Training Emily

We had been dating a month, and those thirty days were a whirlwind of beatings, bindings, and Mexican food. Emily loved carnitas from La Casa after being beaten, and she'd been snuggling into my side with a sore ass and a fat burrito four or five times a week since our first date.

I was happier than I had been in memory. I felt whole, actualized, like I was fresh from the shower after spending five days in the woods camping. Dominance with Emily checked off every box on my Slutty Bingo card. I'd pinged every fetish itch I'd stashed in the spank bank, coming back for seconds on a few of them, and in the process I'd added some new ones to the rotation.

It was in a service stairwell at work that I was taking in the view on one of my newest... indulgences. Emily was against the wall and facing it, hands pressed to the bricks, legs spread and short skirt hiked up and resting on her hips. She was wearing gifts I'd purchased for her, a pair of black cage-back panties and a matching garter. Resting in the center of the laces was a gift she'd purchased for me, a sterling silver princess plug with a shiny red gem.

My breath slipped out through my teeth with a soft hiss. The gem was catching the morning sun through a window on the landing above us, sparkling as she playfully wiggled her pale hips back at me. Just the sight of it had the blood rushing behind my belt.

"You never cease to surprise me," I said in a low, hoarse voice, then chuckled softly. Emily's face lit up like Times Square as she spun on her heels and turned to face me.

"You like it?"

"I love it."

"Did I just put a fetish on your list?!" she asked, delightedly.

"Stop squirming and let me enjoy it."

Immediately, obediently, she went back to grabbing the wall, presenting. This time, she pushed her ass out even further, arched her back even more. I knew learning she was turning me on was pushing her into that place that meant I was going to have to swat her hands out of my pants all afternoon until we got back to my place. So, I decided to have a little fun with it.

Standing, I clenched her left cheek hard in my left hand, holding her still as I pressed my growing hard-on against her ass through the denim of my jeans. She moaned, softly - she'd already caught a beating the week before after being too loud during one of our stairwell interludes and nearly drawing the attention of Bret from engineering as he'd walked by. She knew to keep quiet, hard as it was for her, especially as I let my hand lower to her cunt. Gently, I gripped it, and it nearly soaked my palm. Between wearing the plug and being in service, Emily's engine was purring like a sports car with cute glasses.

I leaned in and sank my teeth into her shoulder, pressing firmly enough to cause her to whimper and squirm, just short of breaking skin.

When I released my jaw, I slid my lips up to Emily's ear, and she trembled as I whispered, "I am going to be checking on you through the day, today. You choose how it ends, one of two ways. Either you be wearing this plug in your pretty ass when I decide to check this afternoon... or you very much wish you had been when we get back home this evening."

With that, I walked back to my desk.

Emily and I had met working together as a part of an extended project, so our work spaces were on the same floor. An hour or so after our rendezvous on the stairs, I decided to start making good on the promises I'd made with her skin between my teeth and her ass in my hands. I grabbed a couple dry erase markers and a stack of old paperwork and headed towards Emily's desk.

When I arrived, I found her in conversation with another member of our team, Jordan. Jordan was quiet and reserved, but Emily always managed to get him laughing. They were sharing a joke when I walked up. As she saw me, Emily's eyes widened and she bit her lip; she was too smart to not suspect I was planning something.

Our non-verbal communication skills were getting astoundingly sharp. A month of fucking around in public places around coworkers and friends from whom we'd kept our relationship a secret had necessitated the rapid development of ways to signal it was time to duck into the fifth floor storage room and get facefucked.

"Thought I heard you two laughing..." I began.

"Yeah, Emily was just telling me..." Jordan replied, but Emily stood suddenly, interrupting.

"I'm going to go grab a coffee from the break room," she said, walking away from her desk. She'd read the look on my face and the motion of my eyes that had instructed her to head in that direction.

As she walked by me, I shifted on my feet so as to nudge her, giving it the appearance of her walking into me accidentally. When we made contact, I briefly pressed my arm against her breast - just a quick guilty pleasure - and then I dropped the pens and papers I was holding, tipping them so as to ensure they'd fall in every direction.

"Shit!" I said, stepping back.

"Whoa, careful!" said Jordan, getting onto his hands and knees, helping gather papers. Emily looked me right in the eye as I smirked at her. Then, she got down on the floor as well, positioning herself between Jordan and I with her head facing Jordan and her ass in the air, facing me.

