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The Holiday Day 1

Sun dresses always did it for James. Specially when it was clear there was very little on under it. He had noticed it way back in the airport at home, where the wind had been blowing and snow had been coming down. She looked cold then, but coming off the plane in Mexico it looked perfect. She was with a group, he figured 3 maybe 4 of them. James was on his own. Last minute his friend Eric had to cancel the trip. But paying top dollar for an all inclusive vacation, James wasn't about to lose his money. He smiled at her across the baggage carousel waiting for their baggage and she smiled back but then was surrounded by her friends again. Ah well, James thought he would have plenty to look at, at the resort. So once he had his bag James headed out to wait for the bus. Like every time he was there, the bus driver offered beers and he was happy to have one in the heat. He was also happy to spot the girl on his bus. Maybe he would get a chance to say hi to her at some point this week.

Check in went nice and smooth. The bell boy that took him to his room started the small talk. James wasn't sure if it was for a better tip or what. It was the usual stuff as they walked the buildings, then he asked about a "lady" friend. James sad sadly no and the bell boy slowed right down. "Listen, it is kind of an open secret but head by the tropical pool any night after 11. Just for fun." He said then winked at James. The conversation was normal the rest of the way to the room. James made sure he gave the bell boy a good tip and wondered what he meant.

As he unpacked James marveled at the room and was actually kind of glad Eric cancelled. James had upgraded to a king room and it was great. The bed was in the middle, with a large Jacuzzi tub right beside. The TV was hung so it could be watched in either. The bar was fully stocked. Plus he had a couch and desk on the far side of the room. The bathroom was separate, with a massive shower. Every thing was marble or tile. Though he had been to Mexico a few times never had he had a room like this. James turned on the TV and flipped through the channels. It was then he remembered a joke Eric had made. They might want their own rooms as it came with free porn. The first couple channels were nothing special. The same playboy channel that you might get back home. Another that was a naked talk show, then came the local channels. These caught James' eyes really fast.

Latinas, he had always liked them. Even before everyone seemed to be an ass man. He had loved the big curves they had. Loved the tiny bikinis they wore. The caramel skin and dark hair, he just loved it all. The screen currently showed a Latina bent over a couch. What James would have called a fat Latin male was behind her g-string to pulled to the side as he pounded into her. Her great booty jiggling every time he entered. On he other side of the couch a younger much more fit male was holding her long hair to the side, so the camera got an excellent view of her face. Or what could be seen, she was taking his whole shaft, down to the balls in her mouth. James laid back on the bed and wondered if he could ever have a threesome. It looked hot, but honestly only with 2 guys and a girl. He didn't think he could pleasure two women at once. He could feel blood rushing to his cock as he watched. The filmography was terrible, he thought and laughed to himself. Who thinks about filmography as a beautiful woman is being pounded. He could hear every thrust, the loud skin on skin smack. But it looked like someone had filmed it with an Iphone. It didn't matter he popped his button and slid his hand into his shorts. It didn't take long at all, before they were around his knees and just as quick he was stroking hard. He wasn't looking at the tv as he came. His eyes were closed and he exploded all over. He was glad it was a king sized bed and that they should clean the sheets tomorrow. James unpacked and hopped in the shower. It overcame him again, he didn't know why he was so horny, but he came again in the 3 person shower in his hotel room.

It was a later dinner that night. But is was a feast for his eyes as well as James stomach. His Latina dreams were coming true. SO many of them on the wait staff and cleaning the tables. It was a couple beers in and two tequila shots when jokingly he asked one what was fun to do there at night. She was cute, quite young with very broken English. She said hit the on site night club, so James feeling brave asked if staff could go there. She laughed and said no, it was frowned upon. So James handed her a $20 bill. Her eyes widened, then came the secret. The far back pool, she said check it out. After midnight. She said she couldn't come but he would have a great time. So James killed an hour or two at the bar. Getting his liquid courage to go see what might be going on in the back pool.

