Page 77 of Shamefully Trained

He held me for one suspended second after that, folded and open and burning with humiliation.

Then he withdrew.

The emptiness in my pussy made me gasp. Before I could process it, I felt the blunt, slick pressure of him lower, farther back, at the small, tight place that had brought so much dread, and helpless, mortifying need, for the last few days.

My whole body went rigid.

“No,” I whispered, though I knew exactly how weakly it sounded.

His thumb stroked once over my clit, not enough to soothe, only enough to remind. “If you behave yourself,” he said, “and let me into this little bottom properly, you may play with yourself while you’re getting it. I may even let you come.”

I made a broken sound. The promise itself was humiliating. Permission to touch myself while he did this to me.

He began to press.

The insistence of that heavy hardness at a place so much smaller, so much more frighteningly intimate, made panic flash through me. I tried to pull away though there was nowhere to go, no way to close myself.

“Please,” I sobbed. “It hurts.”

“Yes,” he said.

He pushed a little farther. Fire opened at my rear in a thin unbearable line. I cried out and my hands flew to the bedspread, clutching at nothing.

“It hurts,” I said again, uselessly.

His voice remained calm, even. “You need to learn that your sponsor’s pleasure matters more than your comfort.”

Something in me split then, the same strange division that had happened before under too much sensation, too much command. Part of me stayed there in the bed, sobbing and exposed and being slowly opened by his cock. Another part drifted upward and away, cool and observant and horrified by its own clarity.

Because from that detached place, his words made a terrible kind of sense.

He supported me now. He housed me. He fed me. He cared for me in the severe, impossible way that was his. The arrangement existed for his pleasure as much as for my survival—more, if I was being honest—and if this was what pleased him, then of course I must take it. Of course I must let him use this part of me too. What had the training yesterday been for if not this? What had the lessons, the plug, the words, the shame, the orgasms, been preparing me to accept?

The reasoning slid into me almost as inexorably as he was trying to. I heard myself sob once more, deeply, from somewhere far below that detached rationality.

Then I stopped fighting. I simply let go of the muscular refusal, let my body cease arguing with the fact of him. The little ring of muscle yielded by fractions. His cock entered farther. The stretch grew wider, hotter, almost blindingly intense.

“There,” he said, and I heard the approval in his voice. “That’s better. Let it happen, you sweet little ass girl.”

CHAPTER 24

Porter

The sight of my rigid cock vanishing into Alex’s adorable virgin bottom enraptured me. The delicate, dainty, wrinkled inner lips of her thrillingly smooth pussy glistened with her need just above where my hardness now entered her. The same copious wetness coated my rigid shaft from my ride in her velvet vagina, lubricating me as I opened the tiny button of her anus.

The bunched lace of the pretty white thong, just a soaked strip of fabric now, lay to the side, running along her outer lips and over her pert little bottom cheek. The garter belt, suspenders, and sheer stockings framed my conquest of Alex’s pussy and bottom beautifully. Little by little I impaled her on my phallus, taking my time to fill her most private place with this new lesson, her sopping panties simply moved aside for her sponsor’s convenience in fucking his new bed girl in cunt and anus.

“Touch yourself,” I said, my voice a little rougher than I intended. “Show me what your sponsor’s cock in your ass does to that little cunt.”

She made the sweetest, most stricken sound, and then obeyed. Her fingers went between her legs, hesitant at first, as if the act of granting herself pleasure under my order still shocked her almost as much as the submission that had earned it. I kept my hands on her upper thighs and kept her wide open for me while she began to stroke herself, and the desperate sexiness of the sight brought a jerk to my cock.

She raised her face a little from the bed and looked down her body, stealing a naughty glimpse of how my penis had claimed her and how her fingers worked her clit, trying to make it feel good. I saw shame in her eyes, certainly. No girl with any pride would look otherwise while taking a man’s cock in her bottom and rubbing her own slick little sex because he had told her to.

But I could see something else in her expression too. Gratitude. And, even more movingly, a fragile bright thread of pride, as if she understood that she had done something difficult for me and had been found worthy of reward.

Her face struck me with absurd force at that moment. I had told myself I was managing this: structuring the way I introduced her to these dark pleasures, keeping my own emotions within the bounds of what I could command and explain and pay for. But the sight of Alex Murphy with my cock in her ass, touching her pussy because I had decided she had earned it, raising her eyes to look at me as if my approval mattered in some deeper way than the simple terms of an arrangement—it didn’t seem like the kind of sight a prudent man would allow to assume real importance in his mind or his heart.

But it occurred to me with a disorienting urgency that I was losing the fight not to love her.