Shy Guys Make Good Boys Pt. 01

"Ryan." I used the voice I considered to be my more nurturing voice. For him and his aftercare, it struck me as the best with the mood he seemed to have for the moment. At first sight, I actually had concerns about his subdrop.

But then he looked up and I reconsidered, smiling thoughtfully. How serene he looked. How peaceful and calm. He made a low sound when his eyes fell on me and I reevaluated my ideas, pacing to him so I could touch his hair again. Touch, it seemed, was incredibly effective for my good boy. He lifted his chin as soon as I did, raising for more of my stroking. "And what does that look mean, good boy? Be honest with Mistress."

My voice was teasing and it succeeded in pulling a smile from him, but then his eyes turned more serious and timid. "I was thinking that you look wonderful, Mistress." He paused, blushing, and I realized that my new dating interest was going to give me problems. He was far too cute for his own good and, as Courtney would say, it didn't help him out with me.

The truth? I enjoyed the feeling of a Dominatrix with her submissive for more reasons than just the sexual. I could keep the control in that relationship when I disliked too much emotion in myself. The hard truth was that the more endeared I felt towards him, the tighter I would hold his submissive leash. It wasn't a cruelty thing, nothing like that.

It was my own shortcoming, mostly, but also partially due to how aroused it made me to see a man on his knees, degrading himself in emasculating ways for my pleasure.

Naughty boy. Do you want to end up in my chains? You might want to stop flirting so hard with me if you don't. Otherwise I would work towards seeing those gorgeous wide eyes in that adorable baby face every day, waiting for my next command, towards hearing that soft voice beg me permission to taste his Mistress.

"I was thinking that I adored your dress and boots, but that your jeans fit you well."

I stared down at my blue jeans, smiling. "You're too kind, baby." And for a moment, I hesitated, but then... I don't know what it was. I think it was how completely he submitted. The atmosphere was intense, so intense that even I, for all my fear of being lost in emotion and how it would make me naturally weaker than a Dom, had trouble trying to work up the willpower to leave the atmosphere with him. When he remained kneeling in such ready subservience and with the knowledge of the cock cage he wore holding him chaste and under my key, I...

I didn't want to leave that atmosphere for a date. I wanted more emphasis on the domination and submission aspect of our relationship. Right out of the gate. It was unfair to him and I both and I quickly made mental contingency plans to place us both in a date scenario that wouldn't be so fraught with this.

He shuddered. "I want to tell you more. But I'm worried it will sound incredibly desperate right now."

I paused and tightened my hand in his hair, feeling energized with the low, sexual growl that escaped him to how rough the motion was. "Naughty boy. Let's get something clear. Tell me to your heart's content and if it's authentic, I'll enjoy it, little boy toy, just like I'll enjoy your begging when you think it's desperate."

He blinked and his eyes were so very glazed in such a delightful way. You call him naughty. You're supposed to be behaving, Mistress Sonya. "It's more than that," he finally breathed after my prompting. "Mistress, your hair looked sexy and strict with your leather, but it looks just as wonderful with the jeans and shirt you've chosen. I admire that."

Wicked little boy. That balking at drinking your cum is the first thing we'll get rid of. I'll train you to enjoy the taste until you're my slutty little toy for it. Jesus, I had never felt so fucking... dangerous before. It was this sense of carnal possession that didn't bid well for him.

See, I had always been the caring Domme, the one who dispensed with my fetishes when they were incredibly demanding. I had always been the loving Sonya, the careful one. But with him? I'm not sure I'm explaining well, but he made me want to indulge in all those demands. He even brought a delicate sense of sadism and dark fire in my blood. With how he was driving me, he would be a whimpering little toy, oh yes, and he would be so well trained that he wouldn't so much as beg when I commanded him to make me orgasm while he wore his cock cage, while he remained chaste when I owned his keys.

