My Best Friend's Sis Ch. 02

I awoke with a jolt! Miss Nellie was standing over me with the riding crop she had just hit me with.

"Good morning, Miss Sammi Sweet. How are you feeling today?"

"Um, not so great Miss Nellie! That fucking hurt!"

Miss Nellie laughed and hit me again. This time on the other ass cheek.

"You should learn to be grateful for the pain I give you. It makes me happy. And when I'm happy, your happiness is sure to follow."

I contemplated trying to argue the logic of that but I knew it was no use. This girl had a fucked up labyrinth in her mind. Whatever I said would just get turned around.

"You're right, Miss Nellie. Thank you for your brutal assault."

I couldn't resist a little hint of brattiness and let me tell you it did not go over well. *Thwack* She hit me harder.

"You're welcome, you little whore. Now open up and stick out your tongue, it's time for your morning dose."

She procured a small pill just like yesterday's and placed it on my tongue. Then she poured some water in to wash it down.

"Mmmm, you like the taste of womanhood don't you?"

"Yes, Miss Nellie. Thank you sooo much."

There was still a hint of sarcasm that I couldn't filter out and it led to another swat. And another. Miss Nellie hit me a total of five more times actually. I began to cry.

"Awww, you're crying like a little girl. I'm not surprised I guess. I have some errands to run. I think I'll leave you here for a little while. Be good!"

My tormentor began to walk away, swaying in her thin white pajama shorts. She stopped just short of the door, looked back, and raised an eyebrow. Then she grabbed a large butt plug from the wall and came back over.

"But before I go, I think it's time we move you up a size. After all, it's been a whole day and you've proven yourself to be such an easy slut."

Miss Nellie applied some lube to the end of the plug and pressed it against my exposed hole. She did little circles with it and my nerve endings tensed. I shuddered in anticipation and fear. What surprised me the most was how badly I wanted it inside me. And Miss Nellie could tell as she looked at my face.

"Anxious girl, be patient. Jeez, if I just shove it in it's going to hurt! I wouldn't hurt you, would I?" She laughed and pushed the plug in mercilessly.

I yelped but appreciated the sensation of being full as the pain died down. Then Miss Nellie left the room with the same sway as before, teasing me with her perfect body as she disappeared.

I had been stuck in my bondage for another half hour, contemplating my predicament and sobbing a little when suddenly I started to feel a pleasurable feeling deep in my pelvis. The butt plug had stimulated me just enough and I began unconsciously gyrating my hips back and forth. It felt so good to be filled up so full and to have the toy rubbing against my prostate. I moaned aloud and then gasped as Emma came in the room.

"Wow, you like that little toy don't you?" She giggled.

"Um, I guess so," I answered bashfully.

My words were not quite as naturally scathing when directed toward Emma. I knew she had as little choice in being here as I did. And she looked so cute today! Jeez, what was I thinking? "Stop! She has a dick!" I screamed in my head. Then I looked up at her smiling face. No wonder I was confused.

"Well, I would give you a little something more in there if I wasn't stuck in my little cage." She winked.

I didn't know what to say (still uneasy with the thought of how nice that sounded) so I remained silent.

"Oh, don't worry. You'll learn to love my dick in you. This is only your second day here. Until then I've been instructed to take you to the makeup room and get you looking all pretty! Won't that be fun?"

I groaned and nodded as she began to untie my limbs. It was good to be freed, especially for my aching joints which had been strained all night. I was instructed to leave the plug in and take my clothes off. I did as I was asked as I followed her out of the "fun room", waddling.

Down the hall we came to a door I hadn't entered yet, the makeup room. It had a shower in the corner and Emma told me to enter. The water had already been warmed up and as I stepped in I felt such relief. Emma came in behind me and picked up a bar of soap. She rubbed it between her hands and then placed her slippery palm on my chest.

She used her thumb to circle my nipples one at a time before rubbing the soap under my armpits and embraced me in a hug. She whispered in my ear.

"This is the only place I suspect she can't hear us. I'm so, so sorry I had to force you to suck my dick. You have to understand, if we don't comply that bitch does horrible things to us. I want us to be on good terms, cause the four of us are all each other have got."

I looked at her face, shocked. Of course she wasn't as bubbly and excited as she appeared in front of Miss Nellie. It was all a mask she had to wear in order to survive. The Emma I knew was just an actor in some fucked up play. I saw a tear come to her eyes and wiped it away.

