14 Day Mistress - Pt. 05

Day 10

I woke up the next morning so excited to see Stephanie. We had been left in the dressing room to change back into normal clothes. At first, I had been worried that she would be disappointed when she saw me undress and turn back into Chasen. To my surprise, she was anything but disappointed.

As she helped me undress and pulled off my mask, she smiled sweetly "well that's a pleasant surprise" she said and leaned up to give me a playful but deep kiss.

I was also a little surprised to find out that she was not trans. Her beautiful pussy was lasered smooth and had the sexiest lips that dangled in the backlight as I watched her pull on her jeans. That image was burned into my brain as I showered and thought about our scheduled lunch.

Slightly before noon I pulled up to Chateau Marmont. Walking up to the hostess stand, I realized I didn't have anything more than her first name. Going with what I had, I gave the hostess my name and said that I was meeting Stephanie for lunch.

Without missing a beat, she simply said, "Yes Mr. Chasen, please follow me" and led me into a semi-private area where Stephanie sat alone at a large booth like table.

Stephanie stood up to great me with a warm hug, "my love, so great to see you." "Come sit next to me" she directed.

We spent the next hour talking and snacking. It was so amazing to talk to her openly about my experiences over the last 7 days. We laughed and relished each other's stories. She definitely had some good ones. She was essentially the sex slave of her boss in a crazy two life situation. She worked for a female owned private equity company, but the owner just happened to be girly voice. Apparently, her name was Ellie and a year ago they accidentally met at a private club where Ellie completely possessed her. It was a sexy and incredibly captivating story. As the conversation progressed, we talked about how much we enjoyed being controlled by our mistresses.

As the table was being cleared, she leaned into me and whispered, "can I trust that you enjoy cum as much as I do."

I smiled and said, "maybe more."

She giggled "you may be wondering why we are sitting at such a large table by ourselves."

I looked at her in anticipation as she filled me in "Every Tuesday, Ellie arranges for a lunch for many of her clients and prospects. The lunches have become legendary in the finance world and are a very desired invite."

Not putting it together, I just stared at her waiting for some explanation. She continued "Setting aside the incredible financial transactions that take place at the meeting, I've secretly been a big part of their success."

"Secretly" I questioned.

She laughed "before everyone gets here every week, I take position under the table and throughout the lunch, I service every person at the table. It's quite a challenge to finish with all of them before lunch is over. A wonderful challenge, but it's hard work."

As she said this last part, she slid her hand under the table and ran her fingers up to my rock-hard cock.

Laughing she said "you do love cum as much as I do. Do you want to be me today?" she asked coyly.

"Won't they know" I said.

"Absolutely not. None of them know my identity and the unwritten rule is that they aren't allowed to look under the tablecloth." She replied.

My heart was pounding with anticipation when the hostess approached our table and informed Stephanie "Your first guests are arriving, Miss Stephanie."

"Time to disappear my love..." she said.

I didn't even hesitate, I slid onto the booth, lifted the tablecloth and climbed underneath. It was surprisingly spacious, and the carpet flooring was quite comfortable. But it was completely dark as the thick tablecloth hung all the way to the ground. I could see a slight crack of light where Stephanie's cute toes stuck under the tablecloth at the head of the table. Not long after I had disappeared, I heard a multitude of voices above. They seemed to all be talking with some introductions before they sat down. Then I heard the girly voice of Miss Ellie.

"Please everyone, take your seats" she said as I watched shoes work their way around the table.

Then a funny thing happened. I heard zippers from all angles and the clear sound of pants being pulled down. I watched as the tablecloth was pulled up directly to the right of Miss Ellies stiletto boots. It was pulled up and over a relatively large and flaccid exposed cock hanging between widely spread bare legs. I wish I could properly explain the way my heart was beating and how light-headed I became just anticipating the first touch.

