Three Girls and a Sissy on Dares

I am Phil, a 24 year old art student from Sweden.This year as part of my final exam our school decided to do a course exchange with other countries and I was randomly selected to stay in Scotland.

I would stay in Glasgow for 3 months at one of their shared accommodations and was expected to present some sketches and paintings on my return.

Jimmy and Andrew were my flatmates for the first two weeks till we suffered a fire in our building. There were no casualties but we were asked to evacuate for a few days. With a shortage of rooms, we split up and I ended up staying with a classmate named Amy who kindly accepted the school's request till all was sorted.

On Friday evening, after all that chaos, I found myself nervously standing in front of the door of my new flatmate's apartment. I gathered up my courage and knocked on her door.

As the door opened, I was greeted by a stunning, beautiful 27-year old woman from Edinburg with an even more stunning smile.Her bleach-blonde hair tied in a high ponytail and her amazing eyes-green with a faint tinge of blue, drew me in and almost hypnotised me. Smiling sweetly, she said," Hi, so you must be Phil.Just come in! I am Amy, by the way."

As I closed the door and followed Amy to the living room, I tried to keep my eyes above her shoulders, but I struggled where to look. It felt like she decided to wear the shortest skirt and a v-neck top to see how far she could make me uncomfortable.

"Where is your luggage? Bring it in and I'll show you my place, I'm sure you're dying to have a shower." Amy walked into the kitchen.

"Thanks, I definitely need one. I spent the last few hours around so much smoke, I probably look like someone who cleans chimneys. I am all in with that but I have a small problem... "I turned my head away.

"What is it Phil? Don't tell me you're allergic to water," replied Amy with a laugh. "Sorry, we've only met and I'm already giving you sarcasm."Amy's expression softened.

"No, that's definitely not the case. It's just that all my belongings were left behind In the building and I have no clothes to change. By the looks of the apartment, I doubt anything was left unburnt.

"Well, I don't see that as an issue Phil. I'm sure I'll find something for you to wear. Just get in the shower and leave your clothes by the door and I will get you clean ones and tomorrow we will think about the rest,"replied Amy with a mischievous smile.

That must have been a good twenty minutes. I totally lost track of time but when I finished, I was all nice and fresh. I opened the door and stuck my right arm out trying to reach for whatever Amy had left for me.

"Amy! What is this!" I shouted across the hall. "Good try but I won't wear this. Very funny Amy. There is no way I am just going to put your girly clothes on."

"What!" said Amy while walking toward me with a slightly devilish smile. "You don't have much of a choice here. I am offering you a place to stay and giving you clean clothes to wear, so the minimum I expect is appreciation, definitely not shouting. Are we clear?"

"Sorry, you're totally right. I had a crazy long day, no intention to upset you. Can we please start over again." I replied, desperate not to piss my flatmate off.

"I'm sure we can," whispered Amy, leaning into my ear."This is what will happen-- we have two options here. Either you stay and follow what I say or you just leave now. Am I asking too much?"

"Not at all, it's just that I feel embarrassed putting on these tight thigh-high shorts and girly pink top knowing that you will be looking at me.

"Hmm, so that's what it's all about. You think I didn't notice you looking at my arse or boobs earlier on when I was not watching? How do you think I felt? Not that shy back then!"she replied angrily.

"All right then, give me those clothes and wait here, I will see what I can do," said Amy, rolling her eyes.

She took a couple minutes and then was back with a new pile of clothes."Here, take these and hope they fit you better." She laughed heartlessly. " Meet me back at the living room in five and don't forget to wear it all. you don't, you may just leave now.

I couldn't believe it. Amy had left me with more humiliating clothes.I cursed my big mouth which seemed to have landed me in a worse situation than before. This time she gave me a pink mini-skirt, silky white panties with red hearts,a white crop top with the letters 'Barbie' written in pink glitter and--Oh god! A pair of white thigh-high silk stockings. I didn't have a clue how the hell I would put all that on.

There was a knock on the door and a short whisper-- "Two minutes and I come in,don't make me wait."

I put everything on as fast as I could and walked to the living room avoiding her eyes.