"It's okay, Emma. I've seen what she can do. There has to be some way to get out of this!"

Emma looked less than hopeful.

"I've been working on it for six months. You let me know if you come up with anything, but we have to cut this short now. The cameras can still see us from one angle."

She pulled away with a wink and dropped the soap.

"Oops!" she exclaimed. "Will you pick that up for me darling?"

I started reaching down to get it.

"Ah ah ah, bend at the waist. And take your time."

I did as she asked and she ground her hips against me from behind, wiggling the plug inside me. It felt amazing. I began to grind back against her.

"Ooh, you love that my little soap bitch. Well I don't have all day, get back up here!"

Everything she said was exaggerated, as if she were trying to make sure the microphones could hear. I began to wonder if she actually enjoyed grinding up against me as much as I enjoyed it. Or was it all an act to save her from Nellie's punishments? I could only imagine how exact the training got after that long. I was on my second day and Miss Nellie was already policing the tone of my voice.

I complied and came back up, handing her the soap. She washed the rest of my body. The cute T-girl took extra time scrubbing my sensitive areas. I was left clean and incredibly turned on.

After the shower, Emma led me over to a chair in the other corner of the room. It was complete with a pink-bordered mirror, carved with intricate floral designs. As I looked at my reflection I could see her in the back getting things ready. Emma spun me around and began to apply lipstick first.

"Red is perfect for you. So bold, and so slutty. Hmm, what shall we do for those gorgeous eyes?"

I saw her reach for a dark brown eye shadow and rub it on. Then she brought out a liquid eye liner brush. The cold sensation ran across my eye lids one at a time. It tickled slightly as she did a perfect wing tip on each side. Then she went to work on my cheeks.

Now, I'm no expert on this stuff. I've heard the word contouring thrown around a lot. And blush, highlighter, whatever. All I know is when she finished she had effectively made me look sufficiently womanly. The girl spun me around to see.

"Oh my God, look at you Sammi! You're gorgeous!"

I blushed.

"Thanks, Emma. It was all you."

"Aww, how sweet. You guys are having a moment," Miss Nellie interrupted. "I'm glad you girls are getting along. It's so sweet to see you play nicely. Now get on your knees, both of you sluts."

And just like that, we were dropped back into the hell that was serving this foul monster of a woman. She was donning a strap-on and cock-slapped us each in the face a couple times. Then she made us stick out our tongues and she patted our tongues with the fake cock, making wet slapping noises.

"I think you two cocksuckers might enjoy a new toy I've got. Wait here."

Miss Nellie was gone for just a second and then came back with a short double sided dildo with straps hanging off the middle. You can guess what she wanted us to do with it. We were placed face to face, still on our knees. Miss Nellie shoved the two sides of the dildo slowly but firmly through two pairs of painted lips. Which met in the middle, mine on Emma's. I was not completely unhappy with that aspect but as Miss Nellie tightened the straps I began to gag a little bit.

"Aww, see Emma? Little Samantha still has to work on her gag reflex. Yours has been gone a long time, hasn't it?"

Emma tried to answer with a muffled moan as she nodded yes. Her lips slid across mine immaculately. I didn't know how long I could go without actually throwing up though. I started panicking and trying to scream through my gagged mouth. Nellie pushed our heads together extra hard and then gave me relief.

"Samantha! You have to get used to choking! Got it? This is your life now."

She placed the dildo back in my mouth and tightened the strap extra tight. I started to gag all over again. I tried to last as long as I could with tears streaming down my face. But then I started to panic again. I really didn't want to throw up in Emma's mouth! Miss Nellie undid the strap again.

"Well, if you can't pull your weight around here Emma is gonna have to pick up the slack. Isn't that right, Emma?"

"Yes ma'am. I can take extra for Samantha. Thank you for the opportunity."

"That's a good girl," she said condescendingly.

She then adjusted the dildo so it was longer on one end. This left me with a more manageable amount of cock to take in my mouth. And unfortunately left Emma with more than I could imagine being able to handle. But she took it like a champ. All the way into her throat. The straps were tightened once again. Then our Mistress spoke again.

"Alright, now you two love birds are going to keep exchanging lipsticks while I give you a little spanking. Sound good?"

We both made unintelligible moans in response.

"Good. Now, Sammi. Because you can't take as much cock in your mouth you can have some of Emma's spanks. Sound fair?"

