CUCKOLD STORIES
CARIBBEAN NIGHTMARE
My name is Tony James. I am 35, the only son of Edgar James, the multi-millionaire owner of a string of large department stores situated in all the major cities in the country. Up until a few months ago, I had the world at my feet. I worked for my dad's company, although worked is probably too strong a term. Knowing I would eventually inherit the family millions, I would bully others into doing my work, while I worked my way through all the young, beautiful women who worked at our Head office.
I had never had any intention of settling down, not when I could have my pick of the women courtesy of the power of my father's money. It all changed when Lisa arrived to work in the Administration department, having transferred from one of our stores up north. Just 22, with long dark hair framing her face, she looked like a younger version of Sigourney Weaver. She was quite short, about 5'4", but with a figure that men drooled over. Pert breasts, just the size I like, and sexy, beautifully shaped legs which were enhanced by the short skirts she liked to wear.
I was smitten with Lisa immediately, and set out to seduce her. I soon found though, that she was totally unimpressed by who I was or the family money. I also found that, because I had never had to try too hard before, my attempts to be smooth and seductive were somewhat pathetic. I would often sidle up to her, and make some suggestion or other, and she would put me down in a haughty and sneering manner in front of other employees. What I found strange was, that this seemed to turn me on. Being treated like dirt by this strong woman awoke a submissive side in me I had never experienced before, and only made me more determined to have her for myself.
After a couple of months of persistently trying, she finally agreed on a date with me. It went fairly well, and she began to be warmer and friendlier towards me. Gradually we built up to a full-blown relationship, although it was very much on her terms. Lisa was obviously used to having her own way, and because I was obsessed with her I went along with whatever she wanted. She controlled everything, where we went, when and where we had sex, and how often. Believe me, it was not nearly often enough for me. I soon decided that I had to marry her, to make sure I could have her when I wanted, and because I knew I could not bear to be without her.
Luckily, she agreed eventually to my proposal, and I remember we had a very boozy evening together to celebrate. I remember as I got more and more drunk, she began to ask me more and more personal questions in order to get to know more about me. My answer to her question about my favourite sexual fantasy was later to come back and haunt me. I drunkenly told her that the thought of her spending the night with a well endowed man, and then coming back to me and making me clean the cum out of her pussy really drove me wild. At the time she just smiled, and moved on to something else.
We decided we would get married in the Caribbean, just the two of us, as neither of us wanted a lavish affair. Lisa picked up some brochures, and pointed out a resort catering for people who liked to wander about completely naked in the sun.
"I have always wanted to get an all over tan," she told me enthusiastically.
Though I was not so keen on the idea, I agreed, because as I said, what Lisa wants, Lisa gets. I made all the arrangements; we would stay for two weeks, getting married at the end of the first week. I must admit, as the time to go approached, I was getting pretty excited about the whole thing.
We arrived at the Island resort quite late on the Friday evening, and went to bed almost immediately, being tired from the long flight. We got up bright and early next morning, with the bright sunlight flooding our room. Lisa was keen to get out by the pool as soon as possible, I think she wanted to give everyone the benefit of her gorgeous naked body. I told her that I was not comfortable about that myself, and would wear my shorts.
"Probably just as well," she observed. "Your dick is a bit tiny, isn't it darling? I wouldn't want you getting an inferiority complex!" She had never made such a comment before, and I found it a little hurtful.
We found a spot by the pool, and Lisa stretched out on a sun lounger. Her naked body looked absolutely fabulous, and I noticed quite a few men taking a second look as they passed by. This gave me an uncomfortable feeling of jealousy, particularly as Lisa smiled at quite a few of them. After we had sat for a while soaking up the hot sun, Lisa told me to go get her a drink.
When I returned, Lisa was staring intently at a well-built young black guy, also naked, who was chatting with a friend at the other side of the pool. I looked over, and was immediately drawn to what was hanging between his legs. Although limp, his cock hung down quite a way, and looked very thick. I had never seen anything that size before.
"Will you take a look at that," gasped Lisa. He is hung like a donkey! What woman would not like a piece of that!" I felt very uncomfortable at her speaking in this way, particularly after her rather cruel comment about my cock a little earlier. Her next comment made me feel even worse.
"You remember your fantasy about me being fucked by a big man and forcing you to clean me afterwards? I think we just might make that come true during this holiday!"
"No Lisa," I protested. "I didn't mean I really wanted..."
"Get me another drink," she snapped, cutting me off.
When I got back this time, Lisa was with the black man, and they were chatting and laughing. She stayed with him for a good half-hour, and I was not at all happy to see her stroking his huge biceps and broad chest as he devoured her naked body with his eyes. Eventually she returned to me with a huge grin on her face.
