The story of Karri-Ann

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

An hour passed, and I considered getting into bed to take a nap. The door buzzed. I scurried over to it and pulled it open. The desk I had been sitting in was gone. It had been replaced by an open chair on the other side of the room. I looked at the teacher desk, but Sarah was not there. I wasn't sure what to do. I walked over to the desk and pulling out the apple I had stowed in a fold of the skirt I placed it in the center. I walked back over to the chair and sat down. I tried different positions of sitting, I was become quite amused by what sitting positions made me look more feminine. One made me look down right sluttish, and I giggled. I crossed my legs as I had seen other woman do. I uncrossed them, and decided to sit how I did this morning. I placed my hands in my lap and straightened my back and held up my head. I watched the clock that had been placed on the wall since I had taken lunch. The minute hand slowly ticked away. Ten minutes later, the door opened in the other corner. Sarah walked in reading a book. She sat down at the desk and looked up at me. She opened her mouth to speak, and then stopped. She gave another look at me then noticed the apple. A broad smile erupted on her face.

"This is wonderful, Karri-Ann!"

Sarah beamed proudly and stood up, turning to the board she wrote in the left hand side, "Merits".

Sarah placed 2 hash marks in that column. Sarah walked over to me.

"We will be working on your walking this afternoon, and also your voice projection"

"Now, Karri-Ann, I want you to walk to the other end of the room and then back to me."

I stood up, curtsied to Sarah, then walked to the end of the room and came back. A slight smile was on Sarah's face. Okay, she sighed.

"You are walking like boys, think of all women you have seen; now think about how they walk."

Sarah continued her lecture. "When we walk it is one foot in front of the other, not like your trying to sky down a hill."

Sarah demonstrated, showing the difference. She pointed to her hips also as she swayed them when she walked. I tried it again, over emphasizing the sway. Sarah shook her head, and then demonstrated again. On the third attempt, Sarah made an approving remark. She waved me on, I walked towards the other wall and noticed how much easier it was becoming. After several more back and forth trips I was able to relax and make it back and forth faster.

"Slow down, we don't go fast, after all, we want the boys to notice us for as long as possible" Sarah pointed out.

"Okay, you have the mechanics of it; now let's see if we can get you to do it with style."

Sarah walked to her desk; I continued walking around watching my hips and feet how they moved. I paid to much attention to my hips, I tripped and fell over. Sarah burst out laughing, and then pointed out that I needed to pay attention; she rolled her eyes at me. I gathered myself and stood up, beet red in the face and a sheepish grin. Sarah walked over with a dinner plate in her hand. Reaching up she placed the plate on top of my head. I reached up and held it there. Sarah told me to take my hand off of it. I cautiously did so, concentrating on keeping it balanced.

"By the way, each plate you break is 10 demerits"

I almost lost the plate then. I cursed in my head.

"Now go ahead and walk down and back" she pointed to the other wall. I carefully began taking small steps and put out my arms to balance myself.

"You are trying to fly? Put your arms down like before and you can take little bigger steps then that."

I lowered my arms, bent my hands at the wrist and began walking. I reached the other side, and slowly pivoted around. I started the trip back. I breathed easier when I made my final step in front of Sarah. Sarah motioned me to do it again. I made the trip 2 more times. I felt like I had it down. Sarah must of saw that and told me to do it again. I made several confident steps when the plate slipped and fell shattering to the ground. I clasped my mouth in horror. I wanted to cry, I looked at Sarah who had a scolding look on her face. I watched as she walked to the board and placed 8 hash marks under the demerit column and wiped away the 2 hash marks under the merit column. Sarah reached under the desk and came up with a dust pan and a small hand broom. Walking over with a stern face, she handed me the broom and dust pan, then pointed to a trash can by her desk. I kneeled down and brushed all the broken pieces into the pan, then rising up, I walked over to the trash can and dumped the broken plate in. I returned the broom and pan to the bottom of the desk.

"I am sorry Ma'am" I squeaked out to Sarah.

Sarah sighed. "Get another plate from the bottom right hand drawer"

As I returned to the side of Sarah, I noticed a slight amused smile.

"You do realize that when you stopped thinking about it and placed the plate into the trash, you walked perfectly."

I stopped and looked at Sarah. Thinking back to it, I did walk like Sarah when I stopped thinking.

"Wipe that goofy smile off your face and do it again." Sarah brought me back from my thoughts.