Christ, all he did was give you a compliment. "I'm sorry, baby. You caught me a bit off guard." He grinned in mischief and I felt myself fall to that dark temptation a little more. "Don't give me that playful, mischievous look," I said, shaking his hair, but of course that only made him giggle. "Especially not after a compliment so good as that. It's a dangerous thing to get to a Dominatrix's heart these ways." I didn't want to say the words. I wanted to let him keep taunting me until I broke, until I made him into a little toy slut, until he begged me every morning to kneel and taste me, until he thought of it as worshipping his goddess.

Mmm. Oh, I liked these thoughts far too much.

"Mistress... At the moment, I think your form of dangerous sounds amazing."

I burst into laughter. "Boy toy, you're misbehaving. I'm supposed to be giving you after care and bringing us both down to earth. Maybe a session of having your cock and balls flogged would make you reconsider being a little submissive tease to Mistress."

Because how dare he be such a tease with that flirting mischief.

He paused and gave me a sly smile that only made things all the worse. "Maybe you should try, Mistress."

I growled down at him. "Wicked fucking thing. No. Bad boy. You want that? You ask for it. Let's get that clear right now. I do not condone male or female brats and it's probably the one fucking thing I'm not sexist about. My plan for tonight is to have a date."

His eyes went wide and it was an indicator to how deep in submission he was, at least for me. I think it struck me that maybe flirting would have been a way for him to find his way back from that magical, oftentimes intense, headspace. Would have been. As it was? He stared up at me with that stricken gaze and then bowed his head and caressed my ankle. "Mistress, I'm sorry. Please, I didn't mean to harm your date." He glanced up at me in such a fearful manner that it made me pause in a brief arousal, when it abruptly fascinated me how small I was physically and how submissive he was emotionally.

You're feeling too much. I turned my thoughts to something more logically inclined again, considering how to go about our date, for instance. I still had to finish making dinner, which would only take twenty minutes or so when I had prepped everything, but something felt wrong about sitting together at my table, when we both seemed trapped in an atmosphere. I really wanted to make him bow at my feet and eat from a dog bowl, but my conscience wouldn't just let me do that, either. It made me glance at my coffee table thoughtfully, made me think of how to go about having him near while I finished cooking.

He was the one who solidified an idea I had. His eyes followed mine to the coffee table, where my chess board was, and he tentatively asked, "Do you play?"

I smiled down at him. "Yes, as it happens. Would you like to play in here while we eat?"

His eyes lit up in a way that made me smile, with how clearly he would definitely like that. It gave me my answers. "I'll take that as a rather definitive yes. Stand up and come on, love. I need to finish the food and you can help me."

There was a thrilling sensation to seeing him stand up, while still so clearly in his submissive headspace, when it forced him to look down at me, even with my boots. There was something so subtle about a guy in submission, at least to me and in certain ways. Like right then. Even if he was bigger than me and he was obviously stronger than me, his eyes went to my feet and he had this cast in his features, of waiting respect. He stroked my hand when I placed it in his, leading him.

Pulling a submissive from their headspace was always something that struck me as such a delicate thing. I had experienced some deeper subspace moments before and the memories stayed with me, so that I always felt like I could never be careful enough. Ryan was a new level of it, as it would turn out. He was so atmospherically trapped that I gave him careful commands in what to do to help me and his own ambience infected me so well that it felt natural to give those kinds of commands, like a dual natured conditioning.

But it was when we sat down at the chess board that I had hopes he might be able to pull out of his subspace. Where it had seemed strange to sit together, it felt rather enjoyable to curl up on the floor at the coffee table together. With chess in the mix, I hoped the logic of the gameplay would give him a different form of thinking.

Remember how I said my relationship with him was nothing but a series of fantastic failures? Just keep that in mind.

The interesting thing about it, though, made itself quickly apparent. I had retreated in forms of logic to get away from my own emotions when I thought I had too many. Ryan... Ryan didn't let me stay behind my armor. He took the most logical game in the world and he lulled me with it.

At first, it was quiet enough. I went with a queen's side opening, freed my bishop, moved my knight, positioned my queen. For a moment, we traded turns quietly.

