Hi guys! It’s been a while since I posted, and for that I apologize. I’ve been rather busy lately and traveling a lot with my job. My last post kind of left people hanging as it was part 1 of 2, but I haven’t been motivated to finish that one yet. This story is not one from my ancient history, but as recent as this week. As always, a true story where only the names, ages, and some specifics are changed to protect the innocent. 😏 (Or the guilty.)
So I had to travel to one of the military bases on Oahu in Hawaii for a painful planning conference this week. Five days of sitting in a security vault pouring over documents related to what I do. The days sucked, just me and one other guy (another civilian about 10 years older than me with no personality or sense of humor). He was something out of a black-and-white police movie from the 50s. Who the heck wears a suit in Hawaii??? But, I digress… The whole week felt like an interrogation, even though I was sent here to help HIM unfuck one of HIS programs.
I arrived last weekend having left Tokyo at 13:00 on the Japanese Saturday and arriving in Honolulu at 10:30 on the Hawaiian Saturday. Yes, I technically travelled back in time (reference Einstein and his theory that time is relative). That said, I still had almost a whole day ahead of me to spend on the island. I picked-up my rental car and went for a drive since I couldn’t check-in until 15:00. I drove from HNL to the H-1, around the southern tip, stopping at the Halona Blowhole, then Makapu’u Light, then through Kailua and Kaneohe on my way to the North Shore. I stopped at a shrimp truck and devoured a serving of Tiger Shrimp before driving to Hale’Iwa. Somewhere along the drive something reminded me to reactivate my Tindr account. It doesn’t work in Japan so I always delete it. Even in the United States I’ve never had any luck except for the one time a woman matched with me, but after we met decided she liked my travel buddy more than me and hooked up with him instead. I got to spend the night in our shared hotel room flipping thru the hotel channels while he railed her in the bed next to mine. Good times. 🙄
The drive was as beautiful as I remembered it to be. After passing through Hale’Iwa I jumped on the H-2 near Schofield Barracks and shot down the highway to get back on the H-1. Not quite a total circumnavigation of the island, but it was getting close to check-in time and I wanted to get unpacked and get a shower.
It was somewhere around Hale’Iwa when I received a message asking, “Where are your pictures?” No Hello, no other quick or witty salutation, nothing. I replied with something like, “I am fine, thank you for asking. How about you?” While this was happening I surfed her photos and liked what I saw. She was an Asian girl with long dark hair, beautiful eyes and a sexy mouth. Some of her photos were action shots taken on hikes through a desert, and another in a forest. Others were in frilly dresses with big floppy hats. I definitely liked what I saw. She has amazing eyes, great facial structure, and these sexy lips that make you want to bite them.
After another couple awkward exchanges I expected her to unmatch with me, but the conversation picked up. She asked again for a face photo, and I sent it. She didn’t comment on the photo, but instead mentioned that she was thinking about attending a Waikiki street festival that evening. I asked her if she was going to be with anyone and she replied that the object of her affection had blown her off and she was looking to work out her frustrations. As it turned out my hotel was near the festival so I told her that I might attend and would let her know. She never really asked me to go, and didn’t comment good or bad on my photo, so I figured the conversation was not leading anywhere. A bit later she pinged me again, “Are you going?” I said that I might and she replied with the directions. The rest of the drive was spent with small talk; why she was here, what type of Asian is she, what her vacation plans were, etc. I guessed that she was Japanese, I was wrong, she is Filipina. She mentioned that most people accuse her off being Mexican, that she is a SCUBA diver, and likes to hike. You know, small talk. The Filipina thing really works for me. While I have only dated one in the past I have always been enamored with their natural beauty and the Filipino culture as a whole. How lucky I was to have matched with her!
I got to my hotel about 30 minutes after the festival started, caught a quick shower, and changed into the appropriate Aloha attire and checked Tindr. She had sent a text asking if I was coming and I replied that I was on my way. We met up at one of the sales tents where she was looking at jewelry. She was as pretty in person as she was in her photos. We awkwardly hugged and said Hello! We started chatting a bit and quickly agreed that we needed to get something to eat and drink. We walked back down Kalakaua Ave and found a Hard Rock Restaurant and put our name on the list we chatted some more and looked around the store. We were getting along pretty well. The conversation came natural and wasn’t forced.
At some point I asked her again why she was in Honolulu alone. She mentioned that she had flown out to see an old flame who once lived where she lives. They had maintained a long-distance kind of thing and were supposed to reconnect this week. However, after a couple of meet-ups he started finding excuses to not see her. She had come to the conclusion that he was seeing someone else and wasn’t quite man enough to tell her. Thus, her need to have some fun now that the rest of her trip was going to be solo.
