Caribbean Nightmare


By WimpHub


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 Fiance, 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!"

I got the cock in my mouth feeling disgusted, and Lisa told
me to put my hands behind my back, as it made me look more
submissive. I felt foolish, humiliated and degraded with my
head bobbing backwards and forwards on a big black cock,
with my wife watching and taunting me. After a time, Lisa
held the back of my head, and encouraged Ben to fuck my face
hard until he filled my mouth with cum. This he eventually
did after about half an hour. I was then sent away so that
they could carry on their wedding night fucking in private.

After this humiliating evening, the following days followed
a similar pattern. Lisa would spend the days with me,
flaunting her naked body at me but not allowing me to kiss
her, or touch her in any way other than sucking her slime
filled cunt. She would also taunt me endlessly about the
prowess of her black lover, and how happy and satisfied he
made her. At night we would sit in the bar until Ben picked
her up. I noticed that they began to stay longer and longer,
kissing and groping each other right in front of me. They
would then leave hand in hand, with Lisa wishing me a
satisfying jerk off. I could not believe I had allowed
myself to get into this situation.

One evening after they had left, I saw a young woman enter
the bar alone. She was about 21, the same height as Lisa
with long jet-black hair. I noticed she looked faintly
oriental, perhaps Japanese. I walked over to the bar where
she had sat down and introduced myself. She seemed very
friendly, and told me her name was Anna. Apparently she had
an English father and Japanese mother, which accounted for
her stunning oriental looks. She told me she was on holiday
with a girlfriend, who had decided to go to bed early.

Things were going really well, I bought her several drinks
and the conversation was flowing nicely. During our chat,
she constantly crossed her legs, showing me plenty of thigh,
and leaned forward regularly to give me a good view of her
ample cleavage. I had the feeling that I would definitely be
able to get her back to my apartment and get rid of some of
my frustration. I was just about to suggest that we adjourn
to my place when she got up to go. I touched her arm to try
and stop her.

"I thought we might go back to my place and have some fun,"
I suggested.

"Do you seriously think," she laughed. "That I would sleep
with an inadequate man with a dick so tiny that he has to
get a real man to fuck his wife on his wedding night?" She
obviously knew all about my situation.

Her cruel taunt, combined with my frustration made me angry,
and I stood up to block her path.

"Listen you fucking little prick teaser," I snarled. "I
don't have to take that from you!"

Then everything went black for a second, as Anna brought her
knee up viciously between my legs causing incredible pain in
my balls, which seemed to travel right up my stomach. I
dropped to my knees, involuntarily crying out in agony. Anna
walked away without a word, leaving me feeling sick and the
few people left in the bar sniggering.

Next morning, I heard Lisa coming in and got to my knees
ready for her. As she came towards me, I noticed she had a
face like thunder. Instead of lifting her dress, she lapped
me savagely across the face, backward and forward at least
four times.

"I have been talking to Anna," she snarled. "You tried to
fuck her last night." 

"But Lisa," I pleaded. "You won't let me..."

"Now listen," she interrupted. "I am the only one of us who
is getting any sex on this holiday, I will not have you
cheating on me!"

"I'm sorry," I whimpered.

"Not as sorry as you are going to be," she assured me. "Now
get your face in my cunt and clean me. This is the nearest
thing to sex you are going to get."

That evening in the bar, Lisa left me sitting at the table
when Ben arrived. Instead of leaving, they went to the bar
and began chatting to a couple of black guys and two of the
local black girls. About ten minutes later, I saw Anna
arrive with another young black guy and they joined the
company. It was getting late by now, and the other guests
had left. The bar doors were locked, and Lisa came over to
me.

"We are having a little private party," she told me. "Come
and join us." I walked over with Lisa to the others at the
bar.

"You know Anna of course," Lisa said. "You tried to get in
her panties last night."

"Yes," Anna continued. "I feel bad about abusing your poor
balls, so I am going to let you have a look at my pussy."

She lifted up her short dress to reveal her pussy fringed
with jet-black hair. It was obvious she had been fucked very
recently.

"It's full of cum I'm afraid," Anna announced somewhat
superfluously. "Perhaps you would like to get down and clean
it for me."

I hesitated, and felt strong male hands pushing me to my
knees. Anna grabbed the back of my head, pulled me to her
pussy and ordered me to suck.

"Oh look," she said, as I lapped away at her. "See how
greedily he eats that cum. I think he must have been born
for this."

"With his tiny dick, he certainly wasn't born to fuck," Lisa
observed, and all those gathered round laughed at me.

When I had cleaned Anna up, she turned to Lisa and asked if
she really made me suck cock. Lisa confirmed that she had.

"I would love to watch that," Anna said enthusiastically.
"Ben could you stick your cock into the pansy's mouth and
make him suck you off?"

Ben stepped forward, unzipped his fly and released his cock.
Grabbing me by the hair, he forced it into my mouth and made
me suck.

"Come on," chided Lisa. "You know the position, hands behind
your back!"

As I knelt in that submissive position, my head bobbing
backwards and forwards, the women began to taunt me, Anna in
particular.

