Caribbean Holiday Pt. 01

Two weeks in a Caribbean resort without own private bungalow separated from the main complex on the beach. Specially chosen to be the one that was the most removed from everyone with our own private little beach to play in at our doorstep. Food and company only a brief walk away - plunge pool, lounge, huge bed, indoor and outdoor shower, satellite TV and a large fridge to fill with our own likes for alcohol.

The first two days we chilled in the sun with resting, sun bathing, drinks, walks, swims and sex. Mary was a nymphomaniac and was the instigator in most things sexual in our relationship - she wasn't in any way inhibited about anything to do with sex, her body, any taboo subject or main stream. Something in the sun and the sea triggered her libido even more and she was either having me pleasure her or managing to play with herself several times during the days.

On day three we got up late from a night of sex and alcohol and were laying on our beach naked when a voice called from the compound gate,

"Relaxing massage for you Madam?"

I am sure whoever called out couldn't see me so only called to Mary. Before I could say anything she stood up and wrapped a sarong around herself and went to the gate asking for the price. Once she opened the gate a young and physically perfect local male stood negotiating a price and telling her he was qualified in Swedish and sports remedial massages. Haggling gone the boy was invited in and Mary lay down and removed for sarong - naked and laying on her front for the boy to massage her as I also lay a few metres away from them.

The boy (Kevin) began to apply oil to Mary's back and legs and began to massage her as they chatted. Mary's legs were closed tight and he worked his way on her back and legs over the next 30 to 40 minutes.

Mary asked me to go and get some soft drinks and when I returned I noticed her legs were no longer closed but wide open and that Kevin was massaging the back of her thighs sliding his hand inside her legs as he did. I put 2 soft drinks down near Mary and another next to Kevin and sat back down with my sun glasses on and watched without being obvious. Just as I sat down Mary turned her head to me and blew a kiss and smiled making faces to make sure I was in on her fun of letting Kevin play with her.

Mary and I had explored partner swapping a few times and although I knew she wanted more men as part of our relationship we had never gone down that path. I watched as Kevin played with her legs and pussy and Mary stayed watching me so I could see her face as she was taken to her first orgasm from Kevin. She made sure Kevin and I knew it too with her moans and panting.

Mary turned over and sat up to have a drink and told Kevin to have his and take a small break. Mary then said,

"Wow, that was awesome and it looks like you enjoy seeing your Wife being handled by another man by that hard cock."

I hadn't thought about it but my cock was hard from the scene I had just observed. I didn't comment and just smiled at Mary and began to turn over when she said,

"Darling, it is do the front time and I need to see that it turns you on, please don't hide your arousal from me."

"As you wish my Darling," I said and stayed sitting up watching.

Mary lay back again and told Kevin to finish with the front now. Mary stayed watching me as Kevin massaged her breast and body. She watched my cock stay hard as I saw him play with her and she even moved her hand up to gently touch Kevin's cock, I could see her feeling it and seeing how big it was as it got hard and pressed against his shorts.

Kevin finished off playing with Wendy's pussy again and brought her to another orgasm while Mary and I watched each other. Mary composed herself and walked Kevin to the gate holding his hand and kissed him sensually good by. She returned and just straddled my face telling me to eat her. As I licked and sucked Wendy's pussy she told me how she was about to let him fuck her she was so horny.

Mary turned around and with me still licking her she began to play with my cock telling me how she loved it when I cleaned her up after another man had played with her and that she was so happy I got turned on from watching Kevin play with her pussy and body. Mary, between having my cock in her mouth, also detailed how big she thought his cock was and how she would be dreaming about something that big now. Laughing and shuddering from another orgasm she brought he to cum too and swallowed every last drop ... running into the water afterwards yelling for me to follow her.

As we cuddled and kissed in the water Wendy told me of a bar Kevin had suggested and how she wanted to go and dance, asking me if she would mind if she sampled some of the local boys. I was not even allowed time to answer before she was kissing me and thanking me and suggesting I could enjoy some local ladies too.

That evening we went to the bar/disco and joined about 30 locals. The bar was clean and tidy but had seen better days and was obviously a local haunt rather than somewhere the tourists frequented. We came in and ordered drinks with everyone being nice and friendly. Kevin was there and he waved as Wendy and I got a table and down a few drinks and then had a few dances. The whole vibe in the bar was fantastic and the alcohol flowed as we danced away happy and enjoying ourselves. As the next hour or so went past the patrons increased to about 100 and about 11:00 pm Kevin came over and asked if it would be OK for him to dance with Wendy. I stayed at the table while they went to the dance floor.

Wendy and Kevin danced so sensually touching and holding each other during dancing and he held and grooved her with his body and his hands. Grinding against her and holding her backside they were both enjoying themselves. The lights on the dance floor turned Mary's dress see-through and I watched amazed at how gorgeous she was in a white dress with a very visibly g-sting the only other thing on. A few other friends of Kevin joined them and 5 men, Wendy and another Lady all danced together with the two girls in the middle as the boys took turns dancing close with each of the girls - the boys took turns with Wendy's purse buying more drinks and making sure I also got another each time.

Eventually the local female came and sat with me while the boys continued to dance with Wendy. We chatted and laughed, by this stage I was so damn drunk, and I both watched Wendy and chatted with Simone as the next few rounds were purchased.

Wendy came over with three more drinks each and told me she was just going out with the boys for a joint. Wendy and the guys disappeared and Simone and I chatted. I lost count of time I was so drunk and then Simone grabbed me and pulled me onto the dance floor, I am not sure how long she had been back but Wendy and the guys were also there. We did a local custom dance where the girl touched a part of her body and the male then did in the next repeat beat. Simone would touch her shoulder and I would then etc. Other couples / groups were too Simone seemed to keep me with my back to Wendy and the boys. They stood in a circle around her and she would do the dance with one then the next, then the next etc.

