Shy Guys Make Good Boys Pt. 01

I couldn't keep from exhaling in need, when she had my head tilted back and was standing behind me to fit the collar to me, so that I was looking up at her. Her eyes glowed with pleasure and she fixed the collar nice and tight, making it clear that it wasn't going anywhere until she was done with her boy toy. Just talking.

Fuck me, I kind of wanted every conversation to come like this. "Talk with me, baby. How does it feel?"

But there was a smile in her voice after that moan, when she knew the answer perfectly well. "Good." My voice was hoarse. "It feels... it feels so good."

She laughed above me. "You did mention a favorite fetish of mine. Leash training, when... well." She crooked a graceful finger through my collar's ring and I lifted in the chair, arching against the cuffs that held me her prisoner and the end result was a desperate breath with the fire it gave me.

"Yes, Mistress."

I never wanted to stop saying those words.

"Of course, there are other places to put... leashes." Her hand was the gentlest, most teasing press when she trailed it down my chest, her other hand cupped beneath my chin, right over the collar. My pulse thundered like a drum in my ears, so loud, after we'd talked about my being open to sexual touch for the first time we tried this, and then she kept stroking that hand down, down...

I jolted when she reached my cock, when her touch was expert, just enough to be a tease, and holy hell, was that animal growl from me? For a moment, I was terrified I was going to embarrass myself right in her hand, when I'd never been so fucking hard in my life. My vision went hazy with that touch of hers.

But then she just delicately withdrew, laughing low in my ear. "Like connecting one to the chastity cage I have for your cock, once we get to know each other a little better."

What else did you answer to that? "Yes, Mistress."

Her laughter turned slightly louder. "Good boy toy. But you had other fantasies you wanted to mention, too."

My insecurity was no longer louder than the roar of intensifying lust. It'd been a joke to think I'd keep the rest of those fantasies from her. "Y-yes, Mistress."

She stroked my hair again and I couldn't keep from leaning back to that touch, from enjoying it when it was so approving and soft. Her gloved hands felt sleek and I closed my eyes briefly before I met her gaze, praying to a goddess that she would be nice to me.

I didn't think I could say either of those safewords to stop her if she wasn't. It made me ache, how wonderful it felt to have her look down at me with that kind of approval and security. "Still so nervous, aren't you? Let's see if we can help you with that. I'm not usually too partial to blinding my male submissives when most of them are just so... visual. But let's turn out the lights for you for a moment."

"N-no, please?"

Sonya turned and her eyes were cutting. It was the most subtle change after I couldn't help but beg with the thought of being denied the sight of her when she was exquisite to look at. What was horrible about it was how she didn't glare. She didn't so much as make any sign of violence with her displeasure. That gaze was merely glacial and I shuddered when she lifted the riding crop along with the blindfold. "You will learn that is a dangerous word for you. It would be easier if you stopped using it, love."

I hated the thought of displeasing her, but I didn't realize how awful it was until right then. She didn't have to punish me to make the thought sink in. No, it was enough that she was the first person who made me feel not so alone, the first person to somehow get me to confess to her. "Yes, Mistress." I lifted my head when she raised the blindfold and it helped that the last thing I saw was her smile of approval again. "I'm sorry." It was fearful, pathetic actually.

Her hand was gentle when she fixed the blindfold and she stroked my hair again delicately. It was an action that made me think I had an unrealized hair petting fetish. "Poor little boy toy. How long have you had your fantasies, Ryan?"

The crop scattered my thoughts when her voice came from in front of me and I felt the small slapper of leather trailed up my cheek and down my jaw. I shifted, shuddering again in the chair, and the shock of pleasure I had from the sensation was enough to make me answer honestly. "Since seeing Olivia Newton-John step on a cigarette and place a red high heel up to John Travolta's chest."

The crop paused its stroking and she laughed above me, a full sound of her pleasure that made me smile, then breathlessly laugh along with her, when it gave me so much relief to have regained her happiness. "I suppose that is a good place to start, at that. A while, then." Now that I was 28? Yeah, it'd been a while. "All that time and no one to train such a good boy? That's just wrong, really." God, she was going to be the death of me. My lips parted when she tapped the crop to them and she took advantage of that fact, slipping the leather between them. "Suck." I moaned when I did it, then moaned louder when she cupped my jaw and thrust the crop harder... in a fucking motion. She leaned closer to me, kissing my cheek, and her breath was warm when she finished her words. "And good boys learn how to use their tongues and mouths just so well with training. I think you'll find a cock cage makes you learn amazingly quickly how Mistress likes it most."

