Chapter 8
The plane flight they took to Iowa was boring and bumpy, and they were tired when they got in, and though they were due to meet with the buyer whom they had met in New York that night, they called him and postponed the meeting until the following day. They got a bad feeling from the town, as if they were eyed suspiciously, for being from the East, for being women who ran their own business, and so on.
They found, as they tried to relax in their hotel room, that they were longing for the panty clad ass of Brent, longing to spank it, to watch it turning red and sore from the attentions that it was getting. They felt their cunts getting a trifle moist from these thoughts, but they were so tired that soon they were in bed, and slept dreamlessly until the following morning.
When they met with the buyer they said that they had come simply to check into some details, such as exactly to which stores certain batches were to be shipped, but in fact they wanted to nose around the operation, to look at the flagship store, to see the main offices. They were not happy with what they saw. The store was too neat, too well stocked, as if business was dead slow. And the traffic was light, and they heard enough bitching as they walked around to confirm their suspicions. Sales were way off, as they found simply by walking to the employees cafeteria, and seeing the figures for the previous day, which were down roughly forty percent from the same day in the previous year.
Now they had a real problem, for they were almost sure that they would not get the cash for the goods, or at least they would not get it on time, and that that would screw their situation, since they had had to go out on a limb with a couple of banks to get the big order ready. They did not know what to do, and they thought of taking some sort of legal action, of demanding payment before other creditors, but then they realized that there were probably many others to whom the chain owed money, and the priority of their claim would be low. They did not even know if there was enough cash around for the stores to meet everyday expenses, and things looked rather bad. They were out to dinner that night, and planning to go back to New York the next day, when they saw an elderly gentleman eying them and smiling.
Remembering what had happened with Slocum in New York they did not pay any attention to him, but then they heard people whispering about him, and realized that he ran the chain that was, potentially at least, going to give them so many problems. So they thought that they should go and talk to him, for they knew that he would be their last hope. He was dining alone, and they did their best to smile at him, and to look as if they would like nothing more than to be in bed with the old fart, sucking his wrinkled cock.
In fact they were appalled that someone could run a business so badly, and they felt as if they would like to simply make a scene in the restaurant, where the food would not have passed muster in a Forty-second street hotdog stand, and which was filled with people who looked as if they fucked once a month, under the covers, lights off, missionary position, she not moving and wishing that her duty was done soon, and he going to the bathroom with a magazine.
But the old man was smiling at them, and then a waitress brought over a note, in which the two of them were asked to join him. They sat down and smiled.
"And what are you two lovely ladies doing in Cedar Rapids?" he said, with a fatherly smile.
"We're on some business," said Ann, and then continued, saying, in a coy and girlish voice, "but we're so tired of that now, and a girl can't think about her work all the time, especially when she is in the company of such a distinguished looking gent as yourself. My, this certainly is a nice place."
Sofie had trouble keeping a straight face, for Ann was doing a small town accent, roughly Kansas, and doing it well, and they could see that the old fart was falling for it and that his cock was starting to swell in his pants.
"Why it certainly is a pleasure," he said, "it certainly is a pleasure to meet two women who are so well-bred. Where are you gals from?"
"Why we're from Hutchison Kansas," said Ann, and smiled.
"Why would you like to come with me and go dancing to some easy music? They say that when Jack Slater's orchestra does The Blue Danube why those violins just float the dancers right on off the floor." And he chuckled indulgently.
"I'm tired," said Sofie quickly, "but go on Ann, don't mind me.'"
The gentleman smiled, Sofie drifted off, and he rose, taking Ann's arm, and they went to his Seville, which he steered slowly toward a hotel in the center of town. Soon they were waltzing, and the old fart's cock was pressing hard against Ann's belly. She knew that she would go with him, and she wondered what his fantasies were, for she knew that if she did something that he had hardly ever done, but had dreamed about, then she might have a chance to squeeze him for some cash. But for the moment she took it slow, dancing to the awful scraping of cheap violins.
He invited her back to his place, explaining that his wife had died three years ago, and soon she found that she was sitting next to him on a couch that was deep and soft, in crushed light blue velvet and with fake antique legs. She flexed her feet, and she saw that his eyes lit there, on her pretty toes, and she knew then that she had him, and she felt good about it.
"Do you like my shoes?" she said coyly. "I always wonder if men appreciate the care that I put into selecting them. You know, I just feel so sexy in the right shoes, just like these." And before he could answer she was standing in front of him, and she was taking off her blouse, and she raised the stiff nipple of her right tit to her mouth, and she sucked on it slowly, sensuously, rolling her tongue around and around it, liking the way that it felt. The blood throbbed in it, and she felt her nipple getting even harder as she sucked on it. The old fart's cock was throbbing in his pants, and she saw that he was rubbing it through them, and she knew that in a few minutes he would be so hot that she could get him to take it out, and then she would slowly dominate him, until he wanted to crawl in front of her.
