Discovering Amber Ch. 09

"True," Jimmy replied still holding me in place with his hand, "she is definitely very hot!"

He turned to me again and placed his drink order before sending me on my way.

As I walked across the crowded room, I felt positively light headed. It had been almost 2 years since I'd seen Jimmy, he was tall, handsome and built. He was a man's man in every sense and here I was with my ass and fake boobs hanging out of a slutty cheerleading costume! I managed to return to their table with Ms. Allison's martini and Jimmy's whiskey on the rocks without spilling them.

"You know amber," Jimmy said as I set their drinks down, "I thought you were just good looking from the front!" He took a sip of his drink then leaned to look at my backside.

"But you're just as good looking from the back too!" I simply blushed and smiled in response. "What do I owe you?"

"Oh, my drinks are on the house," Ms. Allison thankfully answered for me, "but you can give amber a tip if you'd like."

If I described my walk across the room as making me feel light headed that pales in comparison to how I felt at those words. The feeling can only be described as that first drop down a rollercoaster where all your organs shift upward!

"Now that sounds fun," Jimmy said pulling out a crisp five-dollar bill, "I've been watching the guys tip you and now it's my turn!" Jimmy leaned forward, placing his nose almost directly next to my ear as his right hand slipped up my left hip and under my short skirt. His hand continued over my butt cheek until he located the back of my thong. "And I can put this right here?" He asked as he started to tuck the stiff paper between the material and my skin.

"Yes, please Sir." I responded automatically.

"I love your perfume too amber," he said as he slipped more of the bill into my thong, "I had this chick I loved to fuck who wore that all the time!"

My knees almost gave out as he spoke while my clitty poured precum while racing to fill the void left by my shifting organs! Honestly, if he wanted to bend me over right there and fuck me, I doubted anyone could stop him. He was a big, burly alpha male and I was in pigtails and heels with a belly ring that had the word "sissy" on it. I knew I surely couldn't. His hand slowly glided over my ass as he retracted it. His eyes no longer just looked me up and down, they devoured me. My mind raced, was Jimmy bi? Was he teasing about fucking me or serious? It took a moment before I could leave the table, a moment that felt like a lifetime.

For the rest of the evening I attempted to remain as composed as I could muster. It wasn't easy, not only was I unsure of Jimmy's intentions with me I knew exactly what his intentions were with Ms. Allison! I fought to focus on what I was doing, thankfully the bartender, Mike, helped to keep me on track. The remainder of the evening seemed to fly past, before I knew it customers were saying their goodbyes and heading out. I'd had no idea how I'd made it through the last 3 or so hours. As Mike and I cleaned up the bar, and I counted out my tips, Ms. Allison and Jimmy moved to one of the lower tables. Instead of sitting on a high stool Ms. Allison ended up sitting in Jimmy's lap with her back to me. I could see his right hand deftly slipping up and down her back lightly but couldn't see his left which had to be on her legs. I was feeling a bit jealous when Mike snapped me out of it.

"All set there amber?" He asked looking at the pile of cash in front of me.

"Uh, yeah, I think so." I replied handing him a wad.

Truth be told I'd counted my tips four times but never arrived at an actual total. I probably handed Mike half my bank for the night.

"See you in a couple weeks!" He said obviously pleased with his haul.

I slowly made my way to the table occupied by Ms. Allison. As I neared, I could see Jimmy's left hand was delicately touching Ms. Allison's right leg. They looked up as I got closer.

"Amber baby," Ms. Allison said eliciting a giggle from Jimmy, "have you settled up with Max yet?

"I was going to do that now," I replied unable to take my eyes from Jimmy's left hand, "I just wanted to see if you needed anything first."

"Oh, I'm really good!" Jimmy replied with a wink.

"From what you've told me tonight," Ms. Allison said returning her attention to him, "I bet you are!" She flicked her glance back at me, "Have fun with Max muffin!" then returned her attention to Jimmy.

I made my way to Max's office wondering if it were possible to feel any more emasculated than I was. Of course, my entire life had been one big lesson in being emasculated so I guess the answer was no. Or was it yes? I felt bound and determined to prove myself as I strode confidently to Master Max's office. While the logic behind my train of thought defies me now, the thought of being the best damned sissy I could be was my ultimate goal!

"How was the night?" Master Max asked as I walked into his office.

"It was great!" I replied slowing myself to a more casual saunter. "We did fantastic!"

"Mike seemed quite pleased," Master Max replied, "although you may have over tipped him."

"I'm sure we'll work it out." I replied feeling the lust building inside me.

I continued toward his desk setting my receipts and cash on the corner. While this was not uncommon practice for me what came next did. Leaning forward I cupped his face with my left hand while bringing my lips to his. He was confused at first and reacted slowly, but I pressed on as I flicked his lips with my tongue.

"I just want to thank you," I said kissing him again feeling his lips part, "for embracing me here." He responded far better on my second attempt to kiss him thrusting his tongue into my mouth. "And I want to show you," I said a bit breathlessly as our lips parted slightly, "just how much I appreciate you."

