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Lisa's stomach nearly sank when she saw Meredith position herself behind the man, with the long strap-on pointed directly at the man's spread ass.

Lisa was ready to shout and plead on behalf of the helpless man on the table. She wanted to stop this madness on his behalf. But she didn't. It wasn't her role. Her mouth was open in shock, and she briefly lowered her camera so she could see the anal penetration with her own eyes. It was a jarring sight. She raised her camera, pointed it directly at the anal penetration, and she snapped more pictures.

Monday. It was early morning and Lisa stood in her darkroom developing all of the pictures she had taken for Meredith. There were over 200 images total.

The first batches were ready. The image quality was beautiful, and she admired her own work. She knew that Meredith would be pleased with how the bondage room was captured. She knew that Meredith would also be pleased with how the male submissive was captured. There were stunning shots of Meredith in the outfit, and there were close-ups of the gold mask.

Lisa briefly looked through the rest of the film strips she had taken. She looked at the images of the man sucking the sex object, being spanked, then sodomized for a lengthy period by the large strap-on. Her heartbeat rose. Then she looked at the images of the man being jerked-off by Meredith. He shot a massive load of cum onto the floor, which he was later ordered to clean with his tongue.

Lisa felt a burning sensation between her legs. She was aroused in her darkroom, the same way she had been aroused in Meredith's bondage room.

She unbuttoned her pants and slid her right hand down her panties. She looked at the film being developed, of the man sucking the dildo while on his knees, and she touched herself sexually. She remembered everything she felt when she saw it for the first time. She visualized him being sodomized, and Meredith masturbating him. She touched herself thinking of the man sucking on Meredith's tits. She thought of all the verbally degrading comments sent his way, and how hard it made him.

Then, Lisa imagined herself being in the man's position. She wondered if she could possibly enjoy being made to suck a dildo, and being sodomized in such a degrading position. When she gave herself an orgasm in the darkroom when she knew the answer was yes.

Gold Mask & Black Dress

Two months later. Lisa wore a new dress when she went to Meredith's office. She had been requested to a private meeting. Once she reached the right floor, she had a brief discussion with the secretary, and she was allowed to enter Meredith's office.

The two women greeted each other with a hug, and they both sat down in their seats, with Meredith behind her large desk, and Lisa sitting in front of her.

"I can honestly say that you're the best employee I've ever had," Meredith stated. "That means something, given how many qualified people have worked for me over the years."

A proud feeling came over Lisa. "Thanks. I try my best."

"Do you like having me as an employer? I have a reputation for being a real bitch, which is well deserved."

"I don't think you're a bitch at all," Lisa playfully replied. "I think you're a strong woman. And you're easily the most intriguing employer I've ever had. Every week is something mind boggling. I love that. I always look forward to our meetings."

"Well, unfortunately, your services are no longer required," Meredith said in a blunt business tone. "You've completed your task photographing all of my submissives. I think you've done a wonderful job. Your work has far exceeded my expectations."

Lisa was taken aback. She had grown to love watching, and taking pictures, of Meredith's secret sex life. Going to her apartment on Saturday nights was the thrill of her week. And she privately masturbated every time she returned home. She had also grown fond of Meredith's company on a weekly basis.

"Oh, well I'm glad that you liked my work," Lisa replied, trying not to sound crushed.

"I'm not the only one that likes it. All of my male submissives agree that you've done an outstanding job with your photography. You'll be receiving a considerable bonus for this. When you leave my office, my secretary will hand you an envelope with the money."

"That's very kind of you."

Meredith smiled. "Not a problem."

"Is there any way that... we could... continue this?" Lisa asked with all of the confidence she could muster. "As a photographer, I think there's plenty more things we could explore, which we haven't already."

Meredith raised an eyebrow. "Really? So, the shy little photographer wants to continue working for me. That's interesting."

"Well, I'm interested in your hobby," Lisa reluctantly admitted. "It's fascinating stuff, and I think we've done great work together in terms of making art."