I crawled toward my way toward my target and felt my mouth watering. Without using my hands, I took the underside tip of the hanging cock on my tongue and directed the head to my lips. I sucked slightly to pull the whole bulbous head into my mouth. Letting my mouth water around it, I slowly lubricated the now growing shaft. Inch by inch, I worked my mouth down until the entire cock was in my mouth with the head touching the back of my throat. I left it there, not moving at all, I could feel it growing slowly.

As it grew harder, the head pushed slowly down my throat. It wasn't thick, so it slid down easily. It grew and grew until it was at least three inches into my throat cutting off my breathing. I used my throat muscles and tongue to massage it softly without taking even an inch out of my mouth. I knew I didn't have much time before I would need to take a breath, and I was hoping I could accomplish my goal before my first breath. Ambitious I knew, but I felt the absolute desire in this cock and thought it might be possible. I pushed my head into his crotch, moving his cock in and out of my throat no more than an inch either way.

Keeping a steady, but not too fast, pace, I kept this up for over a minute when a soft bump on the table above my head was followed with the rapid pulsing along my tongue that I had been working for. Leaving him inches down my throat, I slowed my movements and enjoyed his pulsing flow of extasy pour directly into me. His pulsing slowly subsided and I let him slide very slowly from my mouth so that I could ensure the cock that I left him with was empty and clean.

Shortly after I removed him, he moved the tablecloth back over his shrinking cock and let it fall to the floor. Seconds later, the tablecloth next to him was pulled up exposing an already hard uncut and fat unit waiting for me. I was aware of the table ordering food somewhere above me as I used my wet lips to move the foreskin back over the thick head and welcome the cock into my mouth. This one was not too long but was very thick and I was sure it wasn't going down my throat.

I could barely open my mouth wide enough to protect if from my teeth. I'd have to work a little harder to finish the job here. I decided to use some firm suction here to create a tight seal around his fat head. I sucked hard as I brought his thick shaft in and out of my mouth. I bobbed my head back and forth as I worked hard to coax him to climax. It seemed to take forever as sweat beaded on my forehead and I felt my jaw aching.

I began to think I would need to come up with a different technique when he unexpectedly exploded. And I mean exploded. Hard, hard spurts of cum splashed the back of my throat and top of my mouth. It poured all through my mouth as wave after wave pelted me. I swallowed as fast as I could but gagged as it overwhelmed me, and I had to pull away from the thick cock. The last hard spurt splashed onto my nose and cheek. I reached up quickly and grabbed it softly with my hand while I regrouped. Quickly I regained composure and locked my lips back onto his tip and softly milked the last drops out of him.

As I pulled away, I felt the tablecloth begin to rise next to him. I pulled back and shifted to the next guest. To my surprise, I recognized the heels skirt of Stephanie. Her panties were nowhere to be seen. Her legs were spread, and her body shifted so that her pussy was fully exposed. I locked on immediately, taking her firmly against my open mouth and pressing my tongue against the top of her already wet entry. I moved my mouth slowly up and down, massaging her clitoris with short steady strokes.

I continued the motion for quite some time before I felt her body begin to move slightly in sync with me. It seemed like her entire pussy opened up to me, enveloping my chin. I began to insert my tongue further inside on each downward stroke, pulling it from inside and running it further along her hardened button on every upward movement. I wondered at one point how I would know when she came without the normal vocal cues. I needn't worry. With one smooth motion, her heels wrapped up onto my back and her thighs closed tightly around my head.

I fell awkwardly into her as I struggled to continue my motion, desperate not to interrupt the tempo. Within seconds, she began to shudder and squeeze my head firmly. Fluids poured from her, coating my face and flooding into my open mouth. I slowed my contact as she held me tight for a good 30 seconds before she subsided. Her legs unwrapped and she scooted back up to sit properly in the booth. As she pushed the tablecloth over her legs, I felt her hand reach under and softly brush my cheek. I rocked back on my heels and took a deep breath while wiping my face with my hands.

