Miss Pamela nine

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Tommy's punishment takes a surprising turn.
3.4k words
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Part 11 of the 15 part series

Updated 01/17/2024
Created 08/18/2023
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Delicate fingers traced my cheek, awakening me gently. I must have fallen asleep as the burning abated in the darkened room. The feathery caress was followed by a delicate kiss.

"Wake up, Tommy"

Lisa's soft whisper complemented her touch perfectly.

"Miss Pamela sent me in to untie you."

She set about undoing Desiree's knots, lovingly massaging the welts the rope left. I realized she was as naked as i.

"Nice knots. You weren't going anywhere."

"I was expecting more punishment. You were right, Mistress is not pleased that we had sex."

"She told me."

"I thought it would be fine. She seemed to enjoy seeing us together last night. Big mistake."

She undid the last bond on my left ankle and handed the end of the rope to me.

"My turn. Tie me the same way."

I gave her a quizzical look accompanied by a scoffing laugh.

"I mean it, Miss Pamela is considering my offer."

"What was that?"

"I begged her to let me take your punishment."

"What?"

"You were fulfilling my fantasy. I should be punished for leading you astray."

"I'm a big boy. I can't let you suffer for my decision. You didn't hear me say no, did you?"

"I'm a big girl and I won't let you suffer for fulfilling my lifelong fantasy."

The door opened to reveal Desiree backlit dramatically.

"Mistress wants to see you, both."

She stepped back, opening our path to judgement. We exchanged a look that spoke of mutual support and strode bravely out to meet our fate.

"Present."

Lisa looked at my positioning and adapted quickly to copy me. Mistress regarded us sternly.

"My slave took it upon himself to take my property and give it to this horny slut. I am not usually a proponent of utilizing corporal punishment for discipline. It complicates matters that Tommy is my committed slave and needs to understand that he is no longer a freelancer sexually, and while he and Lisa were together with my blessing last night, he indulged again without my knowledge again today."

She paused for effect, again sternly glaring at us. Lisa fidgeted and I braced myself for whatever Mistress was building up to.

"Were you prepared to be punished, Tommy?"

"Yes, Mistress?"

"Did you deserve it?"

"Yes, Mistress."

"Do you have any excuse for giving my property to Lisa?"

"No, Mistress."

"That pleases me. There's a phrase I find apropos, 'Excuses are like assholes, everyone has one and they all stink.'"

"Except after a peppermint soap enema," Desiree wisecracked.

Mistress cocked an eyebrow gave her a wry smile.

"I had planned further suffering for Tommy to ensure he understood that his sexuality belongs to me. Desiree is well versed in certain aspects of our chosen lifestyle because of her history with her former Mistress. So, I planned to let her demonstrate specifically that my property must only be used with my approval, or those whom I grant permission."

I averted my eyes submissively.

"Tommy, who has permission to use you?"

"You and Miss Desiree, Mistress."

"Do you deserve punishment for assuming sex with Lisa was permitted?"

"Yes, Mistress."

"Was it worth suffering for?"

"Yes, Mistress."

From the corner of my eye Lisa's smile brought a matching one to my lips too.

"Do you wish that she had license to use you sexually?"

"Yes, Mistress."

"Do you know that she has offered to accept your punishment in your place?"

"She told me, Mistress."

"She must feel strongly about you."

"We have bonded quickly, Mistress."

"How would you feel about her being punished?"

"I decided to fuck her, Mistress and the punishment is for me. She didn't owe you obedience, I did."

"Lisa?"

"It was a specific fantasy for me, Ma'am."

"We've gotten to know you quickly, Lisa. I enjoy your delicious slutty horniness and hope that we continue to play together."

"Oh, I do too, Ma'am." She radiated genuine eagerness.

"Would you like to be my slave?"

"Yes, Ma'am."

"I'm inclined to allow you to stand in for Tommy and accept his punishment. Do you still wish that."

"Yes, Ma'am."

"You realize that it will really hurt?"

"Yes, Ma'am."

"Very well. Desiree, are all materials ready?"

"Yes, Mistress."

"We will begin with a thorough flogging. I think it will be particularly amusing if it's administered by Tommy."

Desi handed me the slender tressed flogger from her shop.

"Lisa, you will maintain your position while Tommy beats you, shoulders down."

"Yes, Miss Pamela."

"Have at her, Tommy."

I whispered to her as I stroked her skin before beginning, "You're sure?"

She nodded, thin lipped, trembling slightly.

