Memories - Total Possession
During dinner, shielded by the dim candlelight of the bistro and the comforting hum of other diners, I could almost pretend I was just a girl on a date with a handsome, older man. But here, in the quiet, masculine expanse of his penthouse, the reality of what I was, and what I was doing, hit me with the force of a physical blow.
I stood in the center of his living room, my heels sinking slightly into the plush rug. I felt ridiculous. No, that wasn't the right word. I felt exposed.
I was wearing a soft, grey long-sleeved sweater and a short, green plaid skirt; a "schoolgirl" look, because Brad had mentioned during our coffee date that he had a weakness for the aesthetic. Underneath the skirt, my legs were encased in sheer, nude stockings that caught the light of the floor lamps. And hidden away, crushed beneath layers of tight spandex and lace, was the part of me I was trying so hard to forget tonight. I could feel it pulsing, a frantic, rhythmic swelling every time Brad took a step closer. It was a traitorous reminder of the body I was born into, even as I worked so hard to mask it.
"You've been quiet since we left the restaurant, Sara," Brad said, his confidence in stark contrast to my mood.
He didn't move to take off his blazer. He just stood there, leaning against a bookshelf filled with leather-bound volumes, watching me with an intensity that made my knees weak. He looked like he was cataloging every tremor in my hands.
"I... I'm just taking it all in," I whispered. My voice sounded small, the pitch carefully modulated to stay in that feminine register I'd practiced for months. "Your place is very nice."
"It's a place for grown-ups," he said, his voice a low, smooth vibration. "But you don't look like a grown-up tonight, do you? You look like a nervous little girl who's wandered somewhere she doesn't belong."
I flushed, the heat creeping up from my collar and staining my cheeks. I reached up, nervously fingering the black bow I'd tied into my blonde hair. "I wore what you asked for. I wanted to please you."
"And you do," he murmured, finally moving. He walked toward me with the slow, predatory grace of a man who knew exactly how much power he held. "But you're shaking again. Why is that, Sara? Is it because you're afraid of me, or because you're afraid of how much you want to stay and see what I can do to you?"
I looked down at my shoes, unable to hold his gaze. "I'm just... this is all very new. I mean, not this, not dressing like this, but...for a man. I told you, I've always considered myself straight. I date women. I was married. I like being a boy in the real world."
Brad stopped just inches from me. I could smell the expensive scotch he'd had after dinner and the faint, clean scent of his skin. The proximity made my heart race, and that dull, cramped pulse between my legs intensified. It was a humiliating sensation to feel so much desire for a man while dressed as the very thing I claimed I didn't want to be.
"A straight boy," Brad repeated, his voice dripping with amused skepticism. He reached out, his hand surprisingly gentle as he brushed a stray lock of hair behind my ear. "A straight boy who spends three hours on his makeup? A straight boy spends money on high-end stockings and a skirt that barely covers his hips? A straight boy who goes home and cries because he has to take off the dress and can't be Sara?"
The accuracy of his words felt like a knife. I tried to pull back, but his other hand came up, firm and unyielding, to cup the back of my neck. "I... it's just a hobby. A fantasy," I stammered, my eyes beginning to sting. "It doesn't mean I'm... that I'm like this."
"You are like this, Sara," he countered, his voice hardening into a command. "You think you want a woman, but that's just the script you were handed. You don't want to be the one holding the girl, that's not you, it will never be you; you want to be the girl being held. You want to be looked at the way I'm looking at you right now. You want to be told what to wear, how to sit, and exactly how you belong to a man."
"No," I whimpered, even as I leaned into his touch. "I'm not... I'm not gay." I could barely get the word out.
Brad chuckled, a dark, knowing sound that vibrated against my skin. "That's what you all say. It's the last little bit of pride you cling to. 'I'm not gay,' you all say even as you spend hours dressing so pretty to please a man. But look at you. You're tucked so tight it must be painful, yet I can feel you trembling. You're desperate for me to see through the your boy mask and find the little sissy underneath who just wants to be used."
