Discovering Amber Ch. 04

Mistress notes:

They key to training a sissy is arousal and knowing when to amp up how much they are experiencing. Of course, amber was in a constant state of arousal, she wore lingerie against freshly shaved skin every day, slept in lingerie, and was denied any type of relief or even the ability to just get hard. Life at home was a constant reminder that she was living life as a girl. When the time called for it, like when she needed to equate doing something she may not like with sexual gratification that's when the arousal needed to be amped up. At least twice every night amber would service a dildo with her mouth, when she did that I would not only massage the front of her panties, but I'd tell her how good she was doing at it, call her naughty names and make sure she equated having a cock in her mouth with pleasure. I also required that she watched "training videos" which were sissy-centric porn. A vibrating plug in her sissy pussy typically helped with those. It was much like Pavlov's dog, just sexual.

Ms. Allison.

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After three months of living as amber my training was progressing nicely. I was hoping however that a week-long business trip would give me a reprieve of sorts. Every year the regional managers for my company would get together, it was usually a great "guys week" as 99% of us were men. During the day we'd be in boring meetings but at night we'd be out late drinking and just carrying on. I had become good friends with five of them and we always looked forward to it. Leading up to it I didn't say much to Ms. Allison hoping I'd be able to just slink off Monday for the trip. Sunday evening she proved that she was still a step ahead of me.

"Are you excited about your trip tomorrow muffin?" She asked as I knelt in front of her and painted her toes.

"Ummm, yes Ms." I replied feeling her other foot slide further between my legs until her toes pressed against my hot pink thong.

"It will be fun to see the guys again," she continued as she roughly rubbed my swollen tessies, "I know you always have fun."

"Yes, we do," I replied sheepishly, "I'm sure it'll be a bit tamer this year."

"Horse shit!" Ms. Allison exclaimed. "I'm sure Mike will round all you guys up to go to the strip club just like he has every year!"

"I don't think I would go." I sheepishly replied.

"Why?" She asked pulling her foot away. "Think you'll get too aroused by what they are wearing than them taking it off?"

As much as her foot had been uncomfortable I now missed the feeling of her foot massaging my tessies. I even slid forward just a bit in the hope she would resume.

"I don't know," I replied not really able to come up with an excuse that would sound anywhere close to reasonable, "I just don't know if."

"If you should go look at naked girls while they dance around?" I shrugged my shoulders. "And what excuse would you give Mike that he wouldn't shoot down in a heartbeat? Sorry Mike, I can't go ogle strippers because I dress like one now. Wanna see?"

"Oh my! He could never find out!" I felt my face turn white at that idea.

Mike was always a blast, he was the life of the party, but he couldn't keep a secret to save his life! If he ended up knowing even half of what was going on with me everyone in the conference would know! He'd probably stand on a table and announce to everyone I'd been taking blow job lessons!

"Don't worry muffin," Ms. Allison said resuming my panty massage with her foot, "I won't tell him. Now hurry up so you can get to bed, you have an early flight tomorrow."

"I still need to pack too." I said as I resumed painting her toenails.

"Oh, I took care of that for you already!" She exclaimed in far to happy a tone to make me comfortable. "Don't look so worried," she smirked, "you have some boy clothes in there. Promise."

I didn't dare ask how much boy clothing was covered under the term "some". Instead I did my best to trust her as I have to this point. Never once during any of our trips out had I felt threatened or been concerned about my safety. Ms. Allison was always in total control of every situation and somehow, I knew that even my being two thirds of the way across the country she would still be in total control.

"I meant to ask about that Ms.," I struggled to find the right words, "I'll never make it through the metal detector with the brass lock on my cage."

"Oh, I know that!" Ms. Laughed.

"So how am I going to get through airport security?" I asked as she changed which foot was in my lap.

"Don't you worry your pretty little head about that baby," she smirked, "I'll make sure you aren't strip searched by the TSA!"

Amazingly this did not make me feel any better about things. Rather than push the issue I painted the toes on her other foot. While I had always looked forward to these conventions I was not looking forward to this one now. She had packed for me, I had a cage on my clitty with a brass lock that would set off the metal detector at the airport and I wasn't going to get the escape I was hoping for with this trip.

