Discovering Amber Ch. 05

Story Info
A day of teasing turns into a very wild outing.
7.8k words
4.64
34.5k
22

Part 5 of the 9 part series

Updated 06/09/2023
Created 03/19/2011
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Ms_Allison
Ms_Allison
1,362 Followers

Mistress notes:

To say both amber and Jenn were surprised when Jenn entered my condo would be an understatement. I had given Jenn "some" warning as to what she might find, but she was expecting me to be dressed up for her not amber. Poor amber had the biggest crush and attraction toward Jenn as well, it was hard not to though, Jenn is gorgeous! It was time for amber to go a bit more public with her sissy-side and Jenn was the perfect person to help with that. She always loved to flirt, and the fact that amber couldn't really do anything about it made flirting that much more fun for Jenn. The fact that amber loved the attention and embarrassment that went along with it didn't help her cause any either.

Ms. Allison

~~~~~~~~~~~~~~~~~~~~~

As I stood dutifully nearby I listened to Ms. Allison describe my transformation to her friend Ms. Jenn who kept looking me up and down. Both women were casually dressed in jeans and loose-fitting tops with bare feet while I was dolled up in my French Maid uniform teetering on 6" heels. As Ms. Allison spoke about the evening she made me throw away all of my, as she liked to call it "ugly boy underwear", I felt as if my sissy clit was starting to retract into my body. Unfortunately, as it continued to get smaller the deluge of precum continued. I was thankful for the very full petticoat which hid the giant wet spot that was overtaking my frilly panties.

"Well I do have to admit," Ms. Jenn said as her eyes roamed my long stocking clad legs, "he, I mean she looks pretty amazing!"

"My little amber has been working quite hard," Ms. Allison spoke of me with great pride which thrilled me, "she's even mastered walking in those heels as well as a few other things."

"Oh really!" Ms. Jenn now looked me straight in the eyes as she spoke. "Do tell amber," she said with a gleam in her eye, "what else have you mastered?"

"Ummm, Ms. Jenn," my voice crackled like a pubescent teen as I tried to speak, "I do my own make up, and shaving, I um, I am learning to cook and do well in my heels."

"Go get your boyfriend amber." Ms. Allison said abruptly cutting me off.

"Yes, Ms. Allison." I replied sheepishly while feeling my face turn beet red.

"BOYFRIEND?" Ms. Jenn all but shouted.

"Oh, wait until you see!" Ms. Allison gushed then looked over at me, "Move your sissy ass before I put you over my knee!"

Gulping I quickly made my way out of the living room while the two of them laughed behind me. Ms. Jenn seemed quite excited about the idea of witnessing corporal punishment! The idea of having my petticoat lifted and panties yanked down while over Ms. Allison's lap was exciting and scary. We'd never had another person in our "play" and the idea was very arousing to me. I entered my bedroom and headed toward my nightstand, there in a prominent spot was what Ms. Allison referred to as my "boyfriend." The 7" realistic dildo had balls and a suction cup base. Each night before bed I would kiss my boyfriend goodnight and upon waking would kiss him good morning. Whenever I watched what Ms. Allison called "training videos", which was sissy porn, I did so with my boyfriend. During blow job scenes I would practice on him as well, Ms. Allison would often smear my seemingly endless stream of precum on the head and shaft for me to lick off as well. Over the months of oral training with my boyfriend my body had learned to simply react at the sight of him, just picking him up from the nightstand had caused my mouth to start watering and tessies to tingle. I walked back to the living room holding him with two hands in front of me as if carrying something sacred. Instead of retracting into my body my sissy clit was now straining at the cage that held it, which was another bodily reaction to holding my boyfriend. Over the months since this journey started Ms. Allison would make sure that I learned to associate dildos, particularly the one being cradled in my hands, with pleasure. For weeks, whenever I stroked or sucked a dildo, Ms. Allison would make sure to tease me and keep me aroused until, just like my mouth starting to water on its own, the sight of my boyfriend aroused me. My body, and my brain, had been trained to love cock to the point that just the word cock or thought of a cock made me tingle inside.

"Holy shit," Ms. Jenn blurted as I moved back in front of them, "I can see what you're saying about the glassy eye look!"

"Yup!" Ms. Allison said triumphantly. "My little sissy loves her boyfriend! Don't you muffin?"

"Yes, Ms. Allison," I replied with a smoothness to my voice emphasizing my state of arousal, "I do."

