By the time Aunt Sissie’s done giving me my due, I’m stupid with endorphins. When I rise from the desk bearing a shit-eating grin, she merely raises an eyebrow before pointing to my corner.
“Diddle but don’t dally,” she warns me. “And keep it in your pants, for Pete’s sake.”
I’m such an idiot at this point that I merrily trot over to the corner and don’t even wait for her to leave the room before I start masturbating. Ah, what a rush, rubbing my clit while it still smarts from getting slammed. It throbs in my hand at first touch, ready for more sensation, and as I work it, I peek into my pants and see that it isn’t really raw—any more than my ass is really blistered—but the reality doesn’t negate how unbearably sensitive it is now.
I know as I stand there in the corner, I’m doing what Aunt Sissie’s more typical customers do. I know her clients are mostly men—straight men who hunger for punishment and who, when they receive it, must relieve their poor, aching cocks. That Aunt Sissie treats me like the men who visit her should insult me, but it doesn’t. It’s deliciously humiliating, getting lumped in with all the guys, and I grow wet thinking about it as my stroking takes hold. I feel like an incorrigible boy who has one last clandestine chance at naughtiness. My stance stiffens. I straighten, as if my height is my erection. It’s habit; I always do this in my corner. It helps me come.
And then a blinding strike of pain shoots across my ass. Aunt Sissie! But she’s never here for this part—she never watches me wank! I turn just enough to see she has a ruler in her hand—a long, slender metal ruler. And its every blow is pure, raw sting, a pain so strong I choke on the sudden lump that’s leapt into my throat.
“You liked that earlier paddling too much,” she tells me. “It can’t be corrective if you haven’t suffered.”
I abandon my clit and place both hands against the wall to brace myself.
“Did I tell you to stop masturbating?” she yells at me.
“No ma’am,” I manage to mutter.
I touch myself and resume my duty. Proper posture becomes a distant memory as I slouch forward, weakened from the ruler’s bite. I’m rendered dull by Aunt Sissie’s severity, and that cruel, vicious implement; as it sounds against my ass, tears well in my eyes.
Pleasure rising from within, yet pain blazing from without confuses me, and I cannot focus. Though I yelp at each biting sting, though I’m slick and swollen, I discover a new threshold: I can’t come. Ass aflame, cunt engorged, I rub my clit harder and faster. I grow desperate for orgasm, but I’m choking on pain that’s stronger than I can bear.
I try, I try, I try…and I can’t. I can’t complete Aunt Sissie’s final task and, finally, I admit defeat. I whimper, I sputter, I squeeze the words from my throat: “I can’t come.”
Abruptly, the ruler stops its assault. Except for my soft cry of regret, all is quiet.
I do not move until she tells me to.
“Get your clothes. We’re done.”
Tears clouding my vision, I fumble toward my clothes. I’m heartbroken that I couldn’t do as commanded, that she’s going to send me home, swollen, wet, and wanting. Failure shames me.
But just as I’m ready to step into my pants, Aunt Sissie pulls my boxers down one last time and inspects my ass. “Such marks! Won’t your friends down at the gym love this! Be sure you don’t hide it from them.”
I freeze, stunned by what she’s voiced. She knows this? How? Isabel! Isabel told her this! She took my most sacred routine and made it illicit. She turned it into biting gossip for Aunt Sissie to throw in my face. Conspirators, they are conspirators!
I leave, compromised and humiliated beyond compare. Just as the paddle didn’t invoke the right contrition, masturbating in the “boys’ corner” didn’t impart the right humiliation. Neither could do its job because I enjoyed it too much. And so, the ruler and the words. Together, they shamed me. Thoroughly.
That’s what I realize as my ass burns against the seat of the crosstown bus. That’s what stays with me as my every step aches when I walk home from the bus stop. And when I reach our abode, I just stand there on the sidewalk, unable to move forward, void of sass and saturated with defeated.
The knowledge that Isabel gossips to my auntie makes me want to cry, and I wonder if it will prove more humiliating than I can bear. I wonder if, thus broken, I will ever see my auntie again?