"I have more good news for you, muffin," Ms. Allison said out of the blue, "you're going to have some very specific rules for this week but if you're a good girl I have a very, very big surprise for you on Friday night."

Typically, a "big surprise" meant a real orgasm. Ms. Allison typically milked me a couple times a week but all that did was make me hornier and more frustrated. I didn't dare push, there was no way she would tell me her surprise after all.

"I will do all I can to follow your instructions Ms." I replied dutifully.

"Good girl now go get ready for bed."

"Yes Ms." I replied scooping up the nail polish and heading to the bathroom.

I looked at myself in the bathroom mirror trying to reassure myself. My reflection was exciting to me still no matter how scary things had become. Standing before me was a tall platinum blond in a white satin robe with a hot pink bra and white stockings. Of course, the reflection was tall as I had on 4 ½" white patent heels along with the previously mentioned hot pink thong. My chest was an inexpensive set of foam filled boobs that had a bit of an unnatural angle to them and no movement. Any time we went out I had to wear something that hid my cleavage entirely because they were not realistic at all. Just like that I'd gone from wondering how I'd make it through my guys week to wondering about getting a more realistic set of boobs! I shook my head in disgust then went about brushing my teeth and going to the bathroom before putting on the nightie Ms. Allison had laid out for me. For tonight it was a pale pink babydoll with a pair of matching sheer hipster panties. I walked back out to the living room, so Ms. Allison could look her selection over.

"Oh, I love that color on you!" She said with a wide grin. "It's so feminine I can't stand it!"

"Thank you, Ms." I replied as I felt my face turn bright red.

"Head off to bed muffin," she instructed, "I'll be up for a while longer."

"Yes Ms. Allison." I replied as I headed off to bed.

I was asleep by the time she came to bed. The next morning, I woke up 90 minutes earlier than normal which was one of the reasons I hated flying. In the bathroom Ms. Allison had laid out a nude camisole and white lace high cut bikinis for me to wear. I should have known I was going to wear lingerie, as the time had gone along the amount of male clothing I had kept decreasing. Outside of work clothing I had one pair of jeans, two pairs of casual pants, two t-shirts, and to pairs of boxers. I showered and shaved just as I would any morning, Ms. Allison had allowed me to skip my workout this morning thankfully. Dressing in the panties and camisole I headed to the kitchen to make a light breakfast. On the kitchen table was a note from Ms. Allison with instructions for the week.

"That surprise on Friday better be a good one!" I whispered to myself reading over her list.

Next to the list was the key locking the CB-3000 to my body, however, next to that were two numbered shipping tags that were in the shape of a heart. I was to put all three in my carry on then put the cage on as soon as I got through security. With only two tags I couldn't remove the first one until the end of the week when it was time to leave again. Looking at the door I saw my backpack, suitcase and garment bag all waiting for me. I made my way back to the bedroom and kissed Ms. Allison goodbye thanking her for packing for me.

"You're welcome sweetie," she said still half a sleep, "have a safe flight."

I returned to the kitchen and removed the lock to the CB setting it on the table next to the key. For whatever reason I waited until I got to the door and started putting on my boy clothing to remove the cage. The moment I took the cage off my clitty sprung to life quickly filling the front of my bikinis, much to my amazement it would stay that way for the entire 45-minute drive to the airport! I put on a pair of tan casual pants, a golf salmon colored golf shirt and casual shoes, grabbed my bags and headed out still not daring to look at what was inside them. Making my way through the security checkpoint I entered the men's room and into a stall. Taking out the cage and heart shaped plastic lock I put it back on then texted Ms. Allison a picture of my locked clitty. I felt silly sending a "dick pic" but it wasn't the prototypical one. Just as we were about to have to shut our phones off I received a reply from Ms. Allison.

"Have a safe flight and fun week girlie!" She texted.

Two flights later I landed at my final destination. Waiting in baggage claim I texted Ms. Allison letting her know I arrived then felt a hand touch my back, instead of wondering who it was my first thought was being thankful I wasn't wearing a bra under my shirt! It was Mike.

"Hey man how the fuck are you!?!" He bellowed in the crowded space.

"Great man," I replied much quieter than him, "how was your flight."

"Not bad," he replied in his typical bravado, "I think I coulda nailed one of the stewardesses if it had been longer."

