts. Meanwhile, her husband fetched us water and ran a sensual feather over our bodies. He so adored and worshiped her! He kissed her and murmured in her ear, “I love you so much darling, I’m so glad we have this gift to share.”
That night, I went to bed feeling so relaxed and aroused. I thought about getting off, but decided not to. I was so surprised to wake up pulsing with pleasure – I had an orgasm in my sleep!!! That’s the third time in my life it’s ever happened!
So, I had threesomes with three different couples – TRIFECTA! It was so hot watching each of the couples interact – they were so sexy, sensual, and into each other.
I HAD to circle back to the water/fire couple before the end of the week. I worried that it wouldn’t be as amazing the second time around since the first time was so good, but it was EVEN BETTER! They just lavished me with TLC – so much so, that when he went down on me, and she suckled my breast, when I came, I burst into tears and it was so powerful! I loved feeling so comfortable and free.
After I calmed down, I suggested a fun threesome position – I laid underneath them as they fucked doggy style, and licked their pussy and cock – it’s such a hot view, with spectacular results. 🙂
SSDesire was an amazing oasis. People were so respectful and open-minded. It felt very matriarchal and bonoboesque – women led the way, and everyone was so happy and playful. Consent was key. Unlike a typical swinger crowd, the Swingset crew is down-to-earth, bi-male and kink friendly, very accepting and sex-positive.
So many dreams came true. Orgasms went off like fireworks all over the place. It was a magical wonderland. At one point, I watched 100 naked swingers jump up and down in a swimming pool full of foam, waving champagne bottles and pretty much freaking out to the song “Turn Down for What”.
Gluttony, sloth, lust, pride, maybe a little greed?… no envy or wrath, though. Responsible hedonism at its finest!
If people did wear clothes, it was minimal. The men walked around wearing sarongs, which was so sexy! On the last day when everyone is packing up and getting dressed, people are CRYING over having to wear pants again!
It was so fun hearing each couple’s story of how they got into the lifestyle, and their level of outness. Most people keep it a secret, and have to make up stories about their vacation. They have to dumb it down to “we went to a beach resort” instead of “we ran around naked all week with a bunch of sexually adventurous people and had a spectacular orgy.”
I’m so lucky I get to be fully integrated in my life. I can put my face and name to all that I do. I get to BRAG about all my fun adventures! There’s nothing secret or private about my life – I only have to protect the privacy of others.
In fact, my dad picked me up from the airport, and when I called him to let me know what time, he joked to me, “You better have your clothes back on, girl!”
And when I gushed to my daughter about my amazing time and new friends (not going into too much detail), she said wryly, “Did you have to use your safeword?”
HA, not even close!
I made this video for my wonderful new friends – I have no doubt I will see them again someday!
And reuniting with my partner was SO rewarding! He had a couple dates while I was gone, and the vibe between us was completely relaxed and recharged. We had amazing reconnecting sex. I’m so grateful for him, my loved ones, and having the best of ALL worlds. Life is beautiful.
If you can swing it, you should definitely sign up to join the group when they take over the resort November 3-10, 2018. You can find out more info HERE.
Every year Life on the Swingset hosts a full takeover of the greatest place on Earth:
Desire Resort Riviera Maya in Cancún, Mexico. In 2018, it will be Nov 3-10.
Desire is an all-inclusive resort, boasting a beautiful beach, pool, and hot tub, four excellent restaurants, three full bars, and, most importantly, space to be yourself.
Our takeover is the most inclusive and geeky trip that Desire sees all year with theme nights, educational events, and entertainment for straight couples as well as every letter in the LGBTQIA+ rainbow.
Live Nude Karaoke • Foam Parties • Dungeon Disco BDSM Night • Live Podcasting • Demos of Pegging, Fisting, & Flogging • Speed Dating • Wine & Beer Tastings • Costume Theme Nights • Orgies & Gang Bangs
“Truly the sex positive vacation of a lifetime!” – Tristan Taormino
For more info: SSDesire.com