Caught Messaging Master Pt. 03 - Saturday

I woke up Saturday morning after a long sleep worrying about my situation and how I could get out of it. I was stuck in the hotel room with Mark. No male clothes, no bank card or money on me, just my phone. But I couldn't exactly phone a friend to collect me because I'm sitting here with my plucked eyebrows, long French nails and big plump lips. That's without mentioning my long blonde hair and tits stuck to me. The worst part of it all is that I had to wear this chastity cage all day every day with no way out. I don't even know where the key is. I heard Mark getting out of the shower, he looked at me.

"Morning Katie, maybe we got off on the wrong foot yesterday evening. Today will be a better day for you if you behave yourself." he said.

"Mark, if I behave myself and you're pleased with me do you think you could let me take my cage off?" I begged. Mark laughed.

"I'm afraid not Katie, Lucy has the key. you're locked in that until she thinks you don't need it anymore. Plus, it's cute, a sissy doesn't need a dick. Lets face it you're never going to use it again anyway are you. The only way you're going to cum is when there's a dick ramming that little ass of yours." he said. Mark walked over to the table and started to dry himself.

"I have something for you, Lucy asked me to give you a note every morning so here it is." he said. I opened the letter.

"Hey babe, so as I said in yesterdays message, tonight you're off to a brilliant drag night just down the road from your room. I've booked a meal in a restaurant next-door for you and Mark. I thought you two should spend some romantic time together, it'll be so cute darling. To get you ready for your candle lit dinner with your new hunk you have an appointment in a shop called 'Sophie's' on the high street at 11 so you will be looking your beautiful best. I'd say don't put out on your first date but I think it might be too late for that! enjoy!"

I looked up at Mark in shock.

"Mark, where's my phone I need to phone Lucy and sort this out, I cant keep this up! She wants us to go to a restaurant tonight and a bar after! I need to get this to stop." I had tears in my eyes now.

"Don't get upset Katie, you're here because it's what you wanted. You messaged me online and told me all about the things you love, how you love being humiliated and wanted a real mans cock. Well here it is, enjoy it, this is what your life is from now." mark said. I didn't know what to do next.

"Plus after last nights events you can't be trusted with your phone anymore so I'll be looking after that until we leave." he said with a grin.

"Now I'm going to the pub for a couple of drinks and you have an appointment a few doors down at 11 so you better get dressed quick. I want you looking sexy tonight!" he said. My next outfit was out on the bed for this morning, I had no say in the matter. Frilly pink French knickers, a long sleeve, white, stretchy top which will massively emphasise my tits. Some white leggings next and he handed me some trainers and a cap to finish my outfit off.

"Ok, so where's the bra Mark?" I said with my arms out.

"That's all that's on the list for this mornings outfit from Lucy, no bra" he said.

"There must be bra. My tops white mark, everyone will see my nipples through this top!" I said in a stroppy voice.

"Too bad for you." he laughed to himself.

I quickly jumped in the shower, it was incredible, feeling like as much of a woman as possible, my hands through my hair, rubbing my boobs, my nails rubbing against my silk smooth bum. If I wasn't in my chastity cage I could've cum on the spot. Even looking in the mirror brushing my teeth and seeing my thick juicy lips, my eyebrows and my new eyelashes. I loved it, I felt so sexy. I was living in a dream, but once this dream was over maybe my life might come crashing back down. I pulled my knickers up over my bum and put my top on.

"Hang on one more thing, that little clit of yours will make a bump in those leggings, you definitely wont pass for a girl that way will you? come here." said Mark. Mark grabbed my cage and I let out a moan. He tied some string around the tip and yanked it between my thighs, he tied the other end of the string to the top of my knickers. My cage was now lodged between my legs.

"I'll give you something to remember me by when I'm out." he said. He pushed me against the mirror and pulled my ass out, he started to touch himself, I stuck my bum out and grinded against his dick.

"You're getting fucked so hard tonight bitch." he whispered under his breath.

"Tell me you want it now!" he shouted.

"I want your dick in me master, I need it, please let me have it." I said in my best attempt at a seductive voice. Mark pulled my underwear down and let out a moan, he came all over my bum. Drenched it.

"I guess I'll be changing my knickers now then." I giggled.

