Discovering Amber Ch. 09

Mistress Notes: My intentions with amber were simple at first, but became more complex over time. Our roles seemed to continuously evolve with her becoming more and more submissive and femme and my becoming more Dominant. After a year I really couldn't see her as anything but amber, even when we went to her company's holiday party (which she wore a suit and tie) she was still my sweet and slutty little amber. It didn't help that under her suit she had on my favorite lingerie for her and, when I took her upstairs to the hotel room, I fucked her silly with my strapon. The mental change had not just happened to her but myself as well, however finding someone who could embrace her as well as myself wasn't easy. The fact we'd also gotten engaged, partly to keep my parents happy and partly because we were going to be forever tied together, didn't help. "oh, have you met my finance amber?" is not exactly a line that comes up in a talk about a relationship with a new partner. I was determined to find a way to make it work while seeing what limits amber and I could reach together.

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Ms. Allison and I celebrated my sissy birthday with a pink and white cupcake that was adorned with a cute bow and penis shaped candle. While we relaxed Ms. and I talked about how things had progressed during the last 12 months and how I had evolved as a sissy. My shortest heels were 5" tall, anything shorter was considered a "flat", my lingerie and outfits all but exploded out of my closet and dresser drawers, the neighbors barely saw anyone but amber and Ms. Allison anymore, our sex life was very regular with my mouth being used almost daily and my sissy pussy used 5 - 6 times a week at least. Also, I was now waiting tables at the club once a month and going as a guest another night. There were still only 2 alternative lifestyle nights and we were always present at both. Master Max had an inexpensive rack in his office with outfits for me to wear when waiting tables. He had slowly changed his greetings upon my arrival as well.

Where he used to have me twirl to show off my outfit had changed because now, I would get dressed under his watchful eye on work nights. Him kissing one cheek, which changed to two cheeks which recently changed to a soft kiss on the lips as well. He went from taking my hand to lead me to his office to wrapping his arm around me. No matter how busy he was, Master Max always made sure to stop everything he was doing to supervise and observe my getting ready for work or settling up my receipts at the end of the night. Even on nights I didn't work my coat was hung in his office so I could show him what I had on first. At the end of work nights, I would go into his office and settle up my tips as well as pay, he paid me under the table, then would kiss me goodbye. These now included a quick cup or squeeze of my butt. The conversation with Ms. Allison now highlighted the fact that Master Max was essentially "courting" me. The thought made me blush terribly but also excited me a bit. He was a dearly sweet man, probably 15 - 20 years older than me, but as genuine and loving as they come.

"I think he has a crush on you sweetie," Ms. Allison teased, "I think he wants to go further than a simple kiss on the lips too."

"I don't know," I said thinking about how far he would want to take things, "that's a big step."

"I will tell you what," Ms. Allison said sipping her glass of wine, "give it some thought, and we will talk about it on Thursday."

"Yes, Ms." I replied feeling my legs involuntarily squeeze slightly.

It was Sunday night, while most of my friends at work would have spent the day watching football, I'd spent mine as a "girl's day" with Ms. Allison. At the moment I was wearing an oversized white men's dress shirt over a black lace demi bra, breast forms and matching thong. We'd done facials, manicures, pedicures and I'd taken a long soak in a bubble bath. Did I miss football? Sure. Would I be able to keep up with conversations about the games at work tomorrow? Not a chance. But I sure as hell felt sexy!

True to form Ms. Allison did not bring up Master Max again the rest of the week. Thursday night the conversation came up as I cleaned up after dinner. Ms. Allison retired to the living room wearing a pair of comfortable shorts that resembled boxers and a loose-fitting tank top while I teetered around in my 5" heels and lingerie cleaning up.

"So, muffin," Ms. Allison asked as I entered the living room and knelt in front of her, "I am sure you've been giving this Max thing a lot of thought this week. What did you come up with?"

"Well," my voice cracked as I spoke, "I guess that if that did happen with anyone," I cleared my throat again painfully trying to find my words, "it would be best with him." Ms. looked at me and nodded as if telling me I needed to speak the exact words. "So," I swallowed hard again, "I guess I would say that tomorrow night would be it."

"Would be what muffin?" she prodded.

"The night I suck a real cock." I replied unable to look up from the floor in front of me.

