Boss Lady Pt. 02


Apologies for name confusion in part 1. In the earlier part of the story, the character Grant is sometimes mistakenly referred to as Clark.


I turned a lamp on in Ms. Jenna’s room and looked around. On the walls were portraits, photographs mostly, of remarkable women in history. Athletes, academics, scientists, all proudly displayed. And above the bed was a painting of Ms. Jenna wearing a tight leather outfit, looking down on a male who was on his knees beside her. His was the only image of a male in the room. He wore a collar, and Ms. Jenna held a leash which was connected to it.

Mindful of the time, I rushed to the closet and found the belt hanging there. It was apparently one used strictly for whipping, as it had no fashion value that I could see. The leather was dark and supple. I I held it in my hands and braved a quick kiss before placing it on the bed. I disrobed, neatly folded my clothes, and put them aside. I knelt in the center of the room, my heart beating quickly. Ms. Jenna’s footsteps approached.

She entered the room, and switched on an overhead light. She gave a brief once-over to my body, her face registering no impression. I have a good physique. I don’t do much to keep it that way – just how I’m built. I’m hairy-chested and have just a bit of a belly.

“I see you have an erection, Tim. Why don’t you tell me why that is.” she said, then laughed. “Oh! Don’t worry. I won’t slap your face. You haven’t done anything wrong. Okay? Just tell me what…moves you to be in this,” and here she gave my stiff penis a good look, “condition.”

“I was excited being near you, Ma’am.” I began hurriedly. “And then when I saw more of your beautiful body, well, I felt such desire.”

“Desire for what?” Ms. Jenna shot back.

“To be good and to serve you, Ma’am.” I said, and my penis hardened still more.

“You have a small cock, Tim. It’s definitely below average. Are you envious of well-endowed men?”

“I am, Ma’am. When I see a big cock in a locker room, I think of the power that man has, swinging a big dick between his legs.”

“Good, Tim. I’m glad you’re being forthright.”

“I cannot hide from you, Ms. Jenna.”

“That’s right. Somebody needs to know the details of your debased and cowardly life. We have much work to do, my boy! Continue about your wish to have a large penis.”

“Well, Ma’am” I began, “it’s just that women will find out who has a big one, then they tell each other about it, and then… and then… fucking Prince Charming has sluts lined up to service him!”

“But nobody wants your little wee wee? Is that the problem, Timmy?”

“I’m sorry I said ‘slut’, Ms. Jenna. I’m sorry.” Tears formed in my eyes.

“For today, it’s fine. We need to see what’s going on in that perverted head of yours!

So,” she continued. “You desire women and yet you can’t get any of them to take an interest in you. Is that because of your small appendage?”

“Partly, I guess.” I said, my head hung in shame. “But lots of times, before they get a chance to see it, they turn on me. They don’t think I’m good enough. Sometimes they laugh behind my back – with other women. Jesus! It makes me so mad!”

“So, because they’re not interested in you, and because they find sexual fulfillment with better-equipped men, you take it out on them.”

“I don’t mean to!” I blurted.” I just get so mad!”

“You’re gaziantep escort mad at women who make the very reasonable choice of being fucked by a man with an adequate cock. Let me tell you something, Tim. I hope every one of those women who rejected you curses you while they get their pussies pounded by a capable man. What might they say? I’ll tell you.”

1) ‘Glad I got that loser Tim behind me. What a creep! God, Jeff is going so deep!’

2) ‘Mmmmmm.This sure takes my mind off that pompous asshole,…Jim…or was it Tim? Anyway, the loser asshole I just dumped. Just so fucking weird!’

3) ‘Oh, God! This is some really nice dick I got in me. Jeez! By all means, pump away, Mister Dong! Fuck yeah! And eat your heart out, Tim!, you incompetent weasel!’

“That’s what they probably are saying, Ma’am.” I said, hearing the awful truth in these words.

“You’re not surprised, are you?”

“Women don’t like me. They don’t trust me.”

“I’m sure you’re right.” Ms. Jenna readily affirmed. ” Women deserve better than what you offer, believe me. Every one of them. I’m sure you’re aware of (though foolishly unconcerned with) the plight of Women today. They are abused and rendered powerless in vast parts of the world. You, Tim, wielded an unfair advantage in the workplace, buying into the subtle machismo of the corporation, buying into the

male-superior construct of a male-controlled world and… hiding behind it.”

