My Hawaii Trip

This is a true story. At least from what I remember. My recollections and fantasies may have embellished it over the twenty years or so, but I believe I am describing the images as they occurred…

I was on my way to Hawaii, flying from the East Coast. I was planning on meeting a group of friends there. All of us had gone to high school three years before, and we were on summer break from various colleges we were attending.

I was happy to see my dozen or so friends, but I was concerned that it might be a drunken party, a Spring Break, but in the summer. I had since lost interest in drinking to enjoy myself, and never really drank that much compared to my friends.

I recently broke up with my girlfriend. Well, she dumped me, but I was rather relieved as I did not know how to handle or end our relationship. I enjoyed her, but did not feel it was going anywhere. I was ready for something new.

The flight from the Chicago to Honolulu after a short hop from Pittsburg was long, and I was fortunate to be sitting next to a cute girl about my age. A girl-next-door, but athletic looking, brownish-blond hair. My first thought when I saw her was of the Spring-break mindset: “I hope score with her… lift up your shirt and show me your breasts…want to join the mile high club…would you mind kissing that flight attendant while I watch and fondle you both, then we both go in the back of the plane…” You know, the normal things a guy thinks when he sees a cute girl.

But, I was glad nothing stupid came out of my mouth, and realizing how ridiculous and insensitive my thoughts were, I smiled at her like she was a human being instead of a drunken Spring break slut, and said, “Hi”. She smiled back.

As the flight took off, my mind wandered about the school year, how I had one more year left, what my friends are like now, what to do in Hawaii outside of the hotel, and many other daydreams. Sometimes a long flight is needed just to force you to face your thoughts.

My clean, non-sexual daydreams were interrupted by a sweet voice next to me. I quickly responded by controlling my mind to quell any sexual arousal and subsequent runaway thoughts that occurred earlier just from looking at her.

She asked why I was going to Hawaii. I told her why and asked the same. She told me she was meeting two other friends who lived there. She in Hawaii as a young teenager and would be vacationing with two childhood friends on the North Shore of O’ahu, in her uncle’s house who was out of the country.

We talked about seeing our friends, what it would be like, how much we enjoyed Hawaii before, our colleges and other things. I don’t really recall all the subjects, as my daydreams melded into our conversation. It was about an hour before we actually introduced ourselves by name. Her name (for purposes of this story) was Nancy.

My mind began to move back to sex, as she told me about her first year in college, I began to want her, to kiss her while she was telling me her story, to reach over and cup her small breasts, to move close to her, and just continue from there the whole ten days in Hawaii…just as I was trying to stop my wandering mind again, she told me about her boyfriend who was supposed to meet her at her uncle’s house in Hawaii.

Great. I needed that. Back to treating her like a person.

We talked, napped, daydreamed for the next six hours. After being awakened by the pilot starting the descent to Honolulu Airport, Nancy started talking about where I was staying and that her friends could give me a ride. I accepted, and thanked her, but wanted to make sure it was OK with her friends first.

After landing, I met her friends while being picked up. Karen was a part-Japanese girl, with a typical petite Asian body, and nice buns, who spent her whole life in Hawaii living in Kahuku. Janet was a haole who looked like a typical North Shore surfer with bleached blond hair. Like Nancy, she too was athletic, but with a cute small layer of tummy fat just above her surf shorts to compliment her medium large breasts. I thought I have to stop thinking like that. These girls have eyes and faces.

They were nice and gracious. At the hotel, I thanked them for the ride, and told them how nice it was to meet them. As we were unloading our bags from the car, I was greeted by one of my friends, Tom. I introduced everyone, and was thankful that Tom did not act like a drunken guy trying to score. I was able to keep my thoughts clean enough, and hoped my friend would too. I wished them a happy vacation, and said maybe we can see each other on a flight some other time.

Karen went to the other side of the car, said something to Janet, and then Janet invited Tom and I both to visit them on the North Shore sometime this week. I gave her the hotel number and Tom gave her the room number that three of us guys would be staying. The other nine or so friends were on the same floor.

I caught up with my friends, was happy to see them, but turned in early as I was still on East Coast time.

I was surprised the next day when Nancy called and said they were picking us up. They also told us to bring some extra clothes in because of the beach. We packed up and went, enjoying the hour ride to the North Shore. I was surprised Tom and I weren’t acting like jerks; although both of our thoughts went there I am sure. I told Tom that these girls want to have a good time, but not in the Spring break way. Wow, I thought, we have matured.

Her uncle’s house was a simple house with lots of windows, breezes, and wooden porch with a starving surfer’s flare. We hung out there for a while, went to the beach and enjoyed that, although I was a little disappointed in how much the girl’s bathing suits covered. Both Janet and Nancy were surfing, with surfing shirts on, alternating with their board. We just had a good time.

We went back to the house, and took turns taking showers. I thought, “It would save water if we doubled up on showers,” but again, I didn’t say anything. You see, at the beach Nancy talked about her boyfriend, Karen talked about her boyfriend and how she was expected to marry him ever since she was 13. They liked each other, and he was a friend of the family, and her father, a minister wanted to make sure she and everyone married properly. It seemed like I might have shot with Janet, until she told me she has learned to hate boyfriends after her last three were lying to her. She looked me straight in the eye and said it, and I knew she was really saying, “Don’t even think about it.”

We had a plate lunch dinner and talked about heading back, but they offered to have us spend the night, being very clear about the sleeping arrangements in the three bedrooms and couch. I wondered if they were teasing us, seducing us, driving us crazy, or just being good hosts. I got so many indications from them that they did not want to be touched. And for some reason, that was OK with me, and it seemed OK with Tom.