"A real man's cock, right?" She said almost soothingly, "I mean you've been sucking pretend cocks for over a year at this point."

"Yes, Ms." I replied feeling almost light headed as I spoke, "I will suck a real man's cock tomorrow night."

Ms. Allison quickly moved forward, falling to her knees in front of me and grabbing me in a big hug.

"I'm so proud of you amber," she said pulling me tightly to her, "so proud of the sweet girl you've become."

"Thank you, Ms." I replied softly.

"No time like the present to practice!" She all but squealed in excitement as she released me.

Ms. Allison reached into the end table pulling out a life like 8" phallus with an insert for her then quickly stood.

"Pull them down amber." She instructed.

Reaching up I pulled down her shorts and the black panties underneath, guiding them straight to her ankles.

"I'm so excited about this I'm wet already!" She said practically falling back onto the couch.

I could only blush in response as she worked the insert into her vagina.

"Okay baby," she cooed excitedly, "show me how you're going to pleasure your new boyfriend!"

The word boyfriend hit me like a ton of bricks. Prior to this my "boyfriend" had been a 7" dildo that I kept on my nightstand for a few months. Now it would be a physical person. I crawled between Ms. Allison's spread legs, my mind racing, wondering what he would taste and look like. Before I even settled onto my knees my tongue was swirling around the big latex balls. His would be warmer, and fuller than these I thought. I was soon lost in the idea of sucking not just her dildo to bring Ms. Allison pleasure but lost in wondering what it would be like to do it for really real. I brought Ms. Allison to orgasm a couple times before she finally had me stop.

"We don't want to wear your jaw out before tomorrow night do we amber?" she asked as she pushed me away.

"No Ms." I replied nervously.

"Go get ready for bed baby." Ms. Allison instructed, sending me on my way.

I did as I was told, returning down the stairs wearing a baby blue nightie and house slippers. As I approached the living room, I could hear Ms. Allison reaching another orgasm. It was quite clear that she was as excited about my next step into sissy-hood as I was. Entering the room, Ms. Allison pulled the dildo from her body, holding it up for me to clean off.

"You can lick it clean if you'd like amber." She cooed as an aftershock rippled through

her body.

"Thank you, Ms." I replied quickly licking her wetness from the dildo like a phallic lollipop.

That night I slept poorly; my mind raced with all kinds of thoughts. I'd taken some large steps over the last year that had me questioning my sexuality, and now I was looking forward to having a real cock in my mouth. The traditional side of my mind though how abnormal that was. But, for the better part of 8 months I'd been going to a dance club frequented by gay men while dressed as a woman. I'd been kissed, groped and grinded against. All of which I'd enjoyed terribly. The nights I waited tables were no tamer than the nights I spent on the dance floor, honestly, they were probably a bit worse as I was touched by more men on those nights than the others. More than a few of my regular customers preferred to give me their drink orders while I sat on their laps! Still, I did not consider myself "gay". I had no desire to do anything like that say, at work, but in that setting while in those clothes it was just natural. It just simply fit. I loved the feeling of sexuality, the idea that I was arousing others while being aroused. Ms. Allison called me a cock tease, and I truly was. I could feel how hard my dance partners were as they gyrated against me. This just felt like the next natural step for me, labels or no labels I wanted to do it. My dreams, when they finally came, were filled with wonderfully attractive and cum filled cocks. Ms. Allison made sure the week leading up to "my big night", as she called it, was full of teasing and lots of oral practice. When Friday morning came, I was ready to suck just about anything!

"So, you're working from home today amber?" Ms. Allison asked as I brought her coffee and breakfast.

"Yes, Ms. I am." I replied wondering what fresh torment she would unleash as a result.

"I'll leave a nice outfit out for you then," she said sipping her coffee, "it's not like you have to worry about anyone seeing you after all."

"Yes, Ms." I replied with a face burning blush, "I look forward to wearing whatever you select."

"Well of course you do baby girl," she smiled as she spoke one of her fun nicknames for me, "now run along I have stuff to do."

After cleaning up the kitchen and having my own breakfast I returned to my bedroom.