The word 'sissy' hit me like an electric shock. It was a word I only let myself think in the darkest, most private corners of my mind. Hearing it from him, in this room, made my legs give way. I would have fallen if he weren't holding me up.
"Tell me the truth, Sara," he whispered, his face inches from mine. "When you were in the bathroom at the restaurant, checking your lipstick in the mirror... were you thinking about the girls you used to date? Your unsuccessful marriage? Or were you thinking about how it would feel to have a man like me push you against this wall and remind you exactly what you are?"
The honesty was a physical weight, crushing the air out of my lungs. I closed my eyes, a single tear escaping and tracking through my foundation.
"I was thinking about you," I confessed, the words a broken surrender. "I was thinking about how much I wanted you to like the skirt. How much I wanted you to find me pretty. How much I wanted you to... to take charge." The words tumbled out so fast I couldn't believe I said them.
"Because you're a girl," Brad said, his voice a hypnotic thrum. "Tonight, you aren't a boy, you aren't 'straight.' You're just a pretty, obedient little sissy in a plaid skirt who's finally found her place. You've spent twenty-six years pretending to be a boy, pretening you didn't fantasize about men, and look how tired it's made you. Wouldn't it be easier to just let me decide everything for you?"
I nodded slowly, the movement heavy with the weight of my realization. The conflict that had been tearing me apart for years seemed to vanish in the face of his absolute certainty. He was right. I was exhausted. I didn't want to be strong anymore. I didn't want to lead. I wanted to be the one who was led.
"Yes," I breathed, my voice finally losing its tremor, replaced by a soft, aching need. "Please. Just... tell me what to do."
Brad smiled, a slow, triumphant curve of his lips. He let go of my neck, his hand sliding down my arm to grip my wrist.
"Good girl," he murmured, and the heat that flared through me at those words was unlike anything I had ever felt with a woman. "Now, turn around for me, Sara. I want to see how that skirt looks from behind. I want to see exactly how much of those stockings you're showing off for your date. I want to see how pretty, how sexy you dressed for me."
I turned slowly, the heels of my pumps pivoting on the rug. The short, pleated fabric of the skirt flared out for a second before settling against my thighs. Standing there with my back to him, facing the wall of leather-bound books and the dark reflection in the window, I felt a new kind of vulnerability. It wasn't just being seen; it was being appraised. He was looking at me like a predator looks at prey.
"Stay right there," Brad said. I heard the soft click of his glass hitting a coaster. "Don't move a muscle."
I froze. I could hear my own breathing, shallow and rapid. Behind me, I heard the rustle of his suit jacket as he stepped closer. The air seemed to vibrate with his presence. I looked at my reflection in the glass of the window, the blonde hair, the delicate bow, the soft curve of the grey sweater. I looked like the girl I'd always seen in my head, but the pulse between my legs, cramped and insistent against the tight spandex of my transformation, was a frantic reminder of the truth.
"The way that plaid sits on your hips," he murmured, his voice so close now I could feel the heat of him. "And the stockings, so sheer. They have that perfect, subtle sheen under these lights."
"I...I like stockings," I said.
"Did you wear them for you or for me?" he asked. "Did you wear stockings because you like stockings or because I told you I liked stockings?"
I swallowed. "For...for you," I said.
"Hmmmm," he said, and I felt his breath against the nape of my neck, right below my hair. "You're wearing exactly what a girl like you should be wearing. It's funny, isn't it, Sara? A man would never be caught dead dressed like this. A man spends his days talking about sports or his job, trying so hard to be 'one of the guys.' But here you are, standing in my living room, shivering because a man is looking at your legs."
I squeezed my eyes shut. "I...I'm still a boy," I said, "it's part of me."
He chuckled. "You're a sissy and that's the only part of you that matters right now," he countered. I felt his hand, large, warm, and heavy, land on my waist. His thumb hooked just over the waistband of the skirt. "You keep saying you're 'straight,' but a straight man doesn't feel this much relief when another man takes the lead. A straight man doesn't tuck himself away so tightly just for the chance to be called 'pretty.' Sissies do that. Sissies dress to please a man. Sissies dress wondering what it will be like when a man touches them."
