How to Start An Orgy

It’s not that hard to do at a Jamaican sex resort…especially without shame and the intention to have fun and be free.

Enjoy this excerpt from my novel, Pretty Kinky for a Love Story, available now on Amazon.

Our second trip to Hedonism II in Jamaica was a respite from the drama of practicing non-monogamy back home. We were going back with experience — relaxed and secure now, in who we were and what we wanted. Last time, we’d only just barely opened up what would become our Pandora’s box…

But now, for one blissful week, it was just me, Jack, and the other perverted people who partied alongside us in the pool — and on the mattress.

Ryan and Lauren (friends we’d met at a different nude beach in Jamaica years before) were traveling with their swinger friend group, and we happily accepted their invite to tag along. We weren’t sure if we qualified as swingers or polyamorous or whatever, but it didn’t really matter and we didn’t really care. We just wanted a week of sex, fun, and open-minded people in our own age range.

This group was quite different from the Sunset Beach crowd and the people we’d met at Hedo previously. They were partiers, complete with drugs, poolside drill-do demonstrations, and uninhibited sexuality. These people didn’t give a shit what others might think of them, but they weren’t jerks. Most were insanely direct but polite, and they respected others who behaved the same.

Take Mila, for example, who had one of those Daddy kinks.

Now imagine Jack entering the scene as the hottest father of four. He says, “I drive a minivan,” and this girl swoons.

Next thing you know, it’s only our second day there and already he’s getting a handjob from her in the middle of the crowded pool, wearing nothing but a huge smile and his felt cowboy hat.

I know that seems a little fast, but we were prepared for this trip. We’d talked through our “Wants, Willings, and Won’ts” for weeks beforehand.

For example, Jack wanted to have daytime sex in full view of others (no surprise — he’s a total exhibitionist), and I was willing. We were both willing to engage in sexual activities with others if they were a good match, but we won’t do anything with anyone that the other person isn’t cool with.

I suppose the time that I spent making out with Mila earlier that day counts as vetting her, so Jack was in compliance here.

I also wanted some very nonsexual things that, knowing me, would lead to sex. I wanted to savor my time and shed my inhibitions. I wanted to feel carefree and peaceful, but with energy. I wanted to be in the moment. I wanted to explore and be adventurous, and I wanted to do things that I couldn’t do back home. I wanted to play.

And Jack definitely wanted a beautiful, voluptuous younger woman to compliment his cock. This was not news to me, but all the same I was glad to see that he was enjoying his time.

I turned to Todd, her husband. He was cute enough. Bald and smiley, which was all perfectly fine, but way taller than I normally like. Still, he was sweet, and I wasn’t going to date him. That’s the best thing about vacation sex — it’s just this one week, maybe this one time.

So he and I talked, and then we kissed a little, too. We flirted, and it felt good to be desired, to feel that tension rising between us. It was fun to know that others were watching all four of us to see what might go down. Maybe I am a bit of an attention whore. Perhaps I just didn’t care about what others saw, or perhaps I was as intrigued as the rest of them.

Or perhaps I’d had one too many Long Island Iced Teas with Mila and the other women in our group. On second thought, I think I had the just-right amount, if shedding inhibitions was my goal. It certainly paved the way for that makeout session with not only Mila, but a few of the other women as well.

My point is, we were having a great time, Jack now with Mila and me, flirting with her husband.

In our conversation on kinks, Todd mentioned an electro-shock sex toy thing. I’d never tried one of those. “I brought it here,” he informed me, his raised eyebrow invitation enough.

The tropical thunderstorm that struck at that very moment solidified our afternoon plans.

We went back to their room, where Mila and I showered while discussing our needs for safe sex, including STI status (all clean) and wants/willings/won’ts.

It could have felt transactional, but instead it felt friendly and respectful. We were playing a game, agreeing on the rules beforehand so that everyone could have the maximum amount of fun. This is where Jack and I learned that there was a time and place for swinger sex, if we found the right people.

Our playtime that day would begin with the electro-shock thing, with me as its “victim.”

I lay on my back on their bed, naked, of course, arms and legs spread. I could see my reflection in the mirror on the ceiling, as well as everything that was happening around me. Mila and Jack flirting, Todd adjusting the dials of the machine, the wand in his hand.

As I lay still, Todd demonstrated how to tickle with the wand. Soon, Jack and Mila joined in, three people hovering over me, teasing me, touching me. Even without the wand, a touch from another would omit a jolt of electricity, as I was holding some sort of grounding apparatus, too. It was a scratchy feeling on my limbs, and an intense feeling on my nipples and labia.

We ditched the electricity after a bit. Overall, it had been more interesting than arousing, and I didn’t find it nearly as pleasurable as what came next. Which was, you guessed it, a foursome.

I know that some of you are hankering for details on this, and I’ve got to say that the mechanics were much the same as with any foursome. Hands and mouths and genitals everywhere, people lined up in various positions so that everyone was pleased.

Like me, sitting on Mila’s face while Jack fucked me from behind so that his balls got a little Mila tongue flick, too, all while Todd fucked Mila. That was the position that got the attention of our friends.

It’s a Hedo thing to leave your door open while you fool around, if you want others to inquire about joining in or if you just like showing off your game. When Mila asked if we could keep the door open, I shrugged. Didn’t bother me either way. Jack was more enthusiastic in his affirmative answer, him being a huge exhibitionist and all.

So the door was open, and in the aforementioned arrangement, Jack was insanely close to blowing his load in me…when we suddenly heard a Jersey accent billowing “Oh MY Gawd, that is so HAWT!”

We all looked up to see a bunch of our new vacation friends packed into the doorway. Ashley with the Jersey accent, her husband the cop, Evan the principal who looked like a wizard, Lily his wife, and Steve the Single Guy. “Keep going!” one of them shouted, and we all tried, but I’d already burst into a fit of giggles. The moment was lost. We’d have to change course to keep the party going, and so we invited all of them in.

And that’s when it turned into an orgy.

Ashley jumped onto the bed and began to pleasure Mila with her mouth. The rest of us admired them until Lily, who’d left to get supplies, burst back into the room with the biggest vibrator wand that I’d ever seen, already suited up with a clean condom. She handed her husband two beautiful leather floggers and then plopped onto the bed, seated with her back against the headboard.

Should I mention that most of us were already naked? When I tell these stories to people, I always forget that part.

We all did our own things as we explored for a bit, careful not to share fluids with anyone that we didn’t already know and have vetted. There was a lot of kissing and nipple play, hands everywhere, and some fun with the floggers, but not all that much actual fucking. A true orgy requires more preparation, I’d imagine, as well as more mattress space.

This wasn’t romantic, or meaningful, or deep, but it felt natural, almost like a scene out of the untarnished Garden of Eden. It was a joyful session of experimentation using our bodies. There was no shame. Everyone was consenting, kind, and having a good time.

Sex doesn’t always need to be about deep feelings and lifelong commitments, does it? Can’t we just take a break and have some fun once in a while?

Jack and I were in agreement on all of this, and so we partied on.

Interested in more? Perhaps you’d like to read my novel, Pretty Kinky for a Love Story, available now on Amazon.