Hattiesburg to the High Seas : Day 3

Day 3 Island

Karry woke up, grabbed a freestyle breakfast and then put on her new swimsuit and packed her beach bag for the excursion to the private island. She knew her swimsuit on her body would attract lots of men today. It was just a matter of culling the herd to prevent wasting time on those with nothing to offer her. As she was leaving the ship, she saw Clint, the black football coach she had met the day before. “Clint, are you going to the island to work on your sun tan?, she asked. He replied, “Already got the tan taken care of, but I’m hoping to find some white chicks with a hankering for black cock”. “Well, said Karry, how about starting the day with a bang? I have always loved big, black cocks, so if you’ve got that to offer, let’s take the second shift to the island and the first trip around the world in your bed?” Clint said, “My bed is not real big”. Karry said, “How big is the floor?” Clint said, “Let’s go, and escorted Karry to his cabin. Once inside, Karry stood on her tiptoes and kissed Clint deeply with lots of tongue fucking action for at least 10 minutes. Clint then backed off and unzipped his shorts revealing a huge, black cock that must have been 10 inches long and 4 fingers wide. “Do you think you can handle this?”, asked Clint. Karry replied, “Sweety, I may only be able to get half of it in my mouth, but I guarantee you I can get it all in my cunt. Your balls will be swinging against my asshole in no time flat.”

Karry dropped to her knees and cupped his balls in her hand as she licked his cock. She then took the bulbous head into her mouth and started sucking and licking as she moved her mouth further down his cock. When she got a little over half of it in her mouth, she withdrew and then drove her head forward until all but about two inches was in her mouth and throat. She kept this up for about five minutes and then Clint yelled that he was going to cum. Karry kept sucking and locked her lips around his cock and swallowed as he exploded in her mouth and throat. “Breakfast of Champions”, Karry yelled, “Now get those clothes off, Sweety, I want that black monster in my cunt.” Karry slipped off her designer swimsuit, picked up a pillow and,placed it on a small table , bent over the table and looked by over her shoulder and said, “I like it hard, deep and dirty, Sweety, so satisfy Mama”. Clint proceeded to pound her cunt for twenty minutes, switching positions four different times. After cumming three more times, Clint dropped Karry on the bed and said, “Thanks, Karry, now I’m going to get a shower and catch the second ferry to the island. Good luck on your money quest and if you strike out, come on back toward the end of the week and, if I’m not busy, I’ll give you another ride.” Karry replied, “Thanks, Sweety, but I never strike out”.

Back on the island, Janet had gone snorkeling while Terry and Sally had met some men from the group and were drinking and lying out in the sun on the beach. When Janet returned to shore, she joined the group and asked if anyone had seen Karry. Everyone in the group laughed. Sally said ,”Wherever she is, you can bet she is on her back, on her knees, or some other position none of us have ever heard of”.

The girls were not to see Karry on the island that day. After cavorting with Clint, she returned to her cabin to shower and reapply her make-up. While she was in the bathroom, the ship steward came in to check the room. Karry heard him come in and peeked out the bathroom door. He was young, probably in his mid-twenties, Spanish, tall and dark. Kerry couldn’t resist. She walked out of the bathroom wrapped in a towel and then pretended surprise when she bumped into the steward and the towel dropped. Karry said, “Well now that you’ve seen it, you might as well taste it”. “So sorry, madame, I didn’t think anyone was in here”, said the steward. “Please, I will just leave now”. Karry would not let him leave and when he protested, she told him he would either do what she told him to or she would report him to security and say that he tried to rape her.

“Who do you think they will believe, a bank officer or a cabin boy”, she said. “Oh, please no, you remind me of my grandmother”, said the steward. “I’ll bet your grandmother doesn’t do this for you”, said Karry as she pushed the young steward back on the bed and unzipped his uniform pants and fished out his cock and engulfed it with her mouth. Just then there was a knock at the door and the linen maid announced herself and opened the door. The young steward, seeing his chance, jumped up and ran out the door and the linen maid left the linens on the table and said she would return later, then beat a hasty retreat. Karry laughed her ass off, saying, “They don’t make stewards like they used to”.