"Look at the little faggot," she sneered. "How could you
marry a wimp like that Lisa?"

"I have my reasons," Lisa replied enigmatically.

Once again, Ben lasted a long time and when he eventually
shot his load into my unwilling mouth the others gave a
spontaneous round of applause. I was then thrown out of the
bar as the others partied way into the night.

On the day before we were to go home, I had arranged a coach
trip for Lisa and I to have a look around the island. It was
a very early start, so Lisa told me to pick her up at Ben's
place. When I arrived, Ben told me to take a seat. As I sat
down, I could hear from another room the sound of bedsprings
taking a real hammering. This was accompanied by a loud
female voice. The sounds were a mixture off gasps, sobs and
a sort of unintelligible pleading. It was unmistakably
Lisa's voice. After a time, the sound changed to rapid
panting followed by a loud scream, signifying that orgasm
had been reached. It went very quiet then, and nothing
happened for about ten minutes.

Eventually, Lisa emerged in a sort pink robe, which showed
almost all of her gorgeous legs. I felt my cock twitch as
she sauntered towards me.

"Ah you are here," she said. "I expect you heard all the
noises Dave here dragged out of me with his magnificent
cock. He is not quite as good as Ben, but then nobody I have
ever met is. Now, are you ready to get down and clean me?"

"Can't we go back to the apartment?" I asked, not wanting
the two men watch me.

"No," Lisa replied emphatically. "Dave is very keen to watch
you suck his cum out of me."

Resignedly, I knelt down and sucked yet another man's cum
out of my wife. When I had finished I made to rise.

"No," Lisa stopped me. "Now clean Dave, and suck another
load out of him."

After I had completed my distasteful duties to the
satisfaction of my wife and her two lovers, she announced
that she wanted to spend the rest of the day with them, and
I should go on the trip on my own.

Finally, the holiday was over, and we were on the plane
home. Once we were airborne, I ordered champagne for Lisa
and myself. Clinking glasses with her I said:

"To be honest, this holiday has been a nightmare for me but
now I am happy that were are going home to start a normal
married life, and I can at last have my wedding night."

"It depends what you call normal," Lisa remarked. "You see
when we get back to the big new house your daddy bought us,
Ben will also move into it, and into my bed. So you see you
will not be getting the wedding night you have been longing
for, in future any sexual relief you get will be courtesy of
your right hand. You will have a regular opportunity of
watching me getting it from Ben, and of course there will be
plenty of sucking on smooth, cum-filled pussy for you. I
also intend to make you an expert cocksucker. It will be
your party piece for Ben and I, and all our friends."

"I don't understand any of this," I exclaimed. "What the
hell is going on?"

"Let me explain it to you slowly," Lisa said quietly. "I
have worked for your dad for 5 years, and he knows me very
well. Ben did not work for the resort; he also has worked
for your dad for the past 10 years, and has been my
boyfriend for two.

"Your dad approached me to say that he thought I would be
the ideal wife for you, someone who would not take any
nonsense and would be able to keep you in line. He was
pretty sure that you would fall for me, and he was right. He
also asked me to check out whether you were a fit person to
hand the company over to you when he retires. After watching
you for the first couple of months, I reported back to your
dad. I told him that I was prepared to marry you, purely as
a business arrangement, and I told him that I would show him
clear proof of what a weak-willed, gullible waste of space
you are." She pulled out an envelope and handed it to me.

Inside were a series of pictures, obviously stills from a
video. There were shots of me on my knees sucking cum out of
Lisa and Anna's pussy and sucking Ben's cock. The final one
showed me watching passively as my new bride was being
fucked by Ben.

"Although you never saw them," Lisa advised me. "Your Mom
and Dad have been on the island the whole time, and they
have both seen these pictures. When your Mom saw them, she
made me promise that I would never allow you sex with me
again, as you don't deserve it."

"So what happens now?" I asked, totally bewildered.

"You will continue to work for the company," she told me.
"But you will work properly. In keeping with your talents,
you will act as errand boy and general dogsbody for the 30
girls in the typing pool. I believe quite a few of them have
been fucked and then dumped by you, so I am sure they will
work you pretty hard. Your generous monthly allowance will
now be paid directly to me, along with my salary. You will
be comfortable, and you will eat and dress well, but you
will not have control of any money. While at home, you will
serve Ben and I in any way we require."

"And if I refuse?" I asked defiantly.

"Then we will have your cock locked up, and you will be
denied any relief until you comply. That again was your
Mom's idea. I am sure the girls you abused would be
delighted to cocktease you unmercifully, and I would
certainly enjoy doing it when you get home. You can of
course leave, but you will go without a penny, and with your
lack of any sort of talent or ability, I am sure you will
starve in a month."

"No," I said, after thinking it over for a while. I don't
believe any of this, my Mom and Dad would never treat me
that way."

"Take a look, two rows back," Lisa replied.

I stood up, and looked back down the plane. There sitting
together, were Mom, Dad and Ben drinking champagne. As they
saw me, the three of them raised their glasses and smiled.


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