New Client
After the ‘Emma’ incident and the successful WMP party Marie-Becky came to trust Jack and promoted him to a ‘Grade two’ whore. She felt the fact that Jack had not betrayed her when he had the chance meant that he could be trusted to go on ‘out-call’ jobs. Jack’s first job was to serve a Mrs Margaret, he was to go to the ‘super luxury’ Bristol Hotel in Mannheim. He was told that Mrs Margaret was an important industrialist, managing her late husband’s diversified business empire.
At the hotel the Assistant Manager Heidi Klaus swore (she knew obscenities in six languages) “Where is the bloody prostitute?” Heidi was used to providing guests with ‘companions’ but she hated the fact that these people were not under her direct control. Most of the whores were sourced from two main agencies in Mannheim, the Bristol only used Cartwright and Palmer when their client wanted something more unusual. Heidi was rushing around organizing the final arrangements for Mrs Margaret’s stay; white lilies in the room, Pol Roger champagne in the fridge, Camus cognac and Talisker whisky on the sideboard the list was endless, but the Bristol prided itself on getting the details right.
When Jack got to the lobby he called her mobile “Hi, it’s Jack from Cartwright and Palmer, I was told to report to you.”
“You are late, get the receptionist to point you to Suite 711.” With that Heidi terminated the call.
Jack was shown into a huge very modern huge suite, with stainless steel, glass and black leather being the prevalent materials. He was standing in the reception room which contained a huge TV, a couple of sofas and a meeting/dining table. An attractive woman marched in, age wise probably 35-45, her hair tied back and wearing a navy blue business suit with a white silk shirt. She barked, “Are you Jack?”
“Yes, ma’am.”
“I am Heidi Klaus, the Assistant Manager of this hotel and the person responsible for Mrs Margaret’s stay. I believe you are a prostitute who specializes in submissive services, is that correct?”
“Yes, ma’am.”
“Good, I can’t say I like providing people like you to our guests but as Mrs Margaret made the request it is my responsibility to satisfy it. Now strip.”
Jack was surprised by the order but knew it was pointless to argue so he did as requested. He stood in some black high cut knickers in front of Heidi, who circled around him looking him up and down. He wondered if she really needed to see him like this or if this was (an effective) way of humiliating him and emphasising her superiority. She twanged Jack’s tight knicker elastic, smiling as he winced.
He seemed to pass the muster as she said, “Your official title will be ‘Research Assistant’. Now listen carefully we have some rules all prostitutes must obey at the Bristol; one, no soliciting of other guests, two no wearing of provocative clothing in the public areas of the hotel, three, you may not go to the bar or restaurant unless accompanied by one of our guests and four, you will leave the hotel no later than our guest. I will take great pleasure in having you thrown out of the hotel if you disobey any of these rules. Got that?”
“Yes, ma’am. I understand.”
Looking at her clip board, Heidi said, “You were asked to bring a dinner jacket, a business suit, swimwear, restraints, a dildo, nipple clamps, condoms and a selection of canes and paddles, do you have all these?”
“Yes, ma’am.”
“Good, Mrs Margaret will be here in twenty minutes. You had better get dressed. I believe you have a waiter’s uniform, put it on and be standing by the entrance at 5.50pm. Any questions?”
“No, ma’am.”
Jack unpacked his stuff and dressed in his uniform, which consisted of a white satin military-cut jacket and some tight skimpy white satin shorts, and was waiting by the door with time to spare. Mrs Margaret came into the room accompanied by two bellhops carrying her cases. She was in her late fifties or perhaps early sixties very elegant and simply reeked of power and authority. When she had dismissed the porters she looked at Jack.
“So you are my companion for the next couple of days.”
“Yes, ma’am. Cartwright and Palmer sent me.”
“Good, I know the agency. I will be stressed and busy so will need my relaxation, you had better be good at your job. Did you bring all the things I requested?”
“Yes, ma’am.”
“Here is a ‘bleeper’ you are to carry it at all times, if it goes off you are to come to me at once.”
“Come here and take your clothes off, I want to see what I have bought.” Jack did as he was told, “Spread your legs.” Mrs Margaret circled him and started by caressing Jack’s bottom, then gently stroked his penis without making any comment as if Jack was some inanimate merchandise. Jack did not know if he had met with her approval or not.
