My Best Friend's Sis

*****Content Warning: This story contains elements of non-consent and truly forced feminization. If that's not your jam then read something else.*****

It was a normal day for the most part. I was over at Tom's place, and like most Friday nights we were having some beers and goofing around. We were playing Cards Against Humanity with his older sister, Nellie. Tom and I were just about to graduate high school and she was just back from her second year of college. A couple of her friends were there too. Tom and his sister were absolute fiends for this game so they had all kinds of extended packs. There were even a bunch of cards where you fill in your own words, before the game starts of course.

Mostly things went on without much significance as we strung together odd and sometimes disturbing words and phrases. There was this one moment that stuck out to me though. The black card we were playing with read: "The way to a man's heart is _________" Nellie was the judge. Everyone put in their answers. As Nellie laid out the cards one at a time she giggled slightly.

First came "A cheeseburger". Not bad. The next card was "A blowjob". That brought a pretty strong laugh from the inebriated group. The third card was a homemade one and it said "Forced Feminization". All of the girls let out dramatic and unhinged laughter. They couldn't stop and Nellie laughed harder than any of them.

"This one is the winner; I don't care what else is in the pile!"

"What the hell is forced feminization?" I asked, frustrated that my card didn't get picked.

"If you're not careful you might find out," Nellie's friend Emma giggled.

Nellie gestured for her to calm down and began to explain.

"Forced Feminization is a kink where a guy is made to look like a woman, sort of against his will. He actually wants it but pretends he doesn't."

"I can't believe what some freaks are into. Why would anyone want something like that?" I protested defensively.

"I don't know Sam, but you shouldn't judge people for that kind of thing. What if you had a weird kink?"

Nellie eyed me with an odd look. I blushed and everyone laughed. Then we went back to playing the game. The rest of the night was a blast and I actually won in the end.

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I woke up the next morning a little hungover. No surprise there. As I got up from my air mattress and rubbed my eyes I realized Tom wasn't in the room. Maybe he had already gone down to breakfast. I walked downstairs drowsily and stepped in the kitchen to find Nellie cooking some eggs. She was wearing mostly just a long T-shirt. I couldn't tell if there was anything underneath but let my imagination do its thing. After all, she was incredibly hot.

She had long brown hair down to her butt that was so light it lifted like wisps of cloud through the air as she walked. Her face was kind and round, with plump lips and gorgeous eyes. Her body was curvy in all the right ways. In baggy clothes she seemed even a little on the larger side, but tighter fits revealed an impossible curve in when it came to her waist. I tried not to waste too much time ogling her.

"Where's Tom at?"

"He had to go help our aunt with her grocery shopping. She's not too mobile these days. Guess it's just you and me."

That last bit had a bit of seduction in it and I wondered if she had thrown it in on purpose. I shrugged to myself and sat down to eat. After serving me the eggs she sat down to eat with me.

"Last night was so fun! I love that game every time."

She was still using that seductive voice.

"Right? I can't wait to beat you guys again next week."

"Yeah, good luck with that. Hey, when we finish eating can I ask for your help with something?"

"Um, sure. What's up?

"I just need help reaching a box in my closet. I'm gonna donate some old clothes today."

"Yeah no problem."

We finished eating and I followed her to her room on the first floor. I couldn't help but think on the way that she was trying to seduce me. The extra weight in her voice all morning as we spoke. And now she was leading me to her room. I decided whatever was going on, I would play it cool and treat it like a mundane favor. If she wanted more I would find out as soon as we got there. Plus, this was my best friend's sister. If I could avoid the complications that would come with hooking up with her, I would.

"Okay, the box is right up there. Can you get that down for me?"

I went into her walk in closet and moved toward the box. Right as I stepped beneath where the box was the floor dropped out beneath me.

___________________________________________________________

It was dark. I had fallen about ten feet but landed on something soft. The whole floor was made of something soft and loosely piled.

"You alright down there?" A voice cooed through an intercom.

"Uh, yeah. What the hell is going on Nellie."

"Well, you seemed to protest a bit too much last night when Emma played that 'Forced Feminization' card. I figured I'd see if there was something more to it than that."

