Old 11-02-2014, 03:36 PM   #16
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Chapter 9


"Laura?" Kate said holding up the first note that was inside the box.
  "Here!" The girl who sat next to Ruby said and stood up and got the note from Kate. She was a tall and skinny girl, she had dark hair that hung loosely down to her shoulders and was wearing a pair of glasses.
  "You will find the wardrobe in the door on the opposite side of the hall from this room, open your note there and you will figure out the rest, the room number you have to go to after is written in the note in your hand. We have all of this floor to our disposal so you will find your designated rooms by walking through the hallway."
  Laura left the room with her note and Kate picked up the next one from the box.
  "Ruby." Kate said looking at her.
  Ruby stood up and walked over to Kate to get her note. As she received it Kate wished her good luck in a whisper and then she walked out the door to find the wardrobe.
  
The wardrobe was a small room with a few benches and lockers on each side, it also had a secondary area with showers, which Laura was apparently using.
  "Laura?" Ruby asked as she sat down at a bench.
  "Yes?" Laura replied back from the shower room.
  "Why are you in the shower now?"
  "Because my note wanted me to be freshly showered. Maybe my client is some cleanliness freak or something, i dunno."
  "Okay, i was just curious if i got the wrong room somehow, sorry."
  
Ruby opened up her own note and read it:
"Job description:
Room number: 105
Client name: Jacob
Age: 43
Client wish: The client has requested to get a full body massage.
Checklist to complete for this job is:
  • 15 Minutes lying face down, hands and feet tied up.
  • End with a happy ending (Hand job) after the 15 minute timer.
  • Remember to use massage oil.
  • The client will continually request which area to work on during the massage.
  • The girl giving the massage must do it naked.
  • The client will rate the work with a 1-5 (5 is the best rating.)
- NOTE: All jobs are being recorded for safety reasons, as well as evidence keeping."

Age 43... That’s over twice my age. Ruby thought to herself staring at the note in her hand. And i’m supposed to give him a hand job aswell?!
  She took off the clothes she had on and put them in a locker where she also found a bathrobe to wear until she got to the room she had her job in.

As Ruby left the wardrobe, another girl was on her way in, she didn’t know her name but it was definitely one of the girls she recognized from the trip to the prison, mostly due to her long red hair.
  102... 103... 104... 105. She stopped outside the room to quickly read her note again. Naked... Remember to use oil, 15 minutes of massage with a happy ending to finish it off... The thought of it creeped her out, for all she knew it could be her dad in there.
  Ruby took a deep breath and put on a fake smile and opened the door.

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Old 11-03-2014, 06:16 AM   #17
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Chapter 10


Ruby opened the door and entered. The room was small, maybe twice the size of her cell. On the right side there was a table with different lotions and oils on it, and to the left there were towels hanging on the wall together with some clothes wich had to be the client's. In the center of the room there was a massage bench with a man on it lying face down, both his hands and feet were tied to each corner of the massage bench and he had a towel covering him from the waist down.
  Just as Ruby closed the door behind her, the man lying on the bench raised his head and looked behind him towards her. He looked quite good for his age and he didn't look 43 at all. "Hello miss." He said, giving Ruby a smile as she came a bit closer to him. "I'd shake your hand but... I'm kinda stuck." He gave off a laugh.
  "Hello." Ruby answered back in a shy voice, focusing on keeping her smile on. "Sorry if i seem nervous, it's my first day here."
  "No problem, just hang your robe up and remove my towel when you are ready to start."
  
She took a deep breath and went for it. She slipped out of the robe wich left her naked and hung it up on the wall before removing the towel covering the naked man lying on the bench. He had a slim but muscular body and Ruby surprised herself by wanting to see the rest of him.
  "Have you been here before?" She asked him while walking over to get a bottle of massage oil, the nervousness was going away, but she still had the hand job left in the back of her mind, and she was not looking forward to that part.
  He raised his head again to check her out as he gave her his answer. "I try to come here once a year, it's quite an expensive trip."
  "I see. Are you ready to start then?" Ruby asked him back, just wanting to get this over with.
  "Sure thing, just tell me once you start the timer."
  
