Chapter 1: The Orphanage

It was the middle of summer in Victorian London. Helen lay in her bed in the dormitory in the Charing Cross orphanage. She was so happy that she had been selected to leave the old Tower orphanage and brought here. Obviously Charing Cross orphanage was much richer than the previous one and occasionally she wondered where the money came from. Although Victorians were very charitable there was so much poverty that usually money was spread very thin.

The only problem with this orphanage was that unlike the previous one it was girls only. She missed the boys. She had been getting very interested in exploring their bodies and having them explore hers when her life was uprooted and she was brought to this new place. In fact, since the orphanage was isolated from the outside world she had not even spoken to a male in the few years that had passed since then. Or, in fact, seen one except in the distance through a barred window.

At eighteen years old she would soon graduate. She wished she had been born a boy so there was at least a chance that she might be able to leave the orphanage and go on to university. As a girl in that era, it was almost impossible. The best she could hope for was that she would soon leave to be a maidservant in a rich household.

Around her in the dormitory were about a dozen other senior girls in their beds. The gaslights had just been turned out. She could tell from their breathing and from the almost imperceptible movements, that some of them were masturbating, just like they did most nights. She had made sure herself, as she got into bed, that her nightdress slid up around her waist so that she was uncovered from the waist down under the bed covers.

She started to stroke her breasts through the thin material of her nightshirt, feeling her nipples harden as she started to fantasize about her limited experience of sex.

She remembered the feeling of excitement as a boy’s hand slid up her leg under her long skirt. It felt so naughty not stopping him, feeling his excitement grow as he got closer to her underwear. She knew that if they were caught they might get caned, but that seemed to make it even more exciting. They would have to be quick, make every minute count. She remembered how his fingers slid across the smooth skin of her inner thighs. She reached down and heard him gasp in surprise and pleasure when she put her hand on the bulge on the front of his breeches. Emboldened by her forwardness the boy slipped his hand into her cotton knickers. She remembered how wet she was, enjoying the feel of his fingers as they slid into her crease, and then into the opening of her virgin sex.

Her hands crept lower across her nightdress as she moved one leg to open up her sex. She twirled her fingers in her pubic hair, sending gentle waves of pleasure through her groin, a teaser for the more intense excitement to come.

She unbuttoned the boy’s breeches and took out his cock. She loved the feel of its hardness, how excited he was by her body. She started to stroke him, feeling him rocking his hips into her fist. She took the boys hand and guided it to her clit, loving the wonderful feelings created when he started to finger her.

She started to stroke her lips with her fingers. She slipped a finger between her inner lips, surprised to find how wet she was already. She reached down with her other hand and opened up her outer lips so she could explore her whole sex unencumbered. Finally her finger touched that special place. A shudder of pleasure ran through her body.

She remembered the intense orgasms she would have when a boy stroked her clit as she stroked his cock. She would cum quickly, too afraid of being caught to take the time to savor the experience. Soon her stroking would have its effect and the boy would climax too. She liked the sight of the white cum pulsing out of the end of his cock as her fist slid up and down its length.

As she lay in the dormitory, Helen was close to coming. She thought of one of the few times that she had dared to put a boy’s cock in her mouth and started to lick him. The boy was so intensely excited that he came almost immediately, emptying his thick cum onto her tongue. She wondered whether boys ever licked girls’ clits, thinking how wicked that would be, but how good it would probably feel. She could feel her body trembling as she came close to orgasm. And she thought about the ultimate: putting a cock in her cunt. Somehow she knew that would feel good. She slid a finger inside herself, imagining it was a cock. As she fantasized about what being fucked would feel like, her fingers stroked her clit harder and faster and her orgasm broke over her like a tidal wave.

She woke early the next morning when something hard hit her. It was the communal dormitory hairbrush, and it was her turn to use it. Not to brush her hair though. The brush had a long round handle made of carved bone or antler. It hadn’t taken the dormitory long to discover that it felt good to use to masturbate with. Tradition had it though, that when you masturbated with the hairbrush you had to lie on top of the blankets on your bed and to tell the rest of the dormitory what you were fantasizing about while they watched you. Far from regarding the exhibitionism a price to pay for the pleasure of the hairbrush, Helen really enjoyed the feeling of the power of her sexuality over the rest of the dormitory. Of course the other girls would watch and listen and masturbate themselves. Most of the other girls seemed to have had similar experiences to Helen, some early sexual experimentation with boys wherever they had been before, and then no access to the male sex since they had been in the all girls’ school. None of them had lost their virginity before coming to the school although several had been getting close to daring to do so before they were transferred between orphanages.

Helen slid out from under the blankets on her bed and lay on top of them. She pushed her nightshirt all the way up to her shoulders so that her breasts were also bare. She parted her legs wide, aware of the other girls’ eyes on her sex. She slid the head of the hairbrush handle up and down the length of her sex, gently parting the lips. She could feel herself start to get turned on, knew she would be wet. She slipped the handle into the opening to her cunt, enjoying the tautness of her body before it gradually relaxed to admit the bone cock.

She started to tell her fantasy, talk about the time that she had been caught with a boy soon before she came to this school. She had been in the boy’s toilets, even, which was obviously against all the rules. When he started to put his hand up her skirt, she stopped him. He was disappointed at first until he realized that she had stopped him so she could take off her dress completely. Then she slipped off her knickers. She stood naked before him. He bent down and kissed her nipples, sending tremors of pleasure across her chest. She asked him to bite them gently, savoring the pleasure-pain when he did. She undid the boy’s breeches and made him step out of them, took off his shirt. The two of them were completely naked. His fingers crept down across her stomach and into the crack of her sex. Her clit was already hard in anticipation, she knew she would come instantly if she wanted. She let herself enjoy a small orgasm. Then she crouched down and took the boy’s hard cock into her mouth. She reached between her legs and stroked herself with one hand as she held his cock with the other. She had loved the feel of his cock sliding in and out of her mouth as the boy’s hips rocked back.

Helen started to stroke her clit as she fucked herself with the hairbrush handle. She could see the other girls were spellbound by her story, watching the ivory colored handle slide in and out of her engorged cunt as they masturbated. Soon Helen was coming, moaning quietly as each thrust of the handle went deep into her cunt. Helen rolled over onto her front, holding the hairbrush in both hands, keeping it inside herself.

She continued her story. The boy had been close to coming. She had let go of his cock to stroke his balls while he fucked her mouth. Suddenly the door to the toilet had been flung open and the headmaster was standing there. It was bad enough being in the boy’s toilet but completely naked as well. With a cock in her mouth. It was humiliating, but somehow exciting at the same time. They were both made to get dressed and then marched off through the school to the headmaster’s office.

The boy was made to take down his breeches and bend over a chair. Helen watched as he was given a dozen strokes of the cane on his bare bottom, seeing the red marks appear criss-crossed over his white cheeks. She wanted to reach over and stroke his cheeks, slip her hand between his legs, feel the balls that she could just see hanging there temptingly. The boy pulled up his breeches. Next she was ordered to take off her knickers. She reached under her skirt and pulled them down and stepped out of them. Then it was her turn to be bent over the chair. Her skirt was flipped up over her back so that her bottom too was bare. Somehow, bent over like that knowing that both the headmaster and the boy had a perfect view of her pussy, turned out to be very arousing. The twelve strokes were delivered very slowly, and although they hurt dreadfully it aroused her even more. Each stroke she moved her legs a bit further apart, presenting her teenage pussy to her audience more blatantly, arousing herself still more. She knew she could have come on the last stroke if she had dared. She never knew if she had been expelled from the orphanage as a result of the incident, but it was not long after that she had come to this school.

As Helen related the end of her story, her hips rose up and down on the hairbrush. In this position, the bone handle slid in and out of her cunt and the bristles on the hairbrush rubbed on her clit. It was too intense to take unless she was already extremely aroused, but when she was it made her come almost at once. As she savored her delicious orgasm she was aware that many of the girls around the dormitory were coming too, sighing and moaning, unable to keep completely quiet.

Chapter 2: Departure

Helen was sitting in a science class one day when she was summoned to the headmistress’s office. She wasn’t sure why and she wondered if this would be the time she left the school. Nobody ever seemed to leave in a very planned manner, they would just leave a lesson and then never be seen again. Their belongings would be packed up by a maid and their place taken by those of a new younger girl arriving at the school.

She knocked and went into the headmistress’s office. There was a man there, the first one she had been close to for a few years.

“This is Mr Christie,” the headmistress said. “And this, of course, is Helen. I think that you will find her an excellent choice.”

“Tell me again how she was selected,” said the man.

“She was in the Tower orphanage for the early part of her life. As you know they are always on the lookout for sexually precocious girls for us. She paired up with several boys and would make them cum and let them finger her until she came too. She would sometimes suck their cocks, although she never apparently experienced them licking her. Of course she is still a virgin. But the headmaster was worried she would not be for long so the he decided to catch her one day. He followed her to the boy’s bathroom where she met a boy. He let them get started before opening the door. Can you believe she was completely naked? Then when he caned her, she spread her legs wide to show off her pussy to him. He said he was very tempted to fuck her, but instead he beat her harder. He was sure that she almost orgasmed on the final stroke of the cane. Anyway, I think you can say she is adequately adventurous and self-confident sexually.”

“And since she has been here?”

“The dormitory informant tells me that she masturbates every night and most mornings. She comes quickly and sometimes multiple times. When it is her turn with the hairbrush she loves to show off. I think she enjoys fucking the hairbrush with others watching, a definite exhibitionist streak. I watched her myself this morning through the peephole in the ceiling and she came several times while she relived her early experiences with boys.”

“Is she up to a full-size hairbrush?”

“Oh yes, that dormitory has a big one. Eight inches. And thick. She has definitely got herself ready for a real cock.”

“What about her ass?”

“She hasn’t discovered the pleasures of her ass yet.”

“And other girls?”

“She doesn’t seem to have too much interest in other girls. She seems to prefer to remember what she did with boys rather than do anything new with girls.”

“That’s a shame. We’d better make sure to check her in a little bit.”

“She’s very well finished,” the headmistress said. “One of the best we’ve had recently. Smart and very sexual.”

“We’d better have a look at her then,” said the man.

They both turned to her as if noticing her for the first time. Helen had only understood about half of what they were talking about but she was astounded at how much the headmistress knew about the secret sexual goings-on in the dormitories.

“Take off your dress,” said the headmistress.

“I beg your pardon?” said Helen.

“I said take off your dress.”

“I can’t. Not in front of a man,” said Helen angrily.

“I think perhaps she is too strong-willed,” said the man. “Let’s do this another way.”

The man moved over to Helen and grabbed her wrists. He pulled them up above her head and at the same time pushed her back against the wall. She felt metal cuffs close around her wrists so that she was pinioned against the wall with her hands pinioned above her head.

The headmistress passed him a large pair of scissors. He cut up the front of her dress and across the shoulders and pulled off the useless piece of material. Helen stood there in just her knickers. She wanted to reach down to cover her breasts, but they had a mind of their own and she felt her nipples harden with excitement. The man felt her breasts and nipples as if he was judging her.

“Big nipples,” he said. “Good. And an attractive deep pink color too.”

He reached forward and tweaked one of her nipples. It hardened even more.

“Quite sensitive,” he said. “Perfect.”

Next, he pulled her knickers down and roughly pulled them out from under her feet. Helen was completely naked.

“She has a nice looking pussy,” said the man looking at the cloven mound below Helen’s pubic hair. He reached out and felt the softness of her outer lips, pulling them apart a little to look into her most private place. Helen kept her legs clamped together.

“Do you want to accept our guarantee that she is orgasmic?” said the headmistress.

“No, I’d better make sure,” replied the man.