Beginning high on her back, I used a figure eight pattern working up and down her back, watching her skin redden gradually.

"Get your back into it, Tommy. Work her hard."

I acknowledged Mistress with a grim nod and increased the force of the strokes. Now Lisa began to whimper each time the leather bit into her skin.

I moved my focus to her firm, haughty butt cheeks. First, I used the tips to inflict stinging bites and followed those with broader strokes with the full strands. Soon her ass was glowing bright red, and I moved down to her legs.

Lisa was enduring her punishment stoically for the most part, although when I caught tender inner thigh flesh, she whimpered more and even yelped at a couple that landed high, close to her holes.

When she was well reddened, ankles to shoulders, Mistress nodded, "Time for her front, Tommy. Spread your legs a bit more, my dear."

Lisa took a deep breath, widened her stance and held her head high. She looked into my eyes, smiled grimly and nodded. I was pretty sure she had never been beaten like this and tried to show my admiration and affection in the smile I returned. She raised her head proudly and thrust her breasts out, inviting the leather's harsh caress.

I was gentle with the first strokes on her breasts, allowing her to warm up and acclimatize before increasing the tempo of tips biting into her tender flesh, then applying broader strokes with full impact. She did her best to remain stoical, but a tear rolled down her cheek when I caught her nipples with a firm stroke and her thighs trembled.

I moved down to her taught belly and Mistress interrupted, jingling a pair of clovers wordlessly. I took her meaning and held the flogger handle up to Lisa's lips. She accepted it, taking it in her teeth.

I took the clovers from Mistress and approached Lisa. She stared at them apprehensively. I bent forward, bringing my lips to her right nipple. It was swollen, erect, and aching for attention so I seized it in my lips suckled it aggressively and teased it with my tongue. It grew even fatter under suction, so I released it and let a clover close aggressively on it, biting hard into the tender swollen flesh. Lisa cried out, unable to maintain against the shocking pain.

I moved to her left nipple and recreated the sequence, eliciting a heartfelt scream of anguish this time. I stroked her cheek and kissed her tenderly. Gasping for breath as she tried to compose herself, she managed to whisper, "I love you, Master."

This caught me by surprise, but it felt incredible to have her react this way. I stood back for a moment appraising her in this new light.

I reached between her legs and stroked her puffy lips, separated them with my index and ring fingers, opening her to my middle finger. She was wetter than I expected, and my finger slipped smoothly into her before I brought it up to manipulate her pearl. Her shuddering response was both surprising and gratifying.

I took the flogger handle from her teeth gently and stepped back to establish the correct distance and began spinning the tresses in a vertical plane. I saw Lisa gulping deep breaths, preparing for what she expected to come.

She shrieked at the first impact of leather against pussy lips and continued moaning as repeated strikes landed in its wake. Her knees buckled under the relentless pain. I slowed the pace to allow her time to gain control and shifted my focus to her belly and upper thighs for a series of strokes.

When it seemed as if she'd regained her composure, I returned my attention to her pussy. She maintained an even keel now, actually appearing to welcome the leather's sting, so I increased both force and tempo. She thrust her pelvis forward shocking me at the appearance of arousal and eager desire for the whip. Shockingly her arousal seemed to increase, and we were all astounded when it was obvious that she orgasmed, knees bending, crying out in ecstasy and shuddering with pleasure.

I stood back from her now prostrate form curled at my feet on the carpet, then knelt next to her so I could stroke her gently. She practically purred at my touch.

"That was surprising," Mistress commented and Desiree nodded, joining me on the carpet next to Lisa.

"Didn't seem like punishment to her."

I laughed and agreed, "Pretty far from it."

Lisa murmured what sounded like "thank you."

Mistress approached us, looking down, smiling archly.

"I think she might be an interesting addition."

Desi and I nodded in rough unison.

Mistress squatted and reached out to take one of the clovers still pinching her breast and twisted it, drawing a plaintive mewl from Lisa.

"What do you think, dear heart? Would you like to become my slave?"

"Yes, please. I do love playing with you all."

"There will probably be pain that you find less pleasurable than tonight."

"Yes, Ma'am."

"Desiree, make her a collar."

"Yes Mistress. Should all three match?"

"Yes."

"I'll begin tomorrow."

"Then we have the matter of punishment to be completed. So far pleasure has intruded surprisingly. I doubt Tommy would have cum from being flogged between his legs."

"Unlikely, Mistress," Desi tried to suppress any sign of amusement. I tried to vanish.

"You were planning to use some of your former Mistress' techniques weren't you, Desi?"