"Well done!" said Amy, giving me a naughty look,"Was that so difficult? Not bad.You still need some adjustments but sure, we can work it out. I understand you are a bit embarrassed but to make you more at ease, I left the flat darker than usual.I'll put a few candles on the table while we chat and watch some telly. How does that sound?"

"Good with me Amy, thanks."I replied, getting used to my situation.

"Glad you're on board then.Here is the plan then. Sit next to me and I'll go through our flat share agreement. I'll pencil down all my terms and expect your signature by the end of our chat."

"First of all it is tradition here that on the first night we do a small welcoming party."Amy stated nonchalantly.

My eyes opened wide open and I wanted to jump out of the sofa at that instance.It was definitely not happening especially while wearing those clothes.I thought to myself,"There must be a way out," but I was too scared to say anything which I might regret later.

Amy cut off my train of thought and asked me with a smile--as if she was reading my mind--"Don't worry, it won't be that kind of party. I was thinking something more natural...Do you smoke weed?"

"Weed?"I asked hesitantly.

"Yep, you know what I'm talking about, do you smoke?" Insisted Amy

"Well to be honest, I do from time to time but generally only when I'm alone.I don't trust myself around other people as I talk too much and...."my voice trailed off.

"And what? You can't just say half a sentence and stop like that," continued Amy.

"Hm, not sure how to say it...I guess it makes me overheat sometimes."I tried to play it off.

Amy laughed and said out loud,"Oh you get hard? Is that what you mean?"

"Yes, but I guess you already know what I am talking about."I replied, slightly miffed at the fact that she wasn't taking my problem seriously.

There was a silence in which Amy opened a silver box that was at the coffee table,got a joint and took me by the hand to the kitchen window. Bending over the sink slightly, she started smoking. She passed over a couple times and then told me to finish it.

I was feeling super dizzy by that time. Amy pointed out that I needed to get closer to the window and getting behind, she pushed me forward. Without any notice she slid her hand up my leg and, grabbing my balls,said in a very innocent voice,"I love how these silky panties feel against the skin, don't you? Just wanted to be sure you're wearing them and that you're telling the truth about being hard when you smoke. Come, let's go back in, we have work to do."

Back at the sofa Amy started to get her notes for our agreement and before I knew it, everything was ready.

"Here we are! It's all set. I will read it and I hope we are all good."She replied,clearly enjoying her dominance over me.

"First, you will complete any task or instructions from now on without hesitation."

"Second, you will wear what I give you daily without question."

"Third, it's my place and you will be my girl flatmate from now on and behave like one. Even if I decide to walk around the house in my underwear or naked, keep in mind that eyes shouldn't meet and don't make it awkward."

"Fourth, I do find girls attractive as well, so if you are a good girl you may have a treat from time to time. By the way, I want that man bun down. Loose hair and shaved face and body is a must."

"So Alice, do we have a deal? The clock is ticking."

"Well, that's a lot to process. I was not expecting this but I have nowhere to go till I'm back on my feet.I...I guess it's a yes."

"Go on, sign it then," said Amy.

I took the pen and as I finished signing it, I suddenly realised what she said."Did you just call me Alice?,"I asked, incredulously.

"Well of course! You surely would not call yourself a man in your state, would you?"She laughed derisively.

"Good girl," said Amy with the biggest smile,"so the first task I want you to do is take these two joints I have on my magic box, smoke both in the kitchen and come back when you're done. One after another... understood?"

"I'm not sure how I'll function after that." I replied."I will probably struggle even to find my way back but I will give it a try.".

"Oh silly! Why would you need to function? Just give in to the magic and let me guide you.", Amy said, giving me a gentle slap on my butt and winked at me."Go on, I'll be waiting. When you're back I'll have some drinks ready. You know the night is young, don't you Alice!

We had some shots and some laughs and to be honest I hardly remember what happened after that. I guess I must have passed out.

All I know is that I woke up on the sofa, early Saturday morning with the view of Amy's perfect peach bottom in a pink thong near my face, not leaving much too to imagination and a loose white top, while stretching to open the curtains.

"Wakey wakey, sleeping beauty, hope you're not feeling too rough,"she laughed. "I am about to get ready and head to the gym. Shower is all yours. Hope you like what I left for you to wear Alice, see you shortly. "Oh and don't forget, good girls are clean and smooth at all times."She added, as she closed the door with her perfect ass.

