Neighbors Ch. 19

"I know, right? I thought it was really hot too. And sort of sweet."

"I think he's into you, Sarah. I really do."

Sarah looked pleased but also slightly nervous.

"Yeah, maybe. We'll see. I'm kinda bummed he can't afford me more than once a week."

Amber tapped her fingernail against her lips thoughtfully.

"Hm. Well let me think about that."

The waiter came and cleared the table, leaving a check behind. Neither of the women reached for it of course, so I put down a debit card.

"Well, I guess we should get this unpleasantness out of the way before we all take off" Amber said, reaching into her purse. She pulled out a piece of paper with lines of handwriting covering most of one side. She put it on the table and spun it around so I could see. My mouth fell open.

Every mistake I had made in the past week was listed. In Sarah's handwriting, I saw every set I had failed to complete - almost all of them occurring last Wednesday when I was recovering from my...meeting...with Ms. Sutton and her cane. Amber's small but perfect script listed every chore I had failed to complete to her satisfaction. All in all there were over seventy entries listed. My eyes were drawn to the bottom of the page. There were three spaces for signatures. The first two spaces were already signed by Sarah and Amber - the third space was blank.

"Should I sign this?" I said, feeling around in his pockets for a pen.

Sarah smirked at me while Amber laughed out loud.

"No silly" Sarah said, trying in vain to hide her smile behind her hand.

I looked between the two of them, confused.

"Uh....then...."

Amber leaned forward. I noticed again how her crop top struggled to contain her chest. All this talk of breasts had me fixated...

"The third line...is for Ms. Sutton's signature."

She sat back and crossed her arms over her breasts, waiting for me to absorb what she meant.

I paled and shook my head.

"No...no no...please..."

Amber had a slight smile on her lips.

"You want to be the best bank you can be, right? You say that to me all the time."

I gulped.

"Yes...but..."

Sarah leaned forward as well, causing her red hair to cascade in front of her face. She pushed it back behind her ears.

"And from what I saw of the marks on your ass after your last meeting with her, she seems, like me, to be very good at...motivating."

I stared down at the piece of paper.

"Does she...does Ms. Sutton know about his?"

Amber shook her head.

"No - I thought it would be a fun surprise. You need to get her signature on this page, and bring it back to me tonight. Do you understand?"

That night arrived faster than I had hoped. Eventually it was time to leave my house and head to Ms. Sutton's boutique. I allowed himself plenty of time, remembering how I was late last week. I pulled up and breathed slowly, forcing myself to relax. I knew I would do anything for Amber, but this was the most...challenging... thing I had to do - endure Ms. Sutton's cane in exchange for an almost endless supply of tailored clothing for Amber to wear and enjoy. If anything I did showed the stark disparity in our stations, this was it. My experience under Ms. Sutton's cane was painful and humiliating, but at the same time I was surprised to feel a stirring of excitement from some where deep within. Ms. Sutton was clearly a sadist, but she knew what she wanted and was willing to go to some lengths to get it, as her service to Amber showed, and something about that was deeply attractive to me. And my newly awakened submissive side longed to fulfill her needs in whatever way I could, welcoming the pain if that's what this dominant woman wished.

Sighing, I checked my watch one last time and got out of my car, making the short walk to the storefront. I admired the tasteful clothing arranged immaculately on displays and mannequins as I entered the store precisely at nine PM.

I spotted Ms. Sutton immediately. As always, she was impeccably dressed. A severe black skirt and an ivory colored satin shirt, with a dark green vest. Her sharp features were accentuated by the fact that she wore her raven black hair up in a neat bun. She was speaking with a young woman in the back corner. She noticed me enter and looked up.

"I'm speaking with an employee, Christopher. Please go to my office and I'll be with you shortly."

The young woman glanced at me curiously, then returned to her discussion with Ms. Sutton. I made my way to the back of the store, and turned down the short hallway to the office. The door was open, revealing the neatly organized space dominated by a heavy, wooden desk. The desk I was bent over last week. I shuddered and pushed the door behind me. It closed with a solid thump.

