The Reluctant Mistress and Her Unexpected Transition Part 20

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 The Dilemma

Finding myself more deeply in love with Danny brought about an unforeseen dilemma in my life. When we started as Mistress and slave, I thought I was doing him a big favor, playing an unnatural role on his behalf, an expression of my love. Then I found myself acting and thinking in new ways that made me feel authentically myself, a stronger, bolder woman, which then led to my relationship with Rebecca evolving from intimate friendship into something deeper, a new kind of love.


Rebecca became the sister I never had, a sister Mistress, unlocking the door to a long-repressed attraction to my own sex. Rebecca was both the key and the door and the room behind the door where this attraction came to life. It was her—I couldn’t imagine wanting to sleep with any other woman.

At first, it was easy to dismiss any guilt I felt over sleeping with Rebecca because I had already begun thinking of Danny as property, my slave, without rights, not to mention I was having sex with a woman, not a man. However, now that I could see our relationship evolving into a (female led) marriage with children, and realizing that he had done me as great a favor as I had done for him, I felt pangs of guilt.

Sleeping with Rebecca began to feel like cheating on Danny. I didn’t want to give up Rebecca, but I could never give up Danny, and I didn’t want to hurt him. If I only had sex with him, it meant denying something wonderful that had come into my life, the intimacy of loving a woman; not just the sex but the treasures of Rebecca’s wisdom and unconditional love. I couldn’t give that up.

Complications of Love

I loved them both. How could I give up either one?

And what of Hamilton? Early on, Rebecca had assured me that our relationship did not threaten her marriage; in fact, she revealed to me that she had long ago brought cuckolding into her Mistress-slave relationship, meaning she made Hamilton aware that she was dating other men. Not only did she date and sleep with other men, she sometimes made Hamilton watch her have sex with her “bulls,” a fitting name for unattached younger men.

Frankly, I was shocked to learn this. It sent me into a frenzy of online research to try to understand something that on face value seemed immoral (overlooking of course the hypocrisy that I was having sex with Rebecca, albeit not in front of Hamilton). Rebecca was unapologetic; vanilla rules did not apply to Mistress-slave relationships. She insisted that cuckolding only deepened her relationship with Hamilton, it further cemented his status as her slave, and he willingly embraced it. Who was I to judge?

Except . . . except now I was involved with her. I found myself wondering if she entertained a stable of male and female lovers. I began to struggle with jealousy. Was she “cheating” on me? She had never promised me fidelity; it was I who had begged her to fuck me, teach me, and I did so without condition. Oh, the slippery slope I found myself on! At our next Mistress lunch (in a very private booth), I opened my heart and shared my feelings. I didn’t want secrets; Rebecca needed to know how I felt.

“Vanessa,” she said over her salad, “you have to make a choice. Either you go back to living your life as you did before you discovered your true self, or you embrace it. If you choose to embrace it, then more open lifestyles become possible. You make your own rules: you can have an exclusive relationship with your slave, or you can have a relationship with me and a separate relationship with him, or you can share him with another Mistress—” she raised an eyebrow, “—as you already have with me.”


I nodded. Of course, Rebecca was referring to our tea party the day before Thanksgiving. I had never asked her what she had said or done to Danny when I left them alone in the dungeon, nor had I asked Danny. Strange that I hadn’t, I know. But to ask Danny would have been a sign of weakness, revealing to my slave that I had entrusted him with another Mistress and didn’t already know what had transpired. In Rebecca’s case, it was my desire to honor her, trusting a vastly more experienced Mistress. That, or it was an unconscious fear of what I might learn. I supposed I would learn soon enough in Danny’s diary.

Since Rebecca had raised the subject, I said, “I never have asked you what exactly you said to Danny that day in the dungeon. Do you mind if I ask?”

“I told him I’d cut off his balls if he ever hurt you,” Rebecca replied with a deadpan expression.

That pushed me back in my seat. “Really?”

She flashed an evil grin, the corners of her lips turned up. “Really.”

“I see . . . May I ask another question, about you and Hamilton?”

“Of course.”

“Does he know about us?”

Rebecca speared a carrot with her fork and slipped it between her luscious painted lips. She chewed thoughtfully for a moment then replied, “Yes, of course he does.” She studied my reaction, which was transparent, the face of a women who fears she has harmed another woman’s marriage.

