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Sissy Academy, Part 4: Strap-On Hour

By Aria Wilde · Sissy feminization erotica · 8 min read · part 4 of 10

Thursday

You spend Thursday morning not thinking about it so hard that you drop a teacup in the staff room. It shatters on the parquet and every teacher turns to look at you, and Madame Celeste says, "Ah. Thursday," and they all laugh, and you want to die.

At lunch nobody gives you anything to eat. Nurse Ivy gives you a glass of water and a small enema bag instead and walks you to the bathroom and waits outside the door, humming.

"Clean as a whistle," she announces afterwards, as if you have passed an exam. "In you go."

The practice room

The practice room is on the top floor, under the eaves. The ceiling slopes. There is a low padded bench in the middle of the floor, with leather cuffs at the four corners, and a long mirror propped against the wall in front of it so whoever is on the bench can see their own face.

Miss Vale is already there.

She is wearing the jodhpurs and the riding boots and nothing on top but a black sports bra. The harness is strapped tight around her hips. The pink shaft juts from it, thick and glossy and absurdly long, and she is slowly stroking lube along it with one hand, the way you might oil a tool.

"Strip to the cage and the stockings," she says. "Leave the heels. Bend over the bench."

You do it. You are getting very good at doing things.

She cuffs your wrists. She cuffs your ankles wide apart. She steps back and looks at you from behind for a long moment, and you can see her in the mirror, looking.

"Lesson one," she says. "A sissy is not a person who gets pegged. A sissy is a hole that is grateful. Say it."

You say it. Your voice shakes. She makes you say it again until it doesn't.

Lesson one

She starts with her fingers. She is quicker than Nurse Ivy and not as kind: two fingers, then three, twisting, stretching, a thumb hooked against the rim. She makes you count each breath out loud and push back against her hand on the out-breath, and if you lose count she stops, slaps your bottom hard enough to leave a mark, and makes you start again.

By the time she lines the head of the strap-on up, you have counted to sixty-one and your cheeks are wet and your cage is dripping steadily onto the bench.

"Look in the mirror, Lacey. I want you to watch your face when you become a girl."

The pink shaft glides deep inside your tight, trembling hole, stretching you open until your back arches and your locked cage leaks a fresh, heavy drop onto the leather bench. You feel every inch of her thick, glossy cock pushing against your walls, a warm, insistent pressure that makes your toes curl inside your high heels. "Look at your face," Miss Vale commands, gripping your hair to keep you bowed over the mirror as she slows down, grinding the head of the strapon against your sensitive rim. In the glass, you see your own red-lipped mouth gasping, eyes wide and wet, watching yourself open wide for her. "You're so greedy," she whispers, laughing softly as she starts to piston in and out, long and slow strokes that make your inner muscles clamp around her smooth surface. The wet slap of skin against skin echoes in the small room, mixing with your ragged breaths and the damp drip from your caged tip.

Miss Vale picks up the rhythm, deeper and harder now, her hips snapping against your bare ass with rhythmic force. "That's it, Lacey," she growls, her hand tightening in your hair to pull you back toward the glass as she thrusts her pink cock deep inside your stretched hole. You can feel how tight your body is around her, how desperate you are to take more, how your locked cage leaks steadily with every powerful drive. "You're pushing back like a good girl," she says, her voice low and dirty, watching the way your face scrunches in pleasure and pain as she keeps you bent over, stretched out. The mirror reflects your messy hair, your glistening skin, and the way your own eyes watch yourself surrender completely to her control.

"You're such a slut," Miss Vale murmurs, increasing the speed of her thrusts until you're moaning loudly, your hips meeting hers in a wet, rhythmic grind. "Feel how hard you are for me, feel how good it feels to be used like this." The pink shaft pounds deep inside your stretched hole, stretching you again and again as she grips your hips and keeps your face fixed on the glass. Your cage drips constantly now, a steady stream of clear fluid marking every time she bottoms out, coating the leather beneath you. "Look at yourself," she commands, her breath hot against your ear as she drives into you with relentless, expert precision. "See how open you are, see how much you love being filled by a woman." You're moaning like a broken doll, pushing back against her strong arms, your hole clenching around the thick pink cock that claims every inch of your inner depth. "There she is," Miss Vale says to the mirror. "There's our girl."

The doorway

You don't see Aria come in. You only see her appear in the mirror, leaning against the frame of the door with her arms folded, the key glinting at her throat.

Miss Vale does not stop. If anything she goes deeper.

"How is she?" Aria asks, as if asking after a horse.

"Tight. Greedy. Noisy." Miss Vale punctuates each word with a stroke. "Learns quickly."

"Mm." Aria crosses the room in no hurry and crouches in front of the bench so her red mouth is level with yours. She looks at your wet, ruined makeup with deep satisfaction. "Hello, Lacey. Are you being a good girl for Miss Vale?"