Both Nancy and I were still feeling jet lagged and started to doze off while the other three were enjoying each others company. Because I was tired first, I got the bedroom and Tom got the sofa. Karen had her own room and Janet and Nancy shared a room.

Nancy and I both went to our rooms. I fell asleep almost as soon as I pulled the covers over me. I don’t know how long it was, but I awoke to some noise in the other room. It was quiet moaning, heavy breathing, a little creaking of furniture. “No way,” I thought, “Tom scored??!!!” I was reading these women wrong, or at least one. I couldn’t help but to sneak quietly out of my room and look, not because of the turn-on of watching them have sex, but to see who Tom was doing. I peaked out of my room, looked hard in the dark, made out moving legs, arms, hips, not making out whose parts they were. I was not turned on, because I did not want to be enjoying the vision of a nice pair of buns, only to find out it was Tom’s. Hey, I did not want any inkling that I could remotely possibly be gay. Eventually, as my eyes adjusted and the moon moved away from the clouds I could make out Karen’s slender legs and tight Asian rear as she eased herself down on my friend. I enjoyed the sight of her body, as much as I could see. Wow, Karen who will marry the family friend, a minister’s daughter, screwing my friend on the first night there. It didn’t seem fair. I made the contact to get us here.

As I thought about sneaking back to my bed, with throbbing hard-on, wondering how I could explain the stains on the sheets if I jacked off, but feeling I had little choice, I looked up. Across the living room, staring at me from the other room was Nancy. She was enjoying the view, and apparently enjoying me watching. I was shocked, and embarrassed, but that was fleeting, as she opened the door slowly revealing her body, as she dropped her bathrobe with flower patterns onto the floor. Oh those breasts that I wanted to squeeze on the plane were just staring at me. Oh man, how do I get over there without being seen? And is Janet in her room?

I opened the door and looked out to check out a path when Nancy held up her hand. She would come over to me. I guess Janet was in her room. She ducked down, put her bathrobe back on, and slowly crawled out of her room, away from the sofa, and toward the kitchen keeping an eye on the sofa, hoping Tom would completely satisfy Karen, and continue it for at least a five more minutes.

Moaning, heaving breathing, sneaking, crawling, and I standing there not being able to do anything. “Don’t get caught, Nancy,” I thought, I am going to explode. Slowly she made it to my room stayed down, and crawled onto a throw rug on the bedroom floor. I was on top of her as soon as I closed the door, kissing her. I was surprised at how forceful her tongue went into my mouth, licking my lips, and kissing me up and down my neck. I could hardly stand it. I just wanted to shove myself in her, but I wanted to make this last long, because who knows if we would get a second chance. I kissed her all over up and down her neck, enjoying her scent as I nuzzled her neck and ears, and shoving my tongue way back in her mouth as she swallowed it up like it was my cock. I rubbed my hips against her and she opened her legs, and trapped my left legged between hers. She began thrusting and rubbing her hips on my leg. I could feel her wetness.

I kissed her up and down her neck, her arms, and worked my way to her small breasts. Her breasts were firm and her nipples very hard as I sucked and tongued them to her responsive moans. She grabbed the back of my head and pushed my face in her breasts. Their size said to me, “I don’t want my breast size to overshadow my nipples. My nipples are what deserve the attention.” And I attended to them.

I wanted to take her, but wanted to savor this. I lingered on her breasts, enjoyed her smell, as it mixed with the mustiness of her excited pussy, mmmmm….I can’t wait to taste that…

I kissed her belly moving down on her. She seemed disappointed as she did not have a leg to hump, but she knew my tongue was coming.

As soon as I got over her pussy, kissing her mound, she grabbed the back of my head, arched her back forward, and as if she was kissing me with her pussy, put her lips against mine, as I gently licked her from top to bottom of her slit. It was so wet, so soft, so swollen. Her wetness was all over as I felt it on my cheeks and chin. I moved up and down slowly, rhythmically, she quivered, moaned, moved, pulled back, and pushed forward with my tongue way up insider her as far as I could go and my lips against her lips. Mmmmm…tastes as good as she smells….I quivered my tongue and lips for her, and she jerked her legs straight and pushed against may face as she came, quivering, shuddering repeatedly. I couldn’t tell if it was one orgasm or a series of five or six, as she kept repeating her thrusts and moans.

She pushed my face away and rolled her hips around and whispered “Stick it in me.” I remembered our friends in the other room and wondered if she was too loud, but I heard them screwing away, hmmmm….I could make some noise, believe me I wanted too. I eased my dick in her. I could feel my heartbeat throbbing in my dick. She moaned, moved her hips around, and with a gasp pulled me into her deeply and came again. I eased in and out, and pumped and breathed deep trying to hang on, and she leaned her hips way back, knees almost to her chest and legs only slightly bent, she was wide open for me and I let loose, all my desires from the time I saw her until now filling her up with my juices.

I almost passed out, lying on top of her as we both recovered steadying our breathing. We got up after about fifteen minutes, crawled into bed together naked as my hands ran along her body over all the parts I missed earlier, hips, thighs, ass, back, mmmm nice ass…as we slowly drifted off to sleep.

I woke up alone. Did I dream that encounter? She must have sneaked away, so her friends wouldn’t know. I hope it wasn’t a dream. I woke up with a hard-on and saw some tell-tale signs of our sex. Gladly it was not a dream.

I heard the shower running. There must have been three showers before I hopped in. We all had breakfast together and talked about how well we slept. No one talked about the four of us having sex. Although I could imaging poor Janet hearing all of this, seeing her roommate leaving, and masturbating herself to sleep. She was smiling and her complexion looked rosier than the day before. Maybe we were all satisfied.

That was only beginning my third day in Hawaii. I was hoping the week would continue as good as it started. It did, with many more surprises starting just later that afternoon.

End of part one.