Ruby turned the clock back to 15 so it would ring when it was done. "Okay, starting now."
"Alright, just start with my shoulders and whenever i say the next part just move on to that." He said as he put his head back in the hole in the front of the bench.
  
Ruby walked over to the front of the bench and started applying oil to her hands and his back around the shoulder area. It was a strange feeling standing there massaging this stranger while both of them were naked.
  
Every few minutes the man on the bench gave her a new area to work on, slowly working her way down his body, ending with his feet.

Then the clock rang, the 15 minutes were up.
  Ruby went over to the clock to stop the ringing before turning her attention back to him.
  "Ahhh, that was a great massage." He said looking at her after raising his head again. "Now just get some more oil with you and give me the happy ending before this relaxing feeling goes away."
  Her nerves were back now, she closed her eyes trying to calm down as she filled her hands with oil. "How do i go about doing that while you are lying face down?" She asked him while walking over to the bench again.
  "Look underneath."
  Ruby ducked down to see under the table. Not only were there a hole for the face but there was another one for his cock to go through aswell.
  "You might have to lower the massage bench to be able to lie underneath and reach up to me, so just click the down arrow that is on the right side of the bench until you find a suitable height." He paused for a second. "Then lie under me so that i can see your pussy while you finish me off."
  Ruby did as she was asked, slightly creeped out. The bench was lowered and she crept underneath and was now lying face to face with the mans fully erect cock looking straight back down at her.
  "Perfect... Didn’t know you were allowed to shave in the prison, i have to say you look really cute down there! Spread your legs please, i want to get a good view of you while you go at it." He requested as she was in position under him.
  “I don’t know if we can shave in here, i only got here yesterday.” Again Ruby did as she was told and spread her legs. Then she rubbed her hands again to spread the oil across both of them. Now the moment of truth. She reached up and took a hold of his cock and started to apply oil from her hands all over it. Ruby started stroking him slowly, hearing the squishy noises of the oil as she went up and down with her hands. Drops of oil fell down on her chest as she kept stroking him faster and faster. She felt him grow harder by the second, something she thought wasn't possible seeing how hard he had felt from the moment she started.
  She could feel his heavy breath between her legs as she lay there under him. Strangely she started to slightly enjoy it, while at the same time hating herself for it. She didn't want this, deep inside she knew she didn't. But the more she got into it, the more she wanted it to continue.
  He started to move a lot more now, the little he could move while being tied down on the bench above her. She increased the speed again, the oil kept making sounds every time she did a stroke. She felt herself getting wet, imagining this huge cock entering her slowly, her mind starting to wander off.
  Stop! She thought to herself, forcing herself to focus. She cleared her head and kept focusing on the current task. Continuing to stroke him faster and faster, his breath growing heavier by the second.
  Then he shot out a huge load that came in waves hitting her across her chest and neck, just below her face. It kept coming out as she did a few last strokes, he was shaking hard now.
  "Oh my god... That was... Amazing..." He said almost out of breath.
  "You're welcome." Ruby answered back as she crept out from under the bench. She felt the warm fluid run down her stomach as she stood up and walked over to grab a towel to wipe herself off with. “Now i just need you to rate this.”
  "A one to five rating right?" He asked back.
  "Yup."
  "I would give you the best rating just for the ending, but since you seemed so nervous for a while there, i have to give you a four out of five. Either way, i hope it's not the last time i come across you!"
  "Thanks, have a good day then, bye." Ruby said and put on her robe again and headed for the door. She clicked the button that marked that she was done and left the room.

What a crazy experience! She thought to herself heading for the wardrobe to end her work with a shower to clean herself up.

Last edited by Luffy90; 11-03-2014 at 06:24 AM.
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Old 11-05-2014, 04:29 AM   #18
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Before the chapter, i just want to thank everyone who has read and commented! I really appreciate it. It gives me a lot more motivation to keep going

Chapter 11


Back in the wardrobe she threw the bathrobe in a laundry basket and stepped in the showers, she had the entire wardrobe to herself, not knowing if anybody else had finished their work yet or not. It was nice to be able to relax alone in the shower while feeling the hot water pouring down over her, washing away the dirty feeling after her clients explosive finish.
  Ruby got back out and dressed up in her normal prison outfit again and headed back to the room they started their day in to wait for the rest.
  Once everyone gathered up and delivered their reports their day was finished and were sent back to their cells.
  