"Nope" he said, mark finished emptying his load all over my bottom. He picked up a butt plug from the side and stuck it in me. He pulled my knickers back into place and gave me a light spank.

"You're leaving my cum all over your ass crack until you get back here in a few hours." he said.

"Thank you master" I replied with a cheeky smile. I was really starting to get into the swing of things now. I put my leggings on, my trainers and my cap. The shape of my ass looked unreal in these leggings, I couldn't stop looking in the mirror. Mark left while I admired myself. I thought to myself if I have another 2 nights of this I might as well throw myself into the deep end. I don't know when I will get a chance like this again. Hopefully Lucy forgives me when this is all over and this was just a big game to let me have my fantasies.

I left my hotel room and strutted through the hall and down the lift, wiggling my bum in these tight leggings every step of the way. I looked like a girl on the way to her work out at the gym, but a girl with her pink knickers and nipples clearly on show while there. I could feel the cum dripping down my ass as I walked down the street and it made my chastity cage twitch. As I was going to a salon I didn't go for much make up, just a little foundation and lip gloss, at only 5'8 and a size 8 with the work already done on my face I felt safe without too much make up. I walked into the shop.

"Hey, I have an appointment at 11." I said.

"Oh, hi Katie, follow me through to the back. I'm Sophie by the way." she said.

"You look fantastic Hun, it'll be a job improving you." Sophie giggled and I laughed back.

"Thank you, you look very nice yourself!" I said. Sophie looked down at some paper on her desk.

"Ok, so if you want to sit down we'll get started. Lucy has given me a list of things you want done so first I'm going to just removed your nail colour, touch them up a bit so you have French tips and no paint on them if that's ok. She's such a doll, it's hard to believe you two were ever an item, you're both so beautiful. I'm so glad you're both happy now! Ok, after the nails you're going to get a facial and I'm going to give you a new hair style for your date tonight." she said with a big smile. Sophie worked on my nails over some small talk, she gave me a new look by curling my hair and gave me a fringe, I loved it. I felt so feminine sitting chatting about clothes and men casually while having work done. I laid my head back as I had my facial when Sophie brought her friend in, suddenly I felt two Sharpe pinches in my ears!

"Ouch!" I said.

"Don't worry babe, Lucy wasn't sure you'd be completely up for an ear piercing so we thought we would surprise you." she said.

"Oh my god." I said. I thought to myself how am I going to explain this to the guys in work, I cant avoid this one.

"Normally for a first time we go with studs but Lucy has especially requested the biggest hoops we had so they're 12cms." Sophie put my earrings in and I took the cucumbers from my eyes and looked in the mirror.

"Oh my, I have hooker earrings!" I said with my mouth wide open in surprise. The girls laughed at my reaction.

"To be honest from what Lucy told us you're lucky to be getting away with this, I would've had my boyfriend beaten up if I saw he was messaging guys behind my back! You deserve everything you get darling, hopefully this guy tonight fucks you're brains out." they both laughed out loud to each other. I really wished Lucy would keep my dressing a secret and not tell her friends. None of them would ever look at me the same way. I don't even know this Sophie and her friend but they seem to know everything about me! Sophie did all of my make up, new false lashes, she touched up my eyebrows, eye liner, pink lip gloss. Everything.

"There you go darling, you look like a real life Barbie doll! Let me just get a picture to send to Lucy, she'll be pleased with this!" said Sophie. She took the picture and I thanked her, I walked back to the hotel room, by this time Marks cum was dry in my knickers, I badly needed to change my underwear.

I got up to my room and Mark wasn't in but tonight's outfit was laid out on the bed, a royal blue bodycon dress which covered my boobs and had long sleeves, there were matching heels and a choker. Tonight's underwear consisted of a pink satin thong and a matching bra. I got dressed, from head to toe there wasn't a shred of man left in me. My hair was long blonde and curly, my face was unrecognisable, the bodycon dress made my ass and tits stick out. My new French tip nails, my legs would be on show tonight. I stepped into my heels and posed in front of the mirror. My chastity cage stuck between my thighs with no chance of escape, I sat down on the end of the bed with my legs crossed waiting for my daddy to come home, hoping he would be pleased with his new look sissy.

As I sat on the end of my hotel bed in my 5 inch blue heels, my royal blue bodycon dress hugging my bum I admired the work Sophie had done earlier on my nails, the new French tips looked so hot.