Placing the plate on my head, and with a renewed confidence I made the trip down and back 3 more times with out breaking the plate. With a nod of her head, Sarah told me to give her the plate. I carefully took the plate off my head and handed it to her. Telling me to have a seat, she walked back over to her desk and picked up the book she had come in with. She returned to me and handed me the book. I looked at the cover and read it. "Vocal training for the Proper Young Lady"

Sarah prompted me to open the book. I opened to the first lesson and began reading silently.

"Vocal means to read aloud Karri-Ann."

"Sorry Ma'am"

I began reading. "The Sea's on the South Seashore Sing with Delight"

Sarah stopped me, "you will never use your boy voice again. Okay Karri-Ann? Let me hear that sentence again with a higher tone please."

I raised the octave of my voice and started again. Once again Sarah shook her head. I went higher. Sarah gave an approving smile.

"Now just give me a smooth voice, let it out like it was silk"

I began reading again. Sarah coached me on a few more things, but she seemed satisfied. She then had me stand up and do the same thing. By four o'clock she had me walking and reading the book aloud at the same time. Smoothing her dress, Sarah cleared her throat.

"You have had a busy day today, so we will stop early."

She took the book from me and returned to her desk. I dreaded what was coming next.

"Come to my desk and get into your position for discipline"

I willed my legs to move. I haltingly moved to the front of her desk and leaned over and caught myself on her desk. As before, she raised my skirt exposing my sore, swollen ass. Eight whacks later, the tears were coming down my cheeks, though this time I was not sobbing. Again Sarah hugged me close, and then told me

"Karri-Ann, we are doing this for your benefit, we are really starting to fall in love with you, you know that?"

It took me by surprise. They love me? Before I could say something, Sarah told me go ahead to my room. I briskly began heading for the door to my room. Sarah barked out,

"Stop walking fast, you walk slowly to show everyone your sexy walk."

I slowed down, and emphasized my swaying hips as before. I reached the door as it buzzed.

I heard Sarah say "That's a good girl."

I stood in the room for a few moments, regaining my composer. Suddenly I felt the whole day, I was exhausted. I collapsed onto the bed, and within a few breaths I faded out to sleep.

I heard a door close through my dreams. I sat up and rubbed the sleep away from my eyes. Dan stood there with the TV tray of food. He smiled down at me. I smiled and stood up and curtsied toward him. His head went back and roared a laugh. Placing the small table down, he strode over to me and took me into his arms abruptly. His lips smashed into mine with such deep passion that it stunned me. Just as abruptly, he pulled away from me and sighed.

"Not yet, soon though." He smiled again, "there is some reading material for you on the tray for when you're bored. When you're finished with the food, call on the intercom." He pointed to the small box next to the door.

Dan spun on his heel and walked out. I went over to the tray and sat down and began to eat the small portion of food there was. A small dish of rice and a few pieces of chicken breast went down fast. Another glass of milk, but there was no pills this time. Good, I thought, I hate taking pills. A banana was evidently my desert. A magazine was next to the tray. I picked it up and read the cover. Of course, it was a female magazine. I threw it on the ground, pissed. I had to figure out how to get out. There are at least three doors I need to get through, I thought to myself. I will have to bide my time and when I see that third door open a crack I can make a break for it. Maybe in the next few days, I will get out of the second room. I picked up the magazine, in the mean time, I will pretend that I am the best little girl they have ever had. I smirked at this and said in my new voice, "I am a good little girl."

Tossing the magazine on the bed I walked over to the intercom. "Pardon me; I am finished with the dinner."

I wasn't sure if that was what I was supposed to say, but I shrugged and said it anyway. The intercom squelched, and I heard Dan say "Okay sweetie, we will be down in a minute."

I walked into the bathroom and brushed my teeth. There was no mirror, so I couldn't see my face. I walked back into the room, and plopped down on the bed. I starred at the ceiling for awhile. Now, I was bored. Sighing, I reached over and picked up the magazine. It was a woman's fashion magazine. I thumbed through it, looking at the pictures of the glamorous woman, adorned in different dresses, and jewelry. The door opened. I jumped to my feet as Sarah and Dan walked in. Dan grabbed the small table and was out the door again, Sarah held several folded clothes in her hands. "Go ahead and take off the clothes you have on, we will get you into your night outfit."

