Miss Finny's School for Girls Ch. 02

Story Info
Ms Finny gets girls on track, Misty arrives.
5.4k words
4.1
5.3k
2

Part 2 of the 4 part series

Updated 01/01/2024
Created 12/26/2023
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
DirtBoss
DirtBoss
139 Followers

Jim arrived at his new home after work. He and Nancy had just started this new life because his mother-in-law had Miss Finny for her debutant upbringing. She disagreed with how Jim and Nancy were bringing up their daughter, her granddaughter, in a more modern way.

His body was now bare of hair. His cock and balls were locked away in a cage. This forced him to use the bathroom while sitting, like a little girl. He wore Miss Finny's plug in his ass, and she would take it out here in a few minutes and fill his bowels with hot water and soap.

His wife is also locked away from his husbandly duties. Miss Finny had stated that they could earn conjugal visits, but they both had a lot of training to do before this took place. Jim removed his clothing, folded it neatly, opened the door, and crawled into the house naked, except for his cock cage and butt plug.

He saw his wife naked, except for a chastity belt. Hand wash garments in the kitchen sink. Another woman was in what looked like a maid's outfit, with her hands bound behind her back and kneeling with her back to him. Her skirt was bunched around her waist, so he could see her chastity belt as well. Her large, milky ass was cleaved by brown leather.

Miss Finny was seated at the table, eating her dinner. An empty bowl sat in front of the woman on her knees. One with some food in it sat to the left of the kneeling woman. Jim already knew to crawl into the bathroom.

He had left his work clothes folded at the entrance. In the bathroom, a large, clear bag is hung on the shower curtain rod. Jim stood, took the bag, filled it with hot water, and put soap in it. He rehung it from the rod. He carefully pulled the plug from his asshole, as it was very painful.

Jim inserted the enema nozzle and released the clamp about halfway so he could get used to the flow with a minimum of cramping. He put his face on the cool floor of the tub and waited for the first cramp to hit.

Jim had married the much younger Nancy after being in a relationship where his ex-wife had wanted Jim to dominate her, and he tried, but it just was not in his nature to be mean to her. He just loved Nancy and the way she was always a take-charge girl.

She did not boss him, but she did have expectations and required him to meet them. Their six-year-old daughter took after her grandmother and was bossy. Now he found himself at the mercy of this evil old woman, whom Nancy's mom had all but given them too. He was older than his wife, but he loved her dearly, and she seemed to be okay with the situation, so he was going with it. He was most of the way through the bag when Miss Finny entered.

She stood in the doorway for a moment, thinking. "This is how every man should look in the evening. Ass up and receiving a cleaning. Face on the floor. If only I had my strap on and could make him whine and cry right now."

Miss Finny stepped inside and checked the enema bag. There was still half a gallon to go.

"Don't remove the nozzle when it is finished. Clamp the hose so you don't push soiled water into my bag. I will return to remove the nozzle and allow you to shower."

Jim groaned, "Yes Miss Finny."

She looked and admired how much better the male body looked when it was not covered in hair. Misty should be here Monday morning to take over the school. Miss Finny had continued the school that started with the settling of the territory; she was the third school Marm in the last 100 years.

Misty was taking over the teaching duties of the school and would be able to use both men and women in the sex education sections for 9-12 grades. But more specifically, the real teaching happened in the over-18 class before the girls graduation. The girls learned so much faster with a living model that reacted to their touch.

Frank burst into the house fully clothed with a black eye.

"I am here for my wife. We are not going to participate in this shit, where is she?" Vivian looked up from her spot on the floor in terror. She watched as Miss Finny covered the distance after grabbing a quirt.

Miss Finny did not say a word and began to whip Frank about the head and shoulders with the cruel quirt. He backed out of the door, yelling about a steel cage on his cock, and he was not staying for this. He was going to the police. His wife and daughter had been kidnapped. Miss Finny slammed the door and looked at Vivian on the floor, crying.

"Do you wish to leave with that man?" Miss Finny asked with eyes boring into the back of the crying woman.

"No, ma'am, it is too much for him to lose everything. For my mother to take everything of value in his life and lessen his manhood like this. I want to get my daughter back; the only way is to do what my mother requires." Vivian blubbered while continuing to scrub and having a few hitches in her voice.

"That is to be here with you, so my daughter is trained properly by the school. I will do my best to please you, Miss Finny. That should please my mother," Vivian said, tears pouring down her face.

