Candy's First Gangbang & DP

Candy's First Gangbang & DP in Jamaica

My name is Candy. My husband Howie and we have a wonderful marriage... all a woman could ask for. We both have successful careers, a beautiful home, we are very loyal to each other, we love each other unconditionally... and our sex life is out of this world amazing. Despite busy jobs and busy lives, we both make sure to set date nights, which usually fall on the weekends. Sometimes we do dinner and drinks, then end up home having great sex. And sometimes we just never leave the house for a weekend and don't put clothes on the whole time. It's important to make that intimate time for each other. It's what helps keep the spark in a marriage and fosters and emotional closeness.

Howie and I have been working like dogs for months in anticipation of an awesome Caribbean trip we're about to embark on. We're planning to go to Negril, Jamaica for eight days with stays at a few different places. Neither of us have ever been to that part of Jamaica, and we're super excited, as we've researched and heard that it's one of the most beautiful stretches of beach in the Caribbean on one end, and gorgeous rock bluffs on the other end with the most beautiful sunsets in all of the Caribbean. Our first part of the stay is at a cute, quaint little boutique hotel on the north end of the island called The Sunset Palms. And the later part of our stay is on the bluffs overlooking the ocean on the south end called Bredren Cliffs.

The term "bredren" is a common Jamaican slang term for "friend" or "brother". By all accounts from our research, both locations look absolutely gorgeous in very different ways. The Sunset Palms has a modern architecture feel with vibrant colors everywhere you look from the building colors, to the artwork, to the variety of flower and plant life that covers the property. And it's nestled literally right on the shoreline where you're no more than 20 to 30-yards from the hotel to the water. The Bredren Cliffs has another unique feel, but everything is built by stone. The walkways, the structures, the cottage type rooms on the property... everything. And it's all open-air, as the breeze is amazing at night. The location doesn't have beach access, as it's literally overlooking the ocean via cliffs, but it does have an amazing infinity pool that's probably 25-feet above the water line of the ocean. We're only staying here the last two nights of the trip.

And then there's a night in between that's the real story here. In between both those stays we are staying overnight at a place called Desires Island. Desires Island is literally a tiny private island right off the coast that you have to take a boat taxi to get to. It's super small, like not even a half mile from one end of the island to the other. And it's the only resort on the island... for good reason... it's a swingers/nudist resort. Howie and I have been talking about going to a resort like this for years, but frankly neither of us had the courage or confidence to do so. We've done endless amounts of research on this place. And the more we learn about it, the more we realize there are a lot of misconceptions out there. This is not some filthy hedonistic island where everywhere you look people are fucking like something out of a porn video. People are actually very respectful. And if you don't want to be bothered, you're left alone. If you want to have sex with your partner by the pool or on the beach, you can. If you want to join other playmates, it's not hard to find. It's taken quite a while for both of us to get to this point in our relationship, but we're now at a place where the more erotic it is, the better. More on that in a bit!

So now you know the lay of the land for our trip. We live in the Midwest, so we had a connecting flight in Miami, landed at Montego Bay, Jamaica airport, then took about a two-and-a-half-hour drive by shuttle to the first hotel. Upon arrival at The Sunset Palms, it was immediately evident that we had made the right choice. This place was stunning and everything it was built up to be. On a lot of our trips, we do a mix of relax time and excursions. This trip, however, was all about relaxation for both of us. And that's exactly what we did. We chilled on the beach, ate amazing food at the on-premise restaurant, and hung out at the beach bar that was also on-property. The hotel maybe had a total of 50 rooms, so you can imagine that the vibe was a little more chill and a little less crowed than your typical all-inclusive type resort. And in Jamaica, it's certainly not too hard at all to slip into that chill beach vibe. It's part of the Jamaican culture. "No problem, 'mon." They are about as chill as it gets, and that's exactly what the doctor ordered for both of us.

We were staying at The Sunset Palms the first five nights of the trip. Our first three days were pretty mellow and relaxing, and Howie and I just did our thing and kind of kept to ourselves while on the property. On day four after another relaxing day on the beach while watching the sunset from the bar patio deck, our trip to Desires Island came up. Howie says to me, "Are you ready for Desires?" with a shit-eating grin on his face.

