Mrs. McGregor's Tawse Ch. 06

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Stuart's training intensifies.
3.3k words
4.43
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Part 6 of the 22 part series

Updated 06/11/2023
Created 01/02/2022
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MarkKane
MarkKane
66 Followers

CHAPTER 6

Stuart was wearing a collar, wrist and ankle cuffs. Mrs. McGregor took a chain attached to the head of the bed and locked it on the collar. Then she took a black leather cock ring and buckled it around the base of his cock and balls. She then took a length of chain and padlocked it onto the D ring on his collar, then did the same to the cock ring. Next she snapped clips onto his wrist cuffs and attached them to the chain, so his hands were positioned at chest level.

Then she ran a length of chain from the bottom of the bed to his ankle cuffs, through the d-rings on the cuffs, back to the bottom of the bed then used a clip to attach it to the base of the bed. She left some slack in the ankle chain so he could change position.

Mrs. McGregor put on latex gloves after she chained Stuart down. She lubed the gloves up then started playing with Stuart's cock. He became erect immediately.

She then ordered him onto his stomach. Stuart struggled but eventually turned over. Mrs. McGregor then poured a generous dollop of lubricant into his ass crack. She spread the lubricant around, then shoved a gloved finger into him. Stuart grunted in a surprised reaction. Mrs. McGregor ran her fingers in and out, then penetrated him with two fingers.

Then she picked up a butt plug, lubed it up and slowly forced it into Stuarts anus. He was begging for her to stop, but she ignored his pleas. The wide part of the plug finally entered his ass, and just the flared base showed.

"I really don't like doing this to you Stuart, but I don't want you playing with yourself during the night. Young boys under my tuition aren't allowed to play with themselves. It's a disgusting habit, and you will no longer touch yourself without permission. And the plug stays in all night."

She left the room and turned off the lights. Stuart sighed in contentment.

The following night Mrs. McGregor put Stuart into the same bondage for the night, including a butt plug, but then turned him over. She reached up under her skirt and snaked her panties off and then placed the crotch over his face. Her rich aroma triggered his lust, causing an immediate erection. Mrs. McGregor gave a wicked smile as she started toying with his erection. Soon he gave all the indications of an imminent orgasm, and she stopped stroking him. She stood up, went to the door, and turned off the lights. "Goodnight, little one. Pleasant dreams."

Stuart groaned in frustration.

---

It was a quiet evening in the Duncan household. Stuart lay blindfolded on the floor in front of his stepmother as she ran her stockinged feet over his erection.

"Stewart, what is your favorite fantasy? " Mrs. McGregor asked.

Stewart hesitated. Then he said "I like to think about how you make you, you know....errrr....lick you. And when you make me sniff your panties. Sometimes I think about the first time Governess used the tawse on me. And....well... a couple other things."

"Does thinking about sucking another slave's cock until he came in your mouth get you excited?"

Stewart blushed. Then in a tiny voice he whispered "Yes, Maam."

"Do you like it when I masturbate you?"

"Yes Mommy. Both you and Mrs. McGregor."

"Which do you like more, when I make you cum and then spank you or spanking first, then waking?"

"Stuart blushed and said "First the spanking."

"Would you like me to do that to you now?"

Stuart whispered, "Yes, Mommy."

"Very well, run to my room and fetch my leather opera gloves, then bring them here."

Thirty minutes later, Stuart's face was flushed and red from bawling, and he was licking his own cum from the palm Mommy 's glove.

---

Maid May was sent to fetch Stuart from his room.

When he arrived in the sitting room his stepmother and Mrs. McGregor were waiting for him.

"I thought that today I would introduce your son to some rope bondage. I adore Japanese style bondage. I'll start with a basic rope harness. It frames the torso very neatly, and can be the start of much more advanced techniques."

She started with a long rope and started decorating Stuart. "Oh, this is fun." Margaret said. She put a knot in the rope and snugged it against his rear entrance. When she was finished Stuart wore a weaving of rope from his neck, down through his crotch and up his back, weaving back and forth. Then she wrapped a doubled length of rope around his shoulders, then bound his arms with the remaining rope in the middle of his back.

Then she looped a rope above his knee and ran it through an eyebolt in the ceiling. she pulled the rope, forcing his leg into air. Then she tied it off and left him like that. The two women ignored the bound boy, even after he started moaning in discomfort.

