by Robin Bond
Jennifer’s orgasm was almost upon her when Miss Bridget ordered Flora to withdraw. Jennifer could have cried with frustration; just when her discomfort, suffering even, was going to pay off, she was cheated out of relief. She stood there, her ass sore and throbbing, her cunt tingling.
“Now we come to the next stage of your training,” Miss Bridget said.
Jennifer groaned inwardly. There was more?
“Those clients who really enjoy working a girl’s ass often like to have their own asses attended to as well. What most of them enjoy is to have their asses licked. We call it rimming.”
Jennifer hadn’t particularly enjoyed tasting her own ass. She was doubtful she would enjoy tasting other women. But she resigned herself to being taught. It didn’t do to show resistance, or even hesitation, in front of Miss Bridget.
“You’re going to do Flora first, and then you’ll do me,” said Miss Bridget.
Flora bent over the desk. Jennifer knelt behind her, took hold of her ass-cheeks and opened them. She stared at the prim little hole, tightly clenched. When you looked at an asshole it always appeared far too small to insert anything. And yet, as she had just discovered, an ass will open far wider than you could ever imagine. Jennifer put her mouth to Flora’s ass and licked it, circling the little hole with her tongue. She went round and round and was pleased to hear Flora sighing with pleasure. She sucked at the hole, then licked it some more. She tried to push the tip of her tongue in, but it wouldn’t go, though she did manage to prise the hole open just a tiny bit. She continued licking. She wondered if girls ever got an orgasm just through ass-licking. She hadn’t met anyone who owned to this. But already in her brief time at St Swithin’s she had come to think that some girls would come at the drop of a hat. Certainly at the drop of a pair of knickers.
Miss Flora’s ass had a curious flat, earthy taste that wasn’t quite what Jennifer was expecting. It was neither pleasant nor unpleasant, just neutral, but what she did like were the noises she was eliciting from Miss Flora. It gratified Jennifer to know she could coax such pleasure from such an experienced girl. It would be even better if she could get the same results from Miss Bridget.
Jennifer ventured to put her hand to Miss Flora’s ass, squeezing it gently, then trail her fingers over the little opening, now shiny with lube and spit. Miss Flora shivered a little. Emboldened, Jennifer substituted her finger for her tongue, running it round Miss Flora’s asshole, which by now was slippery and a little dilated. Daringly Jennifer slipped her finger inside. Miss Flora grunted, but it certainly wasn’t a protest. Jennifer moved her finger around a little, experimenting, finger fucking just a bit. Miss Flora grunted again. Jennifer squeezed Flora’s ass with her other hand.
Miss Bridget had been watching intently. “Right, that will do,” she said sharply. She thought Flora had had enough pleasure. And she thought that it was time she tried a little of this herself. Jennifer looked like a girl with talent. Bridget hadn’t had a girl’s mouth on her ass for some time; she had been too busy.
She pushed Flora aside and bent over the desk herself. “Show me what you can do, Jennifer,” she said. Jennifer got to work, circling Miss Bridget’s asshole, round and round, trying to dig her tongue in. She heard Miss Bridget gasp at one point, as she tried more forcefully to get her tongue inside. Once she felt the hole was dilated a little and nice and slippery, she repeated her action from before, putting her hand there, stroking the ass then lightly fingering and finally pushing a finger inside. It felt to Jennifer’s inexperienced tongue that this ass was just a little bit looser than Miss Flora’s. Was it used more, had it more recently been penetrated, or was Miss Bridget simply wider? She began to finger fuck with a bit more intent. Miss Bridget groaned. For a moment Jennifer, still not sure of herself, thought this might be a sign of disapproval, but evidently it wasn’t. So, greatly daring, she tried pushing two fingers inside. Miss Bridget groaned again.