Meredith thought for a moment. "I may have just the thing for you. No guarantees. But it might be out of your league."

Lisa's attention was suddenly piqued. "What is it?"

"The bondage fetish is more common in the business world than you think. It's very popular amongst powerful men, because they love the role reversal. They love giving up control to seductive women after being the boss the whole day. Are you interested so far?"

"Definitely."

"Great. I'll contact the organizers of the event to see if you can join."

"Event?" Lisa asked.

"Yes, it's a small event which happens every so often. It's a bondage party, basically, where the rich and powerful go to have some real fun- the adult kind."

"That sounds like something I'd love to see."

Meredith grinned. "You have no idea. It's so dirty and vulgar, that everyone is masked. Everything is completely discreet. Plus it's a bit of a tradition."

"What would I be doing there?"

"Taking pictures. What else? Maybe the organizers of the event would like some beautiful pictures for a memorabilia or something along those lines."

"I can definitely do that," Lisa replied. "To be perfectly honest, ever since I started taking pictures of your bondage sessions, everything else I do at work seems so tame in comparison."

Meredith smiled, "I knew you'd like it. You're that kind of girl. Now if you'll excuse me, I have an appointment in a few minutes."

"Oh, of course. Thank you for your time."

Lisa stood up and extended her hand for a handshake before she left.

"One more thing," Meredith added. "My other friends don't always play nice. So if you want to continue working for me, then you better be sure."

"I'm sure."

Meredith nodded. "I thought so. We'll keep in touch. I'll contact you soon."

A week later. It was an early Tuesday morning. Lisa was awoken by a series of knocks on her door. She got out bed, briefly checked herself in the mirror, then answered the door. To her surprise, it was Meredith's secretary holding a small package.

"Good morning," the secretary said with a beaming smile.

"Morning, please come in."

The secretary stepped inside the small apartment holding the package, and Lisa closed the door.

"Sorry to disturb you so early," the secretary said. "I'm busy the rest of the day, so this was the only time I had."

"No worries. Do you want some coffee or breakfast?" Lisa asked.

"I'm fine thank you."

"So what brings you here this morning?"

"Meredith had contacted the organizers of the event," the secretary replied. "They all love your work, and they think your pictures would be welcomed."

"That's great news. I'd love to attend."

"There's a condition though."

"What is it?" Lisa asked.

"The bondage event is exclusive, and they don't just let anyone in. So you'll have to be initiated before you're allowed to take pictures there."

The news woke Lisa stronger than any cup of coffee.

"What do you mean?"

"There's an initiation process for new members. I'm told there's no way around it. You have to do it, if you want to continue working for Meredith."

"Well, what does this initiation require? Anything extreme?"

"It changes each time," the secretary replied. "I was initiated a few years ago, and it was pretty tame. But for other people, yikes. I wouldn't want to be them."

Lisa suddenly felt her mind spinning. She wanted the job more than anything, and she didn't want to disappoint Meredith by refusing.

"Tell Meredith I'll do it," Lisa said.

The secretary smiled and placed the package on a nearby table. "She knew you'd be interested. This is for you."

"What is it?"

"Open it."

Lisa lifted the cover from the package and she saw a gold mask sitting on top of a thin black fabric. The mask was elegant, and similar to the one Meredith uses during each bondage sessions.

"What's this for?" Lisa asked, as she picked up the mask to examine it.

"You'll have to wear it to the event. It's the same type that Meredith has, which will let people know that you're either her guest, or her submissive."

Lisa continued looking at it. "It's a beautiful mask."

"It certainly is. There's an outfit in the package also. You'll have to wear it. Nothing else, except for heels."

Lisa lifted the thin black fabric from the package. It was completely see-through.

"I'm not allowed to wear anything else underneath?" Lisa asked.

"Nope. Nothing. The event starts 7 pm on Saturday. A driver will come pick you up at 6, so be ready. You're allowed to wear a coat to cover your body when you walk to the car, but take it off once you reach the event. Don't forget to bring the mask, and your camera."

