The Scholarship Student Ch. 5

Story Info
Robert visits Mistress Calista's for advanced training.
3.9k words
4.15
35.3k
4

Part 9 of the 13 part series

Updated 10/24/2022
Created 12/28/2001
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

(Fdom, Bondage & Humiliation) This story is the property of the author. It is not to be changed in any way, nor published or shown at other web sites without the permission of the author. All comments appreciated.

The school year was nearing the Thanksgiving holiday break. Robert's studies were continuing in a very satisfactory manner and the extra activities with his Mistress were also very much on track. He had overheard Agnes and Jane discussing a cruise to the island of St. Thomas for the Thanksgiving holiday. Robert expected to be taken along. He mentally selected clothes he would take, and the fun he would have with his Mistress, Aunt Jane and Aunt Martha. He wondered if Ellen would also be taken along. Secretly he hoped that she would. Robert was studying in his room when Agnes came in and sat next to him. "Hello, Mistress Agnes, you look troubled, is something wrong?" Robert asked.

"No, Robert, there is nothing wrong, but, I do have something to tell you," Agnes replied and took his hand in hers. "You know that Jane, Martha and I are planning a short cruise to the Caribbean during the Thanksgiving holiday. We do not plan to take neither you nor Ellen with us. Ellen will go home to her parents and you will visit a friend of mine in New York City. I am sending you to her for additional training. She will pick you up at the airport and return you there for your flight home before school starts. Her name is Mistress Calista and I'm sure you'll enjoy her, Robert." He was stunned and hurt. He had expected to go to St. Thomas, but he accepted his Mistress's command without question.

"Since your cruise starts in two days, I'd best start packing for my trip to New York, Mistress," said Robert.

"No, Robert, you won't need to pack. You'll wear your suit and tie for the flight there and back. Mistress Calista will provide all the clothing you'll need during your training. Your flight leaves at noon tomorrow," Agnes said as she got up to leave. "Goodnight, Robert," she said as she left the room. Robert was visibly hurt, as he had looked forward to the trip to St. Thomas. He could feel his eyes getting moist, but successfully fought off crying. He decided to be a good soldier, follow orders and suffer his fate.

The huge jumbo jet flew effortlessly through the cloudless skies. Robert sat in a window seat watching the ground far below. He wondered about his upcoming training and what it would entail. The decision to send him to another Mistress, even for a week, was incomprehensible to him, as he thought that Agnes would train him, with help from both Jane and Martha. His thoughts were interrupted by the announcement that the plane was descending in preparation for landing.

Robert walked hurriedly through the massive JFK airport toward the terminal lobby entrance. He was to meet Mistress Calista there. Agnes had sent her his photograph so she would recognize him. He was to stand inside the lobby near the baggage area. Robert's apprehension precluded him from any, but the most cursory, sightseeing of the airport. He was concerned about his training and the Mistress that would provide it.

He stood nervously near the car rental agencies when he heard someone call out his name. "Mr. Robert Stone?" asked a man, dressed in a chauffeurs' uniform. Robert nodded yes and the man asked that he follow him. They walked out to the curb to a shining new Cadillac limousine, with darkly tinted windows. The chauffeur opened the door for Robert. He stepped inside to see three women beautifully dressed in fashionable silks and satins.

"Hello, Robert," said a very pretty brown haired woman, sitting in the center of the massive back seat, with two other women sitting on either side of her. "I'm Mistress Calista," she stated as the door closed behind him. Robert sat down in a leather seat facing the women. "This blond lady is Mistress Cassandra and the red hair belongs to Mistress Cerces," said Calista crisply. She directed the chauffeur to drive on and raised the dark partition between the passenger area and the driver to provide them with privacy. "Now, Robert, please remove your tie completely and place this around your neck," Calista said, handing him a studded leather collar containing several evenly spaced steel rings.

Robert moved quickly to obey, as he buckled the collar. Cerces leaned toward him and placed a small padlock on the collar and locked it securely. Calista smiled approvingly at the speed with which Robert followed her orders. "Remove all your clothes. I want you completely naked," Calista ordered. Robert hastened to comply. Mistress Cassandra gathered all of Robert's clothing, opened the partition and placed them on the seat in the custody of the driver. She closed the partition and smiled approvingly at Robert, naked and nervously wondering what would follow.

