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My Hawaii Beach

Category: Anal Sex
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Sure, it all sounds great. I’m 29, I have my own business. A great house with way more bedrooms and bathrooms than I’ll ever need. Plus, my work brings me to Hawaii every 6 months. You see I own a surf gear company. We make wet suits and boards, tees and shorts with our logo on them. Every six months I go to Waikiki to our head plant. I check that everything is being made properly and legally.

All of this sounds really good when I meet a girl at the bar. It almost guarantees that they will come home with me. It was no different with my last girlfriend. We met at a bar, I told her what I do and the next morning I awoke to her trying to find her clothes that were scattered around the room. We kept seeing each other right up until a couple of weeks ago. That is why I have taken my bi-annual Hawaii trip a month earlier this time.

First, about my ex. Her name is Melissa. She was the first girl who I actually thought was pretty. I know that sounds bad, but she was the first girl who wasn’t an object to me. I had grown up. I knew what it was like with the typical “hot girl”. They usually were attracted to my money and I was attracted to their breasts and their willingness to have sex with me at a moment’s notice. Of course, later I find out that they really were just having sex with my money.

Not Melissa, she was beautiful. She didn’t care if I was able to bring her to the top restaurant in the city, or drive thru at Wendy’s. She was beautiful because of who she was. Not because of a great ass or huge tits, even though those were a nice bonus. She also didn’t understand why I had to go to Hawaii every six months. I probably didn’t need to go twice a year, but I felt it was necessary to the success of the business.

So, after two years of being together she drops a bomb on me. The last time I was away, she tried an online dating service and hooked up with someone. Hooked up with someone to the point that she slept with him on the first date and he didn’t wear a condom. So she left me, to go be with this guy and raise the child. That is why I had to get away from the city earlier than planned.

After an 8 hour plane ride from JFK airport I was tired. Seeing as I wasn’t planning on visiting the plant for a few days there was no better way to relax than on the beach. Waikiki Beach is not the best place for a quiet rest, so I got on TheBus (that is the name of the transportation in Oahu) up to the North Shore. From previous visits, I knew of a little used quiet beach up there whose name I am not familiar with.

I got off the bus and made my way up the street with towel and sunglasses in tow. When I reached this beach I saw that someone else had found my beach! How could they find my beach! I’ve been coming up here for three years and no one has ever found my beach! I calmed down and reminded myself that there are no private beaches allowed in Hawaii (it’s the law).

I made my way down to the shore, trying to make out who was on my beach. As I got closer to the figure I realized it was a lady. She looked to be asleep. I thought about waking her up, she looked like she was going to burn. Then I thought, “No, that’s what she gets for using my beach“. It isn’t a small beach, so I tried to be as far away as possible, but it still felt like we were too close.

I laid out my towel, removed my shirt and put on my sunglasses. If I was back in Waikiki, these actions would have caused ten of fifteen ladies to turn and stare. This lady didn’t even wake up. That was okay, I wasn’t interested in any kind of sexual attention on this trip. This was about relaxing and keeping my mind off of women.

I laid down with my back to the woman and tried to relax. For some reason though my mind kept wandering off to the woman on my beach. I ignored my thoughts which were telling me to check this lady out. When I arrived I had only noticed her long dark hair and her well tanned body. After ten minutes of arguing with myself I decided to turn. After all I was wearing my reflective Aviator Ray-Ban’s, she wouldn’t be able to see my eyes.

I turned and got settled, trying to make it look like I wasn’t looking at her. She was still asleep so I was able to take my time. I settled in and just as I did I could see her awake. Actually she didn’t awake so much as she just opened her eyes. She had been awake the whole time!

She reached into her beach bag she had with her, and pulled out sun lotion. I went to turn back over thinking she could see me watching her, but then I remembered that one can not see through my sunglasses. She sat up and placed some lotion in her palm. I could see that she had tanned, smooth skin. She had to be in her mid thirties, but she looked really good for a thirty-something. She had her back to me, but I still kept watching. She rubbed the lotion into her shoulders and her neck and back. Then she turned to lotion her legs. As she turned she seemed to look right at me. I didn’t budge, I knew she couldn’t see through the glasses. I knew she thought I was sleeping. As she rubbed her legs, I could see they were very smooth and slender. I was starting to become intrigued. I fought back those thoughts and continued to watch the lady. She seemed to take another look at me, then she rose to her knees and started rubbing the lotion on to her chest.

