Relationship Timeline | Post #8 | Hawaii Vacation and Roleplay

Shortly after James returned from California, we went on our first big vacation together. We had been on short overnights (like the one in this blog post), but not a real vacation.

It was spring of 2021 and we had a gorgeous resort booked on the island of Kauai in Hawaii. We were super excited to finally have a vacation together. Between him being in California for 9 months and the pandemic, we were so ready for a real vacation.

We had an incredible ocean view room with a balcony, and we were ready for pool time and LOTS of great vacation sex.

As you may know if you’ve been following us for a while, we love to roleplay and we’re always thinking of new scenarios and sharing them with each other. So, we came up with one for this vacation that turned us both on and we did it. It was insanely hot.

What I’m about to share with you for the rest of this blog is the erotica version of the roleplay that really happened that night in Hawaii. I’m writing it from the perspective of the woman in the roleplay along with the setup we talked about before the roleplay started. I hope you enjoy.

After a short but eventful foray into the world of marriage, I found myself divorced, about to turn 40, and restless. I’d pretty much always been in some type of relationship for the last 20 years. I was essentially afraid not to be in a relationship. Something was different now, though. I was ready to focus on myself. To be independent. To be ok not being in a relationship.

But first, I was going on a vacation to Hawaii. All by myself. I’d never been to Hawaii and I’d certainly never been on a vacation like this by myself. We had it booked before we decided to get divorced and I decided to just go on the vacation anyway. I had an ocean view room with a balcony, I flew first class, and I went!

I could hardly believe it when I got to the hotel. Right there on the perfect little crescent shaped beach on the island of Kauai was this picturesque resort. It was literally like a postcard come to life.

As if things weren’t already going well, as I walked up to check-in there was an attractive man in line just in front of me. A little eye candy to go with the beautiful resort? Yes please! He was just my type with a sturdy build, great hair, and a sort of genuine look to him. I caught myself imagining a little vacation fun with him when I was called up to the check-in counter and my little daydream was cut short.

Even at the time, it seemed to be a bit too good to be true. All of it, really. But, I had actually been thinking about trying to be a bit wilder than my usual self on this vacation. I told myself I was going to try to meet people and have fun and not just sit by myself and read by the pool (although I was definitely going to do that too). I certainly wanted to meet at least one person at this resort now, that was for sure. Haha.

Anyway, I wasted no time enjoying the resort. I went to the pool almost right away, and then spent the early evening watching the sun go down from my balcony. It was amazing.

And then it happened. Just after sunset, I saw the guy from check-in walking out toward one of the main terraces overlooking the pool. I watched as he sat in a lounge chair by himself. He was just sitting there looking out toward the pool and the beach.

Was this the sign I needed? I decided that it was indeed. So, I changed into one of my favorite dresses (see below) and decided I was going to go sit by him and see if I could chat him up. I had no plans (uh…ok..maybe a little bit of a plan) or expectations. I just decided I was going to be bold and initiate a conversation.

So, I walked right over to him in my low cut dress and asked if I could sit next to him. He said yes and we made some small talk about the sunset and the resort and the pool. Then, I asked him if he was here by himself and he proceeded to tell me that he just got divorced and he was on a vacation by himself that was supposed to originally be with his wife. We literally had the same exact story.

As you can imagine, the conversation flowed quite nicely after that. We talked about everything from our past relationships to our current goals and plans. And, although that was fun, less than 10 minutes into the conversation I was absolutely dying to take him back to my room. He was clearly feeling the same way. We’d both often stop talking between sentences and just stare at each other for a quick second. I felt like we both knew where this was going.
So, I pulled together that adventurous and wild version of me that I mentioned earlier and just asked him back to my room. He said yes immediately, and we headed to my room.

I poured some wine in the room and we went out on the balcony to see the view for a minute, but I didn’t want to waste any more time. I was really wanting to maintain the pursuer position because I had never really been in that position. So, I saw an opportunity and I initiated a kiss on the balcony. He was a bit startled at first, as if he didn’t expect me to initiate, but he settled into it nicely. Oh, and what an amazing kiss it was. His hand lightly held the side of my face as we kissed. Meanwhile, my hands reached back and undid the top of my dress. I brought the top of the dress down, exposing my breasts, and moved his other hand up from my waist to let him know I wanted him to touch. I could feel his cock get hard up against me as soon as he started touching my nipples.

The kissing got heavier and heavier until we decided it was time to move things in from the balcony. We stumbled our way in through the sliding glass door while unbuttoning clothing and trying to continue kissing.

He moved me toward the bed as we kissed and removed my dress the rest of the way. I had a feeling I knew what he was thinking, and I was so right. He pushed me back onto the bed and began slowly kissing from my right knee down my inner thigh. He was intentional. I knew exactly where he was heading but I had no idea how long it would take him to get there. So much for maintaining the power pursuer position, but I did not care at this point. I was in heaven.

