Caught Messaging Master Pt. 05 - Monday

I woke up Monday morning and wiped my eyes. There was no sign of Mark, he must've already gone out. I got up and showered, I dried off and moisturised my legs, hair was starting to come through again. I needed to shave them again soon! I put on my bra and knickers and sat down. There was an envelope on the bedside table saying 'Monday'. Todays letter from Lucy I assumed.

"Hey Katie, only one more night to go! Lets make this one to remember right? I've heard you had a major break through. Your first sissy orgasm, doing that without touching yourself with a dick pounding is so cool. Well done! It's not been easy coming up with a plan for tonight after the last three. Your night with Mark and Billy is something hard to follow I must say. But I have had a good try. You are going back to Steph's this morning, I've asked her to give you a full body wax again, nails and lashes redone. You're having your second lip fillers and your hair restyled. I bet you cant wait! All of this is costing a lot so we will find a way for you to repay me. In the evening I've set up a meeting with a guy I know, it will become clearer when you arrive, don't be late. It's 6pm in the same bar you met your friend Stacey last night. Table 13. Tonight's entertainment, well Mark will handle that honey. xx"

Every time I got a message from Lucy I would get a sinking feeling in my stomach. It would drag me back to reality and away from this dream I was temporarily living in. A woman I used to tell I loved telling me how glad she is that I'm now able to cum while having a cock rammed in my ass was still as humiliating as anything that had come before.

Mark walked through the door and we had a quick kiss and talked about how great last night was.

"Now that you know you can cum without touching that tiny dick you know there's no need for it out any time soon!" Mark said.

He handed me a frilly yellow summer dress and some sandals. I put my hair into a bun and my boyfriend ordered me a taxi. I kissed him goodbye.

"You're spending the morning at Steph's Katie, Steph will have your outfit for this evenings meeting with Richard. Change there and go to the meeting, Steph will order you a cab from the salon. I will meet you there around 8." Mark said.

I knew my place and I didn't ask any more details, they would all be explained in my bimbo head when needed.

I arrived at the salon for half 12 and was greeted by Steph.

"Hey baby! Your whole mannerisms have changed! It's only been three days since I saw you last, you were acting like a spoilt brat, man in a dress. Now look at you! Walking with a swagger, wiggling that ass, holding your bag with a limp wrist, let me hear that sexy voice." Steph laughed.

"Do you really think so babe? I feel like a new woman. I can't believe it's only been three days. Honestly it's been a hell of a ride Hun!" I said in my best girls voice.

Steph had a huge smile on her face.

"Honestly Katie, I'm so happy for you. I could tell you wasn't happy before. Your body language. Look you're, what? 5'7? 5'8?, you're slim, size 8, small feet, small hands and you're super submissive. You belong in a dress. I was telling Lucy for years to ditch you I have to say! I've heard some rumours through the grape vine, are they true?" she said.

she grabbed my hand and pulled me into the back.

"Ok strip off girl, let's see the damage. Tell me all about your weekend." she said.

"What have you heard?" I said, I stripped down to my bra and knickers.

"Keep going, I need you completely naked. Don't worry about me, I'm not interested in sissys. Plus you're only interested in hunks with massive cocks. I haven't got one of those babe. I heard you might've seen Lucy with Mark Friday? I also heard you almost drowned in two guys fluids saturday night. I said it before girl, you had that coming." Steph said. I took off all of my clothes and stood naked.

"That doesn't sound too far from the truth. Honestly, I think I nearly passed out from the amount of times they fucked me. My mouth, my ass, hand jobs, blow jobs, face fucking, spanking, I laid on the bed while they unloaded on my face for like 4 hours. I'm not kidding. It was so humiliating babe." I said.

Steph burst out laughing, "Fuck Katie, I'm a little bit jealous!" she said.

Steph decided it was best to remove my hair and my boobs and start from scratch. Especially after finding out I was pissed over Saturday night. First she gave me a full body wax so I was silky smooth again. Next she glued my new tits, this time size Ds, and for a girl 5'8, they were heavy. I went for a spray tan next and came out looking like I'd be away on holiday for the week. Next came my new hair, again using a glue. This time I was a brunette, which suited me more. She glued French tip toe nails and new finger nails. I needed a touch up on my face too, I had a facial done followed by my eyebrows plucked, new long lashes put on. My New 14cm gold hoops in my ears and finally my second dose of lip fillers.

"Ok, lay down, I have a final instruction from Lucy." Steph came back with gaffer tape, she pulled my chastity cage into my gooch, tight. She stuck it into position.

"Ok, that wont be moving for a while." She said.

She got me to stand up and step into shiny vinyl hot pants. She told me to bend over and she inserted what felt like a 5" butt plug into me. She pulled them all the way up. Then up some more. I felt like my cage might've disappeared into my body. She zipped the hot pants up and there was no sign of a bulge below. Next she helped me put a corset on, she tied the back lace up so tight I could hardly breath, my stomach was pulled so far in I looked like a Barbie doll. She handed me nude stockings and a black garter belt. My tits were bursting out of my corset, I looked like my dream girl, if I swung that way. I could hardly bend so Steph made me step into a skirt and she pulled it up, it was a long satin pencil skirt going just past my knees. Next was a satin silver blouse with long sleeves. I stepped into my 5inch black shinny stiletto heels.