Suddenly all the events of the previous night sank in. I had a vague idea of the smoking and drinking but that was it.

"Wait! Did she just call me Alice and am I still wearing what I think I am under my covers?"was my first thought after waking up properly.

I remembered her mocking voice and couldn't believe I had agreed to be called by a girly name like Alice.

I rushed to the shower and I kept thinking to myself-- "What the hell happened yesterday! If I can only find my old clothes I may have a chance to escape."

I took over an hour trying to convince myself to run away from her apartment. "Let's get ready then, I can do this," I thought. Maybe I could survive another day till I got my clothes back.

I could hear the keys on the front door and her angelic voice saying," Hi sweetie, I'm back, Ihope you missed me.", just as I was leaving the bathroom.

"Look at you Alice, I love that summer dress, pink really suits you," said Amy in an evil tone. I bet you had lots of time to reflect and were running out of ideas on how to escape this rabbit hole."

"Let me make this all easy for you then while we have our first smoke of the day!"

"I'm sorry but I had to bin your old clothes since they were totally ruined."

"I also got a call from the college this morning and they don't mind that you complete the remaining of your art course from home if you're happy as there is no mandatory attendance in class. All you need is to take back home your projects for the final exam in Sweden in two and half months. So I guess this is all sorted."

"... and finally my favourite! To be sure that you would follow through with our little agreement, I needed some reassurance. I took some pictures of you dressed all slutty and passed out on the sofa. I even managed to take this last one with your cock outside your panties holding it. Was a tricky one as I needed to make you hard before. Not sure if it was my hand technique but I accidently made you cum. Anyway, it looked good on camera...and I bet it would look even better to your friends if you decide to violate our contract,"said Amy looking deep in my eyes."I hope I don't ever need to use them."

"So Alice, any questions?"

"Why all this,"I replied in a low, subdued tone, hardly able to believe what was happening wasn't a dream--or a nightmare,"why me?"

"Hm... let me see!"said Amy with a smile,"Because I can and when I want something I get it...and I have been waiting for this opportunity for some time!"

"What opportunity if I may ask?"I asked, fearing the answer I might receive.

"The one where I get to own a sissy slut for real! All my friends talk and fantasise about it but I guess none of us have been so lucky... till now. I'm so excited!"

"Now let's stop with this useless chatter and get me a smoke. I will join you in the kitchen shortly. You need to get more relaxed for what is coming next."

Amy got up and ordered me to smoke the entire thing while she stood there in front of me. "I'm so glad to be out of my gym clothes, that bra and pants were killing me.Hope you don't mind me walking around the house with my skirt and a top without any underwear."said Amy with a teasing smile on her pretty face from which I couldn't take my eyes off, even though I wanted to hate her with all my heart.

Her hands were moving under her white t-shirt over her perfect big breast. She was complaining about how sweaty she still was and I could see her nipples getting hard and visible. While biting her lip she lowered her right hand under her skirt and whispered,"Even my pussy is sweaty.Oh dear, I do need a shower!"

Amy turned to go to the bathroom and without a moment's notice she suddenly stuck her fingers into my mouth and asked me,"Do you think I'm salty? I guess you are too busy drooling like the little slut you are to understand the difference,"replied Amy to her own question," it's definitely shower time."

I went back to the sofa to catch up with my dizziness and lack of proper sleep, still tasting Amy's heavenly pussy on my tongue, while she went into the bathroom to wash up.

That evening we had takeaway and watched a movie.10 pm was bedtime for Amy and I was left to sleep on the sofa for the second night.

Sunday arrived and that was the day everything went south.

I heard the doorbell ring and Amy was there within seconds.She took an amazon parcel and I could see how excited she was but her secrecy bothered me.

"Sweety...we need to talk about some ground rules here!

From now on, you need to be up and ready every day before me,.I want you showered, fully smooth and dressed up for 7am to tidy the house.The spare room at the back is where you will sleep. I left you a mattress, a pillow and a small box by the door where you can keep your daily clothes."Amy commanded in a domineering voice.

