Chapter 4
Back in London Ann was ready to begin the punishment of her slave. Basil knelt before her and kissed the leather of her boots. He could feel her toes flexing as her cunt-smell started to fill the air of the room, and his cock was hard, and he longed for the sting of the whip. He knew that she would give him what he needed, and he hoped that she would be cruel, for then he knew that he would get the maximum amount of pleasure out of what she was going to do to him.
He had been beaten all throughout his boyhood, most often by cruel women, and all of them had taken a sexual pleasure in it, and often had.played with his cock while they hit him and he had sensed their lusts, and from that time on his sexuality was inextricably linked to being whipped. He continued to kiss the boots of the hot bitch who was going to dominate him, and he longed for the kiss of the whip.
"Present your ass for my whip, you little worm, and you must play with your cock while I hit you, but you must not come." He knelt, facing away from her, and he moaned with lust as the first harsh blows hit his wailing ass.
She stood facing him, so that she could let him look at her, and she reached over and behind him to whip his ass, which was soon red and burning from the punishment that she was giving him. And while she hit him he was playing with his cock, and it was soon slick with the juices that were leaking from it, and she liked the way that it looked, and she liked the sounds that it made as he played with it. She hit his ass for a long time, and he took all of it, liking the pain, needing the pain, and Ann's cunt was wet and hot when she finally decided to stop whipping his ass.
"Come on my boots, slave," she said, and he moved into position and he moaned with pleasure and with the need to come and worked his hard dick faster. She inhaled briefly, and flared her nostrils, and she watched his cock, wanting to see the semen shooting out of it, loving it when they came in front of her. It was the power that she liked, the power and the sex, the knowing that the slave was hers. Hers to whip, hers to fuck in the ass with a dildo, hers to punish and abuse.
He grunted, and his hand flew even faster over the hard shaft of his dick, and then his cock got a little bigger, and the hole at its end opened some, and she knew that he was about to do it, was about to come on her boots. She felt her cunt getting even wetter as she watched him and then the first burst of sticky come was coming out of it, all over the soft and supple leather of her boots. She flexed her toes as he came, coming hard all over the leather. Finally he was done, and she ordered him to clean her boots with his tongue, and she felt even hotter as she watched him.
"Do you want to suck my wet cunt? Yes, I know that you do, I know that you want to lick it, to taste it, and I know that you want to lick my ass-hole too. Mmmmmm, I know that it would taste good. But you are a naughty boy, and I do not know if I should let you lick it. First you will have to take a dildo up your ass, and then we shall see. Here is some oil. Lie on your back, raise your legs, and work the oil up your ass-hole until you can get three fingers inside yourself. If you do not do this, I shall simply ignore you for the rest of the night."
She leaned against the edge of a table, and she played slowly with her wet cunt as she watched Basil starting to oil his ass. First he used one finger to work the grease up his rear, and that went in easily enough. Then he moaned with pain and with pleasure as he added the second finger, and he worked the two fingers in and out of his ass-hole with real vigor. He did that for a long time, and Ann was very hot, and she slipped two fingers into her cunt, and she was so wet that she felt as if she had used some of that oil herself.
Then he grunted and he got the third finger up in his ass-hole. It hurt him, and it was a tight fit, but he knew that that was what she wanted, and she moaned with lust as she saw that he had been able to comply with her orders. His cock was hard again, even though he had come so recently, and she knew that he wanted her to touch it, and she loved the feeling of power that she had as she looked at him.
"Very well slave, I shall fuck you in the ass-hole with my strap-on dildo, so you may remove your fingers from your hole." He did as she had said for him to do, and he lay on his back, in just the position that he had been lying, and then he moaned as she strapped on the rubber cock, and then she was on him, as if he were a woman and she a man fucking him in the missionary position.
She worked the cock into his ass-hole, and she felt his cock hard against her belly, and her tits pressed into his chest, and she was hot, and she reached down and played with her clit as she dildo-fucked his ass-hole.
"You must not come slave, even if you like the way that my soft belly rubs against your hard cock. And you must he still while your mistress fucks you."
He moaned a little, and the friction of her belly against his cock felt good, so good that he did not know if he could stand it. But he managed to hold back, and she fucked him hard, and she worked her clit while she did that and she was hot and she knew that it would not be long before she came.
She moaned then, and she bit her lips with the lusts that filled her. Her cunt was gooey and hot, and she knew that if there had been another man there she would have fucked him, have taken his hard cock deep inside her belly-mouth, and fucked him until he was dead to the world, and his cock hung limp and useless in his groin. But she would not do a slave the honor of fucking him, at least not like that, and she had to content herself with playing with her clit. She started to come, and she shook quietly as she did that, and she fought to keep from showing just how good she felt, for she did not want her slave to know just how much pleasure she was getting.
