Caught Messaging Master

So, I'm a 25 year old average guy with a boring job and a girlfriend for the last five years. I've been crossdressing in my spare time since I was about 19 and my girlfriend is fine with it. We even occasionally do a bit of role play and talk about how we would love to get a real mans dick involved in our sex life, but it's all part of the act and we know that would never really happen. She probably would be totally against it, but while the role play is going on real life doesn't matter. Unfortunately, years of me dressing in private always makes me think about the next step, sex with a woman is good but it always feels like there is something missing. So I recently made a twitter account and began posting pictures of myself dressed up as Katie and got quite a big following, a lot of messages and an awful lot of dick pictures. Over the last few months I've also made a friendship with a guy called Mark. He likes to give me orders, makes me send him pictures in my lingerie and tells me what kind of outfits he would like to see me in.

As far as I'm concerned this is all make believe and it's not going to go any further than a twitter conversion. At the same time me and Mark do always say how fun it would be to spend a night in a hotel together as a couple, but as soon as I cum I usually stop thinking about wanting anything to do with a night like that. I had two weeks off work coming up and my girlfriend Lucy said she wanted to treat me. I'd always wanted to spend a prolonged period dressed up as Katie without having to change back the next day so she booked us a hotel away for a week.

"I've been thinking, since you don't get to be Katie so much lately I've booked us a hotel for a week. You can stay dressed the whole time, a proper girls week, facials, romantic films, waxing, anything." she said. I was so happy, its one of my biggest fantasies ever.

"I've also booked you in at my friends salon Friday evening, it's all paid for you're going to have literally everything done, head to toe! I've told her we are going for fancy dress to a work party so don't worry about it all!" Now that made me nervous. I'd never been outside dressed up before, but at the same time having a woman do my make up was another of my fantasies so I was in two minds.

"Listen, we turn up, you'll get all glammed up head to toe like a princess then I'll drive us to the hotel. Come on, it'll be incredible!" she said. It didn't take me too long to agree.

"Ok, sure." I said with a grin. I couldn't wait.

So Friday came around and we turned up at Lucy's friends salon after closing time.

"So, Lucy this must be your friend Katie." said her friend Steph.

"Yeah, this is her, she had a rough week and needs a lot of work done." we all laughed.

"Ok Katie, first things first, you need to be hairless if you want to win this fancy dress competition." said Steph.

"I'm afraid so, be careful with me Steph" I said. Steph then waxed me from the eyebrows down, I was so smooth it was unbelievable. It felt so sexy rubbing my legs together.

"Lucy I think you've got something to add now." Steph said with her eyebrows raised. Lucy went to the back and brought out two breast forms, I'd guess a C cup. Lucy smirked.

"These beauties will be glued to you darling, they will take quite an effort to get off." Steph put her finger to her lip with a confused expression.

"That's an interesting plan for someone off to a fancy dress party I have to say." They both looked at each other and laughed which was suspicious to say the least. I suspected maybe Lucy had let Steph into my secret which I wasn't too happy about.

"Ok, come with me darling." said Steph, pulling my arm into the next room.

"Time for your tan, you're going to look so sexy, I thought it's best to add your tits first, now they'll look so natural under your tan! Guys won't be able to tell they're stuck on this way, you'll look natural. I'll come and get you when you're done." She left the room. The next thing I know I'm standing naked completely smooth and golden. Lucy walked in and looked at me in shock.

"Oh my, Steph she's really coming along quick isn't she." she said.

"Lets keep this moving I cant wait to see the final look." Lucy took me to the next room and asked Steph for five minutes.

"Ok Katie we've only got a few minutes, you're going to cum for me and I'm putting your little pink chastity cage on you. I don't need you getting an erection over Steph dressing you, you're embarrassing enough just standing there like that. You look like a tart. She will know your little secret if you get a hard on." I agreed and tried to quickly cum. Lucy finished me off and took some of the cum on her fingers and lube up my ass. She pulled a plug from her bag and plugged my ass.

"You know you love it babe." she said as I opened my mouth and gasped. Lucy took my cock, she caged it shut firm and placed the key in her purse."

Ok babe, I've got you these pink satin knickers they'll cover your cage and the plug and I have a matching bra, quickly put them on." I pulled the pink knickers up over my bum and it felt so good over smooth skin. Lucy helped me with my bra.

"Now put these stockings on and this garter belt." I did as I was told and my dick started to press against the cage. I was started to really get excited thinking about what we might get up to in the hotel. Lucy looked so pleased with herself.

"Finally I have this corset for you so you have a nice hour glass figure." The corset was shinny pink too. I pulled the black stockings over my pink painted toe nails and attached them to my satin matching garter belt. I walked out of the room, to see Steph looking back.

"Oh my word Katie, your underwear is so sexy. I could eat you up." said Steph. Over the next hour I had false nails put on and painted pink, false eye lashes on and my eyebrows plucked. Steph placed a long blonde wig on my head. I hadn't seen Lucy this excited in months.

"Stick that to her head as well please Steph that'll be on for a while." she said.

"How long do you think that will stay on for Steph?" Lucy asked.

"Don't worry about her hair babe, Katie could be on all fours with a seven foot tall body builder behind her doing her doggy style while he pulls her hair with both hands and it still won't come off." she said. I don't know if she knew that turned me on but it definitely did. Steph then began to poke my lips.

"What's that?" I asked. There was silence for a few seconds, she did it a few more times.

"Don't worry darling it's just lip fillers." Steph said.

"Lip fillers?" How long do they last?" I started to raise my voice.

"Oh babe, you have long blonde hair stuck to your head, big bouncy tits, your eyebrows are arched like some hooker. So trust me when everyone sees what a slut you are I'm sure the lip fillers wont be the main concern." Lucy said shaking her head in disapproval.