"Good girl. He will cool off and probably come back begging. If not, he probably would have ended up abusing you and your daughter in the future if some challenge ever came into your lives. I have a man in the bathroom to deal with, and it looks like Nancy is done laundering clothes," Miss Finny said, hanging the quirt back on the door frame.

"You can clear the table and start cleaning the dishes and the kitchen. Nancy can eat once the laundry is out on the lines," Miss Finny said while dialing Victoria on the phone.

Miss Finny explained to Victoria what had happened to Frank and that he was going to involve the police. Victoria thanked her and said, "Consider it taken care of!"

Miss Finny entered the bathroom. Jim had been drooling down from his cage onto the surface of the tub. Miss Finny grabbed the nozzle and began to rub his perinium with two fingers and hard pressure. She began to push him back and forth across his prostate. Jim began to moan into the floor of the tub.

"Do you like this little Jimmy?" Miss Finny asked.

"Yes, ma'am, it feels nice, like pressure on the back of my cock. Oh, that is nice. Oh, what are you doing? My cock is dripping. Oh, my god!" Jim moaned as Miss Finny pushed, pulled, and rubbed.

"This is called "Milking the prostate," and your wife will eventually do this until you quit leaking fluid three times per week. I usually make you catch your leaky cock fluid and drink it. This time, I won't require that because we are not going to finish."

She quit and pulled both hands away, and Jim's dry hips humped the air, and the string of precum had started to make a quarter-sized puddle on the floor of the tub.

"You will find yourself hornier after milking than you were before, but it has the same health benefits as orgasming from a cancer standpoint. That is why we do it—for your health and our satisfaction—and you are even more susceptible to doing as we ask. When I pull the hose, remember to put your hands behind your head and start the shower to wash the nasty stuff down the drain." She stood and pulled the nozzle from his rectum, and he followed instructions to a letter. Tonight, she would teach the girls to prostate massage Jim, and until completion, he would then be allowed to sleep in the shed on his blankets while the girls slept on large pet beds at the foot of her bed. They would draw straws to see who woke her in the morning.

After dinner and dishes, Miss Finny put Jim in an armbinder on his knees on the kitchen table. The fingertip of the armbinder was tied to a hook in the ceiling. The 3" heavy black collar around his throat was tied to a second hook in the ceiling.

Miss Finny required the girls to lay out hand towels behind Jim and under his cock in the cage.

"There are many ways to get this done. I employ three, but tonight we will only do two of them, as the third requires my ten-inch strap-on dildo. We will have Nancy start as this is her husband," Miss Finny stated.

Nancy moved over to Jim, his darker skin in contrast with her milky freckle covered body.

"Put the blindfold over his eyes; we don't want the male to be distracted by anything as we milk his prostate. Men are so easily distracted," Miss Finny explained as Nancy complied.

"Remove the plug from his rectum slowly. It should still be well lubricated from his cleaning," Miss Finny instructed.

Jim moaned as he felt his wife turn the plug and slowly pull it past the stretching ring of his asshole.

"Remove the cage and release his nasty little cock. Then take the coconut oil and rub it in to make him smell better and get that little thing to stay at attention. Vivian, Nancy was not here for advanced sex education; you girls got it after your 18th birthday. Show her how to know when a man is about to make a mess with his cock," Miss Finny instructed.

Vivian walked over and stood slightly behind Nancy. "Grab Jim's scrotum and collect the testicles in your palm, stroke him until you feet the testicles try to pull through your loose grasp."

Nancy did as instructed. Jim was moaning while trying to push with his hips. The quirt went right past Nancy's left breast to land on the top of Jim's ass vertically and down his right thigh.

"Stop moving your hips. This is not for your pleasure; it is for your health," Miss Finny yelled.

Jim moaned deeper and louder, but his hips stopped moving. Nancy thought Jim was harder and larger than she had ever had his cock before. Nancy felt the testicles tug upward slightly, and she let go of both the cock and the testes.

"Oh, fuck, oh, fuck." Jim moaned as his cock bounced with his pelvic floor muscles contracting. Pulling the testicles up beside the base of the shaft, leaving the scrotum tight and empty.

"Perfect timing, Nancy. If you continue to do it that well, I will let him give you a present with his mouth after," Miss Finny promised. "Take your middle and index fingers Nancy and push into his anal hole, pushing your fingers down you will feel a little lump in about three inches."