I looked around the room, seeing a few subtle changes from last week. Different dresses on the dress forms, different fabric laid out on a side table. I knew I was merely delaying the inevitable. I slowly removed my clothes, folding them and placing them carefully on an empty chair, clutching the list in my hand. I moved to stand in front of the desk, feeling cool air blowing on my naked skin. The desk was bare and clean, save for her cane and an old fashioned wooden ruler lined up perfectly parallel. I took the paper and carefully smoothed it out next to the cane before gingerly leaning forward and resting my elbows on the desktop, feeling terribly exposed with my ass facing the closed door, and waited.

Minutes went by before I heard Ms. Sutton's sharp heels clicking down the hallway and the door opening. The breeze from the swinging door caused me to shiver. I heard an appreciative sigh.

"Very nice, Christopher. Obedience makes me happy."

The door closed and her heels clicked across the floor.

"I have a few new... toys I'd like to use tonight." I flinched as I felt a sharp fingernail scraping along my bare bottom.

"I see most of my marks have faded. I need to address that immediately."

She continued to trace her fingernails across my rear for a minute, taking her time and clearly savoring the suspense before she dispensed her discipline.

I felt her reach across my body for the piece of paper on the desk.

"What is this? You may speak."

I licked my lips.

"Um...Miss Amber...and Mistress Sarah...have been disappointed in me this week. That's a...list...of the ways, specifically. Um...they...want you to sign it."

There was silence for a few seconds and then Ms. Sutton let out a low chuckle.

"Oh...I see. Well Christopher. It seems like you've been very delinquent in your duties. Very delinquent indeed. And you need correction."

She reached for the cane, and slid it menacingly across the desk. At the same time, she pressed the paper into my hands.

"You are going to read each and every line on that page."

Ms. Sutton was swinging the cane through the air now, making harsh sizzling sounds.

"When we get to the end, if you've been good and held your position, then I'll sign it. Now..." I felt the tap of the cane on my calves "Up on your toes. And let's begin."

Ms. Sutton struck with the cane again and again, after I read each entry on the list with an increasingly ragged voice. Each strike was like a fresh stripe of fire, and it was all I could to do keep my elbows firmly on the desk and read the next entry through teary eyes. I was dimly aware that Ms. Sutton's breathing was also growing increasingly loud and erratic, and I didn't think it was merely from the effort of swinging her cane. After what seemed like several minutes of constant strikes from the cane she began to slow down, grasping my injured ass with her sharp fingernails and eliciting fresh groans from me before stepping back to set up another strike with the wicked cane. It wasn't long before I was sobbing and begging her for mercy.

Suddenly I heard the unmistakeable sound of the cane falling on the ground and Ms. Sutton was pressed up behind me, forcing my hips into the edge of the desk. Both hands were cruelly fondling my bottom, pinching and squeezing and raking with what felt like razor sharp nails. I cried out again at the pain of her nails on my wounded skin. Her lean torso pressed against my back - the incongruity of her full shirt and vest against my naked skin was stark.

"Face down - flat on the desk" she growled in my ear, her breath hot on my neck. I complied meekly, pressing my forehead down on the cool surface of the desk. The list I had clutched in my hands fell to the floor as I scrabbled for purchase with the added weight of Ms. Sutton.

She shifted her weight slightly and I heard her right hand scraping on the surface of the desk, reaching for the ruler that I knew was there. She was now slightly to my left side, exposing the right half of my ass. Suddenly I gasped again as I heard the swish of the ruler, and felt a new sharp sting. She beat me again and again with the ruler, keeping herself pressed up against me. I was thankful that her close proximity kept her from making the swings with full strength, but they were still striking with painful force.

She shifted again, and her arm wedged between my hips and her side, reaching down. A second later I felt the fabric ride up my legs - she was pulling up her skirt!

"Eyes. Closed." She reiterated, punctuating each word with a strong swap with the ruler, eliciting two sharp gasps.

I started in surprise as I felt rather than heard the unmistakable oscillations of a vibrator. Because her hips were pressed up against mine there was no mistaking that she was holding a powerful vibrator against herself with her left hand while striking with the ruler in her right.

"Ohh....yesss..." she moaned above me, still pressing me down against the desk.