"It...it's just a hobby," I lied.
He leaned in, his lips brushing against the shell of my ear. "Tell me, Sara. Does it feel like a hobby right now? Or does it feel like you've finally stopped fighting a war you were never going to win?"
I couldn't lie anymore. Not to him. The physical sensation of being tucked, the dull, constant ache of being compressed, was usually a source of private shame. But with Brad's hand on me, it felt like a badge of office. It was the proof of my submission. I felt a surge of arousal so sharp it made my head swim, that traitorous pulse swelling even harder against the lace.
"It feels... like I've stopped fighting," I choked out.
"Good," he whispered. "Because you're not a boy on a date with a man. You're a sissy who's been playing a character for twenty-six years. And tonight, the play is over. You don't have to be a boy with me, you won't, trust me. You can just be my beautiful, obedient sissy."
His hand slid from my waist, his fingers trailing down the back of my thigh, the rough skin of his palm catching slightly on the delicate nylon of my stockings. The sensation was exquisite. I felt a sob catch in my throat, not of sadness, but of pure, overwhelming release.
"Brad," I breathed, my knees beginning to buckle. "I...please..."
"Shhhhh," he commanded, his hand tightening on my thigh to steady me. "I didn't give you permission to speak. You're going to stand there, and you're going to listen to me tell you exactly how this night is going to go. You're going to learn that your only job is to look beautiful and do exactly as you're told. Do you understand, Sara?"
"Yes," I whispered, the word a total surrender.
"Yes?"
"Yes, Sir," I added.
The word hung in the quiet of the apartment, more permanent than any of the legal documents I spent my days filing as a boy. It felt like a heavy, velvet curtain had dropped between me and the rest of the world. Out there, in the streets of the city, people were living normal lives, adhering to the rules I had tried so desperately to follow. But in here, under the weight of Brad's hand, those rules had been set on fire.
"Sir," Brad repeated, his voice like a low-frequency hum that vibrated through the soles of my feet. "I like the way that sounds coming from those red lips. It suits you, Sara. Much more than any of those lies about being a 'straight' or not being gay."
He didn't let go of my thigh. Instead, his fingers began to move, tracing the delicate, welt of my stocking, finding a garter straps, touching it, snapping it. The sensation was agonizingly slow. I was hyper-aware of everything: the way the waistband of my plaid skirt dug slightly into my stomach, the stiffness of my own posture, and the frantic, rhythmic throb of my pulse, the part of me I had so carefully hidden, now swelling and straining against the thin, punishing silk of my panties. It was a physical contradiction I couldn't escape; I looked like a schoolgirl, but I felt the raw, undeniable electricity of a man's desire.
"Look at me," he commanded.
I turned back around, my legs feeling like lead. My face was flushed a deep, shameful crimson that even my expensive foundation couldn't hide. I looked up at him, my eyes wet and wide. He was so much broader than me, so much more certain of his place in the world. He hadn't even taken off his tie, and the formality of his appearance made my own costume feel even more scandalous.
"You're so desperate to be seen," Brad said, his eyes scanning my face with a clinical, yet burning intensity. "You put on this hair, this makeup, this skirt, the stockings. You spent hours crafting a vision of a girl. But you were terrified that if a man actually looked, he'd find the boy underneath and laugh. Isn't that right?"
I nodded miserably, my lip trembling. "Yes, Sir," I said, "I... I thought it was a joke. I thought I was just... playing."
"It's not a joke now, is it?" He reached out and caught a stray tear with his thumb, smearing it across my cheekbone. "When you feel that pulse between your legs, knowing you're tucked away, knowing you've given up your power to me... does that feel like a joke?"
"No, Sir," I whispered. I felt a surge of heat so intense I thought I might faint. "It feels... real. More real than anything else."
"Because it is real, Sara," he said. He stepped even closer, forcing me to tilt my head back until I was looking straight up at him. "The 'straight boy' you pretend to be is the joke, Sara. He's a suit you wear to work. But this? This soft, trembling, obedient sissy in the skirt? This is who you've been starving for twenty-six years. And I'm the one who's going to feed her."
