Teacher's Dilemma Ch. 03

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As soon as she parked her car in her home, terrified, she got out. When she had returned to her own office, there was a text waiting for her from her master:

YOU THOUGHT YOU COULD BREAK THE SURVEILLANCE RULE AND I WOULDN'T NOTICE? GO HOME, EVERYTHING GOES IN THE BOX. THERE'S A BOTTLE OF OIL IN THE BOX.

APPLY ENTIRE BOTTLE EVENLY ACROSS YOUR ENTIRE BODY. HEELS WILL UNLOCK, SO ENTIRE BODY. THEN TAKE YOUR WAITING POSITION.

As instructed, she placed all her clothes in the box, including the heels. The bottle of oil was larger. By the time she finished applying the oil right outside her front door, she had a glistening shine on her body. Hair tied in a ponytail as her usual orders, she took her waiting stance outside.

She felt like she waited there forever when the door unlocked. Immediately rushing inside, she saw her daily nightmare, Rose standing in the middle of the living room.

Rose began yelling at her immediately. "What did you think whore, you'd break rules, and your master won't notice? Now we'll have to show you how punishments can get worse. We've been too lenient with you; you need to be taught what happens when a slave deliberately breaks rules."

She saw Rose fetching something out of a bag. It was shining black and small. Then soon Rose had a latex top in her hands, and it was a weird top. When she started putting it on, Jessica realized the top was too tight, it wouldn't fit. Then she realized the purpose of profusely oiling her body.

Rose put it front to back like a straitjacket, only difference being, it had a giant cut in exactly her tits. They made the dress exactly as per her body curves. It covered her entire top body, except for her tits. Her entire tits were hanging out for open display.

The top covered her entire neck, arms, abs, and stopped just above her cunt. It was too tight; it took her several minutes to adjust to the tightness of the top. Once the zipper at the back was all the way up, Jessica looked like a sex goddess, inviting everyone to fuck her.

The next step was even more difficult for her. Rose had bound both her hands with similarly shining strong tape, like she was wearing a straitjacket, only difference being her mistress has bound her hands backwards. Rose kept her hands painfully tight, making sure her tits pronounced even more outwards.

Once done, came the next part of the puzzle. She inserted her infamous four torture balls up her cunt, followed by a beaded dildo with exactly same sizes as the anal hook she had earlier. Her sphincter muscles closed around the dildo at once. It was all the way in. She was painfully full in both her holes.

Then came the next part, her pants. It was same color and material as the top and had attached boots with it. The boots had 7" pencil heels on them. It took over fifteen minutes for Rose to pull those excessively tight pants to pull above her waist. Once tightly adjusted, as with the top, pant also had giant cuts to show her entire cunt and ass.

Rose had dressed her in the most erotic way; the dress covered all the unnecessary body parts. Then there was a black carbon fiber serving tray attached right on top of her bellybutton, through a tight black nylon thread around her waist. She felt Rose attaching another thread that went upwards through her side boobs all the way behind her neck, like an apron. Second thread's purpose was to supply better structural balance to the tray.

Once satisfied with her work, Rose said, "There's a party at your house tonight and you're the server as a punishment. Practice walking with drinks on that tray. Do not spill and waste drinks while walking and remember to follow party rules."

"1 - Each time anyone notices you spilling the drink on tray, that person may punish you on spot with whatever they deem fit."

"2 - After each shot, guests will suck lime and salt from your nipples."

"3 - Since it's a punishment, you're not entitled to cum at all, no matter what happens."

"4--You will treat each guest in the party as master/mistress. Follow orders given by anyone in the party without question."

"5 - The stuffing cannot leave any of your holes during entire party, unless explicitly specified."

"6 - You cannot look anyone in their eyes, always look at the floor."

"7 - Thank each master/mistress before and after following their command."

"All permanent rules will always apply. Punishments upon breaking rules during this party will be much more severe. All the best, my slave."