We had a drink and ate some nachos and enjoyed each other’s company. After about an hour she asked how far my hotel was, to which I replied that it was only a few blocks. In fact it was only another two blocks to her hotel, so that put my place almost halfway between the Hard Rock and where she was staying. She said that she was ready to go, so I paid the tab, we grabbed each other’s hands and walked to my hotel. The elevator ride was quiet. We stood next together occasionally stealing a glance and a smile. We got to my door and no sooner had it shut behind us, she grabbed my face and pulled my lips to hers. She is a very aggressive kisser when she initiates the activity; but as I found out later and throughout the week, when I initiate the kiss she’s very coy and very gentle. After maybe a minute of passionate kisses she fell back on the bed and pulled me down on top of her. We spent a few more minutes kissing and grinding before we started to pull at each other’s clothes. She was wearing a white frilly dress and a pair tiny black lace panties underneath. After she took them off and flung them across the room I immediately saw the opportunity to go down on her freshly waxed, and very wet pussy. I love licking a woman and she was very responsive. I must have been doing something right, or she was so darn horny that it didn’t matter. Either way she was moaning and squirming and squeezing my head with her legs. I pulled back and started to finger her; first with one, then two fingers. She reached down and began playing with her clit and soon had her first orgasm before I even inserted my penis.
After she came we rested a bit. We actually cuddled and snuggled like we were a real couple, and not a couple of internet RandOs looking for a quick release. It could have been 3 minutes, or 30, but I asked if she was ready to go again and she said, “Yes!” I rolled over and put on a condom. I started to finger her and kiss her again and she was still very wet. I climbed between her legs and started kissing her and playing with her boobs. She grabbed my cock and started rubbing it up snd down her slit, then positioned it at her entrance. I slowly started to push and as I broke in for the first inch, her body shuddered and she let out a moan. Slowly still, inch by inch, I pushed all the way until I thought I felt her cervix. The depth of her pussy is exactly the length of my cock. Once there I held it for a few seconds while she grabbed my back and held me as our tongues danced between our lips. I could feel her wetness drip down the base of my penis and onto my balls. Slowly at first I started to thrust in and out, then faster. It wasn’t long before I had her legs up against my chest with her ankles over my shoulders as I furiously pounded her pussy.
Then, it happened. I came. Damn condom, happens every time!!! The thing puts additional pressure on the base of my cock and I react to that specific stimuli every time and I cum quick. I apologized, but she didn’t seem to mind. (I’m sure she was being kind.) We were both breathing very heavily and she already got one nut before I did. I laid down beside her and we started kissing gently, then forcefully, then gently again. She rolled over on her left side and I kind of spooned her and rubbed her back, her neck, and played with her boobs from behind.
We drifted off to sleep for maybe an hour when one or the other of us woke up and started kissing the other (probably me). It took all of 2.3 seconds to be rock hard again so I slipped between her legs and we started round 2. Again, slowly at first so she could feel every bit of me enter her. This time was very much like the first time. Slowly, then vigorously. Legs up, legs pinned to the side, missionary. We probably went another half hour before I was spent. We laid next to each other and cuddled again, this time comfortably under the covers. We kissed, and felt each other’s bodies with our hands, kissed some more and tried to sleep.
After a couple of hours I felt her roll from her side to her back. Then a few minutes later she rolled again onto her side facing me. Then, I felt her face lift up to mine so I took the opportunity to kiss her. She warmly received it and grabbed my face. Time for round three. Again, another vigorous 30 minutes do so before we agreed that we both had long days ahead of us. I had a plan for my day, and she had a SCUBA dive to catch. She quickly showered, redressed, and kissed me goodbye begore she left. I told her that if she wasn’t disappointed with our first night, I’d be available for a second.
The day went by. She completed her dive and shot me selfie. Things were looking positive. At some point she asked if I wanted to hang out again. I asked her if she wanted dinner. We met up and I gave her a historical tour of some of the WWII sights on Oahu and proceeded to a beach bar where she had shrimp and I had a Kahlua Pork French Dip. After dinner we took a walk along a seawall and whenwe got to the furthest point from the resto, i backed her up against the wall and we made out, kissing and touchingband grabbing each other like teenagers. We calmed down and headed back to the hotel and she came up with me again.
Sure enough, just as the night prior she grabbed my face and pulled me into her and kissed me very aggressively. I cannot put into words how insanely hot this is! I am all about being the initiator, but in this day and age it’s quite nice to have a woman put it on you first.
This night went very much like the first. Three rounds of furious sex, each followed by an hour or two of sleep, before the next round started. Once again, an early day, except now I had to be the one to get up early to go to Day 1 of my conference. Before she left we had breakfast together in the hotel restaurant. Or maybe that was Sunday morning? 🤔 (Whichever day it was, it was nice.) Again, I told her that the rest of her trip was her call. If I impressed her enough the night prior (or if she pitied me enough) I’d take her to dinner again that night. We parted in the lobby and went our seperate ways. She met a friend that she made on the beach and the two of them went on a hike to the Kailua Pillbox.
Later that afternoon, she sent me another selfie. Again, good news. We planned to get together again for dinner and a drink. We walked around Waikiki a little bit only to be disappointed that everything closes early now, post pandemic. We did get a late start, but restaurants and bars close at 8pm now. WTF? We ended up walking to The Barefoot Bar on the beach on the Hale Koa military compound which runs a 5 Star resort for military and veterans. We had a couple of drinks, but no dinner, and talked about our days, our lives, and football. After her second drink she asked if I was ready to go. This was now our third night together in 3 days and I felt relatively secure in that I knew what was on her mind. We left the bar and headed towards my hotel, hand in hand.