“Kneel.” Jack did as he was told and Mrs Margaret put an inch wide metal collar engraved ‘Sex Slave’ around his neck, the collar clicking firmly in place. “You will wear it for the rest of your stay, waking and sleeping. It is loose enough to be invisible when worn with a formal shirt, but it signifies I own you body and soul, so don’t forget it. Now put the uniform back on, you have some work to do.”
~
Mrs Margaret got Jack to unpack her bags and run a bath whilst she relaxed with a book. He was then sent to shower and to change into a dinner jacket. Before he got into the shower, Jack tried to remove the collar but found it was securely locked. He realized he would not be using the hotel’s swimming pool! Jack then escorted Mrs Margaret to dinner at the Bristol’s restaurant. This was the ideal for an escort, good food, good wine, an interesting client and some mild flirting. After dinner Mrs Margaret suggested a night club. They went to “The Hervey” situated a few blocks away. The management clearly knew Mrs Margaret and they were escorted to a small table in a discreet corner.
After a few minutes a waitress came over to ask if they would like to order any drinks. Mrs Margaret studied the wine list, Jack studied the waitress. She was a tall, athletic looking blond dressed in a white satin shirt and black satin skirt. The white shirt was tight and the girl had undone most of the buttons, so her cleavage was staining the remaining fabric. Her skirt was similarly skimpy just about covering her perfect behind.
Mrs Margaret ordered a claret and asked the waitress “Are you available later?”
“Yes ma’am, I am on waitress duty until 10 o’clock and then can be booked, see ‘the system’ for details.” The girl then leant over Jack exposing her thong covered arse and pressed a button in the centre of the table. Immediately an iPad type device came to life. Jack saw there were various tabs ‘Boys, Girls and Rooms’. The waitress clicked to the ‘Girls’ tab and said, “I am Ashley,” clicking on her own icon. Up came a web page that had a rather fetching picture of ‘Ashley’ in the nude and told them ‘Ashley is everything you could want in a young woman and more... Warm, sensual with a naughty erotic side it does not take her very long to reveal! She offers the perfect company at any time of the day...’, then followed a list of all the sexual activities that Ashley ‘enjoyed’. At the bottom of the page were the girl’s rates and a booking system. Ashley curtsied and left.
Jack could not help looking at her as she left, or more accurately her behind which was only partially covered by her skirt. As he looked two lithe young girls walked over to the next booth. They were dressed in elegant figure-hugging evening dresses. They stopped in font of the table and asked “Did you order Joanne and Poppy?” Jack did not hear the answer but he saw the girls touch two clips at the top of their dresses and saw how their outfits fell to the ground leaving them standing naked in front of their prospective client. They stood like this for a couple of minutes making no attempt to cover themselves, as if it were totally normal for them to be standing nude in the middle of a restaurant. They then turned so the man could see their perfect bottoms. Eventually they were told to put their dresses back on, this they did and sat next to their new client.
Jack continued to entertain Mrs Margaret, as they drank their excellent claret. After about an hour a waiter came up to Mrs Margaret and whispered something in her ear, she nodded. The waiter than asked Jack to accompany him, Mrs Margaret indicated that he should do as he was asked.
Jack was escorted to a side office. He knocked on the door and when he entered he saw a bored looking woman sitting at a desk in front of a line of lockers. When she saw Jack she said, “You’re with Mrs Margaret? Please take all your clothes off and put them in locker 15, I will get the kit you will need.”
Jack looked around and found there were no changing rooms so reluctantly undressed in the middle of the office. When he was down to his briefs he turned to the lady to find what clothes he should be putting on. She made it plain that Jack should strip completely, this he unwillingly did, hoping she would provide something decent in return. He stood naked in front of her desk whilst she looked him up and down before she gave him a black satin toga. He put it on noticing, as he had feared, that it barely covered his bottom.
Ashley then walked in. She looked surprised to see Jack “Oh hello, I thought you were a client.”
“No I am Mrs Margaret’s companion. I am called Jack.”
“Then it looks as if we will be working together.” As she was talking she stripped off her clothes and asked the lady for her toga. Jack could not stop himself staring, Ashley’s body was superb, smooth and athletic. When she put the toga on, she checked herself in the mirror. Jack could have told her she looked perfect, but he was not asked.
“Has anyone explained how these things work?”
“No.”
“Well you see these clips on the shoulders, when we are presented we pinch them and the toga will fall to the ground. There are weights in the seams to make sure the toga falls smoothly, like this.” Ashley unclipped her toga and sure enough it fell displaying her naked body, “Try it.”
