Tim Ch. 02

Tim, relieved, reached for his knickers but Christin had other ideas. "No you don't Tim. I will need your bottom again before we are through." Tim saw one of the shop assistants coming over, he was worried that he was about to be bollocked as although whores were encouraged to dress provocatively they were not meant to be naked in public. It was always the whore rather than the client who was told off. The shirt's tails only just about covered his modesty. In the end the assistant only wanted to make a few ingratiating comments to Christin.

They came to the dildo section, a selection were on display in sterilising solution. Christin pickled up a huge vibrator. "Tim, spread your legs." Tim did as he was told he could not believe Christin was going to fuck him in public. He felt the slight sting as the sterilising liquid was wiped along his arse. He felt more pressure as Christin pushed. Tim tried to relax, but he knew this was going to be difficult. Christin eventually inserted the dildo and gave Tim a few hard pumps. The performance had again attracted an audience.

"So Tim what do you think?"

In truth Tim didn't have much of an opinion, one dildo was pretty much like any other to him but he wanted his humiliation to stop, "It's great Miss. I think you ought to buy it." Christin did not fall for this and tried two more dildos in Tim before deciding on a large red gel version as it would match Tim's knickers (when of course she allowed him to put them back on).

When it came to gags Christin asked for the assistant's help. The shop assistant asked Christin, "Well Miss, do you want the gag for decorative purposes, to keep your whore silent or to cause maximum discomfort?"

"Well, I hadn't really thought. I suppose to keep him silent."

The assistant showed Christin various models explaining that nothing very new had come onto the market recently. She then pointed to a ball gag with a silver rubber ball which she said was quite fashionable.

The assistant picked out a black gag in the shape of a large penis, "This is great for punishing slaves, it also improves a slave's ability to give blow jobs as they get used to taking the penis all the way down their throat." Christin picked up the gag, trying to hide her surprise at the size of the penis, could Tim really take this down his throat? There was only one way to find out. She gingerly eased it into Tim's mouth and eventually got it all the way down; the poor boy looked in great discomfort. Christin buckled the gag securely in place.

The assistant recommended the matching butt plug, "It's big but your slut looks as if he can take it. It's a really nice set and being penetrated by two cocks at once can really humiliate a boy." Christin liked the idea and told the assistant to try it out on Tim. Tim was prepared and now used to being fucked but the plug was huge. He stripped off his shirt and tie and bent over, trying to relax. The assistant lubed the plug and Tim's rectum with practiced skill, but they both knew it was not going to be easy to insert something this large. The size of the plug and Tim's efforts to take it increased the size of the crowd. He strained, pulling his buttocks as wide as he could, gyrating his hips to ease the entry of the monster. The assistant was putting huge pressure into forcing the plug in and out, trying to push it deeper with every stroke. It was hard work, but she could see it was worse for Tim, who was sweating profusely and in obvious distress, made worse by the gag. When eventually it was in place Tim was hugely relieved and almost insensible to an enthusiastic round of applause. On the end of the plug was a cute little bunny's tail, it made Tim's adorable arse look so sweet. Christin loved the set and bought it without any hesitation.

Christin made Tim keep the plug and gag in for the rest of her visit to the shop. She gazed at Tim walking naked around the shop; she almost felt sorry for inflicting such pain and humiliation on the poor boy, but watching him turned her on terribly. She just loved torturing him, but seeing so many people staring at his nudity eventually she allowed her 'little bunny' to put some backless knickers on. His tail was still on display and his arse look beautiful.

Tim had noted that it had become increasingly fashionable for guests to keep their whores on a chain attached to a collar. Christin had also noticed this and her eyes lit up when she saw the collars on display. She had Tim model dozens before she chose a plain stainless steel collar. She decided that she would have, "The property of Christin von Eberstein" engraved on it.

There was some embarrassment when Christin came to pay for her purchases as she could not remember the size of the butt plug. She had her 'little bunny' bend over, spread his legs and his clasp his buttocks so the shop assistant could read the bar code on the end of the plug. When this was sorted Christin allowed Tim to put his uniform back on and remove the gag. They then left casually chatting.