“Vanessa, you still don’t get it,” she gently chided me. “A slave—a true male slave—gives up all expectations of a normal relationship. His Mistress is no longer constrained by the normal bounds of fidelity, which is not something he necessarily even wants. For slaves, being emasculated, knowing that his mistress takes other men and women as her lovers, is a huge turn-on. It emphasizes the reality that he is a man without rights, truly nothing more than a slave. Of course, all this is with his consent.”

She took a sip of iced tea and continued, “Dear, no one forces a man to become a slave in the kinky alternate reality we inhabit; it’s a choice. If you think about it, it’s no different than a man who enlists in the military and swears an oath of allegiance to follow orders. And a man who submits to the military is at far greater risk of being thrust into morally abhorrent situations than a Mistress’s slave. In my humble opinion, being ordered to kill complete strangers and sometimes innocent civilians is far worse than a submissive slave being ordered to watch his Mistress make love to another man.”

She had a point. Still, it was a lot to absorb. I needed a drink, something stronger than water. Wine. Too bad we were lunching at Panera. I asked, “So you really think slaves enjoy their Mistresses taking other lovers?”

Rebecca didn’t hesitate. “In Hamilton’s case, yes, absolutely. I can’t speak for Danny. But judging from how he responded when we were together in the dungeon, and how he responded to me when you left us alone . . . yes, I am quite certain he would get off on it.”

I stared at Rebecca, wondering if I dared ask. Yes, I dared. Better to know than be left wondering. “How exactly did he respond, if I might ask?” I inquired as calmly as my courage allowed.


Rebecca put her hand on mine. I admired her perfectly manicured nails. “Vanessa, after you left, I teased your slave. He’s a man, after all, and less capable of resisting my charms than you. And you know how well you’ve fared.” She smiled seductively, challenging me to disagree. I remained silent.

She leaned forward, speaking sotto voice. “When I had him fully aroused, I put my lips to his ears and told him that I enjoyed fucking you, his Mistress, and I would enjoy fucking him, too. I told him it wouldn’t be too long before he’d be sucking my dick while you fucked him in the ass. Do you think his cock went limp in its cage when I said that?”

I knew my slave; he probably came close to a spontaneous orgasm when she spoke that in his ear. Before I could object to Rebecca revealing our sexual relationship without my consent, she sat back and said, “Also, you should know that I told him I loved you . . . I loved you well before he did.”

I was stunned. Rebecca had never spoken the words ‘I love you,’ to me. But she had revealed her love for me to Danny. It took me a while to find my voice. “I didn’t . . . what did he say to that?”

Rebecca smiled. “As you will recall, he was gagged. He just listened, wide-eyed, like a good slave, nodding yes as appropriate. Even if he doesn’t believe I would really cut off his balls, he knows I’m dead serious about looking after you. I don’t think you’ll ever have to worry about him misbehaving.”

Neither of us spoke for several minutes. I couldn’t eat. Rebecca finally broke the silence. “I apologize if I betrayed your trust, Vanessa.”


Another minute passed. Rebecca stabbed a slice of tomato with her fork, but couldn’t seem to find the will to lift it from her plate. I wanted to say I forgave her, but I think she already knew that; besides, what exactly would I forgive? Her honesty? That was one of the things I loved about her; she spoke the truth fearlessly. My silence was more because she had given me so much to think about.

I couldn’t leave her apology unanswered. “Thank you,” I said. “And I love you, too.”

Her beautiful face grew transcendent, gratitude shining from her eyes.

Eventually she went on, “Vanessa, I can tell you this. In my experience, the fact a slave’s Mistress is desired by other men and women only serves to arouse him more, to make him appreciate her worth. The reality that she has a sex life independent of him only serves to reinforce his status as her slave, his absolute lack of rights in all things. All things. Above all else, that’s what they want. They don’t want to be an equal partner in a traditional marriage. And if they do end up in a vanilla marriage, they hate it and spend all their time longing to be the collared slave of a Mistress.” She put her hands together in a Buddhist gesture that I had never seen her use before. “You’ll just have to trust me on this.”

I did trust Rebecca—with my life. After reading Danny’s slave diary, I realized that in many ways, what I was for Danny, Rebecca was for me—the one who made me whole. Knowing that, and knowing that I could never go back to the woman I was, I had an important choice to make.

Next: Vanessa’s Choice



The Reluctant Mistress and Her Unexpected Transition Part 19

The Reluctant Mistress and Her Unexpected Transition Part 21


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