"Yes, Mistress."

"It will be a more exact replication with Lisa as the subject, won't it?"

"It will, Mistress."

"Probably less pleasant than the flogging too."

"Definitely.

"Best if she is bound?"

"Yes, Mistress, we don't want her moving."

"Tommy, bind her the way Desi bound you."

"Yes, Mistress."

I led Lisa back to the bedroom by the clovers chain. She cried out as the clips tightened further with the pressure. I yanked the chain with each step, eliciting delicious yelps. By the time she was positioned face up on the bed she was emitting a steady stream of whimpers.

"They really hurt."

"I know baby. You did volunteer to take this punishment."

"For you."

"Desiree is going to hurt you now. If you choose to become Mistress' slave, it will not be the only time."

"I know.

"When I was beating your pussy, you called me Master."

"I did."

"Is that something you want?"

She nodded wordlessly despite a hint of fear in her eyes. I tied her wrists as Desiree had tied mine, clove hitches with half hitches to lock them. Her arms were spread wide, leaving her upper body totally vulnerable, offered for any liberties. I kissed her tenderly, stroked her hair and smiled encouragement.

As I began to secure her first ankle Desi entered the room carrying a spreader bar.

"Use this on her legs, then secure it to the ropes. It'll hold her steadier."

Desi returned to the living room while I secured her ankles in the cuffs at the ends of the bar then tied it off, stretching her fully. I stroked her thighs to calm her and ease her into this captivity. With her legs widespread and stretched in offering, her swollen pussy lips were offered obscenely, but beautifully. I leaned over and kissed them tenderly. She moaned.

Desi returned carrying a small bag which she lay on the bedside table. She withdrew a penis ga and handed it to me.

"We don't want her screams to scare the horses."

A flash of terror illuminated Lisa's eyes as I reached toward her face with the gag in hand.

"Open."

She obeyed, grudgingly opening her mouth to allow me to slip the four-inch cock into her pretty mouth.

"It'll give you something to bite down on when it really hurts."

She nodded, unsure and fearful, accepting the short dildo awkwardly. I adjusted the straps, so it fit her as comfortably as possible. After all, she was accepting the punishment in my place.

Mistress entered the room, pulled the armchair from the corner to a spot near the bed. Desi began unpacking items from the bag. She lay them out on the table. Lisa's eyes widened and she trembled slightly when she saw the package of hypodermic needles that Desi set down next to the betadine.

Desi pulled on a pair of nitrile gloves. Mistress gestured for me to assume my position at her feet. I knelt where she had indicated. I could feel Lisa's fear and smell the intoxicating aroma of Mistress' arousal.

Desi separated Lisa's puffy pussy lips, teasing them open and pulling on them with both hands.

"My ex-Mistress loved to play with needles. She particularly enjoyed needling my pussy and clit. It gave her great pleasure to inflict pain on me like this. In fact, she was planning to infibulate me. Do you know what that means?"

Lisa shook her head, panic in her eyes.

"She was planning to sew me shut. That would be fitting for you taking Mistress' property in your wicked twat, wouldn't it?"

It sounded as if Lisa's mumbled response around the penis gag might have been, "please don't.'

"Don't worry, sweet slut, I won't be doing that...this time."

Mistress grabbed me by the ears and pulled my face into her soaking pussy.

"Get that mouth to work."

I needed no encouragement and happily began digging into my favorite repast. Mistress was extremely aroused, hot, wet, and eager for my tongue. Her clit had fully emerged from under her hood, and she responded immediately with deep moans when my tongued bathed it in loving caresses. She raised my head and turned me so i could see the action on the bed.

Desi wiped down Lisa's labia with a betadine-soaked cotton ball, making her shiver from a combination of the cool liquid and anticipation of what was to follow. She took firm hold of Lisa's left lip and stretched it away from her vulva, then brought a needle to bear. With a firm thrust, she skewered Lisa's labia. Lisa responded with a scream muted by the gag. Mistress shuddered and pulled my mouth back to her sodden sex.

When Desiree repeated the routine and slipped another needle through Lisa's other curtain, Mistress urged me to eat her aggressively with a stroke of the flogger down my back and she came forcefully grinding my mouth into her sodden slit.

"You, okay?" Desi asked Lisa solicitously, stroking her brow.

She answered with a whimper and a nod.