There Ms. Allison had laid out lingerie she rarely picks for me. In her view sissies should wear femme colors, like pink, pastels, and lighter selections. On my bed she selected a black satin corset, back seamed stockings, black satin thong, opera length gloves, black patent heels and put a long brunette wig for me to wear. The outfit was very sexy and one of my favorites. I quickly removed the nightgown and panties I'd been wearing putting them on starting with the stockings. They felt so luxurious as I slid them up my legs, I'd been shaving my legs for well over a year at this point but slipping stockings up them always gave me a rush. The thong was stretchy enough to allow for my caged clitty as well. Finally, I pulled the corset up my legs then stepped into the almost 6" heels feeling a chill run up my spine as I did. As if on cue Ms. Allison entered the room to tie the corset.

"It seems all that corset training has paid off amber," she said tying the corset snuggly, "you've got quite the little figure."

"Thank you, Ms." I replied looking at my reflection in the mirror and feeling my clitty strain at my cage.

"I'll leave you to do your make up," she said giving my ass a playful smack, "and finish with your wig, the big boobs today too amber."

"Yes, Ms.!" I replied.

It took a bit of work to put my large breast forms into the corset top but it was worth it, they were all but popping out of the cups when they were in place. I did a darker lip stick and eye shadow to go with my outfit then put on the long, straight brunette wig that not only framed my face nicely but managed to frame my boobies just as well. Going downstairs I poured myself a cup of coffee then entered my home office. It felt odd yet wonderful to sit in my office while dressed up so sexily. The lipstick on my coffee mug was a subtle reminder, as if the corset wasn't enough, that I was not a "real boy". During the day Ms. Allison checked in on me, she had me send her a picture of my feet up on my desk. I made sure to get as much of my stocking covered legs as possible while I showed off my sexy heels.

"Good girl!" was her typed response.

When Ms. returned home, I had dinner ready to go. Ms. Allison entered the house, greeted at the door with a glass of wine and a kneeling sissy, everything was on the table awaiting her arrival. Dinner was quick and quiet as I was completely lost in thought of what I had in store for my night.

"We're going to do something different tonight amber," Ms. Allison said setting down her fork and sipping her wine, "I'm going to get you dressed up before we go."

"Yes, Ms." I replied.

Over the months I'd been waiting tables Master Max had always delighted in picking out my outfit for the evening. Sometimes I'd even have to model a few of them until he settled on the one he wanted. I knew he'd be slightly disappointed that he was not given the opportunity to dress me but he'd surely get over it. I cleared the table and did the dishes while Ms. Allison relaxed. When the kitchen was cleaned, I followed her upstairs where she had me strip to my thong. I could feel the hair on the back of my neck standing on end as Ms. left me momentarily to get my outfit. When she reentered the room, she handed me a pleated micro-miniskirt. The skirt was black with gold in the pleats. As it was a micro-mini it sat just above my hips and a couple inches below my belly button while leaving the bottom inch of my butt exposed.

"Tips will be good tonight in that!" Ms. Allison laughed as she handed me a matching halter top.

"Yes, they will be Ms.!" I replied wondering how many bills I'd need to rescue from my thong this evening.

"Hook it behind your neck," Ms. Allison instructed, "then hold your boobs in place while I tie it for you."

The halter top was black, with sheer material above the cups and gold detail around the edges. The hook behind my neck was relatively easy to manage while Ms. tied the halter strings behind my back. My larger breast forms filled out the cups nicely and the neck managed to mask my Adam's apple a bit as well. Ms. Allison then handed me a pair of thin, black ankle socks with gold lace ruffles to put on. Finally, a slightly more sensible pair of heels than I'd worn all day completed the outfit.

"One more change amber." Ms. Allison said looking me over. "Take off that wig," she said turning her back to me, "it just won't work." I removed the wig putting it on the Styrofoam head for safe keeping. "Here we go," she said placing a blond wig on my head, "this will work much better!" Ms. Allison tugged the wig into place before letting me look in the mirror. "I'm sure Max will appreciate the handles too!"

The blond wig had a pair of long pigtails just behind and above my ears with black and gold scrunchies holding them in place. I looked then realized what she meant by handles feeling another chill ripple through me.

"Fix your make-up," she said with a firm smack on my ass, "I need to get ready too."