"Can I ask you a personal question?"

"Sure," the secretary replied.

"Do you think I can go through with this? I mean, in your opinion, do you think I can handle what goes on at the event?"

The secretary smiled, "There's only one way to find out."

Saturday evening. The elevator door opened and Lisa quickly walked through the lobby of her apartment building. She wore high-heels and a large coat. Underneath, she wore the see-through black fabric with nothing else. She held the package with her gold mask inside, and another container which had her camera. She walked as fast as she could so that no one would see her.

A black car waited for her, with the driver holding the door open. When she entered the car, she saw Meredith sitting in the backseat. Once Lisa sat down, the driver closed the door and drove towards their destination.

"You look cute in that outfit," Meredith said. "It's nice seeing you in something a little sexier than what you normally wear."

"Thanks. You look great also."

Lisa's eyes roamed Meredith's body, which was much more bare. Meredith wasn't ashamed of sitting in the car wearing only a thin black fabric. Every curve on her body was completely visible, and her large brown nipples could be seen through the thin material.

"You seem a bit nervous," Meredith noted.

"Kind of. This whole process is pretty intimidating for me. I hear there's an initiation I have to go through."

Meredith smiled. "You've heard correct."

"Can you at least give me an idea of what's going to happen?" Lisa asked shyly.

"I'm afraid not, honey. But don't worry. You're in good hands."

"I hope so. God, this is scary."

"Why are you here?" Meredith asked bluntly. "What's the real reason? It has to be more than just professional curiosity. Admit it, you're a secret slut."

"I'm not a slut."

"Then maybe I should have the driver turn this car around and take you back to your apartment.

"Wait," Lisa replied swiftly. "I'm here because I like what you do. I think it's exciting. I want to keep watching you."

"Do you have fantasies of joining in? Ever think about being whipped, spanked, or having a strap-on used inside any of your tight holes?"

"Yes. I have."

A sly grin appeared on Meredith's face. "Of course. I knew you had submissive potential since the day I walked inside of your studio. It's usually the quiet girls that become the biggest sluts"

"I'm not a slut."

"The initiation should take care of that. Remember, no one is forcing you to be here. You can leave anytime you wish."

A shiver of fear and excitement was sent down Lisa's spine. She wondered what Meredith meant, as Meredith simply turned her head away with a faint smile and looked through the window of the car.

Pain & Pleasure

The security gates opened and the car was allowed to enter the large property. The car stopped in front of a mansion, and the two women stepped out.

"This is where we put our masks on," Meredith said. "And take off your coat. It's time to show off that pretty body you have."

Lisa removed the coat and tossed it inside the car. A slight breeze of wind reminded her how vulnerable she was. She felt the space between her legs tingle from the cool air. Her pink nipples stiffened from a second round of breeze. Lisa closed her legs tight in a weak attempt to cover her womanhood.

Both women put on their gold masks. Lisa reached in the car and grabbed her camera. They closed the doors, and the car drove off.

The entrance to the mansion was guarded by two large men. They also wore masks, and they stood silently as the two women approached them.

"Password please," one of the masked security guards asked.

"Towel clip," Meredith replied.

"You may proceed ladies."

The guard opened the door and they entered the mansion. Lisa marveled at the extravagance of the building. It looked like it was built for a royal family. Paintings, decorations, and collectors items were all displayed on the walls. The carpet was red on the entrance which they entered. They walked down the large hall.

"You have to wait in the guest room for a while," Meredith said. "Someone will come get you shortly."

Lisa took a deep breath. "Okay."

"You'll be fine. Calm down."

"Can you tell me what's going to happen?" Lisa asked. "I'll be less nervous if I knew."

"No. Wait in the room until someone comes for you. Keep your mask on, and leave your camera there. There will be plenty of time to take pictures later."

Meredith opened the door and gestured for Lisa to enter the room. The guest room was plain, with a few pieces of wooden furniture. Lisa took a deep breath and entered.

