Subculture Allure: Sherry Teaches Bootblacking

Master’s Guest, Sir Steve, stayed for two more nights. This time taking Cupcake and then Sherry under his Mastery for their own evenings. Needless to say, Sir Steve was very pleased with Master’s hospitality. 

After Sir Steve left, things returned to our version of normal. Since I didn’t work the weekends, as long as we didn’t have any community events, classes or parties, I would spend my time tending to any of Master’s needs, whims or give my service to his home in the form of upkeep. Master normally keeps his girls naked unless protective clothing is needed for any tasks.  

This weekend became a very intriguing and awesome one. Master instructed Sherry to teach me how to bootblack. Sherry has typically been the only one to attend to Master’s shoes and now I was to be entrusted to share this task with her. I felt honored that Master elected me to learn and help Sherry with this task. 

We were in Sherry’s room. Being Master’s head Slave, she had a room of her own. She handed me an apron so I wouldn’t get any cleaner or dirt on Master’s body.  In times of training, I am to call her Mistress and she has been given punishment power over me per my contract and Master’s will.

Sherry showed me her kit; her daubers, brushes, creams, waxes, and polishes in her bootblacking kit. She then handed me a separate boot blacking kit.

“You’ll need these to polish Master’s boots, shoes and other things appropriately. I’m not going to let you play with my kit, but I’m happy to introduce you to this skill so that you may please our Master better. This kit is a starter kit of sorts and has a variety of things that will allow you to find your personal style or preferences while using them.” Sherry said.
“Thank you so much Mistress!” I exclaimed.

“Now open your kit and lay yours out like I did mine.” She said. With a slap from the crop against my shoulder, I heard her say “Faster! You need to move fast I don’t have all day to show you the cleaning process and Master wants results. He wants to see these 3 pairs of boots cleaned.” Sherry stated.

Wearing my apron, I hurried and set out the kit just like hers. I knew I needed to please her in these regards as I would Master, or she would tell Master and I would earn a harsh punishment.

“Grab the first set of boots and put them in front of you facing me, then go to tower position and watch me.” Sherry instructed.
I watched intently as she prepared the boot and removed the laces. I watched the beautiful curves of her body through the apron. Her nipples were hard. I knew she loved to please Master just as I do. Knowing this made me smile. The crop was sitting beside her when she grabbed it quick and smacked my hand.

I started to envision her pleasing Master by presenting him with cleaned and polished boots while on her hands and knees, naked, aside from the collar and bells on her left ankle. He would then kiss her forehead and taking the boots from her, would put them aside and use her like the slave she was. I imagined hearing the moans of their pleasure.

Sherry was very pretty. She had long blonde hair that Master likes her to keep in loose curls. She has large supple breasts with nice pink little nipples. I’ve seen her walked by her nipples clamps with a chain attached. Naturally she would be on her hands and knees. She would be almost in tears by the end of her walking. But after, she would be in Master’s arms on the living room couch. He enjoyed her by licking and sucking her nipples to soothe them.

“Are you paying attention?” Sherry snapped, bringing me out of my day-dream like state.
“Yes Mistress!” I said.

“You need to do this perfectly. Need I remind you that if you don’t, I won’t be pleased and then you won’t be allowed to touch Master’s boots unless you use your lips and tongue to kiss and lick them?”

“No Mistress! Please, I beg to learn how to bootblack. I want to please our Master, please continue Mistress.” I begged.

“Fine.” Sherry said. Then she proceeded to show me the intricacies of cleaning Master’s boots. 

“You did great little slave. I am very happy. When Master comes home from work, you will present them to Master. As we discussed, we will stop at the cleaning phase. Once you show me you can clean the boots perfectly every time, you will then be permitted to start learning how to properly polish and then subsequently present the boots as he sees fit.” 

“Thank you Mistress. Slave is happy to have pleased you.” She kissed me on the forehead and assisted me in cleaning and putting away our bootblack kits. She took my perfectly cleaned boots and set them on Master’s side table in his bedroom, ready for his thorough inspection. 