"Hardly," I thought to myself. But I released another affirmative moan as she began to redden my ass. I cried out into Emma's mouth. My reactive jerk away from the spanking shoved the dildo further into her throat and I felt really bad. I resolved to take the rest of the spanks like a man. Or...something like that.

After I was beaten to tears and my backside was surely as red as a firetruck Miss Nellie switched to spanking Emma. As promised, she didn't go as hard on Emma and then returned to me. It felt like she must have spanked us a total of ten minutes straight before she was done. Then without warning she pulled the plug out of my butt. I gasped, taking in some of Emma's sweet breath.

The plug was replaced by two fingers that felt around inside me. It felt immaculate. Miss Nellie was massaging my prostate. I moaned into Emma's mouth again. Her lips moved against mine as much as she could. I could tell it was her way of affectionately comforting me. At this moment between Nellie's fingers and Emma's lips I thought to myself, "I could get used to this." It kind of scared me, but I was at least starting to accept my attraction for Emma. She really was a sweet person. And in almost every way she was a woman now.

Miss Nellie reached around and felt my extremely stiff cock. She started to stroke it with one hand as she whispered in my ear.

"Oh you are really enjoying this aren't you? Do you have the hots for Emma?"

My cock jumped at the humiliation I felt when she said it out loud.

"Oh my, you really do have the hots for Emma. Maybe I'll let you suck her cock again. Ooh, or maybe I'll let her suck yours. What do you think."

I couldn't provide a real answer of course. I was still dildo gagged and lip to lip with Emma. I just moaned with the arousal brought on by her questioning. Maybe she was right about my true nature after all.

Miss Nellie stopped and left me empty. Then she unstrapped the double-sided dildo gag.

"Good job girls, you got me really wet! Emma, why don't you go with Samantha and pick her a nice outfit for today. With the way her makeup looks, I'm thinking less tasteful and more slutty. Kapeesh?"

"Yes Miss Nellie. I'll make her really flashy and over the top."

Emma led me by the hand to the main room as Miss Nellie went the other way toward the play room. She made quick work of an outfit choice. I guess she had been practicing for about six months straight every day. She chose all red underwear. A thong and a frilly bra with foam inserts. Deep red stockings and a garter belt which she attached with skill. Then she threw on a black jean mini-skirt and a red and black top which barely covered the bra, but made the tits enclosed within look pretty real.

When she was finished we went to the play room and met up with Miss Nellie. She smiled wide when she saw how sluttily I was dressed.

"Well done Emma! For that, I think you get to be the one who get's sucked. Besides, we need to put more work into Sammi's gag reflex. Isn't that right Samantha?"

"Yes ma'am. Thank you for the opportunity of practicing my deep throat skills."

"Oh you're very welcome. And wow, you're learning to control that tone, young lady. Very good. I'm gonna reward you with a nice big dildo in your ass."

And just like yesterday she unlocked Emma from chastity and I sucked off the cute T-girl while Miss Nellie fucked my ass with the strapon. Only this time I wasn't restrained and it was all doggy style. As the two gorgeous ladies spit-roasted me I moaned and choked and sweated. My asshole had already been warmed up all day so Miss Nellie didn't hesitate to pick up the pace.

She was pounding the shit out of me and I was making little squeaks with the rhythm she was setting. Emma followed suit and pushed at the same speed from the front. This effectively squeezed me between cocks and I was getting turned on like a mother fucker. Miss Nellie reached around and stroked my cock, bringing an orgasm and loads of cum almost right away. She collected it all in her hand.

Here Emma, why don't you snowball your little slut sister here with her cum. I didn't know what that meant, but it didn't sound good. Emma then licked and slurped all of my cum off of Nellie's hand with all the cum. And then she began to slurp and lap at my lips like she had Nellie's hand. It was so hot, and Miss Nellie obviously enjoyed her overzealous show of sloppiness. I kept in mind that I might have to do that to please Miss Nellie sometime.

"Emma, did you not get to cum?"

"No ma'am, I'm still full over here."

"Awww, poor thing. Well, that was your chance. Maybe you'll get another tomorrow. Maybe not."

She brutally slapped Emma's cock until it shrunk down to size and then locked it back up. It was hard to watch.