His hand moved from my face down to my chest, his palm resting flat against the grey sweater. My heart was a frantic bird beneath his hand. He could feel it; he could feel exactly how much control he had over me.
"You're pulsing," he murmured, his gaze dropping to the front of my skirt. "I can see the tension in the fabric. Even through the stockings and the nylon, you're reacting to me. Tell me, Sara... what does it feel like to be a girl who wants a man this badly?"
"It feels... humiliating," I confessed, the words spilling out of me in a rush of honesty that felt like a physical relief. "It feels like I'm losing everything I thought I was. I feel so small. I feel... I feel like I'm nothing."
"You are nothing," Brad agreed, his voice dropping to a dark, possessive growl. "You're my nothing. You're a pretty little sissy who's finally admitted that she doesn't want to be a boy. You don't want to lead. You don't want to decide. You want to be used, and you want to be told that you're a good girl while it's happening. You're a sissy who's abandoning the illusion of being straight, walking to the reality you need to serve a man."
A soft moan escaped my throat before I could stop it. The shame was there, thick and heavy, but the arousal was winning. The 'straight' boy was a ghost now, a fading memory of a person I no longer recognized. I looked at Brad's strong, masculine hands and all I could think about was how much I wanted them to claim every inch of me, to strip away the last of my pretenses and leave me as nothing but Sara.
"I am a good girl," I whispered, the words tasting like nectar and poison all at once. "I want to be your good girl."
Brad's smile was predatory, triumphant. He reached down and took a handful of the plaid fabric, bunching it up in his fist. "We'll see about that. A good girl doesn't just say the words. She lives them. She accepts her place. She understands that from this moment on, her only purpose is my pleasure and my convenience."
"Yes, Sir," I whispered.
He leaned in, his nose brushing against mine. "Do you understand, Sara? The boy doesn't live here anymore. Only you do. And you belong to me."
"I understand, Sir," I breathed, my eyes closing as I finally let go of the last.
"When you belong to me, my pleasure matters, not yours. You pleasure doesn't come from what's between your legs, Sara, it comes from serving me."
Brad released the bunched-up fabric of my skirt, letting the pleats fall back into place against my trembling thighs. He didn't move away; instead, he stepped back just enough to sit on the edge of the couch, his legs spread, his presence filling the space between us.
"Kneel," he commanded softly. "A girl in a skirt like that shouldn't be standing when a man is talking to her."
I didn't hesitate. My knees hit the plush carpet with a soft thud, the sheer nylon of my stockings sliding against the fibers. Looking up at him from this height, the power imbalance was absolute. I felt tiny, a doll dressed up for his amusement, my blonde hair spilling over my shoulders.
"You're wondering when I'm going to touch you, aren't you?" he asked, his voice conversational, almost cruel in its lightheartedness. "You're waiting for me to reach under that skirt and acknowledge the mess you've made of yourself."
I bit my lip, my eyes darting to his hands, large, capable, and currently resting idly on his knees. "I... yes, Sir," I manage to admit.
"But that's the thing, Sara," he said, leaning forward until his face was inches from mine. "A man doesn't touch a sissy like that. Not where you want it. That part of you... it's a vestige of a life you're leaving behind. It's a distraction. If I touch you there, I'm acknowledging the boy, and we've already established that the boy is dead tonight."
The rejection stung more than a slap. I felt a surge of desperate, cloying need. My body was screaming for the very contact he was withholding. The ache of being tucked so tightly was becoming a roar in my ears, a rhythmic pounding that demanded release, but Brad was looking at me like I was a piece of art he was deciding whether to keep or discard.
"So," he continued, his fingers reaching out to toy with the black bow in my hair, "if you want to feel anything tonight, you're going to have to find it elsewhere. You're going to find it in the way I look at you. You're going to find it in the way you serve me. You're going to find it in the frustration of knowing that no matter how much you ache, I won't permit your hands to yourself, and mine certainly won't."