I knelt down beside and behind her, keeping her body between our third wheel, and as he and Emily went about the business of collecting what I had "spilled", I let my hand slowly slide up the back of her leg, dragging my palm against her skin and feeling goosebumps rising quickly. Taking just the briefest of moments to slip the tip of my index finger into and out of her pussy, catching my breath and feeling my heart start to race when I realized that any of our coworkers walking by at that moment would see me rubbing between her legs, I continued my exploration. Emily was still wearing her plug.

Early on, she had gleefully serviced me with her mouth one afternoon in the park, daring me to stop her as she sucked and licked eagerly near a walking path. A small row of bushes had been all the privacy I'd been afforded as she took me in her throat to the balls. I gave her exactly what she'd wanted, and as a reward for being a motivated self-starter, I'd told her that she could request some special play that evening. She'd grinned, wiping her lips, and immediately asked to get restrained. It wasn't something with which I'd been terribly experienced, but a quick stop at the hardware store gave us enough tape and rope to keep her against the mattress and helpless as I had my way with her that night. Before I'd taped her mouth shut, we'd worked out a system for her to use her fingers to tap out little signals to me - tap three times rapidly on the headboard if you start to lose feeling in a limb, tap once and then twice on the headboard if you like what's being done, tap three times and then once if you don't like what's happening.

I tapped Emily's plug with my finger, once and then twice, before I stood.

Jordan stood as well, handing me the papers. I thanked him and went on my way. Emily was last to stand and just watched me walk away. It only occurred to me afterwards that I'd made things look entirely suspicious with my sudden and silent exit, but I'd been so amped up at the time that I hadn't been thinking clearly.

I grabbed a bite to eat and headed back to my desk. I wanted to leave Emily in anticipation, so I'd avoided her during lunch. A couple hours after I'd inspected her behind Jordan's back, I felt a vibration in my pocket. I guessed it was her.

"Please... come to the storage room?" had been the text I'd gotten.

My cock was fucking throbbing I was so hard. She'd attached a photo of herself, shadowy in the light of the single exposed bulb that was the only illumination in the medium-sized closet. She'd held the phone down below her waist, bent around, her free hand hiking up her skirt. She was showing me the plug, and that she was being a good girl and still wearing it.

As badly as I wanted to join her... the thought of teasing her, of leaving her waiting, was appealing enough to keep me thinking with my brain and not my dick. I decided to play it cool.

"You'll have to wait. I'm busy." I responded, trying to convey a sense of playful terseness. I expected some sort of response, but after a few moments, none came. Imagining her sulking, bottom lip jutting out and eyes all round, was turning me on even more. I couldn't wait to...

My phone went off again. It was her, with another photo. At first, I thought she'd sent me the same photo twice, but then I noticed it. There she was, in the storage closet, same angle...

She'd taken the plug out of her ass.

I sat back in my chair. And then I stood up.

She was standing with her back against the far wall when I entered. She watched me with doe eyes as I softly closed the door. When I turned toward her, she went to say something. I immediately closed the distance between us in a stride, wrapping her throat in my fingers and clenching them tight. Her face tensed in shock, her eyes white and wide, as I leaned forward and explained the situation.

"I told you that this day would end in one of two ways. You would either be wearing the plug... or you'd be wishing you had been."

I had stopped for some supplies en route to the fifth floor. This area of the building was "under renovation", but it had been in that state since any of us had been hired, and no one ever saw any contractors come or leave. Still, as I'd stalked up the stairs from my desk to the storage room, fighting a smile so as to keep my scowl glued into place, I knew that even with the floor being uninhabited, a spanking would run the risk of having someone hear. I needed to be creative.

Without removing my right hand from Emily's neck, I used my left to pull her blouse up, slowly. The closer to her breasts I went with my left, the harder I squeezed with my right. I had practiced applying pressure in the right way so as to retain control while choking her. I wanted her to feel the weight of my hand, to feel her breath go tight, but I didn't want to injure her or cut off her air entirely. Her eyes were half-lidded and her lips slightly parted, her breathing steady and measured. I could tell from the look on her face what headspace she was entering.

I pushed her blouse up to her neck, exposing her breasts, and then yanked down her bra, freeing them. Her nipples were stiff, and seeing them that way had a similar effect on me. I had never been that fixated on nipples before Emily, but her little pink rosebuds always tightened my jeans. I also happened to know, from personal experience, that they were unbelievably sensitive. I bent slightly and gave each of them a little kiss, both hearing and feeling a whimper escape her at the contact of my lips. As I stood, I gave her the sweetest of smiles, leaned in to kiss her on the lips... and then reached into my back pocket, pulled out the metal clip I'd grabbed from my desk, and clamped it down on her left nipple.