Despite the situation, I felt my cock try to stiffen in my new chastity device. The pain she was inflicting was clearly arousing to her. I wasn't sure why this was exciting to me too. Amber seemed adept at inflicting emotional and financial pain on me, and was clearly excited when she did so. Sarah used her punishing workouts to inflict pain as well - not nearly as explicitly as Ms. Sutton but she also seemed to delight in humiliating and tormenting me when the mood struck her, as when I was kept in her closet while she spent the night with that guy from the bar. All three women abused me in a different way. I had begged Amber to take advantage of me to begin with, completely obsessed with the way she was taking my money and keeping my cock locked up while I did chore after chore for her. Amber had shared me with Sarah in a way, and while the workouts and some of the treatment from Sarah was intense, I realized it was benefitting my life to eat better and get in shape. And while I dreaded the appointments with Ms. Sutton, I wondered if it was so different - by submitting to her I was giving her what she wanted, and finding out that maybe a part of me enjoyed this transaction as well.

Her ruler struck again and again as she moaned in my ear. She was hitting the same spot continually - the only flesh of my rear exposed as she was grinding into my side, pressing herself against me and the vibrator she held between us.

"yes...yes...yes..." She was panting now, clearly close to her orgasm. She dropped the ruler, and resumed her assault with her nails now, raking and pinching frantically. I convulsed under her, summoning every scrap of willpower to stop myself from reaching behind to stop her.

"yes...YES!!" She shouted in my ear, nearly deafening me. She went rigid for several seconds before letting out a long, shuddering breath. She rested for a minute before slowly collecting herself and stepping back. I was grateful for the break from the abuse and used the opportunity to catch my breath as well.

I heard Ms. Sutton take a few steps and pause. Then she made her way around to the front of the desk, her sharp heels clicking on the polished floor. Her voice came from directly in front of me now.

"You may look up now, Christopher."

I raised my head from the desk and looked around, blinking. I saw her begin to compose herself. Her clothes were uncharacteristically disheveled, but as I watched she smoothed her dress and resettled her shirt and vest. Her face was flushed but her eyes and lips were bright. A strand of black hair had fallen out of her bun and she tucked it back carefully.

Once she was satisfied with her clothes, she bent down and picked up the list from Amber and Sarah, placing it gently back in my hands. I shivered as she traced a hand lazily along my shoulder and back as she walked back around the desk. I groaned when I heard her bend over and pick up the cane.

Suddenly I felt the cane tap against the inside of my right calf.

"Spread your legs further"

I did, shuffling awkwardly until my legs were shoulder width apart.

"More" she said, striking against the inside of my leg again, painfully this time.

I quickly walked my feet apart until they were spread wide - almost as far as I could spread them and still keep my elbows pressed down on the desk.

The tip of the cane tapped my calf again, and then ever so slowly traveled up the inside of my thigh. I gasped as the wooden tip moved higher, and started to sweat as it came to rest on my balls, hanging down and exposed in my current awkward position.

Ms. Sutton tapped the cane gently.

"I appreciate how dear Amber's chastity cage leaves your testicles exposed. It would be so easy to cause all sorts of...discomfort...to them, wouldn't it, Christopher?"

I blanched.

Suddenly the tip of the cane flicked down and then up again, delivering a light but sharp blow directly to my balls. Pain bloomed from my testicles up into my belly. I couldn't stop a whimper coming from my lips.

"You may speak, Christopher. Answer."

"Yes!" I practically shouted, eager to comply as quickly as possible. "Yes, it would very easy for you to...cause discomfort...to my balls."

She chuckled.

"Well, let's see how you do this week. If you bring me a list like you did today...such a disappointingly long, long list of your mistakes...you'll leave me little choice but to experiment with your testicles. So if you wish to avoid that, you should stop being so sloppy in your service to both Amber and Sarah. Understand?"

I nodded fervently.

"Yes, Ms. Sutton. I understand completely."

"Good." I heard her take a few steps to the side as well as the unmistakeable whoosh of the cane being swung through the air in a practice swing.

"Now, where were we?"

Finally Ms. Sutton was finished. Like last time, my ass felt like it was on fire and I had lost count of the number of times I had begged her to stop. The piece of paper in his hand was discolored from my hot tears.

I had to grit my teeth as I pulled up my underwear, the soft fabric feeling like burning sandpaper on my striped butt. Ms. Sutton relaxed, perched on her desk, and watched me coolly as I dressed.

"You did well tonight, Christopher" Ms. Sutton said, idly brushing a speck of dust from her immaculate skirt.

I blushed as I knelt down to lace up my shoes.