“Use your other hand to rub my clit,” said Miss Bridget, in a thick, throaty voice. Gingerly Jennifer slid her hand between Miss Bridget’s legs from the front and sought out her clit. To her surprise, it felt swollen already. Jennifer felt more confident manipulating a clit than fingering an asshole. After all, she had done plenty of work on her own clit, and since arriving at St Swithin’s she’d already felt a couple of other girls in that way, giving one of them a huge orgasm. Miss Bridget reacted like she had received an electric shock when Jennifer found the spot. She made several noises, all indicative of pleasure, as Jennifer worked her, cautiously at first, them more firmly. Jennifer was full of pride when at last Miss Bridget started to shake, her thighs came together and she groaned, not once but over and over again. Jennifer could feel Miss Bridget’s ass contracting around her fingers, but she kept them in. Finally Miss Bridget reached back and pulled them out. She stood up.
“Good,” she said. “You have a talent, no question. I think I’ll have to charge Mrs Prentice a bit extra.”
Arriving at Mrs Prentice’s house later the following week, Jennifer thought that she was well prepared. The session with Miss Bridget and Miss Flora had gone well, and both of them had complimented her. She felt well placed to cope with whatever the client wished for, even though Miss Bridget had told her that Mrs Prentice was demanding. Was she, Jennifer, not one of Miss Bridget’s girls? Was she not a member of an elite corps specially trained to meet the requirements of the powerful but promiscuous pussies she would encounter? Moreover, before she had set out Miss Flora had given her an enema. Jennifer had never tried this before. It felt strange, as well as being highly embarrassing, especially when Miss Flora made her sit on the toilet for a whole ten minutes with her bowels bursting before she was allowed to void them, and all in her presence. But now, as she pressed the bell, she was looking forward to giving a good account of herself and bringing credit to Miss Bridget.
Mrs Prentice opened the door. To Jennifer’s eye she had a rather stern look, but Jennifer resolved not to be intimidated. Her client was taller than the average, slim though with a well-developed bosom. She was smartly dressed in a shirt-waisted dress, a style Jennifer had not seen in a long time, but which suited the lady, being tightly fitting around the bosom but opening out below the waist. Jennifer was sure that Mrs Prentice was even wearing a petticoat underneath, because the skirt flared out. It was quite short, two or three inches above the knee, showing off Mrs Prentice’s elegant legs, which ended in a pair of heels. Mrs Prentice had her brown hair in a chignon. Her make-up was impeccable, and Jennifer could smell an expensive perfume. She was beginning to feel a little underdressed in her short little pleated skirt and blouse, with bare legs. At least she was glad she had worn her best underwear, a new set of black silk bra and knickers, both daringly brief.
Mrs Prentice led her through to what she called the drawing room, a room stylishly furnished, with expensive-looking wallpaper. She turned to Jennifer and asked if she would like a cocktail. Jennifer liked her well-modulated, low voice. She accepted graciously.
The two women sat side by side on the sofa. Jennifer was acutely conscious of Mrs Prentice’s gaze; she was being closely observed and inspected. They sipped their drinks in silence for a while.
“What did Miss Bridget tell you about me?” Mrs Prentice said.
“She said that you were demanding,” Jennifer replied. She was sure it was best to be open and honest.
Mrs Prentice smiled, though there was not much warmth in it. “What else?”
Jennifer thought back. “She said that you had a fondness for a good bottom, and that sometimes you were inclined to be rough.”
“So you know what to expect?” Mrs Prentice said.
“I believe so, Mrs Prentice,” Jennifer said.
“I wonder,” Mrs Prentice replied. “Well, let’s have a look at that bottom, anyway. Stand up and take off your skirt.”
Jennifer stood in bra and blouse and knickers. Mrs Prentice made a gesture and she turned around, giving her the back view. Jennifer turned
round again.
“Take the blouse off, my dear,” said Mrs Prentice. Once more she gestured for Jennifer to give her the rear view. When Jennifer had turned back Mrs Prentice stared at her groin. “Take the knickers off,” she said.
Jennifer did as she was told, tossing the knickers to one side, the way she had seen strippers do it. Mrs Prentice gave another gesture. Jennifer turned slowly, feeling Mrs Prentice’s eyes boring into her ass. When she came round again to face Mrs Prentice, she said, “Come and lie across my lap, face down.”