She tried to cry out in pain, but I kept my mouth over hers. I enjoyed the sensation. Looking her dead in the eye, I clamped her with the second clip I'd brought. Her breaths were whimpers, now, and her eyes closed shut tightly.

"Awwww, does that hurt?" I mocked her, and she nodded. "Well, then. Let's leave them be for a little while. In fact..."

I reached down and slapped the clamps, back and forth, for a good thirty seconds. When she started to scream, I clamped my hand down on her neck and cut off the sound. She gasped wordlessly, fighting for air, as I tortured her tits.

"Stay. Fucking. Quiet."

I relaxed my grip on her throat.

"Yes, sir," she whispered, her eyes watering. I ran my tongue over her cheek, tasting her tears.

"That's better. Let's use this as a lesson, a lesson for clever little girls. Clever little girls who think they'll get what they want by acting out. You could have worn the plug all day and gotten your gorgeous little ass fucked tonight, but you had to have it right now, even when I told you no. Next time we'll remember this. Now. Where is it?"

She reached a shaky hand into the pocket on her skirt and handed me the plug. It was still warm. I looked at her.

"Did you wash this?"

She nodded.

"Good."

I put the plug in her mouth, removing my hand from her throat.

"You may want to bite down on something."

With that, I turned her around and faced her against the wall. I pulled her hips towards me, fighting the urge to send a cracking echo through the building by smacking her cheeks as hard as I could. That I'd save for another day. Instead, I unbuttoned the fly of my jeans and slowly unzipped them, taking my time to let her hear and to realize what was coming.

There is always the moment of doubt that comes at the worst possible times, right when you're about to kick things up a notch. You feel secure in your sadism, you've temporarily locked that part of your brain that likes puppies and babies out in the rain, but it sneaks back inside. I paused, hesitating... and then decided to let her guide me home. I knew her well enough at this point to trust her, and to know she trusted me.

"Are you sorry?" I asked. She nodded yes, still facing the wall, away from me.

"I don't believe you," I said, pulling out my hard cock. I reached up and around her head, rubbing my palms against her cheeks, drying her tears onto my hands, and then rubbing them down the length of my shaft.

"You don't deserve this, with how you've behaved, but... just a little lube. I'm not heartless," I said, as I rammed myself into her beautiful backside.

Her whole body went stiff. I saw her fingernails scrape the wall, trying to dig in. Her legs were trembling and her hips bucked forward for a moment, but she held her ground as I started to slowly thrust in and out of her. She kept her lips clamped, but she was moaning, and muffled through it was, the room was filling with the sound of it. Feeling her on my dick, impossibly tight even after a full day wearing the plug, bouncing her thick little cheeks off my hips, you couldn't have measured the amount of fucks I gave with an electron microscope.

I upped the speed as I reached around with both hands and squeezed the clamps. I felt the tension in her body through her ass as it squeezed me even harder, starting an amusing round of one-upmanship between her butt and my hands. I could feel her getting wetter and wetter, dripping onto my thighs and starting to soak my underwear. I fucked her harder, and harder, and I squeezed the clamps harder, and harder. I twisted them. I pulled them. The moans escaping her were a mixture of agony and ecstasy. I could see the flush in her skin, feel the tremble, and hear the tell tale signs : Emily was about to cum.

I lifted my hand to her mouth, cupping it. She leaned into my grasp, pressing her lips to my fingers, preparing to enjoy her release and appreciating that I was aiding her in muffling the sound. At least she thought.

"Open your mouth," I commanded in a grunt, between hard thrusts.

It took a moment to register, so I said it again, this time in a growl.

"Open your fucking mouth."

The plug she'd been holding between her lips fell into my palm. I stepped back, plug in hand, and pushed it right into her ass, moments before I knew she was going over the edge.

"Now take the rest of the afternoon before bed tonight and think about what you did," I said, as I tucked myself away, zipped myself up, and walked out of the closet.

I ducked into the men's room near my desk and cleaned up, bringing a soapy paper towel into the stall. I fought the urge to stroke off; I wanted to punch a hole in the wall and fuck that, if necessary, I was so turned on. But I needed self-control. And I wanted to save it for Emily.

I was at my desk almost half an hour with no word from her. I thought about getting up, going to her desk. The longer I didn't hear, the more the doubt crept in. I wondered if I had taken things too far. Was she upset with me? And that's when my phone went off.

"I... I think I love you," it read.

"I never knew the way to a girl's heart was through her ass!" I replied, teasing her.

"If I'm a good girl later... can I have it again?"

"Of course. This time, no clamps," I texted.

"No. Bring them," she said. And I laughed as she texted me a smiling devil emoji.