Discovering Amber Ch. 05

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Ms_Allison
Ms_Allison
1,370 Followers

"A year or so ago," Ms. Allison said as she walked around me and sat on the bed close to Ms. Jenn, "my boyfriend decided I needed a new bikini and picked this up at sluts-R-Us." Ms. Allison sipped her coffee as I struggled to put the top on. "Needless to say I only wore it once," she said between sips, "but not outside."

"Oh, but you'd look great in that," Ms. Jenn added, "I mean, look what it's doing for her!"

"True," Ms. Allison said setting her coffee aside and helping me with the top, "just imagine if you had real boobies though." She tugged the small triangle cups in position over my bare chest as she spoke. "Something big enough to all but spill out of these little cups," she said with a gleam in her eye, "with nice hard nips to announce your presence." Ms. Allison giggled then rubbed the front of my tiny bottoms with her left hand. "I tell you sissy," the gleam in her eye was bigger now, "if we ever hit the lottery you're getting bigger boobs than me!"

"So, what is your plan for today?" Ms. Jenn asked as she slipped off the bed and readjusted her robe.

"Well we have time to kill today," Ms. Allison said taking Ms. Jenn by the arm and walking her out of the bedroom while summoning me to follow with a finger, "and it's supposed to be wonderfully warm today." I followed them down the hall to the living room feeling oddly overdressed in my tiny two piece. "Lot's of sun today too," Ms. Allison continued then turned to me to add, "grab the big towels from the closet." I removed six beach size towels from the closet following them to the kitchen where the deck was located. "So, I thought we'd all lay out and tan for a while."

My stomach sunk again. Outside? Like this? Tanning! Granted my gym membership was cancelled the second day of my sissy transformation. It wasn't like I could go into the men's locker room with panties and painted toenails after all! Now Ms. Allison was going to remove my tan-lines and make them more feminine as well! My arms from the upper arm down were tanned in a traditional farmers tan as were my legs from my shorts to my feet. That would definitely change in my skimpy bikini!

"amber I want you to set up the lounge chairs on the deck," Ms. Allison instructed, "just three of them tough, then lay a towel on each one."

My hand shook as I went to open the sliding glass door to the patio. I was wearing 4" heels, still had on my frilly ankle socks and wig, as well as my teeny tiny bikini as I stepped out onto the deck. Desperately trying to hide my bare ass from the building that faced ours I opened the chairs awkwardly, finally getting them in place. With the towels over the backs of the chairs I informed them that they were done.

"Put three towels over the railing on the far side," Ms. Allison said as she relaxed in a nearby chair watching my progress, "so that Jenn and I can lay on the two end lounge chairs and not be seen by people across the way." I did as she instructed laying the large towels over the railing. "Very nice," Ms. Allison said as she walked out then sat on the lounge chair farthest from the door, "go in the top drawer of my vanity and get the tan bottle."

As I went to the bathroom Ms. Jenn passed me in the doorway and gave my crotch a slight squeeze. I moved as quickly as I could in my heels to her bathroom to retrieve the bottle she wanted. Returning I almost dropped it as she and Ms. Jenn were now lying completely naked on their lounge chairs! Ms. Jenn was face down with her head turned toward me and her magnificent bottom all but beckoning me while Ms. Allison was laying on her back watching my every move intently.

"Don't just stand there and drool," Ms. Allison said sharply, "you need to put lotion on us!"

"You don't want my ass to burn do you?" Ms. Jenn asked while winking at me.

The fact I was outside, in full view of the building across the parking lot and the 80 some odd people that lived there, no longer bothered me. Ms. Allison had me pour lotion into her hands, so she could rub it on her front while I rubbed the lotion onto Ms. Jenn's body all the while standing bent over at my hips so my lily-white ass stuck high in the air. After they were slathered in oil I lay on my chair, removed my heels and socks, then did my best to relax as the sun did it's best to remove my masculine tan-lines. As I was closest to the door, and the bottom of the ladder, I was in charge of getting drinks, reapplying lotion and doing whatever else needed to be done. My initial humiliation of being outside while stuffed into a two piece had disappeared as I was regularly rubbing lotion on Ms. Jenn and Ms. Allison. My poor crushed sissy tessies were unhappy as the seemingly constant lotion rubbing had me quite horny.