Jack pinched the clips and after a few goes the toga fell as it was designed to.
Ashley looked at a screen set into one of the walls, “You have got Dungeon 15, I’ve got 17. If we have time I will show you around. They are well equipped, you will probably know the set up, normal torture instruments, a bed and I think yours has a Jacuzzi. Are you a professional?”
“Yes, I have been doing this for almost a year.”
“Great, I hate working with newbies. We now just hang around until we get a call.”
Ashley showed Jack around his dungeon as promised and after waiting for about half an hour they got the call and were told to present themselves at Mrs Margaret’s table. Jack saw that Mrs Margaret was talking to an older man and a young, slightly plump, woman. As they approached the table Mrs Margaret saw them and said “Ah, Erik, Peppa, your prizes have arrived.”
Ashley whispered, “Now.” Simultaneously they reached for the clips on their togas, and watched as they fell to the ground. As Ashley and Jack stood naked in front of the table Mrs Margaret continued, “Erik I hope I was right in getting you a girl and Peppa you a boy, we can change things if you want.”
“No thank you, Mrs Margaret.” They responded in unison, as Ashley and Jack turned to show them their behinds.
“OK, take your prizes and have fun, you have deserved it.” With that she waved her employees away.
Ashley and Jack pulled up their togas and led their clients to a door marked with a skull and cross bones.
When they entered Dungeon 15, Jack showed Peppa around and then got down on his knees in the middle of the dungeon. The lights were low and the room smelt of leather and sex. Peppa looked at Jack, staring at his ‘Sex Slave’ collar, and said, “Let’s start as we mean to go on, lick my shoes.” Jack did as he was told, Peppa looked on as Jack’s toga slipped to one side revealing his naked bottom squirming around as he licked each side of her shoes.
“Jack, I have looked forward to this for a long time, I have heard my male colleagues talk about giving the girl a quick spank and then having sex, your punishment will be lot more painful!” Peppa hoped she had said this with confidence. She had always yearned to torture someone and was worried that Jack would stand up and explain that he could only be spanked a few times and the torture equipment was only for show. Who would voluntarily submit to what she had in mind? Peppa decided the thing to do was to start the session slowly and gradually increase the level of pain and humiliation, hoping that Jack would not object. She knew that if he complained she would have to accept things and stop.
She removed her business suit and stood before Jack in a black leather corset, brief panties and suspenders. “Jack take off the toga, I want you to wear this.” Jack let the toga fall to the ground and took a gauze mini-skirt from Peppa. He pulled the skirt on, easing the elastic over his hips. He was not happy, this was so embarrassing. He was not surprised the skirt was short, but at least it seemed the gauze was just about thick enough to give him some cover.
Peppa thought Jack looked strikingly seductive in the skirt, his shaved androgynous body made him look sexy and terribly available. He seemed very natural, he did not look as if he was trying to dress as a woman, merely as if he were wearing some very revealing underwear.
“I was going to dress you in shorts, but then I thought I might need to punish you and a skirt would be so much more convenient for both of us. I hope you agree.”
“Yes, mistress.” Jack lied.
“As you are wearing a skirt you will curtsey to me after I give you an order.”
Jack flexed his knees as he said, “Yes, mistress.”
Peppa walked behind Jack and the lifted the back of his skirt to give his bottom a stroke. She then caressed his arse with a feather rubbing it between his legs touching his cock. “Spread your legs, Jack.” Peppa continued to massage Jack’s inner thighs with the feather. To Jack it was torture, oh so very pleasurable torture, but he knew he had to stand as still as he could. As the feather caressed his penis it felt as he was on fire, he was painfully aroused. Peppa came around to face Jack. She brought her face within inches of Jack’s, letting her scent waft over him. She really was very sexy Jack thought, he yearned to take her head in his hands and taste her glistening lips. She started by caressing his nipples, then raised the skirt and began to stroke his balls again. Jack tried to look away and think about other things as Peppa concentrated on stroking the underside of his penis and his balls. She dropped the feather and grabbed Jack by the thighs and pulled him against her, his erect penis wedged against her panties, it felt wonderful. After what seemed like an age, Peppa let go.
“So Jack did you enjoy that?”
“Yes, mistress.”
“See, I said you would see the advantages of wearing the skirt.”
“Yes, mistress.”
