The Reluctant Mistress and Her Unexpected Transition Part 21

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Vanessa’s Choice

Of all things, a Christmas letter from Mom helped me make up my mind about how to proceed. When Dad died, he left me as co-executor of his estate, the other executor being his lawyer, with instructions to divide the proceeds of his estate equally between his wife and four children.  As you might imagine, this deeply offended my mother. Without explanation, she left for Oregon.


In Oregon, she went to live and work at a wild horse sanctuary, which turned out to be in financial trouble. Before a year had passed, she wrote that she wanted to buy the property to keep it from being sold to a neighboring cattle ranch, which would leave the horses with nowhere to go.

Dad’s lawyer washed his hands of the situation and signed a document that made me sole executor. It fell to me to decide what to do with the proceeds from the insurance policies, a substantial retirement portfolio and the sale of the house. After much soul searching, I fell back on something Dad taught me growing up, “Colonel Whetstone’s difficult decision matrix.” It goes something like this:

  • Can you do both?
  • A “yes” generally means you have twice as much to do, but also twice as much fun and you don’t have to give up something you love. Dad liked to say, “You can sleep when you die.”
  • Choose a life less ordinary.
  • Dad cited Charles Lindbergh, who wrote, “I decided that if I could fly for 10 years before I was killed in a crash it would be a worthwhile trade for an ordinary life.”
  • Save the living.
  • Dad said you shouldn’t pour your lifeblood or money into the past. The dead are dead, be it jobs, people, or relationships, so spend your time and treasure on something living.

I couldn’t do both; I couldn’t split the money as Dad instructed and still help Mom. She had chosen a life less ordinary, and was saving the living. I talked it over with my brothers. We sent her the proceeds of the estate, almost two million dollars. She bought the ranch. Today the horses run wild on 365 acres.

Christmas Letter

In her family Christmas letter, Mom expressed her joy and gratitude to me and my brothers. There was a sweet picture of her leaning on a fence, looking out on a beautiful expanse of open land, a herd of mustangs grazing in the distance.  The caption read, “Happy, happy, joy, joy! Love from Oregon.”

That decision turned out well. So, applying Dad’s decision matrix to my situation, I decided that I could do both. If it ended with a crash in ten years, it would be a worthwhile trade for an ordinary life. Studying the calendar, I concluded that (somewhat ironically) the best day to start was Christmas Eve.

Christmas Eve, 2014, fell on a Wednesday. The bank was open until five, but Danny’s auto repair shop closed early, at one p.m. Over breakfast, as he ate cereal and milk from a stainless-steel dog bowl at my feet, I gave my slave instructions to prepare for my arrival with a guest at five thirty. The house should be spotless, a vase of flowers on the dining room table, a tea service for two prepared with the kettle ready on the stove. Further, he should be squeaky clean, inside and out, wearing his collar and cock cage and locked inside the cage upstairs when I got home. Oh, and I wanted a live (with root ball) decorated Christmas tree in the living room. The ornaments, lights and skirt were in boxes in the attic; the wrapped presents in the hall closet should be arrayed under the tree.

Not being an unreasonable Mistress, I gave him ten twenty-dollar bills, $200 to purchase the tree and do any last-minute shopping (I couldn’t imagine he had saved anything from his weekly allowance). He had permission to take my truck so that he could haul the tree home. I knew all that would make for a very busy afternoon of preparation.

Bank’s Closed


Rebecca and I closed the bank at five and were out the door by five thirty. We stopped at our local watering hole for a glass of wine and arrived at the house at six fifteen. I was pleased to see that Danny had parked the truck on the lawn, leaving the driveway for my Honda Civic and Rebecca’s BMW coup.

We were stylishly dressed, Rebecca in a charcoal gray pants suit and high heels, me in a skirt and blazer with mid-calf boots. Rebecca carried an overnight valise. This was a sleepover; Hamilton was spending Christmas Eve with his parents, Rebecca would join him tomorrow for Christmas dinner.

Inside the kitchen door, I was pleased to see the tile floor shined, the counters spotless and my silver serving tray prepared for tea service. I led Rebecca to the bedroom where she dropped her valise on the bed, then we moved through the hallway into the living room. A Balsam fir reached nearly to the ceiling, lights twinkling and ornaments artfully hung from the boughs, wrapped presents arrayed on the skirt under the tree. As the saying goes, it was beginning to look a bit like Christmas.