And then I saw a few openings to more freedom. I went with a queenside castling move and Ryan sat up straight, his eyes going wide so that I couldn't help but grin in delight. See, within a few moves, it was apparent that Ryan enjoyed chess. A smile broke across his face, slowly, and I couldn't help but feel thrills. "It's always a joy getting to see someone's face when they realize they're playing someone who loves this game as much as they do," I said.

He broke into happy laughter while I watched my armor start to fall apart. Bad boy. Bad Sonya. Bad both of us.

Damn that baby face. He looked far too delightful with my collar on his throat, especially when he laughed happily after he lost. Okay, logic wasn't working.

Maybe space would give us both a little more perspective.

Want to take a guess at how that turned out when I'd charmed him with a chess game? Go on. Say the quote about insanity and people who try the same thing over again. I'm daring you.

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I made us both take a week, but I gave him a way to open conversation with me as well, with the cock cage and his collar. Before he left me, I gave him the cage and the key to it and told him there was one rule. He could wear it when he liked, however long he liked, but he had to tell me when he decided to take it on or off.

It made me smile, the look of fear he briefly got. That's it, you're going to let me know exactly how much you love or hate it. Which was true, but there was a little more to it, too. He was quiet, reserved. During our chess game, for instance, he'd had an air of shy serenity.

I hoped that giving him a command for when to message would open the doorway for his comfort. This logic, as it turned out, worked a little too goddamn well.

He didn't message me as early as I thought he would after he left me. It was actually sometime in the dead of night that my phone went off and I woke up grinning with the realization that the poor guy tried sleeping with it. And then it made me aroused with the thought of abrupt pain waking him from his sleep, of him giving one of those whimpers that made my blood race in that wicked way. It made me wish I'd been there with him, keeping the keys instead, so that I could stroke his hair back and coo in his ear to let the pain wash over him and do its job until he was a good boy again. I'd kiss his neck in a tease to make it worse and tell him there was nothing he could do about it when I had the key... Jesus, the fantasy had been intense enough that I'd bitten my sheet, stroking my clit in gentle circles so that it amped me up and up, slowly, until my world turned to bliss with the memory of his expression when I pulled his head back with the crop.

The weekend was a series of sporadic messages, but it was the weekdays that got... interesting. He messaged me Monday morning, you see, and I was suddenly energized while I was getting ready to work. Bad boy, you're being wicked. I had to grin with the thoughts of him wearing it to work, trying these things out, of how I now knew some of the places where he liked to write his erotica, when he liked to feel naughty in his own quiet way. I teased him, taunting that it was his little secret. Of course, there'd been other messages I'd sent him. Wear tight boxers, though.

I started to smile every time I looked at the phone, thinking that he was both messaging me a fair bit... but not quite the times I was expecting or nearly as much as I would have expected.

Even after what we'd talked about and even after the nature our date had taken, though, the messages were timid, ones that always started with "Mistress?" If I'd wanted to go back to some kind of vanilla dating, I should have asked him for conversations where he called me by my name. I've always looked back and thought that there was no one to blame but me. The truth was that it wasn't just the sex, once again.

It warmed my heart, especially when he apologized for seeming too needy every now and again.

Ryan, love, I'm coming dangerously close to keeping you.

Because he was apologizing, respectfully, for the very qualities I adored in him. He would ask my permission with the cock cage, even if I'd already given it. Most of the times he messaged me were close together, where he'd tell me he was taking it off and then, quite quickly, tell me he put it back on, though, something that made me grin every time. And, like most introverts, he was indeed more open in text than in speaking.

I thought about you, Mistress.

That one always made me smile. Oh, yeah? And what made you think of me?

There were a number of things. I was reading a story :P, he would say, or, There was this artwork on one of the new Adventures in the Forgotten Realms cards. And he would send me a picture of the artwork or send me a link to the erotica.

I took the openings to flirt, unable to quite resist when it felt so good and everything he sent was so very flattering. For instance, my answer with the erotica? Be careful, little boy toy, flirting so hard and complimenting a Dominatrix so well. Although, I must clarify that if you ever call me 'Ma'am,' I'll beat you and it won't be in the good way.

I just laughed out loud at work, Mistress.

