Chapter 6

THE CONFESSION AND EDUCATION OF BARBARA NICOLE CHIPMAN

Written by Barbara Nicole Chipman

My pulse was racing. There were so many unknowns to the questions I had. I didn’t even know what questions I should really be asking. Tonight I asked my brother to take control of my life, my destiny, and my body. I asked him to shape me into something other than the silly girl who was obsessed with rules, timeliness, and order.

There were new desires awakening in me – very perverted and delicious desires. I was feeling curious about exploring all of them and timid about admitting it. I was still unsure of myself and where my new quest of self-discovery would lead me. All I knew for certain was that my brother had taken the role of my keeper, guardian, and now Master quite seriously.

I pleaded with him to let me shower and freshen up before he began what he was calling my inspection. My pussy was soaked. I’d never been this turned on before. The last time I even came close was accidentally discovering the go-cart motors at the Family Fun Center in Chicago vibrated in ways that sent shivers down my spine.

My nipples were so hard they literally ached, and any time my brother tweaked or pinched them, he was rough. Joe wasn’t being mean or brutal with me. He treated me like a specimen to be studied. My brother pulled my nipples and seemed to be measuring them – testing their elasticity. It was playful and curious and a little painful. I loved it.

“I am sorry I’ve got such small tits, Master” I was not proud of my chest. My little sister was already blooming compared to me. I had nothing hanging down like Becky or Candy.

“I love your mosquito bites!” Joe smiled. He said he loved how puffy my nipples were, and he bit one of them. I was not used to be handled like a rag doll. Most boys would have asked before they bit me but not Joe. He just did it, and that secretly thrilled me. I think he could tell from my face how excited I was.

This was all new to both of us. We were both clearly afraid to say everything we were thinking. I knew Joe was trying to seem experienced, and like he already had a journey map for where we were going. That was for my benefit because I am so much like my mother. I love to plan our family vacations, and I thrive on knowing where we are going before we leave.

My father says he plans all day at work, so he prefers to be more spontaneous when we go on vacation. It drives me and my mother bananas.

Joe stuck his finger inside my pussy. “This cunt is NOT a hooha - not anymore! It is just a cunt! A slit, a cock hole, a cum hole. What is this called, Barbara?” He asked me.

I felt so dirty saying the word cunt out loud. I was afraid to hear it escape my lips. I was worried my mother would hear and come into the room.

“Say it louder,” my brother insisted as he wriggled his finger inside of me. No boy would have dared just reach out and play with my pussy even in the heat of my most passionate makeout session. I’ve not had many, but they were always in the dark, and he had to work at it to finally get my permission to go this far. Joe just dug in with his finger like a worm claiming its hole. He tapped my clit and said that it looked like it was telescopic. I have three folds coming out of my clit that end in the tender part of my nub.

“Cunt, Master” I said. He told me that I did well and to never call my pussy a hooha again.

“You may as well get used to being naked in my room. You are never to wear clothes in here,” he said.

“What if Ariel or Kevin come in, Sir?” I wondered out loud. I didn’t want to even suggest the possibility of our parents walking in on us. My father never visited me in my room. My mom usually knocked, but on laundry day, if I was sleeping in, she might. I wasn’t sure if she would afford my brother the same level of privacy. My mom tends to hang around and snoop quite a bit into our lives. She means well, but she is tenacious about it.

“I am sure Ariel has seen you change before?” he asked. I shook my head that she hadn’t. We’ve always had our own rooms. The Simmons family lived in close quarters and were probably used to seeing each other naked for convenience reasons. It just wasn’t something my sister or even my mother and I had ever done since I was little.

“I will give that some thought,” Joe said. I didn’t want to pressure him to have all the answers, but I desperately WANTED the answers now before we started and made a mistake we couldn’t erase. If we were caught without an explanation I couldn’t imagine having to confess to my parents that I was my brother’s willing trainee sex-slave.

“I am sure Kevin would get an education on the birds and the bees and female anatomy,” Joe said as he slipped his finger out of my pussy and pushed it into my mouth so that I could suck it clean for him. I wasn’t used to tasting myself, but I have to admit I liked the flavor of my pussy. “I am certainly enjoying it!”

My eyes grew wide with the hint that Kevin could ever see me like this. It was one thing for my older brother to control me. I didn’t want to be Kevin’s toy as well. He was immature and gross! Joe was just winding me up – at least that is what I told myself.

He pulled my ass cheeks apart roughly. I apologized that I probably smelled sweaty. He told me not to worry about it and that was part of why he wanted to assess me without letting me shower first. “I want to see the real you. I want to drink you in, I want to smell you, I want to taste you,” he assured me. Joe placed his lips at the base of my pussy lips under my anus and gave me a sweet kiss that tickled my spine straight to my brain.

“I like how polite you are, sis,” Master began tapping my butthole. It quivered and puckered for him. “You are a real tight ass, you know that, sis?”

“Yes, Master,” my face was turning red. I was mortified. I’d never considered the butt to have any sexual implications, until tonight. The girls winked their assholes, and the men seemed fascinated that they were willing to expose such a private part of their bodies. I was fascinated that they were so willing to, but for different reasons. It was something I would never have even considered showing a man. I didn’t know guys would want to see the place I used, to do my business.

“This is your shit hole, your cum hole, your asshole, I’ll even let you say butt hole, but I don’t want to hear any baby words for it,” My brother insisted as he tapped my dry butthole. It was so impossibly taboo to imagine anyone touching me there and demanding I call it a vulgar word.