Finally Mommy looked up and rang her hand bell. When May appeared, she order Stuart to be gagged. May reached up under her skirt and removed her panties, then stuffed them into Stuart's mouth, then wrapped a length of rope around his head to maintain the gag.

After an hour, Mommy called May back to the room.

" May, run to the Mistress Chapel and fetch a flogger. I want you to thrash Stuart."

Two hours later he was finally released.

---

Mrs. McGregor wearing a black leather skirt, seamed stocking and stiletto black patent mules. "You will be cleaning my shoes today. For an hour. And if your work is unsatisfactory, you will receive a spanking, then twelve with the tawse. You may begin."

At the end of the hour, she examined her shoes.

"Nose on the floor. Hands behind your back."

She pulled on her black latex opera length gloves.

"Completely unsatisfactory. Over my lap. And in twenty minutes you can clean my shoes again. THEN you get your tawsing."

---

Mrs. McGregor entered Stuart's room.

She was naked except for her black opera lenth gloves.

"Spanky time, Stuart. Over my knee."

---

Mommy and Mrs. Stewart were deep in conversation one day.

Mrs. McGregor said "I think it's time to increase his training."

Mommy chuckled. Yes, he is quite infatuated with you at this point. Do you think you can make him even more submissive and obedient?"

"Of course, dear. Remember, I've been doing this for a long time. I increase the degradation and humiliation, and his adoration just increases. He'll do anything for me. And remember, the next step is to feminize him."

---

Stuart had never really got used to being naked around the house. Mrs. McGregor were constantly summoning him with a hand bell, then having him perform some minor chore.

"Stuart, run to the kitchen and get me a cup of tea."

"Stuart, run to the sitting room and fetch me the latest issue of Vogue."

"Stuart, do you think the seams on my stockings are straight?"

Of course the other thing the she liked to do was to either make him erect and leave him frustrated or force him to orgasm.

Of course the reason for this was to deepen his devotion to his Governess.

"Stuart run to the cellar and get a new bottle of Chablis. Serve me in the living room."

---

Mommy and Mrs. McGregor summoned Stuart.

"Spanky time, Stuart. Over my lap."

Stuart's eyes widened in fear.

When Mrs. McGregor was finished, it was Mommy's turn.

---

Mrs. McGregor became more and more demanding.

"Stuart, come with me, I have to use the bathroom. You may crawl."

Stuart got down on his hands and knees and followed her to the bathroom.

"Stay on your knees. Watch."

She lifted her skirt, lowered her panties and sat.

"Watch I said"

Stuart started intently as she released her water.

It slowed to a trickle, then stopped..

"Very well, you may lick me clean."

She thrust her hips forward, giving him access. She sighed and gave a little shudder as she had a small orgasm.

"There's a hand towel on the sink. Fetch it and pat me dry."

---

"Stuart, I want you to learn this."

She handed him a piece of paper with the following:

'I am your slave.

You own me.

I am your property.

I submit myself to you.

I serve you.

You possess my mind, my body and my soul.'

"You will memorize it and the first time you see me in the day, you are to go to your knees, kiss the toes of my shoes and repeat this litany."

---

Stuart waiting on Mrs. McGregor in the bathroom, kneeling, head down because he's not allowed to look at his Governess while she's in the tub, arms out holding her towel. She lifts a foot to the edge of the tub, then gives a one word command: "Suck"

---

Mrs. McGregor then started a regimen of tease and denial.

Stuart was used to his Governess masturbating him to orgasm.

Today she had started, got him nice and erect and almost ready to cum.

"Ok, that's enough. You can go back to your chores, Stuart."

"But...but... but....Mrs. McGregor...." he whined.

"QUIET. Do you want a nice long session over my lap? No? Then go do as you were told."

---

Mommy rang her hand bell.

Maid May entered the room and curtseyed.

"Ah, May, perfect. You win today's lottery. Report to me at bedtime."

"As usual, Mistress?"

"Yes, just your collar and leash. And you may wear heels."

"Thank you Mistress. I look forward to it."

That night Maid May learned that Mrs. McGregor was a mistress of the cane as well as the tawse.

Three days later Maid May's hindquarters were still striped from the caning she received that night.

---

Vanna rang the handbell. When Stuart came into the room she said,

"Now, slave, I want you to kneel down and worship my pussy. Do a good job, or I'll punish you. Understand, slave?"

"Yes, Mistress."

"Then don't stand there you idiot, get started."