That made me grin in my own work office and I had to focus on getting back to my job. The only thing that was keeping me on my tasks, with thoughts of him in the background, was the fact that I was an R&D manager and if I didn't, a lot of very shy scientists would be without an adequate safeguard between them and other departments.

It was a week later before I finally caved. I thought it was enough time for him to have some space, for him to consider how he felt about the submission aspect of things. I spoke with him about that through that week as well, thinking I could guess a few answers. For instance, I didn't think I had to wonder if he enjoyed the sexual aspect of submission. I did clarify that we would talk about other options if it wasn't to his liking, however.

These were light conversations, though. The real one came when I finally did cave and called him.

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First, I messaged him and asked him what he was doing. When he said he was at home, I called.

"Mistress?"

His voice was soft, a little shocked, and with a kind of shy fear to it. It made me smile. "Good evening, love. Have a good day?"

He seemed to become a little more confident with the question, as if he was adjusting to the idea that I was calling him instead of messaging him. "Yes, thank you. Did you?"

It had been terrible, actually. My day had started with my opening a supervisor's door after reading an email and the conversation had started with my standing in front of his desk, boots shoulder width apart, and saying, "Hi, yeah, what the actual fuck is this?" I didn't mind when emails and notices affected me, but I preferred to not overwork my engineers. It didn't help that the supervisor in question was a weasel faced motherfucker that bullied the shy, quiet types that worked for me, but couldn't look in my fucking eyes like a man. I'd been, ah, a bit fiery.

And then I'd felt bad about it, stopping by a liquor store and staring at shelves, wondering which bottle said, I'm sorry I acted like a cunt, even if you're a twat. I could have been classier about it, though.

Ugh. I kept thinking that one day I would get used to being an outspoken female. But I couldn't get the voice of my conservative family out of my head and it always gave me problems at times. Sonya, please. Our family doesn't do confrontation. Don't draw the attention. Keep your head down, Sonya, and stay proper. Any girl with too many opinions can tell you that we're generally about as insecure as everyone else, even if we can hide it better.

That day had been one of those rougher days. But I didn't find it in me to confess that to him. Part of it was because I didn't share those things with people, when I'd learned that I got enough criticism from people like my family and I would not give them the satisfaction of knowing that they affected my days or moods as well. I would not make sound or complaint about what made my days bad, and I especially could not do so to a submissive man who was trusting me to safely show him kinks and to care for his psyche and wellbeing when he likely had insecurities of his own.

When he left me, I intended for him to be in better shape and with more knowledge than when he had met me. It was fundamentally important to me and burdening him with my feelings or problems felt like something that would be an obstacle to that.

But the other, scarier reason? The sound of his shy, sweet voice had already succeeded in making me forget all of the things that had made me feel so bad. I shoved the emotions he gave me into a mental box labeled, Later. "It was productive, little boy toy, thank you for asking."

He paused and then softly, in a breathy voice, with just the right amount of fear, answered, "I love it when you call me that."

I paused, smiling, thinking he must be in a frisky mood to confess that. "I'm glad to hear it when it will be fitting if you decide to keep going down this relationship path with me. That's what I wanted to talk with you about. But first, have you been a good boy? Be honest, Ryan. Did you message me every time?"

Now he was definitely antsy when he answered. It was delicious, with just a thrilling amount of fear to amp the arousal for both of us. "Yes, Mistress."

I blinked. His voice was so fearful and respectful that... I believed him. Without doubt or seeing his eyes, I believed him. Before that answer, I had thought, for sure, that he had forgotten to press send, maybe, or been a little too shy and embarrassed about his desire a moment or two. I sat straight in my bed, having dressed in a tiny pair of pink jogging shorts, the kind I would only wear while alone, along with a tighter tank top. "Ryan, you didn't message me all that often."

"Forgive me, Mistress. I- I was worried about bothering you if I wasn't..." His voice shook. "If I wasn't taking the cage off or putting it on."

"That wasn't my point. For future reference, however, I like hearing from you and getting to know you. If you're bothering me, I will tell you. We'll get to that in a moment, though, along with a few other things. For now, tell me this. What did you take your cock cage off for?"