14 Day Mistress - Pt. 03

Day 6

I woke up with vigor. Excited for the adventure of the day. Another note greeted me with instructions to go the address of a tailor in Costa Mesa at 11:30 concluding with "wear the dark red panties". It was getting almost impossible to concentrate at work. But honestly, I didn't care. At 11:30 I was walking through the doors of a very nice-looking tailored clothing store. A gentlemen greeted me by name and directed me to the back into a dressing room.

"Undress please and we will get you fitted" he said politely. "You may leave the panties on" he added. What the actual hell. Who was this woman?

I did as I was told. I was getting surprisingly comfortable in my panties. The dark red ones were a thong but made of a much thicker and firmer material. And they were tight. As I moved up onto the podium, the tailor began measuring me and taking notes, starting at my feet. As he moved up and got to my waist, he moved around behind me and cocked his head. As if he was adjusting a crooked picture on the wall, he pulled my panties down slightly, reached between my legs and grabbed the head of my cock. In one swift motion, he pulled my cock back between my legs and moved my balls up into my pelvic cavity, smoothly locking it all into place with the tight thong.

"This is how a gaff is worn sweetie" he said pleasantly.

"Noted", I thought as I looked down to find my cock bulge completely gone.

He finished measuring the rest of my body, all the way to top of my head. It was a little excessive, but my new feminine look down below was worth it.

"I'll need to try a few items on to adjust fit sweetie" he said as he held my hand and ushered me to a rack of clothes.

He rustled through them and pulled out a pair of shiny high waisted yoga pants and a matching long sleeve bodysuit.

"Put these on and come back out" he directed.

I stood for a minute in the dressing room wrestling with the fact that I was about to put on women's clothes. The panties were one thing because they were just sexual. But this was different. Wasn't it? I mean, it wasn't a dress or anything. It was no different really than workout tights for men. I knew I was rationalizing, and I knew I was going to put them on.

When I emerged, I'm sure I looked embarrassed. He politely welcomed me "absolutely lovely, step right up."

I think I might have blushed. I stood up facing him as he brought out a silky black corset. The thing looked complicated, with laces and hooks and stiff internal supports. He wrapped it around my waist and began hooking the front hooks. It was tight, but not too bad.

He moved around to my back said "reach up and take hold of the bar above you sweetie. Don't let go."

He began manipulating the strings behind me, pulling them tighter.

"When I say breath sweetie, I want you to take a deep breath and then exhale completely and hold it" he directed.

The first time, I was a little shocked as the whole corset sucked in so tight it took a second to catch my breath.

"That's a good start." he whispered, "three more times and we should be there".

I looked back as I noticed him connecting the laces to a cable coming from the wall behind me and he said "this time I want lift your feet so that you are hanging from the bar as you breath out."

Whatever I felt the first time didn't compare to this new method of torture. My breath was taken away and I felt like my organs were going to come out of my mouth. We did this two more times before he proclaimed "we may end up one size smaller, but this looks perfect for now."

Tying me off in the back he proclaimed, "darling you are just perfect. A few more things to work through and we will be done for now."

"You are a size 10 and a half shoe" he more stated than asked. He walked around the corner and I heard rustling as I struggled to breathe.

He came back with a very sexy pair of three inch heels. "Now I would never put you in something so simple, but they will be good for size" he said as he knelt and lifted my foot.

She slid on each of the heels as I held the bar above again for balance.

"Now you will have to practice walking in them. Just remember, you will need to walk on your toes. It's a learning curve but worth it" he said as if I would be doing a lot of walking in heels.

With an approving smile on his face, he gently turned me around to look into the three surrounding mirrors. I'd say it took my breath away, but I honestly could barely breath as it was. Nevertheless, I looked totally different from the chest down. I looked totally hot. My waist was tiny making my hips look totally feminine. My crotch was flat with a slight camel toe and my legs suddenly looked long and sexy with these damn heels. I could feel a slight adjustment in my core. I had crossed a line I knew. One that seemed like it should have been a pretty damn big line but once I was over it, it didn't feel that big at all.