The headmistress passed the man a wooden rod about two feet long. It had a leather strap attached at each end. The man buckled one of the straps around Helen’s left knee. Then he roughly pushed her off-balance so that for a moment she hung by the wrist-cuffs. By the time she was back on her feet somehow the man had got the other strap buckled around her right knee so that her legs were forced apart. She felt very vulnerable but also very turned-on. Her pussy was completely defenseless.

The man reached into his bag and took out a small pot of ointment. He dipped a finger in the ointment and pushed the finger between Helen’s outer lips rubbing the ointment between her inner labia and over her clit. Her pussy started to tingle intensely.

“She is pretty wet already,” said the man. “I think I’ll try out my new hysteria reliever.”

He reached into the bag again and brought out a mechanical contraption. It seemed to consist of a small box of machinery attached to a flexible cable with a small lump on the end about the size and shape of a walnut. The man pressed a lever on the box and it started to buzz. He pressed the walnut into her crack. It was vibrating intensely. Immediately waves of pleasure flooded through Helen’s body. The man reached down and opened up Helen’s sex wide so that her clit stood proud. He pressed the walnut right on her clit. Helen didn’t want to cum but she knew that there was nothing she could do to stop it. In no time she felt her orgasm explode through her body. She was shaking and moaning uncontrollably despite her best efforts to be dignified.

Helen felt the cuffs released from around her wrists. She let herself slide down the wall, her body almost collapsing from the intensity of her climax. She no longer cared about the undignified way that the wooden bar spread her legs obscenely, her pussy on view to everyone.

“It’s your last chance with her,” Mr Christie said to the headmistress.

The headmistress pulled her skirts up around her waist and tucked them in, and then slipped off her own knickers. She moved so she was standing in front of Helen, still almost in a stupor from her orgasm and sitting on the floor. The headmistress spread her legs, grabbed Helen’s hair and pulled her forward.

“Lick,” she said. It was clearly an order and not a suggestion.

Helen had seen lots of pussies in the dormitory, of course, but never one so close. She pushed her tongue forward and got her first taste of another woman’s cunt. She wasn’t entirely sure what to do but she knew how she liked to touch herself and she let that be her guide.

Mr Christie looked over at the headmistress with her pupil buried between her thighs.

“You love it when it is their first time, don’t you?” he said.

“Mmm,” she sighed. “They are a bit clueless but keen to please. Oh yes, Helen, just there. Focus on my clit.”

Helen could feel the tiny hard button of her headmistress’s clit under the tip of her tongue. She circled around it, nudging it from all direction, caressing it with her tongue the same way she liked to caress her own clit with her finger every night before she went to sleep. She could tell from the way the headmistress was breathing heavily that she was doing something right.

“Put your finger in me,” he headmistress moaned, clearly very aroused.

Helen slid her hand up between her thighs. She slid her finger back and forth between the older woman’s labia until she found the entrance. She pressed her finger upwards and it slipped into the warm, wet depths of her headmistress’s pussy.

“Oh yes,” she moaned, “now fuck me hard.”

Helen started to move her finger back and forth just like she would do with the hairbrush in the dormitory. At the same time she started to lick the headmistress’s clit harder and more aggressively. The headmistress was moaning encouragement continuously.

“Oh gosh you are a natural,” she moaned. Suddenly her body shuddered and she let out a long groan. Helen felt the headmistress’s cunt flood with excitement as she climaxed, grinding her pussy onto the schoolgirl’s mouth. The headmistress stepped back and let her skirts fall back around her ankles, back to being a demure Victorian woman.

“Well, I reckon she passed that test,” Mr Christie said. “Let’s give her a quality mark.”

Mr Christie pulled Helen away from the wall and rolled her onto her front. With the bar still between her knees she couldn’t really lay flat and had to take a very exposed-feeling position with her ass in the air. He took a blindfold and put it on her so she could see nothing. Helen felt scared, having no idea of what might happen next, and feeling very vulnerable with her pussy complexly exposed.

She felt the man’s fingers slide between her lips from behind, gently stroking her clit. It felt good after the intensity of the machine. After about a minute of gentle stroking he pushed the vibrating walnut between her legs and back to her clit. Again the pleasure exploded out from her cunt. The noise of the machine suddenly got louder. The vibrations got even faster and more intense. It seemed to make Helen cum almost instantaneously. She felt the strong contractions of her orgasms begin to pulse through her body. In mid-orgasm she suddenly felt something on her left buttock followed by a sharp jolt of pain that decayed into a dull throb as her orgasm itself decayed. She noticed a scorched smell.

“OK, she’s branded,” the headmistress said as the machine was turned off.

The blindfold was removed. Helen saw the headmistress standing there with a small branding iron in her hand. She put it back into the fire in the grate.

“How do you think she’ll do?” said the headmistress.

“Very well. She’s smart. She’s pretty. Big nipples, big labia. They always do well at auction, easy to see from the back of the room. She’ll need shaving, of course, to show off her slit at its best. Could be a very high price.”

“Good. That will help the school’s finances.”

“I’ll send someone to collect her later this afternoon.”

Chapter 3: Preparation

Helen left the school for the last time that day. A coach pulled by a horse drew up in the courtyard of the school, Helen climbed into it. The coachman cracked his whip and for the first time in a few years Helen was outside the walls of the orphanage and school where she had been living.

Helen looked at amazement at the city of London, having only seen it in pictures for most of her life. She wondered whether she should just leap from the carriage and see if she could make her way in the world, before she realized that the carriage doors did not have any handles on the inside.

Eventually they arrived in the courtyard of another building and she was taken inside into a room with a bed, chair and wardrobe. She was left alone. As the door shut she heard the key turn in the lock. There was a large jug of hot water there and so Helen took off her orphanage dress and washed herself. Looking over her shoulder at the mirror in the bathroom she could see a cross on her left buttock. Right now it was an angry red but she knew it would heal into a life-long brown cross.

The wardrobe contained several dresses, all her size, so she put one of them on. She felt happy, not knowing what the future would bring but trusting that it would be the start of the next stage of her life. The start of her adult life.

Later she was brought a tray with a delicious meal the likes of which she had never seen in the orphanages where she had spent her life. They had prepared a huge plate of fish along with fried potatoes, small sweet peas and pearl onions. And a jug marked “claret.” She knew from her geography lessons that this was red wine from Bordeaux but she had never tasted it before. She liked it immediately.

A maid came and took her tray away and bade her goodnight. She changed into her nightdress and got into bed. “What an extraordinary day,” she thought as she relived her experience in the headmistress’s office while her finger slipped familiarly onto her hard clit.

The next morning she was still in bed when she heard the key turn in the lock to her room and a young man came in with some breakfast and another large jug of hot water.

“Hi,” he said, “I’ve got to prepare you this morning.”

“Prepare me for what?”

“Hasn’t anyone told you anything yet?”

“No, I was taken from the school and brought here. I’ve no idea what is going on.”

“OK, let me explain. Your virginity will be auctioned this afternoon. It is very fashionable in the upper segments of society to purchase a teenager and have a deflowering party. Especially rich merchants, aristocrats. And the bohemians such as actors and artists, although only the stars are rich enough to afford it. Prepared virgins like you are not cheap.”

“What do you mean prepared?”

“Well, you were selected at an early age for being sexually advanced. I bet you were at another orphanage before and they caught you with your hands on the boys’ cocks. Since then you have been cloistered away from boys and men for a few years as you ripened. As you are here I expect you still showed the signs of being highly sexed: masturbation several times a day, perhaps licking some of the other girls’ pussies, maybe masturbating in public. Girls from your school in particular are very much in demand.”

“Why?”

“Because you have been properly educated and are not just a pretty body.”

“But what does that matter at a—what did you call it—deflowering party?”

“There, not at all. But after that you will be auctioned again to someone who will take you permanently. You can run a household or be a governess to his children as well as someone highly trained for sexual pleasure. You don’t think that Jane Eyre was simply a governess to Mr Rochester’s children did you? Of course she was fucking him as well.”

“But I’m hardly highly-trained for sexual pleasure. I’m still a virgin for a start.”

“If all goes well, after the deflowering party you will be taken to a training school and taught all the sexual arts. By the time you are auctioned for the second time you should be skilled and knowledgeable about all aspects of sex.”

“So what will happen at the auction?”

“You will be brought out on stage in some nice clothes. I have to help select them this morning. You will have to take your clothes off and stand naked before them. My advice is to be as sexy as you can. Give them a good view of your pussy. Masturbate for them. They will only bid on you if they are turned-on by you, so the more men that you can get aroused the better. You want to sell for as high a price as you can.”

“Why? Do I get the money?”

“No, it all goes to the school. But you want a high price because it will affect where you end up eventually. If you sell for a high price this time around, then whoever buys you will have to send you to the best sexual training school so that they can recover a good price for you in the second auction. And if you go for a high price in the second auction then only someone rich will be able to afford to buy you. So they will have lots of other servants and you won’t end up having to do a lot of menial work. They might even give you a decent allowance. Also, they are much more likely to be sexual connoisseurs themselves. Whereas if you go for a low price they might not bother training you at all and someone will just buy you as cheap labor around the house. So let’s get you prepared. Get out of bed and take off your night shirt.”

Helen pulled back the blankets and stood up. She already mentally decided that she would put all her effort into getting a premium price. She unashamedly slipped her nightshirt over her head and stood naked before him.

“First I am going to shave your pussy-lips. You get a better price if the bidders can clearly see the merchandise. Lie down on the edge of the bed and spread your legs.”

The man took a shaving brush and lathered her pussy with soap and hot water. The brush tickled in an alluring way. Next, he took a cut-throat razor and opened it. Helen felt very vulnerable as she felt the sharp blade sliding over her outer pussy-lips, but his fingers felt confident and gentle. Soon her lips were bald.

“Feel that,” said the man.

Helen reached down and stroked her outer lips. They felt softer and smoother than she was used to. In some ways they felt like they did when she was a little girl before her hair grew, although back then they were not split by the protruding pink tongue of her inner labia.

The man went over to the wardrobe and produced something.

“What’s that?” Helen asked.

“They are knickers of a very special type. They are called thongs. Put them on so that this piece runs up the crack of your bottom. When you are seen from behind the cheeks of your ass are clearly visible. And when you are seen from the front, the thong stretches tightly over your sex so you have a prominent bulge.”

Helen pulled the scarlet knickers on. She felt very naughty with her cheeks bare and her shaven pussy barely contained under the tight red material. The man returned to the wardrobe and came back with a dress.

“Put this on next. It is a special type of dress. It looks unexceptional. But there is a thin lace of leather here that attaches the skirt to the bodice and also holds the bodice tightly across your chest enhancing the shape of your breasts. If you pull this loop here then the material comes undone. The bodice opens up the front and detaches from the skirt, so you are naked from the waist up. Try it.”

Helen put the dress on. She put her thumb through the small loop of leather and pulled. Just as promised, the bodice detached from the skirt and as she continued to pull, the strip of leather undid up the front of the bodice and her breasts sprung free.

“Now if you pull this loop on the other side the skirt will come undone in a similar way.”

Helen pulled the other loop. The skirt split along a hidden seam up the front until it was just joined at her waist. A final tug and the waist split in two and the skirt fell away from her.

The man took the skirt and the bodice and with a button hook quickly rethreaded the strips of leather and re-assembled the dress. Next, he produced a comb and a pair of scissors and trimmed Helen’s hair as she sat there in just her thong. Finally, she put the reassembled dress back on.