Another "step" in my training was the introduction of pet names that could only be applied to those of the female gender. Ms. Allison would not use sexual ambiguous pet names like Honey, Babe, or Sweetie, preferring terms like muffin, or "my little girl" or even "my sweet sissy" instead. From the moment I set foot in the condo after work until the moment I left for work the following day I was totally immersed in being a sissy. There was no escaping it, I lived every non-work moment as a girl, a very horny girl with very slutty tastes in clothing and movies. Truth be told I loved it all! Being called those silly pet names simply warmed my heart to the very core.

"Put him down on the coffee table," Ms. Allison said shifting to face the table in front of her and Ms. Jenn, "and show Ms. Jenn what you've learned."

I placed the dildo so the suction cup base adhered to the glass top then knelt in front of it, and them. My chest pounded with excitement as the humiliation and idea of showing off my oral skills consumed me. Without thinking I licked my lips as I lowered my mouth to my boyfriend.

"Holy shit!" Ms. Jenn exclaimed as my bright red lips wrapped around the bulbous head. "He's really going to do it!"

"She Jenn," Ms. Allison corrected, "my amber is as girlie as they come, isn't that right muffin?"

"Yes, Ms. Allison." I replied lifting my mouth free for a moment.

"Now show Jenn how good you are at this," Ms. Allison ordered, "suck it like a pornstar!"

I didn't need any encouragement, I'd wanted the dildo in my mouth since the moment Ms. Allison had ordered me to get him from my bedroom! With the index finger and thumb of my right hand holding the base and my left hand massaging the big latex balls my mouth and tongue worked the shaft while the world around me disappeared. I sensed Ms. Allison moving but focused on my task taking more and more of the shaft into my mouth and throat until my nose bumped the glass table top. She spoke from behind me, her words were soft and encouraging but I was too focused to hear her. I felt a hand on my back, then her other hand started to massage my swollen tessies through the thin material of my panties. I groaned then redoubled my efforts as she again reiterated the concept that a phallus in my mouth went along with physical pleasure. My body shuddered as Ms. Allison pressed her thumb against my tight hole while pushing on my upper back to hold my boyfriend deep in my mouth. By the time she let me up I was lightheaded from the lack of oxygen.

"That's my good little cock sucker," Ms. Allison said proudly as I sat back on my heels, "you could make any man happy with oral skills like that!"

"Thank you, Ms.!" I replied breathlessly.

"Well I'm impressed," Ms. Jenn said unable to hide her look of shock, "I think you do better at that than I do!" I blushed at her compliment. "I know I have never been able to deep throat anything!"

"Well amber had a bit of motivation in that department didn't you sweet sissy?"

"Yes, Ms. Allison," I replied wondering if I'd ever stop blushing, "you did."

"Tell Ms. Jenn your motivation." Ms. Allison continued.

"My sissy clitty is locked in a cage," I started knowing I wouldn't stop blushing soon, "and Ms. has the key. In order to be allowed a real orgasm I had to prove I could suck cock like the videos I watch." The shocked look on Ms. Jenn's face wasn't going to leave soon either as I continued. "I practiced every night for hours for two weeks until I could finally touch my nose to the glass," I felt my clitty straining against the cage thinking about it, "until finally I could touch my nose ten times without pausing."

"Holy fuck Allie!" Ms. Jenn blurted.

"I know right!?!" Ms. Allison replied. "Do you enjoy being amber though muffin?"

"Yes, Ms. Allison," I replied sincerely, "I truly do!"

"Take your latex lover back to your bedroom," Ms. Allison said handing Ms. Jenn a glass of wine, "I left something out for you to wear to bed in your bathroom. Go get ready for bed."

"Yes, Ms. Allison." I replied dutifully picking up the dildo before mincing back to my room.

While I could hear their conversation, I could not make out what was being said. What I could make out from the tone was Ms. Jenn's confusion about our relationship. Many people don't understand what it is to be a sissy. Honestly, I didn't at first either, but since going down this route I am thrilled with every turn it has taken. When I get home at night I change into a different person, one who is controlled and does whatever task that is given happily and without hesitation. I get to shut my brain off and let Ms. Allison "drive". The weekends are the best as I am en femme from Friday afternoon until Monday morning, even wearing fake nails all weekend long. I become someone else entirely, someone devoted to pleasing and other's pleasure. That is where I get my enjoyment.