I shuddered slightly as the tailor said "you're more than welcome to stay and stare for a bit, but we are done. I'll let Eden know when everything is ready. She asked me to give you this note."

In that elegant handwriting I had become so used to, I read "Advanced Colonics Appointment today at 4:00pm" with an address.

Day 7

When I got home that evening, there was a box on the doorstep that somehow I just knew was for me and was something I needed to open in private. I walked around the side of the house and quickly pulled out its contents dropping the box into the trash. I slipped two smallish bags into my pockets and glanced at the note attached; "I suggest you sleep in the largest one, you will be glad you did."

I moved quickly to the shower and brought my two packages in with me. Inside I found two soft, but firm contoured butt plugs, one significantly larger than the other. While the message now made sense, I wasn't' sure I would be able to fit the largest one. Though I'd give it my best. I wore the smaller one out do dinner that evening, but before the first plate hit the table, I was yearning for the large one. Every move I made in my chair, I felt the plug work its way around inside me.

The dinner felt like it would never end. When it finally concluded, I was aware that my urgency to get back home was a little too obvious. Not caring, I headed straight to the bathroom when I got home. Pulling out the small plug, I quickly slid in its well lubed replacement. I got to about 3/4 of the way in before I got stuck. I worked it around, twisted it, did my best to relax, but it didn't seem like it was going to fit without tearing me open. A sudden disturbance startled me, and I fell back onto the couch. In one unexpected moment, the plug lodged between my ass and the couch and forced its way all the way inside.

I woke early to an incredibly full feeling. In the shower that morning I removed the plug, cleaned it, and then reinserted with an abundance of lube. It was surprisingly hard to get in and out, but once it was in, it felt perfect. Slipping on a pair of boy short style panties, I finished getting ready and headed out. Anticipating a note in the truck, I was very disappointed to be left in the dark.

Work was completely non-productive. Not just because I had a huge plug filling my hole, but because all I could think about was the pure debauchery I had started to become accustomed to. Around noon, I headed out to grab a bite to eat. As I entered the lobby, I heard that terrifyingly erotic voice from behind me as Eden sidled up next to me.

"I have a car for us outside" she said with a subtle smile.

"I hope you've been wearing your gift" she prodded.

"I have" I replied as we slid into the back of a large town car.

A few minutes later, we were pulling into the Peninsula Hotel and heading up to the roof. The doors opened to a huge party going on at the pool. The place was filled with beautiful people; men, women and multiple trans (some obvious and some I really don't know.

Eden was greeted by a large security guard, "good day Ms. Eden, your cabana is ready."

The instant recognition from the security guard was just the beginning. It seemed everyone who worked there and many of the guests were very familiar with my escort. Suspicious, but in no frame of mind to ask questions, I followed closely until we got to a private cabana at the far end of the pool.

My curiosity peaked about where this was going, I threw out "Some absolutely beautiful women out there."

To which Eden laughed "They are indeed, but I'm pretty sure I'm the only vagina on the roof right now."

No freaking way I thought. I just walked through a Victoria Secret pool party, and she was telling me that they were all trans.

"Let's get you ready" she said breaking my internal conundrum.

She motioned to the security guard to close the large pocket doors to the cabana. The place was fully decked out with fruit, drinks, and all sorts of luxurious accommodations. Eden opened a closet revealing a bright pink catsuit hanging inside. She looked back at me and there was no doubt I was to put it on.

"I'll give you a few minutes sweetie. You can put your clothes in the closet and meet me in the bathroom once your dressed."

She walked out leaving me staring at this hot looking shiny pink outfit. I'd love to say I hesitated, but I didn't. Stripping down quickly, I wasn't sure if I should wear my panties underneath or not. Holding up the suit, I noticed there was a three-inch open slit in the back. I guess that answers that question.

