My Best Friend's Sis

When the fourth photo was taken I sat on a chair and waited hopefully. After about thirty seconds the room turned red. I heaved a sigh and went back out to the main room. The screen placed the new snapshots randomly in the ever growing film reel of my humiliation and I saw just how silly I had looked.

Obviously she wanted to humiliate me, and maybe that was what this challenge was all about. Maybe she wanted me to put on the sluttiest outfit imaginable so she could deem it "perfect" for me. The longer I took to give in the better for her, right? So I looked around the room.

The next thing the camera room saw was me, dressed in a slutty french maid's uniform. It had taken some time, but I figured out how to get the garter belt attached to the stockings. These white, frilly stockings led into my four inch black high heels. I posed for the camera, bending over for the mid height one to see. Sucking my finger for the eye level camera. Squatting with spread legs over the floor camera and smiling deviously up at the ceiling. Then I waited with fingers and toes crossed. The light turned red.

This game went on for two more hours. I tried on dozens of outfits, each ending with a disappointing red light. I tried less clothes, more clothes, strange clothes, and preppy clothes. Poses were getting harder to think up, so I began reusing different ones. I did everything I could imagine to try and please Miss Nellie's sick desires. After what seemed like a lifetime I had an epiphany.

Miss Nellie wasn't just trying to change how I looked. She was trying to change the way I thought. She wanted me to let out my femininity. So I decided to try and think like a girl. How did women choose what to wear anyway? I looked myself over in the mirror. What assets did I have? A flat chest, but a bubble butt. My face was not overtly masculine but as I looked I wouldn't pass as a woman. I had long legs. Green eyes.

I had always thought I looked good in brown. I selected a denim miniskirt to go with my brown halter top. Matching light brown lingerie as my underwear. And a pair of brown heels. I slightly covered my face with an earthy green tribly hat. Dare I say it, I looked cute. I confidently strode into the camera room and popped my knee out girlishly. I picked all of my favorite poses and was rewarded with a yellow light. I was close.

I took a new look at my outfit and it didn't take long to realize what was wrong. The heels just didn't match the style. I reverted to the fashionable sandals that I had begun with and went back. The room flashed green. Then I went back to eat my late lunch in the main room. The girls all hooted and whistled at me as I entered. The screen now displayed only a scrolling combination of poses in my my final, "perfect" outfit.

"I'm so proud of you Sammi! This was a great start. I think you're starting to think like a girl already! I can't say I'm surprised how easy it was to break you."

"Thank you Miss Nellie. I'm glad you like my outfit choice."

"You're welcome sweety. Why don't we get you a reward? Would you like some desert?"

"Yes Miss Nellie, that would be awesome!"

My hopes rose, but I was confused by what happened next. I heard orgasm noises coming through the intercom. The screen showed Miss Nellie pleasuring herself with a vibrator and looking at a video of me sucking the dildo. She went at it dramatically, screaming with pleasure as she thought of everything she had made me do so far. And probably thinking of what she was gonna make me do next. When she reached her intense climax she creamed. Then she collected it and placed it in a small glass jar. I saw her go to her closet.

"The frosting for your desert is on its way down sweety. It's gonna go great with a taste of Emma's feet. Now play nice with her, you know I have total control over you."

Emma's cell door opened and she smiled at me, her eyes full of lust.

"Kneel," she commanded.

I did as she asked and Emma went over to the dropbox with Miss Nellie's freshly arrived cum. After removing the jar, she dripped its contents all over her right foot.

"Alright Samantha, you know what Miss Nellie wants. Lick my foot clean of her juices."

I obeyed immediately, taking in Miss Nellie's sweet and musky nectar from Emma's foot. Emma smelled like flowery lotion, and I was extremely turned on by the pleasant submission of licking her feet. It was such a moment of surrender for me. Dissonant defiance flashed through my head, but I knew it would do me no good. I licked her clean and then some.

"Good girl! You're learning!" Miss Nellie beamed through the intercom. "I think you've earned some more treats from Emma. Emma, why don't you walk Samantha to the fun room and tie her to the bed. Then come back for more instructions."

Emma nodded her agreement. "Yes Ma'am, thank you Miss Nellie."

We walked to the other room and I began to grow very nervous. Emma was honestly really beautiful. Her body was absolutely luscious, complete with huge tits. I wondered if they were real. The only problem I had was the obvious. Emma had a dick! I didn't want to do anything sexual with her because I wasn't gay!

Despite my uncertainty I let her tie me to the bed using the restraints that were already there. She tied me spread eagle, nice and tight. I couldn't budge a bit. Then she left and the door shut for about five minutes. After that, she returned with Miss Nellie in tow.