My sin had been read out to me in these closing words Ms. Jenna spoke. Hiding; false bravado; smug chauvinism. And there was weakness running right under this tawdry veneer. Sure, I had the trappings of success, of stability. I had a very decent job, I had prestige. But these were unearned distinctions. I knew plenty of Women who could easily have disarmed me in debate, or dominated me in a board game of one kind or another, and yet were wasting their lives as coffee and donuts girls. Let them rot there, was my take on it. Fuck them. Ms. Jenna’s words startled me from my revery.

“Tim, I can’t assemble all the good women who have been insulted and looked down upon by you over the years. But here, in this room, I can represent those trod-upon souls. Through me, they will express certain things. They will give voice to their indignation, their profound rage at their treatment at the hands of men. I won’t let them down, and I won’t let you off. Get ready to have shit thrown in your face, Tim.”

“Yes, Ma’am.” I replied meekly.

If truth be known, low as I felt then, I would have wept tears of joy if a woman I had wronged were to push my face into a pile of her shit, freshly issued from her pink little anus. I’ve got that coming and more, no question.

Ms. Jenna sat at the edge of the bed and took the belt up in her hands.

“This is one way to get my message across, Tim. To show you where you stand in the scheme of things.” she said, letting the strap run over her palm. “And it’s also a way of saying, ”Fuck you”, male pig!’ Yes, that’s another important function. Women really need to vent. That’s why weaklings like yourself appear in the world. To deliver over to the offended women of the world a man they can walk on: someone weak, inflated, frightened. And, Timmy, that’s you! you are clearly the ‘loser’ poster child.”

“Now,” Ms. Jenna said as konya escort she stood and walked around me where I knelt. “We are going to challenge some of your ridiculous notions about women. Stand at the foot of the bed and hold onto the post.”

“I did as told.

“I know I’ve got a whipping coming, Ma’am.”

“Yes, Tim. No doubt. In fact, a series of them, if my estimation is correct.”

Ms. Jenna came to where she was facing me with the end of the belt wrapped around her slender hand.

“My very useful leather friend here is going to help me teach you a lesson.” she began.

“You see, Tim, your stupidly formed attitudes towards women go deep. In any given situation, you would not think twice about keeping a woman down, or sabotaging her if she were to get ahead. You’ve done it many times, I imagine. Thought of her as a “stupid cunt”. How often have you uttered those words? Answer me.”

“Many times, Ms. Jenna. Countless times.” I said.

“You’ve said them about me, haven’t you, Tim?”

“I have, Ma’am. Many times.”

“Well, Tim, I’m not stupid, as you know. But I can definitely be a cunt, depending on the situation. It comes out especially while I’m enjoying having some pretentious asshole male by the balls. Like right here and now, Tim.”

Ms. Jenna, gave me one more searching glance, and my knees trembled. With a knowing smile, she moved behind me, waggling the belt from her wrist. I felt her hand on my buttock, lifting it appraisingly.

“You’ve got a nice ass, Tim, which makes you still more perfect in your role. The ideal situation for a women who needs to vent is to have someone with a pig mentality, arrogance, and an ass with some flesh on it. We do love to watch it shift and jiggle under the strap!”

Ms. Jenna allowed the belt to slide across my back slowly. A moment later, the first stroke fell, cracking loudly. My right cheek felt on fire, but it was mixed with a warm glow. Another crack. Ms. Jenna handled the belt so assuredly. It struck flush with the skin. I couldn’t wait to see the marks she would leave!

“Who’s a cunt, Tim?” she demanded, and brought a brisk flurry of belt-strokes down upon me.

“I’m a cunt, Ma’am. I’m all cunt.”

“Whose balls are those between your legs, little boy?”

“They are your balls, Ma’am.”

Ms. Jenna continued her methodical whipping. She focused for awhile on my legs which gave my burning cheeks a rest.

“That’s enough for today, I guess.” Ms. Jenna remarked as she examined her work, then hung the strap back in the closet.

