Hawaii Aloha

How I met Mary on the island of Maui and the start of our adventures on the island paradise.

I was waiting, seated on the bench of an outdoor mall in Wailea, Hawaii for Mary a 51 year-old African American woman that I had met on the affairs website Ashley Madison. I had been a member of the site for quite some time, without a positive result and was beginning to believe that I was too stupid to know how to attract a woman. I had tried all sorts of ploys without much luck and Hawaii was my latest attempt. The site had a feature that allowed you to send messages to a large number of women in the area where you would be traveling. So I made up a "canned" message and sent it out to the 20 or 30 women who lived on Maui and belonged to the website. Mary was one of the many and was not one who I had specifically searched for but she was the only one to respond to my initial email. Her web moniker was "Coco" and we had corresponded for a few weeks prior to my departure, agreeing to meet when I arrived. It was a couple of days after arrival that we finally managed to email enough back and forth to figure out how to meet.

So I was waiting in the open-air courtyard of the mall for Mary to arrive. She had selected a restaurant in the mall for our first date but was more than 30 minutes late and I was beginning to believe she was not coming. All of a sudden, there she was a slim, attractive "coco"-colored woman.

She rushed up and said, "Sam?" and went on, "I am so sorry I'm late but my motor bike was stolen last week and the bus was late!"

I smiled and said "I am sorry about your bike, but I am glad you made it!"

She stepped up and gave be a peck on the mouth and continued in rapid fire "I'm glad I am here too, I have been really looking forward to your coming and when I got your email I was so glad we would finally meet! This restaurant is one of my absolute favorites and I think we are going to have a great time!"

Mary was an absolute bundle of energy, very vivacious with an infectious smile. She grabbed my hand and drew me into the entrance of the restaurant and up to the slim blond hostess waiting there.

"Party of two, under the name Mary"

The hostess replied, "I am so glad you two found each other! I went looking for him but didn't find him after you had called."

Mary said, "Yeah, it was great that he was here, I was so afraid he might be gone by the time I arrived!"

The two women chatted as if they had been friends all their lives, but of course they had only just met. I was to learn that this interaction was typical of Mary. She was immensely gregarious and people just loved to talk with her.

The hostess beckoned, "This way please." and then she and Mary continued to chat as we walked to our nearby table. The restaurant, like many places in Maui had a roof, but was open to the ocean breezes and there were paper lantern lights and candles on the tables providing a soft glow to the room. We were seated at adjacent corners of a small square table and turned to chat with each other.

Mary said, "I think you are going to love this place! It has some of the best food on the island. I haven't been here for over six months but I always have a fantastic meal."

Mary had a way of filling the space with words and so as she chatted on, I had a chance to observe her. She had full luscious lips common to many African Americans and her dark brown eyes were bright with excitement. Her face was very animated like the rest of her demeanor and showed excitement, anger, joy and sadness in pantomime to what she was talking about. A saucy multicolored cap topped a set of a heavy braids cascading down her neck and upper back. She was wearing a sleeveless white blouse, which was tucked into skin-tight, faux leather pants and covered stiletto heeled open toed shoes.

So, we talked in the quiet hubbub of the restaurant and I learned that she was a single mother who had immigrated to Maui from southern California with her then infant son 30 years previously. At first, she had lived with her sister and her sister's young daughter and had made ends meet by waitressing at one of the local restaurant-bars in Keihei. She had had an eclectic life wandering around Maui performing all types of jobs, but her latest gig was as a store display consultant. Companies would hire her to come and mimic the activities of a shopper and then give suggestions about how to alter the store displays to entice shoppers. She was an independent contractor and got most of her work by word of mouth. I was very impressed with her moxie. To me it appeared as though she had perfected the ability to live fully with limited resources.

Our meals arrived and we dug in. The food was quite good and we had a good time chatting with each other. We traded stories about our infant grandson's and our worries for our children. I told Mary that I was attending a conference in Wailea that kept me from early morning to about 1PM and then I often had the afternoons and evenings free.