I was about to yell back at her when the lights turned on. I was stunned speechless. There were three women in cells surrounding me in the room. One of them was Emma. They were scantily clad and just watching me blankly. That was the first thing I noticed, the girls.

As I continued to look around the second thing I had noticed was that the soft padding on the ground was actually all women's underwear. There had to be thousands of dainty panties and bras scattered on the floor that I was standing on. They had cushioned my fall and enveloped me as I crashed into them. I found as I tried to walk I would sink into them. It was hard to make headway across the room.

There were rows of clothing hanging on poles that lined two of the walls, and cameras everywhere. There was of course the wall with the cells imbedded, which leaves the fourth wall. It had a square shaped slot that was covered with glass. And a screen, which I realized had a video feed of Nellie's teasing grin. The wall also had a corridor which went God knows where. Rather than yelling like I had almost done, I asked curiously.

"How the hell did you manage to make this place?"

"Let's just say I met some very interesting people when I got to college. I actually learned a lot more about myself in my first semester than I did any academic subjects. I learned that I love to dominate men. I also learned that if you find the right ones, they will send you a ridiculous amount of money to do it. Remember last year when the family went on vacation and I had to stay around for my work?"

"Uh, yeah. Your family tried to get you to quit the job."

"Well, I didn't have a job. Just a bunch of men, from all over the world. Sending me money just to humiliate them. And blackmail them. While the fam was away I brought in a crew to do some excavating beneath the house. And viola, what you see here was born."

"Wow, you are some piece of work Nellie. Why are you showing me all this?"

"You really are pretty slow, aren't you Sam? Let me break it down for you. I learned I love to dominate men, but I especially love to turn them into women. It is the ultimate submission for me. To give up your entire manhood just for me. And that's exactly what you're going to do Sam. Or should I say Samantha?"

My head was spinning. And not just from last night's booze. There had to be a way to get out of here. First, I guessed I should try reasoning with her.

"This isn't funny Nel. I'm not gonna be some transformation experiment. Can we just end this joke right now."

Nellie's tone grew severe.

"Oh this isn't a joke Samantha. I'm dead serious. You may not realize it but I have you under my total control. There's no way for you to escape or contact anyone. You are essentially my slave."

"You can't keep me down here forever Nellie. Everyone knows I was here last night."

"That's true, they do know you were here. But when I tell them you were planning on hiking today they'll just assume you got lost. I'll probably even scatter some of your stuff in the woods just for good measure. Now, the sooner you accept your fate the better. The first step is this, take off all of your clothes and put them in the drop box."

The glass pane lifted on the square hole in the wall. She was gonna leave me naked down here, and in front of all these women. I couldn't give in so easily.

"Not gonna happen, Nel. I'm not here to be your bitch."

"Okay, well when you're hungry just press the red button and we'll talk."

Silence followed. She obviously was in no rush to get this started. I began to consider my options. I should mention that I was rock hard by now. She was so hot and something about her dominating demeanor got me going. But I was not a slave to my sexuality. I resolved to hold out longer than her. And in the mean time I decided to try to find a way out.

Getting up through the trap door I had fallen from was the first option. There was no way to climb up there though. Then it hit me. Maybe if I stacked all of these clothes it would get me up there. I got to work. Handling all of these ladies' undergarments was getting me all worked up. They were so silky and soft to the touch. They smelled so sweet and feminine. It wouldn't be surprising if they were doused in pheromones. I had a raging hard on as I piled them up. Finally after about twenty minutes I thought I might have enough.

I began to carefully climb up my lingerie wall. It was a little bit shifty but I did my best to keep my footing. Right as I was nearing the top the whole pile collapsed on me! I was buried in panties and bras completely. I struggled my way out and after much effort was able to breath fresh air again. The pretty smell of them was now stuck in my nostrils overwhelmingly. It occurred to me that this wasn't going to do the trick. Even if I got up there I didn't know if I could open the trap door.

I peaked my head into the dropbox. It had no way out, even though I imagined it traveled up like a small elevator. That left only two options, ask the girls what was going on or go check out the hallway. I looked over to the girls and they smiled, but remained silent. They were just as trapped as me, and who knows maybe they were in cahoots with her. I decided to explore.

