Wolf in Sheep’s Clothing

It was another addicting moment where I realized I wanted Lily to show me everything she knew because she jolted and made this low sound of shocked ecstasy, a hoarse sound like she was trying to not scream with her pleasure and nearly failed. Her pussy milked my fingers, pulsing in erratic spasms that made me burn. I think she'd intended to keep making me calm with her flirting, but she made me calm in a different way.

Because she stared at me while she shuddered and fell still, watched me with this dazed expression of helplessness that made me think of all the sick advantage I could take of her. Instead, I crawled over her and knelt over her tits, undoing my jeans enough to free myself, stroking my cock while she watched. I flicked a clamp with my free hand to see it jump, to watch her twitch from it. She flinched and I grinned, enjoying the thought of her being a used up slut toy, thinking condescending words that I didn't say out loud, things like, "It's almost over."

She whimpered when I released one clamp and then another, while I thought about how cute she was when she was scared and when she hurt, staring down into her wide eyes... I grunted with the force of the orgasm when it was finally too much. Cum spritzed on her tits and she inhaled a shocked breath.

Ever finish and realize quite what you just got off on? I stared down at her, both loving the sight of cum on her and instantly worried. "Lily? Are you-?"

She jolted and didn't let me finish because she grabbed my face and pressed her lips to mine with these little whimpers of joy that made me feel shy, made me blush. I clasped her hair and nuzzled her, then licked her lips when she kept kissing, frantic kisses. I wasn't sure if this was Lily's version of aftercare.

But I wasn't fucking complaining either way.

————

Lily

Oh, like he said anything about my teaching him. At that point, we were just feeding each other's energy! He was shy, not totally innocent, if we're all being honest with ourselves.

It started to sink in about that time that I was pretty sure I'd found a masochist's wet dream. I noticed that his excitement turned more and more the hornier he got and his eyes, so calm and mild at every other time, started to spark with that eagerness. You know how hunter animals will get more and more frenzied until they taste the blood on their tongue and feel the satisfaction of biting? That's what he was starting to seem like the more I talked with him and got him to play. After he finally managed to pull away from my needy kisses and leave, teasing me again, I had fallen against my wall and massaged myself between my legs, whimpering while I considered the thought of him using a crop on my tits and clit, and pictured how his eyes would get more and more excited at the sight of the reactions until he broke and switched to the cane and made me really scream. I imagined him having to gag me with that gaze that he got with his amusement because he'd gotten it off the clamps, had breathlessly laughed at how intense those particular clamps made me feel. And that was another thing. I had played with a lot of different people, but there was one thing that made the best sadists, in my experience.

It was how well they got engaged with reaction, how they laughed so softly at sounds of pain and torment when it truly amused them. You see, the best sadists took those delights because they felt like intimacy to their love language and sometimes they had these shocked little chuckles with how much they liked that form of intimacy.

Alex had made one of those little laughs and stared at me as if shocked to find himself so connected with another person. His gray eyes had been alive and terrifying because he'd watched everything as if he couldn't get enough of the sight. He didn't know domination and, by his own admission, had never even played it before. So I for damn sure didn't think he knew the next part, which was the fact that his shy nature and the way he so carefully watched everything to gauge reaction and pull more reaction might have made him the perfect sadist.

I orgasmed to the memory of him talking to his boss, to the way he so softly spoke with such gratitude for being guided and told what to do, covering my mouth and laughing breathlessly when I came down. I lay in my floor and licked the clamps, thinking of more ways to teach him and to encourage him. What was more was the thought process made me realize that he had just left, but I missed him. I had to admit to myself that I was thinking of these things to try to forget the growing obsession because if I spent too much time thinking of how obsessed I was, then I might get concerned that I was acting a little more than infatuated with him.

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Okay, Lily's third rule on training your wolf to eat you! Heheheh. Get it? Because... Anyway! Here's the thing about being the one with the knowledge of what to do. That makes you the teacher. Now, teacher roles are generally the nurturing roles, the dominating or the caretaker role. That gives us a tricky path to navigate when we want to train someone to top from the position of being a bottom. So, how do you do it, besides with encouragement? For a start, you never act like a dominating teacher. You go for the guiding feel instead.