When he got all the way down my inner thigh, he brushed his nose lightly across my panties right near my clit and then kept going over to my other leg. I let out a loud sort of wimper as the sensation was incredible. The anticipation was getting me so wet. My panties were soaked through already. Meanwhile, he was slowly and deliberately kissing up my left inner thigh. The best torture.

When he got to my left knee, he put my legs together and removed my soaked panties. Then, he did the exact same thing again. Starting from my right knee, kissing down my inner thigh, brushing his nose lightly across my bare clit this time and sending my hips into the air and causing another loud exclamation of pleasure.

I guess he decided that he had accomplished his goal after that sound because he finally let that tongue get to work on my pussy and clit. He had a way of perfectly balancing the amount of clit attention I need. He would spend some time licking my clit and then give it a little rest while he tongue fucked me. Then, at what seemed like the exact right time, he would very slowly lick up toward the clit creating extreme anticipation before finally licking it vigorously.

I am 100% sure he could have made me cum like this if I would have let him, but in true form, I needed his cock before that. So, I asked him to bring his cock to me. He crawled up on the bed and brought his cock right to my mouth.

I was still laying down on the bed and he was on his knees next to me. From this position, he could reach my pussy while I sucked his cock. He played with my clit and slid his fingers in and out of my pussy while I had my fun for a while. He was so hard in my mouth. I don’t think I have ever felt a cock that hard. I had to feel it inside me.

I told him to lay down on the bed and I quickly climbed on top of him and put his face right between my small breasts. I felt his cock pulsing against my pussy as he enjoyed being pressed against my chest. He pushed me back just a bit so he could move over to one of my nipples. I knew he was wanting to suck on them from the moment he saw them out on the balcony.

As he went back and forth playing with my nipples with his tongue, I was slowly grinding my dripping wet pussy on his cock. Then I reached behind me, grabbed his cock and started rubbing the tip all over the edges of my pussy. Sometimes I would let the tip go in just an inch or so and he would physically brace as though he expected me to take it all in, but then I would tease him some more. This was my delicious payback for the torture he had just given me.

I held out as long as I could, enjoying every facial expression he made as I teased the tip of his cock over and over again. But, eventually, I couldn’t stand it any longer either and I needed to feel that rock hard cock all the way inside of me. So, I looked into his eyes and asked, “are you ready?” He nodded with his mouth wide open in anticipation of the feeling of my pussy sliding all the way down his cock. I put just the tip in again and asked, “are you sure you’re ready?” He nodded faster and with more enthusiasm this time and I watched his face as I gave us both what we wanted. His face was so expressive. I knew exactly how much he enjoyed it.

I put my hands on his chest and began rocking my hips back and forth with his cock all the way inside me. He matched my hip motions perfectly with short thrusts. As my hips would roll forward, he would come out just a bit, and as my hips rolled back, he would add a little thrust to get a bit deeper inside me. It was pure heaven. We stayed slow like this for a little while. Looking into each other’s eyes and enjoying the sensation of being so deep.

I remember thinking at this point that we needed to change up the tempo and it was like he read my mind. He grabbed me and pulled me down on top of him, wrapped his arms tightly around my back so I couldn’t move, and began fucking me vigorously. I tried to sit up just to see how strong he was and I literally could not move more than an inch. Fuck, that really turned me on. I was moaning like crazy as he fucked me and I could feel myself getting closer and closer to orgasm. At the time, I had hardly ever had an orgasm during normal sex before and was a little shy about it, but I basically had no choice. My body was heading toward orgasm and I couldn’t stop the sounds I was making or the way I was grabbing the back of his neck and biting his shoulder as he fucked me.

As I reached orgasm, I let out a completely untamed sound that most certainly was heard throughout the entire hotel floor and half of the resort (we hadn’t closed the balcony door even). As I finished yelling, my body relaxed and I collapsed on top of him. He slowed his rhythm and kissed my neck as he let me enjoy the aftermath of one of the best orgasms of my life.

When I recovered, I looked at him as if to say “wow, that was amazing”, and then asked him what he wanted. He asked if he could fuck me from behind and I enthusiastically agreed. He said he was already very close to orgasm, so we quickly got into position and he slid his cock all the way in. He made a sound as he slid in as if to say, “this isn’t going to take long”. He was right.

He started with a slow rhythm, reaching up to caress my boobs as he fucked me. As he got closer to cumming, he increased his speed, grabbing my hips for leverage. He fucked me faster and harder until I realized that I was close to a second orgasm. “You’re going to make me cum again”, I said to him in disbelief. He grabbed my hips harder and increased his pace again. I felt his orgasm building inside me until we both screamed out at the same time. He came so hard inside me and it sent me over the edge to my second orgasm of the night.

We collapsed together on the bed with my head resting on his shoulder and we just stared at the ceiling breathing heavily for what seemed like forever. We didn’t say a word.

Then, he got up and put his clothes back on, gave me a good night kiss, and went back to his room. He came over a few more times during that vacation and we had incredible sex. At the end of the trip, we met to say goodbye and I’ve never seen him again. We both agreed that was best. What a vacation.