Anal in Grand Cayman

Having his cock enter her felt incredible, and she thought he would remove his finger from her ass, but he did not. His dick was about half way inside her and she was not sure she could take anymore, but then a wave came by and the boat rocked some, Charles braced himself for the boats movement, but she did not and she found herself going backward which drove his entire 9 or so inches into her wet cunt and she let out a howl into the night air as she felt all of him deep inside of her.

Knowing that it was a shock to have him all the way inside her so fast, Charles did not move, he did not pull his cock out, but did not do anything but stay still so she could get used to him. Samantha looked at the moon and could not believe where she was or what she was feeling. This had to be about the biggest cock she had ever had, and now it was all the way inside her, not to mention she still had one of his fingers still half way up her ass. The feelings were intense, and she tried to relax as she just stared at the memorizing moon in front of her, and feeling her very full pussy and awkward sensations in her ass.

It took about 5 minutes, but he felt her pussy relax slightly around his cock, so he pulled back half way out of her, and then slowly pushed forward until he was once again seated balls deep into her pussy. The feeling was incredible to her, and much to her surprise, she pulled her hips forward until just the tip of his cock was in her, and then she pushed back quickly taking his long thick cock back into her. Charles knew what she wanted then, and he began to pull his pole out and back into her with deep strokes. To add to her sensation, he pushed his finger deeper into her ass until it could go no more.

Samantha was in a whirlwind of feeling as she felt her pussy getting fucked with a large cock, and having a finger deep in her tight ass. He then started pulling his finger out of her ass, just as his cock was pulling out of her pussy, then his cock and finger would drive into their respective holes in unison. Damn, she thought, I'm being double fucked as both her holes were feeling the sensation of being opened, one with a cock, one with a finger. Much to her surprise, she felt herself pushing back on him when his cock and finger were just about out of her, helping him reenter both of her holes.

This reaming was taking their effect on her and she felt something coming on, but with the strangeness of the finger in her ass, it snuck up on her like a tidal wave and all of a sudden her legs began to quiver and she gripped the railing tightly as her body convulsed, and she felt the most intense orgasm of her life roll through her entire body. Charles felt her orgasm through his finger and cock, and increased the speed of his thrusting for just a moment, then slowed down as her orgasm subsided. He pushed his cock deep into her and held it there, then slowly pulled his finger out of her ass.

Coming out of her dream and back to reality, she had a huge smile on her face as she looked back to see him, with both his hands on her hips, and his still rock solid dick buried into her pussy. They did not move for a few minutes as both were enjoying the afterglow of her orgasm. Then she looked at him and said "I think it is your turn to cum", "yes, it is" he responded to her, that is when he surprisingly pulled his cock out of her freshly fucked pussy. A frown came on her face in an instant as she missed the feeling of him inside of her. Then a feeling she felt earlier this evening came back to her, the feeling of lotion being poured down the crack of her ass.

She turned around to see Charles coating his cock with the lotion and she wondered why he was doing that, her pussy was definitely wet enough, so why the lotion? Then she felt the tip of his cock rest just against her asshole and if the moon was looking at her, it would have seen a deer in headlights look on her face. Quickly she said to him, "I don't do anal sex", "did you like my finger in your ass" he asked, and for a moment she thought about it and had to tell him the truth, "yes, I liked your finger in my ass", she said.

Charles assured her that this would feel good to her as his finger did, and that they would go slow and gently. He had to push some, but slowly her virgin asshole opened up and they both felt the tip of his cock enter her tight backside. A rush swept over her as his big head penetrated her ass and was a much different feeling than his finger a few minutes before. Then it popped into her mind, wait, I'm not an "up the butt girl", for some reason remembering the episode of Sex and the City where the theme was all about anal sex and how most of the girls did not want to be known as "up the butt girl".

As she was thinking of Sex and the City, his cock was slowly making its way into her tight cavern and the next thing she knew, he was half way inside her and she felt a pressure like never before, there was some pain, but as she breathed deeply, and thank goodness he did not try and go any farther, the pressure began to subside, and to her extreme surprise, she was actually getting comfortable with his cock in her ass, although comfortable was not the right word to describe it, but no other word came to her mind.

It amazed her that he was able to enter her like that, but the lotion must have been a big part of it as well as her ass being rimmed and fingered prior to his cock attempting to enter her. Then she felt him pull out a little, and then back into her. Having a cock pull in and out of her was not that new to her as she had been having sex since her first year of college many years ago, but having one do it in her ass, well she felt like a virgin again as she was not sure what to expect. He took his time, kept his strokes slow as he pulled out, and then pushed back into her. Every few strokes his cock seem to dive deeper into her ass than it had a few strokes ago, and eventually it happened, she felt his balls against her pussy and she realized that she had taken his entire cock into her ass, and that she was now an "up the butt girl", but she did not care.

Her virgin feelings drifted away as he began long full strokes in and out of her now not virgin ass. Before long, he was thrusting as hard and as fast as he had been when fucking her pussy and she was in state of euphoric daze with this new sensation on and in her back side. He began to grunt, and for the first time spoke while thrusting as he asked her "do you like my cock deep in your ass baby", and she replied by shouting at the top of her lungs, "Fuck my ass baby, fuck my ass hard and deep".

Somewhere along the beach, a couple was walking by the water's edge when out of the of the night they thought they heard a woman shouting, "Fuck my ass baby, fuck my ass hard and deep". They thought that someone out there was having a good time and continued there walk on the beach and each began some lusty thoughts of their own.

The feeling of fucking Samantha's tight virgin ass was begin to catch up with Charles and he felt himself starting to lose control, "I'm going to fill your ass full of my cum baby", she heard him say, which to add to her surprise triggered another orgasm in her which she could not believe she could have while being fucked in the ass, but here she was shuddering from another orgasm. As her orgasm subsided, she looked back at Charles who was still fucking her ass like there was no tomorrow and she told him, "fill my ass full of your cum baby, I want to feel you cum in my ass", that was as much as he could take and immediately she felt his cock pulsate, then a new feeling that she had never had before, warm cum entering deep inside her ass.

Charles kept on thrusting, although more slowly now as her kept filling her ass full of his cum, which in his final strokes, made it even easier as his cum had thoroughly lubricated her ass. Finally he stopped his pumping of both his cock and his cum, and he stayed deep in her ass. The two just stayed still for a moment, both enjoying the afterglow of an orgasm.

Reality came back to Samantha, all movement had stopped, but she still felt his cock in her ass, although it was not quite as hard as it had been a moment before. She had finally had her erotic fantasy had come true, and knew she would never be the same as she would now tell herself that she was well indeed an "up the butt girl", and was loving it.

She felt some of his cum beginning to escape from her ass and drip down her and asked him "we better clean up before we make a big mess", "I have an idea" he said, then asked "can you swim"?, "of course she said", with that he slowly pulled his cock out of her ass, he took a moment to look down and see what was her tight little asshole now agape and his cum beginning to pour out of it as her gaping cum filled ass shimmered in the moonlight. Then he jumped overboard and into the water. Samantha was taken back as he leaped over the side, then realized what he had in mind and she too jumped over the side of the boat and into the warm Caribbean water and knew she would never be the same after that night and smiled thinking how much excitement her life would be now.

The End.

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