Page 14 of Shamefully Trained

If I hadn’t come so close to climax already, I would have giggled at the fact that the hugely endowed man in my imagination refused to end a sentence with a preposition.

I was so close to the edge already that the shift from one fantasy to the other hardly mattered to my body. If anything it sharpened everything. I could feel the sting across my ass in anticipation, the humiliating spread of my own wetness, the knowledge that he would punish me and then make me hold still and take more.

His hand, maybe… his firm, open, enormous hand. Falling over and over on my naughty bottom.

My free hand slid over my stomach and behind my hip, almost by accident. Then further… lower.

I hesitated only a second before letting those fingertips stray between the cheeks a horrible man had whipped with his belt… and a wealthy, kind-but-demanding man might spank with his open hand, the way a paternal figure teaches a girl the lesson she’s earned.

The touch there, in the middle, on the tiny button, jolted me. I had barely ever done more than wash myself there—never mind touched like that… on purpose. The sheer strangeness of it sent a fresh hot shiver through me. I pressed gently, not inside, only circling the tight little place while my other hand kept rubbing my clit in quick desperate motions.

In my imagination Porter noticed at once.

Not there, Alex. Not yet, you dirty little whore.

The words came to me as if spoken right against my ear, and I moaned aloud because what followed them in my mind was even worse: his hand parting me, his fingers testing, assessing, deciding what I would be made to learn. The line from his profile flashed back at me with humiliating vividness. Anal training… important part of your life.

I nearly came just from the thought of him saying, very calmly, that he was going to fuck me there.

I pressed my fingertips more firmly against my forbidden back entrance and shuddered. My whole body felt overfull, over-sensitized, as if every nerve had been stretched tight. I imagined him making me lie still while he spread me open with lubricated fingers… not rough or careless… simply inexorable. I imagined the unbearable embarrassment of it, the way he would watch my reactions as if they interested him only insofar as they told him how to proceed.

You’ll take it in the ass. You’ll learn.

A sobbing little sound escaped me. I rubbed my clit so hard it almost hurt, and behind that pain I pictured one finger pressing into me, then easing farther while I squirmed and tried not to. I imagined him holding my hip down. A second finger later, after I had been made to breathe and submit and stop clenching around the intrusion. I could practically feel the stretch of it in my own body though nothing had touched me there but my own timid fingertips.

I wanted to stop. I wanted to sit up, pull my hand away, and remind myself that I was alone in my apartment masturbating to the fantasy of a man I had never even met—because some app had shown me a few sentences about discipline.

Instead I slipped the tip of one finger just barely inside my asshole and cried out into the dim room.

The sensation was too strange to call pleasure, and yet it poured directly into the desperate ache between my legs. I took my finger out at once, panting, then touched the place again, rubbing there while my other hand worked at my clit with near-violent insistence. In my mind he was the one making me endure it, telling me to hold still while he prepared me because if he intended to use that part of me, he would not ask it to happen all at once.

Then, in my mind’s eye, came the plug.

I had seen them, of course, in online shops and funny videos. In my fantasy the one Porter trained me with was sleek and menacing and much too large, held up for me to see before he pushed it into me inch by patient inch while I trembled and tried not to cry. The very thought made my thighs shake. I imagined the humiliation of being made to wear it afterward while he corrected me for touching myself, each stroke of punishment landing while I was stretched and full and unable to forget for even a second what he had put inside me.

I rubbed myself nearly raw on that image.

My hips bucked helplessly. I could feel sweat at the back of my neck, beneath my breasts, the lace sticking damply to me. The orgasm was so close, but it seemed to hover just out of reach, maddeningly delayed by the very intensity with which I chased it. I imagined him removing the plug and telling me that now I was ready. I imagined the heat of embarrassment as sharp as any pain, the profound vulnerability of being opened that way for a man who had decided my body should learn obedience from him.

When I pictured the first pressure of his huge, hard penis against my asshole, I nearly screamed.

It was impossible that the thought of that much pain and exposure and possession should send me over, and yet it did. Not the moment of penetration, even… the moment of impalement… but the moment before: his hand firm on my back, my body held where he wanted it, the low certainty in his voice when he told me I was going to take him where only a man like him would know how to take me.

I came with my hand mashed between my legs and my other palm clapped over my mouth too late to catch the sound. Pleasure broke through me in hot violent pulses, threaded through with shame so intense it almost made me dizzy. My whole body clenched. Even the place I’d touched at my rear tightened reflexively, and that only made the aftershocks stranger and more humiliating. I rode it out in jerking little motions against my own hand, sobbing once through my fingers.

When it was over, I lay still for a few seconds, stunned.

The room returned in pieces. The cheap bedside lamp. The rumpled comforter under me. The phone lying nearby with Porter B.’s profile still open, that photograph of his severe mouth and silvered temple looking back at me as if he knew exactly what I had just done.

“Oh, God,” I whispered.

My pussy throbbed painfully. I had rubbed myself hard enough that the lace and my fingers both felt abrasive now. Between my cheeks there was still a faint ghost of the touch I had dared, enough to make me flush all over again as I realized what I had been imagining in such detail. Not just being spanked. Not just being ordered around. Trained. Opened. Taken.

By a stranger.

I sat up too fast and had to close my legs against a fresh after-pulse. My hand looked damp and indecent in the lamplight. I wiped it on a towel furiously, as though anger could undo what had happened.

It couldn’t, obviously. I had just masturbated in lingerie to the idea of Porter B. whipping me for touching myself and then teaching my body to accept him in the most intimate, humiliating way I could imagine.