"I don't think they do flights that circumnavigate the globe in one stop." I replied sarcastically.

I grabbed my bags while Mike stood in line for a taxi. Once at the hotel Mike and I dumped our bags into our rooms and headed to the bar. Eventually our group of friends got together and shot the shit catching up on what we'd done the past year since the last conference. By the time I stumbled back to my room it was pretty late, I texted Ms. Allison to let her know I was heading to bed, much to my surprise my phone rang immediately after.

"Did you have fun with the boys muffin?" Ms. Allison asked.

"Yes Ms." I replied feeling more than a bit of a buzz.

"Good! I packed you a lovely red nightgown to wear to bed tonight," she commanded, "tomorrow you will wear the peach lingerie I've sent with you as well. Understand?"

"Yes Ms." I replied opening my suitcase and seeing nothing but lingerie and heels.

"Oh, and whenever you are in the room you'll wear an appropriately coordinating pair of heels." She said with an obvious tone of superiority in her voice. "Do it now!"

"Yes Ms. Allison." I replied slipping on the 5 inch red patent heels.

"Good girl, text me in the morning after you're dressed so I can see how it looks."

Before I could respond she hung up. There was a two-hour time difference between her and I, and if it was late here it was even later there. I quickly brushed my teeth and put on my nightgown, so I could go do sleep. Unfortunately, the drinking I'd done caused me to be up a couple times through the night, which meant putting on my heels and toddling off to the bathroom. In the morning my alarm clock went off, as usual I got up on the first ring and grabbed my toiletry bag from my larger suitcase. I travel pretty often so to streamline the process I put my toiletries in my check bag. As I expected my toiletries were exactly what I had at home, it looked like I would not get a few days off shaving my legs after all. While I was getting ready I received a series of texts, some were from Mike and the guys about breakfast while others were from Ms. Allison about my week. She kindly reminded me that, just like at home, I would not be allowed to dress in my boy clothing until it was time to leave. Now dressed in my peach thong, garter-belt, tan stockings, heels and camisole I laid out my blue suit for the day. I didn't recognize the dress shirts that she had packed, most were softer colors. Finally I settled on a pale yellow one and a coordinating tie.

"Son of a bitch!" I hissed as I put on the dress shirt.

Most men don't realize this but there is little difference between a woman's collared dress shirt and a man's. The one difference between the two is women's dress shirts and blouses button from the opposite side. Ms. Allison had replaced my dress shirts with women's dress shirts, honestly, with a tie on no one would notice but it was still the mental reminder that she enjoyed dressing me as a girl. I finished getting ready and headed downstairs to breakfast with the guys. Other than not being able to use the urinal during breaks the day went just about as normally as other conferences in the past. At lunch we went to Hooters around the corner from the conference center. Mike always preferred so called breast-eraunts. At the end of the first day's session I got a call from Ms. Allison.

"How was your day baby?" she asked.

"It was good," I replied feeling a bit sheepish as people were milling around me, "thank you."

"Did you like your new shirts?"

"That was quite a surprise." I whispered. "I wasn't expecting that."

"Well I got bored and wanted to surprise you," she giggled, "I have another surprise for you in a couple days as well! One you are going to L O V E!" I could imagine what it was and hoped I was correct, I was horny and needed to cum! "Is Mike there this year?"

"Yes, he is," I replied, "he's actually walking up to me right now."

"Oh great! Put me on speaker phone!" I hesitated at this request. "Unless you want someone to walk into that room tomorrow and have an urgent message for amber you'll put me on speaker phone right now!" I gave in quickly considering she used my real last name after amber. "Mike how are you doing?"

"Hey Allie!" Mike beamed big as he spoke to her. "How's my favorite red head?"

"I'm doing well Sweetie," Ms. replied, "so was it Hooters for lunch or was it Twin Peaks?"

"You know me too well," Mike replied with a laugh, "and it was Hooters thank you very much."

"You are a predictable bunch," Ms. Allison laughed, "so is the strip club Wednesday night or Thursday?"

"Probably Thursday, why are you going to fly out and join us?" Mike teased.

"That's a long way to go to look at some fake boobs Mike," she quipped, "but make sure you get my guy a lap dance from a hot brunette, would you?"

"Oh, if you insist!" Mike said elbowing me as she spoke.