For the next bit, you use something to balance out the teaching. You give them something to teach you, so you have a trade off scenario instead. That's how I started spending my nights learning JavaScript. Also because it was fun, surprisingly so. Alex had said you could learn most all of it on a phone app, had shown me which one, and my life had started taking a few weird turns. I was dating when I rarely attempted to date anymore. I wasn't going to play with my sadist friends at my favorite fetish club. I was reading through a Dungeon Master guide book and playing with character sheet ideas.

And I was curling up in my room, instead of going out, and playing with JavaScript tutorials. What was truly terrifying about the fact was how good I turned out to be at it. It was design work, which was what I already was so good at. I would play with it and then message Alex excitedly. Want to see what I did?!

Of course.

I sent him back a notepad file for him to run it and he always sent back approval, so that I felt all warm and glowing inside. It gave him something to teach me and I loved it, loved the excitement of learning something new and fun.

Of course there are most definitely other ways to balance out that feeling of power imbalance. Besides curling up at his knees while I talked with him and besides the careful way of never seeming in control and besides learning something that he was interested in. We had a week or so where we took things slow, where I looked up at him and talked while he stroked my hair. Some nights he'd play with programming languages with me, but... Okay, the real reason was we got distracted for a couple of weeks.

With cuddling. He was the best fucking cuddler ever. I was kissing him to say hello one night and we ended up on my couch where he stroked my hair and held me close and then we lay down and I nestled into his arms. And I loved it there. I never wanted to leave. My version of sex didn't allow me a lot of cuddle time. Oh, it allowed me aftercare and things like that! Don't get me wrong, I had Doms and other playmates hold me, but we all knew we were involved to scratch an itch, you know? I really liked Alex and he seemed to like me, so I snuggled into his chest that night and never wanted to leave. For a long while, I didn't even say anything with the shock of pleasure at being held like that. When I did talk, I rolled over first and held his hand over my waist and softly asked him about books.

I loved cuddling with him, loved it. He was warm and his arm felt safe and gentle around my waist and he was easy to talk to. I got distracted from even sex. Okay, that's a total lie. I would roll over and start kissing him again, fixing his hands around my throat and in my hair so that he smiled against my lips. I whimpered and he'd choke me just a little so that I would nuzzle closer happily. "Yes, please."

He laughed against me and did it again so that I turned more and more giddy and aroused, until he finally broke and said, "You're killing me, Lily." And that meant he was too horny and I had to do something to help him with that. So I did. I jerked him off so that he came across my face and then I could stare up at him like a slutty, marked dog. I had cum on my tits the most though because he really seemed to like my tits. He always stroked his thumbs over the nipples and rubbed his cum in a mess while I lay and whimpered in soft arousal.

But the day I decided he might like a little more control started because I didn't have any writing on my body anymore and I missed it. He had pet my hair while we cuddled and I thought of how he looked around other people, how he spoke so quietly. I opened the toy chest and got my app controlled vibrator.

True facts? I've done a lot, but I had never actually, somehow, gotten the occasion to play around with someone I worked with while at work and the thought suddenly seemed pretty damn exciting. The best part about smaller wireless vibrators is that you can just wear them and all it takes is a phone app. I found him at the door, wondering what I was thinking in deciding to play this game when I was already worked up around him, wondering if I wasn't a little bit crazy by the time I got to the door and passed security. I had gotten there early and I was hoping to God he might get there early too because this was spur of the moment.

He smiled when he saw me in the atrium and returned the hug I gave him because he was around other people and that's how he acted around other people and- I tightened around the vibrator inside of me. "What's up, Lily?"

I pulled him to the side, biting my lip. "I thought I could show you something today. You got your phone?"

