Caught Messaging Master Pt. 09

Monday came around and it was my first day back at work. I dressed in tight blue high waist jeans, some black vans and a plain white t-shirt. I painted my nails purple and had my hair down. I went for a less is more kind of look. I walked in, sat at my desk and said hello to everyone with a smile. I felt so much happier and comfortable with myself as Katie, I hated life as Alex. I dreaded work everyday and being in the same boring old clothes. The girls all seemed a lot more friendly to me, maybe they knew I wasn't trying to get into their knickers now, I would more than likely want to wear them instead. The guys who I used to speak to tried talking but it wasn't the same as before, they seemed reserved. My manager called me in and told me how happy he was that I'd been brave enough to make my decision, if only he knew I was actually forced to go through with this. I left work after having the best day I'd ever had at my job, I was happy with what I looked like and everyone's reaction to me. I even messaged Lucy to thank her.

I got home and changed into my lingerie, I put a black skirt over my stockings and a shiny silver blouse over my bra. I slipped a five inch dildo in my bum before I left. I added some glasses and put my hair into a bun to give the secretary look and I left the flat, I felt so sexy and I knew Mark would love it.

"Oh hey Katie." Becky said holding the rubbish bag.

"I thought I saw you get in from work earlier, you going back again?" she said.

"Yeah, I have another job. Like a part time thing you know?" I said.

"Dressed up like that? who needs a kinky secretary to start at 6 in the evening babe?" she laughed.

"Some guys just don't know when to rest right?" I said and started to walk down the stairs.

"Remember to come for a drink tomorrow night babe, I got the wine earlier!" said Becky.

"We'll see Becky. I'll let you know." I said.

I made my way to Marks office and got the lift up.

"Oh hello, your first day is today isn't it? Strange time to be starting, everyone will be leaving soon dear." said the woman at reception.

"Yeah I'm six until nine. Just a bit of tidying." I said with a smile.

"Katie come in." Mark said poking his head around the door. I stood up and walked into his office. He pulled the blinds down and locked the door.

"I've been waiting three days to fuck that little ass." he said. He walked over and sat on his chair and signalled for me to follow. I walked over to him swaying my hips and he pulled down his trousers and boxer shorts. I felt my dick twitch and pre cum start to come out.

"Suck it bitch." he said. I got onto my knees and sucked Marks dick. I'd missed it so much. My little cock was twitching again while he face fucked me. I got butterflies in my stomach when I had a hold of Marks dick. I sucked it so good, he sat there with his head back and eyes closed holding the back of my head. I loved being his bitch. He pulled me up and lifted my skirt up to my waist.

"Up you get." he said and slapped my bum. I sat on his lap in the cowgirl position facing Marks face and he pulled my dildo out then put his head on my hole. I let out and moan and put my fingers through his hair.

"Put it in Mark, quick." I said. He slowly pushed it in and my mouth opened in ecstasy. He put his hand around my throat and I was struggling to breath, my eyes opened wide.

"Bounce bitch." he said. I loved it. He made me so horny I would do anything for him. I started to bounce on his lap, his thighs slapping against my bum cheeks. He unbuttoned my blouse and pulled down my bra so my tits were out and shaking around. He pulled my skirt up and grabbed my hip with one hand and took my chastity cage in the other hand and squeezed. I let out a scream.

"Shut it bitch." he said and squeezed even harder. I bit my lip and put my forehand onto his shoulder. I started to bounced faster and harder, he now had both hands on my hips and my head flopped back and looked towards the ceiling. We heard a knocked on the door twice in a row.

"What?" Mark shouted.

"I'm just leaving." I woman said. I slowly moved my bum around in a circle motion. I started to kiss Mark and he came in that moment, I felt his load shoot up my bum and he trusted hard over and over while he pushed my hips down onto his dick.

"Mark? Are you ok?" the voice said again.

"Yeah, I'm just coming." he shouted back. I let out a little giggle and rocked on his semi erect cock until every drop was in me. He lifted me up and pulled my hair onto his dick. I licked the last remaining cum and he did his trousers up.

"Laptop is there, camera is there, you're here until nine tonight. Log off turn the laptop off and the lights." he said and he walked out of the room. I heard a knock a couple of minutes later as I was setting up the camera.

"Hey, come in." I said. It was the reception lady.

