by Emily Tilton
When she was told to spread her bottom-cheeks, Lauren had to do that, too, no matter how hot her face got. Mr. Killington could see her little anus, the place where he wanted to put his cock even though it would hurt when he thrust it in and out of her young bottom. Mrs. Fredericks could see the places she had waxed, because Mr. Killington liked a girl to be bare inside her panties, whether they were the cotton schoolgirl briefs or the lacy white thong that made Lauren feel like the time had nearly come to lose her virginity upon her owner’s hardness.
Only if I say yes, about my bottom.
A soft wail burst from her throat, then, for the terrible white plastic nozzle had touched her crinkly little dimple. Oh, why had she been made to prepare the enema bag and the nozzle herself?
Silly question. You know why. So you’ll think about it—and about what it means.
Lauren had to put the water and the soap in the bag, and mix it up, so that she would think about what sorts of things can go into a schoolgirl’s bottom, when the schoolgirl has been naughty. Lauren had to put the lubricant on the nozzle so that she would think about Mr. Killington’s penis, and what it would feel like to put the slippery stuff on a man’s cock, before it entered her most private place.
She felt her rectum go small, trying to push against the nozzle. “Relax, honey,” said Mrs. Fredericks. “I am going to put this in you whether you tighten or not, but it will be more comfortable if you push a little, and learn to take it gently, like a good girl.”
Lauren whimpered at that, and tried to relax. Did Mrs. Fredericks mean to suggest that having this enema constituted training for Mr. Killington’s anal penetration? Her brow furrowed deeply at the shameful thought. She pictured, instead of the white plastic nozzle pressing against her rectum, Mr. Killington standing behind her, holding her hips steady, pressing the big cock that Lauren had grown used to sucking, now, against the tiny hole. Part of her rebelled against the image, and tightened even more. Mrs. Fredericks clucked her tongue and pushed harder, and then another part of Lauren came out, and with a sob she did push, knowing she would have to push like this when her owner put his hard penis in her bottom, so that he could enter her and have the pleasure he deserved.
“There, honey. That is it,” the matron said, pressing the nozzle firmly into Lauren’s bottom, the little bulb at the end holding it in place. “Hands on the toilet seat, now.”
“Good girl,” said Mr. Killington, with such warmth in his voice that it drew another sob from Lauren as she obeyed and her punished cheeks closed around the invading plastic, feeling the hose that connected the nozzle to the bag of warm, soapy water enclosed within them.
“Mr. Killington, would you hold the bag, while I open the valve?”
Lauren heard shifting, sloshing. She thought she could hear Mrs. Fredericks’ fingers moving, as they grasped the little valve on the neck of the bag. Then, suddenly, she felt the warm water, and she moaned, because it felt so good. How could it feel good, to bend over the toilet so that a man and a woman could put things in your bottom?
“When the time comes for you to keep company properly with Mr. Killington,” said Mrs. Fredericks, “you will have pleasant enemas, to get you ready to please him. But today the pleasant part will only last a moment, because you were naughty this morning.”
Oh, so naughty, thinking about what it would be like when Mr. Killington bent her over not for punishment but for pleasure, thinking about what his cock would feel like inside her. Thinking about the cocks she had sucked in the past two weeks—the doorman’s, and Bill the personal trainer’s, and Mr. Graves’, and Yo’s owner Mr. Philips’, and of course, many times, Mr. Killington’s.
The water kept rushing in, and now her moans changed to pitiful cries of discomfort, because it was much too much, and she was much too full. “Oh, no. No… no…” she whispered. She bounced on her knees, then kept bouncing: she just couldn’t help it. Her bottom contracted on the nozzle, and she tried to push it out, but Mrs. Fredericks put her hand on the thing to hold it in place.
“There,” the matron said. “That is what naughty girls get, is it not, Mr. Killington?”
“Yes, it is,” he affirmed. “When a girl is caught with her hands in her panties, stern measures are required.”
