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by Cristiano Caffieri

Gill Wingham preyed on vulnerable women. He was mostly unemployed and didn’t have a pot to … in and yet he spent a good part of each year in some tropical paradise.

His methodology was simple, he went all out to find some lonely plain Jane who looked as if she might have a few bucks and from thereon it was easy. On their first dates he would apologize for being strapped for funds but he would struggle to pay his share. After two or three dates he’d use his highly successful stock phrase, “If I had the money I’d take you to some tropical get-a-way and make love to you every day to the sound of the surf.”

In 75% of cases the woman would suggest that she could pay for such a holiday and off they’d go to Aruba, Cancun or Rio and fuck the days away. This enabled Gill to eat well, drink all the booze he could handle and lounge around in the sun flirting with some of the other girls. Some years he managed to squeeze in up to four such vacations. Of course when they returned home he would simply explain to his weeping victim that they were simply incompatible.

Living in a small city it was inevitable that word would get around but Gill was simply too stupid to think about that. The hairdresser for two of his “Sugar-Dollies” was intrigued that their stories were so similar and when she told them her suspicions it started the ball rolling for some sweet revenge.

After making some inquiries they found three more plain Janes who’d been duped and dumped by the lascivious lounge lizard. Put five very bitter young women together and you’ve got trouble. Morag, a woman who had spent three Martinique weeks with his cock in her mouth, was particularly vengeful.

“We should really nail this bastard,” she said, “He needs to be taught a lesson.”

Although it sounded like an appropriate punishment, after due consideration, “cutting off his balls,” was rejected as being a little extreme. However, Sabena came up with another method of emasculating him that sounded like fun.

“I have a friend who’s a professional dominatrix, why don’t we chip in some cash and set them up for a vacation together. I think she could make it hell for him.”

The idea was met with a round of applause and it was arranged for Helga, the woman in question, to call on his apartment to do a survey for her Daddy’s business and bait the trap. Sure enough Gill fell for it hook, line and sinker. And after just one date Helga suggested taking off for some exclusive resort for a two week love-in and he nodded his head so enthusiastically it nearly fell off.

Once on the isolated island of Yarabuko Helga began to show her true colors. As soon as they got into their room, ironically numbered 69, she slipped off her clothes revealing her black leather panties and bra. He was, to say the least, a little surprised by her choice of underwear. Then came the whip – she produced it from her luggage and smashed it a couple of times on the dressing table.

“What’s that for,” he stammered nervously, “Are you thinking of going riding or something?”

“I’m going to ride you, you horrible little turd because you are now my … a whole two weeks.”

Gill swallowed hard and even managed to force a smile, “Is this some kind of a joke.”

“Do you see me laughing?” she retorted, giving his buttocks a clip with the end of her whip, “Now strip off and get on all fours.”

It was only natural for him to be a little hesitant but he soon started to peel off his gear in response to another stinging clip from her crop.

Once naked and on all fours she climbed on his back and rode him around the room. His knees were sore and he was exhausted by the time she’d finished her little canter.

When she dismounted she didn’t let him get up but stood before him and stripped off her panties to reveal a substantial bush.

“Now lick it until I cum,” she yelled.

“Shouldn’t we shower first,” he asked cringing in case she delivered another blow.

“Take it as it is – or ain’t you man enough?”

Even a sniveling, cowardly … like Gill doesn’t like to have his masculinity challenged and so he moved up to her crotch, opened up her lips with his trembling fingers and inserted his tongue.

“Now lick it and lick it good,” she cried.

Being a dominatrix doesn’t mean you’re immune to a little sexual pleasure and putting aside his contemptible personality, her licker was a pretty good looking dude. As his tongue glided up and down her wet crack she began to tingle all over and tugged on his hair as she could feel her quim going into seismic overload.

As her orgasm lasted for some two and a half minutes, her long tongued … his face being smashed repeated into her oozing grove and he was finding it increasingly difficult to breath. When she let his hair go he collapsed onto the carpet completely fucked.

For Gill, every day proved to be more hellish than the next. As it was her plastic that was paying for everything he was not allowed to drink … and while she dined on 12 ounce steaks and lobster thermidor he was restricted to egg salads and the occasional Spanish omelet.

Back in the bedroom the torment continued. She would wake him at three o’clock in the morning and force him to jerk himself off over her tits. Most nights he slept sardine style with his ankles manacled to the bed head and his face in her muff.

After the first week Gill was beginning to show signs of cracking. He even considered trying to swim the hundred mile shark infested stretch of sea to the mainland. When that seemed a little impractical he turned his attention to the fattest, ugliest girl at that resort hoping he could con her into flying them both out of there – but she turned out to be a Lesbian. Eventually he broke down and cried and Helga began to feel sorry for him.

After phoning the girls it was decided that the punishment had gone on long enough and to let him spend the last few days in relative normality. That night in the restaurant, with one eye twitching nervously, he waited for his egg salad to be served. However, he perked up considerably when she ordered steaks for two and a bottle of very good wine. As he dug ravenously into the juicy Porterhouse and sipped on his 2009 Bordeaux, he couldn’t help but think this could be his “last meal.”

Perhaps she was planning to kill him by sexual over-stimulation; after all there was no law that said you couldn’t fuck a man to death. “But why was she doing this?” that was the question he kept asking himself. In the end he thought that perhaps she been let down by some scurrilous cad and she was now taking out revenge on all men.

He became even more confused when that night she put on some … lingerie, a few dabs of perfume and proceeded to kiss him passionately. It was difficult for him to respond because at any moment he expected her to pull a whip out of her cunt and begin to beat on his balls with it, or something equally insidious. However, instead of being confronted with “Helga the Terrible,” she became loving and sensitive and went down on him.

He’d had his cock sucked many times before but not the way she did it. She slid it between her full lips deep into her throat and twirled her tongue around it at the same time. When his cum started to move up his pipe he yelled out because he feared more punishment if he came in her mouth, but she sucked every drop out of him and swallowed it.

For the next few days he licked her body from head to toe, pounded her pussy and fucked her face, and it was heavenly. In spite of the great sex, when it was time to check out he wasn’t really sorry to say goodbye to room 69, but then he was not aware what awaited him back home.

Helga went with him to the apartment and when they opened the door there was a big surprise, the five girls all sat there waiting for him.

Forcing him down into a chair, his former victims offered him a deal. They would pay his rent, buy his food and a reasonable amount of … in exchange for him satisfying their sexual needs according to a schedule they’d drawn up.

Gill protested, saying that such a deal was beneath his dignity but when Helga produced her whip and started to lick the end of it he decided that it might be a reasonable arrangement. His only stipulation was that he was allowed to have a few days rest to recoup from his holiday. THE END

Copyright 2014 Cristiano Caffieri