"I think I'm done." Ms. Jenn eventually said. "Plus, amber has me so oiled up I don't know if this will come off in the shower!"

"Me too," Ms. Allison added as she reached for her robe, "stay right there though amber, you're not done yet." I wasn't sure what to make of her statement but soon couldn't think of anything as both of them applied lotion to my body. "We'll give you a few minutes," Ms. Allison whispered huskily near my ear, "then have you roll over so we can do your back too. I want you nice and tan so this will be a regular thing this summer."

Just as quickly as they'd started rubbing me they stopped then got up leaving me alone. My body was on fire and not from the sun! When they returned it only got worse as they spent little time applying lotion to my back and legs instead focusing most of their attention on my ass.

"Relax for a moment." I heard Ms. Allison say softly.

While I was quite relaxed the pressure of something against my puckered hole made me momentarily tense. I was able to control it quickly as I felt the familiar smoothness of a vibrating egg being pushed inside me. No sooner was the egg all the way past my inner rings did I feel the vibrations start to pulse through my lower body.

"I don't want you to be bored while Jenn and I shower," Ms. Allison said turning the controller up to the max, "together." I couldn't help but let out a little groan at the idea of them together in the shower.

I have no idea how long it was before they collected me from the deck, but I was so wound up it wasn't funny. I'd done little else but picture the two of them in all kinds of sexual positions in the shower while my ass buzzed on high. When they let me into the condo their appearance didn't help. Both had their make-up and hair done to absolute perfection, both wore different black bustiers, Ms. Allison's was leather with a black zipper up the front while Ms. Jenn's was satin with lace panels on the sides making a V of the satin front. Both of them had on black stockings, thongs and heels as well, they looked so amazingly Domme-like I all but fell on my knees to beg them to be allowed to serve.

"Time to shower sissy." Ms. Allison instructed then moved out of the way so I could walk down the hall to my bathroom.

"Hold on a second," she said stopping me in my tracks, "did you notice something?"

In the hallway there was an inexpensive full-length mirror, on that mirror was one of the suction cup based dildos we'd purchased weeks ago. When Ms. Allison had started my oral training, she positioned these all around the condo, whenever I passed one I would have to suck it taking it as deep as I could into my mouth 10 times. This one was low enough that I would have to kneel as I serviced it. As I knelt Ms. Jenn and Ms. Allison stood behind me, so I could see them in the mirror as I wrapped my lips around the latex head of the dildo. They offered words of encouragement as I touched my nose to the mirror 10 times before asking if I was allowed to stand. Another dildo was placed in my bedroom, one in the bath, the kitchen, and two in the living room. I could barely go more than 30 seconds without having my lips around a latex shaft all the while my ass buzzed away and sissy clitty dripped like a faucet. Over the course of the next hour I showered and shaved before being dressed in a pale pink panty and bra, my fake boobs, suntan back seamed lace top stockings and black 5" heels. The only time my plug was turned off was when we sat for dinner, during which, they talked openly about their past sexual experiences with men and each other. I knew that if I wasn't allowed some kind of relief soon, I was going to explode!

"How about an adventure tonight amber?" Ms. Jenn asked out of the blue as I finished cleaning up from dinner.

"I'd love it!" I blurted hoping the adventure would mean I get to cum.

"You've been out while dressed before, right?" She asked happy with my excitement.

"Yes," I replied still excited about the possibility of an orgasm, "just drives here and there or walks in secluded areas."

"I'd love to see that," Ms. Jenn replied with a wink, "we just need to finish getting you all dolled up!"

Ms. Jenn and Ms. Allison led me back to my bathroom, past 4 of the dildos along the way, to help me get ready. They picked a long, straight brunette wig, a deep red lipstick and had me put on my make-up a bit on the "slutty side" as they described it. When I finally got to look at myself in the mirror I was floored! Finally, Ms. Allison added a mock turtleneck, sleeveless minidress with a snug fit all the way to the flared bottom of the drop waist which hid my sissy clitty perfectly. The black dress had some sparkle detail which highlighted my breasts perfectly and fell maybe 2 inches below the bottom of my lace stocking tops. Whatever necessities I was deemed to need were put in a small clutch which matched my dress. With the plug at half speed we exited the condo before I really knew what was going on. The sounds of three pairs of heels echoed in the hallway. Ms. Allison now had on a black leather pencil skirt and bright white blouse which showed just a flash of her leather bustier while Ms. Jenn wore a deep purple dress with a keyhole front revealing just a bit of her cleavage as well. They both looked stunning, but as I looked in the mirror polished doors of the elevators I saw that I practically fit in with them!