She lost track of how long she waited. She never took off the mask. After getting bored of sitting and waiting, Lisa stood in front of a mirror and looked at herself. The mask was enchanting. She couldn't stop thinking about how her pink nipples and vagina were visible through the thin fabric. She questioned herself and her reasons for being there.

Before she could think any further, there was a knock on the door. A woman entered, completely naked, wearing only a gold mask.

"Follow me," the naked woman said in a soft voice.

Lisa followed her out of the room and they went down the hallway. It became darker. Many of the lights had been turned off and there was an abundance of candles burning in all directions.

There was a group of masked people standing down the hall. Some were naked, some wore suits. All of them wore masks. They stood in a circle, with Meredith standing in the center. Meredith was completely naked except for the mask.

It was the first time Lisa had seen Meredith's naked body. Lisa admired her toned figure and voluptuous curves with large brown nipples.

Lisa was led to the middle of the circle, standing directly in front of Meredith. The other masked guests in the room stood silently.

"Welcome Lisa," Meredith said. "The committee has decided to admit you into our private Club. It wasn't an easy decision, but the quality of your work, and your discretion, is what allowed for your entry. However, there are conditions to this acceptance. Would you like to know what they are?"

"Yes," Lisa nervously nodded.

"First, you are required to experience sexual submission for the group to watch. Secondly, I'm required to use 15 clothing clips on your body during the process. Finally, you are required to orgasm at least 2 times during the next hour. All of the conditions are final. You can either accept them, or leave."

Lisa took a deep breath. "I accept."

"Tell us why you accept. Why would you want such painful and degrading acts done to you? You're such a sweet little girl."

Lisa thought for a moment. "Watching your sessions these past two months has opened my eyes to something new. I want to continue being part of this."

"Even if it means having to go through with this initiation?" Meredith asked.

"Yes."

"What does that make you?"

"A slut."

Meredith nodded. "Remove your outfit. Show us your beautiful body."

There was a shiver down Lisa's spine. Despite the masks, Lisa could feel all eyes in the room waiting in anticipation. She slid the see-through outfit down to her feet and stood completely naked. She resisted the urge to cross her legs, and she allowed her cleanly shaven crotch to remain uncovered. She resisted the urge to cover her small breasts, and allowed her pink nipples to protrude.

Meredith took a step forward, and she was just inches away from Lisa. She reached out and touched Lisa's small breast, softly caressing it with her hand. She circled the pink nipple with her finger, then she pinched it hard.

"Oww..." Lisa gasped.

"Am I hurting you?"

"A little bit."

"Shall we stop then?"

Lisa knew she was being given a subtle ultimatum. "No. Please don't stop."

Meredith pinched the nipple even harder, causing Lisa to gasp again.

"You might not like this at first. But you will..."

A masked naked woman approached them holding a pillow with a small pile of clothing clips on it. Meredith picked up one of the clips, squeezed it open, and positioned it over Lisa's nipple. She slowly allowed the clip to clench the nipple, little by little. Meredith released her hold of the clip, and it clenched the bare nipple powerfully, causing it to swell.

"It hurts badly," Lisa said in a calm desperation.

"Do you want to stop? The conditions are non-negotiable."

"How long will the clip be there?"

"Until you orgasm twice tonight. I can speed things up if you'd like. It would be easier for a beginner like you."

"Please..."

Meredith reached for another clothing clip, and she mercilessly used it on Lisa's other nipple.

"Ahhh..." Lisa yelled.

"That's 2 clips so far. 13 left."

"Where are you going to put them?" Lisa asked, almost fearfully.

Meredith leaned forward and whispered in Lisa's ear. "How about your labia? That's the traditional spot for a woman. Do you want to quit, or join our club?"

It was the point of no return. Lisa made up her mind within a moment, even as her nipples ached badly. Her once pink nipples were turning a dark shade of red.

"I refuse to quit."

"Then lay on your back. Spread your legs."

Lisa laid on her back on the carpeted floor, with her legs spread wide open. Her womanhood was completely exposed, awaiting the pain from the clothing clips.