I met Eden in the bathroom. It was spacious to say the least and she had changed into a tiny bikini the same color and material as my new suit. She held a pair of matching latex gloves and slid them on each of my hands. Holding my had, she led me to a back wall with a neon sign above a beautifully velveted wall that read simply "Enjoy".

"Your room is over here" she said as she directed me to a hidden door to the side of the velvet wall.

Once inside, she turned on a soft red light to reveal a very small room with a cushioned bench about four feet long that almost touched each wall.

"Bend over sweetie" she directed as she grabbed the plug inside me.

"Oh god" I gasped.

The firmness with which she held me suddenly by the base of the plug sent shock waves up my spine. Placing her hand on my back she slowly pulled it out. Empty, is what I suddenly felt.

As if sensing my desperation, she sat me down on the bench and whispered in my ear "don't worry, you'll be full again soon."

Then she turned and walked out. I heard a very secure sounding lock slide into place. Outside I could hear the muffled sound of the doors opening and soon the cabana seemed to be the center of the party. Fifteen or so minutes went by, and I began taking account of my surroundings. Shocked I hadn't seen it before, I suddenly noticed a padded hole in the wall toward the end of the bench. I didn't have time to contemplate the purpose of the hole before the door the bathroom opened, and I heard someone enter.

A few seconds and I heard the obvious sound of a man urinating loudly. It felt so awkward, like I was a peeping tom, only I couldn't see anything. I straddled the bench and put my head down low to see if I could see anything through the hole. I startled as light suddenly poured through the hole just inches in front of my face. The urinating man had pulled the curtains aside and with a surprising fluidity, was sliding a shockingly long cock through the hole into which I was staring.

I did what I was trained to do. I opened my mouth and attempted to take the swollen head in. But my position was incredibly awkward in the small room. I couldn't get my head low enough to do what I needed to do. Fumbling and probably making a little too much noise, I clearly was taking too long.

I looked down to see the gorgeous cock starting to retreat. "No, I thought" as I swung my legs over the bench and quickly turned around and laid face down. I quickly reached behind me and grabbed the tool, halting its retreat. With surprising ease, I inched backwards and impaled myself.

As the first few inches pierced my already stretched hole, I found that wonderful sense of fullness returning. A smile crept across my face as I kept pushing myself backward until I felt my ass reach the padding around the hole. My lord he was deep inside me. Or so I thought.

Apparently, he was holding back because after a few slow in-and-out motions he shocked me with what must have been another four or five inches. I'd never felt anything like it. It just kept sliding inside. It took my breath away as it felt like it was lodged up against the curve in my bowls. That was it, he couldn't go any further. That was all the room I had.

As if he'd done this before, he began a series of short slow pulses. It still hurt, but an odd sensation began to take over as I felt my insides start to move around him, making more room. The pain didn't go away, but it was met with an equal amount of pleasure as he seemed to be at the hilt. I pressed back hard against the wall trying to get just a little bit more inside me. His slow pulses began to lengthen. They didn't speed up, just became longer strokes. Halfway out and then one slow movement rearranging my intestines to accommodate. The pure length of his cock made every stroke seem eternal. Finally, he pulled all the way out.

For just a second, but as his swollen head left me, I felt an odd coolness on the surface of my gaping hole. And then with the same tempo, he slid all the way back inside. I was in heaven. I lay my head down on the soft bench; my hands against the opposing wall to keep my ass pressed firmly against the opposing wall. I'm not sure how long he fucked me, but it was perfect.

Unlike my prior experience, this time I had no idea when he was going to cum. His pace never changed until suddenly he stopped at the top of his thrust. There was total stillness for the count of 4. Then a long series of twitching I could feel from my stomach all the way down to my entrance as he poured his fluid deep into my core. My eyes closed and I could visualize the white fluid pouring from that small slit sitting at the end of the most wonderful cock I'd ever felt. I didn't want it to end, ever. With the same methodic movement, he pulled out of me and my whole body shuddered then collapsed.