As I progressed through cock after cock, I became aware that I would eventually get to Miss Ellie. I wondered if she would be partaking in my services. I mean she was absolutely beautiful. But for some reason, I couldn't picture her ever losing control in any form in front of her clientele. But my curiosity as I got closer was growing out of control. When I was one person away, I completely lost concentration staring at the tips of her high heel boots poking under the tablecloth. Above me, I heard the plating of deserts, and my anticipation quickly grew. Looking to my right, I moved quickly onto the semi-soft cock peeking out from under the tablecloth. To my absolute thrill, my impediment finished in less than a minute.

Wiping my mouth, I moved quickly until my head was above her boot tips. When the tablecloth finally rose, I was stunned by what had to be a 10 inch oddly thin cock staring me in the face. Miss Ellie was trans. I couldn't freaking believe it. Despite my many recent interactions with the community, I never suspected. Through the film of cum already coating my throat, I swallowed hard as I knew that this monster would have no problem moving deep down my throat. I shivered with anticipation.

My mouth already well lubricated, I endeavored to take the whole thing in one motion. I got a little more than halfway down his hard shaft when I felt like it just couldn't go any further. It was in my throat, but I couldn't force it down no matter how hard it tried. I resolved to doing what I could and moved back and forth slowly on the top half. Without warning, a hand wrapped tightly into my hair. That hand forced me with surprising strength all the way down on her cock.

When the head got to the previous stopping point, there was a short pause before it literally popped through. My mouth plunged immediately down to her hairless stomach. The long cock dove down my throat. It was an unnatural feeling having something that far into me. I was fully impaled. Miss Ellie's firm grip made it clear that I wasn't going anywhere. She held on so tight it hurt as she rocked my head back and forth without letting so much as an inch of movement. The feeling of it so deep inside me was exquisite. She rocked my back and forth for what seemed like an eternity. All the while, I had no chance to breathe. But honestly, I didn't care. I wasn't leaving until she finished.

As she neared the end, her motion stopped and her grip in my hair tightened. I could feel her convulsing from my mouth to what felt like my intestines. I was oddly aware of her speaking to the group above as she poured directly into my stomach. Even after she was finished, she held my head onto her until she began to shrink inside my mouth.

I didn't dare move despite the now panicky feeling running through my body. I was desperate for air. When finally, she let go, I collapsed back under the table quietly gasping for air. I lie there for a good 15 minutes as the table dispersed just thinking about what just happened. Finally, a few minutes after everyone was gone, I moved to crawl out. The bus boy who was cleaning the table didn't even acknowledge me.

Day 11.

The morning came too early the next day. And to be honest, I was pretty worn out. Maybe I had grown numb to the absolute debauchery, but I didn't have that nervous pit in my stomach. I wasn't anticipating some shocking act. Instead, I was anticipating it. When I arrived at the office, there was a package awaiting me. Wondering back to my office for privacy, I opened it.

Inside was a note that read "Today you will do a practice run at the address below at 12:30. You will need to plan for a last-minute business trip to Vancouver for two nights leaving tomorrow. More details to follow." Well, this was going to be interesting. It wasn't too hard to come up with a story for the office as I had multiple clients in Vancouver. My wife, on the other hand, was going to be more difficult.

The address on the card was nearby and I arrived about 5 minutes early. I was clearly a beauty salon of some sort. But it appeared that I was the only client.

A beautiful woman greeted me "Welcome Chastity. I'm Gia. I'll be your guide today. I hate to say this, but please hold all your questions until the end. It is a process where the end-result is all that matters. I can't wait to get started. Follow me please."

She led me back to a beautiful bathing facility and directed me to remove all my clothes. I did as I was told and followed her into a large shower room where several men and women were waiting for me. The next hour was spent bathing, scrubbing and plucking until it felt like every hair was removed from my body. My skin was super sensitive as I was lowered into a warm bath and bathed. In the back of my mind was a kernel of fear that my wife would discover my sudden lack of hair and get quite suspicious. But somehow, that rational fear passed right through me. I would come up with some excuse. I just couldn't think of one right now.