Miss Nellie was dressed as a dominatrix in every way. She wore leather, thigh high boots with heels. A leather bra and short vest over it. Her giant cleavage popped out leaving me breathless. But what was really scary was her huge strap-on dildo. She inched closer to me. Moving slowly, lording her power over me and pouting her lips. Knowing how completely I had surrendered to her and how humiliating it was. How humiliating it was going to be when she took my anal virginity. She held out her hand. A devious smile came to her face as I realized what she was holding. It was a key.

Emma went down to her knees. Miss Nellie bent down and slowly let a flaccid cock out of Emma's cage. Miss Nellie stroked it gently. It came to life, adding one inch and then another. In a matter of seconds Emma's cock was up to seven inches with a wide girth. Miss Nellie turned to me.

"Since you are such an easy little slut to break, I've decided to move you on to the next part of your training. With a real man it usually takes weeks to get here. But you've wanted to be a cum guzzling slut all along."

"Please Miss Nellie, don't make me do anything with Emma's dick. I'm not ready for anything like that!!"

"Oh you are going to do something. I'm thinking it's time for you to learn how to suck a real cock. And to drink some real cum. How long has it been since I let you out, Emma?"

"Three months, Miss," Emma replied bashfully.

"Ah, so you're going to drink three months of Emma's cum. Isn't that nice. Well, it's a good thing because you need something to wash down your daily pills."

She pulled out a medicine bottle and let me read it. It was full of estrogen supplements. The room started to spin. Miss Nellie hoisted my legs up with a pulley system that ran to the ceiling. All it took for her was the push of a button on the wall. I was now spread wide, showing off my virgin asshole.

"I believe in taking these steps as fast as I can, before you get any silly ideas in your head. So I'm gonna do one more absolutely necessary thing. I'm going to deflower you, little girl."

I was in shock, but I knew complaining would only make it worse. Miss Nellie looked at me expectantly and that's when I realized what she wanted. She wanted me to thank her for all she was doing to me. I took a deep breath.

"Thank you for going through all of this trouble for me Miss Nellie. I can't wait to take your cock and start eating my daily supplements. To have Emma's cum to wash it down will be an added treat."

"Wow, I'm impressed. I didn't even have to ask you, slut. Maybe you really are cut out for this."

With that, both women moved closer to me. Emma straddled my chest and Miss Nellie started fingering some lube onto my asshole. I moaned involuntarily. Emma pulled out a tube of bright red lipstick. She smiled as she applied it to my terrified face. I started to cry from the realization of what was happening.

"Emma, when you're about to cum put these two pills into her mouth. Ready?"

"Yes, Miss Nellie."

"Good."

And Emma brought her cock to my lips. Slowly she entered my mouth and I found the taste of her precum sweet. Miss Nellie kept circling my asshole with her finger, threatening to enter. When Emma reached the back of my mouth she pulled it out and started over. Moving slowly back in as Miss Nellie put her first knuckle into my waiting and wet hole. I gasped with pleasure. I was sucking a real cock and it was turning me on so much! And Miss Nellie was entering me for the first time. I was tied up and open to her intrusion.

Miss Nellie started to add more knuckles and curled her fingers inward, massaging my insides as I sucked Emma's dick. I worked it with my tongue to send waves of pleasure down it. Then Miss Nellie's fingers were removed with a pop.

I felt her strap-on at my entrance. She pushed inside after a slight but agonizing hesitation.

"Welcome to the first day of the rest of your life, Sammi. It's only gonna get more fun from here."

She rammed her whole cock inside me. It hurt so much to be stretched so quickly in my untrained hole. But she had no mercy. Both dicks worked in and out of me with ferocity. After some time the pain was overwhelmed by pleasure. It felt so good to have Miss Nellie inside me. I felt like such a little whore, my painted lips around a real cock. My asshole stretching over Miss Nellie's faux phallus as she pounded me. I screamed and moaned like a dainty girl.

My outfit was tight against my skin, and of my own choosing. Miss Nellie pushed on my legs and smacked my ass as she filled me, calling me her little slut. She told me how easy it was to break me because I was born to be a whore. How Emma took a whole week just to get her to pick her own outfit. She told me I was ready for the whole process and it had only been eight hours.

In my complete humiliation I started to climax, my cum spurting all over my "perfect" outfit. Miss Nellie was cumming too. She let it leak all over me just the same. This left only Emma's cock still holding out as my shame washed over me. I was still sucking a cock, painfully aware in my post orgasmic clarity. Then Emma pulled out and put the pills in my mouth. She groaned heavily and stuck her cock deep in my throat, shoving the estrogen pills down before it.

Then she filled it with thick streams of her delicious, salty cum. The pills were washed down into my stomach along with three months of pent up juices. I gagged and choked but nothing came up. As Emma pulled out of my mouth she pumped the rest of her load all over my face.

"That's a good girl," Miss Nellie cooed. "I think that's the end of your first day. We can let you sleep right here."

The two women walked out of the room. I was left immobilized and covered in cum in my "perfect" and soiled outfit.