I positioned myself to watch Wendy and she would do the same thing for each guy in turn - she tweaked her nipples and the guys all played with them when it was their turn, she gripped her arse cheeks and the boys would do the same in turn. It was then I noticed that the buttons on the front of her dress were open very high and that she didn't have her g-string on any more. Just as I saw this she touched her pussy on her turn and the guys all laughing took turns gripping her pussy to the song. As the song was replayed Wendy called me over to join the boys and Simone went over to the bar. We did a few rounds of fondling her breast, pulling her nipples, groping her pussy and fondling her arse and exhausted we all went outside and Simone joined us.

As we walked to where the boys had their cars the bar closed and we were then the only ones in the car park. With Simone and I also there, and she lighting a joint for the two of us Wendy undid her dress buttons, took it off and threw it at me she then said,

"Common boys, have me any way you want."

Kevin and his 4 friends all moved towards Wendy and started to take turns kissing and fondling her pussy, breast, arse, legs, head and arms as Simone and I just watched smoking a joint.

Every single possible positions was demonstrated to me as all of the boys took Wendy doggy, got sucked and two of them even in her arse as each of them finished Wendy sucked them all clean and I saw a very submissive Wendy when the boys used her, a very different Wendy to me. After the boys had finished Wendy had cum all over her face, hair, legs, pussy and hands and I handed back her dress, which she used to clean herself. Everyone except Simone and Kevin said their goodbyes and Kevin marshalled us into his car and they drove us back to the bungalow.

Wendy and Simone sat in the back and Wendy put her hand forward and held mine the whole way and when I looked back Simone was wiping her clean with a towel that was in the back. Everyone was nice and happy when they dropped us off and Kevin handed me Wendy's panties with his phone number on it. As soon as we were in the gate Wendy was hugging me thanking me and kissing me. I knew everyone of the boys cum was somewhere on her but I kissed her and held he tight so she knew everything was all right.

Wendy knelt and gave me a lovely head job swallowing everything again and apologising that I had to wait so long. We both went into the water and held each other as the sea washed us and then to bed and we slept like logs.

The next morning over breakfast Mary was curious about Simone and worried I was being ignored, or more so that I would be upset that she was focusing on her getting cock other than mine. She suggested I could join in, hold her hand and kiss her while other men pleasured her or even help them out by liking her while they fucked her or got them hard for her to use.

Mary was very casual about how horny I was when she played and how she wanted me to engage more and do whatever I wanted too. She kept probing about what I enjoyed about seeing her with other men, why my cock was always hard when I saw this.

After a while she asked if I just got turned on doing what she said.

"Yes," I replied. Mary continued,

"Good, so it shall be now but don't ever not do what I say."

"I won't, I promise," I said,

"Darling, you know how kinky I can be, do you really agree to do anything I want?"

"Yes," I said.

"Good, come and lick my pussy then." Mary ended our brief chat and she pointed to the bed where I laid back and she straddled me and ground her pussy into my face.

"Get your tongue right in there and see if you can taste any of the boys cum from last night," she said, continuing, "see if you can clean it all out baby, be my pussy cleaner. Clean all my lovers cum out for me, learn to get my pussy all clean for anyone who wants to use it. I will be embarrassed now if someone wants to have me and they don't get a clean pussy to use, it will be your job now Darling. Make sure your Wife is always ready for other men's cocks. Your cock is throbbing as I tell you what you will do Darling, you relax and I understand. You will never have to ask for what you want, I will know and make sure you get to do it," she said.

I was so horny and I loved the mental thoughts of Mary with her lovers and me having to clean her out. Just then I heard Kevin calling out for Mary from the door and Mary calling for him to come in.

As I heard Kevin and some other people enter the bedroom Mary just told them to fuck her, letting them know I would keep licking while they did. Mary told me after that she had invited any of the boys who were staff at the resort to have some fun before they started work so 4 of them came. Mary also spoke with Simone who came with them too and watched as each of the boys fucked Mary doggy and I licked her clit while they did it, Mary loved encouraging them and me and also enjoyed each time one of them pulled out and their cock slipped into my mouth, towards the end this was happening all the time.

Each time one of them came in her she would encourage me to clean her up for the next, her and also Simone at Mary's request, would repeat,

"Clean up cuckold, get your Wife's pussy all clean for another lover."

I had never really experienced Mary like this and although it wasn't a shock I was trying to come to grips with how humiliating she was towards me now. My confusion was in that she would tell me how my cock reacted each time she did thus making her do it all for me and not just her. Simone even giggled and agreed with Mary how my cock pumped when she spoke to me and how hard it was each time I cleaned out one of the boys cum.

After each of them had fucked Mary and I had finished cleaning her last load Mary got off walking them to the door to thank them and to encourage more visits. I couldn't hear all the conversations from the bedroom but I did hear Simone and Mary planning some tourist trips and shopping, they had struck up quite a friendship in the matter of a day.

"Darling, can you make Simone and I a coffee? Just bring them out we're going to go for a swim then sit outside." Mary called out.

As I heard the door close I went in to make the coffees for the girls. I hadn't really thought much about what was happening as it all came about so quickly. To be honest most of the time I was either drunk, hung-over or not 100% sure what was playing out so it was easier just to let Mary take the lead. She was right that my cock was telling her what I wanted but my mind still hadn't caught up with that and I was feeling very vulnerable about everything. For the life of me I couldn't get the taste of cum out of my mouth but did just step back mentally and accepted that I would follow Mary on what she wanted.