I was blown away. Usually breast size is not a huge issue for me. I mean I usually don’t find girls with really super small breasts attractive, but I don’t usually fixate on them. These though, I couldn’t help but fixate on. They were big and full. Had to be at least a double D cup and that’s probably understating. She rubbed those globes up and down. The moment felt like it was never going to end. Then she stopped and looked in my direction again.

She had seemingly looked directly at me three times now. It seemed like she could tell I was staring at her. Even if it wanted to turn over I couldn’t or else I’d be putting the now large bulge, in the front of my shorts, on display. She put the lotion away and laid back down. This time she laid on her back. Her tits were heaving into the air. They had to be fake. I didn’t care.

I tried to close my eyes and think of other things that would take my mind off of the lady. Sports, family, palm trees, nothing worked. All I could think about was putting my throbbing dick in between those massive melons and fucking them until my cum shot up on to her chin. I wanted to take a look at those tits so bad, but I knew it wasn’t going to happen.

Just as I got my mind onto business I could sense a shadow rolling over me. I opened my eyes to see the lady standing over me. I sat up quickly, very startled. Like a high school nerd talking to the prom queen, I felt nervous.

“Um, hello?” I asked. Damn, that was stupid of me.

“I couldn’t help but notice you staring at me a couple of minutes ago, do you see something you like?” I was too dumbfounded to see the meaning behind this question.

“No, no. I wasn’t staring at you. I was just laying here enjoying the sun.” What a bullshit answer. Damn Melissa ruined my social skills too!

“Darling, I know you were staring at me. I could see your eyes through your glasses.” Damn, foiled! “Now is there something you see that you liked?”

There was no escaping the question now. I quickly thought how I should handle this. I wished I had a couple drinks in me. Beer always seems to make me be cooler. I decided to go for it.

“Your breasts, they are amazing! How big are they?” I can’t believe I just asked that. I’m not that kind of person. Before I could apologize she spoke.

“Thank you sweetie. They are 40 F’s.” I couldn’t believe it. I had really under estimated! “Do you want to touch them?” As she said this she slowly trickled her fingers over top of the mammoth globes. Wow! Was I dreaming, was this really happening?


She leaned forward and I nervously reached out my palm. I slowly cupped the right breast, then the left. They felt amazing. Definitely fake, but amazing! I could feel her nipples harden beneath my hand and her bikini top. I squeezed and pinched to my desire. Then she stopped me.

“Here, this will help.” She pushed the fabric off to the sides of her big boobs where it stayed. She then grabbed the back of my hair and drew my mouth to her nipple. I kissed, sucked and nibbled on the hard nipples. She let out short gasps of air every time I bit down. I pushed them up into my face and sucked hard. “Oh yeah” she wisped.

My cock was growing large and needed attention, but how could I stop sucking on these beautiful tits? This was a once in a lifetime opportunity. She pulled my head away from her and stood up. She turned revealing her shapely ass. That looked really good also. The thoughts I had earlier about her breasts were the same as the ones I was now having about her ass.

She then slowly removed her bikini shorts. I felt like I was going to explode in my shorts. She tossed the bottoms aside, turned, rubbed her tits then walked forward. She spread her legs apart and I saw that she was completely shaved. She grabbed my hair again and threw my face into her hot pussy. I licked her clit up and down, left and right. It tasted so good. I never wanted to stop, it made me want to drive her to orgasm right there. I also needed to explode.

I could feel her pussy swell up. I could taste her release her juices into my mouth. I couldn’t get enough of them. I lapped them up. She moaned hard and continued to shove my face deeper into her pussy. Good thing this was a secluded beach or else everyone would have heard her. She seemed to be reaching climax when she pulled me away and stood me up. She got to her knees and whipped down my shorts. My dick was so hard it nearly smacked into her face when the shorts fell.

She looked at my hard cock hungrily. Then she looked up at me with her big dark eyes and said, “I want to suck you off so bad! Don’t tell me when you’re going to cum, I want to just taste it.”

She didn’t give me a chance to respond. She was on my cock quicker than she had drawn my face into her pussy. She worked it slow making sure to lick every inch. Then she started running both lips over the head and down the shaft. With each thrust she was taking my cock deeper and deeper down her throat. She hungrily moaned as if she hadn’t tasted cock in years. On one thrust she took it so deep that I felt myself hit the back of her throat. It was amazing, I had never been deep throated before. Each stroke after that my cock went further and further down her throat. That was it for me, it pushed me over the top. I didn’t want to cum yet, there was so much more of her I wanted to explore, including that ass. Just as I was thinking about it, I exploded deep into her throat. I filled her much with my hot cum. She couldn’t hold it all and some leaked out the sides of her mouth down her chin. As she took all three of my hot loads she moaned as if she was about to cum. She may have been putting on a show for me, but I didn’t care.

