A Natural Sissy Ch. 03

Author's note: This is a story about a woman who turns an older man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. You will need to read the previous chapter to see how we got where we are in this one. More will be added if comments from readers justify it.

Chapter 03. The Reward

Once we were at home, I still couldn't keep Stacy quiet. "When do I get my reward, Mistress Gail?" repeated every other breath. Constantly. Finally, after I had changed into my bedtime attire (a pair of 4-inch heeled mules, and a see-through short nylon robe, in pink, like my mules) and Stacy had stripped naked, wearing only a cock and ball harness, as was my requirement when I had nothing else in mind for him to wear, I gave in to his endless pleas.

"Okay, Stacy. I've been thinking of what I could give you for a reward. I've decided on your very favorite activity. How would you like to show me just how much you love me?"

"Oh, yes, Mistress Gail. That would be wonderful. Please let me show you."

"You remember how to do it, Stacy?"

"Oh, yes. I could never forget that."

As I settled back into my recliner, I said, "Okay, Stacy. You may begin." It was a ritual that I had taught him months earlier, but had not recently allowed it. I lit a cigarette and flipped on the CD player with some soft mood music.

Stacy tripped all over himself as he turned down the lights and lit several candles stationed around the room. Then, his Viagra induced hard cock preceding him, he placed a TV tray next to my recliner, and put a iced wine cooler beside it with a bottle of very expensive vintage wine (at his expense, of course) He poured a wine glass ¾ full and set it on the TV tray along with a penis whip and a riding crop.

Done with the preliminaries, he knelt at my feet and lifted my right foot, removed the mule lovingly, and started the ritual. He sucked each toe, beginning with the smallest, and as he moved from one to the next he kept repeating his mantra, "I love Mistress Gail. I love my Mistress Gail." He stayed at each toe until I signaled for him to go to the next by tapping his shoulder lightly with the riding crop. At the three-tap signal, he moved to the other foot and the routine continued. I allowed this foot worship to continue for almost an hour. Then a duo of three taps signaled Stacy to go to my pussy.

He gently spread my legs allowing room for his head between them, and began a worship ritual there that I allowed to continue until I had my seventh orgasm at the ministrations of his lips and tongue. A very hard slap on his shoulder with the crop told him to cease and rise, standing with his fingers interlocked behind him, his hard cock pulsing rapidly.

"Are you ready to fuck your Mistress?"

"Please, if it be you will. Mistress."

I replaced the crop with the penis whip and began slapping his cock unmercifully with it until I saw the tears in his eyes. "You have done well, sissy Stacy. You may fuck your Mistress now."

Without a word he knelt again, straddling my left leg. He placed his left hand at my pussy and began ministering to it very slowly as he humped my leg, rubbing his hard cock against the soft flesh of my calf.

"Not too fast, Stacy, dear. There's no need to rush. We have until morning, and it's only three am."

"Yes, ma'am." He slowed his pace, and slowly worked back to a steady rhythm. His mantra continued as he muttered "So good, so good, so good..."

After an hour and a half, I asked, "Do you want to cum, sissy?"

"Please, Mistress Gail. I need to cum so badly."

"Then you may."

He sprayed my leg with cum immediately, spilling some onto the carpet below. But he was quick. He bent down and lapped it up before I could scold him. Then, without command, he licked my leg clean.

"Would you like to do that again, Stacy?" Ritual, you know.

"Please, Mistress, may I fuck you again?"

"You have been a good sissy, so yes, you may fuck your Mistress again. But not the same leg. That one is satiated. Do you need my assistance in getting your cock hard again?" A stupid question, as it had not gone a bit flaccid, but still, ritual took precedence.

"Please, Mistress, help my cock get hard again." He stood between my legs, waiting, hard cock within a foot of my mouth. This was his real reward. I leaned forward and took his cock into my soft, moist mouth. I teased it the way I knew he loved, then took it all, even into and past my gag reflex, and deepthroated it.

When I heard him say, "Oh, my." I released it from my mouth and smiled sweetly at him. "I think you're ready now, Stacy.

We repeated the entire scene again with the toe sucking, followed by his humping my other leg until he came again, with results not unlike the first time. Cum on my leg, cum on the carpet, cum almost everywhere. When he had cleaned every drop away with his tongue, I stood, and as I walked toward the bedroom, I said, "I'll take my breakfast in bed this morning, Stacy. Bring yours as well, and we'll share a breakfast together as we sometimes do." He knew what that meant. He would bring mine on a lap tray, and his in a dog bowl, which he would consume on all fours beside my bed, lapping at it with only his mouth and tongue.

After breakfast, I went to sleep. Stacy had chores to do, so his sleep was delayed until the afternoon, after I inspected his work, and dry humped his ass for every error he made, real or not.

The poor man was exhausted when I finished my final humping of his as and sent him to his pallet on the floor beside my bed. I let him sleep, fixing dinner myself. Even a dish for him, which I left in the fridge for when he woke.

When he did wake, and as he was eating his dinner (at the table, since I was feeling generous) I sat across from him drinking a scotch on the rocks. "Stacy, I've been meaning to talk with you about moving forward in our relationship. What do you think about getting you some permanent tits?"

He spit the food in his mouth onto the table. "Wha... what?"

"Breast implants, dear. I think that's what we need to do next, so you can advance to the status of a girlfriend. You do want to be my special girlfriend, don't you?"

"Ye...yes, ma'am, I do. But... but breast implants?"

"Of course, Stacy. All my girlfriends have beautiful tits. Don't you agree?"

"Yes, they do," He admitted.

"And you just said you wanted to be my special girlfriend. I heard you very plainly. So shouldn't you have pretty tits, too?"

"I don't know..."

"Well, if you just want to continue to be my sissy, just say so." My tone was harsh.

"No. No, I do want to be your special girlfriend, Mistress Gail. But... tits?"

"Well, yes. Duh."

"Can I think about it?"

"Sure, sweetie. I don't need an answer until bedtime. Oh, just think, Stacy, when you're my special girlfriend, you can sleep next to me on my bed every night. We can do girl things together all the time. Won't that be fun?"

"I can sleep with you? On your bed, every night? And you won't treat me like a sissy anymore?"

"Yes, Stacy. On my bed, every night, except when I have one of my men friends over. And you won't be my sissy anymore." The last part of that was an outright lie, but we do what we need to do, don't we?

"Then... then, okay. I'll get some tits, Mistress Gail."

"Wonderful! I'll call my surgeon friend, Abigail, tonight and set up the procedure. I'm so thrilled that you want to be my special girlfriend, Stacy. I could just eat you up." I rose and circled the table, leaned over and kissed my sissy smack on the mouth, probing his with my tongue.

The rest of the day was unremarkable, except that I noticed an array of emotions ripple through my sissy as he contemplated his fate. Forty-something year old sissies can have the cutest smiles and the most awful frowns. And the looks of concern alternately opposed to the looks of delight amused me no end. I swear I could see the wheels turning in his sissy little head.

*

My, my, dear readers, what's happening here? Will Stacy actually go through with this new development? And what, exactly, does Gail have up her sleeve? Stay tuned for the next episode.