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Guided Double Dildo Masturbation Session

She directs his every stroke while she fucks both holes for him.

7 min read November 13, 2026New

The lamp threw a low gold over the sheets, and you were already naked when I sat down in the chair at the side of the bed. Cassidy, twenty-eight, long-limbed and flushed from the throat down, you lay with your knees bent and your thighs parted just enough that I could see the shine between them. Two dildos rested beside your hip, one thick and veined, one slimmer and smooth, both gleaming with oil. You kept glancing at them, then at me, hungry for a permission you hadn't been given yet.

I was thirty-two, comfortable in the chair, pants open, cock already hard in my fist. I stroked myself slowly, base to tip, and let you watch the way my hand moved. Your eyes locked on it the second I told them to. You could look. You could not reach. That was the bargain you'd agreed to with your voice steady and your fingers trembling, and I meant to keep every inch of it.

"Hands on the mattress," I said. "Don't touch those until I say so."

You obeyed. Your chest rose and fell. I dragged my thumb over the slick head of my cock and held it there so you could see the shine. Heat came off your skin in waves. Every part of you was mine to name, and the only pleasure you were going to take tonight was the kind I put into words.

"Wider. Show me."

You opened your thighs. Your pussy was wet enough to catch the light, and the tight little ring of your ass sat just beneath it, already flushed from the way you'd been thinking about this all evening. I stroked a little firmer and told you to keep your eyes on my hand. You did. The muscles in your stomach jumped. You wanted to crawl across the bed and take me in your mouth, and you weren't allowed to move an inch.

"Good," I said. "Stay right there and listen."

I made you start with your own hands. "Pinch your nipples. Not hard yet. Just enough to wake them up." Your fingers closed around the stiff peaks, and a soft sound broke out of you. I told you to roll them, to tug, to watch my fist while you did it. Every time my thumb swept the head of my cock, your hips gave a helpless little roll against nothing. "Lower. One hand on your clit. Circles. Slow."

You slid your fingers down through the wet and found that swollen bud. The first touch made your thighs shake. I watched you learn the pace I wanted, light and endless, never quite enough. "Tell me how it feels."

"Hot," you said, voice already fraying. "I'm so wet, Reid. I can feel it on my fingers. I want—"

"You want what I give you. Rub it. Don't stop looking at my cock."

You rubbed. I stroked in time with your hand, slow and mean, letting you see every vein, every bead that gathered at the tip and smeared under my thumb. Your nipples stood dark and tight. Your clit swelled under your fingers until you were panting, hips lifting off the sheet. I let you ride that edge until your breath went thin, then I stopped you with one word.

"Dildos. Now."

Your hand shook as you picked them up. "The thick one in your pussy. The other in your ass. Slow. I want to watch both of them disappear."

You notched the thicker head against your soaked entrance and pushed. It parted you inch by inch, and the sound you made was raw. Oil and your own slick made it easy, but you still had to work for it, thighs trembling, eyes glued to the slow pump of my fist. When it was seated deep, you reached for the slimmer one. I told you to lift your hips and breathe. You pressed it to that tighter hole and eased it in, whimpering when the widest part stretched you open. Both toys sank home. You looked wrecked already, stuffed full, clit throbbing untouched for a second while you adjusted.

"Fuck them," I said. "Slow. In and out. Describe it."

You drew both back and pushed them in together. The stretch made your mouth fall open. "My pussy's gripping it," you gasped. "It's so deep. And my ass—God, it's tight, I can feel them rubbing against each other inside me. Every time I push, it hits something that makes my legs shake."

"Again. Don't rush."

You fucked yourself in long, careful strokes while I stroked faster, the wet sound of my hand matching the wet sound of the toys. Your moans climbed. Your hips started to buck on their own, chasing the friction. A smaller orgasm rippled through you without warning—just a sharp clench, a broken cry, your cunt fluttering around the thick shaft while your ass squeezed the other. You didn't stop. I didn't let you.