All I could imagine was how they would look around marks dick. Maybe Sophie and her friend were right, I deserved everything I would receive after messaging men behind her back. That's not even including my first crush from school that I still kept in touch with, but she knows nothing about Katie, that was completely different.

I could never really satisfy a woman like her, I'm made to please men, but my life now at 25 is as a male. No one in my life has a clue about my dressing. I stood up and pulled my dress into place, it was just about knee height so surprisingly not slutty at all, more classy. I put my hands on my hips, shifted my hair around. I loved my new fringe, my lips were now really starting to look as plump as I imagined. I gave my chastity cage a little nudge back through my thighs and pushed the plug back into position. The hotel door opened.

"Well how's my little princess Katie doing?" mark said.

He was actually starting to grow on me now, which is surprising because last night he fucked my ex girlfriend right in front of me before I swallowed his cum from her pussy.

"Hey Mark, I'm actually doing really good thanks. Sophie's was fun, I got my ears pierced, nails done and a facial. How was your morning?" I said.

"I can see she's done a great job, you look beautiful! I cant wait to show you off in this restaurant later. I have a big surprise for you tonight! Babe I was going to have a shower but seriously your ass is making me want to fuck you right now." said mark.

"I took so long to get ready babe, I don't want to ruin it all, this feels so good against my smooth ass babe, and look how it shapes my tits daddy." I said. I rubbed my hands all around my bum and pushed my boobs together while starring up into marks eyes as he towered over me.

"You're asking for it now you horny little slut." Mark pulled me close and gave me a passionate kiss, his tongue deep in my mouth. This was my first kiss with a man, I couldn't think straight, my body just went weak and I lost all control. His hands were all over my body while we kissed, he lifted me up and dropped me on to the bed.

"Legs up now." I didn't need any further instruction.

"Yes daddy." I replied.

I lifted my legs, and his dick came out, as did my butt plug. He got onto the bed between my legs as I got ready for our first missionary sex. But mark was in no mood for romance. On my back mark threw my legs over my shoulders, my toes now touching the bed above my head, he pulled my chastity cage between my legs then pushed them together. So from marks viewpoint all he could see was my legs closed together with my chastity cage poking out. I was folded in two and couldn't even reach my cage to pleasure myself.

"Oh, daddy I think there's lube over..." He stopped me mid sentence and slapped my ass.

"We wont be needing any of that." he spat on my ass and rubbed my hole. Next came the tip of his dick, I moaned.

"Ahhhhhh yes, fuck yes daddy... fuck me hard." I screamed.

"Don't worry about that slut you've got that coming." he said.

Mark pounded my ass for the next five minutes, I couldn't move, I was completely stuck while he leaned over my folded body He completely impaled me. He finished in my ass and laid there for a few seconds, letting out his final humps so every dropped was in me.

"Fuck Katie, that was good. I'm going to get ready for the meal." he got up and walked into the bathroom.

I was so horny I needed to cum. After a few more thrusts from mark and I might've exploded everywhere without any touching. But my brain was now so focused on pleasing him satisfying myself was not a priority.

I got up from the bed, legs shaking, pulled my thong back up and placed my plug back in. Mark never instructed me to but I'm sure that's what he would've wanted. I pulled my dress down and sorted my hair out. I put my pink lip gloss on and i was ready to paint the town red with my man.

When he walked out of the bathroom all 6'4 of him was man. A smart white shirt, braces, black trousers and a nice blazer to go with it. He walked over held my hand and gave me a kiss.

"Ready babe?" I asked.

"Yeah lets go." and he ordered a taxi.

We walked to the lift, out through the reception and I've never felt so free in myself. I felt like a queen and I was with my king, no one could say anything to me because Mark wouldn't have allowed it. Who's going to pick a fight with him. With his arm around my waist we walked up to the taxi and he opened the door for me.

"I could get used to being treated like this Hun." I joked.

We drove 10 minutes down to the restaurant, we walked in and sat down. I ordered a white wine and just a light salad. I didn't want to be bloated on our big night out here and watching idiots make fools out of themselves on the karaoke later on.

