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Sissy Caption Story: Obedience, Desire in Pleasure

A Sissy‘s Lesson in Submission” follows the transformative journey of a submissive sissy, guided by a dominant partner named Miss. Under Miss’s firm yet nurturing hand, the sissy fully embraces her identity, leading to a life of self-discovery and fulfillment. Their intense and passionate encounters explore themes of dominance, submission, and pleasure, revealing the depth of their bond. Amidst the power dynamics, the sissy learns the consequences of disobedience and the importance of following Miss’s commands. The story explores their intense relationship, where obedience and punishment intertwine with desire and pleasure, culminating in a profound lesson in submission. Let’s enjoy this sissy chastity story.

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The Perfect Sissy Obedience

“Flawless,” I compliment, as I step into the room. “Such a good girl.”

Before me, you kneel exactly as I had instructed, demure and obedient. Your eyes remain cast downward, hands resting gracefully on your thighs, and a delicate collar adorns your neck. The little black dress clings to your curves, accentuating your enhanced feminine assets, giving you the appearance of a stunning sissy.

Enjoy Teasing the Sissy

As I approach you, I take control, gently lifting your chin to meet my gaze. Your eyes are drawn upward, and you can’t help but notice my ample breasts straining against my dress. Your breath catches, but you focus on pleasing me, submitting entirely to my desires. The look in your eyes tells me you’re all mine.

Softly, I press my lips against yours, savoring the moment. Then, I whisper into your ear, igniting your submissive desires even more. “You look like such a delightful little slut.”

Our lips meet again, this time with more intensity, and I feel your desperation and longing. As I pull back, I notice my lipstick smeared across your face, and it amuses me. I run my thumb across your lips, spreading the color even further. You obediently keep your gaze lowered, fully embracing your role as my submissive.

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Serving My Dominant Mistress

“Do you think you’ve been a good girl lately?” I inquire, my voice laced with dominance. I walk around, gathering various toys from our drawer, preparing for our intimate session. Your eyes remain downcast, but you respond obediently, “I’ve been trying, Miss.”

“Stand up,” I command. “Pull your dress up and your tights down.”

You comply, exposing your locked-up cock for inspection. I have you lie back on the bed, legs spread wide, and I observe with a little smirk. I wonder if you resent me for keeping it restrained for so long? A week can feel like an eternity.

“Pathetic,” I taunt. “Look at it. What am I meant to do with that?” Your face flushes with humiliation.

“Poor little penis,” I continue, adopting a mocking tone. “Has it been hard for you?” I gently cup your face with my hand.

“Yes, Miss,” you reply, slightly breathless.

“Oh dear,” I tease, maintaining the mocking tone.

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A Sensual Sissy Porn Story

I rise from my kneeling position and retrieve the key from the bedside table, holding it enticingly in front of you. “I think you’ve been a good girl,” I declare, a hint of satisfaction in my voice. “And you know I always keep my word.” With that, I unlock the chastity device, and you let out a moan of relief. I place a finger to my lips, signaling for you to stay quiet, and I gently stroke your hair, my teasing tone returning.

“There. Isn’t that better?” I inquire, enjoying the gratitude in your response. “Yes, Miss. Thank you, Miss.”

“Good girl,” I praise, savoring the power exchange between us. “You know, I think it needs a kiss better.”

I softly place my lips on the tip of your cock, and you cry out from the overwhelming sensation. Sensing your sensitivity, I take full advantage, slowly taking it deeper into my mouth, relishing every moan that escapes your lips. I skillfully swirl my tongue around the tip, prolonging your pleasure.

When I decide you’ve had enough, I instruct you to get up and bend over. Your eyes stay averted, but you feel the coolness of the lube on my fingers as they enter your tight little hole. The sensation causes more groaning, and I continue sliding my fingers in and out, heightening your arousal.

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Intimate Sissy Adventure

“Behold, my little sissy slut, a special gift for you,” I announce, my voice dripping with anticipation as I lube up the plug. I know you’re well aware of what’s coming next. With a deliberate motion, I insert the plug, then switch it on, watching with delight as the vibrations take effect. Your reaction is priceless, gasping and tensing from the delightful shock.

“Now, listen carefully,” I command, my dominance asserting itself. “Don’t you fucking dare cum without my permission. Understood?”

“Yes, Miss,” you obediently reply.

I position myself in front of you, spreading my legs, and you instinctively know what to do. With eager enthusiasm, you crawl forward, planting soft kisses along my thighs, making your way to my most sensitive spot. Your skillful tongue works its magic, and I let out a satisfied grunt as I press my wet pussy against your face, the vibrations of the plug adding to the pleasure.

But I have other plans for tonight. Roughly, I push you onto your back, a hint of aggression in my actions, and straddle you. I wonder if your cock will be too sensitive, if you can handle it. Curiosity drives me, and I slowly lower myself onto you. You whimper, your hands gripping my thighs as I pause to let you adjust. However, I don’t give you much time before I begin to move, savoring the sight of your pretty face as each thrust sends waves of sensation through you. I give you a playful slap, adding an element of pleasure-pain to our encounter.

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A Sissy's Pleasure and Pain

“Look at me, you fucking sissy!” I command, ensuring your eyes meet mine. “Take it for me,” I demand, my own moans of pleasure building as I increase the pace, thrusting and grinding against you, circling my hips with fervor. My hand finds its way around your throat, exerting gentle pressure as I dominate you in every way.

You begin to beg, your gasps and pleas begging me to grant you release. But I’m not ready yet, and so neither are you. Your pathetic whimpers only fuel my desire to make you wait, and with each plea, I reward you with a firm slap.

The anticipation becomes overwhelming for both of us. Your body tenses, and with one last desperate groan, your cock pulsates, unable to control itself any longer. You’ve cum, and you’ve cum early. As expected, that poor cock has been locked up for a week, unable to withstand the pleasure I’ve unleashed upon it.

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A Sissy's Lesson in Submission

Disappointment filled the air as I looked at you with a stern gaze, your face flushed with shame. I didn’t utter a word as I climbed off you and spread my legs, wordlessly commanding you to use your tongue to clean up the mess you had made. You knew exactly what to do, and with your submissive obedience, you diligently cleaned every drop of cum from inside me and down my thighs.

Without a word, I switched off the vibrating plug inside you but left it in place. I directed you to sit on a chair in the center of the room, securing your legs and arms with bondage tape. The silence between us was heavy as I fetched my dildo and laid back on the bed, indulging in my own pleasure. You watched intently, not daring to look away, as I moaned and thrusted until my orgasm washed over me.

Breathless and satisfied, I released you from the restraints, pulling you into my arms as we lay on the bed together, cuddling in the aftermath. A warm smile spread across my face as I knew you were relieved by the loving discipline you had received, reaffirming your place as my devoted and obedient sissy.

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