Karry then went looking for the Swinging Singles Cruise Director, Barry Rothstein. She found him by the pool sipping a Long Island Tea. She sat down beside him and ordered a Margarita. “What’s up, Karry?”, asked Barry. “Well, usually every cock on the ship when I walk by”, replied Karry. Barry was in mid-sip of his drink and almost choked when he heard her reply. “Barry, you have all the info on the singles group, so I know you can help me find what I am looking for and that is a rich man who thinks with his cock and doesn’t ask many questions”, said Karry. “I have plenty of money of my own, but I prefer to spend men’s money and I always reward them for their generosity”. Barry was a little flabbergasted and replied, “I really don’t know much about the financial condition of group members, but I would be glad to help you meet some of the gentlemen in the group”. Karry replied, “A gentleman is the last thing I am looking for, I always have been able to, and still can, get any man I want. I just don’t want to waste time.” Barry told her, “I really can’t help you with that, Karry, but I wish you luck in your search.”

Karry was really pissed off with Barry’s lack of assistance. He was a cute young Jew boy and she would have rewarded him for the information with a good fuck, but now, he was off her list of fuckees for the week, and it was his loss.

The first ferry from the island returned and Karry saw Janet and Terry? “Where were you?”, they both asked. “One beach is pretty much like any other, I decided to relax by the pool and do a little Plan of Attack research”, said Karry. Janet and Terry told Karry about Sally meeting a really nice man on the beach and that she was going to dinner and to the musical in the ship theatre tonight with him. Karry said, “I hope she keeps her eye on the prize, we are not looking for nice guys, we are looking for rich, horny guys that can be very generous. Look, I have already fucked every worthwhile man in Hattiesburg and taken a few of them for big bucks, so I am looking to widen the pool of potential suckers, or maybe I should say suckees.”

At dinner, Karry spotted an empty chair at Richard, the retired Judge’s table. She sat down and used her best southern drawl and eye flutter as she told Richard how handsome he looked tonight. They made light conversation during dinner and Karry removed her left shoe, lifted her foot onto Richard’s leg and wiggled her toes as she moved her foot toward his crotch. Richard finished the meal with a big smile on his face and asked Karry if she would join him at the musical later this evening. She accepted and suggested that they meet in the main bar about an hour before the musical for a few drinks. Richard thought this was a great idea.

As Karry headed for the bar, she saw Sally and her new friend Eddie. Sally introduced him to Karry who proceeded to grill him with questions designed to judge his “ship playmate potential”. Sally was a little embarrassed by this and steered Eddie away from Karry, saying they were late to meet some of Eddie’s friends. Kary was disgusted with Sally. She thought to herself, “Some people just are incapable of learning life’s priorities.”

Richard was waiting in the bar when Karry arrived. They had a couple of drinks and then walked to the ship’s theatre to watch the musical. As soon as the lights, dimmed, Karry put her right hand in Richard’s lap. Richard was a little shocked at first, but then a big smile came across his face. He knew he was in for an exciting night and he deserved one. It had been five years since his wife divorced him after catching him with the latest of his string of law clerks, male and female, that he had bedded. In the divorce, she not only got all his money, but also the scandalous testimony not only of Richard’s serial infidelity, but also of his bisexuality, spread through the courthouse like wildfire. The Head Judge had asked him for his resignation, but Richard had refused. Two months later, Richard had showed up for court visibly drunk and verbally abusive to everyone in the courtroom. Someone summoned the Head Judge who walked into the courtroom with a Sherriff’s Deputy and not only had Richard removed from the Bench, but led away in handcuff’s to the county jail next door to the courthouse. Richard spent 24 hours in the drunk tank and when he got out, was instructed to report immediately to the Head Judge.