Shyly I said, "Yes, but I'd be lying if I wasn't a little nervous. But we've discussed this at length back home and I think I'm as ready as I'll ever be. Plus, I think it has a chance of being super hot!"

So full disclosure... I've never been with more than one man at a time sexually in my life. Howie and I went to a strip club once that had a private area where we saw others fucking, and we even fucked in front of others, but that's where that ends. For a while now, he and I have been talking about fulfilling each other's sexual fantasies. And mine is to be in an orgy scenario and have multiple men pleasing me at once. Yes, I want to get gangbanged! Now this takes a lot of trust in a relationship. To have the ability to remove any emotion and just take part in a physical act with other men is something you both have to be onboard with. But Howie and I deeply love each other, and quite frankly we're both freaks in the bedroom. Plus, we had extensive conversation about it back home before we planned this. Clearly he's onboard. And I am too, but I just want it to go smoothly with nothing awkward or embarrassing. The truth of the matter is that I'm shy when it comes to initiating anything sexually... but... I'm down for literally anything Howie wants to do or do to me. I kinda think it's hot for a man to just take control of you in that way. Just let him do what he wants, put it where he wants, cum where he wants. That really brings out the hidden little whore in me.

Howie and I are great communicators when it comes to sex. Again, I'm a little shy, but he has a way of drawing sexy information out of me. And this whole trip and stay at Desires Island came from a conversation about nothing other than my deepest fantasy. So one of my pleasures, or kinks if you will, is that I love to have both of my holes filled and fucked at the same time. I just absolutely love that feeling of being completely full of cocks in both my holes. It makes me absolutely explode. At home we do it with two dildos. One in each hole. Sometimes with a dildo in one hole and Howie's cock in the other. We also have a half torso sex doll with a huge stiff cock. I'll get on top and ride that cock, and Howie will enter my ass. I know anal play isn't for everyone, but it actually feels amazing for me. Plus, there's just something so dirty and hot about being completely filled up in both holes. And Howie, he loves it too. He's such a dirty boy, let me tell you. I'll ride that cock of that sex doll with Howie in my ass, and I'll literally make a mess of the sheets I cum so hard. And seemingly seconds after I cum, Howie will shoot such a big load of cum in my ass each time. That's another kink I have, by the way... I love to feel hot cum shooting in my ass. I love to be ass fucked and cum in. So fucking hot! To feel his cock pulsating while hot cum fills me up inside is next level hot.

But let's not get too ahead of ourselves here. Howie and I continue the conversation and every step of the way he's ensuring my consent that its exactly what I really want to do at Desires Island, assuming we find the right playmates... to have both of my holes filled. The "other guy" will fuck my pussy and Howie will fuck my ass. It sounds so hot to talk about, but trust me when I say I'm a shy girl that is slightly nervous about it all. But we're here to have fun and feel free, so I'm just going to go with the flow as long as it feels right with the right people. Plus, Howie likes to tell me how he loves to see both my holes filled, and he's really excited to see real cocks in both my holes.

As Howie and I are knocking back a few Red Stripe beers on the beach, a Jamaican staple, I notice two couples enter the bar area. All four of them were probably our age, maybe a few years younger. And they were all quite attractive, very fit, and very well dressed, as far as casual beach attire goes. Howie and I continue to chat as we watch the sun set and eventually get swallowed up by the ocean. Howie then says, "Want to go inside the bar area?"

I say, "Sure, let's do it."

This bar is a pretty cool setup. It's covered but the rest is open air. The breeze from the ocean flows through the bar area with mellow Reggae music playing in the background. The ceiling is painted with Jamaican themed murals reflecting the culture that surrounded us. Coincidentally, we sat at a table near the two couples I saw walk in earlier. I see one of the guys eventually get up to go to the bathroom. What I presume to be his wife is just taking in the beauty of the beach and faint glow of what's left of the sunset on the water. She looks over in my direction and we just happen to catch eyes. She gives a friendly smile, and I return a friendly smile back. After another beer or two Howie, as he always does, strikes up a conversation with the man she's with. So myself and the woman he's with share another smile with each other when she says to me, "I absolutely love your earrings. Where did you get them?"