There must have been something in my voice because his eyes lit up at whatever I sounded like. He handed me his phone and unlocked it easily. It didn't take long. I downloaded the app and connected it to my toy, then knew I should probably test it. I braced myself for it by holding his hand and trying to not be too obvious. I wasn't usually a shy person about anything but Jesus, I was at work.

I whimpered when it worked, a low setting making everything so much worse with the tease, then turned it off. "Lily, what are you doing?"

"Having fun," I answered hoarsely. "Okay, that app is what it looks like when you get a chance. Also, I have a story to show you that I thought you'd love." And I had to make myself do that last part because I knew, based on what he'd told me so far, exactly what kind of story might really rile him. I pulled it up on a webpage and then pulled up the app again so he'd see it first. "You'll like both of these."

He gave me a shy grin and did that cute thing where he ran his fingers through his hair even while he managed to look bashful and puppy like. "Yeah?"

"Yeah. Shit, I have to go. Oh! Also." I turned and smiled at him reassuringly. "It's a dull day today where I won't see a lot of people."

He gave me a curious look and then I had to leave him, missing him already and how sweet he acted. It took until noon before I didn't think he was so sweet anymore.

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Extended penetration is a really fun thing. It's just made for devious potential. Okay, for instance, if you fill your pussy with something like anal beads (I'm just saying those because I've always found them easier to keep inside me) and then you masturbate with them and leave them in, you'll fall asleep really easily. Some time during the night, you'll wake back up and, at first, for just one twisted second, you won't even remember or quite feel what's up. You'll know something is different, but you're still half asleep. And then you'll shift and it hits you all at once.

How wet you are. How bad it aches. How you need and burn and the funny thing is, you don't even want to alleviate it just yet. You really want to let it sink in because when you're that worked up, you feel sexual as all hell, so much that you feel sexy by proxy and you like it.

For an hour and a half, nothing happened and I turned used to the sensation. Of course, I was awake so I didn't have that half asleep feeling and in some ways that made it worse. The toy was large enough to be torturous but when I walked around my office with it and sat down with it, the movement made me grow accustomed to it. Until about 9:30.

When it went off for the first time while I was flipping through ad ideas for a new project. I jolted with a shock at my desk and clasped the side of it, hiding my face behind the desktop screen and biting my lip to keep from crying out. I managed to keep it down to a whisper. "Jesus fuck." I was crazy. I was definitely crazy. Somehow it made these things hotter that I had to initiate them. I had had Doms make me walk to punishment or exhibition humiliation before, had them make me ask for it, had them refuse to tie me down because that made it too easy to not move.

This was somehow worse than every last one of those things. I didn't just have to ask for it. I had to give him control and show him what to do. It made it even more twisted that he was so shy actually because then I also had to think about every step of what I was doing. "Oh, Jesus." I tightened my grip on the desk when the setting went up, whimpering, looking out the clear windows of the office to make sure no one was paying attention and they weren't. But the thought that they could was enough and I tried to still my movements where I was shifting eagerly with the pleasure.

He shut it off and I couldn't stop a breathless laugh, along with a soft curse at the pain of being teased. "Now, that's just not nice." But the words were playful and exhilarated. And you might say that I could easily go to the bathroom and stroke my clit to one hell of an orgasm, but that would be cheating. I wanted him to feel more control to see if he liked it and getting off seemed counterproductive. Besides, it wasn't actually that bad if I worked to focus on what I was doing, even if it was a boring day.

It started again at 10:15 and, wouldn't you know it, it was the first time I had ventured from the office to find another person for an idea. I froze mid walking and had to think through where I was going, what I was doing. The need from before only compounded and I wanted to curl up at his knees again while he stroked my hair, then felt a rush that that was what came to mind. It made me think that I had set out to train him on these things and it had come back to bite me because the first thought I had when I felt like that wasn't about how he was so subdued around other people. It was how he pet me, how his eyes came alive when he hurt me with the clamps, how he just naturally loved it.