"Thank you, Ms. Sutton."

The incongruity of the moment wasn't lost on me. She had spent the last thirty minutes caning and spanking me with a ruler, and now I was thanking her. She was smirking slightly as I stood up, holding the list of infractions in one hand, and an expensive looking ink pen in the other.

"Shall I sign this for you now?"

"Yes, please." I heard a faint note of pleading enter my voice.

With a flourish, Ms. Sutton signed her name on the line and handed me the paper.

"Same time next week."

I nodded and walked out of his office, dreading the drive home and the car seat. I made a note to buy an inflatable pillow to keep in my car for Tuesday nights.

The car ride was indeed painful. I used my legs to try to support as much weight as possible but still my rear was burning the entire time. I sighed with relief when I pulled into my driveway.

Clutching the signed paper, I walked across the yard to Amber's house. I knocked on the door.

A minute later she pulled the door open. She had a towel wrapped around her breasts, and another towel wrapped turban-like around her brown hair. She was dripping wet and had clearly just come out of the shower.

"Yes?" She said, giving me a knowing wink. "You have something for me?"

I nodded and held out the signed paper. She took it and made a show of carefully examining Ms. Sutton's signature before nodding and tossing it over her shoulder.

"Try to get some sleep" she said to me, not unkindly.

"Thank you, Miss" I said, and turned to leave.

I nearly screamed as she suddenly slapped my ass.

"And clear your schedule on Friday. No going to your office, you're working for me all day. You have a lot to do to get ready for your party!"

I heard her front door close behind me.

My alarm startled me out of a deep sleep at 5:30 AM. I rolled over onto my back and immediately regretted it as my bruised and battered ass touched the mattress. Groaning in pain, I staggered out of bed and switched on the light in my bathroom. My rear looked about the same as last Wednesday morning. Bright red lines alternated with dull purple and black bruises covered my ass and the upper part of my legs. I lightly rubbed some neosporin cream into the wounds, wincing in pain every time my fingertips lightly brushed my injured flesh.I thought that it might be a good investment to get a standing desk installed at work for the few days after my visits with Ms. Sutton when it was particularly painful to sit. I couldn't face the thought of a shower streaming water onto my ass and figured I could just do a sponge bath in the bathroom after my workout with Sarah. It was a Wednesday, meaning I needed to get to the gym and do my hour of cleaning before she arrived.

I knew what to do this time, and despite moving gingerly because of the caning, I was able to get the weight machines and the bathroom cleaned, the carpet vacuumed, and the towels going in the laundry before Sarah strolled into the gym, whistling merrily and brandishing her Starbucks cup. The sun was just rising behind her and shone through her fiery red hair as she tossed her gym bag on the reception desk. She was wearing red spandex gym shorts that were only four or five inches long, exposing her powerful thigh muscles and her long legs. Instead of her typical jog bra she was wearing a tight white tank top with thin spaghetti straps. My eyes widened as I saw the clear outline of her nipples through the thin fabric covering her small breasts. I was thankful yet again that my new chastity cage didn't contain the cruel spikes that tormented my dick so frequently around Sarah and Amber.

"Heya, Chris" Sarah said cheerfully as she took a sip from her drink. "How's it hangin'?"

"Uh..."

"Never mind" Sarah interjected. "I think I know - small and locked?"

She laughed at her own joke as I grimaced, as much at the poor joke as her humiliating words. I consoled myself with the thought that she seemed to be in a great mood.

"I'm in a great mood" She confirmed, as if reading his thoughts. She stretched, standing on her tip toes and reaching for the ceiling. I watched as her motion pulled her tank top up slightly and admired the tight muscles of her stomach as well as how the fabric pulled even tighter against her breasts.

"This extra hour of sleep every other day is doing wonders for me."

"Yes mistress, I'm glad" I said, realizing it was true.

"Aw, you're sweet." She patted me on the cheek as she walked by, glancing around the gym. "Looks like you did a good job, too."

A thought seemed to strike her and she looked at me curiously.

"Hey, how is your new cage? I can't believe I didn't notice it yesterday when I had you on the scale. I guess in a way it's just becoming normal to me."

"Um, it's just fine mistress. I mean it's pretty similar to the old one. Just a few minor differences so I'm not surprised you didn't notice."