Nancy complied, and when her fingers pushed over the little knot, Jim moaned even louder, and the cock bounced again.

"Using your fingers or the milking rod, you push down and forward on the knot, then pull back to the entrance. You continue to do that until the flow of fluids stops for 10 minutes from the pee hole," Miss Finny told the two.

"You keep the cock hard, and he gets done quicker. If you keep the cage on or don't keep him aroused, it will take longer. The more you milk him, the quicker he will finish at each milking. He doesn't get built up in the prostate, and his body learns to respond to the milking," Miss Finny explained. "Now put the cup under his cock to catch the goo for him to drink."

Nancy liked the intimacy of feeling Jim's glands herself. She continued to use her fingers and only had to stroke the penis occasionally to keep him hard and aroused.

"Vivian, would you fetch me a tea with spearmint liqueur in it?" Miss Finny requested of her naked charge.

"Yes, Miss Finny." Vivian responded, quickly heading to the kitchen, where the tea pot was always hot.

Miss Finny enjoyed watching men submit almost as much as she enjoyed making women submit. Vivian returned with the tea, holding it on her palms with the handle to Miss Finny on her knees in front of the spinster. The hot porcelain was making Vivian's palms uncomfortable.

"Be a dear and crawl up under my skirt and work on keeping the sweat down in my crotch. It seems to be getting humid and moist down there." Miss Finny instructed Vivian, pulling her dress up and parting her legs as Miss Finny's ass slid to the front of the chair.

Vivian, not wanting a punishment, quickly put her head in the opening and followed the musky scent to its source.

"Slower child. This isn't a race. Just keep your mouth on my cunny and work your tongue. Yes, slurp that up. Oh, good girl, yes, right there. Just like that," Miss Finny instructed as she watched her redheaded maid milk the gland of her soon-to-be sissified husband.

By the time Nancy finished, Jim was vibrating every time she stroked his cock. The feeling of ache created by her fingers on his gland was both pleasant in creating need and arousal and unpleasant in that the need was never met and the arousal never abated.

Miss Finny had three orgasms on Vivian's face before she began to get sore from the licking and sucking of the blonde's mouth.

"Today is a Friday; Jim will be milked on Monday, Wednesday, and Friday nights after dinner. Tomorrow is a big day. Vivian, go get a moist, warm towel and clean up the mess you made on me with your face. Nancy, get some ice and shrink that cock back up. Cage Jim, and he can crawl out to the shed for the night after he drinks his discharge," Miss Finny ordered.

Once she was clean and Jim's cock was secured away, Miss Finny lifted the blindfold off him and untied the strappado on the armbinder. Miss Finny could smell the coconut oil and knew Jim would soon associate the smell with being milked and submissive.

"Nancy, you can kiss your husband good night and then I will take the binder off, no cheap feels for him." Miss Finny ordered.

Jim stood after being helped down from the table. Nancy grabbed the back of his head, locked her lips on his, and stuck her tongue passionately into his mouth.

"I love you!" Nancy told him, looking into his hazel eyes.

"I love you as well, we will get through this together." Jim told her.

"If you both mind and learn, you will stay together. If either of you rebels at all, I will send you separate ways," Miss Finney threatened.

The four had fallen into a routine going through the weekend. Each of the girls had two maid's outfits and their hobble wool, three pairs of boots, all ballet toes, and increasing heels (6", 8" and the 10"). The 10" might as well not have had the heel, as the foot was only 8 degrees lower at the heel than vertical.

The routine changed on the morning of Vivian's 7th day and Nancy's 8th day of retraining. A large SUV with oversize tires pulled to the front of the house and stopped in a cloud of dust early in the morning.

Vivian was scrubbing the porch on her hands and knees with a bucket of hot ammonia water. When she heard the loud exhaust pull off the main road a mile from the house and school. Jim heard it at the same time; he was trimming and shaping the hedges as he was the groundskeeper and handyman for the school now.

Vivian was about to go find Miss Finny when Miss Finny burst through the door, causing Vivian to drop to her knees again and continue her chores. While scrubbing, Vivian saw one of the most intimidating women; she remembered seeing her get out of the driver's door of the SUV.

The woman was young, very tall, over 6', and she had heels that pushed her up from there. She was in a tight red leather body suit with a built-in bone-stave corset. The corset accentuated the shape of the woman more than forcing the shape like Vivian's own corset. The red leather boots were laced up to mid-thigh and were form-fitted.