Master arrived home, those of us who were home, rushed to present ourselves to Master. He patted us on the head, handed his jacket and the wine he purchased for tonight’s dinner to Sherry. It seemed that he had had a rough day, so the girls and I wanted to make sure we relived his stress. We prepared a nice bath for Master and I kneeled in the corner or his bathroom while he bathed. Cupcake helped him bathe and Sherry finished dinner. While Master got out of his bath, I awaited to present Master with a towel. He kissed Cupcake endearingly and tossed her into the bathtub. Then kissed her again while grabbing at her breasts and slapping her ass with vigor. I giggled to myself quietly. Then Master arose from her. 

“Clean yourself up, get ready for dinner. After dinner, you will prep my hunting gear.” Master said. “Yes Master.” Cupcake giggled. Master took the towel I presented him. He kissed me on the forehead and walked into his bedroom to dress. I helped Cupcake from the tub and we got ready for dinner.

Getting ready for dinner in our household means naked, collared, and left ankle belled. Slaves are clean, smell good and look just as Master likes to keep us. For Cupcake this means red lipstick. For me, this means hair down, loose curls, with a little bit of eyeshadow and mascara. 

Dinner went well. We could see that our service helped Master calm own quite a bit. Master walked into his bedroom to grab his phone. While in his room he noticed the boots. He walked out to the dining room where the other slaves and I were clearing dishes from dinner. 

“What’s this? My boots are cleaned, but not polished?” He smirked. “The cleaning done here is immaculate. I’m quite impressed. Sherry, your student is learning quite well. I am also impressed with your teaching. I can’t wait until she is ready to finish the process and present me with polished boots.” He said. I blushed. Sherry looked at me and smiled and then blew a kiss to Master. 

He walked over to me as I was still gathering dishes from the table. He grabbed me by the hair and walked me to his bedroom. His strong hand in my hair and the other at my waist guiding me. I was already wet with anticipation.

“Your skills in service are dramatically improving. I am happy to see your progress.” He said. 

“Thank you Master.” I said as he threw me to his feet beneath him. 

“Don’t move” Master said. I didn’t. I wasn’t even in position. 

He came over and gathered my hair into a ponytail from behind me. I looked up and smiled at him. I was so happy Master was pleased. He then tied a rope to my hair and then tied that to a foot board post on his bed. This made me lay back on the rug before his bed. He took off his shirt and pants. I was already naked. He began to kiss and lick my body. My hands were running themselves all over him. I couldn’t help it. I love touching him. When he covered every inch of me, he began to lap up my juices. He kissed and tickled my clit and made me moisten even more. I was nearing orgasm when he stopped. 

“Cum when you like my dear. I want to feel you in your fullness.” He said.

“Thank you Master.” I moaned.

He then began fingering me while kissing and sucking on my clit. I moaned loudly as I began to cum. I squirted. “Good girl.” He said grinning. 

He raised up, pulled me as far as he could towards him, pulling on the tie in my hair. He forcibly held my legs apart as much as they would go. I love it when Master mixes in his rough Mastery. He began to thrust his cock in me. He was thrusting harder and harder, as I was moaning louder and louder. He moved his hands from my legs, allowing me to wrap them around him. He held my wrists down and began almost grunting. He was trying to reach the deepest parts of me. I could feel his sweat drip onto my body as I was still beneath him. 

“Harder, please Master, harder, please fuck me harder Master!” I began to scream. 

His grunting became louder. 

“You little bitch, I’m gonna cum.” He growled smiling. 

“Yes Master, I am your bitch, cum inside your little bitch please!”

“No.” He said while raising off me. He then began to cum on me while standing over me. I held out my tongue and opened my mouth wide. I was hoping to catch even just the tiniest bit of Masters cum. I wanted to taste him so bad! 

Master finally let me taste his cum by having me clean his cock with my mouth. I sucked, licked, and caressed his cock with my mouth. I wanted every last drop of his cum in my mouth. I wanted to taste him and I together. It’s was blissful! Master pet my head and ran his fingers through my hair as I did this. 

Master finally pulled me away from his cock. I looked up to meet his eyes.
“You’ve been a good girl. Now go take a shower and meet me in bed. You will be staying with me tonight. I love you.” He said. 

“Yes Master, I love you too.”

– Butch T. Unicorn