My Best Friend's Sis Ch. 03

*****Content Warning: This story contains elements of truly nonconsentual femdom activities. If that's not your cup o' tea kindly read something else*****

It was getting late in the main room. I had just taken my fourth shower of the day after my third time being taken from behind by Emma. I lay engulfed by the pile of dainty clothes that lined the floor of my new home. And sleep was just not coming. My racing thoughts swerved back and forth between arousal and logic. Between the feeling of Emma's cum filling me up inside and the looming change that awaited me if I couldn't conjure up a plan to escape this seemingly impenetrable prison. The cage around my cock seemed a microcosm of my whole life. The metaphor extended perfectly as my frustrated member pushed helplessly against its confinement.

I had three days. Three days until Nellie's thoroughly paid off "medical technician" would be paying us a visit to permanently alter my body in one way or another. I had no clue exactly what Nellie's threat was implying. I only knew she had mentioned that her plan would shock even the seedy surgeon she had somehow convinced to break his hippocratic oath. I could only imagine such a person wouldn't be so easily surprised and it was driving me crazy. In the best and worst of ways. Why did I have to be so turned on by something so completely wrong?

Over the course of three well earned showers Emma had laid out all of the details of Nellie's schedule as well as the layout of our underground dungeon. The only rooms I had yet to enter at this point were the kitchen and the operation room. The kitchen was only available to Emma, who had gained significant trust from Nellie during her six month stay here. It had meager condiments and spices that could be added as we liked to the meals Nellie sent down to us twice a day. It also had a sink that Emma could use to wash the dishes and even a microwave oven.

The operation room was the most complex room by far. It contained a hallway to the elevator that Nellie used to go up and down. It also had the electrical box and circuit breakers, plus tons of medical hardware necessary for the plastic surgery operations Nellie forced her slaves to undergo. It was the only room that Emma couldn't access if she wanted to. The only reason any of us would see it is if we were about to be operated on.

I couldn't sleep for most of the night. In my mind I went over scenario after scenario. None of them looked very good. Nellie had really created an extremely secure environment to keep us in. She was a cold hearted bitch, but she was damn smart. I imagine it was about 5am before I drifted off to sleep.

A hand caressed my ass cheek. I clenched my eyes shut and clung harder to the mound of clothing beneath me. It was too early for this. At the same time I instinctively wagged my sensitive butt back and forth in lust. I already knew it was Emma behind me. Nellie had school all day today. It was Monday. That meant she would be away at extracurriculars most of the evening as well.

"Miss Nellie says it's time to get up, sweety," Emma's voice whispered softly.

She patted my ass a couple times. I opened my eyes reluctantly and looked over my shoulder. Emma was naked. And she was rock hard.

"Miss Nellie also says I'm supposed to get your day started right. And honestly, I'm inclined to agree."

I nodded and presented my ass to the angel of a t-girl. She needed no further coaxing. Immediately she pressed against my hole with her lubed girlcock. I couldn't help but moan.

"Oh, you like that cock against your little pussy?"

"Yes, Miss Emma."

"Well then you're gonna love this."

Emma immediately entered me. Slowly, sensually she went most of the way inside before pulling out.

"Was I right? Did you just love that?"

"Yes, Miss Emma. I loved that."

"Tell me you little bitch. What exactly did you love?"

I started to wonder if this was all for show to appease Nellie or if she was actually getting off on demeaning me. I know I was getting off on it plenty. And I'm sure she could tell.

"I love getting filled with your giant cock Miss Emma. Please enter me again and again."

"Well, okay. I guess I could help you out. If your really love it that much."

Emma thrust inside me again and spanked me twice. Then she pulled slowly out and shoved her cock back in! Her hips pushed against me. They felt so nice on my ass as they squished against me. I looked back to take her in. Emma really was quite curvy. And her gorgeous body was pressed up against me, except for that one less than feminine part that filled me up.

She got to work fucking me in and out. After a few more thrusts Emma reached around and cupped my chest.

"My my, these really are some tiny titties," she whispered faintly into my ear. "I almost think we should let Nellie give you some bigger ones before we get out of here. Those things cost a fortune."

I moaned at that thought. I didn't dare give any answer because it would surely give us away.