Vivian heard her command, "Ground and stay!"

The back passenger door opened, and a tall, dark-skinned man, slightly taller than the woman in her heels, stood barefoot. He tossed something back into the vehicle. Crawled out to the woman's feet and prostrated himself in the gravel flat with knees bent, heels to his ass, caged cock on the gravel. Same with his chest and face. Elbows out and hands on his shoulders.

It suddenly dawned on Vivian what the woman looked like with her kinky hair cut into a styled flat top. She looked like "Grace Jones" the 1990's rock singer. Same very skinny body, bigger breasts than Grace, and more hips, but the same dark skin, sharp-angled facial structure, and stylized hair.

Miss Finny had covered the distance from the house to the SUV while the man was getting into position.

"You must be Misty; I am Miss Finny. Welcome to the school. I am sure you will acclimate quickly. Would you like to come in for some tea?" Miss Finny offered.

"Ice water would be great, where does Ty put my stuff?" Misty asked.

Miss Finny pointed to a little house on the far side of the school grounds. "That was my house until the previous school year, when Marm passed, and I took this house. Your furnishings arrived last week, and I had them arranged by the movers the way I would have wanted, but you will obviously put them how you desire."

Miss Finny turned and passed Vivian, saying. "You continue your chores. Nancy will serve inside today. When this porch is finished, start on the back porch and keep that bucket hot; it looks like it has cooled considerably."

Vivian's hands were already irritated from dipping the brush into scalding water. Lucky for the protection of the latex shoulder gloves on her uniform. It did not help with the burning of the ammonia in her nostrils.

"You heard the woman? Get my stuff over to that house!" Misty ordered Ty.

Vivian assumed it was Ty, as the bright red ink across the man's shoulder blades was "Misty's Slut Ty," and below that was the female symbol of a circle with a T below it and a male symbol of a circle with an arrow out of it. Except the arrow was facing down at an angle and had prison bars around it.

From the back of the SUV, Misty saw him grab three suitcases and start across the expanse of grass. He crossed the quarter mile to the other house barefoot. Misty looked down at Vivian as she walked up on the porch.

"Servants are allowed. Nice. She even dresses them well." Heels clacking on the boards as she entered the house.

Nancy was in the bathroom, scrubbing down the already clean room with hot bleach water. Miss Finny kept a 55-gallon drum on a burner out the back door that the maids filled their buckets from. It was on a continuous low boil, and after filling a bucket, the girls would add water from the hose until the barrel boiled out the top.

"Nancy, get me a tea, Miss Misty a glass of ice and a pitcher of ice water." Miss Finny boomed to the bathroom.

Miss Finny heard scrambling sounds, so she knew Nancy had heard the instructions. Misty walked backward in time as she entered Miss Finny's domicile. The entry had a dressing bench and coat stand with hat hooks.

The entry gave way to a small parlor with three Edwardian armchairs with pale green upholstery. Each with its own tea table to the side. On the opposite side of the small coffee table was a settee or small couch. The walls had a chair rail with wainscoting below and a deep mahogany tongue and groove above. The dining room was separate, with an Edwardian armchair and tea table at the end of the room, near the two entrances at the same end.

Misty could not see into the kitchen, but she bet the décor was period-accurate, with a stove that looked like it should be burning coal or sod.

"Have a seat where you would like." Miss Finny said. "Nancy will be out momentarily with water and tea."

Nancy, knowing the tea was for Miss Finny but having no clue as to the ice water, brought the two glasses first. Nancy rushed out and set Miss Finny's cup of hot tea with a soaking spoon on the saucer next to the chair she was seated in. She then placed a coaster under the water and set it next to the severe-looking black woman seated in the next chair.

Nancy had bent forward to place both items, her large breasts dangled and swayed with her movement.

"Nancy, remind me after that you need a correction. I would think ten on each breast should remind you that company gets served first. You curtsy at the table before you serve," Miss Finny said sternly.

Nancy curtsied facing Miss Finny and lifted on a skirt that wouldn't lift. "Yes, Miss Finny."

Nancy hurried back to the kitchen to return with the pot of tea and the pitcher of ice water, setting each on a pad at the relevant table after curtsying for each woman. The severe woman first.

DirtBoss
DirtBoss
139 Followers
12