"Please," I whispered, the word escaping as a broken prayer. "I'll do anything. I just... I want to feel you."
"You do feel me, Sara. You feel my voice. You feel my commands. You feel the shame of being a sissy, of being exactly what you are," he murmured. He stood up, towering over me once more, and reached out a hand, not to pull me up, but to tilt my chin toward the bookshelf. "Pick a book. Any book."
I blinked, confused. "Sir?"
"You're a schoolgirl tonight, aren't you? Then you should be studious. Pick a book, sit at my feet, and read to me while I finish my drink. And Sara?"
I looked up at him, my heart in my throat.
"If I see you shift or try to ease that tension between your legs even once, the night ends, the wig comes off, and you go back to being that tired, lonely 'straight' boy. Do you understand?"
The threat was more effective than any physical restraint. The idea of losing this, of losing Sara, even this humiliated, aching version of her, was unbearable.
"I understand, Sir," I said, my voice steadying with a new, dark purpose.
I reached for a heavy volume on the bottom shelf, the movement making my skirt hike up even further. I didn't care. I sat back on my heels, the book heavy in my lap, and began to read, my voice a soft, feminine melody in the quiet room. I was a sissy in a plaid skirt, denied the touch I craved, existing only to fill the silence for the man who owned me. And for the first time in twenty-six years, I didn't feel like I was pretending.
"Stop reading," he commanded.
I went silent instantly, the book trembling in my lap. I felt his hands slide over my shoulders, his thumbs tracing the line of my collarbone through the soft grey wool of my sweater. Then, his hands traveled downward not toward my waist where I was desperate to feel him, but to my arms, pinning them to my sides as he leaned over me.
"You're making it very hard for me to focus on the text, Sara," he whispered into my hair. "All I can hear is the way your breath hitches every time I move. All I can see is the way these stockings catch the lamplight when your legs quiver. All I can see is the desperate sissy."
He let go of my arms and reached around, his fingers grazing the very top of my thighs, right where the sheer nylon met the lace of my garter belt. He didn't go further. He just traced the line of the elastic, the friction sending jolts of lightning through my nervous system.
"You're so tight, aren't you?" he murmured. "Wrapped up like a present you aren't allowed to open. Tell me, Sara, what does it feel like to be so close to a man, dressed like his fantasy, and know that you're absolutely forbidden from finding relief?"
"It... it hurts, Sir," I gasped, my head falling back against his legs. "It's a good hurt. But I'm so scared."
"Good. That 'hurt' is your new reality," Brad said. He moved around to the front again, but he didn't sit. He reached into his pocket and pulled out a small, silk scarf, deep emerald green to match my skirt. "Blindfold. Put it on."
I took the silk, my fingers clumsy. As the world turned into a soft, green-tinted darkness, my other senses exploded. I heard the clink of ice in his glass. I heard the slide of leather as he settled into his chair.
"Now," he said, his voice sounding like it was coming from everywhere at once. "Crawling toward me. Slowly. I want to hear the sound of your stockings on the rug."
I moved on all fours, the hem of the plaid skirt riding up, the cool air hitting the skin of my lower back. The sensation of the carpet through the nylon was agonizingly erotic, each fiber felt like a tiny needle of pleasure. I reached his shoes and stopped, my forehead resting against the polished leather of his oxfords.
"You want to touch me, don't you?" Brad asked.
"I..." I hesitated, not because I didn't want to but because I was afraid to admit it.
"Be honest," he comanded.
"More than anything," I whimpered.
"Then do it. But remember the rule. You use your hands, your lips, your heart, but you don't use the boy. You don't even think about him. You serve me as Sara, or you don't serve me at all."
I reached up, my hands finding his knees, feeling the heavy fabric of his suit trousers. I began to work at his laces, my blindfolded world narrowing down to the texture of his clothes and the sound of his breathing, which was finally beginning to sharpen.
I felt his hand land on the back of my head, his fingers tangling in the blonde strands of my wig, tugging just enough to make me moan.