He dropped to his knees and started licking his Mistress.

Later, Mistress said "Ah, slave, you have a lot to learn. That was totally unsatisfactory. I'm going to have to punish you, and then you will do it again."

"But....."

"Be quiet, slave. You forget your place, and you forgot the rules. That makes it a triple punishment.Now, go into the drawer of the nightstand. My cane is there. I wish to use on your naughty bottom."

He fetched the cane and held it out to her.

"No, slave, you must present it to me properly. Kneel and hold it out to me on your palms."

"Now ask me to punish you."

"Please, Mommy, please punish me."

"Very good. Now, for this punishment, you are to count each stroke, and thank me. Do you understand, Stuart?"

She stood and walked around him. "Stay there" she said.

She left the room and returned, and placed a blindfold over his eyes.

"Hands behind your head. Maintain that position until I return."

He didn't know how long he waited, 10, 15, 20 minutes for Mistress to return.

He was startled when the door opened and she reentered the bedroom.

"Let's see, since this is the beginning of your training, I'll be gentle with you. Your disobedience will cost you 10 strokes."

"Thank you, Mistress."

"For each infraction."

"Wha...?"

"Three infractions times 10 strokes makes 30. Understand, slave?"

"Yes, Mistress."

"And remember, I want a count. With each cut, you are to thank me and count the stroke."

"Yes, Mistress."

"And one more thing. If you lose count for any reason the counter goes back to one. Understand?"

"Yes, Mistress."

Swack.

"One. Thank you Mistress."

Crack

"Two. Thank you Mistress."

Two stripes showed on the slaves rear.

Swish.

"Three. Thank you mistress."

Smack!

"UH! ahhh!! AHHHHHHH!!! Thirty.....Thank you, Mistress."

She caressed his asscheeks, feeling the warmth she had inflicted on him.

"Good. Come with me."

Grabbing him by the arm, Mistress walked to a corner of the room.

His rear was red and covered with stripes.

"Hands behind your head. Stay here until I tell you to move."

She caressed his semi-erect cock, making him harder and harder.

"I see your punishment has gotten you all excited, hasn't it, slave?"

"Yes, Mistress."

"But remember, this"...as she squeezed his erection...."belongs to me, doesn't it, slave?"

"Yes, Mistress."

Again he had no sense of time. It seemed forever as he waited for Mistress to give him another order. He waited, his rear seemingly on fire, his cock semi-erect.

He sensed that she was beside him, felt her caressing him, penis, then balls, then his throbbing, sore ass.

She hooked a leash onto his collar and pulled on it.

"Come with me, and we'll see if you learned your lesson. Kneel."

He knelt down, and Mistress pulled him by his leash toward her waiting pussy.

Mommy came under Stuart's ministrations. After she recovered her breath she had him lay on the floor, straddled his face and made him give her another orgasm.

When she was finished she left him laying there, face coved with her juices.

---

Mommy rang the handbell beside her bed, and maid May responded.

May entered the room and found Mommy and Mrs. McGregor lying on the bed together.

"May, I want you to go the Stuart's room, release him from his chains and bring him here."

May returned to Mama's room with Stuart on a leash, crawling on all fours. He was still wearing his slave collar and cuffs.

Mama smiled.

"Look in the bottom drawer of the dresser, you'll find what you need to bind him to the bedposts."

She pulled out four short chains and sets of snap hooks.

May snapped her fingers and Stuart stood. "Here, attach these to your cuffs."

Stuart put the chains on his wrists and ankles.

May snapped her fingers again and gestured. Stuart stood at the foot of the bed. There were restraint rings already screwed into the bed's posts, and May attached his wrists and ankles to them, spread-eagling him.

"May, could you gag him for me? I don't want to hear his whining. And here, take his chastity tube off. And I want you to come back in about an hour. You may change out of your uniform and get ready for bed. Oh, and bring a paddle with you."

"May, one more thing, please. There's a pair of nipple clamps on the dresser. Put them on him."

"Yes, Madame." She was smiling as she left the room.

After May left Mommy and Mrs. McGregor start making love to one another. Mama puts on a strapon and takes Mrs. McGregor. After Margaret's orgasm she stood then removed the ball gag from around Stuart's head. Climbing back onto the bed then she stands and thrusts the dildo into Stuart's mouth.

"Give it a thorough cleaning, boy."