The dining room table was set for two, the centerpiece my crystal flower vase filled with a bright arrangement of red carnations, green spider mums and cedar. Well done, slave. Rebecca nodded with approval. “I don’t think Hamilton could have done any better,” she said. We moved through the dining room to the foyer behind the front door, which also accessed the stairs to the basement. Rebecca said she wanted to make a few advanced preparations in the dungeon.

Dungeon Preparations

We went down the creaky stairs. It was dark in the basement; I flicked on the light and we walked over to the framed-in room that serves as my modest dungeon, our heels clicking on the concrete floor. Inside the dungeon, Rebecca showed me the modification she wanted to make, tying the wrist restraints to clothesline, running the lines through the eyelets of the hanging bar and then to cleats mounted on the wall, so that we could raise or lower my slave at will. “It’s difficult to fuck a man when he’s standing straight up,” Rebecca explained. “Better to have him kneeling on the floor, doggy style.”

Ah, the voice of experience. So far, I had only pegged my slave in the bedroom, bent over my bed. Rebecca roamed around the room, fingering the boat hooks and snap links arrayed on the wall, tugging on eyelets, testing their strength. She lifted the flogger from its hook and took a few swings, the blows landing on the leather-upholstered whipping table. She returned the flogger and selected the riding crop, snapping the tip on the palm of her hand. I thought of Danny, locked in his cage two floors above, patiently waiting for whatever fate would bring. Little did he know he was about to become the subject of a second Mistress. We were going to become an extended family. Rebecca interrupted my thoughts, “Have you ever tried either of these on yourself, Vanessa?” she asked.

I shook my head with a mild snort. Of course not.


“Have you ever been spanked?”

Again, I shook my head . . . but I found it unexpectedly arousing that Rebecca would ask.

“You should, you know, just to get a feel for the sensation.”

I gazed at my friend and lover, amazed as ever by her forthright way of addressing these delicate topics. She never dallied around, no subtle hints. “Are you suggesting we do this now?” I stammered.

“No time like the present,” she replied with a grin. “Your slave will never know, he’s in his cage and can certainly wait a little longer. Consider it advanced Mistress training.”

Advanced Mistress Training

I felt myself blushing, and not only that, a hot welling in my crotch, evidence that this suggestion aroused me whether I admitted it or not. I recalled the moment that first Sunday morning when I told Danny to lay on my lap, his deer-in-headlights expression when he realized I was seriously about to do the very thing he so longed for, give him a spanking. Now here I was in the same situation, only it was Rebecca, a fellow Mistress, suggesting I try it out. A wave of dizziness swept over me.

“Oh come on, now, tell me you aren’t a little curious,” Rebecca teased me. “Come over here to the table, pull your skirt down, I’ll give you a few swats and we’ll be done with it.”

Sleepwalking, I took the few steps to the whipping table, unzipped my skirt and let it fall to the floor. I picked it up and handed it to Rebecca. “Panties, too,” she said, making a ‘give it here’ gesture with her hand. I dutifully pulled my panties down, awkwardly tugging them over my boots, almost tripping in the process. I handed her the panties. “You might as well take off your jacket.” Rebecca helped me out of the blazer. Now I was standing partially naked, wearing only bra, blouse and boots.

“Bend over, girlfriend,” Rebecca said with a friendly chortle. “This won’t hurt a bit.” She took my hair with a sweep of her hand and moved it to one side. “Are you ready?”

“I guess so,” I semi-squeaked.

“Don’t forget to rate these, one through ten. We’ll begin with the flogger.”

Whack. The flogger came down on my ass, broad and soft, feeling like the brush of a pine bough against your face when you run through a forest. It didn’t hurt a bit. “Uh . . . maybe a three.”

“See what I mean, not so bad. Let’s do it again.”

Whack! This time she came down harder. I flinched. I felt sudden heat rising in the cheeks of my ass, an unexpected tingling in my clit. “That was a five or six,” I said, trying to sound clinical.

“Good. Now I’ll do it that hard a dozen times, so you can feel the sensation building.”

Any thought of protest fled me. I was a willing victim. As the blows from the flogger rained down on my derriere, I felt circuits begin to fire, my cunt moistening, my clit tingling.

After the flogger, Rebecca demonstrated the riding crop. It had a sharper, more defined impact, leaving a stinging sensation, but not unpleasant. No wonder Danny loved it when I punished him.