Meredith got down on her knees and took her time examining the pussy in front of her. She studied and admired it. Meredith picked up a clothing clip, squeezed it open, and lifted the left side of Lisa's labia.

"This may sting a little," Meredith warned. "You're a grown woman. So act like it."

With those words of caution, Meredith cruelly released the clip, causing it to suddenly clench the labia, making Lisa scream. Meredith smiled and reached for another clip, this time, releasing it gently to the labia. The pressure of the second clip caused the labia to change shape. Meredith continued the process until the left side of Lisa's labia was covered with clothing clips.

"How does your cunt feel?" Meredith asked.

Lisa laid her head on the carpet and struggled with the pain of her nipples and labia being squeezed tightly by the clothing clips.

"It hurts really bad."

"That shows you're human. I'm proud of you for lasting this long. Your initiation is tougher than most because your financial background isn't the same as ours, and you don't have a history of bondage."

"I understand."

"Good slut. The hard part is almost over."

Meredith reached for another clothing clip, this time placing it gently on Lisa's right labia. Lisa didn't flinch anymore, and she didn't moan. She had already become used to the pain in her sensitive sexual areas.

The pattern continued until all of the clips were used on Lisa's pussy. The once cute and attractive vagina had suddenly become deformed. The vaginal lips were stretched in different directions like clay. Meredith looked inside Lisa's pink pussy and saw that it was wet.

"You're ready for your first orgasm," Meredith said. "Aren't you?"

"I am."

Meredith spanked the center of Lisa's pussy without warning. The shock caused Lisa to scream in a rare combination of pain and pleasure. The spanking of Lisa's pussy continued until the tips of Meredith's fingers were coated with vaginal fluids.

"You're soaking wet, my dear," Meredith said. "I think you're ready."

With that, Meredith inserted two fingers inside the pussy, and she used fingers from her other hand to play with Lisa's clitoris. It was a potent combination. Her fingers were skilled in sexually pleasing other women. The fingers were being worked in a particular and skillful manner.

Lisa moaned in pleasure. She no longer cared about the group of masked people watching her. At that point, all she could think about was the burning sensation in her pussy and nipples.

The fingers continued the frantic work. Meredith went faster and faster with more intensity. Lisa's body shook. She cried.

Meredith sensed that Lisa was on the brink of her first orgasm, so she worked even harder, fingering the hot pussy. Lisa squirmed, cried, and her back arched. Lisa let out a loud scream and her toes curled, then her body went limp.

"That's one orgasm so far," Meredith smiled, looking at her fingers which were covered in pussy juice. "Now it's time for orgasm number two. It's going to be a bit tougher. You can quit anytime you want. Ready?"

"Yes."'

Meredith snapped her fingers, and two masked naked women came and wrapped leather straps around Lisa's hands and ankles. They guided Lisa to turn over, so that she was on her hands and knees. They spread Lisa's hands and ankles, and locked them onto hooks on the ground. Lisa was on her stomach, completely bound and helpless.

"Your final test is 7 inches in your ass. Don't worry kitten, I'll use plenty of lubrication for you."

Lisa's eyes widened. The bondage restraints on her wrists and ankles were tight, and she had nowhere to go, unless she decided to quit, which would permanently end her relationship with Meredith.

She refused to quit, even when she felt Meredith's fingers push inside her ass. The fingers were coated in a thick lubrication. The fingers probed her tiny asshole as far in as they could go. Meredith wasn't gentle. She was all business. Lisa just laid her masked face flat on the floor and accepted the finger penetration inside of her ass.

"I'm wearing the strap-on you've seen me use so many times on my submissives," Meredith said, laying on top of Lisa's body. "I'll go slow at first, but I expect you to keep up with my pace."

At that moment, Lisa had flashbacks of all the masked men who had been anally fucked by Meredith's variety of different strap-ons. Lisa had imagined being in the submissive role so many times before. She had never imagined that it would actually happen to her.