"So how was it?" Kate asked Ruby as they got back in their cell. She took a seat on Ruby's bed leaning her back to the wall opposite from where Ruby was sitting so that they could see face to face.
  "It was... Interesting..." Ruby replied back, not sure how to describe it. "So you do this everyday of the week?"
  "Pretty much, it's easy work and it's rarely the same job as the previous day. What? Did you have a hard time?"
  "Not really." Ruby started, closing her eyes while leaning her head back."I guess i just didn't expect this kind of work in a prison."
  "Well as i said in the briefing this morning, other jobs can be... More demanding. So when i got the chance to become the leader for this job i took it happily."
  "Would it be..." Ruby pulled her knees up to her chest and wrapped her arms around them before continuing. "Would it be wrong of me to say i kinda enjoyed it?"
  “You have a cute face when your acting all shy, did you know that?” Kate just gave her a smile back and let out a laugh.
  "What?" Ruby seemed surprised by the response.
  "Nothing. It's just, you had the same reaction i had after starting this and to answer your question. No. It's not wrong. I'd say it's a good thing, it will make it easier being here."
  "So i guess the tournament you mentioned is like this?"
  "Worse." Kate responded quickly.
  "Worse how?"
  "Sorry, i shouldn't have said anything, i'm not supposed to tell you before you have actually signed up. But i'm just gonna say this. I'd rather take the rest of my sentence doing the work i do now rather than risking it and adding more to my sentence. I promise i'll explain more once you sign up for it if you still want to." Kate stood up from Ruby's bed and started climbing up to her own.
  "I do want to... I am going to enter the tournament." Ruby said just as Kate got back up in her own bed.
  "Okay, i promise i'll help you the best i can then once i can tell you more, but at least think about it again after your first week is over on Friday, just promise me that."
  
How bad can it be? Ruby tried to think about it some more until sleep finally caught up. The first day was finally over.
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Old 11-06-2014, 02:41 PM   #19
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Chapter 12


Tuesday morning. A new day, a new job. Ruby and Kate had been to breakfast and afterwards, Kate left to do her thing while Ruby waited at her cell for her new boss for the day.

After a few minutes of waiting, a new girl she hadn't seen before came up to her. She was quite a bit taller than Ruby and had long dark hair hanging loosely behind her back. She had a fairly slim body, but her boobs caught Ruby's attention. She thought Kate had a large enough pair of boobs, but this girl had at least twice the size of Kate's, tightly pushed inside the t-shirt making it sit higher on her body so that the bottom of the shirt reached up to her stomach revealing her panties aswell.
  "Ruby?" She asked.
  "Uh...Yes?" Ruby answered, quickly focusing her eyes to meet this new girls eyes.
  "Hi, i'm Caitlyn. Nice to meet you." They shook hands before she told Ruby to follow her.
  
The new group entered the same building as yesterday, but this time they entered a room in the first floor that looked like a small auditorium. It had around 8 rows of seats and in the front was a stage with a curtain covering it up. They went to the front of the room and Caitlyn told them to find seats so she could tell them what they were doing today.

"Welcome everyone. In this job we are... Models, i guess would be the best word for it. It is quite simple. We go backstage to the locker room and undress. Then we walk up on stage and the clients sitting there will request one of you for a one on one meeting for around fifteen to thirty minutes backstage in the private rooms. There are enough rooms and enough clients for all of you. Once you are done, meet back in the locker room and then we all go back out to see if there is more clients. When it is empty, we gather back in the locker room one final time and we get to read our report cards they fill out on us." Caitlyn paused a second before continuing. "Once in the private rooms, the client can give a request on what to do or they can draw a random task from the box inside the rooms. Do note that you can refuse their requests. If you do refuse their request, you draw a random task, but the tasks drawn from the box inside must be fulfilled. The clients however, can decide if they want to draw a new card, this can be done up to two times before they have to go with the third and final card. That is all. Any questions?"
  Ruby looked around to see if anyone had any questions, but no one raised their hands.
  "Alright then, follow me to the locker room and lets get this day started, the faster we do this the sooner we can end the day."
  