I went and found him at lunch time, where he spoke with someone else and he was soft and quiet again and I felt this weird disconnect when he noticed me and his eyes lit up with that mischievous spark, but when he spoke to his friend he was still the quiet version. It made me shiver, made me remember how turned on I felt to watch him be like that with other people while I had his marker writing under my shirt. Then that warped into the way he had lost himself while fingering me, how he hadn't even thought about it and God, he'd been vicious with his fingers. Goddammit, I didn't have a marker at the moment...

Improvising. I waited for him to finish and we skipped eating that day because I grasped his hand while he laughed, when we were alone. "Where's the guy's bathroom on this floor?"

His amusement turned even more playful. "That way."

Even then, he still let me lead and I tugged him into one of the bathrooms, locking the door behind us before I grabbed him by his shirt collar and kissed him, hard, biting kisses. It was messy and great and he made a low sound when I clasped between his legs and felt how hard he was off what he'd been doing. God, he'd loved it and that was both good and bad for me. Good, because I got to play this game again. Bad, because he was a fast learner... and I had to play this game again.

I lowered myself, making sure I didn't actually kneel on the floor, making sure I didn't mess my clothes up, while I undid his jeans in a rush and frantically tugged off my shirt and bra. I stroked my hands over my tits and tugged my nipples because I couldn't stop from some kind, any kind, of stimulation. But then I thought straight and jerked him off.

I didn't have a marker with me for him to write on me, but I could wear his cum. I gasped with a shock when I felt the vibrator start inside of me on a high setting, having been so intent on what I was doing that I hadn't been paying attention to him. The force and rock of vibration made me clasp his thigh and bury my face in his denim, loving the feeling of being lowered like this in front of him. What was better was all those talks and all those cuddle sessions? They might have seemed innocuous and innocent, but they made him very used to certain habits, so used to them that even with his shy nature and being in a work bathroom, he was just fine with doing those.

Like pulling my hair with his free hand so that I choked with ecstasy, shivering around the vibrator inside of me, around the waves of teasing pleasure. I jerked him, looking up at him and he looked down at me, his eyes sparking with that sadistic interest that I had learned he got when he was thinking wicked thoughts. "What are you thinking? Oh, please..." I shuddered with the waves of hot desire, the vibrator loud in the quiet.

He hesitated like he always did before he finally answered back and all those conversations and all that writing had made him a lot more comfortable. "I'm thinking that you're technically my boss, but right now you're just my little pet slut."

It was the first time he'd ever said anything that direct and it was enough to make me squeak and bite his jeans while I orgasmed, writhing at his knees, working his cock all the harder. I felt it when he swelled with his blood flow, when he got impossibly hard, and I shifted hurriedly, raising my head back and making sure my hair was out of the way. He made one of those low sounds that made me burn and then pulsed in my hand.

Cum pumped onto my tits and I couldn't stop a satisfied smile from the fact that I had pleased him. "Jesus, Lily," he said quietly, stroking my hair. He used his phone to turn off the vibrator with his other hand and I stood, laughing a little when my legs shook. I stroked my tits, rubbing his cum into them, trying to make it dry there faster. His eyes lit up when I did, catching on.

"That was fucking amazing. Also, I need to carry a marker from now on so you can write on me some more."

He laughed and watched me put my bra and shirt back on. I had been wearing a camisole and jacket outfit, so when I put the shirt on, cum stuck to it and made it wet so that I felt dirty in all the good ways. And then I covered it up with my sparkling jacket, like putting on my good girl mask. Alex looked like he was beside himself with dirty thoughts with me. "You should come over tonight and we should get condoms."

"God, yeah, I should do that." I giggled at his tone, at how his words were so wicked. He went out into the hallway first and messaged me to tell me I was clear.

The vibrator went off again an hour later and Alex messaged me. I really like this story.

It made me grin, even while I shivered at my desk all over again. It was a hard humiliation story with all the extreme tags I thought he'd like. That night was another breaking point, like the night he'd finally rushed to say he loved my filthiest pictures. Except that night was one of my breaking points, not his.