Rose helped her fill the tray with small shot glasses with water and let her practice walking carefully. Next one hour passed, and she got a hang of things and was no longer spilling the water while walking. But the dreadful thing was her legs were sore already, and she was uncomfortable walking. Rose didn't allow her to sit.

Jessica looked at the clock and saw it was 8:50PM. Then turned around to see Rose holding a collar in her hands and said, "Guests are about to come, lets finish your look for the night."

It was a black leather collar with silver shining large text on it which said, "PROFESSOR WHORE", right at the center. Once the collar was in place, like everything, it was also painfully tight. Jessica was having difficulty breathing. She thought to herself that she'll pass out before the party ends due to lack of oxygen.

By the time it was 9 and the first bell rang, Jessica had set a breathing rhythm. Still, the oxygen supply wasn't usual, but at least she didn't feel like passing out.

First guest was her master along with an Asian girl who was also looking at the floor. But she was wearing a professional suit for a server at a very high-end gala dinner. She had on a white shirt, black trousers, black leather shoes with a bow tie.

Tyrone spoke first. "This is Anna, and she'll be helping you place those drinks and other order on that tray. She's not the major attraction for the night, you are. So, she'll not leave the kitchen at any point. Her only job is to place orders on that tray, rest is yours."

With that, Anna placed her right hand on the small of Jessica's back and directed her towards the kitchen. She had specific orders of her own. Do not speak to Jessica at all throughout the party.

Gathering a lot of courage, Jessica whispered in Anna's ears, "Are you also their slave?"

Extremely terrified girl looked up, placed her index finger on Jessica's lips and shook her head frantically. Seeing her expressions, Jessica knew they could not talk to each other. They had now stocked her kitchen with various kinds of liquor now. There was vodka, tequila, a wide variety of whiskey and scotch as well.

Soon the house started filling in. She saw among the people she was familiar with were Reggie, Terry, David, Mark, Rick & Jamie. Rick and Jamie had brought two blonde girls with them as well. She assumed their girlfriends. Reggie and Terry had two black women with them as well, while David had a Latina woman.

Anna had now stacked Jessica's tray with vodka shots, along with slices of lime and a small bowl of salt. As she turned around and started walking towards the guests, balls in her cunt and the beaded dildo up her asshole started vibrating. The problem was, this vibration was more intense than any of the earlier times. She had to stop and take a few deep breaths to compose herself. Once calmer to the intense pleasure sensations, she started walking towards the guests.

Both brothers jumped to the chance and stepped forward, picked a slice of lime each, rubbed on and around both nipples followed by some salt. Together both raised the shot glasses and said, "Cheers!" and just like that bottoms-up.

Immediately placing the empty glasses back on the tray, they started sucking each of her nipples. With the use of experienced tongues on her nipples, Jessica felt like she would cum right there, standing in between both brothers. Suddenly, she felt a finger rubbing on her clit vigorously.

Her legs started trembling. She had to focus on staying stable and not let the drinks spill and hold on to her orgasm. This was too much for her. She couldn't control her loud moans. If this was not a punishment, and if her mistress allowed her to cum, there would be a river flowing out of her cunt by now.

Then just like that everyone left, and she felt disappointed with no mouths and the fingers. She felt too lost in her lust and need to cum; she didn't realize Rose's stern and angry look. It came to her mind the rule; turned towards Rick. "Slave would like to thank you, master for enjoying her services. It would be her pleasure to be of any use to her master."

She repeated for Jamie as well. Then she saw the young blonde girls walking towards her. One of them said, "I didn't believe when Jamie talked about the professor whore. You sure are one. Anyone else in the university knows about her extracurricular hobbies?"

"No, not yet. It all depends on how the whore behaves. The ultimate punishment for her would be to let everyone know what a true whore their professor is."

Jessica felt fear creeping in her head. These blondes were students at the university. Things are getting out of hand now; more students are getting involved in her sexual adventures. Then she heard Jamie continue. "Would you behave properly, whore? Or should we let the students and faculty know what you really are?"

"Master, your whore slave will behave exactly as her masters and mistresses command. She will be always grateful to her masters and mistresses for their discretion by keeping her secret life hidden."