  Ruby and the five other girls followed Caitlyn to the locker room. Once inside they followed her lead by undressing and putting their clothes in a locker for storage. Seeing Caitlyn undressed made her boobs seem even bigger than earlier now that she had five other girls aswell to compare them to.
  
They got to the stage and Caitlyn told everyone to line up next to her, Ruby was last making her the one furthest from Caitlyn. The spotlight shone down on them making it hard to see the people in the audience.

"I want number 2 from the right." A man's voice said.

Since Ruby was the furthest to the right from the audience's perspective, she noticed the girl next to her step away and walked behind the curtain to meet her first client. She felt more nervous now that it had actually started. What would she have to do once it was her turn?

"I want the girl furthest to the left." Another man said. Making Caitlyn the one to step back behind the curtain to meet her own client.

"I want the girl furthest to the right." The next man said. Now it was Ruby's turn. Her heart started beating faster as she walked towards the curtain to meet her first and hopefully only client of the day.

Last edited by Luffy90; 11-08-2014 at 05:08 PM.
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Old 11-06-2014, 03:36 PM   #20
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Hmm what will ste have to do?
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Old 11-06-2014, 05:50 PM   #21
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interesting edition keep it going!!
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Old 11-07-2014, 05:59 PM   #22
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Chapter 13


Ruby walked past the curtain and met her client, he was a slightly chubby guy wearing a pair of shorts and a hoodie. She put on her best fake smile as she greeted him with a handshake. It was awkward standing there naked meeting this random stranger like this. Even though she had done almost the same thing yesterday with another client, this felt different. She was less in control now.
   They stepped into their room and closed the door behind them. The room was tiny, it had two small couches, one on each side of a table. On the table there was a box with lots of cards in it and a clock standing next to it.

"What's your name?" The man asked as he sat down on the left couch.
  "Ruby, and you?" She replied back, following his lead in sitting down in the opposite couch. She tried to cover herself up by putting her one leg across the other and holding the left hand across her chest to cover up her boobs.
  "Chris." He answered back and then they just sat there for a few seconds.
  "So... Do you have a request? Or do you just want to draw a card?" She asked just wanting to break the awkward silence that had arrived.
  "I... Uhh... I think i'll just draw a card. Sorry, i'm just a bit more nervous than i thought i'd be. It's my first time here." He said with a shaky voice. Ruby could see that he was almost more nervous than her as he wiped the sweat from his forehead. Everytime their eyes met, he quickly changed his stare to avoid eye contact.
  You're not the only one nervous! Ruby said to herself inside her head before drawing a random card from the box with her one free hand turning it over and reading it out loud.

"Card #93
The model will do a close up teasing dance for the client sitting in the couch. The client chooses if he wants to be naked or not."

"You ok with that card?" Ruby asked him.
  "Uhm... Can you draw another one?" He asked back.
  "Sure." Ruby pulled up the next card and read it out loud.
  
"Card #54
The client gets to ask the model 10 questions about anything he wants. While answering, the model must sit on the lap of the client facing him. The client can decide if he wants to be naked, but no sexual act can happen."

"Not that one either." He said nervously. "Please draw the last card."

Ruby was starting to wonder if he even wanted this at all. He seemed so nervous. But in the end she was happy she didn't have to sit naked on his lap for now. She picked up the last card and flipped it and read it.

"Card #60
The model will lie down on a couch blindfolded, you can find a blindfold in the drawer under the couch. The client can then do what he wants for 15 minutes, but he can not do anything sexual to the model through oral, anal or vaginal penetration. Anything else is up to the client."

