Learning to Submit Ch. 18

Author's Note - This story is filed in Novels but is heavily BDSM in nature so feel free to skip over it if that's not your thing!

Thanks everyone for continuing to read and support this story! For those just jumping in here, I recommend starting at chapter 1 to fully understand the characters and background.

Thanks also to ftw752 for continuing to give me help with editing!

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I woke up Friday morning and hopped in the shower. Although I was getting up earlier now, I was pleased that I once again looked forward to going to work, after the stress of the last couple weeks at my previous job.

My first day had been pretty easy, learning where everything was and getting my new desk and computer set up. Commuting with Pat and working for Justin had been much more fun than I could have even imagined, and even my other coworkers seemed more at ease and laid back. My outfits still got noticed by the almost fully male exec team, but their eyes were friendly and flirtatious, leaving me with a bounce in my step.

Being dressed in sluttier clothes was still a turn on, and I enjoyed seeing Pat and Justin's eyes on me over the course of the day. I was less humiliated about the fact my nipples were sticking out, and more excited about knowing I was dressed this way for their pleasure.

At lunch the two of them had pulled me into Justin's office and made me strip to my stockings and garter before Justin pulled out a measuring tape and took a series of measurements. He didn't tell me what he was ordering, only that he wanted to add to my work wardrobe, and Pat had happily agreed.

I hadn't seen much of the two of them the rest of the afternoon, but Pat had tormented me on the way home and used me aggressively as soon as we were through the door and until we were both completely spent.

I was pulled from reminiscing by a draft of cold air in the shower as Pat stepped in to join me. He grabbed the body wash and poured some so it would drip down my nipples, making me moan at the feeling of the cold silky liquid teasing me. His hands were there a moment later, caressing my body and working up a nice lather as he washed every inch of me. He came back to my nipples at the end, rubbing and pinching them to make them stand out more.

"That's better," he said, continuing to tweak them. "If you notice them getting soft at any point today I want you to go to the bathroom and play with them until they're nice and hard again. I've picked a nice thin dress and I want to see them proudly displayed, since Justin asked for you to be naked under your dress today."

He washed his hair and then went back to playing with my body while I washed mine. When I was finished, he picked me up and pushed me against the wall, shoving his cock into my nice wet pussy with quick desperation. He licked and kissed along my neck and jawline, making me groan and cling to him as he slammed into me hard and fast, blowing his load just a couple minutes later.

He turned off the shower and pulled me out into a towel as he headed to his sink to shave, kissing me on the head as he secured his own towel.

"Being able to take care of my morning wood with your body is such a treat."

I smiled as I brushed out my hair. "It is for me as well, Master. I love when you take me hard and fast like that. I can feel your desperation for an orgasm and I'm happy to be your toy."

"You are definitely my toy. Perhaps I'll alternate holes during our morning showers. Push you to your knees and make you blow me. Or push you face first against the wall and shove my dick in your ass. Really use you as a toy in the mornings."

He looked over at me, eyebrow cocked, as the brush had frozen in my hair while a big smile spread on my face as I imagined the scenes he was describing.

"I would like that, Master."

"Good girl. Now finish getting ready so we aren't late. You don't want to be late, do you? You know what Justin will do if you're late."

"Yes Master." I finished brushing my hair and started on my makeup as I debated whether I should make us late on purpose just to get my first office spanking from Justin. I decided not to push my luck yet, and quickly finished my makeup before heading to the bedroom to get dressed.

I slid the long dress over my head and felt the slinky soft material caress my body as it fell to the floor. I carefully attached the belt he left out over the top, making it look a little less formal for the office.

I stepped into my heels and headed downstairs to grab my coat so we could be on our way.

We arrived at the office a little while later, and I carefully removed my coat. After being told to play with my nipples for most of the car ride, they were stiff and sensitive.

Justin poked his head out the door as I was removing my coat and asked me to step into his office for a moment. I did so, and closed the door. I noticed the little red light on his video camera was on. So he was filming this. I shivered, waiting to hear what fate had in store.

"Good morning Christy. I just wanted to ensure you were properly attired. I can see from your lovely nipples that there is no bra, but the underwear will require a more thorough assessment. Come here and bend over my desk."