"I'm just leaving now Katie, if you need anything my number is on my desk. One more thing, a couple of buttons on your blouse have come undone darling. Don't let him take advantage darling." she said with her eyebrows raised.

"Thank you, goodnight." I said with a grin and she left. If only she knew how much I loved him taking advantage of me.

I set the camera up and logged into the account Lucy and Mark had set up just in time for six. I saw myself on webcam, I made my hair a bit more tidy and pushed my boobs up. I got the first message.

"Hi Sissy, I want your first tip to be from me your ex. So here's ten bucks. Reach into your draw and suck that dildo." Lucy had already logged on and was watching me. I reached into one of Marks draws and found a large pink dildo and started to suck it. I had about 50 viewers after an hour, they wanted me to pull my skirt up and touch my cage, one wanted me to fuck myself with my dildo while my cage swings in front of the camera. I had to take my stockings and heels off and show my feet to one guy. Another guy wanted me to twerk in front of the camera. A week ago I would've completely rejected the idea of Lucy making me do this but now it came as a second or even first nature. I felt at home making myself look and feel like a whore for her. One of the guys just wanted me to have a chat with him and tell him how much I wanted his huge dick in me and how much my cage would swing while he fucked me. It was all very basic stuff but it made me really horny. Harry still had the key to my device and I had no idea when the final film was going to be made so I could get it back. I made around 350 on my first night. I got a message from Lucy.

"Good work slut, keep that up and you'll pay off your debts in no time my muddy little pony." I closed the laptop and switched out the lights then made my way home.

I got upstairs and got my keys out, Becky's door opened.

"Hi, Katie, how was work?" she said.

"Oh, hi. It was fine thanks." I said and I walked in my door.

"Katie. I just wanted to say pop by around 7 tomorrow night, gives us both time to changed." she said.

"I don't know yet Becky, I'm really tired." I said. I don't know if I need to make anymore friends right now with everything that's going on. Although if I were a single man I would be in there like a shot, she's very attractive. Those days are behind me now though, I just crave Marks dick.

Becky walked across the hall and into my door way.

"You're so fucking hot." she whispered and started to kiss me. Her hands ran around my legs and up my skirt to my bum then around to my chastity. She started to push against my tits and my cock was trying its best to get hard. This is the first time I've even kissed a woman in a long time after mine and Lucy's love life died months ago. She squeezed my chastity and put her finger on my bum hole. She felt the dildo in me and gave it a little push then smirked at me as my eyes rolled back. I pushed my bum out and arched my back.

"Your body just naturally positions itself for oncoming dick now doesn't it? You have a think about it beautiful. If you're not too tired then give me a knock." she said as she walked back to her flat and shut the door. I shut my door and didn't know what to think. I can't get anything serious out of seeing Becky, I need a guy in my life and I'm into Mark, but at the same time she is hot and makes me quite horny.

I got up for work again the next day and wore a white jumpsuit with a pink cardigan. I looked quite cute with some three inch heels to go with it and made my way to work. I walked in saying hello to everyone with a smile as per usual.

"Katie, can I have a minute please?" my manager said. I got up and walked into his office.

"Take a seat Kate." he said.

"So, I have a question. Next week we had a plan to do a show for charity as part of a festival in the local park. We were hoping to raise a decent amount, we were going to do Grease. A few songs a bit of dancing and stuff." he said.

"Oh, ok. So would I just be a backing dancer or something?" I said.

"Well, as you know this is a mainly male office. Tracey was going to play the part of Sandy. Tracey went sick this morning with a broken arm." he said as he gave a hopeful smile.

"You want me to play Sandy? I'm not sure about this." I said.

"Well Katie you're my last hope, you're the only person left who can play the part." he shrugged his shoulders.

"I guess I'll have to cancel the show. By the way I have decided that my retirement will be coming up in two months time and I will be having a say in my successor in this position, I'll let head office know who I think would be the best candidate. At the moment it's out of you and Ronnie. You can go back to work now Katie, I need to phone and get this show cancelled." he said and he looked down to his mobile phone. I stuck my hand out and grabbed his phone.

"I've been thinking, I did always dream of playing Sandy when I was younger. Seeing as it's you asking, I think I will do it sir." I said with a smile.

"Are you sure Katie? I can cancel it if not." he said.