With that, both girls took their shots, and exactly how Rick and Jamie had. But this time after both the mouths left, one girl was rubbing her clit expertly and in between would stop and give her five hard slaps right on her clit.

On the third cycle Jessica couldn't take anymore and desperately said, "please mistress, slave begs her to have some mercy. This slave could not control any longer, mistress. Please give your humble slave some time."

Continuing the cycle fourth time she said, "if you can't control then cum. What's the problem?"

"Slave doesn't have permission to cum, mistress."

Out of curiosity, she turned towards Rose with a questioning look. Rose responded, "this slave is on a punishment and cannot cum during this party."

"That's no fun Rose. I think everyone would have more fun if this whore keeps coming every time. She serves her masters and mistresses," said the other girl, sounding disappointed.

"Rules are rules, Claire, and they don't change just because you have different expectations from this party," responded Rose in a stern and overpowering voice.

Jamie gave Claire an angry look, which brought her down to her place. She got the idea now who real bosses of the party were. And with that, the hand left Jessica's clit. She was still trembling from the intense sensations and the vibrating stuff in both her holes. It took her few more minutes to control her orgasm and compose herself. This was going to be the most difficult punishment for her.

By the time it was 10PM everyone had their first rounds of shots and a go at her clit. She was now hyper-sensitive and when she reached towards Tyrone one more time, she said, "master, your humble slave begs her generous owner to grant her permission to cum. Please, master, your slave is too sensitive and wouldn't be able to control anymore."

"You can cum slave nobody has stopped you. Just remember that severe punishment will follow it."

Jessica knew that it's impossible to control anymore. The first person to stimulate her clit will be successful to fetch the river out of her cunt. But to her surprise, during that round nobody did. Then bringing out his phone, Jamie said, "Everyone join us in the living room, we're watching a wonderful movie. Both Anna and Jessica leave you tasks and join us. It's a really amazing movie."

When everyone gathered and took their seat, apart from Jessica and Anna (they didn't have permission to sit), he played the video from his phone to the smart TV. And to her horror, the video was of her office adventure. Ten minutes in, everyone felt turned on and shocked by the events in the video.

Jessica saw the black woman with Reggie walked and stood behind her and said, "I am mistress Taylor." With that she started the same rhythm of rubbing her clit followed by few hard slaps on it. She was now whispering in Jessica's ears from behind her while focusing on the video and intensifying her actions on the clit.

Jessica was breathing heavily by now and tried everything in her power to control the orgasm. The lack of oxygen, vibrating balls and anal dildo, the realization of her own actions in the video, along with the pleasure on her clit, was way too much for her to control. As she saw herself having an orgasm on her own office desk while Phillip was outside and clearly audible in this video, all hell broke loose.

With a loud and vocal grunt, she yelled, "Ah... fuck.... me... I'm... fuck... me... Ah... Ah... Ah... God...", the balls dropped out of her cunt and with intense pressure came out the entire fountain of fluid that had been building inside her for so long, "Ah... Ah... God... Oh... my God... Oh... Fuck... Me...", Taylor had by now wrapped her one hand around her tits from behind to control her body and other hand was still vigorously rubbing her clit.

Jessica was yelling and grunting loudly. She felt like her entire neighborhood would have heard her screams by now. But she couldn't control any longer and loudly begged, "Please... please... too... sensitive... please... mistress... too... sensitive..." with that she passed out in Taylor's arm.

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Jessica woke up next morning naked on her bed, covered completely with dried sperm. What happened yesterday? Last thing she remembered was one of the most intense orgasm of her life, wrapped around the arms of Taylor. After that everything was a blackout. How was she covered in so much cum? No matter how hard she tried, nothing came back.

After finishing her morning routine, she went out to the living room to prepare for her workout session. Entire house was a mess and on the couch was Rose. She went to her and raised her hand to ask the question.

Rose said in her tired haze, "Speak slave."

"Mistress, your slave couldn't remember what happened yesterday. Would mistress be so generous and tell her slave what happened after the slave passed out?"