Then she pulled the rubber dick out of his ass-hole, and she gave it to him to lick, and he moaned as he sucked it, and his cock was hard and throbbing. She wondered if after he came again he would have enough stamina to come a third time, and she knew that she would keep him going after she jerked him off.
She waited until he had cleaned off the dildo and then she knelt beside him and she started to play with his cock, subtly and slowly. He moaned with lust, and he knew that he was helpless in her hands, and that he would come no matter what she said she would do to him if he did.
"Does my naughty pig like it when his mistress plays with his hard cock? I know that he is going to come all over his mistress' hands, and I can tell that he is going to shoot. I know that he-likes to spend all day playing with his cock, and that he dreams of putting it in me, of fucking my wet cunt. But he knows that that is not allowed. Mmmmmm, that feels good, my little shit, doesn't it? Yes, here it comes, here comes the sperm."
He moaned with lust, and then he started to shoot, and he came very hard, although there was not as much juice in him as there had been the first time. He moaned and shook with lust, and when he was done he licked off her hand, and she moaned a little since she was very hot, and she stood over him where he lay on the rug.
She could not help it, she just had to play with her wet pussy, and she stroked and rubbed it, and she came again and again, moaning with lust. She laughed out loud as she saw that his cock was getting hard again, but she was tired and she did not want to take the trouble to make him come again, and so she left him, and they said goodnight.
The next day passed quickly, and she was packed by the late afternoon, and she slept until one in the morning, when with the wig on her head she set out for the north of England, and then Scotland. The drive was long and boring, and they did not stop all the way to Glasgow, except for food and gas and the bathroom. The driver took her to a room where she slept, and then she cleaned herself up, and before she knew it she was on the plane for New York, and she arrived on Sunday.
But let us go back now to the training of Brent, and follow it through to the time of the phone call that Ann made to Sofie. .
On Friday night Carla and Jane and Sofie were hot for their slave, and they knew that too they would have the hard cock of Jack to fuck and they knew that it was time to begin. Sofie brought Brent in and the other women looked him over. He was naked, and the female clothing that he was to wear was waiting for him.
"I see that the little shit has a hard-on, and no one has said that he is allowed to have one. Well, I think that I shall whip him now, before he gets to put on the lingerie and the outfit that give him so much pleasure. Look at how the worm is hard from thinking about the feel of nylon against his skin. All right worm, bend over for your spanking."
Brent did so, and Jane brought her palm down hard against his ass, and he moaned with lust, and then with pain as the force with which she hit him increased. His cock stayed hard however, despite the pain that he was feeling, and she hit him harder and harder, for she wanted his cock to go down. But he liked the pain too much for that, and even when she was done he was hard.
Jane was disappointed in her slave, and she looked to the others for some ideas.
For a moment not one of them spoke, since they were too preoccupied with the sight of the red ass of the slave. Although Brent was in a world of burning pain, his cock was hard, and he knew that if he were allowed to come he would come hard, and he hoped that he would serve Sofie and her dominant friends, as well as he could.
Finally Carla spoke. "Let us dildo-fuck the little shit. All right slave, bend over so that I can oil that ass-hole of yours, and I do not want any shit out of you, or it will go very hard with you." The other women watched with faces that were masks of lust as Brent bent over and spread the cheeks of his ass. They gazed for a moment at the tight ass-hole, so wrinkled and so brown, that soon was to be penetrated and raped with the dildo. They loved the power that they felt as they watched, and they knew that their cunts would be even hotter and wetter when the slave was well-fucked. He moaned with lust as he felt the strong fingers of Carla starting to grease his tight ass-hole, and he buried his head in the carpet, serving her.
Carla shoved two of her greasy fingers into the slave-ass that was hers for the moment, and the other two women watched with parted lips, panting and grunting with the lusts that filled them as they watched the violation of the slave. He was in pain now for Carla was working her fingers hard in and out of his ass-hole, and she soon had added a third finger to the two with which she had started to penetrate him. He could hardly take the three greasy digits up his ass, and for a few moments he wondered if they were not going too far. But then he grew used to the feel of the fingers up his ass, and his cock, which had been drooping a Utile, rose once again to its full state of erection. He longed to play with it, but he knew that as he had not been given permission to play with it he dared not touch it.
"Yes, fuck the ass-hole of the little shit with your fingers, do it to him hard and fast, make him feel it. Carla, put the dildo in, since it is big and hard and it will teach the little worm that we mean business." Carla nodded, but for a few moments she continued to work her greased fingers in and out of the slave-ass, since she was so hot from what she was doing that it was hard to stop. Finally she pulled her fingers out of Brent's ass-hole, and she grinned at her friends.