“OK. You are ready to go. When you first come out onto the auction stage, you should just go and sit in the chair there while the auctioneer describes you. He will ask you to get up once the bidding starts. Here’s how to use the dress to work up the excitement of the crowd. Don’t be in too much of a hurry to get naked, let the price build up. Then take off the bodice to reveal your breasts and let the price start rising again. When it starts to stagnate, take off the skirt and parade around in just the thong. Make sure to show both your front and back. I think you’ll be amazed at the prices being bid. Next, slip off the thong. It is best to do that facing away from the audience so that as you bend down to pull the thong off your feet your pussy is clearly visible between your legs. Go back to the chair you were first sitting on. Put one foot on the chair so that your pussy is opened up to the audience. Then when the bidding seems to be running out of steam start to masturbate. If you manage to be so turned on that you cum, all the better. Shall we have a rehearsal?”

Helen sat on the bed, then stood up and gradually disrobed as she had been instructed. The man watched her closely. As she gradually became naked and started to masturbate the man unbuttoned his breeches and got out his cock. It was already hard. He started to stroke it.

“I’m ready to place a bid,” he said.

“I’m very grateful for all your advice,” Helen replied. She knelt in front of the man and took his cock into her mouth as a thank you. It was the first adult cock she had seen, larger and hairier than those of the boys she had played with when she was at Tower orphanage. She reached underneath him to stroke the sack holding his balls. All the time she continued to stroke herself. The man held her head and pushed his cock into the back of her mouth. Helen almost gagged on it but she continued to swirl her tongue around his cock. She let herself climax just before he did, tasting the distantly-remembered flavor of cum on her tongue while the pleasure of her orgasm rippled through her.

“I think you’ll get a good price,” said the man as he stood up and buttoned up his pants. “I’ll come back for you after lunch to take you to the auction. Good luck.”

The man let himself out and she heard the key turn again in the lock.

Chapter 4: The First Auction

Helen walked out onto the stage at the front of a large room and sat down on the chair. There was a large number of men there looking expectant. The man she had met in the headmistress’s office the previous day stood at a podium. Suddenly she remembered something that she had read about in her studies about a Mr Christie the famous auctioneer. He started to speak.

“Gentlemen. Christie’s presents the last lot of the day. It is not often that a girl of this quality comes to auction. This is Helen. As you know from your catalogue she has been well educated at the famous Charing Cross orphanage and carries the Charing Cross brand of authenticity on her left buttock. Of course the bulk of the proceeds from today’s auction go to the Charing Cross orphanage to fund their work so please be generous in your bidding.

“Helen is a smart girl, especially in mathematics. But she is also highly sexed, masturbates to orgasm most days and enjoys exhibitionism. Christie’s verified her orgasmic capability only yesterday. Her pussy is cock-ready so that I am confident that she will feel no pain and be an enthusiastic partner in her first experience of penetration. She has been isolated from boys and men since her induction into Charing Cross orphanage so the combination of strong sexual drive and lack of outlet means that she is ravenous for her first taste of true sex. She has been prepared to the highest standard.

“I should remind you of the bidding rules. In order to bid you must have an erect cock. As the price rises you indicate that you are still in the bidding by continuing to stroke your cock. If you don’t have a hard cock you may not bid, whether it is from too much drink, too little interest or coming prematurely due to over-excitement. Please come to the front of the room if you are bidding so that I can see you stroking your cocks. Of course you will also get a better view of the lot being auctioned.

“The successful bidder will get to take Helen’s virginity this evening, and has a branding right. She should then be trained at the successful bidder’s expense and is scheduled to be re-auctioned to a permanent owner two weeks from today.

“Also, I trust you have heard of the Charing Cross tradition. Although not a legally enforceable right, the permanent owner has always granted the winner of the first auction a night once a year indefinitely, and this tradition is expected to continue.

“I would like to remind you that her asshole is not yet cock-ready and is not to be used. That is the privilege of her final owner.

“So I am going to open the bidding at ten guineas.”

Helen was surprised at the price. She knew that that was the annual income of a tradesman. She stood up as she had been taught earlier in the day, imperceptibly pushing out her chest to emphasize her breasts.

Mr Christie started to work his audience. “Imagine your friends watching you undress this young virgin in your drawing room this evening. Show them the cross branded on her bottom, the mark of the highest quality in London, standing not just for intense sexuality but for intelligence too. Imagine as you lay her down on the hearth-rug, her legs spreading for you to reveal her pussy to a man for the very first time. Imagine all your friends envious as they watch you slide your hard cock into her tight virgin entrance.”

Several men came to the front of the stage stroking their erect cocks.

“Twenty guineas,” said Mr Christie.

“Thirty guineas,” he said half a minute later as the crowd of masturbating men grew.

Helen pulled the leather lace that undid her bodice. The audience gasped as her breasts sprang free. She reached up and pinched her nipples. Now there were more men at the front of the stage.

“Look at those breasts, look how firm they are, just ripe for your caresses,” said Mr Christie. “Imagine your mouth closing over those nipples. Look how hard they are.”

Helen bent over so that her breasts were close to the masturbating men, giving them a close-up view of her nipples, crimson with excitement.

As the bidding went over one hundred guineas, she could see some of the men starting to drop out at the high price, and others clearly doubtful. She pulled the other leather lace and her skirt fell away. Another gasp at the sight of her red thong, instead of the expected Victorian bloomers. She turned round showing off her ass. The crowd of men stroking themselves in front of the stage grew again.

Mr Christie worked the crowd. “Look at that ass, and that incredibly exotic underwear. You can now see the cross branded on her buttock, a sign of quality of extremely limited availability. Imagine your own brand just beneath it showing that you had the pleasure, no the privilege, of initiating this young girl into the pleasures of sexual intercourse. One hundred and fifty guineas. Imagine reaching out and taking that underwear off to reveal the secrets hidden within that red bulge. One hundred and sixty guineas.”

Helen turned away from the men, bent over and slowly lowered her knickers to her ankles as Mr Christie shamelessly increased the price.

“Look at that pussy. Look at those delicious pink lips. Imagine your tongue as it slides between those lips tasting Helen’s nectar. I’m sure her clit is hard with excitement at the prospect of being fucked by you. Two hundred and ten guineas, two hundred and twenty guineas.”

Helen turned back around, now completely naked. She squatted down in front of the crowd letting them see her pussy up close, her pink inner labia framed between her outer lips like delicate rose petals.

“Look at those beautifully shaved pussy lips, imagine parting them with your fingers so that you can put your tongue on her hard clit. Two hundred and fifty guineas.”

Helen put one leg up on the chair so that the flower of her pussy blossomed before the now smaller audience of serious bidders in front of her. She reached down with one hand and opened up her outer lips.

“Look at her clit standing proud and enthusiastic, just ready for your tongue and your fingers to bring her to orgasm. Two hundred and eighty guineas.”

Helen reached down with her other hand and started to stroke her clit slowly and sensuously. A few men came back into the auction but the price was getting too high for most of the audience, even rich merchants. But there were still three men enthusiastically stroking their hard cocks. Others were clearly frustrated that they did not dare touch their hard cocks for fear of accidentally making a bid they could not afford.

“Watch her pleasure herself as she does every night. Imagine getting her to masturbate for you and your guests before they watch you fuck her for the first time. Three hundred and thirty guineas.”

Helen was really turned on by the pleasure that everyone was taking in her body and her sexuality. Even the auctioneer’s patter was a turn-on. She felt close to cumming.

“Just think how pleased your friends will be that you invited them to such a special party this evening. How much they will enjoy taking Helen in their turn after you have initiated her with her first fuck. It will be an evening that will be talked about all over town. For those that can afford it, buying a young girl’s virginity is the ultimate in fashion right now, but a young girl from Charing Cross school is la crème de la crème.

“And don’t forget the Charing Cross tradition. If you win the bidding you will be able to fuck Helen not just tonight but once a year forever. Imagine how jealous your friends will be of your not-so-secret mistress.”

This thought increased the number of bidders again, but as the price increased over four hundred guineas, the number of bidders stroking their cocks dropped until there were just two left. They stroked their cocks vigorously. Excited by the grandeur and ceremony of the occasion, Helen let herself finally cum just as the last bidder dropped out and Mr Christie brought down his gavel to close the auction.

Mr Christie smiled to himself at the final amount, five hundred and twenty guineas, an astronomical sum. Helen smiled to herself as she thought of the adventure that she was sure would be in store that evening.

“I’m sorry Lord Bristol,” Mr Christie said, turning to the man who had finally been forced to drop out of the bidding.

He turned to the winner. “Sold to the Prince of Wales, host of the most outrageous soirées London has ever seen. Tonight’s will be exceptional I’m sure.”

At that moment the Prince of Wales came, the tension finally released as globs of white cum shot from his cock, safe in the knowledge that he had won the auction. He would deflower Helen in front of his closest friends that evening.

Chapter 5: The Prince of Wales

Helen was taken back to the room where she had spent the previous night. She would be taken around to the residence where the party would be held that evening, once Christie’s had received the money safely. The man who had advised her that morning returned.

“Did that go OK?” Helen asked.

“It was an excellent price,” he told her. “I believe it is easily a new record. It is the first time a member of the royal family has ever bid, a true compliment.”

“The Prince of Wales. I can’t believe it. I mean I’ve imagined the first time I fuck many times but never in my wildest dreams did I consider royalty might deflower me.”

“Being auctioned to the Prince of Wales should be fun. I’m sure that there will be lots of famous and beautiful people there this evening. It will be the most fashionable party all year. High society will be sure to be dressed at the cutting edge of fashion, and I’m sure that there will be a few adventurous actresses there too to help liven up the proceedings.”

“What do I need to wear?”

“You must wear something very dramatic.”

He went over to the wardrobe. “First, a white thong for virginity. Then I think a tight top that comes just down below your breasts leaving your stomach bare. A black ankle length cloak for a dramatic unveiling. After you enter the room you will give erotic flashes of leg when you walk. Then when you take off the cloak everyone will be stunned at how little you are wearing, just a tiny thong covering your sex and a small top stretched tightly across the swell of your breasts.”

It was not long before Helen was in a carriage on her way to the Oscar Wilde residence in a fashionable part of the city, where apparently the party was to be held. A manservant opened the door and showed her upstairs to the drawing room. There were about twenty people in the room, a few women sprinkled among the men. All eyes were on her as she entered since nobody there had been at the auction. The Prince of Wales came over and took her arm and introduced her to everyone. She kept the cloak on for the time being. The other guests turned out to be a roll-call of the rich and famous of the beau monde of Victorian society, although having been cloistered in the orphanage for so long Helen had not heard of most of them.

Having been kept away from men for years, Helen was starting to get aroused just by being surrounded by a cadre of beautiful people, knowing that they were there to watch her. She slipped off the cloak and stood there in her small white outfit. People, women as well as men, could not keep their hands off the naked skin that she was showing, and she felt their fingers touching her as she moved around the room.

The Prince called for silence and made a short speech about how he had purchased Helen’s virginity for their pleasure and entertainment. This party was already the peak of the social season that year and Helen’s defloration would be the climax of the party.

“Before we watch me fuck Helen, I believe that she could do with some guidance. Since she is a virgin, it think it would good for her to see two other people have sex first, both to get her in the mood and to educate her.”

He took the hand of one young woman and led her to the front of the crowd. She was very pretty, wearing a dress that showed off her figure, very revealing for the age.

“Jane,” he said. “Since you are the most beautiful woman and all the men in London and most of the women want to fuck you, why don’t you show her? You can have any man of your choice.”

Jane walked around the room inspecting all the most young and handsome men, seeing in their eyes their desire to be selected. Finally she chose a man who turned out to be called Simon. He was tall and looked athletic, wearing a silk shirt and britches.

He stood in the centre of the room as she circled around him. She reached out and slowly unbuttoned his shirt, running her hands over his chest. Next she unlaced the leather thong up the front of his britches and pulled them down leaving him standing there naked. His cock hung down, not quite erect yet but looking huge since he was partially aroused. She pulled her top over her head and showed everyone her firm breasts. She slipped off the short skirt that she was wearing. She too was dressed in a thong. All eyes were on the small yellow triangle at her crotch that covered a sight that the whole city would have liked to see. Slowly she slipped the thong off revealing first her blond pubic hair and then the lips of her sex.