"Kate, you know when we started speaking I always wanted to meet you, I knew we would get along. You're not a boyfriend, you just aren't, you're meant to please boyfriends. you're naturally submissive, I don't know why you're still worrying about your relationship with Lucy, she deserves a man, and you aren't it. You're a sissy. You're my sissy. I'll treat you like the girl you are, but let's not kid ourselves you love humiliation. So that's what you're going to get. I'm going to make you look and feel pathetic. Like you want to give it up and go back to your normal life. But you need to remember what I want and what I'm doing for you is best for you and me. I'll make you live the way of life you've always wanted whether you like it or not. But you will, of course you will, you're a sissy slut." he said.

I didn't know what to say, it was so nice but also fucking hot, my cage was twitching and i was wriggling my bum against the seat to move my plug. I had so many questions for mark and for Lucy.

"So what is the end goal here? does Lucy never want to see me again? at what point will she stop telling me what to do? do you want to see me officially?" I asked.

"There is no end goal here darling, you're on a journey. You have just taken a while to get here but I'm going to fast forward it for you. Lucy wants you to be the girl you are and experience the good and bad of that. As for me, I'm not sure you're exactly girlfriend material yet, you're very slutty, you've also already given your number out to another guy so lets see." said Mark.

We sat and ate our food over a candle lit dinner and drunk wine, i spoke about how my dressing started at 19, my first wig and make up at 20. How id never been with a guy before him but always cum to the thought of it when playing with myself. He knew all of my fantasies from our chats before we met. All over the top unrealistic fantasies of course, gangbangs, forced feminization with a bit of sploshing thrown in. He knew no matter how much i protested to things, deep down in my knickers he was making my cage twitch. After a couple of hours about 4 glasses of wine down I started to loosen up.

"Mark you're so handsome. Look at your muscles, you're like twice the size of me, I'm tiny, you could probably fit your hand around my arms. I've always dreamt of this, having a romantic meal with a hunk like you, here's me in my tight dress, done up like a tart with a butt plug up her bottom." we both laughed.

"That wont be the only thing up there tonight babe." Mark winked and i giggled.

"Ok lets make a move, this drag place opened an hour ago we can get good seats." Mark said.

"Yeah lets go, I actually can't wait, I love the lip sync battles in drag race, have you ever watched? it's so good!" I said.

We walked 2minutes up the road and we walked in.

"We have tickets and a table booked." Mark said to the doorman.

We followed him through the bar, we kept going and going until we got to the front.

"Nice seats babe, this will be great." I said excitedly.

An hour went by a there were some good and some bad crossdressers or drag queens up on stage, I was getting quite drunk at this stage and having a great night never the less.

The guy presenting the night walked up on stage.

"Ok guys how's the night been? well it's about to get a whole lot better because we have a surprise for someone out there tonight. It's her birthday and her partner has brought her here to spend it with us! He's said she isn't too bad with a mic in her hand either! So Katie and Mark where are you? Katie up you come!" he said. I couldn't believe it. I just froze.

"What? What have you done? Mark is this a joke? what have you done? I cant do this. Seriously I cant do this." I whispered. Mark let out a laugh.

"That's fine babe, I'll just text Lucy and let her know you're refusing and that way you don't have to go up. But all of your friends might be surprised to see pictures of you getting face fucked by me last night. I'll just message her now." he whispered back.

"No, stop! Ok fine. I'll do it." I said.

I stood up to wolf whistles, and slowly got up onto the stage.

"Happy birthday Katie! we've got a message from your friend Lucy here." the presenter said.

"Dear Katie, sorry I cant be there tonight but I've asked them to play your favourite song that you would always dress up and sing to in our front room, I think everyone deserves a chance to see that for themselves! Happy birthday Lucy." It wasn't even close to my birthday. I was shaking with nerves at this point while mark stood there smiling.

"Ok here it is, originally by Christina Aguilera, but tonight by Katie, it's Candy man, we've even got a couple of guys as back up dancers, out you come guys." I've always dreamt of this moment but now its hear I'm terrified.

The song started, and I started to sing candy man in front of a bar full of people. The two men danced behind me in their G strings, oiled up with 6 packs. One either side of me squashing me in the middle like a sissy sandwich. I started to grind on one of them, the alcohol definitely played a part. I tried my best in my most girly voice and rubbed the guys 6 packs while they squeezed my bum cheeks. The crowd cheered when I finished and I went and sat back down.