Ruby was surprised by the card. It was a strange thought, not being able to see anything or have control about what was about to happen. She bent down looking under the couch and found a black blindfold in the drawer as the note said. "Are you ready then?" She asked Chris.
  He nodded back at her and she set the clock to fifteen minutes, she put the blindfold on and lied down. "Timer starts now." She said and took in a deep breath.
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Old 11-07-2014, 09:51 PM   #23
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this is a great story. keep up the goodwork.
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Old 11-08-2014, 12:16 PM   #24
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Chapter 14


Ruby was lying down on the couch, naked and blindfolded.
  Unable to see what was happening, she had to turn to sounds. It took a minute before anything started happening and she could only imagine him staring at her. She heard him kick off his shoes and then he made some other strange sounds she didn't know what was, maybe he got undressed? But she couldn't be sure.
  "Is it... Is it okay if i’m naked too?" He asked, still with the nervous voice.
  "You heard what i read from the card." Ruby started. "Anything not stated there is up to you." She decided not to say anything else after that, just waiting for the clock to ring.
  
She could hear him walking around for a bit and then she felt the extra weight of another person climb up on the couch. He had to be standing over her with one leg on each side of her stomach from the way the couch pillow moved. He kept trying to adjust his position. He then appeared to be lowering himself until he was sitting on his knees, she could feel his thighs touching her sides slightly. Then without warning, she felt his hand grab her right boob.
  He felt her up for a few seconds before he let go again. She could feel him sitting down on top of her thighs, he still had his feet on each side of her.
  Ruby felt his hand slide across her stomach, slowly moving up towards her chest. One hand reached her left boob this time and she noticed that he started moving slightly on her legs. From the way he moved, he had to be masturbating. She could feel his balls hitting her each time he did a stroke.
  He let go off her boob again and she just felt him moving around on top of her legs for a few more seconds as he kept playing with himself, then all of a sudden she felt his hand on her clit. He started rubbing it and Ruby couldn't stop herself from releasing a soft moan. She felt like moving her legs, but they were stuck underneath him, her breath grew heavier by the second. Then he stopped again.
  Both his masturbation and his rubbing of her clit had stopped. She could hear him breath heavily. He rose up from her thighs and moved forward on his knees until his knees was next to her shoulders. She could feel him right above her chest and then he started to stroke himself again. The sounds each time he did a stroke gave it away, aswell as his breathing.
  He kept going like that, slowly increasing his speed. The couch was shaking more and more and then all of a sudden he stopped again, she felt him placing his hand next to her head and then a warm liquid hit her face. A lot came out at first, hitting her directly around the mouth area with force. A few more loads came out after that hitting her hair and different parts of the face until the last drops landed on her chest as he leaned back again. He stepped down from the couch and she could hear that he had to catch his breath.
  Was it over? She thought to herself as nothing else happened. She kept her mouth shut not wanting anything to get inside of her since some of the cum was covering her lips. All of a sudden she felt his hand on her face, he took a finger and wiped the cum away from her lips.
  "Thanks." Ruby said happy she could speak again.
  Then before she could say anything else he started spreading the cum out all over the rest of her face like it was some sort of facial cream.
  What the fuck is he doing to me? She said angrily in her head. She knew he was allowed to do what he wanted, but she wasn't expecting this.
  
The clock rang, he let go of her face and she tore the blindfold off, a shocked face was left on her as she sat back up.
  "Sorry, i got a bit carried away." Chris said to her back in his shy, nervous voice again, still avoiding eye contact. He got dressed and quickly left the room.
  Ruby just sat there alone for a minute. She was still slightly surprised about what just happened, but got back out and headed towards the locker room to get herself cleaned up.

Last edited by Luffy90; 11-08-2014 at 05:11 PM. Reason: typos
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Old 11-08-2014, 12:48 PM   #25
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nice edition keep it going!!
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Old 11-08-2014, 05:36 PM   #26
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Since this chapter is fairly short, i'll just post it now instead of tomorrow. I'll still do another one tomorrow though.

Chapter 15


Ruby was the second to arrive back at the locker room. The other girl was surprised when she saw Ruby coming in with cum covering her face, she had it everywhere except from the area where she had wore the blindfold.
Ruby went over to the sink to wash herself. She kept scrubbing hard until everything was off, her face slightly red from it all. She took a final check in the mirror to make sure she got everything she could see.

Once everyone had returned they all walked back on the stage, again Ruby walked last while Caitlyn lead on in front. This time there were only two people in the audience. Hopefully she wouldn't be picked this time.

The first guy called out "I'll take the girl to the left." Making Caitlyn the first to do the second round.