When I finally rose from the bath, a young man put a fluffy robe on me and led me into what I can only describe as hair and makeup. As I reclined with my eyes closed, multiple women began to work on me on all ends. I was getting a pedicure, manicure and facial. The facial turned into a series of makeup artists working in succession. I'd love to give details on what they were doing, but honestly, I had no idea. But I understood they were making me look feminine. I just lay there for what had to have been close to 45 minutes.

When makeup finished and I my chair was brought forward, I was looking forward to seeing myself in the mirror. But there was no mirror. Looking around I realized there were no mirrors anywhere. The team begin fitting me with a dark brown wig that gave me straight hair down to my upper back. The wig was exquisite. It felt like real hair as it brushed across my neck and cheeks. Gia suddenly appeared in front of me with a big smile on her face.

"Beautiful" she exclaimed "absolutely perfect." "

Come with me," she directed and held out her hand.

We walked into an amazing closet full of some of the sexiest looking outfits I had seen in quite a while. Removing my robe, Gia held out a beautiful pair of thong panties. I stepped into them, and she pulled them up from behind me. Reaching between my legs from behind, she grabbed the head of my cock and pulled it back. She then guided my balls up into my abdomen and secured the whole thing by pulling the panties up into place. They were tight but felt amazingly sensual.

The first outfit started with dark black thigh high stockings, coming up to a garter belt. She guided me into an elegant but tight leather skirt. Gia fitted me with a tight bra with breast forms already inside. Over the bra was a tight long-sleeve, partially sheer top that clung to my body and went all the way up into a mock turtleneck. Over that, she fitted me with a sexy leather corset that came up over my new breasts. The outfit was topped off with a pair of sexy black high heel leather boots that zipped up in the back. Stepping back, she admired her work. She poked and prodded a little; pulling things into place here and there. Then said with an heir of satisfaction "Perfection." She held out that same hand and guided me out of the dressing room.

I had a little trouble walking in the heels at first, but instinct took over and I quickly fell back into it. We walked out into the main room where the whole team was waiting. They all clapped and cheered. All of this was funny because I could only see my body looking down. And admittedly, it looked amazing. Gia walked over and rotated around the large painting that sat on the far wall to reveal a huge mirror. I was stunned. Absolutely stunned. I looked nothing like myself. I felt my tucked in cock pushing hard against the tight fabric. I was so damn hot. I wanted to fuck myself. How did they do this? It made no sense.

Gia interrupted my revelry and said, "Nathan here is going to take you down the street for a drink at the Montage."

I felt a panic feeling from my core to my cheeks and looked quickly over to her. She smiled and gently directed me back to the mirror. My fear slightly subsided. Nathan came up to me, grabbed me by the hand and gave me a sweet kiss on the lips. He had to be 6'4 and was a true specimine. Though I don't find men attractive, he was definitely very appealing. Hand in hand, we walked out the front door. Looking down the sidewalk to the Montage entrance, I was terrified. Nathan gripped my had tightly to give me reassurance.

There were people walking on the sidewalk. I was turning heads as we moved toward our destination. It seemed at first like everyone was staring at me. Like they could see right through me. Like they knew that I was in disguise.

Just as I was letting my head spin with my imposter nightmares, Nathan whispered "walking with you is definitely good for my ego."

It's funny, just those simple words gave me confidence. Suddenly I realized that people were looking at me in a different way. They looked at me the way I looked at a sexy woman walking down the street. Before I knew it, we were at the front door of the Montage.

The doorman smiled as he looked me up and down then reached for the door and, without hesitation, said "Welcome to the Montage mam."

I nodded, too terrified to speak. Nathan directed us through the lobby and into a beautiful bar. The bar was not terribly crowded but was definitely active. We found two seats at the end of the bar and Nathan ordered two glasses of wine.

Nervous to talk, I whispered in the most feminine voice I could muster "thank you."

He laughed "your voice isn't that bad. I was expecting James Earl Jones from how scared you have been to use it."