I whined with the removal of the crop, only to gasp eagerly when she lifted my chin with it instead, pacing around to stand behind me so that my head met her navel, using the handle of the crop and holding it at either end. Her motions had turned harsher and it made me shudder with the scent of her behind me, when I could smell her arousal, that same hot, sultry scent from the first night I'd met her. I thought I'd kill for more of that scent. As it was, I merely lifted, straining in my cuffs, enjoying the choking crop when she held me back.

It made me outright growl into her mouth when she pressed her lips to mine. I tried to touch her... and then hissed when I couldn't, when she held me at mercy and it was only reiterated all the more for me. Her kiss wasn't a kind one, either. She didn't let me doubt for a moment who was in control of who, not when she thrust her tongue like that between my lips, as assertive as I wasn't.

"That's it." Oh, and her voice when she started to be more exacting and more rough? I pant a little, starved for more of her. The goddess. "Let go for me and let me have you." When she reached down my jeans again to rub my cock, I gasped with the slack on the crop at my throat, then pant with the gentle pressure she used to stroke me. "That's what submission involves, pretty boy. All you need to worry about right now, for instance, is whether or not I'm going to make you cum in your jeans so I can enjoy the sight of the mess there for the rest of the night."

I couldn't keep from a thrash of ecstasy. She was relentless... until she knew it seemed close to too much and withdrew for a moment again, her laughter in my ear. "Maybe if you're a really good boy for me and answer my questions, I'll show you what the cock cage feels like while we eat, so you can get used to how it cradles you under your clothes. I think you'll enjoy it. Well, sometimes, at any rate."

"Mistress..." The collar around my throat already felt cradling, as she put it, so much so that I craved to keep it on for her. "Mistress, please."

"I'll give you another chance, since you beg so prettily. Tell me one more fantasy, Ryan? We'll work to the ones that make you so uncomfortable together, boy toy." I bit my lip, then shifted in torment when she nipped at my ear, my goddess interrogator when I hadn't confessed my pen name or any of these desires to anyone else. "Telling fantasies to someone like me is a good way to have them come true, love."

That's what I was afraid of. I struggled my cuffs a little when she stroked around my thighs and couldn't keep from saying it when I was that worked up. It was painful being that way, on her edge. "Cum swallowing."

Her hand paused where she had it so gentle in my hair again and I bowed my head, shuddering, shaking. "I take it you don't mean mine, baby."

"No." The word was a moan of dread when she held me under so much control that I would say the fucking words out loud.

"Good boy."

"Oh, Jesus, please!" I was shaking again, with her touch. It took everything I had to hold back orgasm when she went back to stroking me over my jeans and I really didn't want her to go through with that threat of making me finish so it showed through the fabric. But I was so goddamn close to breaking. All it would take was the wrong motion from her and my control would shred apart so that I spritzed hot cum in humiliating bursts.

Sonya was laughing again, evidently in high spirits from my display. "God, I love a man who will beg, baby." Her whispered, feral words were hot sin at my ear and I shuddered. "I'm proud of you and good boys get rewards, after all."

She pulled away and tugged the blindfold off, so that my eyes zeroed in on her as soon as my sight was given back to me. She looked more beautiful than ever and I swallowed when the visual gave me her... without that dress she'd been wearing. She'd tugged it off and now she wore only tight, skimpy lingerie with her gloves and boots. Her eyes had a fire in them, instead of the eternal calm from before, and I lifted to her with the thought that Mistress was beautiful in her desire, more gorgeous than ever. Her skin had a flush with the heat of her and when she stepped closer to me, it made me shudder with the way the heels made her gait seem predatory, dangerous.

"I want to see you masturbate for me, instead." That made me blush even while it made me throb. She was quick about undoing my cuffs and she gestured to the floor in front of her. "Here. Kneel."

I couldn't think straight enough for any part of my mind to come up with a protest anymore. I merely knelt, obediently, looking up at her in supplication. "Please, Mistress."