The other guy took his time before requesting his own model. "I want the short girl, second from the right." The girl who was standing next to Ruby stepped out leaving the five remaining girls without any other clients left.

The girls just looked at each other, since Caitlyn was the leader, nobody knew exactly what to do.
"So... Do we just go and wait in the locker room? I think she said we would always meet there after every round." One of the girls Ruby didn't know the name of asked.
Again they exchanged looks and they agreed to leave the stage.

Back in the locker room they started to get dressed again while waiting for the two girls who had clients. Nobody said anything as they sat there, several minutes of silent waiting until this one girl broke the silence. "Do you girls want to spend the wait sharing what everyone did? I'm Jessica by the way."

Ruby was the one sitting next to Jessica and she was the first to get eye contact with her after Jessica asked the question, so she took the initiative in answering. "Sure, if everyone is up for it?"
The three remaining girls nodded in silence. Everyone seemed interested in what the others had done.
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Old 11-08-2014, 06:43 PM   #27
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You're doing really well. Keep it up.x
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Old 11-08-2014, 08:53 PM   #28
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Great story looking forward to reading more soon.
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Old 11-09-2014, 09:05 AM   #29
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Chapter 16


"I'll go first then." Jessica started. "My client first of all was this really old dude, probably in his sixties. I was slightly creeped out by that as you can probably imagine. At first he asked me to let him fuck me as his request, but in no way could i go through with that. Then the first card i drew told me to give him a blowjob for fifteen minutes and i could not stop unless he told me to. He accepted that, obviously... And down i went. It was weird sucking this guy off who was maybe three times my age and looked like he would die of a heart attack at any second. Surprisingly he held out until almost the end and he was nice enough to tell me to let go so that he could cum on my tits instead of inside my mouth. After he had came he just sat back and relaxed and let me clean myself up. So all in all i guess i was a bit lucky? What about the rest of you?" She looked at Ruby next making her the focus from the others aswell.

"Guess i'm next then." Ruby started. "Hi, i'm Ruby. My client was this shy, chubby guy who was around my age i guess? Never asked him. He seemed pretty nervous starting out. He didn't give me a request so we ended up drawing cards. Declining the first two cards, we had to go with the third one wich was me lying blindfolded on the couch, while he did what he wanted to me. He was not allowed to penetrate me in any way though so i felt relatively safe. To summarize quickly he ended up blowing his load on my face and then he...” Ruby let out a sigh before continuing. ”Then he used his hand to spread his cum across my entire face like it was some sort of facial cream, really weird. That's pretty much all that happened."
  
The other girls were silent for a few seconds before one of them took the initiative.
  "I'll go next... I'm Erin. My client was a fairly cute guy to be honest, around his early twenties i believe. His request was quite innocent so i accepted it. Not much to tell really but he just wanted me to sit there with him, both of us naked, for thirty minutes while we asked each other questions. Seems like i had the easiest one so far." She looked to the girl next to her once she finished, hinting for her to go next.
  
"Hey, i'm Allie. My client was this old guy aswell, probably in his fifties or sixties. He didn't have a request, so the card we ended up on was me having to lick cream off his body wherever he put it. It started kinda fun to be honest, but once he got confident he started doing it on his cock and even put some right on his butthole. The thought of throwing up was not far off after that, the mix between eating a lot of cream and eating an old man's butt is not something i'd put on my menu normally.
  The last line gave the group a laugh before the final girl gave her story.
  
Hi. I'm Katherine. I met this client who was maybe the same age as me. He made no request either, so we ended up with a card that told me to stand up for fifteen minutes while he could touch me however he wanted. He ended up spending most his time fondling my boobs, but he didn't leave my pussy completely out as he slid his fingers across it and gave my clit a short massage, he never stuck a finger in though. It was weird just having to stand there, but he seemed to enjoy himself so i just tried to not think about it and let the time go."
  
A few minutes later, the girl who was picked last the second round, returned and got herself dressed. There was no time however to ask her for her stories before Caitlyn came back in with everyone's report cards.
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Old 11-09-2014, 02:24 PM   #30
issabella
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good edition and i hope she got a good one but i dont at the same time i would like to see what would happen hah but all in all good editions keep it going
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