Her cunt was getting wet as she realized how much power she had over the little shit, and she raised now her left breast to her mouth, and she sucked that and then she played with her tits as he watched. She moved close to him, and she gave him a tit to suck, and his mouth closed on her nipples as if her tit was his only source of food again, and she reached down as he sucked, playing with his cock through his trousers. He was panting, and she worried for a moment that he might have a heart attack, but he seemed healthy enough, and she did not really care.
She saw that a small wet spot had appeared at the place where his cock bulged the farthest out of his pants, and she knew that he was ready. She stepped back, and she took off her skirt, and then her black silk panties, and his eyes followed the panties as she took them off. She dropped them, with a little laugh, into his lap, and he moaned with lust when he touched them.
He raised them to his lips then, licking them, kissing them, loving the way that her smell lingered in the material. Then he rubbed the garment all over his face and she knew that all his secret fetishes, all of the desires that pulsed in him, were coming out.
She laughed to herself, and she pulled up a chair and sat down facing him.
She spread the lips of her pink cunt, and she slipped a finger in herself, and slid it in and out of her. Her slender digit made soft slurping sounds as she worked it in and out of her dripping twat. He put down the panties, and looked at her hard, his eyes glazed with lust, his cock threatening to burst out of his pants, his collar wet with sweat and his breath coming hard, as he would soon.
Ann was hot and lusty, and she added a second finger to the one that she was slipping slowly in and out of her cunt, and she liked the way that that filled her hole some more, and she started to moan, and she thought of a hard cock filling her. She sighed and shifted her lush hips against the chair on which she was sitting, and she saw that he was burning with passion. As she looked hard at him, and worked her fingers faster in her gleaming moist cunt, she saw him fumbling with his zipper, and then he took his cock out, and it was decently hard, and was moist with the fluids that had dripped from it, and he started to play with it as he looked at her.
She smiled at him, and she flexed her toes, and his eyes dropped to them. She loved it, loved that he was now transfixed by her feet, and did not look for a while at the wet cunt that she was playing with. She rubbed her cut for a little time, but she did not want to come, for that would give him a measure of control, would make him know that she was getting real pleasure from what they were doing, and she did not want that, for she knew that she could not stand him.
He was moaning as he worked his cock, and he knew that soon he would shoot, soon he would come all over his pants, and he thought for a moment that that would wreck them, but then he thought that he could afford it, and then he looked again at the pretty painted toes that she was flexing for him. Suddenly he fell to his knees, and started to kiss her feet. It was more than she had hoped for, and she wiggled her stockinged toes under his tongue. He loved the smell of her feet and her sweaty hose, and soon the reinforced toe of her stocking, since she was not wearing sandal-foot stockings, as a kind of protest against the city in which she was, was soaked with his spittle. Then he raised his head, and he grunted and then he was coming, shooting all over the rug. He came hard and when he was done he collapsed back onto the couch, and fell asleep almost instantly, and she sat down to wait for him to awaken.
He was awake in a couple of hours, and he looked at her pathetically, and she knew that it was time to tell him about the deal that she and Sofie had with his stores. But he was so tired that she could tell that what she was saying was not sinking in, and so she told him that she would see him for lunch the next day, and he agreed, and also agreed that it would be best if she went back to the hotel for the night. He drove her to a bar, from which she called a cab to her hotel.
Sofie was asleep, and Ann did not wake her, but the next morning they discussed what to do with the leverage that they now had with the old fart. What they were hoping is that he had enough of his own money to pay their bill, for that was the only way that they saw to get out of the mess. So when she met him for lunch Ann told the idiot just what the situation was, and he turned out to be putty in her hands, for when she said that not only would she spend the coming evening with him, but that she could arrange for women, for a fee of course, to be with him for whatever time period he was willing to pay for, he agreed to pay them out of his personal monies. Ann and Sofie left Iowa happy with what they had accomplished, and now they knew that there were no obstacles left to continuing Brent's training as a maid.
They had left him in charge of the apartment when they had gone, and it was neat, and well-kept when they returned, and they saw that he had gotten enough pleasure out of his female clothes that he was wearing them all the time. He was properly submissive when they came in, and they were happy that they had such a well-trained, cross-dressing slave. They though about punishing him right there and then, about making him kneel before them, clad in his nylon panties and bra, about making him lick the floor while they beat him. But, though their pussies were getting wet as they thought about that, they did not bother with it that night, as they were too tired from their journey. But they had a certified check for the order, and they knew that it was good, and the next day they deposited it, and though they knew that they would not be fully happy until it cleared, at least things seemed to be pretty much under control. Work went quickly for both of them on the following day, and they knew that that night they would get back down to training Brent, who had had a rest from his punishment while they were away, but who now needed their instruction.