The Head Judge told him, “Richard, you are finished. I wish I could thank you for your service to the county, but it has been horrible. You are and always were a political hack who never deserved to be a Judge. I have notified the state bar association and they are going to start disbarment proceedings immediately. You are a shame to the profession and you will never work in it again.” Richard slunk out of the office and returned to his rented apartment and began drinking. He didn’t really stop until he had no money left to buy booze. He contacted his son, who agreed to pay for treatment in a substance abuse clinic. When he was released as a 12 step recovering alcoholic and sex addict, he had no job and no hopes for one. Again, he contacted his son, who refused to help him any further. He then went to his ex-wife and begged her for her help, crying his eyes out. Finally, she had agreed to stake him to the money to take this cruise in hopes that he could find a wealthy matron to sponge off of for the rest of his life. This was basically his last chance.

Now, Richard sat in the ship’s theatre with a reputedly wealthy lady running her right hand along the shaft of his cock and licking her lips and laughing with him. She certainly was not a beauty queen, but money will make a man overlook nature’s inequities like a pinched face and hooked nose. He had heard some rumors from the other guys about her being a “golddigger”, but he had no gold for her to dig and he had learned over the years that con men and con women were very susceptible to being conned themselves. He’d give her an “open marriage”, matter of fact, he would prefer she was fucking someone else, because that would give him some time to “upgrade” to something better looking and younger. He just wanted her money, not all of it, just enough to keep him in style.

When the musical ended, Karry whispered in Richard’s ear, “Do you have a roommate?” Richard said, “Yes, unfortunately”. Karry said, “Don’t worry, I can handle that, let’s head for your room?” When they got to the room, Karry told him to check to see if his roommate was there and Richard checked and found the room empty. “Watch this”, said Karry and she reached under her dress and pulled off her satin panties and tied them around the door handle. “That’s the international signal for Don’t Come In”, said Karry.

Once inside the room, Karry undressed which was easy because all she had on was her dress, no bra, and her panties were tied on the doorknob. Richard looked her over, saw her small, saggy boobs and wrinkled skin. Maybe when he turned out the lights, this would be tolerable. He quickly undressed, flipped the light switch off and joined Karry on the bed. She grabbed his cock and squeezed it saying, “Oh, Richard, I have wanted you since I first met you. It has been so long since I have been fucked and I want you right now. Now, get down between my legs and lick Mamma:s cunt.” Richard did as he was told, but the smell was very unpleasant, even though her cunt had obviously recently been recently Brazilian waxed, so he didn’t stay there long. He moved up and cupped her tiny titties in his hands and squeezed them. “Oh, Sweety, squeeze my titties harder, I love it when a man squeezes my titties and my nipples.”

Richard had taken 50 miligrams of Viagra two hours before and his erection grew as Karry sucked his cock into her mouth. Karry then licked his balls and sucked each one of them into her mouth. She then placed two pillows on top of each other on the bed and lay face down with her hips on the pillows and her ass pointed toward the ceiling. “Don’t get any ideas, Sweety, my asshole will be all yours for the taking someday, but right now I want you to concentrate on relieving the itch in my cunt. Richard climbed between her legs and inserted himself in her cunt to the hilt with one push. She was either extremely wet or extremely loose. He felt like he needed to tie a board on his ass to keep from falling in. “I can do this and pretend I like it”, he told himself because it would be worth it to have money and his old lifestyle back. “Oh God, Oh God, Oh Baby, fuck me harder, Sweety, pound my pussy”, moaned Karry.

Richard thanked God for the Viagra or else he would never have been able to get it up or keep it up looking at this woman’s body. Richard finished, then immediately got up and poured them some wine in two drinking glasses. “Here’s to you, Karry, that was wonderful”, said Richard. Karry drank her wine, then rolled over and went to sleep. Richard sat there on the bed listening to her snore and wondered if her money would really be worth putting up with her. Thankfully, he fell asleep himself.