"His name is Ben," she informed me. "And he is absolutely gorgeous. I am delighted to say he wants to fuck me, and he is going to pick me up in the bar at 10 tonight."
"You can't be serious," I protested. "You are my Fianc‚e, we are getting married on Friday!"
"Oh stop whining," she said. "I'm just helping you live out your fantasy. Besides, what's one night, when we will have our whole lives together? Look on it as a last fling."
"I can't say I am happy about it," I told her, feeling miserable.
"No, but I will be," she smiled. "That cock looks even more impressive close up. I can't wait to see it hard and erect!"
We were sitting in the bar, when Ben came over promptly at ten. Lisa got up as he approached, put her arms around him and gave him a long, open-mouthed kiss.
"Are you ready?" asked Ben. Ignoring me completely.
"Are you kidding?" she replied. "I have been soaking wet all day thinking about tonight. Let's get back to your place, so I can feel that cock in my mouth!"
As I watched her walk away hand in hand with her large, soon to be new lover, I realised that I did not want the fantasy to come true, the idea of my Lisa with another man made me feel sick. I went back to our apartment, and spent a largely sleepless night imagining Lisa in Ben's huge arms, knowing that I could not hope to compete with him in the cock department. Finally, I got to sleep, and the next thing I remember is being woken up by Lisa, who was happily singing to herself.
"Come on," she said cheerfully. "Down on your knees, time to complete your fantasy."
"No," I replied grumpily. I don't enjoy that fantasy anymore, I won't do it." She leaned over me, and spoke menacingly.
"If you want to see anything of me at all during this holiday, I suggest you get down and clean me up now!" "He shouted.
Reluctantly, I dropped to my knees in front of her, and she lifted her short dress, revealing that she had left off her panties. Her pussy looked really puffy, as though it had recently seen a lot of robust action. I could see drops of white at the entrance, and her pussy hair was matted. Tentatively, I leaned forward and began to lick her.
"Suck all of Ben's lovely cum out of me," she ordered. "He went to a lot of trouble putting four loads into me last night, and another just ten minutes ago. God, Tony he fucked me rigid I have never had such fabulous sex in all my life. Compared to him, cum sucking is all you are fit for. Oh by the way, Ben wants me to stay with him every night for the rest of the holiday, I think he likes the fact that I will do absolutely anything for him in bed!"
"No, please!" I exclaimed. You are my girl, when am I going to get to have sex with you?"
"Not until we get home," Lisa replied firmly. "I am not the sort of girl who can sleep with two men at the same time, and given the choice I would rather be fucked by Ben any time."
I was in shock, trying to make sense of it all. I again reminded Lisa of the fact that we were supposed to be getting married on Friday, and asked how she could sleep with someone else after she became my wife. She responded saying that I would have to accept being a cuckold for the first week of our marriage, and that considering we would be together for 40 or 50 years, one week wasn't too much to put up with.
"That is assuming you still want to get married," she said.
"Of course I do," I assured her.
"Then you must accept my terms," she insisted. "Oh and I shall want my pussy sucked clean every morning, like today. It's the only way you can make sure I come back to you every day. Now, I need to catch up on my sleep so get dressed and sit by the pool, I want to be left in peace."
I went out, bought a newspaper and sat by the pool feeling wretched. How had I allowed myself to get in this position? Lisa knew how desperate I was to keep her, and was using that to walk all over me. My misery was further compounded when Ben walked past me as I was reading. He flashed me a smug "I am fucking your woman" smile at me, and chuckled as he went by.
It was two or three hours later before Lisa emerged naked from the apartment and plonked herself down on the sunbed next to me. I looked at her lying there, and wanted to fuck her so badly, but knew she had made her mind up to deny me until we got home.
That evening went much the same as the previous one. Ben came over at 10, only this time instead of going to his place; the two of them stood at the bar. They were laughing and kissing openly, and the black man was groping her young body. I could not stop myself from looking at them, and occasionally Lisa would look over at me, smile, and rub her hand up and down the front of Ben's trousers. She was taunting me, and flaunting her infidelity in front of me and everybody else in the bar. I could not help notice several people looking at me, and then whispering to each other and laughing. Finally I could take no more, and made my way off to bed. I could hear Lisa and Ben laughing at me as I left the bar.
Next morning, when Lisa lifted her dress for the ritual cum sucking, I noticed her pussy was totally bare.
"You have shaved your pussy," I exclaimed.
"Yes," she replied. "Ben wanted me to do it, and as he is the one giving me all the pleasure he gets what he wants."
It felt strange licking her bald pussy, as I had always preferred it with pubic hair. Obviously I no longer had any choice in the matter. When I had finished, Lisa announced that she wanted a shower and asked me to wash her back.