I told her where I got them and then complemented her on her beachy, yet very sexy dress. It was totally something I would wear too and was genuinely interested in where she got it. As Howie is now chopping it up with both guys, the other lady kind of scoots her chair closer to her friend and enters the conversation. Both were really nice, sweet girls. And very good fashion sense! Eventually everyone properly introduces themselves. Jake and Sandy were husband and wife and then Max and Erica were the other married couple. They were all Midwesterners too, so clearly everyone was enjoying the beauty and good vibes that Negril has to offer.

Beers are starting to flow and before we know it, a couple hours had passed. They were such fun, cool couples to hang out with. And we all seemed to have a lot in common. We were really enjoying laughing and chatting it up with them. As we're all talking I noticed Sandy (cute dress girl) casually and somewhat discreetly slide her hand down Jake's leg and rub his crotch over his shorts. She didn't do it long and super obvious, I just happened to notice. As she was removing her hand like nothing happened, she looked over at me and noticed that I caught her doing it. She gave kind of a sly grin and then just went back to talking and engaging with the group like nothing happened. I thought to myself, I bet they're fun in bed.

The night was wrapping up. It was close to midnight at this point. We had a super fun night hanging out with them. Howie and I talked about going up to our room. We sat there for a bit, saying "goodnight" to everyone, then Howie and I headed up to the room. So in Jamaica, if you want pot, it's not hard to get. Howie and I aren't big smokers, but we do love to have a toke or two before we have sex. It just seems to make sex feel so much better and totally lowers my inhibitions. Howie had "made a local friend" the first day we got there and had bought some. As we walked in the room, Howie says, "I'm going to have a little toke. Would you like a puff?"

I was feeling kinda horny and honestly, I had pictured in my mind what Jake and Sandy would look like fucking after I caught her rubbing her husband's cock. So I said, "Sure. I'll have some."

We had an awesome deck that overlooked the ocean. As we're out there smoking, I said, "I caught Sandy rubbing on Jake's cock at the bar tonight."

As soon as I said that, Howie almost spit out his beer laughing and said, "Get the hell out of here! Are you kidding? I saw Max under the table run his hand up Erica's skirt, and with my point of view from where I was sitting it was clear she wasn't wearing panties underneath."

I started rolling. I couldn't believe we both saw both couples getting a little frisky with each other. Needless to say, it gave us something fun and sexy to talk about. Clearly, the talk was making Howie horny because I could see his cock getting hard under his boxers. "Looks like someone else is a little excited tonight too," as I gazed at his cock hardening underneath.

"Yeah, a little bit," Howie said in a slow sexy voice as he started rubbing my pussy under the bathrobe I had put on.

By now I had smoked and Howie was making my pussy feel really good rubbing and fingering me. I could feel the tingling sensation in my pussy as I started to get wet and my pussy lips started to swell up and get fat. "Let's go inside," I said.

"Well alright," he replied. I disrobed and climbed on the bed naked. "Get on all fours and face your ass to me," Howie said. The first thing I felt was Howie's warm wet tongue licking around the outside of my asshole. I fucking love when he licks my ass. It's another little dirty kink we both share. He loves to do it, and I love to feel it. As he's licking my ass and darting his tongue in and out of my asshole, he reaches around and starts to rub my clit. My pussy is soaked at this point. He pauses for a bit and I see him reaching for some lube. He lubes my asshole up and sticks his finger in my ass with his index finger and his thumb goes in my pussy. Again, I absolutely love to have both holes filled. Next I see Howie reach over by the nightstand and grabs a dildo. Yes, we travel with sex toys. I'm sure TSA loves our bags! Howie says, "Do you want a cock in your ass?"

I look back over my shoulder and nod aggressively, almost like I'm begging to be filled. I feel the dildo slowly slide in my ass and fill me up, as I think to myself, "God, I love cock in my ass." By now I'm ramped up and ready to cum. "I want to get on top of you now," I say, almost pleading for his cock. Howie lays down on his back and I mount his cock with the dildo still in my ass. As soon as my wet pussy slides down on his cock, I know I'm going to cum so fucking hard tonight.

Howie grabs my head and pulls me in and says slightly louder than a whisper, "I want you to think about having both your holes fucked and filled at Desires Island."