"You're doing so well, Sara," he growled. "A perfectly obedient, perfectly frustrated little sissy. Now, show me exactly how much you've forgotten about being a man."
The silk blindfold pressed against my eyes, turning my world into a hazy, emerald-tinted void where the only anchors were the scent of leather, scotch, and the heat radiating from the man in front of me. My fingers, trembling and clumsy, found the cold metal of his belt buckle. The clack-clack of the prong releasing sounded like a gunshot in the quiet penthouse.
As I slid the leather through the loops and lowered his zipper, my heart wasn't just racing, it was trying to beat its way out of my chest. I reached inside, my hand brushing against the fine cotton of his boxers before finally closing around him.
He was thick, so hard, searingly hot, and pulsing with a life of his own.
A wave of pure, unadulterated horror washed over me. "What am I doing?" the voice of the 'straight boy' screamed in the back of my mind. "This isn't who you are. Men don't do this" But as the thought formed, my fingers tightened instinctively, exploring the velvet-smooth skin and the rigid strength of his erection. The horror was immediately swallowed by a tidal wave of thrill, a jagged, electric realization that this was the missing piece. All the years of pretending, all the failed dates with women where I felt like I was reading from a script... it all evaporated. This was the lead I had actually wanted to follow.
"You feel that, Sara?" Brad's voice was a low, possessive rumble above me. I felt his hand return to my head, his fingers threading through my blonde hair, anchoring me to his lap. "That's the reality you've been running from. You aren't disgusted. You're fascinated."
"I... I am, Sir," I whispered, my voice breaking. I was kneeling there, my stockings stretched taut over my thighs, my plaid skirt bunched around my hips, holding a man's cock in my hands and feeling more like a woman than I ever had in my life.
"Now comes the part where you stop being a spectator," Brad commanded. His grip on my hair tightened slightly, directing my face closer. "I know you're scared. I know you think this is the line you can't cross and still go back to your old life. But we both know that life was a lie. You want to taste me. You want to know what it's like to have a man completely fill you."
I swallowed hard, the scent of him, musky, clean, and masculine, filling my lungs. The "straight" world was a thousand miles away. I leaned forward, the silk blindfold slipping slightly, my lips finally brushing against the velvet tip of him. "Yes, Sir," I said, an admission of defeat.
"Go on, then," he said.
I leaned forward, tongue out. I tasted the salt, the faint, sweet tang of the precum already beginning to bead at the crown. A soft moan escaped my throat, vibrating against his skin. It wasn't the sound of a boy; it was the sound of a girl who had finally found her purpose.
I opened my mouth, my red-painted lips stretching to accommodate him. As I took him in, slowly at first, the heat was overwhelming. The friction of my tongue against him, the way he filled the space I hadn't known was empty, sent a surge of arousal through me that made my tucked, aching core throb with a renewed, desperate intensity.
I felt his hips shift, a low groan of approval escaping him as I began to move.
In that moment, I knew. Even if I ever put on a suit again, even if I tried to play the role of the husband or the boyfriend to a woman, the memory of this would be burned into my soul. I could never go back. I wasn't a boy who "happened" to be doing this; I was a sissy who belonged on her knees. The schoolgirl in the plaid skirt had finally learned the only lesson that mattered: how much she loved to serve.
"Good girl," Brad hissed, his hands moving to my shoulders, pinning me into place as I lost myself in the rhythm of his pleasure. "Take it all, Sara. Show me exactly how much you need this."
The rhythm of the room shifted, the silence replaced by the wet, rhythmic sounds of my own surrender and the heavy, ragged hitch of Brad's breath. The blindfold made the world a tight, emerald-tinted sensory chamber where the only thing that existed was the heat of him and the desperate, aching need to be exactly what he wanted.
Every time I moved, the fabric of my green plaid skirt brushed against his knees, and the sheer nylon of my stockings felt like it was fused to my skin. I could feel the friction of the carpet beneath my knees, a constant, grounding sting that reminded me of my position. I wasn't the boy in the suit tonight; I wasn't the one making the decisions. I was a girl on her knees, learning that her voice was best used not for arguments, but for the soft, muffled sounds of devotion.