“Almost done,” Rebecca announced after she had snapped the riding crop against my ass and thighs a dozen times. “Now for a spanking.”


“A spanking?” I croaked.

“Yes, of course, we can’t leave that out,” Rebecca insisted. “Let’s use the chair.”

I kept a chair in the corner for just this purpose. Rebecca went over to it and sat down, signaling me to join her. Spanking was so much more intimate than a flogger or riding crop; I felt hot juices welling up inside me as I walked over to her. What if I betrayed myself and left a wet spot on her expensive pants? Then I saw her spreading my panties neatly in the center of her lap. How did she know?

I bent over her, awkwardly reaching for the floor while keeping my boots planted on the ground, sort of a downward dog yoga pose. “Other way,” Rebecca instructed. “You know I’m a lefty.”

Oh my god. I did know that. I pushed off the floor and reversed the downward dog, this time facing to her right, my ass to her left. “Go ahead and put your weight on my lap, Vanessa, I won’t break.”

I settled my weight on her lap, which left the toes of my boots touching the floor and took the weight off my hands. I wrapped my fingers around the chair legs, trembling. “Ready?” Rebecca said.

“I guess so,” I choked out, finding it suddenly hard to breathe.

“Say, ‘Yes, Mistress, I’m ready’ . . . it’ll make it more realistic.”

“Yes, Mistress,” I said, repeating the words I’d heard Danny say a thousand times.

Whack! Rebecca’s hand came down on my ass. I let out a yelp. “That one was for not saying exactly what I told you to say,” Rebecca chided me, her tone suddenly firm, sounding just like I did with Danny, the Mistress voice. “You are to say, ‘Yes, Mistress, I’m ready.’”

“Yes, Mistress, I’m ready,” I parroted, wanting to get it over with.

Whack! Rebecca struck my right cheek. I flinched. “What do you say?” she demanded.

I knew the routine. “Thank you, Mistress, may I have another.”

Whack! This time the left cheek. “Thank you, Mistress, may I have another.”

“You may,” Rebecca replied. Whack! Her hand came down hard, across the crack of my ass, stinging both cheeks. I was on the verge of outrage, about to protest and get up, but just then Rebecca’s fingers reached into my wet cunt and felt around, gliding up to my clit. She began tapping it gently, just the way she knew turned me on. “My, my, Vanessa, what have we here?” she cooed. “So wet. It seems we have another one who likes to be spanked.”

“Ummm,” I half-gurgled, half-groaned.

“I’ll keep playing with you if you admit you like to be spanked . . . say it.” Her fingers probed against the base of my clit and circled the shaft. Unfortunately, there was plenty of lubricant to help her achieve maximum effect. My cunt was betraying me. “I like to be spanked,” I moaned. “Please don’t stop.”


Swiftly her fingers retracted, swept across my cunt and rose clear of my ass. A second later, Whack! Her hand came crashing down on my ass. “Owww!” I cried out. This time it genuinely hurt.

“Vanessa, you should know better,” Rebecca scolded me, rubbing my cheeks with her open palm. “You’re supposed to say, ‘I like to be spanked, Mistress.’”

Goddam it, I couldn’t believe I made such a stupid mistake. I was acting like a dumb—oh, my god, I was acting like a dumb sub. Just like Danny. No wonder he couldn’t think straight; spanking addled your brain. I repeated through gritted teeth, “I like to be spanked, Mistress.”

Whack! Her hand came swiftly down. “Thank you, Mistress, may I have another,” I said.

Whack! “Thank you, Mistress, may I have another.” My ass was on fire.

Whack! “Thank you Mistress, may I have another.”

“No you may not.” I felt Rebecca’s fingers slip between the folds of my cunt, probing, reaching deep into my vagina, pressing against the spot I had never known existed but had been expertly revealed by Rebecca in our lovemaking. She began driving the tips of two fingers against the spot, a vigorous motion that seemed invasive but had proven to produce rapid, repetitive orgasms. I heard myself making primal grunts with each stroke. Heat waves began rocketing from my scalp to my toes and back again. My scalp tingled. I was only seconds from orgasm. Sensing that, Rebecca abruptly stopped. Her fingers retracted, moved to my clit, caressing it with a teasing touch. “Do we want to come, Vanessa?” she cooed.

“Oh, yes, please, don’t stop,” I begged her.