She went back over to Simon. She put out her hand and pretended to stroke his cock. Although she never in fact touched him, the thought of her stroking his cock made him hard and as his cock rose just beneath where her hand stroked the air. She made him lie down on the rug, his cock now rigid pointing along his belly. She put one foot on either side of his head as he looked up between her legs. Slowly she squatted down until her pussy was just above his mouth. As everyone gathered round to watch, Simon’s tongue gently licked Jane’s pussy. She moved slightly so that the tip of his tongue was right on her clit. She was clearly very excited, by the display she knew she was putting on as well as the tongue exploring the crannies of her sex.

Jane stood up and moved so that she had her feet on either side of Simon’s hips. Slowly she squatted down again. She held Simon’s cock so that it stood vertically and then lowered her body so that the head of his cock just touched her lips. She slid his cock back and forth between her inner labia, spreading her juices all over her pussy so that she was well-lubricated. Then she lowered herself slightly more so that the head of his cock just nestled in the opening to her pussy. Slowly she let the head of his cock slide into her. Helen watched fascinated. It looked so different to the girls in the orphanage fucking themselves with the hairbrush as the pink head of Simon’s cock disappeared between the pink lips of Jane’s pussy. Jane’s hips started to rise and fall, at first imperceptibly and then more, as more and more of Simon’s cock disappeared into her body. Finally she had his cock completely in her, her body pressed hard against his when she lowered herself, his cock almost coming out of her pussy when she lifted up. She leant forward and lay along Simon’s body and kissed him. She held herself stationary and his hips started to rise and fall. Everyone behind her had a perfect view of his cock sliding in and out of her pussy.

Helen thought how incongruous the scene was. The two naked bodies fucking vigorously while she stood there in less than she normally wore for underwear, and everyone else in the room still in demure formal dresses and suits.

Jane and Simon rolled over so that she was now on the bottom. She spread her legs wide as Simon’s hips thrust between them. She came, breathing deeply as the pleasure spread through her whole body. And then Simon was coming too. He pulled out of her and white ropes of cum spurted onto her belly.

“Excellent,” said the Prince. “I think that that has got us all in the mood. Now it is time to unwrap my present.”

He came over to Helen and stood behind her. He held the sides of her bra and slowly pulled it up over her head releasing her breasts. He reached around and stroked them, before lightly pinching her nipples. She gasped with pleasure. It felt so different from when she touched her breasts herself.

The Prince held the sides of her thong and slowly pulled it down until it fell the rest of the way under its own weight. She felt his fingers as they crept down across her belly, lightly stroking her. His hands moved lower across the sensitive skin where her pubic hair had used to be and entered the crack of her sex. She could feel his erection through his clothes where it pressed against her cheeks. She could tell she was very excited as his fingers found first her wet opening and then returned, stroking her inner labia before lightly touching her erect clit.

The Prince pushed Helen over towards a low Chesterfield sofa. When the back of the sofa hit the fronts of her thighs, he bent her over it so that her upper body rested on the cushions, her bottom almost in the air. She parted her legs. She felt his fingers between her legs, stroking the length of her sopping wet sex. Two of the actresses came over and, while he continued to finger-fuck Helen they undid his shirt and breeches and undressed him. His large cock sprang free. He pulled his fingers out of her pussy and she felt something larger just in the entrance to her body. She was hungry to be penetrated. He thrust forward roughly and in a single movement buried his cock deep in her body. She cried out with a mixture of surprise and pleasure at the wonderful feeling of a cock sliding inside her cunt for the very first time. He started to fuck her vigorously, long hard fast strokes. She felt his belly crush into her cheeks on each stroke as he buried his cock all the way to the bottom of her pussy, could feel the sack of his balls where it banged on her pussy-lips. An orgasm came out of nowhere and took over her body and she cried out involuntarily at the intense pleasure.

She noticed that clothing seemed to be falling to the floor around her. Actresses had their hands around cocks, fingers in their pussies and on their breasts. Sounds of arousal all round the room. She felt the rhythm of his thrusts change as he came, the feel of her pussy changed as his cum emptied into it. The Prince of Wales had her virginity. Deflowered by the heir to the throne. She couldn’t wait to have sex again.

She did not have to wait long. Before she could get up, another man moved behind her and the Royal cock was replaced by his. As the unknown man fucked her from behind, another cock was pushed into her mouth and she started to lick it. Someone else reached underneath her body and started to pinch her clit. It did not take long for her to be cumming again.

During the evening she fucked everyone. Whenever her cunt was vacant it wouldn’t be long before a cock or a tongue would be in it. As soon as a man blasted cum into her mouth, a new cock or a pussy would be offered for her to lick. All evening, her whole body was a bundle of total arousal, quivering with a level of excitement she had never before experienced.

Just before everybody left, two of the men pulled Helen over to the hearthrug and lay her face down on it. One of the men sat with his weight on her back and one on her thighs. The Prince of Wales took a small branding iron out of the fire in the grate. Helen could barely move under the two men as the Prince pressed the iron to her ass-cheek. She felt the jolt of pain on her buttock as she was branded with his Royal seal. The two men got up. The Prince rubbed a cool ointment onto her ass and soon his fingers slipped lower, rubbing the greasy ointment between her swollen pussy-lips. As she lay on the hearthrug, he moved behind her and she felt his cock nestle once again in the entrance to her body. Slowly he pushed into her, well-lubricated with both her own juices and the ointment. She pushed back against his thrusts, letting sexual arousal distract her from the throbbing pain where she had been branded.

Finally late at night the Prince of Wales took her up to his bedroom and they fell into a contented sleep.

Chapter 6: Training

The next morning a coach came to take Helen to be trained in the sexual arts. She was taken to what appeared to be an innocuous boarding house but was in fact a very discreet college, officially known as Buckingham College but colloquially called Fuckingham College. Discerning ladies and gentlemen would send special servants to the school, or even send their teenage children for an education that was not covered in the normal school curriculum. Many Victorian men had mistresses, of course, but the smartest thing to do was to employ a sexually trained maid so that top-quality sex was available at all hours right under the noses of their wives. Or wives would arrange that a footman or a butler would have some extra skills that their husband did not know about.

When Helen arrived she discovered that she was to share the room with another girl called Annie. She was very attractive. She was a servant at a Duke’s house in the country, working in the kitchen. One day she had been summoned up to the entrance where there was a coach waiting and she was brought here to the college. The two girls were still getting to know each other when the door opened. A smartly dressed older man entered the room.

“Hello,” he said, “I’m James and I am the assigned tutor for the two of you. The format of the course is that I will spend the evenings with you in your room giving you personal instruction. During the day we will be with the other young men and women on the course so that everyone on the course gets a wide range of sexual experiences with different people.

“I see from your paperwork that you, Annie, have an extensive grounding in all aspects of sex but with a single partner. Yes, everyone knows that the butler has been fucking you. But you passed his test and are now being promoted. I’m sure the Duke will love experiencing you for himself once you are fully trained. It also says that you also need to improve your anal technique.”

James turned to face Helen. “You have almost no experience of sex and so need to build up basic experience with a range of different partners. You need to be prepared for anal sex but initiating you into that particular pleasure will be for your eventual owner.”

Helen had no idea what he was talking about. She didn’t know the word ‘anal’.

“I am going to start the day,” James continued, “by seeing what level you are at by fucking you both. So first I want you to undress. From this morning until your final exam you will not be wearing any clothes. Helen, why don’t you start by helping Annie out of her dress.”

Helen moved behind Annie and undid the buttons up the back of her dress that she would not have been able to reach herself. Soon Annie was naked. Her body was very different to Helen’s. Everything about her was rounded. She had very large rounded breasts with small nipples. She had large rounded ass cheeks. Even her outer pussy-lips seemed to be fleshy and rounded. James, who was taller than her, bent down and kissed her as his hand started to caress one of her huge breasts. Soon his hand slid lower and a finger pushed between her plump pussy lips. Helen could tell that Annie was starting to get very excited. James laid her on her back on the bed. Annie lay there stroking herself gently as James took off his clothes. He moved between her legs and Helen watched as his cock slipped easily into her. He started to thrust into her. She continued to stroke her own clit as he fucked her. He pulled out of her and rolled her onto her front and rested his cock on the crack of her generous ass. He slid back and pushed his cock forward between her legs, sliding it back into her pussy. Her body rose from the bed to meet him, thrusting her ass back to meet him. As he fucked her, James licked a finger and started to work it into Annie’s asshole. James continued to thrust into Annie until she came. Then he pulled out, reached down and with both hands pulled the rounded cheeks of Annie’s ass wide apart. He rested the head of his cock on Annie’s asshole and gently pushed. Helen watched astounded as Annie gradually opened up to him there and his cock vanished into the smallest entrance to her body. She had no idea any such thing was even possible. He started to thrust into her ass gently. Surprisingly, Annie even seemed to be enjoying it. James let Annie come again before he finally pulled out of her.

It was Helen’s turn next. Annie helped Helen out of her dress until she, too, was naked. James’ expert fingers soon worked up her excitement and not long after she was on her back on the bed with James’ cock slipping into her pussy while Annie looked on. James pushed up her knees so that each of his thrusts pushed his body onto her clit and it did not take long before she came. As with Annie, he then pulled out and rolled her onto her front. She lifted up her ass and spread her legs for him, pushing her bottom back against him as he thrust back into her. She felt his wet fingertip on her asshole, somewhere no-one had ever touched before. As James continued to fuck her pussy, Helen experienced the feeling of a finger working into her asshole for the first time in her life. To her surprise it felt good once she’d got over her squeamishness about a finger in such a forbidden place. Helen reached underneath herself and stroked her own clit until she came again. James was thrusting harder and faster now. He called Annie over. Just before he came, he pulled out of Helen’s pussy. Annie bent over and took his cock in her mouth. She would be able taste Helen’s juices on his cock and then the spurts of white jism hit her tongue.

“Right,” said James once they all had their breath back. “I think you will both do well these two weeks and graduate with high grades.”

He led the two girls out of the room to the large hall where they met the other young men and women on that week’s course. There were about a dozen of each sex, along with the older tutors. Everyone was naked.

That morning Helen and Annie had to explore the boys, playing with their cocks and noting how they felt. They were not allowed to put the cocks into any part of their body including their mouths, but they could do anything they wanted with their fingers. At the same time, the boys would explore the girl’s bodies, playing with their breasts and nipples, before exploring the intimate ruffles between their legs. Later in the day they were taught a number of different ways to stroke a cock, sliding their oiled fingers up and down each boy’s hard cock while he told them how exciting it was. They were allowed to go all the way with the last boy and stroke him until he came. Next the boys learnt how to arouse a girl and Helen had a thrilling afternoon as each boy in turn gradually got the hang of making her come with oily fingers.

After dinner, James took Helen and Annie back to their room.

“Tonight we will experiment with blindfolds and restraints.”

James reached under the head of the bed and pulled out a chain that he ran over the bed and then clipped in at the other side. Another chain was soon in place across the foot of the bed. This time it was Helen’s turn to go first. James put a blindfold on her and then she felt leather straps being put on her wrists and ankles, a collar around her neck and a belt around her waist. He guided her over to the bed and laid her on her front over a large pillow. Soon the cuffs were fixed to the chains so that her bottom was in the air with her legs spread wide. She felt very vulnerable but it was also very arousing.

“I am going to put a plug in your ass,” said James. “Each night we will use a larger plug. You must keep the plug in your ass all night so after we fuck I will be attaching the plug to the belt at your waist with small chains.”