Christin sent Tim to one of the school rooms whilst she returned to her room to change. Tim took the opportunity to remove the butt plug, he felt a huge sense of relief. Christin returned dressed as a 'teacher', this involved a white satin shirt and a latex micro skirt. She looked fantastic, the get up showing off her figure and particularly her long legs to their best advantage. Tim thought back and admitted he could not remember that number of his teachers wearing such a skirt but it was not his place to comment.

Christin sat down in one of the easy chairs and looked at Tim with a severe expression, "Come on my little bunny, strip down to your collar and panties."

Tim did as he was told, slowly removing his tie, shirt and shorts. Christin said nothing, just staring at him. Tim hated people watching him undress and Christin's insistence that he keep his knickers on was almost worse that stripping naked. She had clearly chosen them to humiliate him, they were very brief, being made of red satin with edgings of black lace.

"Bend over the desk." Tim did so, tensing his buttocks and legs to show himself off to the best advantage. Christin approached and stroked the tight satin, her hand then wandered between Tim's legs massaging his cock. She did this with a certain languor.

Christin loved seeing Tim bent over like this, the red satin of his panties stretched taught against his buttocks, it gave her such a sense of power. The feeling almost sent an electric shock to her pussy; every step seemed add to her desire as her pussy rubbed against the latex of her skirt. She was feeling so incredibly horny.

Christin picked up the riding crop and started to whip Tim, softly to begin with but with gradually increasing force. Although Tim tried to stay silent, he let out involuntary yelps whenever Christin struck a hard blow.

"Bunny, take down your panties, I want to see my handiwork." Tim slipped down his knickers revealing his buttocks criss-crossed with vivid red stripes. Christin continued to beat the now naked Tim. His cries of pain were so erotic. But despite the punishment he stayed leaning over the desk, just for her entertainment. Christin admired her boy, he was so damned beautiful and he was hers, she had to have him. Christin motioned Tim to her bed and got him to lie down.

"Now let's have some fun."

Christin struggled out of her latex skirt and then whipped off her panties. She tied her shirt under her tits and stood in front of Tim to let him admire her. Admire her Tim certainly did, she looked magnificent just dressed in her stockings and shirt, her midriff and partially shaved pussy on show. She had a great body and knew it. Tim was rapidly becoming excited.

Christin crawled onto the bed. Tim knew a good prostitute always responded to their client's mood, after such a whipping Tim was expecting Christin to want some pretty rough sex. But he was surprised, Christin held him firmly but then kissed him incredibly gently, initially her lips barely brushed his. Tim therefore was careful when he penetrated her, so as to be as gentle as he could. His thrusts were slow and careful. Christin responded, gradually upping the tempo, increasing the pace. Soon he was fucking her with an animal passion. As she reached climax she screamed with pleasure. She had fucked her slave and it had been wonderful.

Tim felt Christin's head resting on his shoulder as she dozed in a blissful sleep. When she awoke the intoxicating smell of cum aroused her anew. She gave a Tim a gentle blow job, not really to excite him more to taste his cum. She then released him and had him take her in the doggy position. This time Alex clutched her tightly in his arms as they both dozed. Eventually it came time for Tim to leave, he dressed in his uniform and gave the still sleepy Christin a gentle kiss goodbye.

As he left, he kicked himself remembering the Escorts' rule number one, never fall in love with your client. He knew this but he did so hope that Christin would choose him again. ~

As Tim returned, tired, to his room he was called by one of the 'teachers'. These were customers who had paid for the privilege of 'disciplining' any boy or girl they desired.

"You, come here."

Tim approached as he was bidden, "Yes, Miss."

"Bend over."

Tim knew the score, he squeezed out of his shorts and let them fall to the ground. He then did the same to his knickers and bent over, legs straight, hands on his knees and awaited the inevitable. He felt the breeze on his exposed cock and buttocks. His nakedness was attracting an audience.

The 'teacher' smiled, gently raised Tim's shirt and proceeded to whip his bare bottom with a riding crop six times. After his punishment Tim pulled up his knickers and shorts and said "Thank you, Miss." He knew one session was not too bad but he hoped not to get caught too often.