The slave did not move, but simply stayed in his place on the floor, and waited for the next assault on his ass-hole. It was not long in coming, for soon he felt the hard head of a huge rubber cock being pushed against the already violated entrance to his virgin ass-hole. He gasped with pain as it started to slide into him, and soon it hurt so much that it was all that he could do to keep from begging for mercy. The three mistresses, Carla who was fucking the slave's ass-hole with the dildo, and Sofie and Jane, who were watching, were getting so hot that it was hard to keep on punishing the slut. But they knew that they wanted to see him dressed as a woman, and that they would do that before they got around to satisfying the lusts that were burning their cunts. They watched with hard tits and wet pussies.
Carla had worked the hard artificial cock all the way up the ass-hole of the slave, and she left it all the way up for a while, and while it was in the ass-hole that was stretched so painfully around it she started to spank the ass of the slave. He was moaning with pain, and Jane saw with a grin that his cock was going down, and she knew then that they had the control that they wanted over the little shit.
Carla, having grown tired of spanking, went back to playing with the dildo, and she started to work it in and out of the tight ass-hole of Brent Miller. Still he felt nothing but pain, and he longed for the time when he would be allowed to put on women's clothing, for though that would be humiliating, it would not hurt. But for now he had to take the pain, and he did not know if he could do so for much longer. But after a while his ass-hole grew used to the intruder in it, and then Brent started to get hard again, and so Carla pulled the greasy dildo out of his ass, and then all three of the women watched with evident satisfaction as the slave was forced to lick the dildo clean. He moaned with lust as he did that, for he loved being humiliated like that, and he knew that if he were allowed to come that night he would come hard and long, from the punishment that he was getting. He looked up at the three women who were in control of him, and then as he saw that they were offended by that, he dropped his eyes and looked only at their feet. They flexed their ankles as he looked at them, and he felt his cock getting so hard that he could hardly stand it. He knew that he shouldn't, but he started to jerk-off.
"What., you little piece of shit, you subhuman turd, do you dare to touch that miserable cock of yours without the permission of your mistress? Carla, tie his hands so that he cannot touch his cock." And Sofie watched with a cruel smile as the slave had his hands tied, and then she and her friends knew that it was time to begin the dressing of the slave who was to be a maid. They made him put on the panties and the bra, and even though he was in pain, from the spanking that he had gotten and from the dildo that had been rammed up his ass-hole, he got so hot from the feel of the bra and panties against his skin that he soon did not care about the pain.
His cock throbbed against the nylon of the panties, and once again he longed to whack off, to play with his hard dick, and his mistresses knew that he wanted to do that, wanted to come for them, but they loved knowing that he was totally and completely in their power, and they laughed cruelly at the lusts of their slave.
"The little shit is hot, isn't he? I think it is time for the dress and the shoes, and then he can serve us with his tongue." When Jane had spoken the others nodded, and soon Brent was in heels that were painfully tight, and in a cute dress, a maid's outfit, black with a frilly white apron. He loved the way that it felt to be dressed like that, and now that the pain had eased so that he could hardly feel it he longed to serve Sofie forever, to be her willing slave. They made him walk around the room and laughed as he fell from not knowing how to walk in the shoes. Then they told him to bend at their feet, and he licked the shoes that they were wearing until the leather was shiny with his spittle. His cock pressed hard against the panties that he was wearing, and made a tent in the front of the skirt of his outfit. He knew then that dressing in women's clothes was the fulfillment of one of his most secret fantasies, and he knew that he had never felt as excited as he was at this moment. He moaned as he licked shoes, moaned with the lusts that filled him. He knew that he had to come, and desperately tried to rub his cock through the clothes that he wore, but they could tell what he was doing and soon they made him stop, and spanked him for a while for doing what he did. He ached then for they had hit him hard, and his cock drooped a little, but he was still so hot and so horny that he was desperate for sex. He wanted to suck them, to taste their flesh, to lick their gamy ass-holes. Their cunts dripped with passion.
Then Carla could stand it no longer, and she knew that she had to have a slave-tongue on her cunt. And she loved the way that the slave looked in his outfit, and she knew that she would have him suck her off for a long time. He moaned with lust as she spread the lips of her cunt, and she played with it in front of him for-a while, and she got hotter and hotter while she did that. She knew that she would let him suck her, for a long time, but for the moment she wanted to tease him and she laughed at the way that he looked at her. The other two women were also hot and he knew that it would not be long before they were sucking each other off.
Finally, after a long time of teasing, Carla was ready to have her slave suck her cunt, and she grabbed his head, and pulled him to her, and she moaned with lust as she felt the first warm touches of his tongue on her wet cunt. She locked her legs around his head, so that he could hardly breathe. She loved the feeling of control that she had, knowing that he would do anything for her, including suck her cunt for as long as she wanted him to. He was moaning with pleasure as he sucked her off, and his cock was very hard, and had made a wet spot in the front of his skirt. The other two women were ready to go, and soon they were playing with their cunts as they watched the slave, dressed in his maid's outfit, sucking Carla.