Brad's hand tightened in my hair, his knuckles grazing the back of my neck. The pull was firm, commanding my rhythm, forcing me to take more of him than I thought I could. But I did. I opened my mouth and let him fill it with his cock.
"That's it, Sara," he growled, his voice vibrating through his thighs and into my chest. "Don't think. Thinking is for a boy. Just feel. Feel how much you want to please me. Feel how much you love the taste of your own submission."
The 'straight' boy I had spent twenty-six years building was dying. He was a shell, a costume that had finally been outgrown. As I felt the salt and the heat of him, a realization crashed over me like a breaking wave: I had never been this present in my own life. Not once. Every date with a woman, every "manly" thing I'd done, had been a performance for an audience that didn't exist. But here, under the weight of Brad's hand, there was no performance. There was only the raw, undeniable truth of my nature.
I felt the pressure build in him, the tension in his thighs radiating into my hands. My heart was thundering against my ribs, a frantic, rhythmic echo of the pulse between my legs. Even though I was tucked away, even though I was forbidden from touching myself, the pleasure was radiating through my entire body. It was a total, systemic collapse of my old identity.
He reached for the blindfold, removed it. "Look at me," he commanded, his voice sharp.
I stopped, my lips still glistening, my eyes were wide really seeing his cock for the first time. Then I looked up, saw the burning intensity of his gaze.
"You're never going back, are you?" he asked, a triumphant edge to his voice. "You can try to put the suit back on tomorrow. You can try to talk about sports. But you'll always know. If you're ever with a woman again, you'll know. You'll always feel the ghost of my cock in your mouth and the ghost of this skirt against your legs. You're mine now, Sara. Not just for tonight. You've found your center."
I couldn't even find the words to argue. I didn't want to. I leaned back into him, my body a map of his desires. The fear was gone, replaced by a terrifying, beautiful clarity.
"Yes, Sir," I breathed, the words thick with the evidence of my service. "I'm yours. I'm just... Sara."
He didn't say anything more. He just pulled me closer, his hands sliding down to my waist to pull my hips flush against his legs, making sure I felt every inch of the power he held over me. The night was far from over, but the war inside me was finally won.
The room seemed to shrink until there was nothing left but the sound of my own frantic breathing and the heavy, rhythmic thrum of Brad's pulse against my lips. I focused entirely on the taste of him and the way his hands were now gripping my shoulders with a bruising intensity.
I didn't need to see his face to know he was close. I could feel the tension radiating from his core, the way his muscles corded under his trousers. Every instinct I had, the ones I'd spent a lifetime suppressing, told me to move faster, to give him everything. I used my hands to steady myself against his thighs, the nylon of my stockings whispering against the fabric of his suit as I adjusted my weight, deepening my rhythm, his cock moving in and out of my mouth.
"That's it, Sara," he rasped, his voice breaking into a dark, guttural growl. "Don't stop. Don't you dare stop now. Sissies do not stop."
I took him deeper, first looking at him then at his cock. The sensation was overwhelming; I was a girl, I was a sissy, I was a vessel for his pleasure. The 'straight boy' didn't just feel like a memory, he felt like a lie I had finally stopped telling. As I felt the first hot, heavy surges of his release, I didn't pull away. I swallowed, taking every drop of his dominance, letting it become a part of me.
The silence that followed was heavy, broken only by our ragged breaths. I stayed there, his cock in my mouth, my forehead resting against his knee, my body trembling with a mixture of exhaustion and a strange, crystalline euphoria.
It took several minutes for him to soften and I wouldn't let go, almost afraid if I did I'd never have it again. Finally, he pulled back, looked down at me, his hair slightly disheveled, his expression one of absolute, calm victory. He reached out and smeared a thumb across my ruined lipstick, his touch almost possessive.
"You see, Sara?" he whispered. "You survived the truth. And you loved it."