Upon May's return, wearing a sheer blue babydoll nightgown and silken g-string, carrying a ping-pong paddle, she's instructed by Mama to alternate between stroking his erect penis and smacking him on the ass with the paddle.

She starts with his cock, caressing his already rock hard erection and balls. then she slapped his several times on the butt. she started alternating between front and back, giving the same number of strokes and slaps. Five tugs, the five hits, seven tugs, seven hits, ten tugs then ten smacks with the wooden paddle.

Mommy and Mrs. McGregor lay on the bed propped up on pillows, arms around each other, smiling at this superb demonstration of the art of the dominatrix.

Stuart, of course, was sobbing at the pain, alternating between thrusting his hips forward to avoid May's blows while begging for her to stop, then thrusting his hips while being stroked, begging for relief.

Mommy whispered to Mrs. McGregor "This is getting me turned on again" then started caressing her nipples.

"Yes, it is lovely, isn't it?"

"May, that's enough, dear. Please put her gag on again. Then come here and stand beside us."

She left Stuart sobbing, his ass a blaze of red.

"VERY good, dear. I bet that doing that turned you on as much as it turned the two of us."

"Yes, Madame."

"Let's see. Remove your panties."

May slithered out of the silken wisp. She, too, was denuded of pubic hair.

"Move closer dear, Legs apart, hands behind your head."

May obeyed her mistress.

Mama ran her finger up the maids vagina.

"Oh my. You are just sopping. Let's do something about that."

She pulled open a drawer in the nightstand and pulled out a small vibrator, turned it on and stated running it up and down her pussy. May had an ecstatic look on her face, as she started having an orgasm. But she was so well trained that she kept her position, upright, hands locked behind her head, although she was moaning and whimpering.

Mommy finished and dismissed May, giving her permission to masturbate if she wished.

"And May, before you leave, drape your panties over Stuart's head."

May carefully covered Stuart's face, making sure the crotch of the panties was at his nose and that he could still see through the leg holes. Then got on her knees and bowed, then kissed Mommy 's feet, and left the room.

Mrs. McGregor asked about Stuart.

Mommy said "Leave him. He's not going anywhere. Now, where were we?" and turned the vibrator on again.

Stuart, bound and gagged, whimpered in frustration.

He had had to witness the two women he adored making love, and then they rolled over and fell asleep, ignoring him and his raging erection.

Two hours later Maid May quietly entered the room, released and led Stuart back to his room, where she chained him onto his bed again.

---

Mrs. McGregor binds Stuart's hands behind his back. Mommy is laying on the bed, corseted and stockinged. Stuart is forced to his knees beside the bed and Mama positions herself in front of him, face down. She edges backward until her legs are over his shoulders, and Mrs. McGregor reaches down and spreads her asscheeks apart. Then she says one word: "Lick."

---

In the kitchen, with Stuart standing in front of Mrs. McGregor as she started to caresses him, causing him to erect. She has him turn sideways to her, as she continues her manipulations. she stats to caress his buttocks, running her fingers up and down the crease. Suddenly she uses one finger to penetrate him.

"Oooo...ooo....oooo.....Governess" Stuart cried.

Mrs. McGregor continued stimulating the boy, while he moaned in a combination of pleasure and pain. He started thrusting his hips back and forth, and the Governess felt his penis throbbing. His breathing had become heavier and more labored, his body trembling.

"Here we go" she thought to herself.

She increased the pace of her strokes and Stuart's body stiffened.

"Arrggg...." he yelled as pulse after pulse of semen was released from his erection onto the tiled floor.

His orgasm finally ended, a last few drips of cum sliding down his semi-erect cock.

Mrs. McGregor turned her charge to face her again, still holding him. She gathered the drops of cum on her fingers and had Stuart lick her hand clean.

"My goodness, child, look at the mess on the floor. Down on your hands and knees. Lick your cummies up."

Stuart obediently fell to his knees and started lapping at the puddles on the tiles.

"Another step deeper into subservience." she thought to herself, as she admired the boys ass sticking up, his penis and balls hanging down, as he licked the floor.

MarkKane
MarkKane
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thekeenreaderthekeenreaderabout 2 years ago

He is totally broken isn't he. No resistance now despite being humiliated and scandalised every waking hour

AnonymousAnonymousover 2 years ago

in summary, Then...

then.... then..... then.... then..... then... then....

If the evens described are in chronological order, perhaps most or all of the "then" words could be eliminated? Try it without the extra unnecessary words.

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