"I don't know what to say?" Master Max whispered after I kissed him again.

"Say yes." I whispered in his ear before giving his earlobe a lick.

"Yesssss." He hissed.

I kissed my way down his body, slowly settling onto my knees as he leaned back in his office chair. The one thing I'd never practiced at home was removing a belt and pants, it's not without its challenges while you're facing them. Thankfully, Max helped a bit, even lifting his hips so I could pull them down to his ankles. His cock was simply gorgeous. I instantly wanted to make love to it with my mouth! As I licked my way up the bottom the warmth was almost as intoxicating as the precum that awaited me at the tip. He was a good 6" fully erect and more delicious than anything I'd ever tasted before. When I first heard him moan, I knew I was hooked on doing this more than just the once. Here, on my knees with a throbbing cock in my mouth, I felt more powerful than I'd felt in months. Even as I looked up at him, seeing the lust burning in his eyes as I licked and sucked his balls, I couldn't help but wonder if I'd ever look at a dildo the same way again?

"Oh, amber," he moaned throwing his head back, "I'm going to cum so hard!"

I don't know what came over me, but hearing those words sent my desire into overdrive! I started pistoning my mouth on his shaft as fast as I could manage while massaging his balls with one hand and stroking him with the other. Then I felt him swell, felt his body brace, and a hand clamp on the back of my head holding my nose against his lower abdomen. The first jets of hot cum shot straight down my throat burning their way down my body. He let up, allowing me enough time to pull back and inhale sharply, before the next spurts exploded into my mouth. I'd never tasted anything like it, I mean I'd tasted myself but this was so much different. He was salty and sharp tasting but also intoxicating. I wanted more! Milking his balls and shaft I sucked and massaged every last once of his sticky goodness into my mouth before finally releasing him. As I did his limp cock lay on his abdomen while I licked my lips like a hungry predator waiting for more.

"That," Master Max panted, "was the most amazing blowjob I've ever received in my entire life!" His chest heaved as he spoke. "I can't even," his eyes stared into mine, conveying more than his words ever could, "I just can't. Holy shit!"

I smiled up at him savoring his taste as well as his reaction.

"I wanted you to be my very first." I replied softly.

"I was your first?" Max's eyes were wide with shock. "How are you that good the first time out?"

"Lots of practice." I said with a wink.

Leaning forward I gave his exhausted cock a soft kiss before trying to get to my feet. Ever the gentleman Max took my hand to help me up. As I stood, I took his hands pulling him out of his chair.

"With the shifting of my blood flow," he said wobbling a little, "I don't know if standing is such a good idea for me."

"I thought you'd like me to get your clothes back in order." I replied.

"Who am I to say no?" He smiled in response.

Squatting in front of him I pulled his boxers and pants back up to his thighs. Then I gave him one last surprise.

"And I should thank you too!" I said giving the tip of his cock one more kiss.

Master Max helped me pull his pants up and tuck in his shirt before he escorted me back to the bar area where Ms. Allison and Jimmy waited.

"How did things go?" Ms. Allison asked as we came into view.

"If this is the reward for letting you get her ready before hand," Master Max said giving me a squeeze, "then feel free to dress her every night!"

"Oh, don't worry," she replied with a wicked grin, "the thanks will certainly be more regular regardless of the outfit!"

I blushed, looking downward and noticing Jimmy's left thumb and index finger were now no longer visible under Ms. Allison's short dress.

"We should get going," Ms. Allison said looking down at Jimmy, "amber and I have some catching up to do."

"If you insist," Jimmy replied not moving an inch, "I hope I don't have to wait two weeks to see you though."

His response made me wonder if I were invisible, I was her fiancé after all and he was obviously trying to make a date with her!

"Why don't we do dinner tomorrow night?" Ms. Allison responded not missing a beat.

"You can pick me up around 7."

"That sounds like a plan," he replied with a grin, "what about amber here?"

"Oh, I'm sure she has something to do tomorrow that will keep her busy," Ms. Allison responded, "reorganizing her lingerie, shampooing her hair, maybe taking one of those bubble baths you like so much. Doesn't that sound fun amber?"

"Yes, Ms." I replied cursing my new found love of bubble baths.

"Well, at least let me walk you out." He replied continuing to ignore me.

"Of course!" Ms. Allison worked her way off his lap, giving me a wink, before giving Master Max a hug. "I'm glad you were her first." I heard her whisper to him.

"Me too!" Master Max replied.

Jimmy stood nearby wondering what he was missing, I was glad about that. It was bad enough a "gym friend" now knew about my other life I didn't need him knowing about how far I was going with it!

"If you'll come with me," Jimmy said extending his arm to Ms. Allison who happily took it, "you too sissy!" He also extended his arm to me, which I reluctantly accepted.

Master Max led us out as Jimmy happily walked us across the street to Ms. Allison's car. I probably would have noticed not wearing my overcoat, but I was far too distracted with all that had gone on to be bothered. As we approached the hood of her car Jimmy released my arm.