"If you don't remember, slave, then it's good for you. I don't owe you any explanation. Get on with your day."

Realizing she won't get anything out of her, Jessica turned and left her house for her morning workout session.

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Once alone, Rose dialed the number. "Ty had been correct always about you. You are a crazy shit mastermind. Last night was real fun. Best night of my life. And don't worry, your cover is still safe. She remembers nothing from the moment she passed out."

Response on the phone was, "I know she remembers nothing you dummy, it's not a coincidence that she doesn't remember. Everything is part of the plan. Do your part and don't get too cocky with me. I'm not Ty."

When Rose saw the disconnected phone call, she felt like someone had punched her in the gut. No one had ever talked to her like this.

"Who does she think she is?" thought Rose.

[For readers--Don't worry, Jessica will find out what happened that night after she passed out, in a future chapter as her character develops even further. Along with her, everyone else will also get to know what exactly happened?]

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Jessica felt like everyone was hell bent on destroying her entire life. She wasn't safe at university, and she wasn't safe at her own house. Her workout regime was getting even more intense. Massage guy made sure she always leaves on the verge of a massive orgasm but never allowed a release. At home after so much of tiring physical and mental day, Rose will practice her bondage skills on her. She had to practice her Kegel exercises to the extreme. She had to hold heavier objects from the strength of her cunt muscles even though Rose brings her beyond the limits of orgasm but never allows her to cum.

From past few days her mistress would not allow her to cum, even though she had been holding it beyond her limits. Her brain had stopped functioning properly now. She couldn't focus on her work at all. Every single second of the day, her brain was screaming and begging to get some relief.

Their plan was working, increase the sexual appetite and then deny. Jessica couldn't hold on to her orgasms any longer and did not know when her mistress would allow her the pleasure. She knew there was only one way left to beg.

Following Friday evening her massage therapy became way more erotic than it had ever been. When she reached home and stood naked, facing towards her neighbors in her waiting position. Door unlocked around fifteen minutes later. She entered inside and saw her mistress siting on the couch watching TV.

Jessica kneeled in front of her feet, gently picked her left foot, and kissed the sole of her foot passionately as if her life was in that sole. She repeated same gesture on her right foot and begged, "Mistress, your humble slave begs permission to cum. Your slave will do whatever you wish from her, please have mercy on your slave and allow her to cum, just once."

This had been the entire plan, but Rose was skeptical of it. But it worked like a charm. Putting her finger on Jessica's chin, she raised her head so their eyes could meet. Her eyes were moist. Rose said, "Slave, you already have to do whatever I demand, what's new that you're offering me here?"

Thinking for a while she couldn't come up with anything so dejected, she begged again, "Slave has nothing new to offer to her mistress but herself. This slave offers herself completely to her mistress if her mistress would be so generous to grant her permission to cum."

Rose didn't know why this was necessary, but Tyrone insisted on playing with her head. He didn't care about fucking her physically as much as he enjoyed fucking with her head. So, pretending to think for a moment she said, "I want something permanent on my slave to let her always remind that she's owned by her master and mistress. What do you think slave can you offer that?"

What does she mean by Permanent? How can she let anything permanent done to her? There were again questions spiraling in her head when her lust demanded to cum, no matter what the cost, so she said, "Yes, mistress, your slave will be happy to please her mistress in whatever way necessary. Your slave agrees to have something permanent to denote her devotion to her master and mistress."

Rose jumped in excitement and shouted in glee, "Perfect. I'll plan everything. Tomorrow you'll skip your gym sessions; I'll get it approved by your master as well. We'll both get what you desire so much."

That night's bondage practice and Kegel exercises, Jessica had permission to cum as much as she wishes. She had nine mind-blowing, lava-squirting, and earth-shattering orgasms. The fog that had settled in front of her eyes disappeared. She felt so much better now. This was the first night since Rose started living with her; she had slept like a baby. Rose told her they must leave early around 6:30 in the morning.

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November 30^th, Saturday