"Keep going. Eyes on me."

You kept your gaze on my throbbing cock, on the fist you couldn't have, and another ripple took you, then another, little shocks that made your stomach jump and your voice crack. Each one made me stroke harder. Precum slicked my fingers. You watched it string between my thumb and the flushed head and whimpered like it hurt not to taste it.

"Please," you said. "Let me—"

"No. You come for my voice. You watch. That's all you get."

I sat back in the chair and opened my knees wider so you had nowhere else to look. My cock stood thick and dark in my fist, shining, and I worked it in plain view while you lay there stuffed and shaking, denied even the brush of my skin.

"Harder," I said. "Both of them. Pound that pussy. Pound that ass. I want to hear it."

You drove the toys in deeper, faster, the wet slap of them filling the room. Your tits bounced with every thrust. Sweat gathered in the hollow of your throat. I told you to alternate—three hard strokes in your cunt, then three in your ass, then both at once until your arms burned. You did it. The thick one plunged into your dripping pussy and came out glossy. The slimmer one worked your ass in short, brutal pumps that made your toes curl. Your eyes never left my hand.

"Rub your clit. Don't you dare look away from my cock."

Your free hand flew down. The second your fingers hit that swollen bud, your whole body jerked. I stroked myself openly, shameless, letting you see the way I squeezed the base and dragged up slow, then faster, matching the desperate rhythm of your hips. "You're going to come again. Loud. And you're going to keep those toys moving while you do it."

The orgasm hit you like a wave breaking. You screamed, back arching off the bed, both holes clenching so hard the dildos barely moved. Clear fluid gushed around the thick shaft and soaked the sheet under your ass. You squirted in hot little pulses, thighs shaking, voice gone ragged, and still I made you fuck yourself through it. "Don't stop. Again."

You sobbed and obeyed. The toys plunged. Your fingers ground over your clit in messy circles. Another climax tore through you before the first had finished, stronger, meaner, your pussy squirting again in a bright rush that splashed your wrist. You screamed my name. Your ass fluttered around the slimmer toy. I stroked faster, fist tight, the head of my cock dark and wet, and you stared at it like it was the only thing in the room.

"Look at what you can't have," I said. "Look at me getting close while you fall apart on plastic. Again. Harder. I want you shaking."

You pounded both holes, alternating until your arms trembled, then drove them in together and rubbed your clit in frantic little strokes. The third orgasm bowed you off the mattress. You convulsed, squirting in a long, helpless stream, mouth open, eyes wet and locked on my cock. Your tits heaved. Your stomach fluttered. The toys shone with you. I denied you every inch of me and made you watch every stroke—the twist of my wrist, the way my balls drew up, the thick pulse starting at the base.

"Eyes open," I growled. "Watch me come. Don't you close them."

I stroked hard and fast, right there in the chair, and let go. Thick ropes of cum shot over my fist, stripe after stripe, hot and heavy, coating my fingers and dripping down onto my thigh. I groaned through it, never looking away from you, and the sight of it ripped the last orgasm out of you. You screamed, convulsing, both dildos buried to the hilt, clit pulsing under your fingers, another rush of wet soaking the sheets while you shook and shook and couldn't stop. I kept stroking through the aftershocks of my own release, fist glazed and shining, and you watched every drop like it was a punishment and a gift at once.

You collapsed back onto the ruined sheets, spent and trembling, both toys still buried deep inside you. Aftershocks rolled through your thighs and made the shafts shift with every clench. Your chest heaved. Your eyes stayed on me, glassy and obedient, even when you could barely hold them open. I stayed in the chair, slowly milking the last thick drops from my cock, working them out over my cum-slick fingers while I looked at the mess I'd made of you.

"That's my good girl," I said, voice low. "You came so many times just for my voice and my eyes. You never touched me, and you still gave me every single one."

You would spend the rest of your life chasing the sound of a command you were no longer allowed to answer.

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