As I entered the hallway I saw it had a variety of rooms. As I tried each one I found the doors were locked. All except for one. The room on the end was full of sex toys. It had a bed with restraints and a sex swing. Dildos were hanging on the wall on carefully designed hangers. It was like a store display. Suddenly the door closed behind me.

"I see you found the fun room," the intercom said in Nellie's sultry voice. "So curious my little kitten. Well in this case it won't kill you but it may speed up the process a bit. I've got a game for you."

I stood in silence, feeling too powerless to properly defy her. I waited for her to continue.

"This game is called 'Frog in Boiling water'. I'm going to up the temperature one degree every five seconds until you show me your blowjob skills. Let's use the purple one over there."

A light turned on, highlighting a giant purple dildo that was hanging on the wall. I looked at it fearfully.

"Annnd, go."

The temperature was going up by the time the first minute passed, sure enough. I didn't see any way out of this but couldn't give in. I ran over to the door and tried to open it. Of course it was locked. I banged on it helplessly as I began to sweat. It was getting hot in here so quickly. After about three minutes had passed of me trying desperately to get out I realized I had no choice.

It had to be 100 degrees in here. I slowly and timidly made my way over to the dildo.

"That's it, cutie. Now get on your knees."

I did as I was ordered and the dildo moved down to the perfect height and angle. I was looking up at it as I moved toward it. A camera on the wall above it also moved down so I was looking right up into it.

"Now I want you to look up into the camera with puppy dog eyes, smile, and then suck that dick. Enthusiastically."

I once again did as I was told. My lips approached the dildo. I was impossibly hard. I wrapped them around it and began bobbing on it. Looking up sweetly and taking it deep into my mouth.

"Wow, look at that boner. You're really enjoying this aren't you, bitch?"

I moaned from her teasing and sweated as I continued to suck the dildo. At least she had stopped increasing the temperature.

"Now, my steamy little slut, you're going to swallow it into your throat. I want to hear gagging. But don't forget to keep looking into the camera."

I continued to comply, at this point absolutely drunk with arousal. Why was I enjoying this so much? I had never wanted to suck a dick before but something about being forced was working wonders for me. I choked on that dick like there was no tomorrow until Nellie told me to stop. Tears rolled down my face.

"Now, I'm gonna let you out of this room. You are to go into the other room, strip seductively for the girls, and place your clothes in the dropbox. Sound good?"

"Yes," I replied shakily.

"That's 'Yes, Miss Nellie'," She corrected.

"Yes, Miss Nellie."

I went back down the hall and looked at the girls. They were smiling silently again. Then I noticed something. They all had bulges in their panties. Not like an erect penis but more like a penis contained in something. A memory flashed in my mind. Once, while watching porn, I had encountered a video where a man was locked in a chastity device. I had a moment of instant recognition.

"Miss Nellie?"

"Yesss?"

"I can't strip in front of them! They're dudes!"

"Wrong, Samantha. They were dudes. Just like you were. But now they're ladies. Just like you are. Yes it's true; they're farther along, just like you'll be. But if you're not good, you'll be the first one to get a real pussy. So strip."

It was clear to me. There was no way out of this. I could try and hunger strike as long as I wanted, but Nellie had truly endless resources as she had demonstrated. I began to strip. Seductively, just as my tormentor wanted. The girls oohed and awed and giggled as I took off every last thread of clothing and placed it in the dropbox. The glass closed, and the clothes disappeared up the chute. After a moment of silence, Miss Nellie spoke again.

"Good girl, Samantha. Your next task is to get dressed. Any outfit will do."

I picked up a pair of panties and held it out in front of me. I was filled with fear. How could I, a man, wear something so dainty? So feminine? I was a man, damn it!

"You can't do this to me Nel! I'm not gonna do it."

"Hmm, you may notice it's a little cold in there without clothes. In fact, it might be getting colder and colder."

The intercom went silent. I looked at the screen to see if she was still there. The only thing that played on the screen was a video of me looking up while enthusiastically sucking on a purple dildo. Proof of her previous victory. I swore I'd let her freeze me before I would put on women's clothes. I stood there quietly, scowling. As a chill slowly crept over my naked body, goosebumps formed. I crouched to the floor to gather myself up and stay warm.