The arousal was white hot, almost painful, and a lot of it had to do with the shock. I had known it turned me on, sure, but this? This was wild. I groaned when she stepped close to me, so close, when she grasped me by my hair and tugged my face to her pussy, where there was only a thong between my face and the taste of that perfect fucking scent. "Unzip your jeans and stroke your cock, Ryan."

My nose skimmed her pussy over the thinnest fabric. My blood thundered in my ears. I closed my eyes and inhaled more, dying a little when I obeyed her, spreading my knees and freeing myself. The flush of my neck was as hot as the lust made me, but I couldn't find it in me to care.

She tilted my face a little further. "Suck." It was the softest command and by that time, it was barely audible over that thunder in my ears. I sucked, whimpering happily when I did, and Sonya tapped my back with the crop so that I shuddered. "Ah, ah. Lighter, baby. You'll find Mistress enjoys being teased. I'll want both of us to last." That made me slow my own strokes on my cock when I wasn't sure how much longer I could hold off and it was immediately evident that Mistress noticed with how she chuckled above me. "Charming little boy toy, aren't you? That's it. Christ, you're good with your tongue." Hot pleasure of a different kind flooded me and I gently curled my free arm up her thigh, still stroking myself in even motions, tormenting myself for her pleasure. Mistress' hand turned gentle in my hair and she lightly eased my face in a back and forth motion so that my tongue teased and lapped around her clit. "I'll teach you to beg to taste me, baby." Her voice was a low threat over me and I shuddered, the world close to blasting apart from under me. "I'll break you until you crave pussy over orgasms and I'll teach you how to use that tongue of yours while you spend hours eating me like a good little boy toy. They'll be your favorite nights with me."

Hours. I had to stop stroking myself entirely for a moment with the thought of being so filled with this heavenly scent. She purred over me when I swirled my tongue, slowly to better tease her. I stroked my free hand down the back of her knees, thrilling to how soft her skin was in contrast to the shining leather boots she wore. "Jesus, that's good..." Every sound of her delight was my drug in this strangest mental world where the words "good boy" were fucking bliss. "A little harder. Don't cum yet." The crop stroked my cheek again and I moaned against the fabric over her clit, laving it. She was drenched behind her thong, so much so that my tongue trailed the outline of her pussy's lips easily and I moaned louder. "Such an eager boy. God, it's going to be so good training you."

I wanted that more than life. I wanted her to pet me all over and make me bow like this to her heart's content. I wanted to buy her more and more gifts so that I could see her gorgeous smile.

"Harder." Thank God. I thought it might actually kill me, the effort to hold off any longer, and I had the prayer that her orgasm might come with permission for my own. I laved her greedily and she chuckled, the sound a little breathless. "Naughty boy. After I train you a little better, your pleasure won't be tied into these things at all." I moaned at that when I realized she knew why I was so eager. God, she'd gotten me to tell her things I'd never thought to tell anyone... and I didn't care. I whimpered with the thought of the cock cage waiting for me. "Harder." Please, fuck, yes. I could barely stroke myself at all anymore.

I gasped against her when she abruptly grabbed my hair in both hands and forced me to her, riding my face viciously, taking her pleasure from me as she wanted it, and her voice was a low snap when she said, "Cum for me." I growled with the force of it, with the way it made me breathe in frantic pulls of air that were filled with the scent of her. It was fucking earth shattering, the kind of orgasm that made my legs shake.

But it was the end of it that did me in. She finally allowed me to pull away from her and I bowed my head, staring down at the drops of cum on the floor, dazed. Sonya delicately went back to stroking my hair, while I marveled at this sensation, this feeling. I was...

Numb. Calm. Validated.

I had gotten her off and there was zero doubt that it was the way she had wanted to get off when she had been so secure in her touch, in demanding I do what she liked. It was this sensation of having done something really fucking well and knowing, for sure, that I had done it well. But it was more than that, too. I nuzzled her palm when she caressed my cheek, closing my eyes in a kind of reverence. I had an image of a wolf fighting against a bigger wolf so hard and for a long time until it finally lost and went still, until it turned almost serene and waited.

Submitting. Surrendering.

