The Trip

Story Info
Trip to Hawaii with my former supervisor (F).
2.9k words
4.02
40.5k
7
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Our plane landed in the late afternoon on the island of Oahu. The long flight in no way decreased the excitement for our visiting the Hawaiian Islands for the first time. I read a lot about this archipelago in school. Sharon has never been there before either and is looking forward to the trip. To be honest, during the flight I was thinking a little about what this is going to be like, taking a vacation with my former boss. But, we talked about it and I think everything is going to be alright. The platonic line is firmly entrenched. There is too much to do and see, anyway, to worry about everything else. I received such a great deal on this trip; there was a very low airfare, so, I arranged to stay in very respectable places on the three islands we're visiting.

Sharon and I walked out of our gate and immediately felt the warm semi-tropical air hit us. We got our bags and easily found the rental car stand. We climbed into our blue Mustang, drove it out of there and on to the hotel. Driving a Mustang is not my first choice, with my long legs and all. But who's going to argue with a woman like Sharon? Our hotel was directly across the street from Waikiki Beach. Hence the name, Waikiki Beach Hotel. The weather was perfect. Eighty degrees and partly cloudy, with a slight breeze. The room has obviously seen better days, but the view was just awesome. It couldn't have been more perfect. As the sun was on its way down, a jet could be seen spearing it's circumference on its way up, and a U.S. Navy ship was out to sea.

Sharon and I freshened up, changed clothes and went out to join the people. It was magnetizing. During our walk down the streets and through some of the outdoor shops, it was tempting, at first, to buy the merchandise being sold. But we resisted those urges, knowing there will be other, better, opportunities to buy things. We found a very nice restaurant a few blocks from our hotel. Tables were placed inside and out, with a great breeze flowing throughout. We sat at a table just inside the premises, but were exposed to the fresh air. I ordered blackened Mahi Mahi and Sharon tried their red snapper. And, of course, both of us had a daiquiri to start the trip off right. I don't count the horrible Mai Tai I had during the flight. The food was unbelievably delicious. Atmosphere so relaxing. The conversation varied throughout the dinner. We talked about everything from our annoying flight attendant, to my military experiences, college life, etc. Sharon is a very smart woman. I've always envied and admired her focus and determination. I do not regret my life-filled experiences; just envy a person with such focus. The night air was so beautiful. We went for another walk, then back to the hotel to get some sleep. I was pretty tired, as was Sharon. We had a long day tomorrow.

The airports on the Hawaiian Islands are open and free of certain smells. Certainly unlike Chicago's O'Hare airport and others. Anyway, it just felt nice to get off the plane in Maui and feel the warm air flow through the airport. Sharon and I hopped in a different vehicle on this island and drove in search of our rented condominium. It was bigger than I had anticipated. There seemed to be a constant ocean breeze meandering through the place. What a wonderful place to stay. We looked at each other, wondering if this could get any better. Tourism aside, the Hawaiian Islands are such a wondrous place to be. After settling in, the both of us got back into the car and drove all over the island, up to Mt. Haleakala, even checked out a coffee bean estate. We had a simple dinner at a local place, close to the condominium. All of this traveling and sightseeing can be tiring! Sharon and I both love a good bottle of wine, so, we picked up a red and a white before going back to our condo for the evening and relax. I could stay in this condo for eternity, it was so nice. I looked over some of things I bought today. Sharon was enjoying the view from the balcony, or lanai, as they call it. A glass of wine sounded good. Fortunately, there was a bottle opener here in the kitchen, for I did not buy one. I brought a glass of wine out to Sharon and sat down next to her. We sat there talking, or not talking, enjoying the relaxed state, sipping wine. We laughed at the near absurdity of all this, told stories in our lives, relaxed.

The wine had begun to affect us both. We had finished the bottle a little while back. Throughout that time, I had been giving long glances to Sharon's large breasts, with her catching me in the process and not saying anything. Perhaps she caught me licking my lips, as well. But the feeling seemed mutual. I then got up to get some cheese and crackers, when she looked at my crotch, probably noticing some irregularity there.

A few minutes later, I was back and we talked more, telling some fond individual stories. Sharon had on a loose-fitting button down shirt and a pair of shorts. The shirt she was wearing disguised the fullness of her breasts. But I knew they were there. There was an indescribable breeze flowing through and certain quietness overtook ocean. It was the kind of breeze and slight sound of a Hawaiian beach you see or read about. The view from our place on the tenth floor was quite nice. During the day, we saw whales penetrating the surface of the ocean. A remarkable sight! Apparently, we are in the middle of the whale migration. So, seeing them breach the surface is fairly common. We were certainly enjoying these moments in Hawaii. There was some unknown communication going on between us. I felt an arousal between us. Maybe it was wishful thinking on my part. Perhaps. But perhaps not. The glances between us were growing.