Still the water rushed in. Lauren heard a high, keening sound coming from her, though it almost seemed to come from somewhere else. The feeling in her bottom was painful, though not agonizing, but the urgent need to sit on the toilet immediately, and the shame associated with that need made the discomfort absolutely terrible. She bounced and bent, clenching and unclenching her bottom continuously on the nozzle.
“Hold still, honey,” Mrs. Fredericks said. “You are just making it worse. We are almost done filling you up.”
“Are you going to masturbate without permission again?” Mr. Killington asked sternly.
“No,” Lauren sobbed. Oh, if only he would give permission right now! Lauren thought that might make it feel better—might even teach her a more important lesson than just having too much warm, soapy water inside her bottom.
The water stopped flowing. Mrs. Fredericks pulled the nozzle out, saying, “Hold it in, now, honey. Five minutes.”
“I’m timing,” Mr. Killington announced. “Stand up and turn around, sweetheart.”
“But…” She hadn’t thought of this, that she would have to straighten up, that she would have to look at them.
“The five minutes won’t start until you turn around, Lauren,” her owner said.
Lauren wailed, and began to lift herself, on jiggling knees, from the toilet seat. Immediately and instinctively, she put her hands behind her, to cover the valley between her bottom-cheeks, thinking that if she didn’t do that she wouldn’t be able to hold the water in.
“Turn around,” said Mrs. Fredericks.
That seemed like it should be easier, but it moved the fluid inside Lauren, and a little sloshing sound even became audible in the echoing tiled space. She gave a cry, and bent her head so that she wouldn’t have to look at them.
“I can’t,” she whispered. She thought the water would start to rush from her any moment.
“Cannot,” said Mrs. Fredericks severely.
“Cannot,” Lauren repeated, feeling her face pucker into a mask of woe.
“You can, sweetheart,” Mr. Killington said. “You earned this, and you earned your whipping. You’re going to be a very sorry girl when we’re done, but then it will be all over, and you won’t be naughty like that again, will you?”
“No, sir,” she said miserably, jiggling her knees and shifting her weight from foot to foot.
“Mrs. Fredericks,” he said then. “I can handle it from here, I think. Thank you.”
Lauren’s eyes darted upwards at this unexpected development.
“You are welcome, Mr. Killington. Lauren, be a good girl, now.”
“Yes, Mrs. Fredericks,” Lauren said dutifully, her heart beating faster as she wondered what would happen now.
Mrs. Fredericks closed the door behind her.
Mr. Killington said, “Play with yourself, Lauren.”
“What?” For a moment, Lauren forgot how uncomfortable the enema felt. She looked into his eyes and saw hunger and also a serious purpose.
“Masturbate for me now. Show me how you need it.”
Lauren bit her lip, and lowered her eyes again. She kept her left hand on her bottom, and moved her right slowly around her hip.
“Look at me, sweetheart,” Mr. Killington commanded, and she did. That little piece of obedience seemed to change things inside her, move them slightly off center, and then she thought she understood much better than she had before what it meant to belong to him. With her gaze locked on his dark eyes, her fingertips found her clit, and she cried out because the enema in her bottom and the smart from his big hand and the pleasure in front all came together. Lauren realized she was more aroused than she had ever been in her life.
Mr. Killington smiled. “Good girl. Sit
on the toilet now, let out your enema, and play with yourself while it happens.”
She did, instantly, and she groaned at the terrible, wonderful sensation. She kept looking into his eyes as the shameful sounds continued, as she whimpered her pleasure over them. She was so close to coming, now.
“Are you ready to take my cock in your anus?” Mr. Killington asked.
The answer burst from Lauren, and made her fall over the edge into her climax as she sobbed it out. “Yes, sir.”
“You’ll lose your virginity tonight, sweetheart,” he said softly, as the last of the enema trickled from Lauren’s bottom. “In front and behind. But I need to whip your bottom first. When you’ve cleaned yourself up, go to your bedroom and lie on the bed with two pillows under your hips. I’ll come in to give you the belt while you suck my cock.”