"No, I'm sure. Thank you." I said. He put his phone back on the desk and I left his office. I looked down at my phone and I had a message from Becky.

"Hi sweetheart, just wanted to remind you I'll be ready at seven this evening." I didn't know what to do. I don't really find the idea of a night with a woman that appealing anymore. I want to see Mark in all honesty but I wont see him until Wednesday night. I had another message.

"Hey Katie, it's Emma, the girl from the lift at the hotel. Me and my friend will be in London this weekend if you want to meet for that drink? x" I left it for the moment. I don't even know what's happening tomorrow.

I left work, got home and changed into a light pink satin dress covering one shoulder. I wore matching heels which showed off my toes and I wore a matching white silk bra and knickers underneath. I put my hair down and redid my make up. I coloured my eyebrows in and added some light pink lip gloss. I put in my big hoop ear rings and I walked over to Becky's for five to seven and knocked.

"Oh, you look absolutely stunning sweetheart." said Becky. She opened the door in a silk robe just long enough to cover her bum.

"You're showing me up here, I went for something a bit more comfortable." she said and I laughed. I walked into her living room which was dimly lit, a couple of candles around the room. Becky walked over and handed me a glass of wine. She walked over to the cabinet, bent over and kept her legs straight. She reached down for a bottle of wine and I got a full view of her bum and her G-string.

"Look at you Katie, such a stunning little thing." she said. She sat down next to me and I crossed my legs. She turned towards me and started to put her fingers through my hair and brush my cheek with her hand.

"Your make up is so good. You look like a model babe, you've got a great figure, especially that cute little bum of yours." She said.

"Look, Becky, you're a really attractive woman but I'm gay. I love getting fucked by men, I can't give you what you're looking for. I love cock, guys treat me like their bitch. You saw me covered in mud the other night. We just aren't going to match. I'm sorry." I said.

"Oh Katie, I can see why they treat you like a bitch. You're a little blonde bimbo aren't you. I know someone like you could never satisfy me sexually, look at yourself. I noticed when you looked at my bum just now you had to cross your sexy legs, are you telling me you didn't get a little thrill in your knickers just now thinking about if you was a real man and could fuck me? I have a boyfriend, he always takes control in the bedroom, I've never had a chance to do that myself, he's really into bondage, forcing me to do things he likes. Well when I saw you on the floor covered in mud looking pathetic I thought here's my chance to have a bit of fun myself. Let's face it babe, if you didn't like the look of me you wouldn't be sitting there on my sofa looking like a tart would you." she said. Becky climbed on top of me and started to snog me, our tongues touched and I started to feel my dick trying to get hard again. She mounted me and kissed me deeply.

"I love your pink lip-gloss babe, I want to see that face while you get fucked. I want to see that mouth wide open." She said. She took my hand and pulled me over to her table, I wobbled over in my heels.

"Becky, I'm not so sure." I said. she lifted my skirt and started to squeeze my chastity.

"Now it's time we fuck." she said with a big smile.

"Becky, I have a chastity device on. A guy I know is holding on to the key. I can't get it off." I said.

"I won't be able to fuck you Becky, maybe it's best I just leave." I said pulling the back of my dress down. Becky spun me around and started to rub my ass hole gently. I let out a moan, she kept rubbing as I slowly lowered further and further until I was bent over on her dining room table. She slipped one finger in and slowly started to move in and out for a few minutes before stopping.

"Turn over slut." she said.

"I'm sorry Becky, I have a boyfriend. I can't do this. I can't fuck with my dick in a cage either!" I said.

"I don't give a fuck about your boyfriend, what about mine?" Becky said.

"He's my master, I can't just sleep with anyone. I need his permission to do stuff like this Becky please." I protested. Becky walked towards me laying on my back on her kitchen table, she untied her robe and slipped it off. She stood naked in front of me, breasts out and wearing an eight inch thick purple strap on dildo. She starred at me with a huge smile. I sat up and she pushed me back onto my back.

"Don't try to fight it slut. I can see you want it." she said while putting lube over the head. She grabbed a hold of my legs and lifted them in the air. She pulled my knickers down to my ankles, pulled my chastity between my legs and pushed my legs together and held them over one of her shoulders. She started to push the head into my ass.