So this is what it feels like. It was peaceful, in the most exciting way as odd as it sounds, like being told to hold her hand and not having to question it.

"Ryan." Her voice was soft above me and I opened my eyes, shuddering at the memory of the shape of her pussy against my mouth. She had felt perfect. I didn't know it then, but she would keep all those threats she'd made and a lot of others besides, when she made sure her pussy was the altar I'd learn to kneel and worship at. And her boots? I couldn't raise my eyes from the sight of them, from the cum at her feet. "Have you ever tasted yourself before?"

I moaned, then whispered, "No, Mistress."

"Good boy for being honest." It felt cold when she walked away, when she went to a closet and got a box along with a wash cloth, wetting the latter. I jumped when she knelt to me, undoing my jeans the rest of the way and gently bathing my cock. "And you obeyed me when I said to intimately shave. Easy." She said the last when I shuddered, when I had the thought of what came next. "I'm not going to make you lick your mess up this time, baby. But, well." I leaned back obediently, watching her when she pressed me. She was delicate when she met my gaze, cleaning up my mess with a wicked glance that made me blush before she opened the box she had brought to me, letting me see the cock cage she had before she deftly fit it to me.

I exhaled with the sight of it, with the way the metal bars seemed so deceptively innocuous, feeling far away from my body in some way. It felt heavier than I would have expected, somehow, and my Mistress was not done with her threats. "You might be eating my pussy again later with how horny the thought made me, though, just to be clear on my intentions." With the cock cage? I whimpered, thinking of that scent of hers and how I thought it might kill me if she had me do that. "We'll ease into things together and we'll talk with each other. For right now, for instance, I'm holding onto the keys to your pretty new cage while we have our date. Depending on how it goes, maybe I'll let you take my gifts home with you, if I'm feeling like a very kind Mistress. Maybe I'll even allow you your collar to play with."

It was strange. Everything felt surreal and I was still so far gone in this mental place that fascinated me. It was so dark in one way, in how it was almost suffocating, drowning. But then there was another side, one that made me feel like I was drifting or flying, one that intensified in pleasure when I stared at the cock cage with the knowledge that she would control the pleasure I felt. She could make this into that darkness or she could make me fly at a whim and it sent shockwaves of thrill and heat through me. I shifted when Mistress helped me fix my jeans again. The sensation of her cock cage struck me as well, when it wasn't painful or anything like that. A little uncomfortable, maybe.

It felt like that word she'd already used, the one that was perfect for the collar, like being cradled, actually. My balls were cupped with a ring and the end of my cock was nice and enclosed in the metal plating of the cage. The rest of it was smaller bars, however, and she'd sized me perfectly after our conversations.

I stared down to where it was hidden, obediently staying still when my Mistress calmly said over me, "Stay kneeling. I'm going to change into something more fitting of a date, love."

"Yes, Mistress." The words felt right on the most animal level. I stayed kneeling like a good boy, staring down at my hands in my lap.

What was the worst that could happen? It turned out I hadn't anticipated the reality of the worst that could happen. I'd written it out in a dozen different ways, but the reality of it was something that made me swallow. Because the worst was that I would find the fulfillment of my nature in bowing... and would never find my way back from it again, that I would find myself thrall to a Mistress I had been intending to date.

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Sonya

It had been a toss up, honestly, deciding whether to play with him first or have a date with him first. On the one hand, he was an anxious type of person and I thought it might torment him to have a date while knowing, especially after all of my careful messaging conversations with him, that sex and submission waited afterwards. Even if I would have only lightly played if that were the case, would have kept it to restraints and a collar, he wouldn't have known what to expect.

On the other hand, if I did it before the date, I had to contend with what ended up happening that night. Subspace.

I anticipated it. The problem was - as another moment in a series of them to thwart every last one of my intentions - that I didn't anticipate nearly the strength in which it affected my new little boy toy.

Ryan was still and waiting where I had commanded him, staring down at his lap. His hands rested on his knees and he sat up straight, with a naturally beautiful form. It impressed me, actually, with how he clearly wasn't fully comfortable with some of this. And yet... he was brave for me. And he was gorgeous. Of course, I wouldn't tell him that last thought. No, I would call him a good boy and scratch his hair until he nuzzled me in that way he had done.