The back pool was located as named, in the far back. By the VIP suites. James figured something had to be up. The path to the back was the only one not lit. Which was very strange all things considered. If he had a suite he would want to be able to see how to get to it. But he was guided by laughing and talking. When James rounded a corner to the back pool he was shocked, there was maybe 15 people in it. All ages, races, sizes. Mostly naked and some engaged in all sorts of sex acts in and around the pool. Very few even took notice that he had come around the corner. But one couple sitting by the side smiled at him.They were a few years older, but still in great shape. James couldn't see what was happening under the water but, his head was laying back on the poolside and he was smiling. "Coming in?" He asked James.

James had never considered himself a prude but for once he was stuck. Should he get in? Maybe just walk away. James peeled off his shirt, the man smiled at James well toned body. "Everyone is going to love you. We are all clean and it is all fun. NO means no and that's kind of the only rules" The man said closing his eyes and moaning. James noticed the woman's breasts were floating, massive and fake for sure. James slipped into the pool beside the woman, he could now she her arm pumping the mans cock vigorously.



She smiled at James "Oh and my hubby forgot no clothes allowed." Giving a quick tug on James shorts. It was the moment of truth and James slipped them off as well setting the outside the pool. James felt her other hand running down his chest almost instantly. It might have been the excitement of seeing what was going on, or the thrill of joining something so taboo but almost instantly he was rock hard. She found that but moved even more south and started to massage his sack. So soft and gentle, teasing him. James took her all in, she had to be in her forties maybe pushing fifty maybe just over but hard to tell. Longer blonde hair, it was dyed, but he couldn't prove that as she had no hair anywhere else. She was toned, likely worked out some James though and noticed she had a few very small tattoos.  set of kissy lips inside her thighs, some sort of Chinese symbols above her left tit. Her hand had moved again and was slowly stroking him, she had stopped on her husband. He stood and walked around to the other side of James, then he placed his hands on James shoulders and began to massage them. James moved a bit uncomfortably and the man chuckled a bit.

"Its okay, I will take that as a no. Not everyone is into that but I do like to watch." The man floated toward the middle of the pool still staring at James and his wife. She stopped and slapped the side of the pool, then motioned with her head for James to sit there, which he did. At first he noticed how cold the tile was on his ass but that passed in seconds as he felt her mouth encase his member. Then she went to town. Up and down, able to take it all in her mouth. Lips touching his ballsack. But not stopping there. Taking it out and licking the shaft. slowly rolling her tongue around the tip and of course stroking him the whole time, James felt like he was in a movie and hoped the excitement was why he exploded so quickly and without warning. It actually was embarrassing.



"I am, I am sorry" James stammered, noticing he had gotten it everywhere. She was using pool water to rinse off. She simply laughed, but her husband spoke up.

"Happens all the time. Quite often on a persons first time." Out of the corner of his eye James noticed she climbed out of the pool and sat beside him, then she laid back spreading her legs wide. "You don't have to of course, but we would enjoy if you did." The husband said swimming over and climbing out of the pool to sit beside her. He took one breast in his hand and began to suck it. For a second James was confused, hoping the man didn't want anything then he looked down at her. She was clearly ready for him. He started with a kiss, then a nibble and lick down her inner thigh. The whole time he slid two fingers in and out of her. A quick glance up and James saw her husband was kissing her and squeezing a breast in his hand. With his other hand he was still pumping himself. James took her clit in between his lips and pressed down. She seemed to have liked it, as she kicked a leg out. His tongue began darting in and out of her. A hand shot out and grab James by his hair, he knew he was doing good. Big full licks of her meaty box and her grip tightened on him. Then he concentrated on the clit. Licking it, teasing it with his tongue while sliding fingers in and out of her. The whole time her husband seem to be working on her upper torso. James had made more than one woman cum before, but it had always been from sex, not from going down. He was shocked and slightly turned on when she exploded on him. For sure she was a squirter. James gave a nervous laugh and dunked his head under the pool water. But the couple carried on, in had the husband rolled over and mounted her. James unsure of orgy etiquette looked around and while some people seemed like they may want him to join James climbed out of the pool. Grabbed his shorts and started toward his room with a lot to think about.

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