"You like how I can whisper whatever I want and you can't answer me?"

I moaned again in response.

"I'm just gonna start assuming you agree with me."

I moaned again. Emma really knew how to push my buttons. I could tell she was enjoying herself but I also could feel the tenderness with which she fucked me. Nice and slow, savoring each moment and sensually whispering to me. I felt her start to pulse inside me and then I felt her spray me full of her hot cum. She stopped and remained inside me until she was empty.

"Let's hit the showers bitch."

Emma led me by the cage toward the showers. When we got into the makeup room she gave me my daily dose of hormones and stripped my sexy nighty off of me. Moments later the hot water cascaded over us as we embraced in the shower. Her tits rubbed against my chest, causing my cock to push on the cage harder than it already was. My dick felt like a popcorn kernel ready to burst in the microwave but I had to attend to business while I could.

I strained to hold back the many questions I had for Emma. I really wanted to know if everything was just a show for Nellie or if she really enjoyed dominating me like that. I knew her tenderness was real. But given what I knew about myself now I really hoped she had that bossy side I had come to love. Silly me, I was already thinking about the future. But now I had to help it take shape.

"I think I have an idea. It's risky though."

"I don't like risky. Think about what Nellie would do to us if we failed."

"I know, me neither. But we're running out of choices. Plus, it won't be long until she gets bored and then she'll be just as bad anyway."

"You may be right. Okay, well what have you got?"

"It's too late for now. We'll have to talk again later."

"You're right. Well, I can think of some reasons to take another shower very soon."

She dropped the soap.

_______________________________________________________________

Three more showers later we had laid the basic groundwork of a plan. Our short window each time made it hard to get much done. We had one more day tomorrow to iron out the details. Then it was showtime. Nellie didn't even come down that night when she got home. She came on over the screens and told us she had been watching us all day and it looked like I was really learning how to take a dick. Then she said "Goodnight, sluts."

The next morning Emma woke me very similarly to Monday. There really wasn't much to do down here but fuck, especially when Nellie was off at school for most of the day. Plus, every time we did it earned us a shower to discuss our plan. We made significant progress. It was agreed that the plan was obscenely risky and likely to get us both killed. But as you can imagine we were absolutely desperate to salvage what we could of our own lives before we became any more permanently changed than we already were.

After a discussion in the shower we stepped out and did each other's makeup. I was painting Emma's second eye with liner when something happened. As I looked closely at her eye I thought about how she hadn't been able to avoid some serious alteration to her body during her six month stay. I realized it was unlikely that she had developed all of these changes just due to hormones and it became clear to me. Emma had met the surgeon before. That's how she knew about the operating room.

I looked sadly down at her pretty face and she began to tear up. We stared deeply into each other and cried. I brought my forehead up against hers, and then my lips. We kissed sweetly, mixing lipsticks in a sudden explosion of passion. My sorrow for her melted into affection.

"Hey, we just took a shower. Shouldn't we at least get dressed before we make a mess of ourselves again?"

I had interrupted but the kissing continued between words.

"I think you're forgetting who's in charge here little girl. Do you want me to tell Miss Nellie that you're turning down my advances?"

More kisses, more sloppy noises.

"No, Miss Emma."

Emma grabbed my ass and squeezed. Then she gave me a light spank.

"Good. Besides, I know you want it. Don't play coy with me you sneaky slut."

Then she pushed me back and guided me down onto the floor. Right outside the shower she fucked my brains out again. Lustfully she filled my puckered hole until it was gaping and accepting every inch. When she finished she held me tight, still inside me.

______________________________________________________________

That evening Miss Nellie appeared from the operation room door. She looked tired, with bags under her eyes and a droop to her posture. She donned the stereotypical dominatrix garb, a sexy black leather corset dress. Her breasts jutted out the top and bounced seductively as she approached Emma and I. Looking like that, I might have obeyed her even if I weren't her prisoner.

"Good evening, sluts. How are we doing?"

"Good, Miss Nellie," we answered in unison.

"I'm glad to hear. Are you excited for your big day tomorrow, Sammi?"

It was terrifying to even think of what she had planned for me but I managed to choke the words out.

"Yes, Miss Nellie. I'm very excited."