I did as he asked, and he lifted the hem of the dress, peeling it up until my ass was fully exposed. He ran his hands over my bare cheeks, sending electricity through my core. I shivered under his touch, trying to understand why he affected me the way he did. Whatever it was my body reacted to, I pushed it out of my thoughts as I focused on his words.

"Such a lovely ass. I'm looking forward to caning it this afternoon after work. Are you excited about that?"

"Yes, Master Justin. I am looking forward to my first caning, although I'm a little scared."

"As you should be. You've no doubt read up on caning?"

"Yes Master."

"What you read is true. It's very painful. But I think you will like the after effects."

"Yes Master."

"Now before you go, your outfit is missing one thing. Stand up and turn."

I did as he asked and he dropped a pair of metal balls into my hand.

"These are Kegel balls. Your Master agreed to let me give these to you. The metal ones are more expensive but much more fun. Sit in that leather chair and hike up your skirt and slide them in your pussy. They will move around as you move around today, keeping your desire heightened. You might have to use some effort to keep them in, but since you do yoga, it shouldn't be an issue. If you start struggling to keep them in later, I want you to come see me. It wouldn't do to have them fall out in the middle of the office."

"Yes Master."

I sat in the chair as instructed, and slid the balls deep into my pussy, moaning as the cold metal slipped into my hot channel.

When I was finished, Justin helped me stand and led me to his private sink to wash up.

"How do they feel?"

As I walked to the sink I could feel the cold balls rolling around inside my pussy, increasing my internal lubrication. The weight of them fighting to fall out had me squeezing my muscles to keep them securely inside.

"They feel very good, Master Justin. They're definitely making me more wet."

He laughed lightly, and smiled at me. I suddenly felt like a sheep being watched by a wolf.

"By the time I see you this afternoon, I expect you will be gushing. Now, go to work. I've sent you an email with some tasks for the day."

"Yes, Sir."

"One more thing before you go. I know you've been attending yoga near your old work twice a week. Pat told me how important it is to him that you keep up your classes, but I don't want you to have to commute so far on your lunch breaks. I have arranged a spot for you in a class just up the street. I have sent you the details."

"Thank you, Justin. That's very considerate of you."

His eyes sparkled as he answered softly. "Of course. I'm happy to help."

I smiled politely as I left his office and got to work. The hours passed far too slowly, even with the mountain of work Justin had left for me. As the day went on, he paged me several times, sending me on small errands around the office.

On my third trip to fetch something he needed, I stopped and confronted him after delivering what he requested.

"Do you have an ulterior motive for all these errands?"

Justin feigned a look of innocence before giving in with a wink, and flashing me his mischievous smile.

"Such a smart girl. Of course I do. Speaking of which, your husband is waiting for you in the first boardroom. I told him you could deliver these notes to him."

"Of course, Sir."

I turned and left, heading for the boardroom. I was hyper aware of the weight of the kegal balls, and of the effect they were having on me. I sauntered into the first boardroom, momentarily confused when I didn't see Pat. As I walked in further and turned to check the back corners, I heard the door click behind me and turned just as Pat slammed into me, pressing against my body and claiming my mouth.

He spun me back around, bent me over the desk, and flipped my dress above my hips before gently pushing his cock into the entrance of my pussy. It couldn't go very far before encountering the metal balls, but he slid it in and out a few times before pulling it out completely. I whimpered at the loss and he nipped at my ear.

"Don't worry, I'm not done with you yet. I just needed a bit of your lube." His voice sounded half breathless, and I could hear the growl that came out when he was really turned on. I moaned in response to his need and held my position on the table.

I felt his cock at my asshole, and he started pushing insistently. Thanks to all the time I'd been wearing plugs, it gave way easily and he slid inside.

He rode my ass hard, digging my hips into the table edge as he thrust into me. His cock pushed the kegal balls around, driving me completely insane with desire.

In no time he was cumming, dumping his large load up my ass. He laid on top of me, catching his breath, before pulling his softening cock out. He had some wet cloths handy to clean himself up, and he gave me a gentle wipe as well.