The tip of the strap-on pressed tightly against Lisa's anus. Meredith used her hands to spread Lisa's ass cheeks apart, which allowed the sex object to penetrate the tiny little hole. Lisa groaned loudly when the object entered her body. It slowly made its way inside of her rectum. She clenched her hands tightly and gritted her teeth. When the object continued the slow journey in her ass, her mouth opened and she let out a groan. It continued until Meredith's crotch pressed against her ass.

"Brave girl," Meredith said in Lisa's ear. "Most people would have quit by now. Not you. You're almost done. This is going to feel good in a moment."

Meredith slowly pulled out of Lisa's rectum, and then she gave a soft thrust, pushing it deep inside once again. She paced the rhythm slowly in accordance with Lisa's tightness. Every thrust made Lisa groan.

Lisa looked around the room while she was being sodomized. The masked guests all stood silently and watched the show. She wondered what they thought of her. She wondered if they were aroused. She wondered if they wanted a turn with her ass.

The thrusting inside Lisa's ass continued. The pain soon joined with pleasure. Her nipples and pussy still ached badly from the clothing clips. The pain continued to grow. Her anus was still hurting from the 7 inch sex toy, and she never fully got used to it. But there was a strange pleasure growing inside of her. Being anally fucked for everyone to see was titillating. It was sensational.

The thrusts became faster and deeper. Meredith showed less mercy, and less tenderness, and really started being rough on Lisa's ass. Lisa was being treated like any one of Meredith's submissives, which was a compliment to Lisa. It meant that Meredith knew that Lisa was tough enough, and worthy enough, to take the anal punishment.

"I can sense your orgasm approaching," Meredith said, while thrusting. "Cum for me, my dear. Do it, and join our club."

"I'm trying," Lisa gasped.

"Maybe this will help, kitten."

Meredith reached underneath and began to play with Lisa's clitoris, while continuing to sodomize her. Lisa's sexuality was being assaulted on all sides. Her nipples ached. Her labia ached. Her anus and rectum were being pounded without mercy. Now her sensitive clitoris was being massaged.

"Oh my god!!!" Lisa cried.

The young woman's back arched violently, and her hands and feet clenched with all their might. Fluids shot from her pussy and coated the floor. For the second time, she became limp once again.

"Congratulations," Meredith said, rubbing Lisa's hair. "You're a member now."

Meredith slowly pulled the sex toy out of Lisa's ass and stood up. She watched Lisa on the ground. Lisa was sexually drained for the moment, and was slowly coming back to life. The other masked women came to untie Lisa, and they unclipped her nipples and pussy. Lisa stood, and the other masked guests in the room gave an applause for their new member.
Epilogue:

Six months later. Lisa wore a beautiful dress as she waited in the elevator. She was holding a large yellow envelope. Once she had reached her floor, she greeted the secretary with a familiar smile. Then she entered Meredith's office.

Pleasantries were exchanged, and Meredith opened the envelope to look at the newly developed pictures while they both sat down.

"You've outdone yourself," Meredith noted, looking at the pictures. "Exquisite work. The camera angles, the lighting, the timing. These are perfect. Our friends at the club will love it."

"Thanks. I hope they enjoy it."

"It's a shame that these pictures have to remain private. Your talent as a photographer should be recognized by a lot more people."

"Recognition from you is enough," Lisa said boldly.

Meredith smiled, "Such a sweet girl."

"I saw my check sitting on the secretary's desk. I'm sure it's another generous payment, which I'm very grateful for. But today I was hoping for something a little more... extra..."

Meredith reached down to remove her panties underneath her office skirt.

"Very well. You have 30 minutes before my next meeting."

"Thank you."

Lisa walked over to the desk in a casual manner. She tried to hide her impatience, but both of them knew how Lisa truly felt. Meredith opened her legs and watched Lisa get down on her knees.

30 minutes was the limit, and so Lisa wasted no time eating the pussy of her dominate teacher until the point of orgasm.
The End
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