“You asked me to train you as a three-hole whore. Is that what you still want?” He asked me to tell him I still wanted this.

I remembered Harlan calling his wife a three hole whore. I hadn’t explicitly said that was what I wanted to be. I had implied that I wanted to obey my brother, though. “If that is what you think is best for me, Master?” I answered, shivering in anticipation and lust at the idea that I’d do it because it’s what Joe wanted.

The thrill of admitting that I wanted to be trained as a plaything and to have all of my holes used and filled washed over me like a wave followed by the anticipation he would either tell me I was a nasty bitch or that he wanted me that same way.

Joe didn’t respond right away. I couldn’t see his face because he was squatting behind me staring up at my asshole and playing with it. I wondered if I had said something wrong. I was afraid I should have said simply told him yes.

“Good answer,” he finally replied. I felt something other than a finger slide into my asshole. I’ve been to the doctor before and had pelvic and proctology exams. It was never pleasant and certainly not pleasurable to be poked and prodded in my private places by a doctor. I realized my brother had inserted a sharpie marker into my butt.

“That’s it, just relax your sphincter. Don’t fight it!” he said as he worked it in and out. I apologized profusely that my cunt was dripping now more than ever, my own apology embarrassing me even more as I listened to myself apologizing for oozing my juices. All I could smell was my own hoo ... pussy!

“I bet Candy could fit at least thirty of these in that nasty asshole of hers. Do you think you could ever fit thirty in yours?” he asked.

“No, sir,” I replied breathlessly. I imagined thirty magic markers packed up my asshole, and it seemed incredibly wild. I was so confused – did Joe want me to be like Candy and Becky? Did he want me to be something else but capable of the same physical acts as them?

“Does it hurt?” Master asked as he tapped the marker and seated it firmly into my asshole.

“Yes, Sir,” I lied. It didn’t really hurt. It was just so new to have something poked into my asshole that I assumed it would.

“Do you like it?” he asked. It was a curious question considering that I just told him it hurt.

“Yes, Master,” I admitted. It did feel kind of good – like I was full.

“I will have to see how long we can leave it in. Your hole training begins tonight,” he promised. Joe reached between my legs and grabbed a tuft of my pubic hair. “This will be shaved soon. I want all the hair off your body except for your head. That includes all this peach fuzz on your butt cheeks.”

I didn’t even realize I had peach fuzz on my ass. He told me that my cheeks reminded him of a Georgia peach because they had cute dimples. I felt like Joe was sizing me up like I was to be his meal. It felt like my brother wanted to consume me. There was something terrifying and simultaneously electrifying about being the sheep under the wolf’s gaze.

I felt like I was his prey, and he had caught me, and now he could do whatever he wanted with me. It was deeply satisfying. It helped that Joe was saying all the right things. This was as new to him as it was to me. My brother’s decisiveness made this all feel like a natural conclusion to our evening and not an awkward sexual encounter.

Our evening was far from concluded. Joe retrieved some household objects while showing me the ready position. “This is so you will be ready for anything I want,” he said. He made me stick my chest out – as much as I could. He left the magic marker in my ass. He had me spread my legs and put my hands behind my head. I naturally interlaced my fingers as I cradled the back of my skull. It felt strangely appropriate to stand this way.

He said that this is how I will get into the mindset of being ready to do as I am told. I wasn’t sure if he’d ever tell me to do this at school or out of his room. Would I have to do it fully dressed too?

Then he left me in his room. I could have stopped holding the position and nosed through my brother’s things. I assumed that was what Candy or Becky would do if they were unsupervised in the same position. I held the position while he looked around the house.

I was surprised with what he brought back. He applied rubber bands to my nipples and wound them tightly to force my nipples to constrict. It felt amazing. I could not close my mouth while my brother bound my tits.

My mother usually does our laundry. She asks me to help and I do when asked. Even though we have a state of the art washer and dryer, she likes to hang certain clothes on a clothesline in our backyard. She says the fresh air and sunlight makes them feel fresher than dryer sheets. It was the only reason Joe had been able to come up with wooden clothespins – the kind with little jagged teeth that bite.

Joe snapped two of them over the rubber bands on my nipples, and when they sunk their wooden teeth into me, I hissed.

“Does that hurt?” he asked.

“Hell yes, Master,” I closed my eyes tightly and had to work against the urge to flick them straight back off again.

“Good. Pain is part of the training process. If everything was pleasure, then it would be me serving you. I like how you look with these on,” Joe said. He made me open my eyes and look at him. The pain was fleeting, and I’d dealt with it. After he said that, I felt more comfortable and even gazed at them as if appreciating new jewelry.

Then he applied a clothespin to the hood of my clit – the telescoping skin flaps at the top of my pussy lips. OMG! I nearly fainted. I thought I would scream or panic, but instead, I creamed myself. I had what had to be the first endless orgasm of my life. I got weak in the knees and gushed.

My brother couldn’t contain his laughter. He said it was unexpected but a good sign. “I think that may not be a punishment after all. It’s a good thing I plan to give you the rules tomorrow,” he chuckled.

My brother made me hold my mouth open while he examined my teeth. I was proud when he said there were no cavities. I asked him why he was looking at my mouth.

“You are a three-hole whore and you are my property. I am going to look over every crevice of your body tonight. I want to see your boogers, your tonsils, your guts. I am taking a look under the hood. Is this not what you wanted?” he asked.

I felt like I could have told him it wasn’t, and this would all abruptly end. “It is what I wanted, Master. Is it what you want?” I asked him.

Joe looked amused by my question. “That remains to be seen,” he laughed.