"Oh me too, Sammi. I think you're going to be so perfect and pretty when we're done!"

I stared at the floor in an attempt not to betray my true thoughts.

"You know, my little whore, you're going to need some recovery time after tomorrow. And I was just thinking how much I'm going to miss making you my bitch for a whole month. So I was thinking, why don't I get a month's worth of use out of you tonight to make up for it?"

"Yes, Miss Nellie. I think that's a great idea."

"Good. Now Emma, I want you to take Sammi here over to the fun room and get her secured to the bench. I'll be there in one minute."

"Yes, Miss Nellie."

We walked down the hall from the main room to the play room. As we passed each door, I went over the next day's plan in my head. Kitchen, operating room. We each had our parts to play. I didn't know which was most likely to go wrong. It was going to take a lot of luck.

Nellie strapped me down to the bench, ass up. She lovingly rubbed my butt cheeks and my back while we waited. It didn't take long. High-heeled footsteps approached, and I looked over my shoulder to see Miss Nellie enter with a strapon.

"Emma darling, why don't you go back to your cell like a good girl. I need some time alone with little Sammi."

"Yes, Miss Nellie."

Emma departed, leaving me alone with our divine monstress. The vile woman, sexy as can be, began to circle me slowly.

"I've been working so hard this week to make sure everything works out perfectly tomorrow. Just getting together all of the details and making sure my family doesn't suspect anything when my friend comes over. On top of school and my regular extracurriculars it has me exhausted. So you'd better be glad I'm doing so much for you."

She didn't know it but her description confirmed a crucial detail of my plan. Her family would be home.

"Thank you for all of your hard work, Miss Nellie!"

"Hmm, I'm not completely convinced this time. You'll have to really show me how grateful you are in a minute. For now, I have a couple questions for you."

"Yes, Miss Nellie."

"Do you have any allergies?"

"Yes, Miss Nellie. I'm allergic to penicillin."

"Ooh, that's important to know. Okay, here's a more fun one. How big should I make your tits, hmmm?"

She forcefully pinched my nipple and shook it back and forth as she asked.

"Umm, hopefully not too big Miss Nellie!" I blurted. I regretted it immediately as the air became heavy around me.

"Wrong answer, cunt. The correct answer is whatever size pleases me most. So, how about we go with some double D's?"

"If that's what you want, Miss Nellie. It sounds perfect."

"Hmmm, but maybe we should go for the F cups?"

She kept fondling my chest as if I were already so endowed. I squeaked from the sensitivity.

"Will that be big enough for you, honey? Do you want F cup titties tomorrow?"

"If you think so Miss Nellie, I think that would be perfect."

I bit my tongue to keep from backing out.

"Ah, much better. But then again, I wouldn't want you to have back problems would I?"

"No, Miss Nellie."

"Wrong answer again slut. The answer is maybe if it pleases me. And I think it does. I think it would please me very much. So here's what's going to happen honey. Tomorrow when you wake up from the surgery you're going to have H cup breasts. You're barely going to be able to lug them around, skinny thing that you are. But it's going to be very entertaining for me. I can just see it now, your giant tits bouncing up and down as I fuck your little ass, slapping against your skin again and again. Why, they might even knock the wind out of you."

"Yes Miss Nellie, as you wish."

"Good. I can't wait. Now, what else do you think we should do with you, cutie?"

She grabbed my balls in her hand and kneaded them between her fingers.

"These are getting pretty full, sissy girl. Maybe if you have to carry around those huge boobs we should make up for it and lighten your load a little bit. What do you think, should I take your balls?"

I gasped at the suggestion. For a moment I actually felt a defensive twitch in my loins and grunted at the sensation.

"Answer me bitch!"

She slapped my balls lightly, causing a dull ache to linger in them.

"Um...I...if it pleases you Miss Nellie."

"Hmmmmmm, it just might. Maybe it depends on how good your ass is tonight. You know, if I'm not satisfied we may just have to give you a pussy. That way you can take it in three holes at once! And I can have my choice. Would you like that?"

I was still shaking from the fear.

"I...I..uh..would like that if you like it Miss Nellie."

"Good girl. Well, you'd better give me the best ass of your life right now if you want to keep your precious girl-cock and your little slut-balls. But first, let's see how that gag reflex is doing."

