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“Wh-what… what do you mean?” I asked. I had thought the second lesson had to be me, well, coming—not anything painful. Hadn’t Cal said that?
I thought back, and realized that he hadn’t actually said that at all. He’d said that whipping and spanking weren’t the only ways to teach a lesson. He’d said that he’d teach me about my pussy and my little bottom.
He had let me think—hadn’t he?—that the second lesson would be his fingers finishing the orgasm they had made me long for so urgently.
Once again, he didn’t answer me with words. I felt his right hand move, his fingertips traveling from my right cheek toward the center of my ass. Then my eyes went wide and I let out a little cry of surprise and utter mortification as those fingertips spread my bottom cheeks and I felt the air on the tiny button of my anus.
My right hand struggled against his grip on my wrist. I tried to get my left hand up and around and back, but I found it up against Cal’s side, and then he’d seized it in his left hand and bent that arm so that he could gather both my wrists behind my back. All the while, his fingers held my ass open so that I knew he had a perfectly clear view of the little ring, the most private part of my body.
Heat surged in my face as I remembered what Jake had said the previous night about the right of the man in charge of me to touch me however he wanted… what Shelly had said about her bottom and the way it hurt to have her husband’s cock there… how scared she had been the first time Jake had told her he would fuck her in the ass. How it somehow felt good, even though it hurt.
I shook my head, rubbing my nose and my mouth against the scratchy wool, now that Cal had my hands behind me and I couldn’t cover my face with them.
“No… please…” I whispered.
“Shh, darlin’,” Cal murmured. “The lesson is just getting started. This little asshole is so sweet and pink and ready for training—just like your foster daddy told me.”
He took his right hand away and I let out a grateful whimper as I felt my cheeks close and cover my untried anus. I heard something from up above me, where his face must be though it seemed at the same time far away; a wet kind of sound. When his fingers came back to my bottom, I understood: he had moistened them in his mouth. He didn’t spread my cheeks this time; I felt his fingers on my pussy, and I cried out in relief, but that grateful noise trailed into a sharper sound of dismay as his thumb, wet with his saliva, pushed up against the tiny bud he had exposed.
I felt myself tighten against the pressure, my whole backside tensing to resist the inward movement of Cal’s invading digit.
“This will only hurt if you try to keep me out, Grace,” he said, raising his voice just a little. “It’s a lesson in submitting to the man in charge of you. If you don’t submit, my thumb is going into your butthole anyway, but it will be painful. If you do submit, though, you’ll start to learn what it means to give yourself to a man, the way you need to.”
I felt my face pucker into a mask of shame and woe. I could feel somehow in the involuntary movements of my brow and my nose how thoroughly conflicted I must look. At least Cal couldn’t see that expression—I took a tiny bit of comfort from that.
Him not seeing my face, though, didn’t make it any easier to deal with the conflict in my mind and my heart and above all my body. My hips jerked and my whole backside squirmed as I tried to keep pulling the tiny ring of my anus closed even as another part of me tried to make me push instead.
I had thought I had already experienced the maximum possible embarrassment, last night over the arm of Jake’s easy chair. Having Cal hold my most intimate places in his strong, skillful hand, though, seemed to make the fires of shame rise higher than my skin could even bear without literal flames licking along its surface—which was what it felt like as I pictured what he must be seeing: the lewd, rhythmic movements of my bottom and my thighs that despite everything I tried couldn’t do anything but appear to him to display my yielding and my submission.
Because they do display that, said an unwelcome but insistent voice in my mind. A gorgeous, good-natured guy took down your panties to teach you a lesson. He’s not even spanking you. All he’s asking…
I cried out, because Cal had started to force his way into my asshole with the moist ball of his thumb. I tightened even more as the pain shot through my lower body. Then, as quickly as the sensation had come, the pressure stopped.
“See, darlin’?” Cal asked, in the same slightly stern tone of voice he had used the moment before. “Let me in.”
The fingers up front, their tips on the hood of my desperately needy clit, gave a little rub, and to my mortification that was all it took. I let out a whining sob, and I arched my back and pushed in the most humiliating possible way. Cal’s thumb entered me, penetrating my bottom hole a full inch.
I gasped at the sensation, and I started to pant between parted lips because I simply hadn’t anticipated what it would feel like to have my anus invaded that way, then held open on a man’s thumb. To my surprise, it didn’t hurt at all: it felt good, though in a terribly shameful way, like the naughtiest, most wrong thing a girl could allow a man to do to her. Part of me thought, wildly, that I should receive a terrible whipping over the arm of Jake’s chair, simply because I had my suitor’s thumb in my ass.
“Good girl,” he said. “That’s it.”
I kept thinking I would get used to it: the strange, warm pride in my chest that brought an answering heat to my face—and also a dismaying, confusing echo down below. Cal reinforced that raging conflict, too, as if he were training a pet; he accompanied the little movements of his thumb in my anus with answering motion from his fingertips. Finally he gave my clit the friction I had so desperately longed for, and demonstrated just how much skill he had in giving this ambiguous kind of lesson.
I cried out and writhed over his knee. Each additional bit of tension in my muscles as he held me firmly in place with my arms bent behind me only seemed to add to the waves of pleasure and need crashing through my body. I struggled against his grip much more to feel how he could restrain me so easily than I did in any hope of breaking free.
“Oh… God…” I sobbed. “Sir… sir…”
I heard myself say it. I felt the word in my mouth, and it added to the shame, and to the heat, so greatly that my climax seemed to flow directly from it—from my following Cal’s instruction and calling him by his dominant title. My suitor, approved by my foster father to teach me about my pussy and my bottom… to train me to give him pleasure.
As I began to come, I felt suspended between Cal’s hands: the one on my back with my wrists in its grasp, holding me down while the other fondled me in the lewdest, naughtiest way between my legs and my bottom cheeks. The pleasure exploded outward from my pussy to seize my whole body, and it took away every bit of my control over my thoughts, so that I pictured myself on my knees in front of Cal. I pictured myself nuzzling the front of his jeans… I heard myself begging him the way Shelly had begged Jake, to let me take out his beautiful penis. My suitor had started to train me, and what else would my training be for than to make me ready to serve his rigid cock?
I came and came, because Cal made me keep riding his caressing hand, sobbing and moaning, to orgasm after orgasm. Through it all, he murmured to me, encouraging me in a patronizing way that seemed to multiply the pleasure as it increased the heat of the continuous blush in my face.
“There you go, darlin’. Good girl. Come for me. Get on my hand, now. That’s it. So nice and wet and ready.”
Ready. That word seemed to shoot through me with its own jolt of need. It brought on the biggest of my orgasms, and I screamed as my backside surged backward and forward, desperately milking all the pleasure my pussy could find on Cal’s knowing fingers.
He moved his hand, just as I had begun to think that the pleasure had become a punishment, and felt my whole body shudder with irresistible need for more anyway. He squeezed firmly, one final time, as if to make absolutely sure I knew how thoroughly he had just taken possession of my most private places, then he pulled his fingers away and started to rub gentle circles over my whole backside. I lay limp over his knee and sobbed at the comforting sensation as his palm soothed my right cheek, then my left cheek, then the back of my right thigh, then the back of my left thigh, methodically, it seemed, helping me down from the top of the cliff of endless arousal he had perched me on.