"Absolutely perfect! You are such a doll Katie, Mark will cum in his pants when he sees you." Steph said and I started to get horny just seeing myself and thinking of Mark touching me later.

I couldn't help but get excited to see how I looked. She sat me down and added my foundation, a dark red lip stick, eye liner and eye shadow. She straightened my hair and I was taken to the mirror.

I almost started to get tears in my eyes.

"I can't believe it." I said.

"Go get them girl! You look fucking hot, I'm not kidding you look like a office girl who guys would be dying to get some overtime with. You look like a boss!" Steph said.

She ordered me a taxi and I couldn't thank her enough. I left at half 5 and made it to the bar a little early. I sat and had a couple of wines while waiting.

"Good evening young woman." a man said approaching my table.

He must've been late 40s, a bit of a silver fox, tall, well built but looked like a business man.

"So you're interested in a bit of work, do you mind if you give me a quick twirl? he said in a posh voice.

I stood and turned around in a circle.

"Sorry can I ask what the kind of work would be?" I said.

"Well seeing as we've had a conversation over email explaining the kinds of movies we make I'm assuming you mean genre's or story's? Well you would be put in the crossdressing/sissy category which is growing all the time. You're a fine specimen I can see, I'm sure we could find a lot for you. You're petit, nice legs, very feminine facial features, good posture and most importantly great bum and boobs." he said very seriously.

"You want me to be in a movie about a crossdresser?" I said in shock. What has Lucy set up here? Making me privately meet guys in a hotel for a weekend is one thing but I'm now sitting talking about being in a movie? Has she lost her mind?

"No. I dont want you in a crossdressing movie, I think you're more suited to the sissy side of things, maid outfits, flight attendants, nurses, that sort of thing." he said with no expression at all. I couldn't get my head around the situation.

"I don't really know what to say to be honest Richard. I'm a little lost for words at the moment." I said.

"Well listen Katie, most of this is sorted anyway, we already agreed on the money and the amount of dates. That's not a problem, obviously as we agreed the first one will be tomorrow evening, you'll need to bring the latex black catsuit with you that we spoke about before. Make sure it has a crotch zipper!" he said pointing down towards my dick. I got a little thrill out of nowhere which was a suprise seeing as he was so serious.

Lucy has organised for me to be in sissy porn. I now need to speak to her, anyone could see this. I can't go through with this.

"Ok richard, so I will try and message you tonight and confirm everything. Thank you so much for this opportunity!" I said with a smile

while thinking I need to speak to Lucy right away and get this stopped.

"I look forward to hearing from you." Richard leant over and kissed me on the cheek and left.

Mark arrived 20minutes later.

"I'm going to be in porn? Me?! In porn?! Are you fucking kidding me?! I cant believe you never told me this. This is too far Mark, I need to speak to Lucy now." I said angrily.

Mark sat down and calmly said

"A step too far for who? A sissy who takes cocks up the ass every day, cum in every hole and dances in front of a bar full of people? Katie, it's always one step forward and two back with you isn't it. Your little bimbo brain just doesn't have the capacity for so much info does it? You are a sissy slut. That's all you are, that's your life now and if Lucy doesn't force that to happen then I will. You want to speak to Lucy? Ok here you go." he said. Mark handed me the phone and I starred at him. I picked it up and phoned her

"Lucy, hi. I've just met that Richard guy. I can't be in porn Lucy, people could see it, I could never live that down. I can't do it." I said.

"Listen to me slut, I'm only going to say this once, you started this. You cheated on me. Did you stop to worry how I would live down my ex boyfriend being a sissy messaging men? I have pictures and videos of you getting fucked hard. I have let you live your dream over the last three nights because you are too pathetic to have done it yourself. How much do you think all these make overs and outfits come to? How could you be so ungrateful? I have agreed with Richard you are taking part in a three part film trilogy. The money from that will cover your weekend. If you don't do it then you'll repay me by having emails sent to everyone you know with a video of you begging to have two cocks slammed into you. Your choice." Lucy hung up the phone.

I put my head into my hands.

"Listen babe, this is the final step, then you're out of each others lives. We are going to enjoy tonight, then tomorrow you're going to be in a porn film. That's the way it's going to go. Your body should be seen by others, you're too hot to keep to myself." he said.

We stayed and had 3 or 4 drinks before mark took me onto the next bar, we went to a little place in Soho, just a doorway no signs up. We walked downstairs and saw about 25 people at most in there, quite quiet music and dimly lit. My brain feared the worst, everyone looked around as I walked down stairs in my blouse and pencil skirt. We sat at the bar a got to know a few of the regulars.

"If you're looking for a bit more fun, there's a room just through there on the left, you might enjoy that. You look like a good time girl." One guy said, he was there with another crossdresser, both mid 30s.