By the time that they were ready to go back to Sofie's apartment their snatches were so wet that their underwear was soaked, and the driver of the cab in which they rode to Sofie's place kept trying to pick them up, and they flirted with him a little, amused, but they had no intention of letting him touch, them, for they had a cross-dressing slave to punish.
When they got to the apartment, Brent was not in sight, and then they heard the moans of furious masturbation coming from the bathroom. There they found him, dressed in high-heels and a black bra, jerking his cock hard into a pair of Sofie's panties that he had taken from the hamper. They laughed for a moment, but then they grew serious, for they knew that such actions could not go unpunished.
They made him lie the floor of the bathroom, and they took turns standing in their high heels on his back, and they liked the red marks that their shoes left on his skin. He hurt from what they were doing to him, but his cock, which had been hard and throbbing when they had caught him playing with it, was still erect against the cold floor on which he was lying, and somehow the pain that he felt from their shoes was erotic more than it was agonizing. Finally they were done walking on him, and they knew that the next punishment that he would get would be to take the heels of their shoes, four in all, up his ass-hole.
His cock was still hard as he felt Ann's strong fingers greasing his ass-hole, and as his face was buried against the floor he did not know that they were going to put up his ass, and he hoped that it would not be too big, but nonetheless got very hot from the thought of being penetrated there. Then he felt shoes against his buttocks, and then the heel of a shoe was sliding into his ass-hole, and he liked that, since it was thin enough so that it hardly hurt at all, but it was erotic, and he wanted to start to hump his cock against the floor, and knew that if he did that he would come soon, but he did not dare do it without permission. Ann and Sofie took turns working the heels of their shoes in and out of the ass of their slave, and he moaned with passion as they did so. The movements that they made, the shovings in and out of shoe leather in ass-hole, pushed his cock, just a little against the floor, and he kept getting close to coming, and then slipping away from the edge. He loved being a slut of a slave, dressed in women's clothing on the floor.
Finally they grew tired of fucking his ass-hole with the heels of their shoes, and they decided that he would now have to wear some more clothing besides the shoes and underwear that he was already sporting. So they led him to his room, and made him put on not his maid's outfit but rather a skirt and blouse and a necklace, and then they made him go to the living room, where they tied his hands behind his back, and had him kneel at their feet.
His cock was still hard, and it made a tent in the front of the skirt that he was wearing. And he was hot from being dressed the way that he was and he moaned with lust as he felt the power that they had over him, the two women who were controlling his life now. He wondered what was in store for him, and he knew that whatever it was, no matter how harsh the punishment was that he might have to bear, he could take it, and that he would like it, like serving them, like bending, like a pliant reed, to their every whim. For a while they were silent, except for the soft sounds of nylon; rubbing against nylon as they swung their legs and looked at the slut.
"I see that the little girl is excited again. I am really starting to think that she spends far too much time thinking about sex. What shall we do with her? Perhaps some heavy whipping, my dear?" And with these words Sofie smiled at Ann, who mused for a moment, hand on her chin, before replying.
"Yes, I think that a liberal application of the birch to the bared buttocks, back, thighs, and worm of a cock of the slave would be in order. Let us begin."
Brent's cock throbbed even more as he heard the two of them saying these words, and though he knew that the punishment that he would get would be harsh, he knew that he could take it, and that basically it would excite him, especially since it would take place while he was wearing some items of female attire. He heard rather than saw one of them get up to get the rod, for they had made sure that he did not look higher than their feet as he knelt on the floor. He longed to touch his erect cock, that was still pushing with lust and passionate longing against both the nylon of his panties and the fabric of his skirt, but he dared not. Then he heard the one who had left to get the rod come back into the room and he knew that soon the next punishment of the night was to begin. He was hot and could hardly wait for the song of the rod on his bare and quivering flesh.
He felt one of them lifting his skirt, and then pulling down his sheer black panties, and he liked the way that the smooth surface of the panties felt as they slid down over the cheeks of his ass, those cheeks between which the heels of two pairs of shoes had so recently penetrated, and which now were to redden and blister and burn beneath the thin rod that Sofie was swishing, experimentally, through the air. Brent heard the sounds of the instrument, and they excited him even more than he had been. His cock was really dripping now, and again he thought about how he wanted to play with it, and he moaned and sighed as he was careful not to look up, and he grunted with lust.
