The Reluctant Mistress and Her Unexpected Transition Part 16

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Danny came home early that Wednesday, four thirty, an early start to the four-day Thanksgiving holiday. I heard him come in the kitchen door, I heard the junk drawer opening and closing; I knew he was stripping and putting his collar on, good boy, a pause while he got on his hands and knees and crawled through the hallway and into the living room. Imagine his shock when he spotted Rebecca’s elegant legs crossed next to mine. I could just imagine what was going through his submissive head.

To his credit and credit my good training, he paused only a fraction of a second, then continued forward until he was at my feet. I was wearing black pumps with 2” platform heels, a nice counterpoint to Rebecca’s strappy 4” white stilettos. “You may kiss my feet, slave,” I said in my best Mistress voice, hoping that Rebecca approved so far. I let Danny finish his worship and then said, “And now you may kiss Mistress Rebecca’s shoes . . . and thank her for helping you get your new job.”

Danny shifted two feet to his right, until he was directly in front of Rebecca’s expensive high heels. He dipped his head and politely kissed the top of the sharply pointed toe of each shoe. “Thank you for helping me get my new job, Mistress.”


Thank You Mistres

“You are welcome, slave,” Rebecca responded formally. Danny had his eyes properly cast down on the floor, so there was no way he could see the knowing smiles exchanged above his head.

“Slave,” I said, “We would like some afternoon tea. Please prepare a tray and bring it here.”

“Yes, Mistress,” Danny said. He backed away from Rebecca’s feet, turned around and crawled out of the room. I was pleased to see he was huge in his cock cage.

Five minutes later the whistle of the tea kettle sounded, and a few minutes after that our girl chat was interrupted by the sight of my slave at the entrance to the living room. I had trained him to wear an apron when he served me. He looked magnificent standing there, eyes cast down, holding a silver tray with steaming teapot, cups, saucers, sliced fruit and cookies, using my best china. Good boy.

I let him stand there silently for a few moments and exchanged a look with Rebecca. I was pleased to see she approved. How could she not? Danny looked sexy as hell. My slave manservant. Of course, she had one of her own (only now it dawned on me why she called him ‘Hamilton’), but this one had to be cuter, after all he was thirty years younger than Hamilton (and now it became clear why their age gap worked so nicely). “Slave, you may enter. Put the tray on the coffee table and serve us.”


Tea Time

Danny moved to the table and set the tray down. He filled two cups. “I have a selection of teas, Mistress Rebecca, which would you prefer, the Earl Grey or something milder?”

Well bless his soul, I thought, Danny does have the heart of a servant, and a perfect gentleman, too. I had never trained him to serve more than just me, but he was handling it nicely, thinking of more than one choice of tea and offering it to our guest first. And the sliced pear, that was inspired. I beamed.

“The Earl Grey is fine, slave,” Rebecca said, her tone not quite dismissive, but like she was speaking to the hired help. “I’ll skip the cookies and just have fruit.”

When Danny had finished serving us, I ordered him in position with a silent wave of my hand, four fingers. He took his place on hands and knees to my right, Rebecca on my left. We drank our tea and chatted about Thanksgiving plans. She and Hamilton were driving to Richmond to visit his family on Sunday. The traffic on I-95 would be awful. We went on this way for a few minutes until we had almost finished our tea, when Rebecca put her hand on mine, a signal we had agreed upon in advance.

“So Mistress Rebecca, would you like to play fetch with my pet?”

“Oh how sweet, of course.”

“Come here, pet, let me remove your apron,” I told Danny. “Then get in fetch position.”

Danny crawled to my feet and I pulled the strings and removed his apron. He crawled to his spot next to the couch, facing the dining room. I collected the hollow rubber ball with a jingle bell inside that I used for this purpose. It was a humiliation that I used to reinforce Danny’s status as my pet; I wondered if he would balk at fetching for someone else. He’d better not.

She turned to me inquisitively. “Does your slave have a name when you play fetch?”

“No, just ‘pet,’” I replied. It hadn’t occurred to me to give him a dog name. I handed her the ball.

“I used to call my Hamilton ‘Ajax’ when we played this game,” she remarked. “It’s become hard on his knees so we don’t play much anymore.” She reared her arm back and tossed the ball into the dining room, quite the throw. “Fetch, boy!”

Fetch boy!

Danny scurried off on his hands and knees into the dining room, crawled under the table, picked up the ball with his mouth, then scurried back on all fours to Rebecca’s feet. “Good boy,” she cooed, ruffling his hair, which had already grown an inch since the Halloween buzz-cut. “Again?”

Danny panted eagerly and wiggled his tush at the prospect, just as I had trained him. She threw the ball again. He retrieved it again. We repeated the game a few more times and then Rebecca handed me the ball. “Thank you, that was fun putting him through his paces. He’s really agile on all fours.”


Now we had reached the moment for which I had some misgivings, but which Rebecca reassured me would be a turning point in Danny’s training and my progression as his Mistress. I put the ball and my doubts aside and said to her, “Would you like to take him downstairs and play a little?”