Finally I move, and as I walk up the steps and into Isabel’s warm arms, I pray my human foibles have not fled me. I pray my shortcomings will continue to give me reason to return to my dear Aunt Sissie. Because I want her touch. Because sometimes, only it will do.
DETENTION
Jai T.
The room reeks of used pussy. The kind of stench that emanates from a woman’s cunt in the heat of June. Pungent and musty. She’s worn and deflated. I’ve left her with only my favorite tie and those menacing heels. It’s the last day of class and I’ve waited incessantly since the first time I saw her swagger into the room. To smell her pussy. To ingest the smoke of this cigarette. Deep, greedy inhales. Slow, suspended exhales. Imitating the way my clenched fist entered and emptied her.
She’s Dr. Lynn Stone, PhD. Through years of schooling, she’s mastered the study of women. Through years of waking up in strangers’ beds, so have I. Philosophical Perspectives on Sex, Gender, and Love every Monday and Thursday night from 7:15 to 9:30. She’s either sitting on her desk, legs crossed and covered in black leather boots that disappear into black hip-hugging skirts or pacing around the classroom with inviting heels from the blackboard to the door, up and down the mob of wide-eyed students eagerly waving their hands with the answer, begging to impress her. My eyes are permanently fixed on her, except when she scans the swarm of us. Then I’m the androgynous boi in the back of the room, slouching down in my seat, sketching explicit thoughts of her sitting on her desk, legs uncrossed and uncovered, wearing only skin and the residue of my mouth. I know all of the answers. I could tell her everything she wants to hear but I just sit there instead, detached and isolated, pining for the fantasy.
She’s the kind of teacher you think about after class, wondering what she does with herself when she’s not reading a highlighted passage from an essay or discussing feminist theory. I don’t think I was the first of Dr. Stone’s students to get off thinking about her naked body in some compromising position with myself at the helm, and I doubt I’ll be the last. Don’t get me wrong, Dr. Stone was not your typical girl next door teacher turned porn star with one toss of her glasses and a sway of newly untamed hair. She’s brilliant, self-assured and great at what she does. She’s classy. A woman. A woman who, in my mind, however, I had no problem turning into a dirty, filthy whore insistent on being fucked. In class, she was a self-identified feminist with an arsenal of fashion magazines in her bag and a history of prom queen titles and old pom-poms from her cheerleading days—all stories that surfaced during class discussions on sex, gender, and love. Stories that always included ex-boyfriends, though that never dissuaded me. Him or her never mattered—lately it was just me and Ms. Stone. Dr. Stone. The woman crowded my mind.
It’s Thursday night. I’m walking to class. I’m sweating. The air still hangs heavy at quarter past seven in the summertime. It gets trapped between the buildings piled on top of one another, brick against brick. I’m intentionally running late. I like to make an entrance. Collar up. Make her notice. When I get there and find a seat it’s obvious that the air conditioner is broken. It’s sweltering but I’ve decided I don’t mind. Now, the only thing humming lies neglected between my legs. My head is teeming with thoughts of fucking her. Fisting her and sucking on her perfect, pierced nipples; gnawing on her sore, reddened clit; masticating her buzzing flesh. These are the thoughts reeling between my ears as I slowly drift back to what sounds like a conversation on masculinity. I inadvertently catch her eye, immediately sit up in my seat, open my book to the page we’re apparently reading from, loosen my stifling tie and divert my eyes to my desk.
I’ve tolerated most of the semester this way. Not being able to get her out of my head long enough to get into the work, I’ve been managing to fail the class and have yet to turn in a paper, worried that if I can even sit still long enough to think about something other than that body she occupies and turn something in, she’ll still be able to read right between my lines, and through them to my agenda where sex separates every letter and inhabits the spaces between my deliberate SAT words. I need to do things to her and be things to her that the authors of the essays we’re reading completely and utterly condemn.