So this is where it starts, Jennifer thought, as she spread herself across Mrs Prentice’s lap. It was a humiliating position, one that she had not had to adopt since a child. But the first few smacks were not too hard. At least, nothing like she had been expecting. A few days after the session with Miss Flora and Miss Bridget, when she had been relieved of her anal virginity, Miss Flora had given her a spanking, not over the knee but bent over the desk. She had used a wooden paddle, and it hurt very much indeed. What is more, it left some severe marks, which had taken a week to fade. What Mrs Prentice was doing in no way resembled that
However, not much to Jennifer’s surprise, there was worse to come. The spankings from Mrs Prentice’s hand grew steadily harder, until they stung really quite badly. Soon Jennifer’s bottom felt as if it was on fire.
Mrs Prentice stopped spanking and slowly stroked Jennifer’s cheeks. “Is there anything prettier than a cute little bottom turning slowly pink?” she said. Jennifer thought no answer was required. “Perhaps the only thing is a cute little bottom turning a darker shade of pink, and then bright red, and if it gets spanked some more, turning a delicate shade of purple.”
She resumed spanking, her hand falling on alternate cheeks of Jennifer’s backside. She shifted her position slightly, trying to mitigate the effects of the blows, but it didn’t do any good. After another five minutes of steady spanking, Mrs Prentice stopped again. “Perhaps something a little more forceful,” she said.
Jennifer thought the present degree of force was more than adequate, but she didn’t dare say so. She waited to find out what came next. She didn’t see Mrs Prentice pick up the hairbrush lying next to her. But she felt it, as the brush descended on her left buttock. Jennifer squealed. It was painful, especially on a bottom already tenderised. Mrs Prentice took no notice of the squeal, instead bringing the brush down hard on Jennifer’s right buttock. Jennifer gasped and wriggled again, but she didn’t dare try to get away. She wanted to go back to college sure of a good report, she wanted Miss Bridget to be proud of her. It wouldn’t do to try and escape.
Jennifer, whose experience of spanking was limited to the session with Miss Flora, had no idea how much a little wooden brush could hurt. Mrs Prentice was relentless, the brush rising and falling in a steady rhythm. It made a slapping sound as it struck, and the pain came a split second later. Mrs Prentice was indifferent to the noises that Jennifer made. As far as Jennifer could see, the spanking could go on for ever, though long before that Jennifer’s bottom would be bruised and battered. Just as Jennifer was wondering how far it could go, and whether she could take much more, Mrs Prentice set down the hairbrush.
“Such a pretty colour now,” she said. “I’m going to take a picture and send it to my friend. Maybe she will want to book you too.”
Mrs Prentice told Jennifer to stand up. She picked up her phone from a nearby table and began snapping Jennifer’s ass. Then she told Jennifer to follow her upstairs. “We’ve finished the warm-up,” she said. “Now we get serious.”
Jennifer didn’t like the sound of this. The spanking she’d had was just a warm-up? It felt pretty serious to her. Jennifer’s bottom was still tingling and she was sure it was bright red, if not worse. Mrs Prentice took her into the main bedroom. It was tastefully decorated but comfortable. She turned to face Jennifer.
“I suppose because I am Mrs you are wondering where my husband is,” she said.
“Well, no not really,” Jennifer answered. “It’s none of my business.”
“Hmm,” said Mrs Prentice. “I think in a way it is. Doesn’t it help to know one’s clients, to find out what sort of people they are, and in particular how they conduct their sex lives?”
“If you put it like that, you may be right,” said Jennifer. Now that the subject had been brought up, she did admit to a certain curiosity.
“It’s a female-led relationship,” said Mrs Prentice. “Do you understand what that is?”
“I suppose it means you are the boss.”
“Exactly,” said Mrs Prentice. “It means I do exactly as I please in the marriage. My husband is there for my convenience. Or absent, as the case may be. And one of the things that pleases me is to have sex with other women. Often with young women, such as yourself. And often with girls who will let me do as I like with them. I like my husband to know this; in fact I enjoy rubbing his nose in the fact that I have no need of his cock and prefer to fuck women.”
“I see, Mrs Prentice,” said Jennifer.
“Sometimes one is lucky enough to find a girl who will play my games just for the fun of it. But because I have such particular tastes, I often find myself paying so that I can get exactly what I want. I don’t know if you know how much Miss Bridget charges for your services?”