I lay there breathing heavy, my ass still pressed firmly against the wall. I sensed rather than heard him leave the bathroom. That was wonderful, I thought. I guess I assumed that was the end and just wanted to lay there and soak in the glory for a little longer. I was quite surprised to suddenly feel a probing coming from the same hole. In complete contrast to the last 20 minutes, the next 10 were far from gentle or sensual. What it lacked in deep penetration, it made up for in girth and strength. I felt pure power and a little bit of anger as I was absolutely abused.

I said a quiet thank you to Eden for the plug I'd worn leading up to this. I was being destroyed, but without that warmup, I would be ripped open. My new friend felt good in a very different way. The excitement and pleasure came more from my wanting to please rather than the actual feeling. I was just a means to an end, and I loved it. I loved feeling like I was truly a hole in a wall. No surprise this time as my new friend began to scream expletives (in a relatively beautiful female voice) as the cock inside me erupted. I pressed hard back into the wall and clinched my walls to give as much pressure as I could muster.

Before she was even out of me, I heard a sultry voice say "tough act to follow".

She pulled out and very quickly I felt a much smaller penetration.

I actually thought it was maybe a finger before I heard through the wall "turn around sweety, I'm going to need something a little tighter."

I panicked a little, worried about positioning. But during one of my last fuckings, I had a flash of clarity. If I flipped the bench around, it was designed for me to lay on my back and lean my head off the edge. This would open my throat and allow me to place my mouth much closer to the hole.

I tried it and it worked perfectly. Now the small cock in my face could still barely reach my tongue, but I wrapped my lips around it and sucked with all my might. I'm not exaggerating when I say, he was groaning in less than a minute. Now the day was already full of surprises, but this one really came out of the blue. My small friend flooded my mouth with an immense orgasm. The first two shots actually impacted the back of my throat and gagged me through their pure force. But that was just the start.

I pulled back to try to clear my throat only to find my face absolutely flooded. I was completely trapped in position as wave after wave of hot semen poured into my mouth, my nose, my eyes. It was intoxicating. I quickly reached up to try to cap the firehouse with my mouth only to find several heavier streams flood inside. I swallowed as quick as I could but couldn't keep up, feeling cum dripping down the corner of my lips.

When it finally waned, I heard a deep laughing outside the wall as he retreated. I slowly sat up and let the liquifying semen drip down my cheeks and chin. At the same time I looked down between my legs to see a large pool on the bench and felt dripping from my backside. I breathed in deeply enjoying the thick smell in the air.

As I sat in a pool of cum, I became aware of another presence entering behind me. I looked back to find a beautiful thick black cock protruding from the hole in the wall. Resolute, I brought my stomach down to the cum covered bench and thrust my hole back against the wall. The straining member slid in way easier than I would have expected but I guess I was well lubricated at this point. Relaxing my body completely, I let my new friend slide in and out of me with deep long strokes.

Not too fast, but not slowly. He fucked me with intent. Not an intent to finish, but an intent to satisfy his needs and his needs only. It felt so good. As if I was just a means to an end. And I felt the end coming soon. He poured himself inside me and was gone.

When he pulled out, I felt my well used hole continue to gape open for a few seconds... then shudder closed. My head still on the bench, cum drying on my cheeks, I never moved as the next cock entered me and began pounding away. This one seemed to last forever, but my hole was numb. The physical sensations gave way to more of a mental and emotional fucking. I was vaguely aware of him finishing inside me only to feel another enter.

I honestly cannot say how many cocks I had inside me that day and I don't really know how long I lie there, but at some point, it stopped. I'm not sure if I fell asleep before or after, but I woke up with my head in Eden's lap. She brushed my hair as I stumbled back into consciousness.

"What a good girl you have been today, Chastity" she said sweetly.

"My friends were so pleasantly surprised" she giggled as she leaned over me and curled several fingers inside me.

I could hear the slurping of cum as she fingered me slowly. She sat up, my head still in her lap, and placed a cupped hand over my mouth....