"Robert," began Calista, "For the next five days you will be completely, totally and absolutely subservient to me and my two assistants, Cassandra and Cerces. You will obey all of our commands immediately without question and will speak only with permission. You will endure everything we provide or visit on your body, without any unwarranted cries, expressions of discomfort or pain. You may not gaze on your Mistresses nor look them in the eyes without permission.'

"Further, you will always kneel in the presence of any Mistress unless ordered otherwise. You may kneel now, as I continue." Robert complied, as Calista went on, "I expect you to resist cumming with every fiber of your will and you will be punished if you do not. Obviously, you may only cum with permission. All of your activities will be videotaped and provided to Mistress Agnes at the conclusion of your training."

"Yes..." Robert started to say when Calista slapped him forcefully on his face, startling him.

"Never speak without permission. If you are not given permission to answer a yes or no question, you will nod, yes or no! Do you understand?" Calista told him. Robert nodded yes and lowered his eyes. He could hear the silk and satin rustling as he looked at the limousine floor. He felt someone grasp his ears and pull his head upwards to see that the three women were naked. Robert briefly saw Calista's small breasts as she pulled his head between her legs to her cunt.

"Service me, Slave!" she commanded. Immediately Robert's tongue sought out her cuntlips and clit to lick and suck them. Calista moaned with pleasure, as Robert felt thumbs and forefingers on each of his nipples. As his nipples were being pinched, pulled and rolled, he felt a hand wrap about and masturbate his now hard cock, with another hand fondling his balls. As the Limousine sped across bridges and through the city, Robert continued servicing Mistress Calista.

Calista squirmed and gyrated, pulling Robert's head closer, as she ground her hairless cunt into his mouth. Her moans and squeals preceded an explosive orgasm that spewed her cunt juices over Robert's mouth and tongue, forcing him to swallow her offering of cunt nectar. When Mistress Calista's orgasm subsided, she quickly switched places with Cerces. Robert was now ordered to service Cerces in the same manner as Calista.

Cerces was deliciously agonized by Robert's servicing tongue, while Cassandra and Calista fondled and masturbated Robert. He could feel his balls boiling with semen that demanded release. Robert fought successfully to prevent cumming without permission. Cerces cried out with pleasure as her orgasm racked her body violently. She came a second time as Robert flicked his tongue across and over her engorged clit. When her orgasm subsided, Cerces exchanged places with Cassandra who immediately brought Roberts' mouth to her cunt.

While Robert serviced Cassandra, he feared that he might cum from the fondling and masturbation of his cock and balls. He could feel Mistress Calista redoubling her efforts while masturbating him. Her fingers and palm, rubbed his engorged and bulbous cockhead, bringing him closer and closer to orgasm. He feared the unknown punishment he would surely receive, if he came without permission. Robert tried to struggle against the wonderfully adept hand stroking his cock, only to feel the hand around his balls momentarily telegraph that it could easily crush them. Robert stopped struggling and resigned himself to continue service Cassandra while mentally trying to avoid orgasm.

Mistress Cassandra screamed as her orgasm exploded. Concurrently, Robert could no longer sustain his resistance and he too erupted in orgasm. His cum spewed forth in thick creamy volleys that spilled and coated the plastic sheet on the limousine floor. He moaned as his cock and balls throbbed as they expelled huge globs of semen with each spasm. Cassandra moaned with pleasure as her orgasm subsided. She released Robert's head and breathed heavily as she recovered from her orgasm. Robert looked down at the puddles of pearly white semen accumulated between his knees on the floor.

"Look at me, Robert," Mistress Calista said, as she raised his head to look into his eyes. "You deliberately disobeyed me! You spewed your miserable cock fluid on my limousine floor! More disgustingly, you did it without my permission! You will be severely disciplined for your lack of resolve, Robert. Oh, how disappointed Mistress Agnes will be when she views this tape. What do you have to say for yourself, Robert?"

"I'm truly sorry Mistress, I didn't mean to cum…or soil your car…or…or to disobey you, but your fingers on my cock made...me." Calista interrupted his response as her open palm slapped painfully hard on his cheek.

"Silence! You worthless slut whore!" exclaimed Calista. "Lick up your despicable semen soiling my car's floor. It's lucky Mistress Cassandra had the forethought to provide the plastic film or you would have stained the carpet." She slapped him unsparingly again. "That will be kind compared to the discipline you will receive later tonight," she said, as she pushed Robert's face down to lick up the semen he had spewed on the plastic film. Robert licked his thick salty cum onto his tongue and swallowed each globule that he licked into his mouth.