I laughed "I'll have to work on it."

"It won't take much" he replied, "and your looks will allow you to get away with having a slightly masculine voice."

Nathan had a way of making me relax as we chatted. Before I knew it, I was three glasses in and had quite a buzz going.

Nathan looked at me coyly as he rested his hand on my thigh "did you know that Eden has a penthouse apartment on the top floor here?"

"Is that a proposal" I laughed.

"It definitely is" he smirked "let me text her and see if we can borrow it."

"I don't know" I began "I don't think I'm ready for that."

He cut me off "there is now way you are going to get away from using that body."

Who was I kidding; I wanted so badly to use this gorgeous body. I smiled as he paid the bill and guided me to the elevator. When the elevator doors closed, he pulled me in close to him and kissed me so deeply.

We weren't three feet inside the apartment before Nathan's hands were all over me. He had me pressed up against the hallway wall with my hands pinned above my head. I could feel his hard cock pressing against my abdomen. Freeing my hands, I turned him around and pushed his back against the wall. Dropping to my knees, I slowly freed his straining member from his jeans. It was gorgeous. Holding it in my hands, I looked up to find him staring down at me with total passion. I parted my red lips and guided the head of his swollen cock into my mouth.

Over the last 8 days I had been used and abused and I loved every minute of it. But this time seemed intimate. He softly held the sides of my face as I guided him down my throat. He slowly and passionately fucked my face. He was so hard inside my mouth. I could hear him moan softly. Just when I thought he was getting close, he pulled out. I looked up into his eyes as he lifted me from my kneeling position. He kissed me again and again. Soft moans coming from both of us. He parted from me and walked me over to the bed and sat me down on the edge. Reaching up under my skirt, he wrapped his fingers into my panties and pulled them down over my boots. I scooted myself back further onto the bed as he took off his shirt and let his pants fall to the floor.

He crawled onto the bed between my legs and kissed me firmly. I lifted my knees up high and arched my back as I welcomed his hard cock inside me. I'm not sure when he lubed himself, but his cock slid smoothly inside me. I rested the heels of my boots on his lower back as I wrapped myself around him. We kissed constantly as he slowly rocked me back and forth; fucking more sensually than I knew was possible. We were locked together in the same position when I felt his strokes intensify.

"Please" I whispered as ran my fingernails down his back.

The kissing stopped as he neared climax, but our open lips stayed slightly touching.

"Thank you baby," he moaned as the entire weight of his body pushed his cock deep into my bowels.

Holding it there and rocking our bodies, he poured wave after wave into me. As his orgasm subsided, he lay his body down onto mine. Our bodies slowly relaxed and his softening cock finally left me. My legs collapsed onto the bed. Nathan pulled up onto his elbows and gave me a passionate kiss.

He whispered, "I better get you back."

As he peeled off of me, he reached down and grabbed my panties. He sweetly put them back on me, tucking me in just like Gia had done. I stood up and he helped me straighten up; pulling lip gloss out of his pocket and helping me apply it. As we walked toward the elevator, we laughed and chatted. Halfway down, the door opened, and an older couple stepped inside.

The woman looked at us and said loudly, "what a beautiful couple you are."

I smiled and Nathan said, "thank you."

Just then I felt a warm we sensation flow out of me. I squeezed Nathan's hand and looked down. He seemed to know exactly what I was talking about as he leaned back and looked at my ass. Luckily the couple was facing forward and hadn't noticed. To my absolute shock, Nathan reached his hand down under my skirt and ran it up the back of my leg all the way to my ass, scooping up the cum that had poured out of me. I could see the now clear liquid pooled in his palm and glistening on his fingers. I took his hand to my mouth and guided the entire load into my mouth. I brought his soaked fingers into my mouth, cleaning them completely. In my ecstasy, I had closed my eyes. When I opened them, with Nathan's fingers still in my mouth, the older woman was staring at me with a wide-open jaw. I took the fingers out of my mouth and smiled. She didn't smile back.