You try to answer. What comes out is not a word.

"I'll take that as a yes." She takes your chin in her fingers. "Faster, please, Vale. I want to see what she does."

Miss Vale increases the tempo until your back protests, her pink strap-on piston driving in with brutal, metronomic force against your overstretched hole. "Look at the water you're making," she commands, smacking your fleshy buttocks hard enough to sting and leave red welts. Your head thrashes wildly, but Aria's grip on your chin remains iron-tight, making your face upward so she can study every twitch of your expression. "You're already leaking before you even hit the edge, aren't you?" Aria whispers hotly against your jawline, her dark eyes locking onto yours as she watches the clear fluid gush through the pink bars of your cage.

The relentless pounding presses a heavy, concentrated pressure against your prostate, sending electric jolts racing down your spine that make your legs tremble uncontrollably. With every deep thrust from Miss Vale, another jet of warm fluid streams out, dripping onto the leather beneath you in rhythmic spurts. "That's right, feel how much you love it," Aria coos, her voice dropping to a filthy growl as she leans closer, her breath fanning over your damp neck. "Your little sissy cock is pulsing so hard it's practically overflowing, isn't it? A wet, happy mess for us women to play with."

Suddenly, the pressure becomes too much; your locked cage erupts into a hands-free, continuous drip as you are overwhelmed by a soft, relentless sissygasm without any release. Your hips buck involuntarily against Miss Vale's punishing rhythm while tears blur your vision and shake your entire body in a fit of pure, exposed pleasure. Both women laugh loudly at the sight of your chaotic surrender, their voices echoing off the walls as they continue to use you, ignoring your shaking form completely. "So deliciously undone," Aria murmurs, pressing her thumb gently against your wet cheek. Aria wipes a tear from your cheek with her thumb and says, "Again."

Thank you

They take turns.

Afterwards you could not say how long it went on. The light in the attic window goes from white to gold to grey. At some point Aria puts on the harness herself, a smaller, darker shaft, and fucks you lazily and very deep while describing in your ear exactly how pathetic you looked the day you arrived. At some point Miss Vale pushes her own wet fingers into your mouth and makes you suck them clean. At some point you stop crying and start begging, and then you stop begging and simply say thank you, over and over, at every stroke, because that is the only thing left in you.

Aria buckles on the harness and lies back on the padded bench, the dark shaft standing up from her hips. "Up you get, Lacey. Ride." She taps your hips with a sharp staccato rhythm that echoes against the locked pink bars of your cage. Miss Vale steps in behind you and grips your hair. "Ready for your final ride?" Aria whispers, lifting your hips until you hover over her, your locked cage swinging against her skin, and then she pulls you down.

The sensation is immediate and overwhelming as you sink all the way down onto her, the dark shaft filling your stretched hole while Aria thrusts upward to meet you and Miss Vale holds your hair to keep your face up. Your small pink cock slaps wetly against Aria's stomach with every upward bounce of your pelvis, clear fluid leaking through the narrow openings of the cage to mix with her sweat. "That's it," Aria commands, squeezing your thighs hard enough to bruise as she groans at the sight of you bouncing on her. "Feel how your hole stretches for me! Feel how much you love being used by your teachers!" Miss Vale leans forward, biting the curve of your neck while Aria pounds up into you in a brutal, circular motion that forces your spine to arch higher and higher until your toes curl in your heels.

The dual pressure becomes a relentless hurricane, your overstimulated hole twitching wildly as warm droplets stream uncontrollably from your cage onto Aria's bare stomach. "Thank you for every inch," you gasp, your voice hoarse from hours of use, as Aria increases the speed until your legs tremble so violently they threaten to give out. "Clench for me, Lacey! Keep it tight around my shaft!" Aria yells, lifting her hips and driving deeper with the harness, her own breath ragged against your ear. "Faster! Faster! You're mine to break apart completely!" With one final, ferocious thrust, your body gives out entirely, your hole gaping wide open as your mind dissolves into pure, empty exhaustion, leaving you dangling on the edge of total collapse. When she finally lifts you off, you fold onto the floor at her feet and kiss her boot without being told.

Aria laughs softly and rests the toe of her boot on your cheek.

"Look at that, Vale. She's started doing it on her own."

"They always do," says Miss Vale, unbuckling the harness.

Aria crouches one last time. The key swings from her neck, close enough to touch, and you don't even try.

"You've done very well, Lacey," she says. "Your body has learned. Next week we teach your mind." She taps your temple with one red fingernail. "Friday is the Red Lips Exam. You'll take it in trance, on my couch, with all the staff watching. Nobody has ever passed it the first time." She stands. "Get some sleep. And listen to your headphones tonight. Very, very carefully."