I removed the clothes I had on, until I was in just the breast strap and my piece of cloth holding down my penis.

"Take off the breast form and your gaff" she answered my question of what it was called.

Reaching behind me I pulled the bow on the gaff, then pulled it loose. Relief came immediately as my penis was free for the first time that day. I then unclasped the breast form. There were marks around where it had bit into my skin forcing the tissue into small breasts.

"Go in and get your enema bottle" I winced as she said this.

I reached under the sink and brought out the enema bottle. I walked back in and lay on the ground. Sarah urged me to continue. I swung my legs up and over my head. With some difficulty I figured out how to get the enema bottle positioned right, I squeezed and felt the fluid squirt inside. I put the bottle down, and tried to relax as Sarah watched. Sarah nodded to me when it was ready and rushed to the toilet. Climbing into the shower I went to work spraying myself out. I heard Sarah filling the bathtub. As if I was in automatic, I stepped out of the shower and into the bath. Hot water stung my swollen ass. Sarah went to work humming that song again as she scrubbed me. In short order she finished and told me to soak for awhile. I heard the door close behind her. The bath did feel good, I started to relax and felt the pains in my body seem to melt away. I heard the door open I realized the water was starting to cool off, I must have dosed off to sleep. Sarah came in and held up a towel. I reached down and unplugged the drain then stepped out into a nice warm towel. Sarah told me to get the large eyedropper and baby oil. I reached down and did the same as before with the enema bottle. I felt the oil tickle its way further into my anus. I wondered what it was supposed to do, maybe make it easier to clean. I shrugged to myself, and helped spread the lotion on to me as Sarah seemed to paint it on. With all that done, Sarah handed me a new gaff. Putting it on, Sarah reached under the gaff and tightened even more and gave that stern look. I learned after a few attempts on how to put the breast strap on. She pulled out a beige looking thing then,

"this is called a body shaper".

She helped me into it. I noticed that it went over my breasts all the way down to my upper thighs. I felt squeezed. It was not as tight as the corset, but it was still tight. Sarah handed me pink panties and a nightgown. Slipping them on, Sarah gave me a once over look. Happy with what she saw she shooed me into bed. I had just gotten into bed when the door opened again and Dan strolled in carrying a mug. Dan smiled and walked over to the bed and handed me the mug. I sat up and took it from him. I glimpsed Sarah scowling at Dan. Dan smiled,

"She has done a wonderful job today honey; let her have the hot chocolate." Sarah sniffed in disgust.

Sarah sighed then looking at me she smiled and nodded. I could smell the chocolate, thick and rich. I normally was not a big fan, but this smelled so good. I tipped it up to my mouth and felt the delightful smell and feel of it as it made its way to my stomach. I finished it too quickly and looked into the bottom of the mug hoping more would magically appear.

"Are you all done? Now go brush your teeth again, hurry it's late as is." Sarah opened the blankets and pushed me to the bathroom.

Halfway there I noticed Dan watching intently and smiling. I scampered faster in the bathroom to brush my teeth. I went back in after I had washed out my mouth and climbed into the bed. Sarah tucked the covers up under my chin, then leaning in she kissed my lips softly.

"Go to sleep sweetie, another big day tomorrow"

She stepped away with Dan taking her place, "Sleep tight little girl." He said with a smile and also leaned down kissing my lips. The world got darker as I fell sleep, it came fast, I didn't even remember them leaving.

Chapter 5

I was woken up by the lights being thrown on the next morning with the same routine as the day before. I was put through the cleaning, the dressing, and a new wig being put on. The day was the same as before also. Morning was dedicated to learning the manners and etiquette of a lady. I had an afternoon of learning posture and learning how to talk correctly. I had fewer demerits, but there was still a spanking. There were fewer tears this time.

A few days later, the regiment changed. I awoke to the lights, and Sarah came in carrying what looked like a tackle box. Placing it on the small corner table, she turned to me.

"Get ready, and when you're done, we will be learning how to put on makeup."

I went through my morning ritual, coming out to find my new clothes for the day. Each day had been a different type of outfit. After the corset had been tightened and tied, I began putting on the dress she had on the bed. Looking down I realized it was straight out of Alice in Wonderland. I put on the white knee high socks and the black shoes. Sarah stepped up to me and put a hair band over my head, sweeping the hair back. Smiling, Sarah guided me to the small corner table. She opened up the box; it was filled with all kinds of makeup. Sarah began naming each kind, then demonstrating on what it was for. The whole morning was dedicated to make up. I put it on, and then took it off; I tried each one until I knew what each piece was and how to use it. Finally I washed my face for the last time.