Then he heard the thin cane whistling through the air, and then it was biting into the soft exposed flesh of his buttocks, and he grunted with the sting that it imparted to his skin, but he also felt a thrill of pleasure run through his aching loins at the pain that he felt. Again the rod came down, and then he felt some more pain, and soon he was being hit hard on the ass, so that the pain was so bad that his cock started to droop a little. But the one who was hitting himit was Ann, but he did not know that, as he still had not looked upsaw that his pleasure was starting to ebb, and slowed the force and the pace of the whipping, or rather the caning, that she was inflicting on him, not so much because she liked to give him pleasure, but because she knew that unless his cock was hard he would not be able to take as much pain as she was prepared to give. Ann bent and rubbed the warm pink flesh of his ass, and soon his cock grew full erect again as she rubbed his flesh, and he knew that soon she would begin to hit him again.
And, sure enough, once again the cane hissed through the air, and as he heard the instrument coming down he tensed his ass, and then it hit him, sending a thrill of pain admixed with pleasure through his body. All at once, somehow, he was sexily aware of the feel of the bra that he was wearing, and of the smell and the feel of the rayon of which his blouse was made, and suddenly, perversely, he found that he wished that he were wearing perfume, expensive perfume, Joy or Shamade or Arpege. But then these thoughts were driven from his mind as the rod came down again on his ass and his buttocks were whipped until Ann was satisfied with their particular shade of red.
Sofie, who was watching this latest phase in the evening's festivities of flagellation and cross-dressing, felt the moisture starting to flow more freely in her cunt, and she moaned a little, and reached under the skirt that she was wearing in order to touch her pubic mound through the thin, soaking wet fabric of her purple panties. She sighed with how good that felt, and she knew that she was so hot, from watching the punishment that Ann was inflicting on her slave, or rather their slave, that she would have to come at least once before she took her turn with the whip.
She looked hard at the red ass of the slut, and she could not resist then pulling off her skirt, and then her panties, and then she was slipping first one and then two of her strong fingers into her wet, creamy, hot and dripping cunt, and she was sliding them in and out of her, thinking of a cock. She thought for a moment of the various dildos that she had, and wanted to get up for a moment and get one, and plunge it hard into the pulsing pink grotto of her cunt, but she was so far gone with lust that she knew she needed to come, and come long and hard, first. She was moaning loudly now, so much so that Ann heard her, and stopped hitting the slave, her face flushed with the exertions that she had been making. The two dominant women smiled at each other, and they sniffed deeply, getting hotter from the smell of their moist creamy cunts in the air, and they knew that pretty soon they would have to suck each other off. That would mean that they would have to forgo, for a while, the pleasures that they got from punishing their cross-dressing slut, but that could not be helped, and besides the pleasure of a warm female mouth and tongue on a wet twat was not to be dismissed lightly.
Sofie was still finger-fucking her cunt, and Ann watched with parted lips, panting a little, and knowing that it would not be long before she was playing with her own cunt, as a prelude to the passionate sixty-nine in which the two of them, the two hot mistresses, were soon to indulge.
Brent enjoyed the cessation of the whipping that he had been getting, and stayed quietly in position on the floor, and he too could smell the wet cunts of the two women whom he was serving, and he liked knowing that he was giving them pleasure, though he knew that part of the game that they were playing meant that they would not show it.
"Baby, play with it, slip your hot fingers in and out of that creamy cunt. Mmmmmm, I know how good that feels. Play with your clit babes, play with it hard, make yourself come for me, will suck it. Do it baby, do it hard."
Sofie was so hot that she could not find any words with which to reply to those of her friend, and she simply moaned more loudly. She shifted her ass more rapidly against the seat of the chair on which she sat, and she sighed with lust, and she knew that it would not be long now before she came and came hard.
She knew that it was time to start playing with her clit, and she took her fingers out of her pussy, and licked them, liking the taste of her thick juices, and then she pulled back the skin around her hard clit, and she started to rub it hard, and she gasped with lust at the way that that felt. She arched her back, and her lush breasts, already swollen with lust, swelled even more, and Ann could tell that her friend was only seconds away from coming. And as Ann watched a deep flush spread over the upper half of the ripe body of Sofie, and she moaned and then the first spasm of pleasure hit her, and she was into all of it.
She gasped, she shook, her head rolled around on her neck as if she were a puppet with broken strings, and she kept up the pressure on her clit, so that she kept on coming, on and on, sighing and moaning and crying out, softly, with the pleasure that was rushing in hot waves through her body. Ann's cunt was so wet that she started to touch it as her friend came, and she forgot, for the moment, about her slave.
Brent's cock was really jumping now, and he rubbed it from time to time, being .careful not to get caught. But there was, at this point, little danger of that, for the two women who had enslaved him were now busy with each other, sighing and moaning with desire. Sofie's passion was starting to ebb, and she took her finger away from her clit, and she opened her eyes, and she smiled at Ann.