Jessica was thinking the same thing. She had been caught four times in the last half hour and her bottom was now a very rosy shade of red. It was painful even for a reasonably experienced submissive such as herself. She couldn't keep on getting spanked, the best way of avoiding such regular punishment was to get a half or whole-day date. A date may involve some pain but this was likely to involve one session and be relatively short and sharp.

Management always ensured that there were far more whores on duty than there were guests, this ensured that there was always great competition between the whores. Jessica wondered about how best to get the date she desired. She knew she could always sell herself at the 6 o'clock auction, the difficulty there was that if enough customers did not turn up she might find herself going for 99c. She thought about sitting on the low wall just outside the entrance to the dormitories. When she got there she saw that six girls were already sitting on the wall including one painfully gorgeous grade one. She thought of joining them, but worried the area might be on one of the teachers' beats. Jessica therefore decided to head for the communal showers. The idea was that girls and boys showered there after playing games, but Jessica knew no one would mind her having an extra shower. She stripped and put on her collar so clients would know she was available and her grade.

Jessica stood under the powerful cascade of water luxuriating in the massage this gave her. The shower seemed to reduce the pain of the spankings and she quickly forgot the reason for originally coming there and started to enjoy herself. She was brought back to the present when she feel a hand gently to massaging her bottom. She began to turn, she knew the next few seconds were important. She wanted to 'land this date', in particular she hoped it was not some opportunistic whore or a time waster client. She smiled her most alluring smile and saw her admirer was certainly a client, he looked the CEO type, averagely handsome but well put together with obvious charisma.

Jessica pressed her body lightly against his. He did not pull away so she pressed her pussy against his thigh, knowing he would feel her warmth. He did not say anything, he merely took her hand and steered her out of the shower. She dried herself, put on her shirt and tie and without knickers or skirt started on her hair and make up. When she saw he was ready she wandered over and finished dressing.

"Hi, I'm Simon. Would you be able to keep me company for the next twenty four hours?"

Jessica's heart jumped, this is exactly what she was hoping for, "Yes sir, that would give me great pleasure. My name is Jessica."

"OK, Jessica take your knickers off. You won't need them for a while."

Jessica quickly took off her panties and handed them over. It was odd, she was so used to being naked in front of customers but walking around without knickers still felt very unnatural and rather decedent. More so because she was so perfectly shaved, she felt cold. As her skirt was so short she suspected her nakedness was not a total secret to those she and Simon passed on the way to the hotel complex. Perhaps Simon was thinking along the same lines and to ensure there was no uncertainty he got Jessica to bend over to pick things up at regular intervals exposing her ever so bare bottom.

On entering his room, Simon immediately told Jessica to open her mouth and pushed her panties in. He sat down and told Jessica to lie on his lap. Simon started by raising her skirt and stroking her beautiful behind, but before long began to spank her. The strokes were getting quicker and harder as Simon got increasingly excited. Being spanked was an inevitable part of being a school girl, but Jessica was in real pain. She screamed but with panties firmly wedged in her mouth only the quietest mumble could be heard, not that Simon was interested he was in "the zone".

Eventually Simon seemed to get tired and he first slowed then stopped. He then slipped his hand between her legs and started to stroke her pussy. Jessica's body was in overload, first pain now pleasure. She squirmed as his rubbed her clitoris. He then forced his fingers into her pussy entering her with increasing force. Jessica gasped, her pain forgotten, she was now wild with desire.

"OK, Jessica, put on these wrist and ankle cuffs and sit on the bed."

Jessica did as she was told, feeling renewed pain as she sat down. She pulled up her skirt, spread her legs as far as she could and awaited Simon's pleasure. Simon clipped her wrists to a hook above her head and her ankles to the bed board about three feet apart. Jessica was now firmly secured, legs spread and pussy totally exposed and defenceless. Simon surveyed his handiwork then stripped and quickly entered her with the barest minimum of preparation. The fucking was brutal, this was basic and animal sex, no love or gentleness Simon thrust with ever increasing force. Eventually he came with a shout of ecstasy. After his climax Simon slept, leaving Jessica secured, cum all over her.