"Good girl"

Desi massaged her clit, coaxing it out of hiding, making Lisa moan her pleasure at the attention. She took a fresh cotton ball doused in betadine and swabbed the proud pearl. Mistress prodded me back into position where I could view the action. Desi pinched deep into Lisa's flesh pushing the clit out prominently, then brought the tip of another needle up to touch the side of her pink button. Lisa was gulping shallow breaths, Desi smiled wickedly, and Mistress breathed deeply.

With firm, steady pressure Desi slid the needle through Lisa's clit. Her scream was muffled by the rubber cock in her mouth, but it was anguished and spoke of the intense pain she was surely feeling.

Mistress grabbed a handful of my hair and pulled my face back between her legs. She came almost immediately as I established suction and tongue friction on her swollen clit. She clutched me so intently that my nose was mashed forcefully against her pelvic bone.

I could hear Lisa whimpering plaintively and Desi consoling her as Mistress shuddered in her orgasmic aftershocks. My rigid cock dripped precum in its aching need for release.

"Tommy, present."

"Yes, Mistress." I rose to my feet and turned to face her.

"Present to Desiree."

I turned to face Desi. I was in the expected position with my hands behind my head, feet spread, and engorged cock thrust forward invitingly. She turned her attention to me, leaving Lisa writhing and moaning on the bed.

"Mistress and I think it's only fair for you to get a taste of your own punishment."

She turned back to Lisa and slid the penis gag from her mouth.

"Don't you agree, my dear?"

Lisa nodded but shot me an apologetic look.

"What do you think, Mistress? Frenum."

"Mmm, perfect."

"Turn so everyone has a good view."

I obliged and turned as my erection began to wilt.

"Less erotic when the needle is coming for you, isn't it?"

When I failed to respond she arched an eyebrow, "Well?"

"I guess so, Ma'am."

She cupped my balls with her right hand and surrounded my cock with her left, stroking and caressing me back to full tumescence.

"It will make for better viewing nice and hard."

After swabbing the intended area with betadine, she pinched the flesh below the groove in my corona so the frenum puffed out and brought a needle to bear. She placed the point against my flesh.

"Stay still or it will probably be much more painful."

My fight or flight reflex was screaming as I presented my cock for her needle.

"Araggh." the needle punched through my tender skin.

Mistress licked her lips lasciviously, Desi chuckled wickedly, and Lisa looked away.

"That was a taste of your own medicine. There would have been more if Lisa hadn't taken it for you. You should thank her."

"Thank you, Lisa."

"Remove her needles and the clovers."

"Yes, Mistress."

Lisa shrieked as I expected she would when I released the clovers from her nipples. When I slid the needles out of her labia she sighed, but she did cry out when I slid the needle out of her clit.

"You should clean the wounds with betadine."

"Yes, Ma'am."

Desi handed me the bottle and a cotton ball. I used them to clean the punctures. Lisa winced from the sting.

"You were very brave, baby. Thank you for your courage."

"You're welcome, Tommy, I love you."

"i love you too," I took her in my arms and kissed her tenderly.

"Ah, young love," Mistress chuckled sarcastically.

"Mistress wanted you to love me." Desi did a mock pout.

"I have room in my heart for you too."

"I don't want to be the other woman, slut."

I hung my head, chagrinned.

Desiree let it play for a minute before cracking up, "Gotcha."

Mistress joined in on the hilarity at my expense. Lisa and I eventually joined in.

"Lisa, are you still interested in becoming my slave and joining our little family?"

"Yes, Miss Lisa, please."

"I think you have earned your position. Desiree will be making matching collars for all three of you. And you may now call me, Mistress."

"Thank you, Mistress."

"You're welcome, dear heart. Tommy, release her from her bonds so she can come show me her gratitude."

I untied the ropes and opened the ankle cuffs, freeing Lisa to go to Mistress. Despite her stiffness from the bondage, she quickly assumed a kneeling position and began worshipping Mistress lovely red-haired pussy. She worked assiduously to demonstrate her devotion quickly bringing delighted moans from Mistress. Desiree grabbed me by the balls and pulled me to the bed where she pushed me face first between her legs. I found her very wet and eager for me to satisfy the passion she had built by torturing Lisa.

Before they had both been fully satisfied, I'd eaten Desiree to three shattering orgasms and so had Lisa for Mistress. Both of our faces glistened with the silky secretions we were bathed in. Desiree lay back on the bed, luxuriating in her afterglow and Mistress stroked Lisa's hair, smiling and purring.

"You are delicious, little one. I'm going to enjoy owning you, aren't I?"

"I hope so, Mistress. I'm very eager to please you."

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