He sat back, watching me as I knelt there in my disarray, the blonde hair messy, the plaid skirt hiked up, the stockings shimmering under the floor lamps, the taste of him fresh on my mouth.
"Now," he said, his voice returning to that smooth, commanding tone. "Since you've been such a good girl, I think it's time we discuss how we're going to make sure you remember this when you wake up tomorrow."
Brad's hand slid from my cheek to the back of my neck, his fingers hooked into the collar of my sweater. He didn't pull me up; he kept me right there, small and yielding at his feet. The weight of what I had just done, the taste still lingering on my tongue, felt like a brand. It was a physical mark that no amount of soap or water could ever truly scrub away.
"You're thinking about tomorrow," he said, reading my mind with terrifying accuracy. "You're thinking about the moment you have to put on a pair of slacks, and pretend you didn't spend the night on your knees for a man, when you pretend you weren't a sissy doing what she was meant to do, suck cock."
"I... I have to go to the office," I whispered, my voice sounding breathy and fragile.
Brad chuckled, a dark, knowing sound. "Oh, you'll go. But you won't go back to being him. Not entirely."
He stood up and walked over to a small mahogany chest near the window. When he returned, he was holding a small, delicate object that glinted in the light. It was a simple black velvet ribbon, identical to the one in my hair, but attached to it was a small, discreet silver charm.
"Turn around," he commanded.
I obeyed, my black pumps clicking softly as I shifted my position. I felt his hands move my long blonde hair aside, exposing the nape of my neck. He wrapped the velvet ribbon around my throat, tying it snugly, not tight enough to hurt, but just enough that I would feel it with every swallow, every turn of my head.
"This stays on," he murmured, his breath hot against my ear. "Under your dress shirt tomorrow. You'll feel the velvet against your skin all day. Every time a colleague speaks to you, every time you file write something, you'll feel this ribbon, and you'll remember the weight of my hands on your shoulders. You'll remember the taste of me. You'll remember that the 'boy' they see is just a shell for the sissy I own."
He leaned over, pressing his lips to the spot just behind my ear.
"And because you were so obedient," he continued, his hand sliding down to the waistband of my plaid skirt, "I'm going to let you stay tonight in my bed. You'll sleep in those stockings. I want you to feel the nylon against the sheets. I want you to wake up and see those sheer legs and remember exactly what you are before you even open your eyes."
I let out a shaky breath, my eyes fluttering shut. The idea of carrying this secret into my "real" life was terrifying, yet it was the most erotic thing I had ever heard. I wasn't just Sara in this room anymore; I was Sara everywhere, hidden just beneath the surface, waiting for the next time he called.
"Yes, Sir," I whispered, leaning back against his legs. "I'll wear it. I'll remember."
"Good girl," he said, finally pulling me up to my feet. "Now, let's get you to bed. You have a long day of pretending ahead of you, and I want you to be well-rested for the next time you come back to me."
As he led me toward the bedroom, the hem of my skirt fluttering against my thighs, I knew the war was over. I wasn't a straight boy with a hobby. I was a man's sissy, and for the first time in my life, I was exactly where I belonged.
The heavy silence of the bedroom was punctuated only by the soft rustle of sheets as Brad tucked me in, his movements efficient and devoid of the warmth I craved. He leaned down, his voice a low, steady command that brooked no argument.
"You are not permitted to pleasure yourself tonight, Sara. You stay exactly as I left you until morning."
"Where...where are you going?" I asked.
"To get ready for bed, I'll be back." He didn't wait for a reply, leaving me alone with the thrumming ache of my own body and the weight of his authority. When he came back, he held me, finally. But he didn't touch me. That wasn't part of me, not with him.
When my eyes fluttered open the next morning, the space beside me was cold. The sunlight streaming through the blinds felt too bright, too clinical. Brad was gone, no lingering scent of coffee, no parting words.
On the pillow where his head had rested lay a single, crisp note: "Wear the charm and wait for my call."
The "charm", the heavy, symbolic weight of the collar, felt like a lead weight around my neck as she sat up. I felt a strange, dizzying cocktail of abandonment and total possession.
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