She wiped her face with my towel and said, “your cum tastes so good baby.” I didn’t know what to say. I had never been treated by a woman like this before, and I liked it. All I could think of was, “ahhh fuck!” That was stupid! At least I let her know that I liked it.

We laid on the beach for another hour. No one said anything, after all we didn’t know each other’s names. Maybe we both had the same story, just out of a long relationship and we needed a rebound fuck with no attachments. Just as I was going through these scenarios I fell asleep.

I awoke what felt like seconds later. I must have been at least an hour because the sun was setting. I closed my eyes to go back to sleep. When I awoke a couple minutes later, it was not of my own accord. It was the woman, she was sucking on my dick again and had gotten me hard.

She sucked hungrily again seemingly looking for another shot in her mouth. I stopped her and rolled her on to her back. I wanted more time with her pussy. I thought about strategy and what I wanted to do. Then I remembered how she had just taken what she wanted earlier. It was my turn to do the same.

I laid her on her back and moved down to her smooth, soft pussy. I licked her clit all over and made sure her pussy was nice and wet. I sat up, leaned back and plunged my cock deep inside her. She screamed, but it the scream was filled with pleasure.

“Yeah baby, fuck me deep and hard!” she yelled. That really got me going and I did exactly as she asked me to. She moaned and seemed to be getting close to climax. So I leaned back a bit and flicked at her clit with my right hand and squeezed her enormous breasts with my left hand. She moaned even louder and that was enough to nearly push me over the edge again. I stopped, there was more I wanted to do to her. Mainly a part of her, that luscious ass.

I held her so she remained on her back, and I moved down to her pussy. Again I licked her clit and tasted her juices. I felt as if I was becoming intoxicated from her taste. Then my eye caught what I was really looking for. Her puckered little rosebud. I didn’t know if she was an ass girl or not, but I needed to find out. I slowly slid my tongue south. I passed her pussy opening and she yelped very softly. I stopped to consider my actions, then threw caution to the wind and went for it.

As soon as my tongue hit her ass hole she moaned. It was a mixture of surprise and apprehensiveness, but mostly pleasure. She tightened up at bit. Then as I circled my tongue around her rim she calmed down and began to enjoy the mouth play her ass was receiving.

I licked at that rosebud feverishly. I had seen this done in porn, but I never had the guts to try it. Now I was doing it and it really got me hard. I licked at her puckered opening like it was a lollipop. She moaned because I think she knew how naughty she was being. I made her ass hole very wet and I tongued it until I couldn’t think of any more movements to do.

With my new found sexual confidence I grabbed her hips and brought her up to the doggy style position. Her ass was high in the air and I gave her rosebud one final treatment before I grabbed my cock and rubbed it against her ass.

She looked back at me and said, “You’re a naughty fucker, and I love it. Stick that hard cock right up my ass!” I had been with a few dirty talkers before, but she by far was the best. She started to play with her clit and I slowly pressured my cock into her ass. She moaned in painful pleasure as my dick slowly entered her rear. Soon enough I was balls deep in her ass. I wanted to take it easy in case this was the first time she had anal. Then she looked back at me with animalistic passion in her eyes and said, “Just fuck my ass already! I need you to fuck my ass hard!”

I followed her passionate orders and drove deep into her ass. I felt every bit of tightness she had. I loved the feeling of stretching her ass as I drove deep down into it. Her moans and panting were in rhythm with my thrusting.

“I’m going to fucking cum.” I said. “Shoot it in my ass baby!” She responded.

Her dirty talk sent me to the next level and I unloaded cum into her ass.

“Fill my ass up!” she screamed.

It flowed deep into her and filled her up. I kept driving hard into her ass and every time I pulled out, my cum came up with me. It spread over her ass cheeks and covered my cock. I slowed and pulled completely out of her.

“I’ve never had an ass fuck like that.” She said, “Thank you sir”

We laid down together again in the sand. I hadn’t been this happy in months. We held each other for a while. Again, I played some more with her huge tits and she brought herself to orgasm, playing with her clit.

We both fell asleep, at least I thought we both did, because when I awoke an hour later, she was gone. I was left with my memories and a whole ten days to myself, in Hawaii, to think about them


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