Helen felt an oiled tip on her asshole. James pushed the small butt-plug into her until suddenly it locked into place. Helen had expected it to be painful but in fact it felt very naughty and arousing. She felt James’ cock at the entrance to her pussy. She tried to push back to take it into her but the chains restrained her too tightly. She was frustrated that James did not push into her and she could not push onto him. Finally James relented and gradually started to push his cock deeper into her. He reached underneath her and pinched her clit as he fucked her. In no time she came, excited by the way she was blindfolded and chained almost immobile to the bed. She felt James pull out of her and a small chain ran between her ass cheeks and was attached to the belt. Two other small chains ran forward on either side of her sex, squeezing her lips together excitingly, and they too were attached to the belt. The butt-plug was firmly held tightly in her ass.

James released Helen from the chains and took off all the straps except for the belt. He removed the blindfold and put it on Annie. Soon Annie was on the bed with straps around her wrists and ankles, and a collar around her neck. James fixed Annie’s wrists to the chain at the head of the bed so she was on her back. But instead of fixing her ankles to the chain at the foot, he moved the ankle cuffs to her knees and then used another pair of chains to attach her knees to the collar around her neck so that her legs were pulled up tight showing off her pussy. He bent forward, parted her fleshy outer lips and started to lick her erect clit so conveniently offered. He let her come once before he moved and started to fuck her while Helen watched, her own hand sliding between her legs almost automatically in response to the arousing tableau in front of her. Soon all three of them were coming.

The next day back in the communal hall it was oral sex day. Everyone learnt how to pleasure the opposite sex using his or her mouth. Helen found it hard to do the exercises where the boys pushed deep into the back of her throat, which clearly they found especially exciting although it almost made her gag. Of course Helen loved being used for practice as each boy in his turn would come and lick her and make her come at least once. Even the inexperienced boys made up in enthusiasm what they lacked in technique.

So the training course carried on with communal sessions during the day having basic sex with a wide range of partners, and in the evening more specialized training from James. Plus, for Helen, each night a larger and larger butt-plug was left in her ass. By now Helen was excited as the plug was inserted, enjoying the feeling of fullness as the widest part entered her. She couldn’t wait to try a real cock in her ass. Watching Annie being done anally had been exciting.

Chapter 7: Training Week Two

James came into the Helen and Annie’s room. In his hand was a thick bamboo cane.

“Some purchasers are interested in very special girls,” he said. “Ones who are turned on by extreme treatment. To graduate in the select tier you must be able to take pain. Helen, your owner has paid for you to have this special training.”

He pulled a chair out and made Helen bend over so her head was on the seat of the chair and her ass was completely exposed. She gripped the back of the chair tightly. He made her part her legs, exposing her pussy. She felt very vulnerable in that position. She remembered her one time being caned before, in the headmaster’s study at the Charing Cross school. It seemed so long ago now although it was only a couple of weeks since she left.

“You mustn’t move your hands, bend your knees or lift up your body,” James said. “Or cry out. But tears are fine.”

Helen felt the cane against her ass cheeks. It went away. She knew that when it returned it would not be gentle. She heard the swoosh, even heard the crack as it contacted her ass. Only then did the pain hit. It was as if the cane were a red-hot iron bar that had just been laid across her. She gritted her teeth to avoid crying out.

James waited for the pain to peak and subside before he took a second stroke. Again the swoosh through the air and the crack. And then the burning pain. She felt tears starting to well up. Her knees started to go weak and it took all her effort to keep them straight, keep her ass in the air, defenseless.

The next stroke was harder. The swoosh was louder, the crack on her cheeks more intense. She yelped, unable to keep silent. She started to cry, although she tried to blink back the tears. Surprisingly, she could also feel her body getting aroused. Her pussy was fluttering with arousal and she knew she was wet.

She didn’t really hear the next stroke. Her ass just exploded in a frenzied burst of agony. She couldn’t stop herself, she let go the chair and covered her ass cheeks with her hands. James said nothing, but just stood there waiting until submissively she replaced her hands on the chair and left her ass exposed again.

There were six strokes in all. By then Helen was crying continuously, tears running down her cheeks. Her pussy, however, was on fire, flooded with excitement.

She was still bent over wondering if there would be another stroke when she felt James cock at her pussy. What a relief as he pushed into her. She stayed bent over holding onto the chair as he fucked her hard. The intensity of the pain in her ass-cheeks changed to more of a throbbing, and the pleasure in her pussy made it easier to ignore. She felt James’s hands on her hips, holding her so that he could fuck her even more roughly.

She cried out as she orgasmed. She felt her knees starting to collapse as they had during the caning. She managed to straighten her legs and even push her ass back towards James as her body filled with relief. She could barely think between the pain in her ass and the cock pumping in her pussy. James pulled out of her.

She turned quickly and knelt down as she had been trained. It was not acceptable for a man to cum except in one of her three orifices. James thrust his cock into her mouth and she used her tongue to coax the first warm jet of cum into the back of her throat.

“Not bad for a first time,” James said as he continued to spurt in Helen’s mouth.

Helen’s heart sank. That meant there would be more times, her torture was not yet over.

The following night Helen feared she was going to be caned again. But it turned out to be something different once James arrived.

“Helen, I want you to make Annie cum with your tongue.”

Despite spending years in an all-girl orphanage, Helen had never been sexual with another girl. Her only experience was licking her headmistress that last day at the Charing Cross orphanage. Annie lay back on her bed and spread her legs. Helen moved closer.

Unlike with the headmistress, Helen could take her time. She examined Annie’s pussy. It pussy was very different from her own. Whereas she had large pink inner labia, Annie’s pussy was just a fleshy mound with a long furrow down it and no sign of any labia. Tentatively Helen reached out and with the fingers of both hands she separated Annie’s outer lips revealing little pink petals hidden within. She bent forward and tasted another girl for only the second time.

She started to run her tongue between Annie’s lips. She wasn’t entirely sure what she was doing but she knew what felt good when it was done to her, and that had seemed to serve her well with the headmistress. Plus Annie was whispering guidance, telling her what felt good. She pushed her tongue as deeply into the other girl as she could, twirling it around in the entrance to her pussy. Then she would give Annie’s clit some attention, using just the tip of her tongue to tickle the sensitive little bud. Annie was moaning now, not just giving guidance but genuinely aroused. Helen felt a real sense of accomplishment when she felt Annie’s body suddenly jerk and then she was crying and groaning and shaking as her whole body was consumed in a huge orgasm.

Then it was her own turn. She lay back on the bed and Annie had to make Helen cum. Since it took so little to make Helen orgasm, it didn’t take long before Annie had her close. “Oh that’s so good,” Helen moaned as Annie worked her clit towards the final peak. A few more licks and Helen’s orgasm burst through her. “Oh yes Annie,” she squealed as she came, her body flushing pink with the intensity of the feeling.

The following day Helen was caned again. This time she was more used to it and she managed to hold the position with just a few tears. She came almost instantly when James entered her, the cane having already got her to a pinnacle of arousal just on the point of orgasm. She knew that with a few more canings to get her body fully trained that she’d be able to cum from the caning alone. It was starting to be a bittersweet experience. Despite the agonizing pain she was starting to enjoy the way it gave her a type of arousal that she could get no other way.

After fucking her, James made Helen bend over the edge of the bed and spread her cheeks wide. He had an enormous anal plug that was shaped a little differently with a sort of screw thread. He pushed the tip into her ass but instead of just pushing a bit harder as he had with the smaller plugs, he rotated it. It gradually screwed into her, distending her asshole. She had to grit her teeth to avoid crying out from the pain, it was worse than the caning. She was crying continuously from the pain by the time she finally felt the relief as the plug locked into place in her ass, the widest part now inside her. It wasn’t necessary to chain the plug in place, there was no way it would come out accidentally. Finally James left. It was their last night. Tomorrow morning it was the exam day.

Helen knew that the exam consisted of two tasks. She would be given instructions and a boy allocated to her would be given compatible instructions, one task mainly a test for her and one mainly for the boy. She would have to exhibit the ability to arouse the boy in a very controlled manner, fast or slowly as the occasion demanded, and to judge precisely how aroused he was so that she could make him come just when she wanted. Also, she would have to control her own excitement so that she could come when she chose.

James handed her a sheet of paper with her first task on it:

“Strip him naked while remaining fully dressed yourself. Without touching him, undress erotically so that he has a hard erection by the time that you are naked. You may masturbate for him if you like. Tie him face-up to the bed with rope. Using your mouth only, bring him close to orgasm while at the same time masturbating so that you are also aroused. When you judge that he is nearly coming, straddle him and take him into your pussy in a single movement. He should already be so aroused that he comes almost immediately, certainly within a minute. You must come at the same time as him.”

Helen undressed the boy that had been selected for her and followed her instructions. When she had got him just to the point of coming with her mouth, she tied his wrists to the four corners of the bed so that he was lying there with his hard cock just waiting for her. She quickly straddled him and slid his cock into her. As she fucked him vigorously she reached down and masturbated herself. As she sensed that he was about to come she let her own orgasm arrive, continuing to rock her hips back and forth as she fucked him dry.

Her second task was as much for his final exam as for hers:

“Let him lick and bite your nipples. He should do this effectively so that you are very wet just from this. He can then lick your pussy and clit and get you close to orgasm. He must then lick and finger your asshole, getting it wet and relaxed enough that he can insert a large butt-plug. While he works this into you, he should continue to lick your clit and make you come just as it locks into place. Lie on your back with your legs spread wide and take his cock into your pussy, starting with small thrusts and building up to full length ones. You should come once as quickly as possible and a second time at the same moment as him.”

Helen had very little to do during this exam other than receive pleasure and try and time her orgasms. She managed to come almost at the moment that the large butt-plug finally slipped past the tight entrance of her ass. Then she lay back for him to fuck her. She was very excited and so that she came almost immediately as he finally fully entered her and then she let another orgasm build up as the boy fucked her slowly, letting herself come as she felt his hips spasm between her legs.

James told Helen that she had passed the course in the special “select” tier. He had her lie on the table. A leather belt was tied under the table and over her body so that she was immobilized. Again the pain on her bottom told her that her pass in the “select” group had been permanently burnt onto her ass, visible to everyone she would be intimate with in the future.

Chapter 8: Second Auction

Before Helen had left the school, James had given her advice about the second auction. The first auction had been aimed at rich people wanting a trophy for one night. The second auction was aimed at someone wanting a permanent purchase. The auctioneers had discovered at some point in the past that they could get higher prices during auctions for sexual slaves by having more of a party atmosphere than would be appropriate for a fine art auction. So traditionally the auction was conducted as a roman slave auction. The auctioneer, and most of the potential purchasers in the audience, would be dressed in roman togas over their Victorian clothes, or, for the more daring, over their naked bodies. Helen, too, would be dressed in a toga although she was not surprised to learn that it would not last long and she would be auctioned naked. A famous painting by the French artist Gérôme purporting to be of a roman slave market was actually of a Christie’s auction in London.

Helen arrived at the auction naked except for her roman toga. She walked out onto the raised stage. In the middle of the stage was a large desk and Mr Christie stood to one side dressed in a mustard colored toga. There were a couple of naked female servant-girls on the stage too.

“Gentlemen, this lot is Helen. As you will have read in your catalogues, she was educated at the exclusive Charing Cross School where only girls with both academic and sexual potential are selected. Just two weeks ago her virginity was auctioned to the Prince of Wales, the heir to the throne. You might have read about the party at Mr Oscar Wilde’s that evening in one of the more indiscreet offerings from Fleet Street. Since then she has spent the last two weeks at Buckingham College, the famous Fuckingham College where she finished with a “select” grade, reflecting the high level of training that she has received over her life. And also, of course, the high level of pleasure that will be available to her eventual purchaser. She has been branded on her ass by the Charing Cross School, the personal brand of the Prince of Wales, and a Buckingham College select brand.