"And you," She gestured toward me. "You got lucky this time. But you're going to have to learn to control yourself or you'll get chastity too. Now I've got to go see my family. Why don't you girls go and get washed up again. This time, Emma, you are to supervise Samantha while she does her own makeup. Let's go with preppy, cute, and minimal."

"Yes ma'am," we responded in unison.

We went back to the makeup room and took off each other's clothes, just as we figured Miss Nellie would want. Yeah, that must be why. When we entered the shower Emma held me close again and whispered.

"Okay, I'm starting to think you actually do like sucking my dick. Is that true?"

"Yeah," I whispered back bashfully.

"Good to know. At least I can let myself enjoy it now too. You're pretty cute when you're all made up you know."

"Thanks. Hey, I know we're short on time. But I've been thinking of how we can get out of here. What do you know about the bitch's schedule?"

"A lot. But this is all the time we should spend for now. I don't want her getting suspicious. Looking forward to hearing any bright ideas next time though. Don't worry, it won't be long. Nellie likes to make us shower often. She wants us clean."

Then she dropped the soap again and exclaimed, "Pick it up bitch!"

I did as she asked and she grabbed my hips, gyrating against me from behind. I was hard as a rock again almost immediately.

After we finished our shower Emma coached me through the makeup process. We did a minimal amount just like Nellie wanted. Then we went and she helped me pick out a school girl outfit. You know, plaid miniskirt and high socks. Classic cute preppy stuff. And she put my hair into pigtails.

"There, Miss Nellie should be very pleased with that!"

"I should be pleased with what?" Nellie questioned.

She had a habit of suddenly showing up at the funniest times.

"Oh...I see. You look so cuute Sammi! Turn around for me so I can see your butt."

I did as she asked. She walked over and lifted up the back of my skirt with her riding crop. And then caressed my butt with it. The worst part about Nellie was never knowing if she was going to be sweet or cruel. I braced myself for a possible swat.

"Alright, I have an announcement to make girls. It's going to be good news for one of you and bad news for the other!"

Emma and I looked at each other, then back at Nellie inquisitively.

"Emma, your chastity is over. Not only am I going to let you cum. I'm going to let you cum every day now. And your chastity device will be put to use getting Sammi under control."

"Thank you so much Miss Nellie! Thank you thank you!"

He glee was not feigned. I could only imagine being in chastity all the time. But it looked like I was about to learn what it was like.

"You're welcome, Emma. You've earned it with your faithful obedience. There is one catch though. You can only cum inside of Sammi. Not in your cell. And not any other time. But any time you're out and you'd like to. You can take Sammi from either end. She has to learn about taking cock. And it's going to start right now. Sammi, why don't you grab your ankles?"

I did as I was told. In front of me, Nellie released Emma from her chastity device. Her cock grew to its full, intimidating size.

"Now Emma, move behind Sammi. Good. Now put your cock right at her entrance. Very good girl. I want you to keep it right there. I'll be right back."

I was dying of arousal with Emma's cock right on my hole. My nerve endings were firing like the fourth of July in Las Vegas. I could feel Emma wiggling back and forth, causing little clenching spasms in my rosebud.

"It's time to meet a new friend, Sammi. This is Krysta. She's going to help you with that gag reflex. Aren't you Krysta."

"Yes, Miss Nellie," the other T-girl answered shyly.

Her voice broke my heart. It sounded like she was not nearly as resilient as Emma. Who knows how long she had been imprisoned down here, but hers was the voice of a truly broken person.

As she moved in front of me, already freed of her chastity, I saw just how terrified she was. No wonder Miss Nellie didn't bring her out as often. She was downright pitiful.

Regardless, she obediently brought her cock to my lips. It was smaller than Emma's. It would be easier for me to take. I waited with a cock at both entrances. The first time I had a real one about to enter me from behind. I shuddered.

"Are you ready, Sammi?" Miss Nellie asked teasingly.

"Yes, Miss Nellie."

"Hmm, beg for it. And it had better be convincing."

"Ohh Miss Nellie, please please let the girls fill me from both ends. I need their cocks to fill me up so full!"

"I'm not sure you really want it."

"Pleeease Miss Nellie. Please give the order so I can have what I neeed inside me!"

I had actually screamed. I hoped the girls couldn't tell but it was a least halfway genuine. I was so sick of the anticipation. Until yesterday I had never allowed myself to imagine being near another cock, but now I really couldn't stand the thought of being stuck in this limbo any longer.