Discovering Amber Ch. 03

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Ms_Allison
Ms_Allison
1,370 Followers

"Lay on the table and roll up your top." He instructed as he sat with his back to us.

I did as I was told and pulled up my shirt so it was just below my bra. Ms had to help me as my hands didn't seem to want to stop shaking. She held my hand and looked down at me mouthing to me that everything would be okay. For as scared as I was her telling me that helped and I slowly calmed down.

"You ready sweet heart?" He asked rolling over to the table in his stool. I just nodded as I was still to afraid to speak. "This'll hurt just a bit."

He swabbed the area to sterilize it and then covered the skin around my belly button. I was happy that my stomach was relatively flat. He then did something to numb the area just a bit before I felt the pinch, pressure and then sting of the piercing. It was much different than when I had my ears done and I couldn't see how guys had this done to their peckers. Thank God Ms Allison didn't want that done!!!!

"There you go," he said sitting back and taking the paper away, "all set."

"Thank you." I replied softly taking a mirror from him to inspect the piercing.

It was a small red heart that looked like a diamond. The gem was obviously costume jewelry but Ms was right, it did look very cute. I carefully got off the table and followed Ms to the counter where she paid cash for the piercing. She picked up some cleaner to help keep me infection free and led me back out to the car. I had to be careful when I sat because anything bumping or rubbing against the piercing would hurt. As she drove I tried to relax but after so much had gone on today it was hard to relax. Plus my clit and tessies had been pinned under me for hours at this point and they ached. Ms pulled into our parking garage and shut off the car. That's when panic set in again.

"Listen to me muffin," Ms said without my saying a word, "we barely know our neighbors and have been here for 3 years. For all they know we could be a family of 8 living in there and they'd have no clue! Just relax and act like everything's normal and no one will say a word okay?"

"Yes Ms." I replied quietly while trying to femme up my voice.

She got out and waited for me at the trunk while she picked up the bags. When I got there she handed me a bunch of them and closed the trunk. We had to walk down two flights of stairs to get to the cross over from the garage to our building. Then it was a quick elevator ride up 5 floors and a long walk to our apartment. We saw all of 2 people on our walk and none were close enough to even bother speaking to. Ms opened the door and let us inside. It felt so good to be in our home finally!

"Tell you what," Ms said putting the bags she had down, "leave the flip flops on as we don't want to mess up your pretty red toes and be careful taking off your jeans and shirt."

I happily slid out of the jeans knowing that it would give my aching parts a bit of relief and carefully removed the shirt as not to tug on the piercing. I stood there waiting for Ms' next direction in my pale pink thong and panty stuffed bra. She looked at me and giggled.

"Fold your clothes neatly," She said trying to be stern, "and I'll find something for you to wear tonight."

I truly hoped what she would find was in the Victoria's Secret bag. I folded the jeans and shirt carefully and then put them in my closet by the front door. All the while I was unable to take my eyes off the Victoria's Secret bag.

"Did you have something in mind?" Ms asked.

"Well ..." I said softly, "we did buy that nightgown this morning at Victoria's Secret. That would work okay wouldn't it?"

"Do you really want to wear that?" She asked holding it up. "I don't know, I've been thinking about it ever since we left the mall and I just don't know if I'm a fan. I may just return it."

"What?" I replied unable to contain my shock. Instantly I knew this was a mistake.

"Why to you really like it?" She asked raising an eyebrow at me.

"Yes I do Ms," I said admitting my defeat, "I like it a lot and really want to wear it."

"Well there will be a few things you have to do first." Ms Allison said with a big grin reaching into the bag from the adult store. "First take these," She said handing me the numerous dildos, "and wash them off with the anti bacterial soap."

Walking to the kitchen I tried to think what she would have me do with 9 dildos. I had to remind myself that Ms. Allison was still way ahead of me and was now playing me like a well tuned instrument as she had been the past weeks. Removing the dildos from the packaging I washed them one at a time in the sink and let them air dry in the dish rack. As I did Ms walked into the kitchen behind me and took the first dildo from the rack. She walked to the refrigerator and stuck the 7" dildo to the door just about the level of my crotch. She then took 3 others and walked into the living room, out of sight, and returned a minute later without any of them. She took the remaining three 7" dildos and disappeared again coming back into the kitchen empty handed again.

"You're going to have to earn that nightgown muffin," Ms said walking up to me and releasing my tessies and clit from the gaffe, "and to start we're going to work on your oral skills. I've placed the cocks you bought in the rooms of the house, whenever you enter one of the rooms you will suck that cock for ten deep strokes with your mouth." Ms said this while teasing my clit and tessies through the thong I had on. "Why don't you start with this one," Ms said tilting her head toward the refrigerator door, "and be careful when you kneel that you don't mess up your toes."

"Yes Ms." I said softly suppressing a moan.

Walking to the refrigerator I knelt on the stone tile floor and wrapped my lips around the 7" shaft. I took the dildo as deep as I could in my mouth and relaxed my throat.

"Go deeper with each stroke muffin." Ms instructed. "By number ten you should be touching the fridge with your nose." I managed to barely touch the refrigerator door with my nose on number ten which pleased Ms. "Now go find the others." Ms ordered.

The next dildo was in the living room and I had to stand on my toes to take it into my mouth. I walked down the hallway and found the next one there. It was halfway between standing and kneeling position and I had to squat a bit to take it into my mouth. With each dildo I found it easier to take them to the point my nose fully pressed against the wall. The next dildo was in my bathroom on the full length mirror behind the door which was also at kneeling height. With that dildo I had to watch myself as my mouth approached the dildo, thankfully the make up and wig made me look more femme like and I could feel my clitty harden. I wasn't just a guy in some lingerie sucking dildos, I was that girl in that magazine getting a hard cock fed to her. My clitty got so hard it ached and I was thankful my cage wasn't on. There was another in my bedroom by the closet which I had to stand on my toes to get to as well. As I sucked this one Ms reached around and stroked my clitty lightly with just her fingertips.