"Everyone, what do you mean everyone?" I said. Lucy began taking pictures from all sorts of angles of me sitting in front of the mirror having my lips done. She played with her phone for a few minutes with no reply.

"Don't get your knickers in a twist Katie, you're all done now. I think Mark would love to see those big juicy lips around his cock." Lucy said.

"Oh definitely, don't let him cum over your face though and ruin your make up you little slut." said Steph. I was stunned.

"Mark? Who's mark?" I asked in a high pitch voice.

"God, I know you're a bimbo Katie but don't act thick with me, Mark is the guy you've been messaging behind my back and talking about how much you'd like to fuck him, suck his dick and the rest. Or do you deny it?" Lucy said.

"Lucy it's just an internet conversation it's not real." I said. Lucy put her finger on my lips.

"Quiet." she said. Lucy opened her eyes wide and looked into mine.

"This is how it's going to go slut, you've been cheating on me. I don't care if it's physical or mental or on social media, you've cheated babe. Now what do I do? You're sitting in front of me dressed like a slut and I have pictures on my phone. Shall I phone all your friends and get them here now? Or shall I phone your parents? Shall I take you to a gay bar and get you to dance? Shall I post your pictures on Facebook?" She looked towards Steph smiling.

"No, please Lucy none of those! Honestly I wouldn't cheat on you! Please." Lucy slapped me hard and squeezed my balls.

"Shut your mouth, you're pathetic, I don't know why I was even with you. This is what will happen, there's a pink vinyl pencil skirt over there and a black silk top, put them on, and the five inch heels on the floor. There's a fur coat on the door and your purse put them all on right now and say thank you to Steph." I got ready, I looked like a prostitute. I was caged, plugged and trying to walk in my heels.

"Thank you Steph" I said.

"No, hookers don't sound like that. Try again." said Steph.

"You're right Steph, say that again but in a girls voice Katie, you can do better than that. Put your hand on your hip and thank Steph. Stop embarrassing me." Lucy said to me furiously. I was so humiliated this point.

"Thank you Steph." I said again.

"That's ok Katie, now remember one hand on your hip, Wiggle your bum while you leave slut." said Steph and they both laughed. Lucy spanked my ass hard on the way out. I couldn't believe what I was hearing. I walked out as quick as I could in the heels and Lucy opened the car door for me. I sat down and my plug pushed in even more. I couldn't wait to get to the hotel room with Lucy so I could get this chastity device off and we could have sex, maybe even some pegging.

"Ok Katie, off to the hotel we go princess". I tried to make conversation with her all the way there but she never replied. I said how sorry I was but she didn't say one word. I started to feel like this might not be role play and Lucy was really angry at me. We got to the hotel and she made me go to reception as the room was under my name. We got in the lift and I tried to protest but the feeling of the stockings rubbing against my legs was too much to handle. The butt plug shifting with every step in my heels, my cock pressed against the cage and my tits bouncing with every step. I could really feel my lips getting bigger now. I saw myself in a mirror and looked sexy. I couldn't believe what I looked like but I wondered how long it would take my eyebrows to come back and my lips to go down. I only had 2 weeks off work! We got to the hotel door and I opened it.

"Ok slut this is where I leave you. I'll be outside in 4 days time to pick you up, check out is 11am Tuesday morning. If you leave to try to go home before or I get any news at all of any kind of trouble, the pictures will be up before you know it. Do exactly as you're told you stupid slut." Lucy gave me a soft punch to my cage and pushed me into my room. She closed the door and I slowly walked into the bedroom trying to figure out in my brain exactly what just happened. I heard the shower turn on in the bathroom and I panicked but I was stuck in this outfit and had no where to go. I opened the wardrobe to see if I could hide. When I opened to door I saw at least five or six different outfits in the wardrobe, a maids outfit, a latex cat suit, heels, bras, thongs, stockings, a dinner dress and more. Then the bathroom door opened, it was Mark. He looked me up and down, smiled and raised his eyebrows.

"Hey there beautiful, you're early." He stood there will just a towel around his waist, his hairy chest out and his six pack. He was all man and just like I imagined so many times before. I was shocked.

"What is going on?" I said. Mark slowly walked over to me.

"Don't worry babe, Lucy got in touch with me and explained how you've been a bad girl and needed a bit of a punishment, I was only glad to help." I couldn't believe it, I had never been in front of another man while dressed up, let alone plugged and caged, it was so humiliating. Mark pointed to the floor.

"Now, get on your knees bitch." I didn't know what to do. I'd never been with a guy, I had a girlfriend.

"Mark, wait one second." Mark grabbed me around the neck.

"Knees! Now!" I fell to my knees naturally and his towel dropped. His erection flew up in front of my face. I looked up at him.

"Open your mouth slut." he ordered. I opened wide and expected to have a dick placed on my plump lips but instead Mark spat into my mouth and shoved his fingers in.

"Now you know who is boss in here." he said. Mark held the back of my head and began to put his dick through my lips. I couldn't believe what was happening, he started to build the pace and began to face fuck me while I gargled, I was dribbling all down my tits as my eyes rolled back. Mark viciously grabbed my neck and pulled me up, he bent me over the bed and pulled up my skirt.

"Oh she plugged you too, well done Lucy." he said. I felt so humiliated and used but I loved it. He pulled out my plug and I felt his dick enter my ass, he fucked me so hard I was begging for more, his hands around my corset turned me on even more. It was the first time a real cock was in me and he was making sure I would never forget it. He pulled out and I was turned over. Before I knew it he had his knees either side of my tits and his dick over my face while he finished himself off. He pulled the back of my head.

"Swallow slut." I did exactly as I was told I swallowed every drop without thinking.

Four days to go.