“I would love that, dear. He seems such a fine young specimen, you chose well.”

“Slave, heel,” I commanded to Danny, who was breathing hard from our game. He took his positon on my right and I snapped on his leash. I walked him to the basement stairs, Rebecca following. At the top of the stairs Danny turned around so he could safely crawl down the stairs backwards. It was at that moment that he got his first glimpse of Rebecca: legs a mile long on top of those high heels, wearing a slim, knee-high wool skirt, that exquisite silk blouse; she exuded a statuesque, commanding presence.

I knew he already knew it was her, but the shock of recognition on his face told me that suddenly it had become real, he was going downstairs and she was going with us, what had been our private game was enlarging into something much greater. He was not just my slave, he was a slave, subject to my will. He would do as I pleased, when I pleased, with whom I pleased.

A Slave

As we went down the steps that afternoon, I must admit I had some doubts, but they were balanced by an intense curiosity to see Rebecca, the ultimate Mistress, in action. And to be completely honest, the situation was triggering my bi-sexual longings, they were bubbling up once again. I found myself fantasizing her kissing me in front of Danny, the two of us teasing him . . . that and much more.

There was plenty of light spilling through the glass bricks so I left the light off and walked Danny to the dungeon door. At the doorway, I flicked the switch that turned on two amber-coated LED lights that gave the room a warm, soft glow. I led Danny to the underneath the pull-up bar, which had become my favorite spot to hang him in a stress position. “Stand, slave.”

Danny rose to his feet, wincing. His hard-on had to be excruciating in that cage. “Up on your toes, arms raised,” I commanded. Danny lifted his hands into position next to the leather cuffs that dangled from screw-eyes inserted at either end of the wooden dowel. I retrieved the footstool and stood on it, expertly wrapping the cuffs around his wrists. I retrieved the spreader bar and attached it to his ankles. Now he was spread-eagled, up on his toes, completely immobilized, swaying as he struggled to keep his balance. Next came the ball gag, hanging from a hook. I inserted the red ball in his mouth and wrapped the harness around the back of his head, buckling it in place. Poor slave, so vulnerable now.

Rebecca stood at the door, calmly observing my preparations. I knew Danny could see her out of the corner of his eye. I debated blindfolding him, but decided against it. Rebecca was a stunning woman and I wanted him to see her. I liked it when Danny’s roving eyes triggered his lust, and lust collided with the harsh reality of his cock cage. As long as I was the only woman he ever fucked again in his life, I was fine with him looking. Besides, I sympathized; I couldn’t keep my eyes off Rebecca, either.


I went to the wall and selected the riding crop. I walked in front of Danny, slapping the tip of the crop against the palm of my hand. “We’re going to play a little game now, slave,” I said huskily. “As you can see, I’ve invited our guest to take part. You don’t mind, do you, letting our guest play with you?”

A muffled response through the gag, what sounded something like, “No, Mistress.”

“As if you had a choice . . . Rebecca, do you care to take the crop and step behind Danny?”

Rebecca stepped into the room and took the riding crop. Wielding it expertly, she traced a line down Danny’s flank as she stepped into position behind him. Meanwhile, I pulled down the shoulders of my long-sleeved black knit halter top, exposing my breasts to the nipples. Danny’s eyes widened with lust.  “Here’s how the game works, slave. You endure ten swats from Mistress Rebecca, and I’ll give you ten seconds to suck your Mistress’s nipples. Shake your head up and down if you agree.”

Danny’s head nodded vigorously. “Oh sweet thing, aren’t you eager to play,” I teased. “But before you agree, there’s more to the game.” I pulled out the Japanese clover nipple clamps from the pocket of my capris and dangled them in front of Danny’s nose. “You have to wear these while we play.”

Behind him, I saw Rebecca lazily running the tip of the crop from the nape of Danny’s neck down his spine to his ass. “Are you willing to suffer for Mistress while we play our game?”

Play Time

Danny nodded again, this time less vigorously. In the last few weeks, he had graduated from clothes pins and quickly established a love-hate relationship with the dreaded Japanese clover nipple clamps.

“And just to be fair, you need to know there’s a catch,” I said with an evil grin. “The clamps must come off each time before I’ll let you suck my nipples.”

I saw a flash of dread in Danny’s eyes. I had learned that his nipples numbed in a matter of minutes when squeezed by jaws of the clamps, and that he could endure them for at least thirty minutes, maybe longer. The torture came when removing them, an intense agony that lasted a minute or more. Taking them on and off was much worse than simply leaving them on. My final condition guaranteed he would suffer mightily for the privilege of sucking on his Mistress’s tits . . . and that was only after he endured whatever pain Rebecca administered as the pre-condition to his bittersweet reward.