It’s the last day of Sex, Gender, and Love. I had to drag myself back here, fooling myself into believing that if I didn’t show, Dr. Stone would have to remain there in room 601 until I decided to pull myself together and make my final appearance. How else would I get my final back? She would have to wait for me. Standing alone in a perfect cliché, wearing painfully high heels, fishnets, and a blouse that falls accidentally off of her shoulder allowing the strap of her black bra to peek out while she impatiently watches the clock tick seconds away, vehemently inking papers in the same cherry red as the panties she has on to pass the excruciating minutes without me. However, as I make my way back to reality and inside room 601, feeling the gaze of an entire classroom that has just been rudely interrupted by some slacker who thinks it’s okay to waltz in twenty minutes late, I realize Dr. Stone will wait for no one—not even her most adoring schoolboi.
Dr. Stone sits at her desk with a pile of papers in her hands, our finals—mine cleverly entitled “Ladies and Gentlemen: The Semantics of Dismantling Gender.” I hope she realizes that I put my heart and soul into those pages. Studying every assignment she had given out from the first day of class in one caffeine-addicted sleepless night, I set out to put my most uncompromising thoughts to paper in eleven insomniac induced hours. I wanted her to think back on the past three months and come to the undeniable conclusion that I, the slacker who always waltzed in late and hid behind my desk, had actually been teacher’s secret pet all along.
Dr. Stone calls us up to her desk one by one and I begin to realize that I’m a stranger to everyone in this class, having used my senses only to detect her alone. One after another, they approach her desk, glance at the letter adorning their papers, smile to let Dr. Stone know that this was by far the best class of their academic careers, and proceed to the door, leaving it all behind. I sit at my desk in total disbelief at how easy they make it all seem, and impatiently wait my turn. The room empties slowly, leaving only the two of us and a sea of vacant desks at last. Seconds pass, then minutes. I can see my name on the edge of her lips and mechanically begin to approach her. “Dr. Stone,” I say finding my voice somewhere deep inside of my body, looking down at her behind the desk.
She plants her hands down on the desk, standing up and meeting me at eye level, and pulls me to her by my black silk tie. She bites her lip and in a raspy voice only a schoolteacher in your wildest fantasies could have, “I’ve decided. I’m gonna call you boy. Now get back in your seat, boy. Now.” I instinctively about-face and go back to my desk. I hear the door lock and the knock of her heels against the floor, where my eyes are presently fixed. I glance from her black high heels up to her thighs and then back down again. “Don’t be shy,” she teases and I can’t help but smile. “Do you like what you see?” She lifts one leg and lands her foot hard on my desk, confining me.
“Yes,” I mutter.
“Yes, ma’am,” she demands, and I submissively correct myself.
“Yes, ma’am,” I repeat.
“Good boy,” Dr. Stone commends me as she bends down, her blouse inappropriately unbuttoned and flaunting a sexy black bra. “Sit tight, boy,” she whispers.
She goes back to her desk and returns hiding something behind her back.
“I’ve got a surprise for you, boy. Hold out your hands and close your eyes.” I sit in silence wondering if I’ll find myself engaged in a conversation about gender roles when the room reappears, but instead her throaty voice warns, “Say please.”
“Please,” I appease her. “Please, ma’am,” I indulge. She grabs my wrists from behind and ties them to the back of the desk. I smell her close.
“I’m gonna make you all mine. You’re gonna do every damn thing I ask.” She mounts me and hauls her skirt up, revealing tiny black panties that seep up her ass and barely cover her messy, wet cunt. She’s rubbing her pussy between my hips, riding the cock she doesn’t yet know I’m wearing. She teases me with her lips, bringing them to mine, pursed and slightly open, draped in red, seducing me. My mouth begs as she retracts. Another “Please” escapes me. This time unsolicited.
“I’ll be such a good boy,” I plead.
She leans in and asks, “Do you always want what you can’t have?” I recklessly unfasten her blouse with my teeth and feed on her hard, rutted nipples. Her arms are strung over my neck and she’s saddling my legs, riding me like a seesaw. She’s unrepentant. Shameless. Greedy. She unwraps her legs from around my waist and slides off of me, leaving my eyes on her full, round ass. She bends over from her waist dragging the fold in the lips of her slick cunt. She strips off her skirt, arming herself with only a G-string and agonizing heels.
“You want to smell what you’ve done to me boy?” One leg at a time, her panties come off, and she tosses them at my face and struts back toward me making eyes at my tie.