“Her ass has been prepared by Buckingham College so that she is cock-ready, but she is still an anal virgin. That entrance remains to be used for the first time by today’s purchaser.

“If you want to bid then you must raise your hand. I’m going to start the bidding at 200 guineas.

Many hands went up in the audience. As Mr Christie increased the price, he walked over to Helen and undid the brooch on her shoulder that held her toga in place. It fell to the floor leaving her standing there naked. The price continued to rise. She could see the arousal of some of the men in the audience, the outline of their hard cocks visible where they pushed out the material of their togas.

“Look at those firm young breasts just waiting for your attention. The nipples are already hard waiting for your tongue or perhaps your fingers. Or perhaps you think your new young slave needs disciplining with painful nipple clamps.”

Mr Christie beckoned to a couple of the girls on the stage and they brought over some cuffs and put them on Helen’s ankles as she stood naked in front of the rowdy crowd of bidders. Two more cuffs were put on her wrists. She was bent over the desk and the cuffs clipped into rings. Her arms were pulled forward. She heard a murmur of excitement go through the crowd as her legs were spread and her pussy was revealed to them. Her ankles were clipped into place at the base of the desk leaving her spread wide.

“Look at that pussy just ready for you. Those pink lips are just waiting for you to part them with your fingers, probing into the warm depths of her wet pussy, getting her ready for your cock. Or perhaps you just want to thrust into her immediately. After all she is your slave and it is her job to want sex when you do, not the other way round.”

Mr Christie ran his fingers over the sore areas where Helen had been branded earlier in the week.

“See here the brands of quality, the cross brand of Charing Cross school, the top of the line in sexual preparation. Then the personal brand of the Prince of Wales who fucked her for the very first time just two weeks ago today. And finally the brand of Buckingham College, the top college for training of discreet maids and governesses who are sexual slaves underneath the drab material of their daily uniforms. The S in the triangle of the Buckingham College brand indicates that this is a truly select sexual slave, of a type that comes to auction only very rarely so today is an opportunity that may not occur again for some time.”

As Mr Christie continued to increase the price he walked around to the back of the desk by Helen’s head. He opened up his toga revealing his half-hard cock. He reached down and placed the head of his cock in Helen’s mouth. She started to suck him into her mouth and to caress his cock with her tongue.

“Four hundred guineas. I can tell you that her mouth feels really good, all warm and wet. I can tell from her tongue movements that she has been very well trained and will love to lick your cock when you purchase her. Imagine summoning her to your study with your nightcap after your wife has gone to bed. As you sip your whisky, she bends down and opens your britches and takes your hardening cock into her mouth. I’m pushing my cock hard into the back of her throat now like you will be able to do. Perhaps you hold her head and fuck her mouth, or maybe even have her lie on her back on your desk so that her mouth is just at the right height for your cock to slide into.

“She is making me come already, she is such an expert cock licker. I’m sure you will find many occasions to take advantage of her quick mouth. You could slip out of a boring party for just five minutes for a quick orgasm.”

Mr Christie pulled out of her and the jets of his orgasm squirted across into the air, some landing on her and some on the desk.

“As I said earlier, her ass is cock-ready. To demonstrate, I will show you how easily she takes a large plug.”

One of the naked girls from the stage approached Helen and then she felt warm oil running down the crack of her ass. Fingers rubbed the oil around and just into her asshole. The girl went and sat back down again but it did not take long for her oily fingers to find their way between her own fleshy lips.

Mr Christie approached with a large butt-plug in his hand. She felt the point of it in her asshole, and then as Mr Christie pushed steadily she felt her asshole distend to admit the intruder. She was just on the point of crying out that the plug was too large when it locked into place in her ass.

“Look at that. Her asshole is already stretched enough for your cock. She has been sleeping every night all week with butt-plugs in her ass and now she will be just dying to try the real thing, the forcefulness of a real cock in her ass.

“I will select someone from the audience to fuck her now. But as is traditional I will first blindfold her so that she is unaware who it is.”

Mr Christie reached over and put a blindfold onto Helen. Now she was in a world of her own, the noise of the aroused crowd, the throb of the plug in her ass, the feeling of vulnerability that her pussy was spread wide in front of everyone and that a cock would soon be in it, the sound of Mr Christie increasing the bidding.

Helen felt oily fingers again, rubbing warm oil into the folds of her lips. Then she felt the point of a cock-head nestling in her opening. A slight pressure from the cock and she felt her pussy muscles relax to admit the cock into her slick wet hole.

Mr Christie continued to work the crowd of bidders.

“Look at the way that cock just slides into her, she is so eager for it. Imagine taking her bent over the desk in your study rather than the desk here on the stage. Perhaps you could order her not to wear anything underneath her servant’s uniform so that she is always accessible to you. Just bend her over your desk and flip up her skirt and thrust your hard cock into the enchanted coral cave of her pussy.”

The cock in Helen’s pussy started to slide back and forth vigorously. Helen found that her clit was rubbing against the wooden trim of the desk and she knew that it would not take much to make her come. Further, on each stroke the anonymous man’s belly pushed the butt-plug deeper into her ass. As the cock took her over the top she made no effort to conceal her orgasm.

“See how easily she comes, taking sexual pleasure even in a stressful public environment like this auction. Imagine how much pleasure she will take from you in the privacy of your own house. Or perhaps you prefer to provide her for the enjoyment of your friends, all fucking her on the dining table after the women have retired from the dining room to the drawing room. A fuck is so much better an accompaniment to a glass of port than a cigar.

“Or perhaps you could have some fun and tie her up and leave her in your guest bedroom ready for your guest to use her as he will. Imagine how much he will enjoy visiting your house if he gets to play with such an enchanting and arousing toy.”

She could tell from the man’s thrusts in her pussy that he was close to coming too. But he pulled out of her and she felt the warm spurts of his come as they landed on her ass.

“Look how her pussy has squeezed him dry. Two weeks ago she was a ripe virgin, now she is a fully-trained sex-maid ready to join your servants and be available to you at all hours of the day and night.”

Helen could tell from the bidding that the auction was coming to a close since it was clear that fewer and fewer people were bidding, which didn’t surprise her given the astronomical price. She had had no idea of the value of a well-trained sex-slave. Finally it was over. She heard the hammer fall and Mr Christie said “Sold”.

She felt the girls on the stage undoing her cuffs and she was led off the stage, still blindfolded, unaware of who her purchaser was or what he looked like.

Chapter 9: Bespoke Tailoring

Helen heard the key turning in the lock and the door opened. A man stood there. He was about forty, tall with black hair. Athletically built. It was a relief to Helen that he was attractive. She felt a little flutter of interest between her thighs and realized that she would not be reluctant to fuck him.

“Hi,” he said, “I’m Alasdair and I purchased you this morning. Now that you are paid for I am free to take you.”

“Pleased to meet you,” Helen said, curtseying formally.

“Let me tell you a bit about myself. I am a successful businessman living in Edinburgh in Scotland where we will be going tomorrow. I am married but my wife will just think that you are a new maid. She will not know that you are a sex-slave. Not a lady-in-waiting but a lady-in-mating, as it were.”

“We are leaving now?”

“Soon. The first thing that we need to do now before we leave London is to go and purchase some clothes for you. My carriage is waiting outside.”

Helen and Alasdair left the room for the last time and soon the horse was leading the carriage to Savile Row. They stepped down from the carriage and entered a gentleman’s outfitters.

“It would be most improper for a gentleman like me to be seen travelling to Edinburgh with a maid, so we will kit you out with men’s clothes so that you can travel as my valet or, depending on where we are staying, as a colleague.”

Alasdair and Helen went into a dressing-room at the back of the shop. A tailor soon appeared with hangers of jackets and pants, along with shirts and socks.

“Take off everything,” Alasdair ordered Helen. Helen was soon standing there in just her panties.

“Everything,” Alasdair repeated.

As she stepped out of her panties, she could feel the eyes of the tailor on her pussy.

Helen tried on various jackets and pants.

“This is a special waistcoat,” said the tailor. She put it on. As she buttoned it up it tightly, it was shaped so that it compressed her breasts and flattened out her chest. She looked at herself in the mirror, surprised at how like a young man she looked, except for her hair. If she pushed her hair into a hat the illusion was complete.

“You are not to wear panties under these pants,” the tailor told Helen. “They are special pants with a special seam between the legs that opens.”

“I think we had better try them out,” Alasdair said to the tailor.

The tailor reached down and unbuttoned the flies of the pants Helen was wearing. Then he slipped his hand inside, the back of his hand rubbing on her pussy lips, and undid hidden internal buttons opening the pants completely between her legs and starting up her behind. Alasdair pushed Helen so that she bent at the waist. She put her hands on the ground to stop herself falling over completely. She knew that her pussy must be poking through the gaping seam in the pants.

Alasdair squatted behind her and she felt his tongue gently lick her outer lips. She could feel the roughness where her hair had started to grow back. Alasdair started to lick her inner lips, pushing slightly between them to savor her nectar. He slid his tongue back further and started to lick her asshole, parting her cheeks gently with both hands. Helen could feel her clit hardening with excitement. Slowly the tip of his tongue worked its way forward again until it started to swirl in little circles on the hard pearl of her clit.

Alasdair stood up and unbuttoned his own pants. His cock was already hard. She felt the helmet of his cock in the wetness of her pussy opening and then he was inside her for the first time, savoring the pleasure of his purchase. Alasdair beckoned to the shop assistant who slid underneath Helen’s bent-over body. As Alasdair fucked her from behind, the shop assistant licked her clit. With the hard cock sliding in and out of her pussy and the tongue on her clit Helen soon trembled with her first orgasm.

Alasdair pulled out of Helen. The tailor lay on the ground and Helen squatted over his face. Alasdair moved in front of her and Helen finally got to see her master’s cock for the first time. She took his cock into her mouth. While the tailor licked her pussy, she licked Alasdair’s cock. She slid her hand inside his pants and cupped his balls. As her next orgasm washed over her, Helen felt Alasdair come and tasted the jets of cum as they shot into her mouth.

Soon they were back in the carriage. Helen was now dressed as Alasdair’s manservant. They arrived at a barber’s shop. Helen sat in the chair and soon her hair was shorter and styled like a man of the day. Alasdair was sitting in the next chair having his hair trimmed too.

“I think I could do with a shave too,” said Alasdair.

“You mean you want your beard taking off, sir?” questioned the barber.

“No,” said Alasdair as he undid his pants, “I meant down below.”

The barber got his shaving brush and soon Alasdair’s cock and balls were covered in lather. The barber took a cut-throat razor and in just a few well-practiced strokes Alasdair was hiarless. Helen wanted to reach out and stroke his smooth balls.

“He needs a little attention to his shaving too,” said Alasdair.

“Certainly sir,” replied the barber. The barber undid Helen’s pants and pulled them down around her ankles. The barber laughed in astonishment to find a pussy instead of a cock. Helen slid forward to the edge of her seat and parted her legs. Again the bristles of the shaving brush felt exciting on her lips before the cut-throat razor was sliding through her stubble leaving broad stripes of hairless smooth skin.

“An excellent purchase,” the barber said to Alasdair when he spotted the brands on Helen’s ass. “I can see she has been well-trained. Is she new?”

“Yes, I have only used her once. I was going to keep her as a treat until this evening but I couldn’t wait when we were at the tailor’s just now. I still have her asshole for later though.”

Soon Alasdair and Helen were back in his coach heading out of London into the countryside.

“People outside the carriage can only see us above our waists, so open your pants and masturbate for me,” Alasdair told Helen as he unbuttoned his own. Helen unbuttoned the flies of her pants and then the secret buttons that completely opened the seam between her legs. Meanwhile Alasdair reached into his bag and brought out a large wooden butt-plug. He passed it across to Helen.