It wasn't very late, around 9:30, when Sharon decided to take a shower. It was a long day though, and she wanted to get renewed, of sorts. So, with the water now running, I felt like a teenager again. I didn't know what to do. I never actually anticipated this situation between me and Sharon. I grabbed myself a can of Coke, in need of a caffeine wake-up. I even paced our condo a bit, unsure of the next move. If there even was one. Sharon finished her shower and stepped into the bedroom, changing into some of the new clothes she purchased earlier today. I decided to take a shower myself. The high pressure of water felt good. I even made it a little colder than normal. Should I try and shake off this arousal toward Sharon and just relax? Yes. I felt my blood pumping. I stepped into some new Hawaiian lounge pants and t-shirt I bought earlier and then walked out to the lanai to meet Sharon. She was sipping a cup of freshly brewed Hawaiian-grown coffee. Both of us were now wearing a pair of shorts and new shirts we bought today, just relaxing.

Sharon had to use the washroom and excused herself. It was at that moment, I nearly lost my breath. My clear peripheral vision noticed some unmistakable movement. Sharon had on another button-down Hawaiian shirt. This one was light in color, though, without a bra. How could I not notice the wonderful movement of those large breasts underneath? I find the sight of uncloistered breasts incredibly arousing. My state of shock must have lasted minutes, because Sharon was sitting back down and breathing in the clean air. So. We sat out there a while longer, just chatting and enjoying the Hawaiian night air. Maybe it was my imagination, but I believe both of us were cognizant of each others long glances toward certain body parts. There was a definite rise somewhere in me. It was sort of getting late and Sharon said she wanted to read a little before going to bed.

When I made these reservations, I had gotten us separate beds, for nothing out of our platonic relationship was expected. I stayed out on the lanai a short while longer. My mind was still reeling with these unprecedented actions. At least, for me. Is this a dream? I went to the bedroom and there was Sharon sitting atop her bed, back to the headboard, but in a thin, white, night shirt reading her book. No bra, of course. She seemed pretty casual about the whole thing. But it's not every day that I see my former boss sitting on the bed reading, in a white night shirt with large areolas clearly seen. As I walked to the bathroom, she got up to get a drink of water in the kitchen. Without a bra, Sharon's wonderfully mid to large breasts were clearly seen moving underneath the nightshirt. Stunning. We exchanged passing smiles. She is about ten years or so older than me and still has quite a nice little figure. The dark hair that rested just past her shoulders complemented her brown eyes.

A few minutes later I decided to take one of the biggest risks of my life by asking Sharon if she would like a good neck and shoulder rub. I'm quite good at it, I told her. This really was true. Not that I give rub downs a lot, just naturally good at it. Knowing where to rub and how much pressure to apply with my fingers, palm or whole hand, gauging the person's breathing.

That actually sounds good, Craig. Maybe it was the flight or our walking around all day. Where should I sit? At the edge of the bed is fine. I'll kneel on the bed behind you. Are you going to be comfortable? Definitely. Maybe I'll sit after a bit. So, I pulled myself up behind Sharon on the queen-sized bed and put my hands, palms down, over her trapezoid muscles and gently started rubbing. They really were tight. Hmm. I soon found my groove – a few minutes working the neck, then shoulders, thumbs into Sharon's upper back, etc. Soon, worked my big thumbs into the back of her neck. All the while, slight moans of good feeling heard under Sharon's breath. Well Sharon, what are your thoughts on a full body rub down? If it's anything like what you just did, definitely.

We repositioned ourselves. Me, getting off the bed and stretching. As Sharon went to the washroom first, then got us glasses of water. I grabbed a little bottle of greaseless lotion out of my bag. My turn for the washroom. Water splashed on my face was needed! Wow. I looked at myself in the mirror and shook my head at the events unfolding. Opened the door and I noticed the light was out in the kitchen. There was Sharon. Looking beautiful as she lay quiet and soft, under the sheet. Gave myself an 'Oh my god, under my breath. I asked Sharon if she was ready as I stepped closer. She turned her head up from the pillow, looking right at my crotch. Oh, take those things off. Meaning, my lounge pants. Sharon partially propped herself up on an elbow and lowered the lounge pants for me. Hitting the head of my dick with the elastic band on its way down. Bouncing back to its semi-hard position. Very nice, she said. Grabbing hold and taking a few tugs. I was also complimented on my ball sac that was weighing pretty heavy. I reached down and slid that white nightshirt over Sharon's head, revealing the most beautiful breasts I have ever seen. The areolas around her nipples were, in fact, a dark pinkish hue and wide, as I had previously noticed. Now, how about that back rub, she asked. Um, of course. Inside my head, I shook my head like a cartoon character after being hit with a frying pan. Bringing back to the present state. I walked to nightstand to get the lotion. I'd set it down, for some reason. Great cock, by the way. Thanks, Sharon.