I react flagrantly, “I bet you like the way I wear it.” I smirk, continuing, “I bet I’d like the way you wear it better.”
“Don’t get fresh with me, boy,” she banters, stomping her heel against the floor, insisting I play my part.
“Pretty please, Dr. Stone,” I persist as the progress I’ve made toward untying my wrists tips in my favor.
With my hands no longer constrained I begin to disentangle my tie. She looks at me with a devious grin.
“I’ve been a bad boy,” I confess, and feel the power shift. “Sit on my lap and I promise to make it up to you.” With her bare ass up against my jeans, I trace her skin with the silk of my tie, shadowing her curves. She’s restless. I run my tie up the crack of her ass, between her swollen tits and dangerously around her neck, then mask her eyes with it and she doesn’t protest. I escort her over to her desk, lagging a step behind to watch the way the heels force her ass to bounce from side to side. Taking hold of her at her hips, I lift her up onto the desk, and watch her spread apart from the knees. I unzip my pants and take it out through my boi briefs and slide it between her fold. Rub it up and down between her lips to get it wet—to tease her—to show her just how long and thick it is when I finally put it inside of her, her limbs fall malleable and heavy. She’s tight like a virgin so I disappear slowly inside of her. I can tell teacher’s pussy is sopping wet from my cunt-soaked cock greasy with her insides when I pull out. She drags me back in so I release a little more and repeat—inside and out of her with the lips of her pussy slapping and sticking against my cock. I can tell she’s close, with the end of her heel pressed into my back, her long legs circled around me. I leave her empty this time instead and help her off of the desk. With my hand on her head, I force her knees crashing to the floor until she’s leaning back, sitting on her feet, her hands cradled in her lap. I drop my cock across her lips, holding it in one hand. Her tongue follows behind tasting what she’s left of herself on all nine inches.
“Suck me off, Dr. Stone.”
“Yes, boy,” she concedes and starts to swallow it, sucking at it violently with a mouthful between her cheeks. There she is, Dr. Stone on her knees, stuffed nine inches deep—this time between the teeth—her tits knocking against me when she’s full. She looks up with obedient eyes and I help her up off of the floor. She’s pressed against me with the smell of rank cunt and cock emanating from our skins. I turn her around, pulling her ass toward me, her hands landing out in front of her on the desk, bending her in half. I slip it in her ass.
She grunts, “I bet you didn’t know I liked it up the ass, boy. Was
I always a slutty bitch in your filthy, muddy mind? Fuck me from behind, boy, isn’t that what you want?” I lean forward over her, my bound tits pressed up against her back, and whisper, “I’ll jerk off in your ass if that’s what you want, whore. Then I’ll come inside to show you how I really feel.” I spread her even further, kicking out her heels with my shoes. She’s stretched out over the desk throwing her ass at my cock, her tits burning from the brutal back and forth friction.
“More,” she wants. One finger at a time I begin to penetrate her until her holes are filled with every extension of me. I’m making use of her, she’s thrashing with pain and pleasure as I feel her body suddenly constrict around everything she has inside of her. She’s silent. Expulsion. She comes, dismissing each appendage until she’s empty and only herself again.
I wipe her scum off each inch and put it back in my pants. She unapologetically gathers her clothes from around the classroom.
Back in the dizzying humidity, only seconds have passed. “There’s one last thing I wanted to give you, Jai,” she says handing me my final paper back. I nod, weighty and unable to move. “Well aren’t you going to look?” she asks.
I tell her, “It doesn’t matter.”
“I thought it didn’t,” she responds dejectedly and walks out of the room like just another one of her students would.
I strike a match to ignite the tobacco between my lips wanting the smell to be unfamiliar this time on my fingertips and the rim of the cigarette. Disappointed, I fill my lungs with smoke and nicotine and think to myself, It feels good to be occupied. I thumb through the pages she handed back, landing on the last one, which is adorned with a few words of wisdom, a mark penned in red and her name.
Nice job on this, you showed potential. Maybe you should have asked for a little one on one with me—it could have helped. My door was always open.
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