Mrs Margaret watched Peppa and Jack and Ashley and Erik on the Hervey’s CCTV. She looked admiringly at Ashley’s body but quickly got bored, Erik only wanted vanilla sex, Mrs Margaret always knew he was tedious. Ashley was very good at her job and Mrs Margaret knew Erik would be boasting about this night to his dull friends for months to come. Peppa on the other hand was fun, she was a kinky young lady and looked good in her corset. Mrs Margaret was impressed how she had planned ahead; the skirt was a nice touch, she could see Jack was very uncomfortable wearing it. Mrs Margaret laughed as Peppa forced Jack to curtsey, perhaps she should get Jack to do this for the rest of his time with her.
Peppa kept Jack standing in the centre of the dungeon and now reached for a riding crop. She circled around Jack gently raised the back of his skirt. She eased the crop between Jack’s legs gently easing them further apart, and then massaged his bottom with the crop, all this in silence. After raising the front of the skirt she tapped his inner thighs and stroked his balls with the crop. Then Peppa started tapping Jack’s cock. The rapid blows were not hard but their cumulative effect were very uncomfortable for Jack. Peppa loved the sound of the crop on Jack’s penis.
“Now Jack, bend over the whipping horse.”
As Jack went to the horse he heard Peppa say, “Come back here Jack, remember you curtsey when you receive an order.” Jack apologised, returned and stood before his mistress, smoothed down his skirt and gave her a deep curtsey. Peppa thought he looked terribly vulnerable, this just added to her desire.
Jack leaned over the whipping horse and Peppa buckled the wrist cuffs onto him. Peppa stood back and gazed at the lovely sight of Jack strapped to the horse, his skirt barely covering his delectable bottom. She had fantasised about this for so long and finally, incredibly her dreams were coming true. She was so turned on she was almost incoherent and couldn’t resist rubbing her pussy. She felt she might explode and there was still so much fun to be had. It just got better, she had worried that Jack might refuse to wear the skirt, then he might refuse to curtsey and finally she wondered if hitting his cock with the crop was beyond his limits, but he had obeyed her. She could see he hated some of this, especially being forced to wear a skirt, but the important thing was he was submitting.
Peppa folded Jack’s skirt into the waistband so she had an uninterrupted view of his behind. She then arranged a selection of the whips she was going to use on a side table.
Peppa started with the feather again, but this was to lull Jack into a false sense of security. After a few minutes she silently dropped the feather and picked a cane and gave Jack three quick firm blows. Jack was shocked out of his pleasurable daze. There was nothing quite like the searing sting of the cane. Jack yelped, he vividly felt the three strokes and the pain did not diminish. Peppa then started to use the paddle. She loved the sound that the paddle made and knew the pain was less intense than the cane but spread over the whole of Jack’s arse.
Peppa realized that as Jack was not complaining about his beating, she could do pretty much anything she liked with his body and she should stop worrying about being told to ‘stop’, the only limit was her imagination. She enjoyed her ‘work’, but she found her panties were getting somewhat moist and restricting her movements so dispensed with them. She felt so liberated, and rather naughty, walking around the dungeon in just her corset and stockings.
The riding crop was Peppa’s favorite, she thought it was so elegant and loved the accuracy with which she could target her whipping. Peppa had concentrated on Jack’s buttocks and was rewarded with a beautiful red glow as evidence of her hard work. She now aimed for Jack’s thighs, particularly the soft inner thigh, she loved to see him ‘dance’ as she rained the blows down. A particularly hard whack from Peppa’s crop resulted in Jack letting out an involuntary cry of pain.
After the last yelp, Peppa thought she should quieten Jack down a little and went to look at the gags. She chose a ball gag and was walking back to the whipping horse when she saw her knickers lying on the ground. This gave her an evil idea, she ordered Jack to open his mouth and instead of the gag pushed her panties in. She wondered how they tasted! She sealed his mouth with some black duct tape.
Peppa stroked Jack’s bottom, feeling the heat and marvelling at its redness, crisscrossed by a few darker cane marks. Peppa released Jack and took him over to a large PVC table, she told him to lay on his back and bound him spread eagled. Peppa pulled the restraints on Jack’s legs very tight so they were spread exceedingly wide and he could not move them at all. This left his cock very exposed. Peppa felt the inside of his thighs, stroking his soft sensitive skin, then felt his penis, which she massaged with a slow rhythmic motion. She was pleased that Jack became hard very quickly. He was truly at her mercy. She slapped his penis and smiled as it returned to the vertical position. Jack did not smile, he felt as if his legs were being wrenched apart.