Nel quickly made her way around and rudely shoved her huge strapon down my throat. I choked right away. It can take a lot longer than this to get rid of a gag reflex it turns out.

"Unacceptable, whore. You really are a slow learner aren't you. You're body is trying to reject me when your soul wants my cock as far inside you as it can get. Let's try to get you in tune, yeah?"

She shoved it in again and again. And each time I gagged, trying my best to accept her dildo in my throat but failing over and over. She went at this for far too long, but it was clear with each passing moment it just seemed to amuse her more. My mascara ran in streams down my tearful face.

"Ah look at you. Now you're such an ugly little whore. It's a shame your makeup isn't permanent. You know, we could always fix that tomorrow."

My eyes grew wide again and I almost froze up. I was distracted by my cock trying so hard to escape its cage mixed with the fear that I would never be able to pass as a man again. I almost forgot to answer.

"Yes, Miss Nellie. If it pleases you."

"Oh it will. And let me tell you honey. This is just the beginning. When Sal is finished with you tomorrow you're gonna be a brand new woman."

"Thank you Miss Nellie."

"You're welcome, now let's see about earning your balls. Put that ass up for me."

I did as she asked, shaking my ass back and forth seductively, desperately as she walked around to get in position. As she reached her spot behind me she put a hand on each ass cheek and spread them apart. I heard a spitting noise and then felt her warm saliva running down my crack. She slapped both cheeks twice quickly causing a gushing noise with the trapped spit. Then she spread them out and did it again.

She teased me, running a finger down the crack and barely touching the hole. I had learned by now that she wanted me to beg her. And besides, this was my chance to make a good impression before she made a final decision about tomorrow!

"Pleeease, Miss Nellie! I need you to bury your cock deep inside me! I'm so fuckin' hungry for your cock!"

I kept wiggling my ass and trying to back into her like a hungry slut. I did everything I could to demean myself for her amusement. My balls were on the line!

"Oh, you mean this cock?"

Nellie rubbed it against my hole gently.

"Yes, Miss Nellie! That is the cock I want!"

"I don't know, you seem to be quite enjoying Emma's cock recently. Are you sure that's not the cock you want inside you?"

I had to lie with all that was within me.

"No Miss Nellie! Your cock is the best I've ever had and I don't want any cock more! Please fill me up to your heart's content."

"Hmm, very convincing this time. You may just get to keep your balls after all. Let's find out.

And with that she started to give me the most brutal ass pounding I had experienced yet. She didn't enter slowly or wait for me to warm up. Just pushed her way in, stretching me and making me squeal with pain. The worst part is I couldn't even resist. I had to back up on her as hard as she was fucking me. And I had to disguise my moans to make them sound like pleasure.

"That's a good pussy you have here! Are you sure you don't want another?"

I could utter no response but it seemed rhetorical anyway. She grabbed my balls again.

"It would be a shame if I couldn't grab these anymore when I want control. But sometimes sacrifices must be made."

I continued to swallow her dick with my asshole as hungrily as possible. It finally started to turn into a pleasurable feeling after I had endured the initial discomfort. I started to moan with quite genuine pleasure now. She seemed to notice.

"Ohhh that's it you little slut! You love my cock! Take every inch!"

Nellie plunged in hard and ground her hips against my butt. I kept pushing back against her even though she was really at the limit of the depth I could take. "Please let this be worth it," I thought. Then I realized that no matter what she decided, my plan was to escape before she could do anything to me anyway. I clung onto that thought as she took her frustration out on me, smacking me and fucking me raw.

After fifteen minutes of pounding, a short eternity, I started to feel something stirring in my balls. I let out a loud, whimpering moan. Nellie knew exactly what was happening.

"Oh my god! You love my cock!" She was beside herself, almost laughing.

"Yes you little sissy slut! Cum like a whore from taking my cock. MMMMMYes!!"

And so I did. I had a powerful, shaking sissygasm in my cage and tried to collapse afterwards but there was nowhere to go. I was strapped down, my ass was still up, and Nellie was far from finished.

"Oh baby now I'm gonna get mine! You'd better believe it! Back that ass up!!"

It was another half hour before she had her final climax from fucking me and eventually pulled out, removing the strapon.