Helen took the butt-plug and licked it. Then she pushed it into her pussy, already starting to be wet with excitement. Finally, she placed it on the rosebud of her asshole and slowly pushed it into her body.

Helen opened up her sex so that Alasdair had a good view of her pink lips and the base of the butt-plug buried in her ass. She watched Alasdair’s cock harden as she languorously stroked her clit. She looked out of the carriage window.

There were Victorian ladies and gentlemen going about their business, occasionally glancing at her through the window. It amused her to think how shocked they would be if they knew what she was doing out of sight below the window. Helen turned back to find that Alasdair had started to stroke his hard cock. She was nearly coming. She looked through the carriage window again and stared straight at a prim looking woman walking down the street as her orgasm erupted, all private volcanic female excitement below her waist, modest public manservant above.

She knelt down, completely out of sight of the window now, and took Alasdair’s cock in her mouth. The rocking of the carriage meant that his cock moved over her tongue without her having to do much. She stroked the tip of her tongue on Alasdair’s most sensitive spot, and soon he was coming in her mouth while he looked through the window at the outskirts of the city.

As it started to go dark the carriage pulled into the yard of a coaching inn in the countryside north of London. The butt-plug had been moving excitingly in Helen’s ass as the carriage rolled over the cobbles. Alasdair and Helen checked into a suite of rooms. Once the door was closed Alasdair wrapped his arms around Helen and kissed her. She could feel his erection press against her body as she felt her own juices start to run.

“It will be several days journey to get to Edinburgh,” he said. “It will be great fun finding out just how well-educated you have been. Is there anything in particular that you would like?”

“I want you to fuck my ass,” Helen replied. “I have had larger and larger butt-plugs in it all week and the one I have had in there all afternoon has made me hungry for a real cock. I want to know what ass-fucking feels like.”

Helen stepped back and took off her jacket and shirt. Then she took off her pants and stood naked. She went over and lay face down over the edge of the bed. The black base of the butt-plug was like a target in the centre of her ass. Helen parted her legs so that Alasdair had a good view of her sex. She reached back between her legs and started to stroke her clit. Alasdair watched while her excitement grew until she came. She squeezed her ass tightly and forced the butt-plug from her body. It fell to the carpet. Still lying over the edge of the bed she opened a small glass vial. She reached back and poured oil at the top of the crack of her ass. As the oil ran down between her cheeks she rubbed it on her asshole, and then pushed two fingers into her ass to ensure that she was completely lubricated, and also to put on a show for Alasdair.

Alasdair stepped up behind her. He placed the head of his cock on the centre of her asshole and pushed. She was so ready to be fucked that the tight ring of her asshole just opened up as his wide cock distended her. It felt like a form of extreme sex, a taboo pleasure of her body that most women never discovered. Alasdair’s cock started to slide in and out of her ass. Helen moved her hands back to her clit, now slick from the oil. As Alasdair drilled her ass she roughly rubbed her clit. The excitement of being fucked up her ass soon brought her to orgasm. Alasdair could feel her come, feel the tightening of her muscles as her orgasm pulsed through her pussy and ass.

Alasdair pulled out of Helen’s ass and lay on the bed. She squatted over him and positioned his cock on her asshole again before sinking down onto him until his balls were pressing against her cheeks. Alasdair reached between her legs and started to gently pinch her clit as she started to fuck his cock again with her ass. He reached up with his other hand and twisted one of her nipples sending waves of painful excitement through her body. Alasdair slipped a couple of fingers into her sopping pussy. Helen was in heaven with fingers fucking her pussy and a cock in her ass. In no time she came again.

She lifted herself off Alasdair. He got off the bed and sat on a chair, his cock sticking up temptingly. Helen came over and turned her back to Alasdair and straddled his legs. She reached between her legs and grabbed his cock, positioning it once again on her asshole as she sunk down onto him. As Alasdair thrust vigorously up from the chair Helen stood over him enjoying the intensity of anal sex. She could feel that Alasdair was close to coming. A few more hard thrusts and she knew he was pumping come deep into her ass for the first time in her life.

Chapter 10: The Innkeeper’s Daughter

Alasdair and Helen went down to the bar of the inn to get something to eat for dinner. They sat down at a table, Helen sitting gently since her ass was still a little sore from its first pounding with a real cock. They were served by a very pretty young woman.

Alasdair leant over after she’d just refilled their wine glasses. “I think she fancies you,” he said. “The way she can’t keep her eyes off you.”

“Really? I hadn’t noticed.”

“That’s because you are not used to being a boy. You should try and seduce her.”

“How do I do that?”

“Just start by showing an interest. Talk to her. Try and keep her talking.”

The girl came by with another dish.

“What’s your name?” Helen asked her.

“Nellie, sir.”

“Have you worked here long?”

She laughed. “All my life. My father is the innkeeper.”

“What age did you start?”

“I don’t really remember. Seven maybe. Once I could carry a beer mug without spilling it.”

“Do you have desserts here?”

“Yes. We have various cakes. I make them myself.”

“A good baker as well as a pretty girl.”

She blushed.

“Thank you, sir.”

“I think we’d like to have some cake then. Whatever you are most proud of.”

“Certainly, sir.”

“But up in our room. It’s too noisy in here in the bar.”

Nellie went away to the kitchen.

“Good idea,” Alasdair said. “Getting her to come to the room.”

The two of them got up and climbed the stairs to their room. About ten minutes later there was a soft knock on the door. Alasdair got up and opened the door. Nellie came in with a tray.

“I brought you some more wine too,” she said, as she put the tray down on the table. “So where are you gentlemen from?”

“Edinburgh,” Alasdair said.

“That’s a long way from here. I’ve been to York.”

“That’s quite far too,” said Helen, remembering some of her geography lessons.

“A day’s ride. I went on my own.”

“Wow. You are adventurous.”

“That was during my tomboy phase. My father was cross. He said it was dangerous.”

“What sort of danger?”

“Being robbed. But I hardly had any money so there wasn’t anything to steal. Or being…you know…a boy and a girl.”

“A boy and a girl?” said Helen, feigning ignorance.

“You know.” Nellie made a circle with finger and thumb and pushed a finger from her other hand through it.

“Ah, I didn’t think of that. I’ve not done it yet. Have you?”

Nellie blushed, clearly too embarrassed to answer.

“I’ll take that as a yes,” Helen said, reaching out and putting a hand on Nellie’s ass. She could feel Nellie’s ass-cheek through the thin material of her skirt.

“I’d better get back downstairs,” Nellie said.

“No. Stay here for a bit. A pretty baker makes a cake even better.”

Helen picked up one of the cakes off the plate and took a bite.

“Wonderful,” she said. “What is it called?”

“It’s called devil-cake.”

“Oh that’s a horrid name for something so sweet. It tastes like a princess’s pussy, that’s what it should be called.”

Nellie blushed again.

“I bet yours tastes just as sweet,” Helen said, wondering if she’d gone too far. She moved her hand and gently stroked Nellie’s ass. It was a good sign that Nellie made no effort to move away.

Nellie stood there, torn between running away and letting the young man she fancied go further. Helen stood up and, before Nellie could react, she kissed her.

“Mmm,” Helen said. “Those lips taste sweet…I’m sure your nether lips taste even sweeter.”

Helen put her arms around Nellie and kissed her again. Nellie didn’t respond at first and then suddenly she started to move her lips. Helen pushed her tongue forward and found the servant’s own tongue. She let one of her hands slip up onto Nellie’s breast. Nellie let out a little sigh of pleasure. Helen felt Nellie’s nipple through the cotton of her top, felt it hardening as Nellie’s arousal increased.

As Helen continued to kiss Nellie, she let her hand slip from her breast and descend to the front of her skirt. She cupped her fingers and pushed against the rough fabric, feeling the outline of Nellie’s pussy through it, feeling the soft fleshiness of her mound. Nellie moaned and started to move her tongue more urgently in Helen’s mouth as Helen started to rub her softly.

Helen led Nellie over to the bed. As if in a daze Nellie lay down and didn’t put up any resistance as Helen stripped her naked. Nellie had a beautiful body that the plain servant’s clothes had done a good job hiding. She had an hourglass figure. Her breasts were very firm, almost conical, topped with surprisingly puffy nipples that stuck out, hard with excitement. She had long shapely legs. And where they came together was a fleshy mound crowned by a little triangular patch of sparse black pubic hair, not thick enough to hide the deep slash of her slit.

Helen parted Nellie’s legs to reveal the pink folds of her pussy, her nether lips as she had called them earlier. She bent forward and ran her tongue over them. Nellie moaned a little the moment Helen’s tongue touched her pussy. Helen fluttered her tongue over Nellie’s creases, probing into her cunt, nudging against her clit. She moved her hands up Nellie’s body and rubbed her hard nipples. It didn’t take long for Helen to have Nellie moaning continuously, lost in her own world of arousal as Helen expertly licked her pussy as she had been trained the week before. Helen smiled to herself when she remembered Nellie believed it was a boy between her legs.

Helen slid a finger into Nellie as she focused her tongue on her clit. She slid her finger back and forth inside her tight cunt while her tongue drove Nellie’s arousal higher and higher. Nellie groaned and her whole body twitched and then she was sighing and panting and shaking as Helen powered her orgasm to its climax with her finger and tongue.

Helen moved onto the bed and lay down. She took Nellie in her arms and kissed her again, driving her tongue into the innkeeper’s daughter’s mouth. Helen’s hand slid down onto one of Nellie’s breasts. She took her nipple between finger and thumb and pinched it hard as the two girls’ tongues jostled and jousted.

“Oh sir,” Nellie moaned, “Fuck me sir. I can’t wait.”

Nellie reached down and pushed her hand into the waistband of Helen’s pants. Her eyes flew open as she reached Helen’s pussy and discovered that she didn’t have a cock, that she was kissing a girl.

“You’re not a man,” she shrieked.

“No,” said Helen. “But don’t stop now. Frig me.”

Nellie pushed her hand further into Helen’s pants until she was fingering her pussy. Helen was very wet. It had been so exciting tonguing Nellie’s pussy while she believed a boy was licking her.

“I’ve never done this,” Nellie said. “It’s a sin.”

“Mmm, but like so many sins it is wonderful.”

Helen reached over and started to finger Nellie while Nellie’s hand continued to explore the first pussy she’d touched other than her own. She found Helen’s entrance and pushed a finger into her, eliciting a long groan from Helen as she felt her vagina being infiltrated by the servant-girl.

Alasdair, who was sitting watching as things unfolded, got up. He undressed. His cock was already rock hard from watching as the scene unfolded. He moved between Nellie’s legs and positioned his cock so it nestled in the entrance to Nellie’s body.

“Oh sir, yes sir, fuck me sir,” she moaned.

Alasdair pushed forward, sliding the entire length of his cock into Nellie’s pussy, already wet and aroused from Helen’s tongue.

“Oh sir, you are so big,” Nellie moaned.

Alasdair started to fuck Nellie, long slow strokes of his cock into the young servant girl. Helen got up and slipped out of her own clothes. As her clothes fell to the floor she went from looking like a boy to being, without a doubt, a girl. Now all three of them were completely naked.

Alasdair lifted himself up off Nellie. Helen moved and squatted over Nellie’s face. She lowered her pussy. Nellie wasn’t really sure what to do but she licked Helen’s pussy anyway, pushing her tongue inside her. Alasdair kissed Helen while he continued slowly fucking Nellie.

Helen moved her pussy back and forth over Nellie’s mouth, savoring the feel of her tongue on the different crevices of her lips and clit. The soft vibrations of Nellie moaning added to the stimulation. Helen looked down at the arousing sight of Alasdair’s cock sliding in and out of the young servant.