Lauren’s jaw dropped, but no words came out. How could something so terrible also sound so… right? The pure punishment she had thought she would receive had changed into something else, and the logic of her body defied any lack of logic her mind might have found in the proceedings.
She found, when she got to the bedroom, that Mr. Killington or Mrs. Fredericks had already put the pillows in place. All she had to do, though it caused a blush as hot as the sun, was to lie over them, naked, feeling how they raised her bottom to present it for discipline.
“Mouth right at the edge of the bed, nice and open,” she heard Mr. Killington say from the doorway. “Hands down next to your hips.” He closed the door behind him as Lauren obeyed. In his hand he had the heavy jeans belt, which he put, coiled, on the end of her bed. Then she watched him undress, all the way out of his suit, her heart beating very fast. She had seen him naked now half a dozen times, but never in her own bedroom in Mrs. Fredericks’ apartment—only in the penthouse. His cock sprang from his pants so long and hard that Lauren gasped.
Mr. Killington chuckled. “That’s your fault, sweetheart, and now you’re going to do something about it, while you get your whipping.”
Chapter Eighteen
John took the heavy belt in his right hand, doubled it, and wound it once around his hand. He moved up the bed, holding his cock in his other hand, loving the feeling of having his naked schoolgirl willingly in his power. Lauren looked so pretty over the pillows, waiting for her whipping, her eyes on his hardness just as they should be, that he couldn’t resist simply entering her sweet mouth, already so well-trained, and beginning to fuck her there.
She whimpered around the cock he had sheathed so pleasurably between the petals of her lips, and he brought the belt down on her bottom, so that the whimper became a cry of submissive discomfort. He put his left hand lightly on the back of her head, twining the fingers loosely in her wonderful auburn hair, just to keep her still as he enjoyed her mouth. A little groan of pleasure broke from his throat: Lauren had become a truly excellent cocksucker in only a couple of weeks—both Hank and Juan had said so, and John, though he expected himself to be biased on the subject, fully agreed.
He whipped her again and again, knowing that both because of the slightly awkward position in which he carried out the punishment and because he did not mean to make this discipline very painful she was finding her belt whipping much less severe than she had supposed. Certainly it could have no comparison to Mrs. Fredericks’ paddle.
The time would probably come, perhaps even quite soon, when he would have to punish Lauren severely—that often happened with the girls in the New Career Partners program when they realized how much freedom they actually had, and decided to test the boundaries. Today, though, after the enema and the yes that meant he would deflower her tonight, John only wanted her to have a nice, lingering warmth in her bottom to reassure her that her owner knew how to take her in hand when she played with herself.
He thrust in and out of her mouth a little more rapidly, irresistibly drawn toward the release that would let him think straight for the two hours before he took his girl’s virginities. The lovely wet sounds of a face-fucking rose in the little room. He brought the belt down, a little harder, and reaped the reward of Lauren’s wailing cry around his cock. In it he heard the wonderful mix of pain, submission, and gratitude that John often thought he lived for, beyond all things. To combine sound career guidance from successful professionals with erotic guidance from affectionate dominants seemed to him the greatest project in which he had ever had the luck to be included.
John gave his pretty schoolgirl the belt on her naughty bottom over and over now, admiring the lovely red streaks he left there, feeling his cock leap in her mouth as she writhed a little over the pillows, her little cheeks clenching in discomfort as she received the just reward for illicit self-pleasure. The orgasm began to seethe in his balls, his lower back, and he cried out at its power. Lauren, her face full of cock, her head held in place for his pleasure, made a sound that suggested pleased surprise—John generally remained entirely silent when he enjoyed her.
“Oh, good girl,” he said. “I’m going to fuck you so hard tonight in that sweet pussy.”