Sofie worked two fingers in and out of her dripping pussy, and she moaned with the lusts that filled her, that made her cunt so wet and her tits so hard. She rubbed the stiff nipples of both her breasts. She sighed and groaned with lust as she did that, and Jane, who was also masturbating, and hot, added her moans to those of her fellow mistresses. Brent thought that he was, as it were, in slave heaven, and he felt as if all that he wanted to do for the rest of his life was to suck the cunt of the hot bitch who, only so recently, had jammed a dildo up his ass. He could still feel a touch of the pain that she had inflicted on him, but it was mostly pleasure that he felt, pleasure at the clothes that he was wearing, and pleasure at the taste and the smell of the wet twat that he was licking. Carla moved so that her slave could lick her clit, and she was almost ready to come, and she raised her hips off the chair on which she was sitting, and she ground them hard against Brent's face. The other women were also close to coming.
"Suck my clit harder, you little worm, suck it and make your mistress come," said Carla, and the other two women worked their own clits harder as they heard her words. The air was filled with the sexy odor of wet cunt, and the sounds of passion that were in the room made Brent's cock even harder. He wanted to play with it as he sucked the cunt of the hot bitch who watched him cruelly, but he knew that it was not allowed, and so he could only moan with the lusts that filled him.
Then Carla was coming under his tongue, and she moaned loudly, and her large frame shook with the force of the passion that filled her. On and on went her climax, for she made sure that the mouth and tongue and lips of her slave did not leave her clit as she came. The other two women stopped playing with their wet cunts so that they could watch, and the both were impressed with the force of the pleasure that was shaking Carla. Brent hung on for dear life, sucking harder and harder, and hardly being able to breathe. But he did not care, and simply moaned with pleasure from the pleasure that he was giving his mistress. Finally she was done, and she smiled at the little worm, and she knew that she would let him play with his dick for her, that she would let him come on the rug and then lick it up.
But first she looked to the others for approval, and the two of them, being so far gone with lust that they could not speak, nodded their assent. And then Brent at last could touch his hard cock, and he was working it hard, and he loved knowing and feeling that he was in a maid's outfit, and that he was at the feet of three hot cunts who loved to humiliate and whip him. Although he had thought that he would shoot almost as soon as he touched his hard cock, he did not, and in fact jerked his cock for a while in front of the three women. They were hot from watching him, and came as they watched, and their cries and moans excited him greatly. He sighed and panted with the effort of working his hard cock, and his prick was wet with the juices that were leaking from it, and Brent's hand made loud and slurping noises as it slid up and down along the slick shaft of his cock. Harder and harder he worked it, and then he grunted and tensed and as his cock swelled just a little more all of the people in the room knew that it would not be long before he shot. The three women stopped playing with their wet cunts so that they could watch, and they had those expressions of total lust that glazed their eyes on their faces.
The room was silent, except for the sounds that Brent was making as he came closer and closer to coming. Harder and harder he worked it, and then as he held his breath his cock heaved and bucked, and then he was shooting onto the rug. There was an impressive amount of come, and the women watched with lusty delight as he emptied his loins in front of them When he was done they made him clean off the mg with his tongue, and they loved watching him do that, for they knew that the fact that he would do that meant that he was totally in their power.
When he was done he was taken back to his room, and tied to the bed for the night. The three women masturbated a little more, and then sat around chatting and drinking. Finally they left, and then Sofie started to wonder again about Ann, and despite the phone call she was worried, and she worried all weekend until Sunday.
On Sunday afternoon, early, Sofie was sitting and reading the paper when the phone rang, and it was Ann from the airport, none the worse for wear. She took a cab and arrived at So fie's about an hour and a half later, and the two women hugged each other for a long time.
"Oh baby, I was so worried. What happened? Tell me about it baby, and are you sure that you're OK?" And Sofie looked anxiously at her friend.
"Honey, I'm fine, but right now I am so tired that I can hardly think. Let me go home and sleep, and I'll see you at the office tomorrow. OK?"
"Sure baby, I'll have the doorman get you a cab." And Ann went home, and she fell asleep until nearly noon on the following day, and when she awoke it was as if the whole mess abroad had never happened, and she felt good, and she went to the office with her head high, looking good. There she told Sofie the whole thing, and Sofie shook her head in wonder at the fact that Ann had gotten away, and she knew that she would not let her go back to Europe for a good long time. The women then got down to business, and poured over the data that Ann had brought. Ann was ecstatic over the news of the big order that Sofie had gotten, and the two women knew that business would be good.
But in England a slimy character, who hung around the East End of London, and who would do anything for a pound or two, stepped to a phone booth, and called a number in Paris collect. He spoke quickly, and gave Jean's henchman Ann's New York address. Jean's aide promised the stool-pigeon an extra ten pounds.