"You look amazing amber!" Ms. Jenn said as I felt her hand glide up my back.

"Thank you, Ms." I replied blushing deeply.

We proceeded to Ms. Allison's car, where I got into the relative safety of the back seat which had tinted windows. As we drove I gradually relaxed as the night sky got darker and the road's vibrations coupled with the egg provided more than enough distraction.

"Are you ready for challenge number one?" Ms. Allison asked as I realized we'd stopped in a convenience store parking lot.

"Ummm," I replied trying to come to grips with what challenge one would be, "yes, Ms. Allison."

"It will be easy and we will be right here," she said touching my leg softly letting her fingernails tickle my stockings, "you know I won't let anything bad happen to you."

They laid out the challenge for me then had me repeat all the steps back to them before sending me on my way. I tried to be as confident as possible as I exited the small SUV and walked to the store's entrance. Behind the counter was a younger man, maybe 21 years old, who looked me up and down as soon as I entered. I gave him a slight smile and was greeted with "What's up Baby?" Obviously, he had no idea I was not quite a baby, but I was fine with that. His compliment gave me a bit more confidence as I found the aisle with the candy bars in it. Looking slowly at the selection I stood with my back to him, standing on one leg and crossing the other in front of it to try to show off a bit of an hourglass figure, before determining what candy bar I was going to buy. Step two of the challenge was to select a candy bar from the bottom shelf, step three was to get it. Step three should have been easy but there was a serious caveat to it, I would have to bend over with my knees straight and my feet together giving the clerk an unadulterated view of, well, just about everything! I prayed that I would not hear him scream as thoughts of my sissy tessies jumping out from between my legs filled my mind. Bracing myself with one hand, in case I fell or needed to run, I slowly leaned forward until the candy bar was within easy grasp.

"Woah!" I heard from behind me.

Obviously, he hadn't been greeted by my anatomy and instead enjoyed the eyeful of legs and butt he got to see. I walked to the register and gave him another smile as I put two dollars and the candy bar on the counter.

"Thank you for that!" He said obviously turned on by my slutty display.

I panicked at that point. While I could pass, at least as far as this kid was concerned, we'd never worked on my voice! The last thing I wanted was to ruin this moment with the crackling voice of a pubescent boy! Rather than speak I pursed my lips touching my right index finger to them as I made a kissing sound, then I reached over the counter pressing my finger to his lips before giving him a wink. I felt the heat of his lips on my finger as he kissed it. Not knowing what to do next I turned and walked out barely remembering to keep my clutch my hand but leaving the candy bar and the money for it on the counter. I all but dove into the backseat of the SUV to a howling Ms. Allison and Ms. Jenn who quickly pulled out of the parking lot before I was followed. Their laughter only intensified when I told them I'd left the candy bar and money on the counter and what I'd done to distract him from my not wanting to speak!

"Oh, I think he's definitely going to be jerking off to you later amber!" Ms. Jenn blurted between laughs.

"Think so?" I asked suddenly shocked at the thought that a guy would jerk off while thinking of me and wondering why I wasn't disgusted about that in the least.

"Does that excite you baby girl?" Ms. Allison asked all of a sudden sounding a bit serious.

"Yes, Ms. it actually does." I replied. "I heard his reaction when I bent over," I continued, "he was checking me out and liking what he saw."

"I told you that you were totally fuckable amber!" Ms. Jenn laughed carefully wiping tears from her eyes.

"Ready for challenge number 2?" Ms. Allison asked.

"Yes, I am Ms.!" I replied feeling full of confidence.

"Good," she replied eyes wide as they looked at me in the rear view mirror, "if you thought that guy was good just wait until we get to the next stop!"