“I will, but first you have to agree to let me spank you a dozen times.”


“Whatever, spank me. Just let me cum, please,” I pleaded.

“Good girl. Now just be silent while I spank you, and then I’ll let you cum, okay?”


Whack! The hardest blow yet. “That’s, ‘Yes, Mistress!’ Vanessa. Say it!”

“Yes, Mistress!” I cried out, almost shouted.


She began methodically spanking me, one blow to the right check, one to the left cheek, then one across the middle; repeat. Four cycles, twelve blows. I counted them out silently, inwardly screaming in pain, because these blows truly stung, they were almost vicious. Tear welled up, leaking out the corners of my eyes. When Rebecca finished, she began tenderly stroking my burning ass, her hand gliding up to the small of my back and down to my upper thighs. She cooed, “Such a good girl, such a brave girl, you took those so well, I’m so proud of you, my dear, sweet girl.”

Oh, the power of words. How they reach into our souls and strip away the ego, how they strip away the pain, how they make us feel whole. I felt a stirring in my clit, that electric buzzing. Rebecca’s fingers slipped through the crack of my ass, into my cunt, and she probed deep into my vagina, to the place she had been before. “There, there,” she cooed, “are we ready to orgasm now?”

“Yes, please, Mistress,” I whinnied in a little girl voice.

What she Want’s to Hear

“That’s what I wanted to hear, dearest.” Her joined fingers found the spot in the deepest part of my vagina, all the way to the cervix, expertly thrusting. I felt the orgasm, which had fled under the barrage of her spanking, coming back stronger, more than just a wave, this time a tsunami. Heaven could wait.

Rebecca kept up her staccato thrusts, unrelenting, and whispered into my ear, “Now all I need to hear you say is that you want me to become your Mistress, Vanessa, that you’ll become my slave, that you want me to own you and Danny. Are you willing to do that, my beloved?”

“Uhh, uhh, uhh,” I heard myself grunting, my body on fire, my soul filled with unquenchable desire. All I wanted was release. Just let me cum, I needed to cum!

“Say it, Vanessa, say it or I’ll stop. Say you’ll be my slave,” Rebecca commanded.

I felt as if I were in a dream. From somewhere deep inside, a voice cried out from the depths of my soul, saying, ‘Don’t do it, you can never be her slave. If you become her slave, then Danny is lost to you, he becomes hers. You are his Mistress; you are her equal!”

“Stop!” I cried out, waking from the dream. “Please, stop!”

Rebecca withdrew her fingers. “What is it?” she said, sounding as if she already knew.

I let go of the chair legs and pushed off the floor, ending on my knees. I laid my head on her lap, my face pressed against my own wet panties. I didn’t care. Rebecca began tenderly stroking my hair. I lifted my head. “I can’t be your slave, Rebecca,” I said. “I’m Danny’s Mistress. We signed a contract. I love him. We’ve found our true selves together. I can be your lover, but not your slave. Danny belongs to me.”

Rebecca kept stroking my hair. A minute passed in silence before she spoke, “I am so proud of you, Vanessa. Now you know how it feels, the intensity of desire that sweeps a man’s will away and allows him to become slave to a Mistress. Now you know how Danny feels.”

“Now I know why he gets so stupid when I spank him,” I muttered. We both laughed.

“You are a born Mistress, Vanessa,” Rebecca said, “And you’ve proven it to yourself.”

I let my head fall back to her lap, wondering if I should be angry over what she had put me through. But then, how else would I know? I had to rise from the depths of desire, reject pleasure in favor of love. I had to find my true strength. “I guess I have,” I finally said. “I know what I am.”

Rebecca caressed my still very inflamed ass. She said, “You know, in my family, we have a tradition, we give the most important gift to each other on Christmas Eve . . . Why don’t we go upstairs and give your slave his Christmas gift?”

I turned my head to see her face. “You mean the gift of a second Mistress?”

Her eyes danced. “But of course—can you think of a better gift for a slave?”

I smiled. “No, I can’t . . . nor a better gift to a Mistress than a second slave.”

Rebecca helped me to my feet. We embraced, sealing the truth between us. We were Mistresses, we were equals. I would share Danny, but he belonged to me.

Next: Christmas Spirit



The Reluctant Mistress and Her Unexpected Transition Part 20

The Reluctant Mistress and Her Unexpected Transition Part 22


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