"Well he's had a tough few weeks and needs to let off some steam." Ms. Allison told him.

"Oh, I am sure I can make that happen!" Mike said with a wide grin and another firm nudge.

"Well just make sure those girls don't try to steal him away!" She teased before she hung up.

"I fucking love her," Mike laughed taking a big swig of his beer, "you'd better marry her before I do!"

The idea of Mike trying to marry Ms. Allison was quite a vision. Mike was 6'4 and built like a football player, he wasn't the type you'd put in lingerie. Then again, I hadn't thought I was the type you put in lingerie either and here I was with lingerie on under my clothes! Mike and I finished our drinks then parted ways. As soon as I got back to the room I called Ms. Allison.

"How was your day muffin?" She teased. "Are you dressed appropriately?"

"Yes Ms.," I replied dutifully, "bra, heels and wig."

"Good girl," Ms. said making me feel warm inside, "I've been bored without you here, who is going to clean up my toys?" I'm sure Ms. could hear my soft moan as my clitty swelled in my cage at the idea of her masturbating and being allowed to clean off her dildo with my mouth. "Listen to you getting all excited," Ms. Allison teased, "if only you knew how little I had on!" I couldn't hide my groan at her words as I strained against my cage.

"HEY!" I heard Mike pound on the door to my room. "Let's go there are single moms I need of our hard-earned money!"

"You'd better not keep him waiting," Ms. Allison laughed, "he may bust down the door and demand a lap dance!"

"Hang on Mike!" I called to the door. "What do I do Ms.?" I hissed into the phone already slipping off my heels.

"You put on pants, a shirt and regular shoes and go look at naked women!" Ms. Allison laughed. "You only get to take off one item of clothing so choose wisely!"

"Yes Ms. Allison," I answered quietly, "Mike give me a couple minutes I'm in the bathroom!"

"Hurry the hell up!" He replied.

Less than five minutes later I was heading out of the hotel room with a collared shirt, casual pants and shoes. Underneath I had on seamed lace top stockings, a lace thong and garter-belt and camisole. I was probably dressed in more lingerie than half the women I would be seeing! As usual the ride over was raucous with Mike taking the lead in driving up the excitement. I was sure he was 100% different at home and this was the one time a year he had a chance to really let his hair down. We made it to the strip club and inside where Mike got us a table practically in the middle of the action.

"Excuse me Ms.," he said flagging down a lovely brunette, "my friend's girlfriend said he needed a lap dance tonight, would you mind doing the honor?"

"Oh, I like a woman with confidence!" She said putting her hand on my shoulder.

Mike handed her the money and in an instant, I was being led off to one of the side areas reserved for lap dances.

"My name is Susan." She said with a smile.

"Hi Susan, my name is Robert." I replied sheepishly.

Susan had on a pair of white patent knee high boots with easily a 3" platform, white high waisted booty shorts and a matching crop top that barely contained her white lace bra or their contents.

"Why don't we sit over here until the next song starts." She said leading me to a long bench.

At the far end of it a gorgeous blonde was giving a lap dance to another man. I envied her ability to move her hips the say she did in the heels she had on. While I was lost for a moment Susan put her hand on my right thigh, right on a garter clasp, as she sat next to me. She made some small talk that I barely paid attention to as I was more concerned about her hand than anything else. Somehow, she seemed not to feel the clasp, I think it was right in the palm of her hand but because of its relaxed position her hand hovered barely above it. As the song that was playing ended Susan shifted to get up placing two of her fingers directly on the clasp. I felt my face flush deeply as she looked down then up at me.

"Some kind of medical condition you want to tell me about before we start Robert?" She asked running her fingers around the clasp.

"Ummm, no medical condition." I stammered suddenly feeling incredibly warm. "It's okay if you don't want to do this, we can just tell my buddy that you did."

Susan followed the clasp to the strap that attached to my garter-belt slipping a finger under it through my loose-fitting pants. She lifted it up letting the strap snap back to my skin then followed the clasp to my leg where she could obviously feel the lace top stocking I had on.

"What do you want to tell me Robert?" She said raising an eyebrow at me.

I could feel my cheeks burning bright red as I tried to think of something to tell her.

"I um, my um, it is kinda ..." I couldn't find the words to explain anything.