As the meal progressed, we began to connect physically as well as mentally. Mary would reach over and touch my elbow or I would gently tap her knee. Soon my hand was permanently attached to her left thigh and I gently stroked along the top, outer and inner aspects. Occasionally, I would stroke her forearm or reach for her hand. With the attention, Mary's conversation became increasingly animated and her smile became a permanent fixture of her face.

We ordered dessert, which was also quite good, but I almost did not notice the creamy and crunchy texture of my crème brûlée. My attention was completely focused on the beautiful woman before me and honestly, I could not wait to leave the restaurant for the after-dinner treat! It seemed as though Mary was similarly preoccupied. It was almost torture for the two of us as we waited for the check. But finally, the bill was paid and we exited the restaurant hand in hand. I was staying at the Grand Wailea hotel, which was on the grounds directly adjacent to the mall and so we had a 10-minute walk to the hotel entrance. As we walked we continued to chat and alternately held hands or ran our hands along each others, backs and buttocks. By the time we reached the hotel lobby, we were practically running with the anticipation of being alone together.

Like almost everything in Hawaii, the hotel had an open-air configuration and the elevator to my room on the 7th floor was out in the open. Mary and I waited at the entrance arm in arm and across from us was a cluster of Japanese tourists and a middle-aged man with his two children in bathing costumes. I was gently running my hand along Mary's back as she leaned into me.

The elevator finally arrived and we crowded into the small space. I had my back to one of the walls and Mary positioned herself just in front of me and leaned her firm rounded ass into my crotch and ground against my semi-erect cock as I placed my hands upon her hips. I was almost crying with anticipation but remained stoic in front of our co-passengers.

The Japanese exited on the second floor and the father and children the fourth. With the closing of the elevator doors, Mary let out a laugh, turned, pressed her body into mine, gave me a warm open-mouthed kiss and said, "I thought they would never leave!"

In the next few minutes of the ride we pawed at each other and passionately kissed. I ran my hands along Mary's flanks and over her rounded ass. Then ran up along her chest to gently squeeze her small tits though her blouse. Her hands rubbed along my back and flanks and her belly pushed against my swelling cock. Meanwhile, we were kissing passionately, tongues exploring each other. Mary pulled back slightly and gently brushed her hand along the bulge in my trousers and gave another barking laugh.

"Ready are you?" she said.

And I replied "Yes!"

The doors shushed open and we practically ran down the open-air balcony-hallway that lead to my room. As I fumbled with the key, Mary was running her hands along my ass, which was not helping my coordination, but the door was finally open. We entered the room and stood facing each other at the side of the queen bed. We embraced with a feverous passion. She gazed up at me and I leaned down to give her an open-mouthed kiss. Our tongues played with each other and explored the wet softness of each other's lips and mouth. We were both panting with excitement and fumbling with the buttons of each other's shirts. I finally opened the last button and was able to caress her soft chocolate flanks and run my hands along her back. She had B-sized tits and was wearing a black bra with white lace on the margins and I reached up to caress them, playing with the margins of the bra.

Meanwhile, her hands were in my shirt, lightly stroking my chest sides and back and eliciting electric tingles in their passing. All the while we were tonguing each other, interspersed with gasps and then ... pausing, we looked into each others eyes and knew that we wanted each other ... NOW! So, we stepped away and stripped the remaining clothes off in a flash and stood completely naked before each other.

My cock was rigid at attention and staring intently at the petite, chocolate-brown delight before me. She had high cheekbones, lush lips and a slightly hooked nose. Large, golden, hoop earrings dangled from her earlobes and she was flashing a bright white smile. Her tits were small and sagged slightly with erect dark brown nipples that I longed to suck. She was quite thin with almost no fat and had a washboard stomach that swelled into perfect rounded hips with a muscular ass and legs. She was completely shaved and so I got a glimpse of her bald pussy protruding as a small mound between the columns of her legs.