Again, once in the room we clawed at each other for a few minutes. This time we broke free just long enough to take quick showers and rinse off the day before getting all sweaty and dirty again. Things processed in much the same way as it did the nights prior; slow sex, vigorous sex, sweet sex, angry sex… then an hour or two of sleep before a midnight boner starts the process all over again. By now, and on the third night, we set a pattern. Sex as soon as we got home that lasted about an hour inclusive of foreplay, a couple hours rest, another 30 or 40 minutes, a couple hours rest, then we wake up and meet the day with a heart pumping session just before showers and a kiss goodbye for the day.
A man could become addicted to this routine. I’m just sayin’…
So, we’re now on our fourth day. On the morrow she leaves to go home. She’s a nurse and has grown up responsibilities that she has to return to. We both knew this was going to be the last day of our Island Fling. Again, she texted asking if I wanted to hang out. Again, I jumped at the chance. By this time we’d not only gotten along well sexually, but from my perspective we were becoming friends. I looked forward to spending the time with her doing date night kinds of things before we retired to the hotel bed. That said, this night was a little frustrating in that I had a grand plan to take her to this little Italian joint on the other side of the island. I checked their website and it said they closed at 20:00, but when we got there at 18:45 the sign on the wall said they closed st 19:00. We stood at the desk literally being ignored. After a few minutes I walked back to the service station to see if we could get a table and was told they had closed even earlier. I was a little pissed, but whatever, we’ll just go to the next town over and see what’s up over there.
As it turns out, nothing. We stopped by two Mexican joints, an Indian Curry place and passed multiple restaurants in the car only to see them all closed by 7pm. WTF… We finally found a Maui Beer Company that was still open an slipped in by 19:45. We sat at the bar and ordered a couple of beers and a really good mango and prosciutto pizza. We talked and exchanged sweet little kisses while we half heartedly watched some surfing and San Diego Padres baseball while we enjoyed the beer and pizza. At some point she started feeling frisky, and much like at the seawall a couple nights prior, started to get handsy. I asked her if she was ready to go and her eyes lit up and she said, “Yes!”
We got in the car and started to head back to Waikiki. At one stoplight she started the show by grabbing my face and pulling it to hers with one of her signature aggressively placed kisses. I immediately got rock hard. A few miles down the road we pulled over so I could show her this giant Japanese pagoda. I had a sneaky plan to bang her on that wall with the pagoda in view, however there was a local guy also parked there taking a water bottle shower next to his truck. Not the vibe I was going for.
We got back to the hotel, took quick showers and got naked. We both knew it was our last night together, probably forever. That said, I don’t think either of us felt any real pressure. We just continued to enjoy each other as if tomorrow would never come. The routine began anew. Session one, sleep, session two, sleep, then session three. This time was a little different in that we finished with anal (her’s, not mine). The night prior we had discussed likes and dislikes and she mentioned that she loves to feel her man cum in her, and then the afterglow of feeling it leak out and drip down her legs. Well, I hadn’t cum in her pussy so she didn’t experience that with me. She said that she’s not on birth control at our first meeting, and as such I avoided cumming in her and pulled out well before. However the conversation turned when she mentioned that she did like to feel men cum in her ass, that it was a very similar sensation. She could feel the cock throb, then ejaculate inside and spew hot warm liquid inside her body. Then, leak out later.
So during our last session of our last night I asked her if she wanted to try anal and she said, “Yes!” She was already on her belly because we were hitting it from behind. I withdrew from her pussy and traced my tongue down her neck, her back, down the Crack of her ass and finally to her brownie. I licked her there and began to massage her ass, first with my thumb, then with a finger. She raised her hips a little bit and pushed her ass back into my fingers. I reached over to the bedstand and picked up a bottle of lube and applied a generous amount to her ass and my finger. I slowly worked it into her firey hot, tight ass. In and out with just one finger at first, then two. After she was sufficiently lubricated I moved in behind her and pressed the tip of my cock to her opening and gently slid it in. She let out a loud moan and grabbed the bedsheets. Just as with her pussy, I entered her slowly, one centimeter at a time until I was pressed firmly against her buttcheeks. After holding there a minute I started to stroke in and out very slowly, eventually building up to a nice quick rhythm, to which she met by rocking her hips. Her ass felt like a velvet glove, not unlike the silky wetness of her pussy, but definitely a little different. Before I could cum she mentioned that she was getting sore, and I can understand why. By the end we were ficking almost as vigorously as we were earlier. I slowly withdrew and layed down next to her.
We cuddled and kissed for a while before she made the adult call to stop so we could get ready and begin our days. She had ro be at the airport in a few hoursvand still needed go back to her hotel, pack abd get on the road for the airport. She took a quick shower and dressed. I showered while she dried her hair. Then it was time. We said our goodbyes, kissed each other softly and she left.
What a great week full of great memories! I hope we meet up again in the future. We agreed to keep in contact, so who knows???
Source: reddit.com/r/gonewildstories/comments/xmoy0e/my_island_fling_52m37f_hawaii