"Wait right here," he said almost sternly, "real ladies first."

He led Ms. Allison to the driver's side door, waiting patiently as she fished her car keys out of her purse. With keys in hand Jimmy's arm coiled around her waist bringing her to her toes. I watched as she threw her arms around his neck while his left hand moved from her hip to the side of her breast as they kissed. It was then I noticed that his right hand was firmly gripping her ass as their tongues toyed with each other! Numerous conflicted feelings churned through my body even after he released her. His hand, sure still on her butt, remained behind her as he opened her car door allowing her to get in. With her door closed Jimmy turned his attention to me. I was shaking in my heels as he approached, feeling even more dwarfed by his size than earlier, he slipped his hand around my waist leading me to the passenger side. I felt as if I were going to faint!

"I hope you don't mind that I'm taking your Mistress out tomorrow night," he said as he quickly turned me to face him, "but if you do, I'm sure she will work it out with you."

His body pressed against mine, I could feel his massive cock pressed against my abdomen as his right hand cupped my bare ass. He leaned in closer, practically pinning me against the side of the car, increasing my feeling of helplessness and vulnerability.

"Who knows," he whispered, "maybe you and I will get to play together one day." I felt his fat cock throb against me and my knees buckle. "I always did like fucking that girl who wore the same perfume as you," his nose nuzzled my ear as his voice got huskier and quieter, "and while she was a kinky bitch, I have a feeling you're even kinkier!"

I couldn't form words. I wasn't just breathless from his pressing against me, I was breathless from being so incredibly aroused. Where had this come from? I could feel my sopping wet thong, saturated with precum, and clitty straining against its cage from being in an unbelievably submissive position to a real man. My sissy pussy tingled at the idea of him all but splitting me in two! His cock had to be more than 8" as it strained against the jeans he wore as if it already wanted to invade my body. Even after he released me, I couldn't move. He pulled the door handled then had to take me by the hand to help me into the car. Honestly, it was a good thing he did as I was beyond being able to form a single thought outside of his cock. Ms. Allison waited to start the car, as we both watched him walk to his motorcycle. I wondered how he'd manage to sit on it without getting poked in his chin by his cock! The bike fired up, setting off at least one car alarm, before he pulled out of the parking lot leaving us both staring at his rapidly shrinking tail lights. A minute later Ms. Allison started the car so we could leave.

"How were things with Max?" She managed to ask several miles down the road.

"It was wonderful," I replied sheepishly, "he was quite the gentleman."

"That's nice," she said somewhat upset that I'd missed the point of her question, "but, how was he?"

"It was all I could imagine and more." I replied shifting in my seat. "His cock was so warm and his cum was ... amazing." I finally responded.

"I'm so glad baby." She said reaching over and taking my hand. "It was a big night for you," she continued, "and a big step."

"Thank you, Ms." I replied squeezing her hand.

"How do you honestly feel about tomorrow night?" She asked much to my shock.

"Well," I had to carefully weigh my response between jealous fiancé and loving sissy, "I knew you'd eventually take a lover." I pressed hard for my words feeling my mouth go dry. "And you've always wanted one that would be okay having me around, which isn't easy to find," I felt my eyes water slightly as I spoke, "I want to be everything for you, but there is one role I cannot fill."

"What role is that muffin?"

"I can't be that man's man I know you need." My tears streamed down my face as I came to the realization as well.

"Muffin," Ms. Allison said pulling to the side of the road, "no matter who I invite into my bed, you will always be my one truest love. I promise you that."

"Thank you, Ms." I replied.

"Not Ms.," she responded, "we're taking the rest of the night off."

"Okay." I replied as she all but launched herself over the armrest to hug me.

We embraced for several minutes before settling back into our seats. Spending the next couple minutes in silence, both recovering from the weight of our conversation, we held hands as the bright moonlight shown on us.

"Of course." Ms. Allison eventually said before clearing her throat. "I will need one thing before bed, which we will share tonight."

"What's that Allie?" I asked feeling a bit naughty using her first name while dressed.

"I'm going to need you to lick me until your tongue cramps," she said shooting me a glance of pure desire, "your friend is hung like an elephant and I'm horny!"

"I know he is," I replied suppressing a giggle, "I could feel him against me as he said goodnight.

"What is it he said while he was manhandling your ass by the way?"

"He said he had an ex who used to wear the same perfume I have on," I replied squeezing my legs tight as my sissy pussy trembled, "and how she was a kinky bitch he loved to fuck."

"He doesn't know what a kinky bitch is!" She laughed.

"Wait, are you talking about you or me?" I asked unable to suppress my laugh this time.

"BOTH!"

For the remainder of the ride we spoke as girlfriends about our newest conquest's massive manhood. As it turned out we'd both wondered how he could sit on his motorcycle sporting that massive hardon. True to her word, I did sleep in Ms. Allison's bed that night wearing only my clitty cage and only after licking her to mutual exhaustion. We would relax for a majority of the day as more of a couple than anything else, until it was time to get her ready for her date.

But that is a story for another day.