“Tsk, tsk . . . such a cruel bargain,” I taunted, looking over Danny’s shoulder to see Rebecca’s face. She was enjoying my performance, her face shining with pleasure. She spun the tip of the riding crop in a circle, signaling she was ready to go. I pulled down the halter another inch, completely exposing my breasts. “So is the reward worth it to you, slave? Do you still want to play with us?”

Danny grudgingly nodded, steeling himself for the price he would have to pay to get his prize.


“Very well.” I grasped his left nipple and squeezed hard, creating a fold of skin with the nipple at the center, and attached the first clamp. Danny winced. I repeated the process with the right side of his chest and he winced again. A silver chain dangled between the nipples. I tugged on it, knowing that the burn was intense, having tried the evil little devices on myself. A bit of drool leaked out one side of Danny’s mouth. I wiped it with a finger. “There, there, let’s not get all messy, slave. Are you ready?”

“Yes, Mistress,” Danny tried to say through his gag, but what came out was three muffled grunts.

“He’s all yours, Rebecca.”

Rebecca’s turn

The first blow was the hardest; it came with a stinging impact that made Danny howl against the gag and jerk violently against his restraints. I flinched and put my arm out to steady him. Rebecca’s next swat was not quite as hard, but Danny jerked again. I had briefed Rebecca that Danny’s limit was a seven or eight, but it hadn’t occurred to me that her seven was my eleven. Eight more blows followed, all to his rear from what I could tell from her stance. When Rebecca had finished, Danny’s chest was heaving.

“Poor thing,” I cooed, reaching behind Danny’s neck to unbuckle the gag. “I think that might’ve hurt a teeny-weeny bit, didn’t it?” The ball gag came out and Danny gasped and inhaled a huge lungful of air. “Now slave, I want you to rate those blows. Tell me how hard Mistress Rebecca hit you.”

Danny hesitated, reading an internal pain gauge known only to him. “Uh . . . an eight, Mistress.”

“I see. Well, you’ve earned your reward, slave. Are you ready?” I tugged down on his nipple chain.

“Yes, Mistress,” Danny said, wincing, girding himself for the flood of pain to follow. I unclipped the clamps from his nipples and he writhed in his restraints. I cupped under my breasts with my hands and lifted them up toward his mouth. He had to almost hyperextend his shoulders and bend his head down as far as he could to reach my nipples. His lips greedily found them and he sucked hard, first one and then the other, trying to erase the pain flooding his chest with the pleasure of my breasts. I counted to ten and pulled away. He groaned. “Poor thing, ten seconds goes by so quickly, doesn’t it?”

“Yes, Mistress,” Danny half-sighed, half-groaned.

“Are you ready to play the game again?”

Danny had that wild look in his eyes that told me he was going into subspace. “Yes, Mistress.”

I reached to his chest and squeezed the flesh around the nipples, attaching the tit clamps as I had before. This time, with the ball gag removed, Danny’s lips pursed and he grimaced with pain. With the clamps reinstalled, I put my hand against his chest and nodded to Rebecca. This time the blows came to Danny’s back. I could feel them through his chest, each one feeling like a ten. Danny gritted his teeth and grunted with each snap of the riding crop, taking it like a man. I was proud of him. When Rebecca was done, I removed the tit clamps and again Danny writhed in agony. This time I lifted up on my toes, bringing my nipples to his greedy lips. I might have let him suck for a little longer than ten seconds.

We played our game eight more times, until I could tell Danny was getting exhausted from being up on his toes, his nerves frayed from the whipping and the repeated administrations of the nipple clamps. I made eye contact with Rebecca and she nodded that she was finished. I lifted my halter back in place and was about to reach up to free Danny from his restraints when Rebecca said, “Vanessa, dear, do you think I could have a moment alone with your slave?”

The request caught me off guard. “Um . . . yes, of course, Mistress Rebecca.”

“And can you put the ball gag back in? I want your slave to listen, not speak.”

“Yes, of course.” Feeling a little discombobulated, I obediently picked up the gag from the floor and re-inserted it in Danny’s mouth. As I fastened the locking straps behind his neck, I saw a look of alarm on his face, “Are you going to leave me with this strange woman?”

I gave Danny the stern look in response, silently saying, “Yes I am, don’t be alarmed, I love you.”

Rebecca stepped around Danny to stand next to me. She took my hand in a sisterly fashion. Reading my mind, she said reassuringly, “Don’t worry, I just want to have a little chat with your young slave here. I promise I won’t hurt him a bit—” she caressed Danny’s cheek with a chuckle, “—I’ve already done all the damage I care to do today.” She removed her hand and placed it on mine, drawing me closer, kissing me on the lips. I felt sparks fly. As our lips separated, she said, “Your slave needs to hear from someone else just how lucky he is to have found a Mistress like you, darling.”

How could I argue with that? I gave Danny a parting silent glance, “Be good!” and walked out the door of the dungeon, leaving him in Rebecca’s capable hands.

Next Episode: The End of Innocence



The Reluctant Mistress and Her Unexpected Transition Part 15

The Reluctant Mistress and Her Unexpected Transition Part 17


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