“Not really,” said Jennifer. “She keeps the financial side of things pretty much to herself.”
“Well,” said Mrs Prentice, “you don’t come cheap. That is why I like to get full value for my money. I’m going to make you jump through several hoops this afternoon and at the end of it you will be sore, I can promise that.”
Something twitched in Jennifer’s belly, or perhaps lower down. She was a little scared; but at the same time she felt aroused by what was to come. After all, she was a true submissive, so Miss Bridget had told her. And so she hoped to enjoy her ordeal, however severe.
Mrs Prentice went to a drawer in a table and took out a butt plug. It was pink silicone. And it looked enormous. Jennifer stared at it.
“I can see you think this is too big,” said Mrs Prentice. “What people generally don’t understand is that the anus is extremely elastic. Almost as much as the pussy, which after all can expand to take a baby’s head. So I am going to work this up inside you, whatever the tightness of the fit. Tell me, have you had any dilation training?”
Jennifer thought back to the sessions with Bridget and Flora. Did that count? “Well, sort of,” she said.
“No matter,” said Mrs Prentice. “The tighter the better.”
She told Jennifer to lie face down on the bed. Mrs Prentice sat beside her and prised apart Jennifer’s buttocks, peering intently at the hole. “Clench the muscle,” she said.
Feeling a little embarrassed at the knowledge that Mrs Prentice was staring intently at her anus, Jennifer did as she was told.
“Hmm,” said Mrs Prentice. She put her finger to the hole and pressed gently. Involuntarily Jennifer tightened her ass again. Mrs Prentice pressed a little harder. “Push down,” she said.
Jennifer did the best she could. Mrs Prentice pressed against her anus again. This time the finger went in, nearly up to the knuckle. It felt different from having Miss Flora fuck her with a strap-on. The finger was alive, it moved. It was more intrusive, even if it only went in part-way. Mrs Prentice took her finger away. She fetched some lube and applied it both to her finger and to Jennifer’s ass. Then the fingering resumed, but this time much harder. Mrs Prentice rammed first one finger, then two into Jennifer’s ass over and over again.
At last the fingers were withdrawn. Now it was time for the plug. Mrs Prentice lubed it, then put the tip to Jennifer’s asshole. After the fingering, it started to go in easily enough. But the plug was bigger towards the base, and soon Jennifer felt herself being stretched as never before. She groaned, but Mrs Prentice took no notice, continuing to press the plug home. Jennifer felt sure she must split if it went much further. But she was to learn that Mrs Prentice, a true expert in anal matters, wa
s right. Her anus was far more flexible than she thought. True the plug did hurt as it went in the last two inches, but finally it was in place, all the way up to the flat base.
“Good girl,” said Mrs Prentice. “Now get up and walk around. I want to see it.”
Feeling awkward and shy, Jennifer walked around the room under Mrs Prentice’s critical gaze. It seems that she passed the test, whatever the test was exactly, because Mrs Prentice called her back.
“Now, my dear,” she said, “It’s my turn for some attention.” She lay on the bed, face down. “Eat my ass,” she said.
Jennifer hadn’t been expecting such a direct change of gear. But at least she had had proper training from Miss Bridget on what was required. She lifted Mrs Prentice’s skirts right up to her waist, then her petticoat. Underneath Mrs Prentice wore a pair of ivory coloured French knickers, or tap pants. To Jennifer’s inexperienced eye, they look expensive. Jennifer pulled them right down and took them off. Then she pulled Mrs Prentice’s legs apart and spread her buttocks, massaging them, moving them this way and that before pulling them wide apart to reveal the tight little orifice. Jenifer bent her head. Mrs Prentice had perfumed her ass with something costly and delicate; Jennifer inhaled the fragrance. Then she bent her head further and planted a kiss right on Mrs Prentice’s asshole. Mrs Prentice sighed. Jennifer began to circle her anus with her tongue, all the while kissing and sucking. She ran her tongue round and round, trying to coax Mrs Prentice’s ass open. She wondered if Mrs Prentice was going to want fucking, and if so whether it would be anal. Jennifer was prepared for that. Although her experience was non-existent of that precise manoeuvre, she been pegged herself; she knew the routine.