"So Alice, the bathroom is all yours now.You have one hour to get ready and then you can meet me back here, we have a lot of things to do today and I can't wait to start."I went off to the bathroom, too scared to argue.

I got back to the living room wearing a black mini skirt that hardly covered my arse, a red thong underneath and a bra with a white top with my dark blonde hair down to my shoulders. Amy clapped her hands and said,"Aren't you adorable! You totally look like a slut in those clothes, I love it!"

"Now sit here, we have this box to open and need to go though the second set of rules."

Amy started unpacking and selecting each item carefully while simultaneously giving me a short briefing before placing them on the table.

"This here is your eye shadow and a cherry lip-gloss.We apply like this, let me show you."Amy took the lip gloss and generously applied it to my full lips.I couldn't see how I looked by judging by Amy's expression, there was little to no hint of my original facial features left. "The next one is your new silicon breasts, I got you a D cup which is the same as mine and will fit perfectly on your bra.Put them on,"commanded Amy.

"Now we can move on to the fun part,"Amy laughed evilly, and continued,"since I noticed that you are not walking around the house moving those hips properly like a girl, I got you this to help. It's a new product on trial on the market but I have faith in it. "

Amy made me stand up, pull my skirt and panties to the side and without saying more she just put some lube on my butthole and forced a anal plug all the way in, making me jump, as I felt the unfamiliar foreign object in my ass stretch it out to limits I had never experienced before.

"This here is your hormonal lube and new plug and I expect this to be in you at all times with the matching pink chastity cage that I'll put on now and keep the key to myself."I suddenly felt her soft fingers grab my cock, which had become hard from inserting the butt-plug, and without further ado, she squeezed it firmly till it deflated like a pricked balloon and locked it in a tiny cage.I was shocked beyond belief and as I felt my cock try to get hard, I experienced immense pain and my erection vanished instantly.

"Next one is your best friend John, he loves to be sucked and fucked and it's your new 6 inch suction dildo that you will use to abuse your throat with a few times a day. Failure to uphold this practice, I guarantee you, is a bad idea.Last but not least, this one is mine but I will show you when I believe you're ready and deserve it.However the same applies if I think you need a punishment. Hope you love surprises!" said Amy, chuckling at my sorry state.

For the next four days it was hell on earth.It was like Amy had the devil inside her and she kept pushing and pushing me with my training. I was left at times sucking and riding that dildo to the point I could not take it anymore and the more I suffered, the more she was amused.

Friday arrived and Amy told me first thing in the morning that she would go easy on me and I felt relieved. She was also going out that evening with some friends and at the back of my mind,,"This will be my break for a few hours," I thought.

Around eight o'clock I got a few messages from Amy, most of them were pictures of the girls having drinks and having a good time.Then this message came in, totally blindsiding me,"Hey babe, I am about to get on the cab back home. Party is not that bad but my friends are a bit bored. Hope you don't mind these two coming with me."

This was my worst nightmare. I had nowhere to hide now. Worst of all they were all drunk and Amy was giving me more instructions,"Get that arse moving and put on the bright pink skirt and matching crop top and the black lacy underwear. We are nearly there!"

I could hear their laughter and the struggle to open the front door. As they walked in, Amy threw her jacket on the floor and kicking her shoes off, said out loud,"Ladies, this is Alice, the slut I mentioned about earlier. Anything you need just ask her and she will fulfil each of your wishes"Amy continued,turning to me-"and at my side wearing this sexy black dress with the strawberry blonde hair is Sophia and this hot brunette with short hair is Molly."

"Nice to meet you!"I replied hesitatingly.

"Alice, be a good little girl and get us some wine from the refrigerator.I want these glasses full at all times."Amy commanded me, giving me a light tap on my bottom.

As I came back from the kitchen, they were all sitting and chatting and Molly said,"

I know! We are already tipsy and this may not be a good idea but what about if we play our favourite game! Would you girls be interested in a dare game?We roll the dice and the other two decide the fate, what do you say?"

"Love it, I'm up for it."I said."Me too! Count me in,"said Sophia.Amy also nodded in agreement.In my mind I thought,"What could possibly go wrong after all that I have been through?"

I watched them being silly and groping each other, kissing and giving tasks to each other for a while and felt myself getting hard.