“Come here.” she ordered, and I relaxed my fingers from the bedpost where they had held so tightly. I came to her and knelt.

“Get up. I didn’t tell you to kneel, did I?” she said, frowning at me. Better be good, Tim, I thought. Otherwise, another ass-whipping could be in store.

“Turn around and look at yourself in the mirror.”

I did as instructed, and beheld the lovely red stripes that criss-crossed my ass and thighs. Wow! I thought. A woman did this to me! You’ve been whipped good by a smart, tough woman, Tim. (And you’ll be wanting more of it!)

I surveyed the marks further, some of which were raising into welts.

“What you see there, Tim, explains your new relationship to women. Do you understand?” she said, looking me full in the eyes.

“I kayseri escort do, Ma’am. Sometimes a dog needs it.”

“Make that anytime, Tim. Anytime I see the need for it. Kneel now.”

As I knelt, Ms. Jenna removed her top and her panties, giving me both garments to fold. As I tended to them, I risked a quick glance at her pussy. God! How I wished to worship it! The seat of her power, the ruler of my very life.

“The panties, Tim. Are they dirty?” she asked.

I respectfully examined the panties. There was a light brown streak from where her anus had rubbed against it.

“A little, Ma’am.”

“You’ll take care of that later. Now, what do you see, little boy?”

“Such a beautiful woman!” I cried out. “I’m so lucky to have been given a strapping by you, Ma’am. You gave it to me good!” I said, feeling almost feverish in my devotion.

“I know my place, now, Ms. Jenna.” I said, then paused.

“I’m your dog, aren’t I Ma’am?”

“You are definitely my dog, Tim. Why, look how far we’ve come. Only yesterday, you were calling me a cunt and a whore!. Imagine that.”

“I’m so sorry!…I…God, I’m so…”

“Shut up!, dog-boy! I can always go to the closet, Tim. I’m warning you! No more of your childish blubbering!

I did manage to shut up. Damn! I kept getting overexcited. No control. Just a stupid-ass dog with a hard-on. But Ms. Jenna would change all that.

I knelt with my head hung, ashamed of my stumbling.

There is your bed, Tim.” Ms. Jenna said, indicating a large cardboard box, some two feet by six with its top removed. It was just a foot off the ground and easy to step into. Inside were an old wool blanket and a worn sheet.

“I may call you at any time of the night to serve me. Be prepared. Well, get in. Try it on for size.” she said, and laughed. “Oh, Timmy’s got a new home! How exciting!”

I stepped into my new home and arranged the bedclothes. I knelt in my box as Ms. Jenna prepared for bed. After bringing a glass of water to her bedside, Ms. Jenna approached me. If I’d had a tail, it would have been wagging wildly at that moment. Mmmmmm. The woman who whipped my ass. How beautiful, how powerful she is!

“Tim. We just got started today.” she said, and stroked my face softly. I ventured to kiss the soft palm of her hand – the same hand that had swung the belt so hard and fast into my flesh.

“I want to worship you, Ma’am.” I said softly. “Please.”

“You will, Timothy. But that’s a training all in its own. For now, though, you may wish to say a few words of respect.”

With Ms. Jenna’s dark pubic thatch only inches from me, I bowed my head.

“I want to pay my respects to your pussy, Ma’am.” I said, afraid to raise my eyes to look upon it. This woman frightened me so!

“Let me hear.” she commanded.

“You rule over me, your foolish little pig-dog. Your greatness is immeasurable. I know that you must be firm with me, and I don’t know how I could have disrespected you so before!”

“Good, Tim.” she said with satisfaction, and she offered the back of her hand to be kissed. “Tomorrow, you’ll come here after work. Straight here, understand?!”

“Yes, Ma’am!” I cried delightedly. I began to whimper like a puppy, I was so excited. I loved the sounds that came from my throat. She wasn’t stopping me, so I gave full range to my dog sounds.

“Goodness!” Ms. Jenna exclaimed. “such a happy little doggie!”

I frisked from side-to-side in my box, whining gently as Ms. Jenna petted my head.

“Now, don’t you foul you sheet! I find anything there, you’ll get it good!”

I snuggled down into the musty blanket as Ms. Jenna clicked off the light.

More to follow.

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