The Reluctant Mistress and Her Unexpected Transition Part 17

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Of all the toys on the list of kink, the strap-on cock was the one I most feared, because it veered into dark terrain of human anatomy which had been marked “off limits” for me since childhood. To put it bluntly, you pooped out that hole, so it was disgusting and filthy. Like a city sewer, you just stayed out. But I had seen videos and read Bend Over Boyfriend, so I knew at least in theory how it worked, and that plenty of men and women (and women and women) enjoyed strap-on sex/play. But how could I put this profoundly academic knowledge into practice? I was blocked, unable to take the first step.

Into the void stepped Rebecca, my new subject-matter expert. She graciously received me at her house one evening a few weeks after Thanksgiving (observed, by the way, as completely vanilla couples, not a whiff of kink, at her insistence). This evening Hamilton met me at the door dressed in black slacks, a white shirt and collared. He invited me in, respectfully addressing me as Mistress Vanessa and kept his eyes cast on the floor in my presence. Rebecca explained that Thanksgiving had been a holiday, a break from Hamilton’s normal status as slave. I must say that it was a little disconcerting to see him so totally immersed in his submissive role after previously experiencing him as a sophisticated retired professor, but now I that I was a member of the Mistress Sisterhood, Rebecca wouldn’t have it any other way. Hovering discreetly in the background, Hamilton was clearly immersed in his role.

So with glasses of Merlot in hand and our legs tucked underneath us on a cushy couch in Rebecca’s sitting room, I broached the taboo subject. What could she tell me about strap-on play? Over the next hour I got an education, and not just academic, but practical. Rebecca ordered Hamilton to bring in her strap-on and the related paraphernalia, to wit, two strap-ons, each with different kinds of harnesses, an enema bag and an enema bulb, various lubricants and a selection of dildos and butt plugs. I was the only one in the room embarrassed.

Strap -on play time

“Vanessa, you need to get over your hang-up about the anus,” Rebecca began the lesson somewhat indelicately. “Spit comes out of your mouth, snot from your nose, wax from your ears, urine from your urethra, ejaculate from your vagina and poop from your asshole. It’s that simple. No orifice is inherently profane. As the good book says, ‘It’s the thought life that pollutes.’ So just as you wipe your nose or use a Q-tip to clean out ear wax or a toothbrush to clean your teeth, you clean your slave’s asshole with an enema. Once you’ve trained him, he can do it himself.”


She went on to explain in candid detail how to use the enema bag, warning me that it would fill my slave’s lower intestines and he’d have to make a conscientious effort to completely void his bowels after taking in the contents of the bag, or else he’d leak water and bits of scat. (Oh my, we didn’t want that.) Alternately, she continued, prior to inserting a butt plug or if necessary for “a quickie,” the colon could be cleaned out in minutes using the enema bulb, which looked a bit like a turkey baster.

She put a hand on my arm and confided, “The way we do it is I tell Hamilton that ‘I want him clean, inside and out’ . . . that’s my code phrase to let him know I intend to play with his ass. I try to give him an evening’s advanced notice, at least a few hours. He is quite fastidious about his preparation. I think he would be horrified if he wasn’t squeaky clean when I penetrate him.”

I gulped down my wine. Well there it was, that the hardest part, wasn’t it? That wasn’t so awful.

Rebecca signaled Hamilton, who hovered in the hallway by the door, out of earshot. He trotted in with the wine, filling our glasses. “Thank you, Hamilton,” Rebecca said. “You are dismissed. Please be back here in an hour to draw my bath.”

“Yes Mistress.” Hamilton gave a polite bow and left the room.

Rebecca shot me a proprietary glance. “In time you’ll teach your slave to attend to you while you bathe and dress, do the laundry and ironing, take out your dry cleaning, clean the house, cook and serve meals, run errands, chauffeur and porter when you shop. After a while, you can’t imagine doing without a manservant . . . now, where were we?”

Squeaky Clean

“You expect your slave to be squeaky clean,” I replied absentmindedly, my mind stuck on thoughts of Danny as my manservant. We had only just started; it was barely a month since we had signed the agreement, and up until now our roles and play were always sexually charged and extreme, but I could see things evolving over time into a more refined form of submissive service with rituals that pervaded everyday life and infused it with meaning. A different way of loving. That’s where Rebecca and Hamilton seemed to have gone with this. Of course, they didn’t have children.

“Yes, squeaky clean. Want to try one on?” Rebecca said, holding out a very lifelike, flesh colored, seven-inch penis with balls mounted on a leather pad, the harness consisting of three separate loops attached to the central pad, presumably one for the waist and each thigh.

“Oh no, I’m fine, thank you,” I stammered. “I’ll just drink my wine.”