When he finished licking the semen from the floor, Cassandra wiped his cock clean of semen with her finger and thrust it in Roberts' mouth. He licked the finger clean of cum and lowered his eyes to the floor. Mistress Calista grabbed his balls and clasped a light chain about them and pulling it tight. The chain was so tight that it was pained him severely, but Robert dared not even whimper. The Mistresses were amused at his obviously painful plight, but they ignored him totally as they engaged in small talk while the limousine sped on its way.

It was dusk when the limousine pulled into gated driveway and stopped. The gate opened slowly and the limousine drove through on a wooded winding road. It was several minutes before a huge stone mansion appeared between the trees. After a few moments more, the limousine pulled up to the front door of the mansion and stopped. A butler hurried down the few steps to the car to open the door. "Good evening, Mistress Calista, …Ladies," said the Butler as he helped the women out of the car.

"Good evening, Edward," replied Calista as she handed Edward the chain she held in her hand. "Here, take this miserable excuse for a slave to the cellar dungeon." The Butler nodded as he took the chain and pulled harshly on it to bring the naked Robert out of the car. "I'm famished, Edward. Has cook prepared dinner?" asked Calista casually.

"Yes Mistress. Dinner awaits you all," he replied.

"Wonderful…oh, Edward, feed this creature his gruel sometime tonight, if you have a chance," said Calista as she climbed the steps and entered the house. The other ladies followed her while Edward pulled Robert by his balls, to a doorway on the side of the house. His balls hurt as Edward roughly pulled at the chain. Roberts' balls were beginning to swell from the tight constriction around them. He tried to hurry, to keep up with the butler, but his efforts were thwarted as Edward merely lifted the chain eliminating all slack. Roberts' predicament worsened as he walked on coarse gravel in his bare feet. His tormentor chuckled as he pulled Robert to the side doorway.

The doorway opened to a landing with steps leading up to a tower Dungeon, a hallway to the main house and another set of stairs that led to the basement. Edward pulled Robert down the basement steps. The basement was dimly lit, dank and cold as Robert walked naked behind the butler. Edward stopped at a heavy oak door, which was arched at the top, and opened it, revealing another set of steps leading down to a sub basement. Robert followed the Butler down the steps.

The sub basement was warmer than the upper basement, but still cool. There were several cells with steel doors, each with a small window sealed by a steel shutter. Robert counted eight cells as Edward stopped outside a cell door. He could hear other movement and noises coming from the other cells, as Edward pulled him into the cell he had just opened. Edward ordered Robert to lay down on a wooden cot with a meager mattress. He removed the chain from Robert's balls, to the slaves' relief and hung it on a peg near the door.

Edward attached a leather collar, two inches wide and shaped as a cone, about Robert's balls. The device had three small chains hanging from the bottom of the collar. Edward hooked each of the small chains to a larger chain hanging down from the ceiling and pulled it taut, raising Robert's balls up. Any movement caused the device to pull at his balls. Next, Edward handcuffed Robert's wrists together, lifted them up and attached the cuffs to the same chain hanging from the ceiling.

Robert was nearly suspended by the balls and wrists. Any body movement caused severe pressure and additional pain to his restrained balls. Without a word, Edward placed clamps on Robert's nipples and attached the chain between the nipple clamps to the same chain hanging down from the ceiling. Now his bondage was complete. He could not release himself and any movement brought stabbing pain to his balls and nipples.

Edward extended Robert's torment by wrapping a wide leather wrap around Roberts' cock and fastened it tightly. The wrap contained multiple metal studs on the inside. The studs dug into his cock shaft and cockhead causing severe discomfort. That device too, was attached to the ceiling chain. Next, he placed and locked leg irons on Robert's ankles. He completed Roberts' plight by roughly inserting a thick butt plug into Robert's asshole without benefit of lubrication.

Satisfied with his handiwork, Edward left the chamber closing the door behind him, leaving Robert to consider his circumstances in the dimly lit cell. The tears welled up in his eyes. Robert openly wept at the predicament forced on him by his beloved Mistress Agnes, by sending him here for further training. Robert tried to sleep, but to no avail. He worried about his plight, as he was totally confused with the circumstances in which he found himself.