I put my boyfriend down on the nightstand, planting a soft kiss on the tip, before reluctantly removing my dress and petticoat. Catching a glimpse of myself in the mirror the front of my thin white panties was almost translucent with my precum. Slipping a finger inside them then bringing it to my mouth I tasted myself, another thing that I'd gotten used to over the months. I now thoroughly enjoyed my own taste. Placing my wig on one of the heads in the closet I made my way to the bathroom to wash off my make-up. I couldn't help but notice Ms. Allison's choice for bed, Ms. Jenn would easily see my cage in what she picked out for me. With my usual night-time ritual done I removed the corset, panties, stockings and heels in that order. My feet were not bare for long as I slipped into a pair of 4" slippers before stepping into my selected bottoms. Pulling on the top I stepped in front of the full-length mirror to give myself a once over. Bed time was the only time I looked less girlie, not only was I was devoid of make-up and wig many of my bed time tops did not hold my breast forms properly. Thankfully this one did so from my shoulders down I looked fairly femme. The canary yellow fly away babydoll top had a built-in satin pushup bra with a 1" pink ribbon tied neatly in a bow in the front. The tails from the ribbon fell to my waist along with the sheer material of the babydoll. As I stepped or moved the light material would sweep to the side exposing my tummy and the matching sheer thong bottoms which also had a small pink bow. Ms. Allison entered the room behind me then went to one of my dressers.

"One more thing for tonight my pet." She said handing me a pair of yellow ankle socks with ruffles around the cuffs.

"Thank you, Ms." I replied as I went to put them on.

"I'm very, very pleased by your performance tonight," Ms. said as she sat next to me on the bed, "you did very well. I'm very proud of you amber." I thanked her as I put on my socks and heels. "Are you okay with everything?" She asked showing obvious concern. "I know it was a bit of a surprise."

"I was shocked at first," I said feeling the flush of embarrassment come over me again as I thought about Ms. Jenn finding me dressed up, "but it was only a matter of time before someone else saw me dressed. I'm glad it was her. Is she okay with it?"

"Oh, she is," Ms. Allison said with a chuckle as she touched my leg, "let's just say this wasn't exactly the picture she had of you." I blushed again. "Now come out and say goodnight to our guest," Ms. Allison said as she stood, "you should probably know she is spending the weekend."

"Does she need my bed?" I asked panicked at the idea that Ms. Jenn would sleep on the couch. "Honestly I can sleep on the couch instead of her."

"Oh, you silly sissy," Ms. said cupping my face and lightly kissing my cheek, "in the morning when you bring my coffee and breakfast, bring enough for two."

It took me a moment to process what I'd just been told. I could not for the life of me understand where Ms. Jenn was sleeping and why I would need to bring Ms. Allison breakfast and coffee for two in the morning. Eventually it hit me, I had no idea that Ms. Allison and Ms. Jenn had any kind of a relationship outside a friendly one. Wait, did they? Were they? I shook my head to clear it of thoughts a sissy didn't need to know before walking out of my bedroom to the living room. Things, for the first time that night, regarding Ms. Allison's and Ms. Jenn's relationship became much clearer.

"Oh my God she has a belly ring too!?!" Ms. Jenn said almost choking on her wine. "Honestly, where does this stop?"

Ms. Allison was sitting in the corner of the couch with her feet up on the coffee table, Ms. Jenn was tucked under Ms. Allison's left arm snuggled closely to her. They looked every bit the couple as I stood in front of them in my sheer outfit.

"I'll have to tell you about when we got it pierced later," Ms. Allison said proudly before sipping her wine, "amber was quite the hit!"

"I am sure she was!" Ms. Jenn giggled as she rested her had on Ms. Allison's shoulder.

"Turn around so we can see the rest of your outfit muffin." Ms. Allison ordered.

"Oh, that is sexy," Ms. Jenn said suppressing a laugh, "what a cute little bottom you have amber."

"Thank you, Ms. Jenn." I replied as I turned back to face them.

"Sweet dreams amber." Ms. Allison said warmly while giving me a wink.

The wink was akin to a buddy saying goodnight, so he could spend alone time with the girl he'd brought home. It was just then that I noticed Ms. Allison's left hand was softly rubbing the side of Ms. Jenn's left breast through her top. The look on Ms. Allison's face was similar to one I used to get from my old college roommate on nights he knew he was going to get lucky with a girl. Ms. Allison was going to get lucky! With Ms. Jenn! Was she a lesbian? I mean bi? Where they both bi? My mind raced as I walked to my bedroom. Laying in bed I could hear their hushed conversation; their voices had a far more intimate tone to them than earlier in the evening. I was still awake when they walked hand in hand slowly past my room on the way to Ms. Allison's bedroom.