We embraced again and enjoyed the delicious feeling of skin gliding over skin. My dick was particularly pleased to press and rub against her smooth belly and kept sending me shocks of pleasure at finally being included in the play. We kissed some more with tongues darting back and forth and I stroked her back and smooth round ass and then reached up and tweaked her right nipple. I kneeled down and began to suck and lick her breasts. I flicked my tongue across her nipples and tried to pleasure her as much as I could. Although, I think she enjoyed my attentions, it wasn't what she really wanted and so she drew me up and knelt before me and took my cock in her mouth. She licked along the shaft and sucked my balls, causing me and my cock immense delight. Then she took my cock in her mouth and lowered her head, taking at least 7 inches of cock into the soft recesses of her throat.

"Aaahhh!" I had never been deep throated before! A rush of euphoria spread from the base of my pelvis and spread through my torso. Smooth glide of in and out, in and out. I could feel the insistent urge to ejaculate and so I pulled away from her open mouth as she looked up at me.

I said, "I was just about to cum and want to wait. So, it's your turn" and I took her by the arms and gently urged her up and sitting on the adjacent bed. I went to my knees and with her crotch in front of me, I got my first good look at her pussy. As I noted before, she was completely clean-shaven and her mons pubis formed two, soft, bald mounds. Her outer pussy lips were quite small and her inner lips were two pink curls below the largest clit I had ever seen in real life. Mary's clit formed a small barrel about as big round as my pinky with a small pink hood overlooking the dark recesses of her vagina. I gently tongued along the inner surface of one thigh and then the next, progressively inching toward her moist pussy. I licked along the creases where her thighs met her crotch and then gently licked the surface of her asshole, which resulted in a low moan from the bed above me. My tongue played with her inner pussy lips and then flicked the barrel of her clit, causing another moan. Then I had my tongue glide along the surface of her pussy and up and over the hood of her clit. Again ...and again ... and again. With my forefinger I probed the pink crinkly surface of her vagina as my tongue played with her pussy lips and clit. Mary was absolutely still with concentration but all my efforts failed to induce her to cum, so she took hold of my face and drew me upwards.

She said, "Sorry, that was great but I just can't seem to cum. I want that big dick of yours!" And with that, she lay backwards onto the bed, with her ass on the edge and her legs raised upwards and outwards to expose her twitching pussy to penetration. So, I stepped forward, took a firm hold on the base of my rigid cock and thrust it into her waiting twat.

"Ah!" she gasped and I almost saw stars, that first thrust was so pleasurable. We had both been at an incredibly heightened sexual tension for the last hour of foreplay in the restaurant that the first meeting of pussy and cock was almost surreal. And so I began to pound her pussy with all the energy I could muster. I placed my arms to either side of her torso and so she stroked my flanks, back and buttocks, progressively heightening my euphoria. We were both gasping with pleasure and occasionally she would utter another low moan. In out, in out, thrust, thrust to ever rising heights. My world shrunk. Before me lay a slender black woman moaning in ecstasy and my concentration was fixed on the glide and return of my rigid cock as it was held in the firm grasp of her warm wet pussy. The tension and thrill of the moment grew higher and higher, interspersed with moans and tingles. Then a kernel of agony-ecstasy bloomed at the base of my being and with that ... my cock imperceptibly swelled and ... I heard Mary gasp and cry out and ... I echoed her cry as my cock exploded, pumping cum and more cum into her already slick pussy. In euphoria, I collapsed on top of her and was almost insensate for a moment or two.

I became aware once again and drew back, standing at the bedside. My dick remained semi-rigid, defying gravity for yet a few more moments. Mary was covered in a fine sheen of sweat and she gave me an almost weary smile. Her legs remained out thrust, her crenellated pink pussy gaped open and glistening pale cream cum dripped out to slowly ooze over her anus. We laughed! and Mary scampered to the bathroom to expel my charge. I looked about at the rumpled quilt and the scattered clothing.

Then Mary was striding back into the bedroom and said, "That was fantastic!" and she gave me an exuberant kiss as we drew together, arm in arm.

It was pleasurable to gently rub against each other, a faint echo of our earlier joining, but then it was over and we drew apart.

"I have to wake at 5:30 for the first meeting and I snore! Do you want to stay tonight or go home?"

She decided to return home that night and we agreed to try to meet again later that week.