I sat there for probably 20 minutes, noticing that it wasn't getting any colder. She wasn't going to freeze me, just leave me there uncomfortable. I shivered in defiance for three hours. But I knew that she was sitting up there in comfort, just biding her time. Who knew what she was doing. By now, she could have been chatting with Tom or her parents. They would carry on laughing, with no understanding of what a monster she truly was.

There was no way I could last much longer this way. Even if I did, there would be the same result. Eventually I would give in. I knew I would have to wear a full outfit. I couldn't help but think, "Maybe complete with a fur coat?"

I picked up a pair of black panties. They were relatively plain and not too girly. I pulled them up my goosebump ridden legs hopelessly. Then I found a bra to match. I felt so silly wearing these clothes but still struggled to fight off my hard on. I didn't know if it was wearing the clothes or just the feeling of being controlled by such an overwhelmingly sexy woman that got me off. Whatever it was, I was slowly becoming helpless to it.

A pair of blue jeans and a skimpy camisole later (the least girly clothes I could find), I was ready to push the button and let her know I had submitted to her demands. I also managed to find a cardigan to keep me a little warmer. I pressed the button to find she was ready for my response. Immediately her face popped onto the screen, replacing the loop of my cock-sucking.

"Your outfit needs shoes, silly. You could never go out in the world looking like that."

I lowered my head and began to look around. A light glowed from the first door in the hallway. When I tried it, it was unlocked. Sure enough it was full of different kinds of shoes, all of which were pretty girly. I found a pair of sandals that were my size with little flowers etched into the faux leather.

"Aww, those are so cute! A perfect fit for that outfit. I think you've earned yourself a little bit of warmth."

Over the next couple minutes the room returned to normal temperature. I sat on the mound of undergarments trying to keep my boner hidden. I didn't want her to see how much this was turning me on, but it was difficult inside the tight pants.

"Wow, you really love your new clothes, don't you? You can't hide your hard little clit! Don't worry, I don't blame you. I think you're kind of pretty honestly. But! I think we can find something better for you. So here's your next challenge. Before you can eat again you have to find the perfect outfit for yourself. This is something you can only do by trial and error. So, when you think you've tried on the perfect outfit come into the second room."

The door to the second room lit up. I feared to find out what was in there.

"When you enter the second room, smile and pose for the cameras. This will be known as the camera room. After four cute poses for different cameras, the room will send me your outfit. If you have chosen the 'perfect' outfit for you, the room light will turn green and you can come and get your meal. If it turns red, you have to start all over. If the room turns yellow, you are getting pretty close. Ready?"

I sighed defeatedly. "Yes Miss Nellie."

"Aren't you going to thank me for all of the beautiful clothes?"

She hadn't threatened anything to make me do so, but I was starting to learn that every defiance would result in consequences.

"Thank you Miss Nellie. I love all of the beautiful clothes you're letting me try on."

"You're very welcome Samantha. I just can't wait to see what kind of pretty outfits you come up with! Now get to work."

Her video feed was replaced with a revolving compilation of me sucking the dildo and reluctantly putting on the clothes, especially the moment when I first pulled the panties up my legs. I was disheartened, but my stomach had begun to growl. I didn't know how picky Miss Nellie would be about my outfit choice, so I knew I needed to begin right away.

The first thing I thought to do was try for another outfit that wasn't too girly. But then I realized Nellie wasn't going to let me off that easy. So I put on a dress that was pretty feminine. It was blue, with sequins decorating the bust. It went down almost to my knees. I paired it with matching panties, these ones containing some lace. And a pair of little black shoes that seemed just cute enough to complete the outfit.

I walked over to the second door and opened it. It was now unlocked as I expected. I looked at the first camera which was at eye level and crossed my arms. It snapped a picture with a mild flash. Then I posed for the second camera, a little lower and pointed at my face. Figuring I should pick a satisfactorily feminine pose I put one hand on my hip and pouted my face. This posing continued as I showed off my shoes by pointing my toes and finally gave the old 'tiger' pose as I faced a ceiling mounted shutter. I couldn't think of anything better, honestly.