Less than 30 minutes later we were heading out to door to Ms. Allison's car. Thankfully, she'd been kind enough to allow me to wear a short overcoat to hide my all but bare bottom. Ms. Allison wore an amazing Oriental style red dress with golden details and matching red and gold heels with her hair pulled back. She looked stunning as she held the door open for me to get in. Just as dinner had been the drive to the club was very quiet. Ms. Allison parked in the parking lot across the street then, without a word, took my hand.

"At the end of the night," she said giving my hand a gentle squeeze, "how you end it with Max is completely up to you."

"Thank you, Ms." I replied swallowing hard.

We got out of the car, then Ms. Allison took me by the arm leading me to the front door. My heart raced as the sound of our heels across the pavement echoed loudly. After she knocked Master Max appeared at the door, as always, he smiled wide at our arrival.

"Allie, my dear," he said opening the door, "you look simply stunning!"

"Thank you Darling!" she replied kissing Max's cheeks.

"And amber," he said taking both of my hands in his, "I hope you are ready for a fun night!"

Before I could answer Master Max pressed his lips to mine softly.

"Yes I am." I replied feeling my face burning as red as Ms. Allison's dress.

"I hate to let you down," Ms. Allison said leading Max towards his office leaving me to follow them, "but I picked out an outfit for amber tonight."

"Well you know I love playing dress up," Max said looking back at me, "but I can't wait to see what you've selected!"

Entering his office, Max took a seat behind his desk while Ms. Allison leaned on the front. Both sets of eyes were on me as I untied the belt of my short trench coat. Taking the coat off I draped it on the end of the rack containing my outfits then took a step forward.

"Oh, turn around slowly!" Max said hiding none of his appreciation for Ms. Allison's choice. "Oh yes," he continued as I slowly turned, "I do love that bottom of yours!"

"Thank you, Master Max." I replied feeling my face flush again.

"Wonderful choice Allie," Max said slowly looking me up and down, "simply wonderful!"

"I knew you'd enjoy her in it," Ms. Allison replied giving me a wink, "go out and get stuff ready now amber."

"Yes, Ms." I answered turning quickly enough that the skirt flew upward a bit revealing more of my bottom as I exited the office.

By this point the bartender and I were old friends. He wasn't gay but he was pretty accepting that his one and only waitress, who also gave him 10% of her tips, dressed in a manner that would increase our earnings. In less than an hour the club was open, and things were getting pretty busy. As expected, my outfit garnered a fair amount of attention, touching and comments. After doing this as long as I had I took them all in stride. Ms. Allison was at her usual high-top table where she could survey how I was doing but also keep an eye on the customers I interacted with. Since we'd started, she'd only had to speak to one gentleman about his conduct regarding me. For the most part, the customers were regulars and I knew most of them by name. At some point during the evening a rather tall man joined Ms. Allison at her table, I couldn't see his face but I could see hers. While she seemed to be enjoying the conversation, I eventually made my way over, he would surely want a drink after all right? He was easily 6'4" tall, and after removing his jacket showed off some very muscular arms.

"Would you like something to drink?" I asked as I got to the table.

"Oh, amber," Ms. Allison said with a gleam in her eye, "just in time! I need a refill and Jimmy hear will need something too!" The tall man turned to look at me. "Jimmy you remember my fiancé amber right?"

I knew who he was immediately! He worked part time as a personal trainer at the gym I used to use, his stories of female conquest were always a point of conversation. After seeing him in the showers a couple times it wasn't a surprise, he probably got a workout just lifting his cock to pee!

"amber?" He said looking me up and down. "I don't recall meeting an amber," he said just as his eyes got bigger, "well now, that explains why we haven't seen you at the gym anymore!" He laughed loudly looking me up and down again. "You sure as hell couldn't walk into the men's locker room looking like that, now could you?"

"Umm," I searched not only for words but a hole to crawl into as he touched my waist with his seemingly massive hand, "no, I definitely couldn't."

"Well you must be doing something right," he said as his hand slowly caressed my skin, "you were never that toned with me!" His eyes lingered over my flat tummy and sparkly belly ring. "This is quite a look you have going," he turned to face Ms. Allison before continuing, "fiancé huh?"

"Well my parents are traditional," Ms. Allison replied then nodded to me, "plus, who wouldn't want to marry this sexy girl?"