"Go ahead and put on your final make up for the day." Sarah told me.

I went to work looking at myself in the small make-up mirror. I finished and looked at Sarah. Sarah scrutinized my job, looking at me from every angle. She took out eyeliner and told me to try a little bit more. I went to work again on my eyes. This time Sarah clapped her hands. "You are a natural"

She kissed the side of my head and hugged me. She headed out the door. I began holding the mirror around at different angles to see if I could get a look at my whole get up. I wondered how I looked. Damn it, I thought, I am behaving like a woman again. The door opened again, with Sarah coming in holding a camera.

"Sweetie, get up against the wall for me to get a picture of you, Dan will love seeing this."

I stepped over to the wall and crossed my arms at the wrists in front of me. Sarah began cooing over the pose, highly excited. Sarah took several pictures, and was happily looking at them in the small LCD screen.

"Excuse me Ma'am, may I ask a question?"

Sarah looked at me, and nodded still smiling. "May I see the picture?"

Sarah thought about it. "Just one look Karri-Ann, we want you to look at yourself when you are complete, but you look adorable in that outfit, I think it will be okay this time."

I stepped over and she held up the camera so I could see the last picture taken. What seemed like a little girl smiling was standing in it. A shock swam over me. If I had seen that photograph anytime before today, I would have sworn it was a girl. Sarah quickly took the camera away from my eyesight. A look of concern came over her face.

"Oh dear, I should not have done that."

Dread was racing through every part of me. It must have instantly shown on my face. I lost control of my knees, and I collapsed in a heap on the ground. Tears began flowing down my face as I broke down. I hid my face into my hands, and I sobbed.

I heard Sarah pause, and then she regained herself. "KARRI-ANN!" she roared.

It only made me sob harder. There was another pause; it seemed she was trying to figure out the best tact to apply with. In a softer voice that was suddenly next to my ear.

"Karri-Ann, why are you crying?"

My mind swam, I was crying because the sudden realization that my masculinity had been stripped away from, leaving me stuck in between. I was not a real girl, but in the picture I looked like one, that meant I wasn't a man anymore. I wanted to scream at her, I wanted to yell, what had they done, why they had done this. But I knew also, if I said this, I would be punished severely. I knew I would never get my chance to get out of here. So I knew, I must make up something, it needed to be believable, but it also needed to be something they would not punish me for.

In between sobs, I began saying it. "That can'tbeme!" I stuttered another volley of tears.

Sarah seemed to catch what I was saying, and she took it as I exactly had wanted her to take it. I felt Sarah gather me up in her arms; I latched onto her and cried. Sarah pried me off of her, and holding my face between her hands she looked me in the eyes.

"Karri-Ann, that was you, you are becoming a very beautiful girl. Soon you are going to be a beautiful woman, the type of woman that every man will want to be with. You will no longer be unappealing to anyone; you will be the want of everyone."

She had bought it. She had thought I was saying that I had been ugly before, unwanted, and that now I looked pretty, and I didn't believe that it was really me. Sarah did something that I did not expect. She leaned forward and we became locked in a passionate kiss. Her hand slid around behind my head and gripped me tighter to her. I felt something stir. The gaff became tight, there was pressure building up. I felt reality slip; I reached around Sarah wrapping her in my arms. Sarah pushed me away, and stood up. Reaching down she took me by the hand and helped me up. She guided me over to the bed. She reached behind her and I saw her tight dress come loose as she unzipped. Her eyes were locked with mine. Her dress fell to the ground in a pile around her feet. She had not been wearing a bra, her breast stood out at me. I reached over and lightly drew my finger around the curve of each breast. She inhaled deeply and drew into me with a hot kiss. I felt her smooth skin between my hands; my press on nails lightly caressed her back. She pushed me back onto the bed, pulling off her pantyhose; she crawled on top of me. I began stroking her ass while she tried to inhale my tongue. The gaff was restricting me, I wanted it off. I started to reach for it, but Sarah stopped my hand. Sarah sat up, then crawling up me; she positioned her hips over my face. I was staring at her clit. I reached up, with both my thumbs and I spread her apart then I began lightly licking her wet gash.