Mark walked me down the corridor and we entered what can only be described as a dungeon. A woman called Nancy stood there in full latex with a naked guy bent over in some stocks, she whipped him over and over, his ass was drawing blood. There was a group of about 6 people watching and cheering while he screamed in pain. At the same time I could see his erection poking out.

"Do you want a go?" Mark whispered to me.

"Yeah that looks fun to be honest." I said.

"Excuse me, could my sissy have the pleasure of being next?" he said.

She looked me up and down with a grin and nodded. She unlocked the guy and shoved him onto the floor in a corner.

"Sorry I thought you meant I could have a go with the whip to hit that guys bum? I said.

"Get your fucking clothes off slut! Listen to the way this one speaks, you talk like a timid little sissy it's pathetic." Nancy replied.

I looked at Mark and he was laughing. I knew that this was no laughing matter, I don't get turned on by pain and I dont want to have blood on my perfect bum when I'm in porn tomorrow. I didn't know what to do, I started to take my blouse off and unzipped my skirt.

I stood there in my vinyl hot pants, stockings and a corset. Nancy ordered me to bend over and get into the stocks. I hesitated.

"I can't really bend in these shorts Ms, I have my chastity cage stuck between my thighs." I said in a sad voice.

Nancy, with her knee length black leather boots kicked me hard in the crotch, I screamed and bent at the waist.

She lifted me up, bent me over and locked the stocks. I was stuck with my hands either side of my head with nowhere to go.

"Ok, what shall we do to her guys?" Nancy asked.

More people started to walk in, I'm guessing my screams must've caught some attention.

"Look at those lips, I want those round my dick!" one said.

"whip her ass Nancy!" one shouted.

"Yeah whip her ass." said another.

Nancy walked in front of me and placed a latex gimp mask over my head and put a ball gag in my mouth.

"Lets see if the little slut complains now yeah?" every started laughing.

Then it started, Nancy whipped my ass over and over, I screamed into my gag. Dribbling everywhere.

"Shut it bitch no more noise!" she said.

She whipped me again and I let out another scream.

Nancy kicked my feet apart and gave a hard punt into my crotch to which I gave another scream. She came and took my gag off and pulled me mask off.

"We will want to see her face for the next part." Nancy said. She walked off and came back in.

"Oh fuck, I haven't seen one that big before!" I heard Everyone started laughing then cheering. I felt the head of a dildo slapping my bum as she danced behind me entertaining everyone.

"This is my latest purchase guys, 14 inches long, look how thick it is! This bitch is taking it all if it takes all night!" everyone cheered.

"Please Nancy no, I cant fit 14 inches in my bum!" I shouted. Just hearing myself say that sentence was humiliating but also turned me on more.

She unzipped my hot pants and slid them down, she pulled out my butt plug.

"Oh slutty girl was already plugged for me." she said.

She rested the head of her dick on my hole and kept teasing going in. she slowly started to push further and further until it turned into a hard-core fuck. She got into a real rhythm, she held my hips by the corset. My tits were swinging backwards and forwards.

She fucked my ass for so long, wiggling her hips making my hole wider and wider while spanking my ass.

"We're half way there girl, 7 inches in. Someone get me a drink, whoever does gets their dick sucked." she shouted.

One guy quickly ran to the bar and brought Nancy a drink over, she pointed at my head and she gave me a hard thrust. My mouth flew open and his dick slammed in my mouth. It was Saturday night all over again, I was being fucked from both sides except this time I had a monster in my ass. He fucked my mouth then dug his fingers into my head and forced his whole cock down my throat before filling my mouth with cum. He left his cock in my mouth so I could only breath through my nose, I was forced to swallow just to keep breathing. Next came a girl in her late 20s, I'd say a size 12 or 14, she stood in front of me and turned around, she bent over, pulled her thong down and spread her legs. She pushed her ass back into my face. I was being smothered, her hands came back and pulled my head in while she pushed back.

"Eat my ass you little bitch!" she shouted.

I started to lick her ass, she wiggled into my face over and over while I had my tongue in her, she let out moans before her partner came and started to finger her. They kissed while he fingered her and I ate her ass until she came.

Nancy carried on fucked me while shouting out every time we went a further inch in my bottom. I was made to suck 5 different dicks and eat another girls ass before Nancy rammed her 14 inches in me and completely breaking me. Everyone cheered and Nancy got a friend to get a picture of me bent over in the stocks with her standing behind me.

She pulled out and unlocked me, everyone walked back into the bar. Mark pulled my pants up and pulled my skirt up. I put my blouse back on and tried to stand but my knees were shaking. I couldn't sit because my bum had just been hammered. I sorted my hair out and wiped my mouth, Mark held me around the waist and we walked through the bar.

"Oh she's got the jelly legs!! Nancy has done it again." someone shouted and everyone laughed.

"She wont need another dick in a while!" another shouted.

"Hey slut, anytime you feel like coming in here and getting mouthy with me again I'll fuck your brains out anytime. You've got a nice peachy bum darling." Nancy said.

I put my head down and we left, we got into a taxi and back to the hotel. It was good practice for my final day Tuesday.