That turned Lauren’s little cry more ambiguous, but again he could hear the gratitude. The genius of Mrs. Fredericks’ approach struck him anew: giving the harsh paddling early and then waiting for Lauren’s need for complete submission to become unbearable, so that she would ask for permission to touch herself, be refused, and then be caught in the peccadillo. It had worked wonders, and John had reaped the benefits, and would reap the greatest benefits of all tonight in the penthouse.
He dropped the belt so that he could fondle her bottom, for the first time in the sexual way he had longed to do since he had first taken her over his knee. The sensation of the little belt-warmed cheeks in his hand, the sound of her cry of pleasure at his touch, the naughtiness of running his middle finger down between her thighs to touch her adorable clit for the very first time… they pushed him over the edge, and John cried out again as his seed spurted into Lauren’s mouth, to be swallowed expertly by the schoolgirl he had trained so very naughtily to suck men’s penises.
He went on rubbing gently up and down her very wet inner lips, then making little circles on her clit, as the spasms of his climax left him and the pleasure faded away. Lauren wriggled delightfully under this first sexual caress by a man, tiny kitten sounds emerging from her mouth, where John kept his cock as it softened, loving the dominance of the moment: her sweet, obedient suckling and her desperation for more of the pleasure a man could give her down between her legs.
He ceased the motions of his hand, and Lauren gave a questioning little sigh.
“No more for now, sweetheart,” he said. “It’s time to shower and get dressed in your pretty green dress and your pretty white lingerie. I’ll come back to take you up to the penthouse at seven.”
* * *
Mrs. Fredericks had done Lauren’s hair up, just as he had asked, into an elegant French braid, just loose enough to look like she had been out in the fields of Provence. She wore a little more makeup than she had yet donned for him, also according to John’s own specification. For a girl’s defloration, he thought, a more adult presentation always felt very much in order—so long as the lingerie under the elegant dress remained white.
“Good evening, Lauren,” he said, smiling down at her in Mrs. Fredericks’ living room.
“Good evening, sir,” she replied, looking down at his shoes and smiling shyly.
Jessica, who was sitting with Mrs. Fredericks keeping Lauren company as they waited for John’s arrival, interjected, “Mr. Killington, Mr. Graves says I may comfort Lauren tonight, in her bedroom, and Mrs. Fredericks says it is alright with her if you allow it. May I?”
John looked down at Lauren again. She had turned her eyes up to his. Her lips, slightly parted, had a hint of lipstick that turned them a seductive shade of red. He smiled, thinking about how they had looked around his cock, while he whipped her, and he felt a sudden impatience to kiss them, his left hand in the sweet French braid and his right at her waist.
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br /> “Would you like that, Lauren?”
“Yes, sir,” she whispered.
“I will make sure,” Mrs. Fredericks put in, “that it remains innocent. The door will stay open.”
Girls comforting one another after their deflorations had become a custom at the club. It formed a foundation for later, more advanced activities that featured the girls’ being instructed to pleasure one another while their owners and the owners’ guests watched. Usually the comforting involved only hugs and talking over the experience, but girls had occasionally discovered or developed their bisexual desires on such nights.
“Oh, Mrs. Fredericks,” Jessica said, turning red. “You do not need to worry about that!”
“Of course I must,” said the matron a little severely. “I know what girls can get up to, when they take one another’s panties down.”
John studied Lauren’s face, as she glanced over at Jessica. Her cheeks had gone pink. He and Hank would have to set up a double date, soon.
Mrs. Fredericks had seen it, too. “You girls will both be paddled if I find you being naughty with one another. Do you understand?”
“Yes, Mrs. Fredericks,” both girls chorused. Lauren looked up into John’s face again, the smile melting his heart and the crease in her brow making his cock give a little leap.
As soon as he had closed the apartment door behind them, and they stood in the empty hall, he took her in his arms and kissed her, gently teaching her with his tongue how to kiss like a grownup, until she yielded in his arms and clung to him in a foretaste of how her body would move under his when he entered her. He moved his hand from her waist to her bottom, and she gave a little cry as he cupped it through the green silk where the punished cheeks had no other covering thanks to the lacy thong in which he had dressed her.