Who moved back under the covers - her lower half anyway - and face down between two pillows. I straddled her legs, lowering myself at their peak. Dropped the white lotion on her upper back and proceeded to do my thing: I worked her upper back muscles and out to the shoulders, then down both sides of the spine with my knuckles. That feels wonderful, Craig. Would you like to do my front? Of course.

I raised my hips up in the air to allow Sharon to rotate her body, which was still halfway covered. We looked into each other's eyes and it was all over. We demanded heightened eroticism from each other, in those few seconds. Without breaking eye contact, I lowered myself to kiss her deeply. Then to the side of her neck, where I kissed her very softly, letting my tongue touch the skin intermittently. With my near-closed lips, I lightly blew on her neck. My right hand slid down the side of her breast, then the left. Back to her soft neck, intently, then off to the side of the neck. That little pocket of sorts, just above the bone. My passion heightened, as time passed. Hearing little 'Mmmms,' from Sharon, I lifted my eyes to see hers, feeling it. I proceeded to slowly lifted myself off of her body and on to the floor, to get a drink of water. Leaving her simmer. What an unforgettable night. The erotic passion continued for more than an hour. Both of us embraced the energy between us. It was wonderful.

When I got back to bed, Sharon immediately grabbed hold of my almost hard cock, which seemed to be thicker than ever, and put it in her mouth and sucked and licked it, cupping my tightened ball sack. These moments almost seemed like a dream, considering our location and the possibility of this ever happening. The beautiful Hawaiian air blew the tall white drapes inside. I have large hands and they covered Sharon's breasts perfectly. Which were full. Leaning my body forward to get on the bed, Sharon pushed herself further back on the bed in an erotic bout of sounds. I sat up next to Sharon, weight on my left hand, near her head. Her kitty was very hairy. I loved it. Absolutely! Dark and dense, but trimmed into a nicely shaped V. Our state of arousal reached new heights. I motioned my right hand over Sharon's inner thigh rubbing and caressing. I love the feel of a woman's soft inner thigh. Sharon let out little moans, as I moved closer to the apex of her legs. Each movement of my hand getting closer. Her right hand stroked my cock in the mean time. Both of us voiced our pleasure more. Hearing Sharon pushed my arousal further. The sound of her voice in this state of pleasure was so erotic. By this time, I was raking her hairy kitty. Moving my index finger over her obvious moistness.

"I can't take any more. I want to feel your hard cock inside me, Craig." "Please do it now, my god."

I rose above Sharon, turned her over and she raised her hips in the air. Mounting Sharon from behind, both of us moaned and let out sudden exhalations of breath and erotic feeling. I loved watching her big tits shake. Her nipples were so hard and erect. Areolas seemed swollen with pleasure. We both sweat passion.

"God Sharon, I love your big fucking tits." "Shake those mother fuckers."

We both let out "Aaaahhh.....yeah.........that's it."

After a few minutes, Sharon wanted to be under me. So did I. I would have better control of my movement. I almost threw her over to her back. The feeling was incredible.

My fully hardened member slid into her moistness below. Both of us continued to let out incredible moans of erotic pleasure. Jesus. I kissed Sharon passionately on her lips and neck and shoulder. My pelvic motioning increased. Sharon's large breasts moved with my motion. My body pumped faster, then eased up a little. Both of moaned loudly, encouraging one another. Listening to Sharon excited me more. I held on to her shoulders tightly, locking my overall body in a fixed position. Allowing my hips to move very quickly. I nearly bit into her shoulder as I did this. Sharon moaned loudly, continually, waves of orgasms worked through her body. Fucking amazing. I could hold back no longer. As I came, loudly, body jerking, I felt the streams shooting out of me, having my own waves of an orgasm. It seemed to last. We were animals in the wild, in our own world. I collapsed next to Sharon. Out of breath. The two of us, motionless. We were awash with relief from release and now comfort. Sharon and I experienced absolutely wonderful eroticism together.

The next morning, I made us breakfast, consisting of eggs, bacon, toast, fresh coffee and juice. The ocean's breeze flew through our condo and our day began. We continued our vacation on to the island of Kauai, seeing unforgettable sites, and also continued the love-making, creating unforgettable experiences. Simply unforgettable.

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Executive Ass.'t Newlywed Martin is ripe for his MILFy secretary's advances.in Mature
The New Nanny Ch. 01 Latina MILF becomes bedwarmer for rich young man.in Mature
HOT SHOTS: M.I.L.F Spring Break Loses his virginity to his girlfriend's mom.in Mature
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
Trading in For an Older Model A young man in a bad marriage finds true love in older woman.in Mature
More Stories