I did this for her, and then she turned round and told me to soap her breasts and pussy. I was naked like her, and she watched amused as my little cock began to get stiff. She was teasing me unmercifully and enjoying every moment. She made me dry her with the towel, and when I had done she took my cock in her hand, making it twitch violently.
"My, you really do need to come don't you?" she laughed.
"Yes I do," I replied expectantly.
"Well you had better go to the bathroom and pull yourself off, while you picture Ben's huge black dick stretching my pussy as he fucks me until I beg for mercy!" she told me cruelly, and went back to bed laughing loudly.
We were making final preparations for the wedding, and I again asked Lisa if she was really going to sleep with Ben on our wedding night. She confirmed that she was, saying there was no possibility of me having her whilst we were on the Island. For some reason that I still cannot rationalise, I found myself asking if I could at least be there and watch.
"What?" Lisa screamed. "Tony I knew you were a pathetic no dick wimp, but a pervert as well? You actually want to stand there and watch while another man fucks your wife on your wedding night?" I hung my head, my face bright red.
"Alright," she went on. "I will ask Ben if he will allow it, but I warn you it will be humiliating for you I will see to that!"
The wedding day arrived. The ceremony was set for seven in the evening, when it was a bit cooler. Saying it was bad luck for me to see her before the wedding, Lisa had stayed with Ben since the previous evening. She arrived with him just before seven.
Lisa stood next to me in the little open building that resembled a bandstand. She looked fabulous in a very short, low cut white dress.
"This is funny," she laughed. "I am standing here about to marry you with another man's cum running down my leg!"
The minister arrived, and we were ready to go. Several of the guests from our hotel had gathered to watch the ceremony, and most of them knew very well about Lisa's activities with Ben, as they had not been at all discreet. Lisa then made sure that everyone knew the situation.
"Hey Ben," she called. "As you are taking care of the wedding night duties you should be standing next to me too!" Ben grinned and came to join her, as everyone watching laughed. When the service was over, and I was told I could kiss the bride I turned to my new wife. She turned and allowed me just to kiss her on the cheek, then turned to Ben and kissed him passionately to cheers from the assembled guests. We all returned to the bar for the reception. Speeches were dispensed with, and we just cut the cake before the dancing began. Lisa had a great time dancing with everyone but me, saving most of the dances for the man who would consummate the marriage on my behalf. At about ten, Lisa came over to me.
"Are you coming then?" she asked
"Yes," I replied meekly.
"Right, well you had better do exactly as you are told," she warned. "Or I will see that Ben beats the shit out of you!"
Lisa and Ben announced they were leaving, and I followed a few steps behind.
"Are you going to watch, to see how it's done?" laughed a young black girl as we left, causing hilarity amongst the crowd.
Once in Ben's bedroom, Lisa ordered me to strip, keep my mouth shut, and my hands away from my cock. Then she and Ben slowly undressed each other, passionately French kissing the whole time. Then Ben sat on a chair, with my new bride kneeling before him. I was told to kneel right next to Lisa as she took hold of his cock and stroked it to erection. I was amazed at the size it grew to, it must have been at least 11", and nearly as thick as a beer can.
"Isn't it magnificent?" cooed Lisa. "If any woman tells you that size doesn't matter, they are lying. This horse cock has done things to me that you could never dream of."
My wife then began to plant kisses on the sensitive thick bulbous head of Ben's cock, telling him all the time how much she loved it and how it felt when plugged into her cunt up to the balls. She then spent a long time lovingly sucking as much of his cock as she could into her mouth, as well as licking all the way up and down the long shaft and taking his balls into her mouth.
When she had finished, she stood up and straddled Ben's legs facing me. She told me to kneel in front, so that my face was inches away from the erect cock. She took hold of it, and lowered herself slowly on to it until she was completely impaled.
"Oh Tony, you have no idea how good that feels deep inside me," she told me, raising herself almost off him. "Look at my juices coating his cock, it will be a while before you get this treatment. You are going to have to sort out that hard on yourself when you get back to the apartment."
Lisa kept up the taunting as she bounced up and down faster and faster on her lover's cock. She became more vocal as her orgasm approached, finally crying out at just the time Ben emptied his balls into her womb. She sat for a while regaining her composure, then lay on the bed spreading her legs.
"Clean up time cuckold," she announced.
Embarrassed with having Ben watch me sucking his cum out of my wife, I leant forward to complete the now familiar task. When I had done, Lisa got up and to my surprise pulled me by the hair until I was once again kneeling before Ben. He stood up, and Lisa told me to suck him clean too.
"No please," I begged. "You can't ask me to do that!"
"I am not asking," she declared menacingly. "Now get your mouth round Ben's cock and suck him until I tell you to stop!"
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