Instantly I take my mind there. Since it was fresh, I fantasized about Jake from the bar being the other guy filling me. I was close! I was gonna cum. "Oh my God, I'm gonna fucking cum," I shouted.

"Cum on me baby, cum all over me," Howie chanted. Moments later I let out a scream and had the most intense orgasm, cumming all over Howie's cock. Next Howie yells, "I'm cumming too, baby!" He lets out a moan of pleasure and I feel him explode inside of me, filling my already soaked pussy full of hot cum. I can literally feel the throbbing and pulsating of his cock as he empties a massive load of cum inside me. I collapse on him, both of us breathing heavy. Howie whispers in my ear again, "You're gonna love Desires."

Yes, I am, I thought to myself. We both share a sexy laugh together, cuddle for a bit, and then turn in for the night.

Our last day at The Sunset Palms was a super chill. We just hung out on the beach all day. The sun started to go down, so Howie and I got out of the water, went back to the room, got cleaned up, and came back down to eat at the restaurant on the property. After we ate, we agreed to have a few drinks at the bar and just call it an early night by chilling out on our ocean view patio for the evening in anticipation of our big day tomorrow packing up to leave for Desires. After we ate, we went to the bar next to the restaurant. And sure enough, who walks into the bar for some pre-dinner drinks? None other than Jake, Sandy, Max, and Erica. The ladies saw us first, and Erica said, "Hey Candy," from across the bar.

I replied back, "Hello!"

They came over by us and Sandy says, "Mind if we join you for a drink?"

"Of course not," I replied.

We were all having a drink together. The couples were talking amongst themselves for a second when Howie discreetly leans over and says to me, "They must have got ahold of the good weed too. They're high as hell. I can smell them, and they're all a little giggly."

I take note for a couple minutes of their behavior, look over at Howie, and kind of give him a nod like I notice too. It was nothing obnoxious. They were just having a good time in Jamaica! We only had a couple drinks with them before they went to dinner, but their mutual touching of each other was a little more noticeable tonight. Howie saw Jake rubbing on Sandy's ass. And I saw Erin run her hand over Max's cock a couple times. And they were just really touchy, feely in general. Again, not like totally obvious. But if you paid attention and watched close for a bit, you'd catch them.

They went to dinner. Howie and I went to the room. And we just relaxed on our patio with a few more beers, sharing the stories of the action we both saw during the day. Howie and I fucked again that night. It was that soft, slow sensual kind of sex. We both got off, then kissed goodnight, and slept like babies.

So we wake up the next day and Howie was like an excited kid on Christmas morning because today is the day we go to Desires Island. Me on the other hand, was experiencing some pre-game jitters, if you will. We ate breakfast. Hung out on the beach for about an hour. Then headed to the room to clean up, pack up, and check out of the hotel. Desires Island sent a shuttle to pick us up. It was only about a 15-minute drive to get to their dock. And I could feel my heart pounding a little faster as we got closer.

Howie was already thinking dirty thoughts as he was gently rubbing my legs and my pussy over my clothes. We get to the dock area where the driver drops us off in a parking lot. There's a walkway that takes you down to the dock where you board a water taxi to get to the island. There were four other couples at the dock waiting to ship off. The boat driver asks everyone to get in, so me, Howie, and the other couples all get in. I'm getting really nervous by now. The boat ride takes a little over 5-minutes to get over to the island. While we're riding over, I'm trying not to look at anyone, but my curiosity gets the best of me. I scan everyone in the boat. And to my surprise, everyone honestly is pretty normal looking. Most are attractive and fit. Some older than us, some younger. I'm sitting next to a lady. And I think she sensed my nervousness. "Is this your first time here," she said.

"Yes, it is," I shortly replied.

She got a big grin on her face and said, "You're going to love it here."

I could sense she was just merely trying to be kind. "You've been here before?" I asked.

"Yes," she replied quickly with a big smile, "we came here for the first time last year."

"Well, clearly you had fun if you're coming back," I commented back, as I started to feel a little more comfortable.

"We did. It was an amazing experience," she said, "I was super nervous about coming last year." I could tell she was trying to put my mind at ease. "Just relax, have fun, and do what feels right," she confidently said, "No one is pushy here. There are no expectations. Some couples just watch and do their own thing. And some couples immerse themselves and get real friendly."