"At least that helps with the outside mess. It shouldn't be long before my cream is dripping out of your asshole and running down your legs."

He pulled my dress down and helped me stand, pulling me to his chest.

"God I love having you here. It helps that Justin is understanding of the situation so I can get away with booking the boardroom for a 15 minute meeting with his admin."

He winked at me, and I laughed, snuggling against his chest.

"Meeting, huh? Is that what that was."

He smiled and kissed my head.

"Whatever it was, thank you, Master, for your cum."

"You're welcome, little sub. I figured a good ass fucking might make you even hornier. Was I right?"

"Always, Master. That little bit of teasing in my pussy drove me crazy and then I could feel your cock rolling the kegal balls around, making me extremely wet."

"Good. That was the plan. And I could feel them too, by the way. They felt divine caressing the tip of my cock through your wall. And they made you super tight at the end. So good."

"I'm glad my body gave you such pleasure, Master."

"It did." Pat slapped my ass hard through my dress making me yelp in surprise. "Now go get me a coffee from the shop across the street before returning to your work."

I could see the glint in his eyes and knew this task was designed with purpose. He wanted to give his cum time to start leaking out while I was still standing and walking around. I wouldn't be able to do anything to stop it, and it would be sliding freely down my legs. I shivered visibly before looking up at Pat.

"Yes Master. I'm on my way now."

He leaned in close "if you aren't leaking now you will be when you get back."

"Yes Master. My pussy is leaking now, but I expect both holes will be when I return."

"You're a good slut." He kissed my hair. "Now go. I have a meeting in 15 minutes and I'd like a coffee. If you aren't back in time please come into the meeting to deliver it. Better get one for Justin while you're there."

"Of course."

He knew I'd never make it downstairs, across the street, and back in time for the meeting. I figured this would somehow lead to additional punishment, and the thought excited me. Maybe it was the masochism Master Justin mentioned, but I liked when he made up games he knew I'd lose.

Nonetheless, I made a solid attempt to get their coffee back to the office before the meeting, and almost made it.

Everyone was just getting seated when I arrived, knocking on the door.

"I'm sorry for the interruption. I have a coffee for Pat, and for you, Sir."

I handed the cups to the two men and turned quietly to leave.

"Thank you, Christy. This meeting will be finished in an hour. Can you please swing by my office when it's done?"

Justin was playing it cool, but I knew I was in trouble for interrupting.

"Of course, Sir."

I left quickly, just catching Pat's smirk over his coffee cup. 'What a trouble maker!' I thought, as I headed back to my desk.

An hour later I was knocking on Justin's door.

"Ah, Christy, come in. Please close the door."

He stood and flicked the video camera on. The red light turned on, and I knew Pat would be able to watch this later.

"Now I know it's only your first week, but I like to ensure my expectations are crystal clear."

I fidgeted in my seat, excited and nervous to see what Justin had in mind.

"Pull the neckline of your dress down so your tits are free."

I did as he asked and he pulled out little clear suction cups. He affixed them to my nipples, and immediately I could feel them swelling in the tiny bulbs.

"Now then," he continued, as if nothing had changed. "When the door is closed for a meeting, I expect no interruptions unless it's an emergency. I realize Pat probably asked you to run the errand, but I have to punish you just the same. And since we are already planning to discipline your ass in a few hours, your tits will have to take the punishment now."

His eyes darkened as he spoke, and his voice got heavier and sexier. My pussy was already soaked, and knowing my nipples were being forced to swell before being punished was adding to the flood.

"By now your nipples should already be puffing up nicely. I know Pat has spanked, cropped, and flogged your tits before. I want to be sure you remember this was a punishment. Your extra swollen and sensitive nipples should help with that."

He reached out and grabbed the suction cups, pulling them away from my body. My nipples stretched hard before the seal broke around the little cups and they snapped back painfully.

He lifted a whip from his desk that looked like some kind of long hair. With no preamble, he set to work on my chest.

The whip was light and even when he swung forcefully it didn't have much thud, but the hairs stung with a burning bite where they struck, especially across my sore buds.

They had swollen to a remarkable size, and I was definitely feeling the difference with every swing.