“Nonsense. Take off your skirt and try it on.” Rebecca leaned forward and thrust the strap-on into my lap. “You came here to learn; you might as well get some practical experience.”

How could I refuse? Blushing, I put the wine down and unzipped my skirt, stepping out and folding it neatly on the couch. I felt quite awkward, but also intensely aroused, standing in my pantyhose and bra in front of Rebecca. “Let me help you,” she said. She held out the leg straps. I stepped through them while she positioned the cock below my waist, above the crotch. “Now tighten the waist belt,” Rebecca instructed. I pulled the belt through the buckle and cinched it down on my waist. “Now the leg straps, snug them to your thighs.” I pulled the free ends through, cinched the straps and fastened the buckles. Rebecca stepped back, arms crossed, admiring. “There, you look sexy as hell, girl. Look in the mirror.”

MistressGet Ready!

I stepped in front of her dressing mirror and there she was, a petite redhead with a slender build and a big cock sticking out of her groin, who looked just like me. Frankly, I thought she looked rather silly. Rebecca stepped behind me, wrapping her arms around my waist and taking the cock in her hands. “I know you feel like an imposter, Vanessa, but that will pass. This dick—” she gave it a friendly shake, smiling at me in the mirror, “—it will change your life, and your slave’s, too. It’s the great equalizer. Once you learn to use it, you’ll wonder why you waited so long.”

I looked back at her in the mirror with a dubious expression. “This thing is huge, it’s almost as big as Danny’s cock, and it feels hard. I’m afraid I’d hurt him with this.”

Rebecca nodded. “You can hurt him if you don’t start gently. These are made of silicon so if it’s cold, you can soften it up under warm water. Before you start, use your finger first with plenty of lubricant to loosen him up. You can’t just shove it in him, any more than he can just shove his dick into you.”

I looked down at the dildo poking out from my body. So, this is what it was like to be a guy. It would be so easy to go pee. Poor Danny, now he had to sit down on a toilet seat like a girl.

Rebecca continued, bringing my mind back to the subject at hand, “When you first go in, it’s best if you press against him, but order him to push back and get the head of the penis through the sphincter on his own. Once you’re inside, go slow and go easy. Just being inside of him is going to rock his world, trust me. You can thrust more vigorously once you’ve warmed up his ass. It only takes a few minutes.”

All the while she was speaking, her hands were gently stroking the cock, pressing it against my crotch. My clit tingled. “There, do you feel that?” Rebecca said with a mischievous grin. I saw myself nodding in the mirror, blushing. “Feels nice, doesn’t it?” I nodded again, my knees going weak.

Rebecca released the cock. Her hands glided up my sides to my breasts, cupping them briefly, then they settled on my shoulders. She turned me around so that we faced each other with the cock between her legs, tucked under her crotch. “Vanessa,” she said in a low, sultry voice, “I’d hate for you go back to your slave without any real experience. Why don’t we try this out together?”

Double Trouble

I felt my mouth go dry. Rebecca didn’t give me a second to think up a reason to say no. She grasped my blouse and lifted it up and over my head. I didn’t resist as she tugged the sleeves off my arms. I was left naked except for my pantyhose, the strap-on and a lacy white bra. “You have the nicest boobs,” she said, looking down at my chest admiringly. “They are so perky. And my, what a hard-on!”

I looked down. Indeed, I did. Rebecca took my hand and led me to the bed. I sat on the edge and watched as she languorously stripped off her clothes. She had a magnificent body: gym-toned limbs, flat stomach, firm, full boobs that had to be enhanced. She pushed me back on the bed and straddled me. “First we need to lube this up,” she said, taking the penis in her mouth. I watched, transfixed as she deep-throated it, then slowly withdrew it, pausing, the head suckled in her lips, her eyes locked on mine. It was incredibly erotic. I could see why Danny loved to watch me suck his cock. Oh, my god.

She resumed sucking, sliding the penis in and out of her mouth, slathering it with her saliva. Then she climbed up and positioned herself above it, slipped it inside her vagina and gently settled down on me, a look of rapture on her face. I felt her gravity inside me. “Nice, isn’t it?” she murmured.

I looked up at Rebecca, her exquisite body impaled upon my cock, her weight pressing down on my clit, those beautiful breasts hanging like ripe peaches above my lips, begging to be devoured. The last shred of inhibition fled me, replaced by all-consuming lust. I reached up, took her sculpted face in my hands and pulled it down to mine. “Kiss me,” I said. “Kiss me, fuck me, teach me.”

And she did.

Next Episode: Taking Her Slave’s Virginity



The Reluctant Mistress and Her Unexpected Transition Part 16

The Reluctant Mistress and Her Unexpected Transition Part 18


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