Suddenly, the door opened and Mistress Calista entered the room, followed by Cassandra and Cerces. The two lesser Mistresses raised his legs by the leg irons and hooked them to the chain hanging from the ceiling, leaving his ass cheeks totally exposed. Calista showed Robert a leather strap with a handle on one end, with holes and raised metal studs on the other. Calista smiled down at Robert and squeezed his cock wrap to watch him squirm and cry out in pain.

"Now, Robert, you must pay for soiling my limousine with your disgusting semen. You shall receive fifteen strokes of the strap on each asscheeks for a total of thirty," said Calista. "Cerces shall video tape your performance for Mistress Agnes's viewing. I suggest you comport yourself stoically, so you do not humiliate her." Without waiting for a reply, Calista struck him full upon the right asscheek with all the strength she possessed.

His scream resonated throughout the dungeon, as the pain burned into his body. His effort to catch his breath eluded him as the next stroke seared his ass flesh. There was no breath in his lungs to give voice to a scream, as he shuddered through the agony of the first two strokes. Mistress Calista paid no attention Robert's pleas for her to stop, as she continued to strap his asscheeks with all of her might. He was moaning and crying from the strapping, while rivulets of tears streamed from the corners of his eyes.

His body lurched with each stroke causing additional agony pulling at his nipples, balls, and cock. Careful to avoid striking his balls, Calista continued until the thirtieth blow landed on Robert's beet red asscheeks. Robert nearly fainted from the burning pain and his sobbing was barely audible, as Calista released the leg irons from the chain and allowed his legs to drop to the cot, adding pain to his already burning asscheeks.

Calista patted his cheek as she grinned at him and bid him good night. "This is what you have to look forward to, if you cum without permission again," she said sweetly. The three Mistresses quickly left the cell, slamming the door behind them, leaving Robert to his tears and pain. He sobbed for some time until sleep overtook his pain wracked body and provided some sanctuary from his agony.

Robert felt something roughly shaking his shoulder to awaken him. It was Edward, waking him up. Without speaking, Edward released Robert's arms, nipples, cock and balls from the hanging chain. He removed Robert's leg irons and helped him off the cot to stand upright. Robert was disoriented and his aching body needed several moments to regain his balance. Edward gave him the time needed to recover from his bonds.

Edward fastened the guide chain around his Robert's balls, again. He suspended a heavy lead weight on the three small chains hanging from the leather cone that encased his balls. The weight hurt as Edward pulled him out of the dungeon by his tender balls. Robert's arms ached from being suspended from the chain and his cock and balls were sore from their encasements. His ass cheeks still burned and, though he could not see them, he knew they were bright red.

Edward led him to the center of the antechamber outside his dungeon and pointed to a large wooden bucket in a corner. He motioned to Robert to relieve himself in the bucket. Robert did as instructed, but could not find any toilet tissue to wipe him self. Edward, held a hose, motioned for him to rise from the bucket and stand in the center of the antechamber near the drain.

When Robert reached the drain, Edward turned on the hose, showering him with cold water. He was startled as he shivered under the stream of cold water. Edward had Robert turn around to cleanse his asshole as well as the rest of his body. The cold water shocked him to full consciousness and soothed his still burning ass cheeks. When Edward felt that Robert was clean, he shut off the water and tossed Robert a towel to dry himself.

Robert was led, by the balls, up the stairs to the main part of the house. Still naked he was brought into a huge dining room. The three Mistresses were seated at the table along with several other people that he had not met. Only Robert was naked, and he was mortified appearing before the other clothed guests. He was led to the end of the long table where a pedestal stood and he was ordered to stand on it. The other guests hardly took notice of him as they ate their breakfast and engaged in small talk. Mistress Calista tapped her knife on her crystal glass causing it to ring out crisply each time she tapped.

"May I have your attention, ladies and gentlemen," Calista began, "this miserable slut has been sent here for advanced training to better serve his Mistress. His name is Robert. You all will have an opportunity to witness his training and interact with him," she paused for effect then continued, "Robert, these fine folks are my paying guests that have come here to live out their own particular fantasies. You, and they, will enjoy 'helping' each other realize their fantasy to satisfy their cravings, achieve their orgasms and in the process, enrich me."

12