"Don't hold it in babe, show me how you feel!" she said excitedly. I closed my eyes and opened my mouth wide with a surprised expression on my face. I look back at Becky and she had a huge evil grin on her face. She slowly started to thrust in and out of my bum.

"Make noises like a real woman babe. Let me know you love it." she said laughing. I did as I was told and let out high pitched moans. She started to play with my cage which was through my thighs, I couldn't see it. All I could see was my legs in the air, closed together with nothing in-between.

"You like that slut? You like when I play with you dick? I don't ever want to see it out of this cage, I want to see you fucked like the whore you are." she said and I was getting more and more horny. She got into a real rhythm now and had hold of my hips pumping my bum hard, I started to really get into it and started to help the rhythm by moving backwards and forwards. Becky started to scream and I could feel the build up in my stomach again as my sissy orgasm approached.

"Oh look at that beautiful face all painted for me, you look like a real life doll. Does the big cock feel good? Does it darling? Cum for me beautiful. I want to see you cum from getting fucked by my huge dick sissy. Cum for me. Open your mouth wide and your eyes. I want to see how much you love it." she said. I started to breath heavy, rubbing my hips and pushing my tits together. I opened my mouth and turned my head to the side.

"That's it, touch yourself sissy. Show me your tits." she said. I pulled my dress down a bit and got my boobs out of my bra and Becky started to laugh. She leant over me and grabbed each boob while she fucked me. I screamed.

"I'm going to cum. I'm going to cum. Keep fucking my ass. I'm going to cum!!" I screamed. She gripped hard and laughed at me.

Suddenly we heard a knock on her front door and she stopped completely.

"Who's that?" I said.

"I don't know, I'm not expecting anyone." Becky said. She pulled out and I felt completely empty. She did her robe up and walked to the front door.

"Oh Gary, you never said you were coming." I heard Becky say from the corridor. I jumped to my feet and pulled my dress back down.

"Katie this is Gary my boyfriend. Katie just came over for a drink, she's just leaving actually." said Becky opening her eyes wide at me.

"Hey." said Gary as he looked me up and down.

"Hey, yeah I'm just leaving actually, nice to meet you." I said as tidying my hair and pulling my dress into position. I bent down to pick up my heels and walked out quickly with lube dripping from my bum.

I got into my front door and fell back against it and looked to the ceiling. I heard a light knock on my front door and I looked through the keyhole, Becky was standing there so I opened the door.

"Hey Kate, you left your bottle of wine on the table." she said loudly starring into my eyes, I looked behind her and her boyfriend was standing at her front door behind her. She handed me a bottle of wine and my knickers I must've left on the front room floor when I jumped up.

"Oh, yeah. Thanks for that Becky. Night." I said as I closed the door. I walked into my living room sat down and looked at my phone. I had a message from Mark.

"Sissy, tomorrow you will arrive at work in your brown trench coat. Underneath you'll be wearing a black steel bone corset and a black thong, nothing else. Thigh high black leather boots. See you at six." After what had just happened with Becky I was so horny already, now thinking about Mark I was ready to burst.

I got onto my bed and waxed my body from head to toe, I filed my nails then painted them a hot pink as well as my toenails. I had a long hot bath and relaxed before I smothered my body in a fake tan. I moisturised my legs and put on a facial while I laid and listened to some music on my sofa. My phone started to ring, it was Alex.

"Katie, Richard has given me the go ahead for the third part of your film, I'll pick you up Sunday evening around four. You'll need to be dressed in school uniform for this one. A parcel should be arriving tomorrow with your outfit in. See you Sunday babe." and he hung up before I could get a word in.

I left for work the next morning in a light blue summer dress and some brown sandals with a small bag on my shoulder. As I locked my front door Becky's opened and it was her boyfriend.

"Oh hi again, Katie was it?" he said.

"Yeah, that's right, hey." I said smiling.

"You seemed in a bit of a rush last night, was everything ok?" he asked.

"Oh, yeah, I just had a bit of work I needed to do that's all." I replied. We walked down the stairs together to the bus stop.

"Becky hasn't stopped talking about you, I didn't realise you were such good friends. I'm round hers again at the weekend, you're welcome to join us if you want?" he said.

"I'm busy sorry, maybe another time." I said, he is clearly clueless about what Becky is really into. I actually feel so bad for him, he has no idea I was getting fucked on the table he probably ate dinner from last night.