Jessica was still in her, now ragged and stained, uniform; her was makeup smudged with streaks of sweat, she looked a sight. On waking Simon told Jessica to get some clean stockings, suspenders and panties as they were going to dinner. Simon dressed in an immaculate dinner jacket and waited as Jessica did her make up, she put on her underwear and entered the main bedroom. She hoped Simon would let her wear her evening dress or even her uniform, but she was disappointed.

"Good, Jessica you look wonderful. Let's go."

Simon escorted her down to the lifts. Jessica tried to look relaxed as she walked down the corridor. She was proud of her body, in particular her pert tits, but still felt very naked seeing couples in their elegant evening dress. When they arrived at the lifts they met a lady who seemed fascinated by Jessica's breasts and with Simon's permission stroked and squeezed Jessica's nipples. She then asked Simon about Jessica's sexual prowess as if Jessica wasn't there. Jessica was very conscious that the livid red stripes on her bottom were very visible; the brief satin panties giving almost no protection. Simon made her bend over and take down her knickers so the lady could examine her bottom in intimate detail.

On arriving on the third floor Jessica tried to quickly pull up her panties. The lady went to the right and Simon guided Jessica to the left. They headed for the 'Graziani's'. As they entered Jessica saw a discreet sign 'All patrons are respectfully asked to wear knickers at all times', as Jessica looked around she saw this was about all many of her fellow whores had on.

They were steered to a table in the centre of the room. After Simon's rather brutal treatment of her so far, Jessica was surprised to find he was a delightful dinner companion. She very much enjoyed his light self depreciating wit and laughed, totally forgetting that she was topless and had an aching bottom. After the second cognac Simon said they had better be going.

One of the main attractions of the weekend was the dormitory block. This was a specifically designed building that consisted of four dormitories, one all male, one all female and two mixed, each having about thirty beds. Every dormitory had a wash block attached, in the centre of which was a block of basins, on the right shower cubicles and on the left a communal shower area. Whores were, of course, obliged to wash in the latter.

Simon had booked two beds for the night. Jessica found her single bed and stripped, she then went to the shower and washed carefully making sure Simon had a good view. Returning to her bed she dressed in the standard night shirt. This was pale pink satin for girls and pale blue for boys. It had was short coming down to mid thigh, had long sleeves buttoned at the wrists and was buttoned at the neck with a small delicate collar. Looking in the mirror she knew she looked terribly innocent and vulnerable. Even she could admit that the innocent bit was not a real reflection on her moral character. When she had dressed she joined her fellow whores doing the sort of thing school girls did before bed. She shaved her bikini area, lubed herself then read a romantic novel.

The lights flashed on and off indicating 'lights out' would be in five minutes. Jessica looked at her bedside table, with the normal schoolgirl accoutrements; alarm clock, teddy bear and ... a dozen condoms, lube and a twelve inch gel vibrator.

Jessica's mind wandered and she thought back to her time in Diston, how a week after her eighteenth birthday she approached the local brothel asking for a job. Mrs P took her on a probationary basis telling her she should, "Be attentive, willing, available and fuck like a bunny." When the lights went out Jessica got out of bed, she pulled her nightshirt up to her neck and spread her legs. Jessica then gave her clit a good rub. She felt ready. She thought Mrs P would concede she looked pretty 'willing and available'.

Simon told her to kneel on all fours on her bed. Jessica did as she was told, spreading her legs as far as she could. This time Simon was more gentle as he took her anally. After Simon had climaxed, he dismissed Jessica. As she got into her bed she felt tired, she felt she had well and truly earned her money that day and had a very sore bottom to prove it. There were still a number of couples hard at their stuff, a tired Jessica went to sleep with her teddy bear to the cries of ecstasy as her colleagues worked into the night.

Jessica woke the next morning to her neighbour's sighing. Sex at seven am! Jessica got up and got a cup of coffee for Simon. She sat on his bed as he drank it, offering herself to him. Simon thanked her but explained he had to leave on the first flight so declined.

Jessica went back to her room. She felt she could relax for a couple hours and then try to get another date before lunch.