Before I could think about it too much the egg in my ass went all the way up filling me with vibrations. I sat back into the seat loving what I'd just experienced as well as the egg filling me with it's buzzing. Instead of contemplating what was possibly coming next I sat back and thought about the clerk running out back of the store to rewind the security tape and watch me flash him my ass again and again while he stroked his long, fat cock. I shock my head for a moment wondering why I was so intrigued about the idea, why I was thinking about him having a long, fat cock. Then we hit a bump, the egg jumped inside me, and I no longer cared why I was thinking about him beating his meat to my ass. What better thing for him to jerk off to than me? My mind raced to an image of me, hidden behind the counter on my knees stroking him while he tried to appear normal to the customers he was helping. My body trembled at the idea of jerking the clerk off! I'd never felt like this before, it was new and scary but so very exhilarating! My mind had started to wonder how much different his cock tasted from the latex dildos I'd been sucking all night when we stopped again. Across the street I could see a red neon sign with the words "The Dancing Red Whale" and a cartoon whale with a top hat and cane. Whatever it was, we were here.

"Okay muffin," Ms. Allison turned in her seat to face me, "this place has something called an alternative lifestyle night, which just so happens is tonight." I nodded unable to take my eyes from the neon red whale. "There are people inside who are accepting of genetic males who dress up in lingerie and heels," she touched my leg with her hand pulling my eyes to her, "so there will be no problem when we go in there provided you are brave enough to do it." She no longer referred to me as a man as a real man would not dress like a girl, in her mind all sissies were genetic males and not men, it was wonderful reinforcement. "But, if you are brave enough to go in there," she continued, "there are rules you will follow, understand?" I nodded and whispered my consent. "In college Jenn and I would go to a fun club like this because we could dance and not worry about getting hit on all night," Ms. Allison said squeezing my leg, "it was always a lot of fun." I nodded again. "With that in mind," Ms. Allison continued, "if we go in there you can expect that you'll be asked to dance by a man." My eyes shot to hers as all I could picture was slow dancing with a huge man grabbing my ass. "You don't get to say no either," Ms. Allison said, "unless they try to get inappropriate."

"Inappropriate?" I stammered.

"Yes," she said calmly, "like if they try to reach up your skirt or something."

"Or ask you back to their place." Ms. Jenn added with a chuckle. "I did mean it when I said you were fuckable!"

"Thank you, Ms." I replied wondering if the sentiments of the guys inside the Dancing Red Whale would be the same as Ms. Jenn's.

"So, what do you say amber?" Ms. Allison pressed. "Did we get dressed up for nothing or are we going out for a girl's night of clubbing?"

I swallowed hard, my mind was racing. It was a gigantic step for me, I was going to be OUT as amber and not just for a quick trip to the mall. This was a night out with the "girls", I'd be dancing with guys who liked, well, guys!

"Okay." I said softly, almost automatically in spite of my reservations.

"Great!" Ms. Allison quickly turned to shut off the car while Ms. Jenn was already getting out.

They were moving quickly, in an instant I was out of the car as well. Three sets of heels sounded like cannons as we crossed the street. The neon red whale kept getting closer and closer as I was seemingly on autopilot with my arms locked in theirs. Ms. Jenn opened the door while Ms. Allison slipped her arm from mine and pressed her hand on my lower back to push me inside. I all but fell into the doorway and was soon standing in front of a rather buff looking man. He had on black pants and a white shirt with several buttons undone showing off a deep tan.

"ID's please ladies." He said while looking us up and down.

I panicked as I reached into my clutch. I didn't have an ID that had amber on it, my ID was me with a bit of facial scruff, a white shirt and a tie. Would he even let me in? My fingers trembled as I pulled my driver's license and handed it to him. By this point Ms. Allison and Ms. Jenn had already given him their ID's and gotten them back. He surveyed me as I finally managed to hand my license to him.

"You do clean up nice," He said with a wink as he handed me my license back, "I think I prefer you this way more, enjoy your evening."

"Thank you." I could feel my face and chest turning red.

They quickly ushered me inside as I began to wonder, was the doorman hitting on me? How many more men would prefer this look to the scruffy faced look of my driver's license? No where in my line of questioning was I wondering why I wanted to be considered attractive as amber or why I was okay with being hit on by men! I followed Ms. Allison and Ms. Jenn to a pub table where I was given the tall chair closest to the outside while they sat against the wall. The thumping music only added to the egg vibrating deep inside me. When the waitress came Ms. Allison ordered the drinks, a few minutes later I had a shot glass with blue liquid and a dollop of whipped cream on the top as well as a tulip glass filled with icy purple liquid with a straw and an umbrella.

Ms_Allison
Ms_Allison
1,370 Followers