The next morning, I woke up thankful it was Saturday. Saturday's meant I could sleep in, as much as my cage and clit would allow, and I wouldn't have to worry about a workout. Ms. Allison had a nice selection of workout videos for me from yoga to strippercise to Pilates depending on her mood. I slipped out of my bed, and into my heels, before heading off to the bathroom where more good news awaited. Ms. Allison hadn't laid anything out for me to wear which meant Saturday morning would be spent in the clothing I'd slept in! All I had to do was add an appropriate wig and light make up! Walking into the kitchen I found a post-it note on the coffee maker stating Ms. did not want coffee before 9. Obviously, she wanted to sleep in as well. This allowed me time to make my own small breakfast and have coffee while looking out the sliding glass door to the small deck and beyond. I'd often considered stepping out onto the deck dressed as amber but hadn't managed to be that brave just yet. Lost in my thoughts my morning flew by until it was time to bring breakfast to Ms. Allison and Ms. Jenn. I placed their breakfast and a small pot of coffee on the tray then made my way down the hall to Ms. Allison's room where I managed to softly knock on the door while not spilling the tray.

"Come in sissy!" Ms. Allison called from inside the bedroom.

"Thank you, Ms.," I said entering the room and trying to hide my surprise, "I have your coffee and breakfast."

"Set it down on the nightstand muffin," she said adjusting the sheet which was barely covering her bare chest, "did you eat already?"

"Yes Ms.," I replied looking at Ms. Jenn's bare legs which were sticking out from under the sheet, "I did eat already."

My eyes kept traveling up Ms. Jenn's body to her bare arm and shoulder until I saw that she was staring back at me.

"Like what you see sissy?" She asked raising an eyebrow at me.

"You're very beautiful Ms. Jenn." I stammered.

"You're not just saying that because I'm naked, are you?" She asked as she sat up in the bed taking just enough of the sheet with her to cover her ample chest.

"No, uh, no Ms." I replied unable to pull my eyes away her moving body.

"Get my purple robe sissy," Ms. Allison said almost scolding in her tone, "and try not to drool all over your tits."

"Yes, Ms." I replied fetching Ms. Allison's robe from her closet.

I held the satin robe by the collar and shoulders holding it open for Ms. who was already slipping out of the bed. Ms. Allison slid her arm into one sleeve then the other allowing me to pull the robe over her shoulders. I retrieved a second robe for Ms. Jenn and repeated the process. Each of them made their way separately to the bathroom then relaxed on the bed so I could serve them coffee and breakfast. The addition of the robes, both made of thin satin with lace, made concentrating and keeping my sissy clitty under control quite difficult.

"You know what we should do!" Ms. Allison said as she slipped off the bed. "Oh I have such a great idea!"

"What is it?" Ms. Jenn asked.

"It's going to be warm and sunny today," Ms. Allison replied as she rifled through one of her dresser drawers, "and someone needs to work on their tan lines!" I felt my stomach sink as she looked at me. "Strip sissy!"

Her simple command sent my mind racing. It was one thing to be dressed up in the slutty nightie I had on with Ms. Jenn here but now I would have to take that off too! I didn't dare show my hesitation though and dutifully removed my top. Out of the corner of my eye I could see Ms. Jenn's eyes were focused on me as I undressed. In spite of my pending embarrassment my clitty was still fighting for space inside my cage! I pulled my bottoms down, stepping out of them before trying to stand calmly in front of them. It wasn't easy. The silence didn't help. Finally, I had to lift my eyes to see what Ms. Jenn was doing.

"I know I saw most of this last night," she started with a tone of shock and amusement, "but honestly this is quite a sight." Ms. Jenn covered her mouth while looking me up and down again and again. "I mean," she stammered again then picked up speed, "between the belly ring, that cagey thing, and a landing strip above it!" She suppressed a laugh before continuing. "Tell me you don't have a tramp stamp too!"

"No, Ms." I replied meekly, "no tramp stamp or tattoos."

"Oh well thank God," Ms. Jenn moved showing far more of her cleavage as the robe fell more open, "I'd honestly pee myself laughing if that were the case!" Ms. Jenn sat back hiking up one leg which caused the bottom of her robe to fall open a bit revealing part of her shaved mound. "Oh, Allie I don't know how you did it," Ms. Jenn said taking her coffee cup in her hand, "but in the right light your little amber here is downright fuckable!"

"And you think I just say that as a compliment," Ms. Allison said giving my left ass cheek a smack, "here you go, put these on before you make too big a puddle on the floor."

Ms. Allison had handed me a green floral bathing suit bottom with a thong back and plunging front. Still standing in my heels I carefully stepped into the bottoms then pulled them into place. The front was barely enough to hold me in place and cover me, the sides of the eye-patch front didn't even touch my skin. Ms. Allison gave the back a bit of a tug then adjusted the side string straps of the bottoms on my hips to insure they were in place. She then handed me the string bikini top.

Ms_Allison
Ms_Allison
1,362 Followers