Alasdair pulled out of Nellie. Helen rolled Nellie over onto her front. She pulled her legs up underneath her so her ass was in the air, her pussy once again offered to him. Helen wrapped her hand around his cock and guided it back into Nellie’s opening. Nellie pushed back as he slipped back inside her cunt.

Helen moved behind Alasdair and lay down underneath his legs. She licked his heavy balls as he continued to fuck Nellie vigorously. She reached up and one of her fingers found Alasdair’s asshole. She gradually worked her finger into the tight ring.

Helen sensed that Alasdair was about to cum. She moved out from underneath him. Just before he came, he pulled out of Nellie. Helen wrapped her mouth around his cock. She felt his cock jerk against her tongue and the familiar taste of his cum fill her mouth. Nellie moved up the bed too and Helen yielded her place so she, too, could wrap her mouth around Alasdair’s cock and taste the thick spurts of cum.

Almost immediately Nellie leapt up and started to pull her clothes back on.

“I need to get back downstairs,” she said. “Everyone’s glasses will be empty.”

She ran out of the room doing up the bow on her apron as she went.

“Well, that was fun,” Alasdair said. “The look on her face when she discovered you had a pussy and not a cock was priceless.”

“She was brave to just carry on,” Helen said. “She’d never played with a girl before.”

“Let’s have another glass of wine and then, I think, I’m going to fuck you before bed.”

Chapter 11: Housemaid

For the next few days their journey to Edinburgh continued. Eventually they arrived at Alasdair’s house in Edinburgh’s fashionable New Town. Helen turned back into a woman again and joined the staff of Alasdair’s household as a housemaid. At work, Helen had to wear her Victorian uniform: an ankle-length black dress with a white collar and cuffs, a white pinafore apron, and a white cap. Helen felt very demure in her all-covering dress and enjoyed the way it hid her body.

Of course Alasdair had regularly summoned her to his study on some pretext or other and taken her. His favorite seemed to be to flip up her skirts onto her back. He preferred that she wore no underwear but sometimes he caught her unexpectedly and she hadn’t had time to remove it, in which case he would pull it down roughly. He’d bend her over his desk and take her aggressively from behind. He didn’t usually care about her pleasure, only his own. But somehow, being taken hastily like that, as if she was just a hole to be used, turned her on and she usually orgasmed before he did.

Other times he’d have her strip naked and then kneel submissively between his legs and suck him until he blasted into her mouth.

One evening the bell rang in the kitchen. Helen was on duty and went up to the drawing room where Alasdair was playing cards with three friends. She went into the room.

“Bring us a decanter of malt whisky,” Alasdair told her.

“Certainly, sir. I’ll bring a jug of water too.”

“Your new maid is rather cute,” said one of the friends.

Helen turned to go and fetch the whisky.

“Yes, much prettier than the last one,” said on of the other friends.

Helen started to blush a little as she opened the door.

“Can we have a proper look at her later?” asked the third.

“Absolutely, Richard” said Alasdair as Helen closed the door.

Helen wondered what that last remark had meant as she went down the back staircase to the butler’s pantry where the whisky was kept.

While she was gone, the men continued to discuss her.

“Have you fucked her yet, Alasdair?” asked one of the friends who was called Iain.

“She looks so young and innocent,” said Alasdair ambiguously. “From the tone of your voice it sounds like you would you like to fuck her?”

“Definitely, what do you think Angus?”

“Yes, I like them young so they are just being initiated into the excitement of sex.”

“Well,” said Alasdair, “we can play cards for her when she returns with our drinks. The winner of each hand gets to remove a piece of clothing and can play with any of her body that is exposed. Once she is naked, the next winner gets to fuck her on that sheepskin rug in front of the fire.”

“I think that once she is naked we should have her put a little show on for us before we fuck her. Let’s make her come for us. I love to see a young girl pleasure herself to the heights of ecstasy.”

Helen returned to the room with a tray containing the whisky, water and glasses. She was aware of the eyes of all four men on her as she poured each of them a whisky. She was turning to leave when finally Alasdair spoke.

“Stay for a bit. We might need you and it is so tedious having to ring downstairs all the time. It’s time someone invented a way to speak in here and have the sound come out in the kitchen. A sort of voice telegraph would be very useful.”

Helen wasn’t sure if she should sit down, but she stood demurely to one side as the men started to play cards again. She didn’t know the game that they were playing but clearly Iain had won the hand.

“I win the first piece of clothing. But since it is just an apron it is a bit of a pyrrhic victory.”

“Come over here and stand by Iain,” ordered Alasdair.

Helen moved over. To her surprise, Iain reached behind her and undid the bows on her apron and caught it as it fell to the ground. Meanwhile Alasdair had dealt cards again and the men continued as if everything was completely normal.

Angus won the next hand and Helen was ordered over by him. He stood up, walked behind her and slowly undid the buttons down the back of her dress. Then he slid it off her arms and let it fall to the floor around her ankles.

She was left in a corset and her knickers. Angus ran his hand down her back, over her bottom and down the backs of her naked thighs.

“Her thighs are like silk,” he said. “Part your legs a little,” he said to Helen who had them clamped tight together. Reluctantly she parted her feet a bit. She felt Angus’s hand on the private inner skin of her thighs. She expected to be horrified by the treatment but his gentle fingers seemed to excite her rather than frighten her.

Alasdair won the next hand but as the host he allowed Richard the next piece of clothing. He undid the bow on the long lace that tightened her corset, releasing her body from its constriction. He pulled the lace completely out of the corset and it fell to the floor. Helen’s hands instinctively rose to cover her breasts.

“Put your hands behind your back,” said Alasdair to her quietly. She demurely did as ordered, the pose sticking her breasts out provocatively. She was embarrassed to feel that her nipples were hardening, pointing out like flint arrowheads. Richard, still standing behind her, reached around her and stroked her firm breasts, his fingers getting closer and closer to her nipples before taking them between his fingers, at first gently and then more roughly.

“She has marvelous breasts. Quite big for such a short girl. I must just have a quick kiss before the next hand.”

He turned her round, and to her surprise bent down and took one of her nipples between his teeth, his tongue flicking over the end of it. Helen felt a tremor of excitement extend from her nipple straight between her legs. She could feel her clit stirring, awakening. She was down to just her knickers when the men dealt the next hand.

Angus won again, and without being asked Helen went round the table to where he was seated. He reached out and took her knickers and pulled them down over her hips and let them drop. She stepped out of them. She was completely naked, aware of the men’s gaze on her freshly revealed sex, the triangle of dark pubic hair crowning her prominent lips. Angus put out a finger and gently stroked her lips. Then he stroked a little bit more firmly, his finger pressing into the cleft. Without realizing she was doing it, Helen was rocking her body against his finger as it stroked her. He pushed in between her lips harder.

“She’s very wet,” said Richard.

“Good,” said Alasdair. “Do you want to make her come now?”

“Not yet. I want to taste her and then let’s have her make herself come.”

Richard crouched down in front of her and she felt his tongue insinuate itself into her crack. She moved her feet apart a little and felt his tongue start to go deeper, seeking out and finding her clit causing a spasm of excitement.

“Very tasty,” said Richard standing up.

“Lie down on the hearthrug and masturbate for us,” ordered Alasdair.

Helen was very surprised. Masturbation was supposed to be against all Victorian morality. Helen always felt guilty after she had masturbated. Nevertheless she masturbated every night, just as she had done in the dormitory at Charing Cross, in the servants’ bedroom that she shared with two other servant girls. They read their bibles each night and didn’t appear to masturbate at all. Or perhaps they were even less obvious than Helen who had learnt to masturbate without revealing any obvious signs.

Helen lay down on the sheepskin rug in front of the coal fire. If she was going to masturbate for them then she may as well put on a show. She started by stroking her breasts, pinching her already hard nipples. Then she slid her hands down across her stomach. Keeping her legs together she started to lightly stroke her lips. Her finger slid deeper into her cleft, slipping out of side into her sex hidden by her legs. She was not surprised that her clit was so hard, erect with a mixture of excitement and trepidation at what might be to come. As she stroked her clit she slowly parted her legs so that the men could see her sex. She reached down with her other hand and opened up her lips. She was surprised that she was already so close to coming. As she came closer, she slid two fingers into her wet pussy and fucked herself as she rubbed her clit hard. Instead of disguising her orgasm as in the servants’ bedroom, she moaned heavily, breathing deeply as she came. Then she put her hands down at her side, unashamed of her nakedness.

To her surprise, the men turned back to the table and were once again engrossed in the cards. They seemed to be taking this hand very seriously. Finally Iain won. He got up and the other three men moved their chairs into a line as if they were watching a show. Iain came and sat on the rug beside Helen.

“Unbutton Iain’s pants,” Alasdair ordered Helen quietly.

She reached over and slowly unbuttoned the fly, trying unsuccessfully to avoid brushing his hardening cock.

“Get his cock out and suck him until he is hard.”

Helen grasped his cock. It seemed so large in her small hand. She bent over and licked the knob. She reached underneath and caressed his balls as she took him into her mouth, feeling his cock start to become hard. She stroked his shaft with her hand as she worked her tongue on the head of his cock, running the tip of her tongue around the edge of his knob. Then he pushed her back on the rug. She lay on her back and pulled her knees up to her shoulders hiding nothing from her audience and blatantly offering her sex to him. He knelt in front of her and placed the head of his cock in the opening to her pussy. She rocked her hips up taking him partially into her, then rocked more taking him deeper. He lay across her body and started to pump his hips, plunging his cock all the way to the head of her pussy. It did not take long until he came, his hips thrusting hard against her body almost making her come again. Iain stood up and buttoned up his fly.

“Excellent, Alasdair. I don’t know how you are so successful at finding such maids.”

Helen remained lying naked on the hearthrug. Soon the three guests were leaving, already talking business again. Since Helen was still naked, Alasdair left to show his friends out himself. Helen was gathering up her clothes when Alasdair returned.

“You did well tonight, Helen. Iain is a very important client and I think I will be doing lots of business with him. He is very keen to return but he knows I won’t invite him until I get an order from him.”

Alasdair took a sip of his whisky.

“You are very pretty tonight. I think I shall fuck you too before I go to bed. But since you were so good this evening I shall let you choose your favorite position.”

“I love being fucked from behind, sir.”

Alasdair stood up and started to unbutton his shirt. Soon he was naked. His cock was nearly hard from the evening’s earlier display. Alasdair lay down beside Helen and kissed her mouth. Then he worked lower, toying with her nipples, before the tip of his tongue ended up on her clit, already hardening again. He felt her body tremble as she was close to orgasm.

“Move onto your front.”

Helen moved onto all fours and spread her legs and lowered her head to the rug, offering her pussy to Alasdair. Alasdair noticed that the three brands on her ass had now healed completely and formed brown scars that would convey her early sexual history to the initiated. He bent down and licked her, pushing his tongue into her pussy. He moved higher, running his tongue over her asshole. Then he knelt behind her, reached down and opened up her pussy with one hand and pushed his cock into her wet depths.

Alasdair knelt almost motionless and let Helen do all the work, fucking him from in front of him, pushing her body back hard against his. Since he had stopped licking her on the point of orgasm, she came herself in no time. Then she kept going, thrusting his cock deep into her until she heard him come, felt his jets inside her.

They lay there for a short time, and then the clock suddenly struck 1am. Alasdair got up and put his clothes on.

“Before you go to bed, leave a note for the other maid to bring my wife and me tea at 8-o-clock along with the Times newspaper.”

He left the room and she heard him going up the stairs to the master bedroom suite.

Helen reflected for a time on how she had ended up as a special sexual maid in Alasdair’s household: education at Charing Cross school, being auctioned twice, journeying across the country dressed as a man. She felt sure that there would be more exciting adventures to come.