Chapter 15: More Encouragement

"Here's your first assignment, Paul: Filing papers!" Rachael said.

It was Monday, my first day as Rachael's 'organizational assistant', and I was in her office getting instructions.

"My god, Rachael, I never realized how bad things were!" I said. Papers and folders where piled in stacks all over her office, with a couple of them as much as three feet (1m) high!

"This isn't the worst of it, come with me," Rachael led me to the office next door. "See why I need help?"

The office next door was completely full. Only a small path led inside, all the rest of the available space was stacked high with folders, papers, and binders.

Rachael smiled at me. "The best part about having you as an assistant is that you already know our company and customers so well. It's fantastic, because there's so much I can use you for."

I shifted, feeling uncomfortable in my new role. Should I allow myself to be 'used' by my boss?

'But it's only temporary, ' I kept telling myself.

That night, I was kneeling on the 'beck and call' pillow when Janice pulled out the spanking paddle.

"It's time," she said. "Stand up and bend over."

"Janice, please?" I whimpered as I got into position.

She walked behind me and took a couple of moments to caress my buns through my nylon panties. Then, suddenly, she pulled them down.

"This time, we're spanking your bare bottom," she said.

"No!" I cried.

The panties slipped down my legs and puddle around my ankles.

Ignoring my pleas, Janice gave me my spanking, eleven of them, just like the night before.

And my god but it hurt! You wouldn't think that a thin pair of panties would make any difference, but it did.

And afterwards Janice made me stand there, my ass bright red and tears spilling down my cheeks.

"Will you submit to my demands?" she asked.

"No..." I said, sniffling.

Janice smiled. "Very well! You refused yesterday and you refused today, so that's a minimum of four more spankings you will have to endure!"

"No," I protested. "Please!"

Janice held my head in her hands and gently kissed my cheek. "Every day you refuse means two more days of spankings added," she whispered into my ear, causing the hair on my back to rise up.

"I don't care," I said, with false bravado. "I can take the spankings."

"I thought you might," Janice said with an evil grin. "That's why I have prepared more 'encouragement' for tomorrow."

As I knelt down between her legs to lick Janice to orgasm (three times!), I wondered what my 'additional encouragement' might be.

I found out the very next morning.

"Here's your bra for today," Janice said, sweetly, holding it up. "Welcome to your new 'encouragement'."

I looked at the bra, shocked. The cups were lined with thumb tacks, all pointing in, towards my chest.

"Come on," Janice said, "be a good girl and put this on."

"No..." I gasped. As I looked closer, sewn into the center of each cup -- positioned directly over my nipples -- were bristle brushes, each about the size of a silver dollar.

"Oh, you like it?" Janice said, sweetly. "I was so lucky to find a seamstress who could make it on such short notice. Now come on," she held the bra out by the straps, open, thumb tacks pointing towards me, "slip this on. Let's strap on your encouragement."

I took a step towards her, but hesitated. "Please, no..."

"Remember your oath, now come here."

I held up my hands, "please..." I pleaded one last time.

Janice slipped the satin straps over my arms and up my shoulders. The fabric of the bra was satin/polyester blend, and just a tiny bit stretchy. The construction of the bra was like a sports bra, with wide straps, and a curiously high neckline, front and back.

Janice turned me around, pulled the bra tight around my chest, and then fastened the hooks, one by one.

"Here, we'll set the hooks to the outer-most row of eyes," she said.

"You mean, this is the loosest?" I asked. As Janice pulled the bra snug around my body, I felt the points of the thumb tacks in the cups press gently against my breasts, and the brush bristles rested lightly over my sensitive nipples.

"Yes, this is the loosest. If you still need more encouragement tomorrow, we'll make it tighter. It has 5 settings."

"Five!" I gasped out loud. Even at level 1, the tack points were pressing into my skin. It was a light touch and I knew that it would never break the skin, but still it was already uncomfortable.

I felt Janice do something with the bra in back, and after a second I heard a soft snick.

"What was that?" I asked, worried.

"This bra is so great," Janice enthused, "it's got a locking feature. Isn't that cool? I just secured it with a little padlock. Now, the only way you can take it off is to cut it off. And of course, if you did that, I would know, wouldn't I? And you just know that if I ever found the bra to be damaged, your punishment that would be 100 times worse. And don't think I wouldn't!"

I shuddered at the thought.

Janice turned me around, "and now here you all, all locked in to your special encouragement. And look! With this high neckline you can't even slip the straps over your shoulders. Isn't that clever? Now, give me a kiss."

Janice pulled me in close and gave me a deep kiss. It was clear that she had become excited by my discomfort.

And then, to make matters worse, Janice pulled me into a hug.

"Mmmh!" I gasped, feeling her breasts press against my bra, pressing the points harder against my skin.

"Do you like that?" Janice whispered into my ear. "Want more?"

I thought briefly of people who slept on a bed of nails, and how the nails wouldn't break the skin because there were too many of them.

"Just think," Janice continued, "tomorrow it gets tighter. Won't that be wonderful? All those little tack points pressing into your delicate skin. Mmmmm."

"And the next day," Janice increased the pressure of her hug, "tighter still. Is it too much to bear yet? And then," she hugged me even more, "even tighter. And now just a bit more," Janice pulled me into a bear hug, mashing her breasts against my chest pressing the points painfully onto my skin.

"Please!" I cried out, struggling.

Finally, Janice released me.

I held my breasts gently and hunched over. "How long do I have to wear this torture device?" I asked.

Janice smiled. "Why sweetie. Until you agree to my demands. This is your encouragement, remember?"

Janice chuckled at me as I tried to work a finger into the bra to massage my hurt skin -- but I couldn't! The neckline was too tight.

I worked my shoulders a bit to try an relieve the pressure from an irritating bristle that was poking directly into my left nipple. "Ohhhh..." I moaned, in frustration. Now both nipples were being poked!

"Probably don't want to move your shoulders much, if you can help it," Janice counseled. "I imagine that too much of that could cause things to get a bit raw on your chest. I hope you don't have too much physical lifting to do in your job today."

"I hope you don't mind, your job is going to involve a lot of physical lifting today," Rachael said, as I reported to her for today's assignments.

I groaned. "What do you have in mind?"