After a while, Master Justin lowered the whip. I was surprised to find I was panting, trying to catch my breath. It hadn't seemed so painful at the time but I needed to catch my breath nonetheless.

"Do you know how many strokes you received for your interruption?"

"No, Master Justin."

"Well that's a shame. I shall just have to repeat them. Perhaps I'll use something more likely to hold your attention this time. Be a good girl and count for me."

Before I could see what was in his hand it was swinging towards me and the resultant smack made me cry out before counting.

"One."

"Ah, very good. The crop is a lot more painful, even with your little warmup. I don't think you will be repeating today's mistake when I'm finished."

He lifted his hand and started swinging, landing blow after blow all over my sensitive flesh. I counted dutifully, doing my best to speak up as the pain threatened to steal my voice. He danced all around the curve of my breasts, punishing every inch with his accurate blows. A moment after he landed 18, he struck quickly, landing a hard blow on each nipple before stopping his onslaught.

I sobbed out the final two numbers before lifting my tear streaked eyes to him.

"Thank you, Master Justin, for my punishment. I will do better in future."

"Good. Now one last thing before you go. Stand here and bend over my desk."

I did as he asked.

He picked the video camera up off the shelf and brought it around so it was aimed at my face.

"Tell me, little one, has your Master spanked you that hard before?"

"No, Master Justin."

"Do you wish he would, little slut? Look at the camera when you answer. "

I looked directly into the lens. "No Master Justin, I don't wish for that."

His hand landed squarely on my ass, hard enough to sting through the fabric of the dress, and I yelped.

"Would you like to try that answer again, little one? You might be able to hide things from your Master, but I was watching you carefully during, and after. Do you like how your body feels right now, after my crop decorated your pretty tits?"

I moaned softly and dropped my eyes. His hand lashed out again, connecting with the other cheek as I cried out again.

"Eyes on the camera. Answer the question."

I brought my teary eyes up to the camera, trying to block out the knowledge Pat would watch this later.

"Yes," it came out as barely a whisper, but I knew I had to continue. "Yes Master, I like how my body feels now."

"And how does it feel?"

"Hot, Master. Desperate. I want to be filled with cock, Master."

"And now, you understand the real way that spankings can still be a punishment for a masochist like you. Because you won't get cock anytime soon, and you aren't allowed to touch yourself."

I hadn't expected Master Justin to fuck me, knowing Pat's wanted to keep our relationship mostly professional. But I realized if he suggested to Pat that I should be left desperately horny and not fucked tonight, Pat would probably listen, or at least stick to my mouth.

"Do you think you're more likely to work hard and remember the rules to avoid a punishment like this again?"

"Yes, Master Justin."

"Good girl. Spread your legs."

I complied immediately, and Master Justin lifted the bottom of my skirt up over my ass. I couldn't tell exactly what he was doing with the camera, but I was sure Pat would like the view regardless.

"Good girl. Now grab your cheeks and spread them. Show your Master how hungry your little pussy is to be fucked. Tell me how hungry it is.

"It's so wet and desperate Master. I want to get fucked very badly."

I reached back, spreading myself open so everything was visible. With the kegal balls still inside and after punishment and humiliation from Master Justin, I was a mess. Not to mention I could feel Pat's cum leaking out of my ass.

"I see someone has been a naughty slut at work today? Is that what your meeting was about."

My face flamed as Master Justin casually mentioned the cum leaking from my ass.

I felt something cold drip onto my pussy and I froze. Surely Justin wasn't going to cross a line.

"Don't move."

His voice demanded absolute obedience and my body refused to budge once he spoke. He set the camera on his desk, pointing towards my face, and took the seat in front of me, crossing his hands and feet with a devilish expression.

"This is a little extra treat for your Master. One of my favorite ways to make me subs more desperate. Keep your eyes on the camera and tell your Master what you feel."

I stared into the camera, waiting. At first I felt nothing, but slowly, a chill started to spread through my pussy.

"It feels cold, Master, like ice on my pussy. But it's starting to burn, like a really cold burn. It's spreading through my pussy but it feels like it's concentrated on my clit. It's getting really intense, the burn. It's hard to say if it feels hot or cold... Oh GOD!"