"Oh my you are a horny little sissy slut aren't you?" She asked cupping my bare ass with her other hand.

I walked to Ms Allison's room and found the next one on her sliding closet door which was also a full length mirror. Once again I looked at my make up and wig in the mirror as my mouth approached the dildo.

"Are you enjoying your cock tonight muffin?" Ms asked pressing her body against the back of my head. I couldn't answer as my mouth and throat were full of latex dildo. "You look like a hot slut sucking that cock." Ms said sensually. "I'll bet you feel like one too which is why that clitty of yours is so hard right now." I groaned in agreement as Ms squatted closely behind me. "You'd probably cum right now with two or three strokes wouldn't you?" Ms asked as she teased my clitty again.

I groaned deeper and pressed my nose hard against the mirror feeling the latex balls against my chin. My head was spinning not just from not being able to breathe but from the thoughts running though my head as well. As I pulled back I could see Ms Allison in the mirror, her look was ravenous as well, she was getting excited watching me do this which spurred me on!

"One more to find sweetie." Ms whispered in my ear squeezing my clit as well.

I backed off the dildo and walked to Ms' bathroom where the final one was again at squatting height. It took some work to find a comfortable position which ended up being with my legs spread and my back arched sticking my ass out. While I was on stroke eight Ms gave my bare ass a hard swat with her hand. I quickly backed off and stood up.

"Oh no!" Ms exclaimed. "No cheating," she said waving a finger at me disapprovingly, "get back down there and start at one again."

This time on stroke three she spanked me even harder. I grunted and kept sucking trying not to miss a beat with my stroke. Halfway through stroke five my other cheek got a swat but I kept going. Ms spanked me three more times but I was able to get each stroke deeper just as she had originally instructed.

"Okay muffin back to the living room." Ms ordered leading me out of the bathroom. I went to follow her out to the hallway but she stopped me. "Forgetting something?" She asked. "You did just walk into the bedroom didn't you?"

"Yes Ms." I replied not following what she was saying.

"Each and every time you enter a room you'll give the cock in that room ten strokes!" She said firmly.

I took a couple steps back and knelt in front of her closet door sucking the dildo ten times. Joining her in the hallway I stopped and squatted at that dildo and sucked it as well before joining her in the living room and sucking that dildo. For the next hour Ms had me put the shopping items away one item at a time. Sometimes she would send me on off trips to her bathroom or to the kitchen while other times she would combine the trips to see how many combinations of dildos she could have me suck. By the end of the hour my clitty had been hard so long that my tessies ached too! Finally Ms let me kneel by her feet and relax for a minute.

"Want to see what's in the box?" Ms asked eyeing the sealed box she had gotten from the adult toy store.

"Yes Ms I do." I answered while trying to remember to keep my toenails off the floor.

Ms Allison slowly opened the box and removed a couple DVDs handing them to me. Both of them featured sissies on the cover in very provocative positions. She opened the first one and handed it to me.

"Go put it in the DVD player muffin." Ms said handing it to me.

I put the DVD into the player and set up the TV. When I turned around Ms Allison was standing and holding up a leather harness. She got it straightened out and I could immediately tell it was a strapon harness. This was a different harness because it had two shafts located inside the harness. Both of them were positioned to penetrate Ms Allison.

"We won't be needing these." Ms said removing the two shafts. "Help me put this on."

Helping Ms Allison put a strapon harness on was almost like loading the gun being used for my own execution. She had me adjust the waist and then the back so it fit comfortably.

"Hand me that 8" cock." Ms said pointing to one of the two remaining realistic dildos.

Ms held the TV remote in one hand and her dildo in the other and sat to watch the movie. She seemed to not think about it but I couldn't notice how her fingers seemed to constantly touch the flesh colored phallus sticking practically straight up in the air. We were quite a contrast, I sat with my legs crossed and Ms sat with one foot on the coffee table and her legs spread. She was obviously sitting as a guy would. Plus she was still fully dressed and I was sitting in just my lingerie.

"Okay now watch closely." Ms said turning to make sure I was looking at the screen. "You can learn a lot from this girl."

As I turned to look at the screen I saw a red haired sissy on her knees between a well hung man's legs. His erection was massive. The sissy licked him from underneath his balls straight up the shaft before taking the head into her mouth. It was amazingly hot watching her bob up and down on the shaft only stopping to lick the underside or suck his shaved and very swollen balls.

"Stop drooling amber." Ms said reaching over and touching my aching crotch area. "You already have a wet spot on your thong from all that precum you're leaking." I didn't need to look down, I knew it was true. "Now on your knees," Ms said turning and hitting rewind on the player, "I want you to mimic your on screen friend there."

Ms spread her legs so I could crawl between them. She slipped her right foot between my thighs and used the instep to rub my tessies and clitty while I mimicked the actions of the redhead. What I found was that my long blond hair got in the way and I had to keep sweeping it around my neck or behind my ear. Ms would pause the DVD from time to time to make sure I was perfecting each movement. I felt amazingly slutty as I did this and relished in the enjoyment that I was seeing in the sissy I was watching. When I saw the man who's cock she as sucking grab the back of her head and a handful of hair and watched him ram her head down onto his cock over and over I trembled all over. He was using her mouth like a pussy and was fucking it just as hard. When Ms slipped a hand around the back of my head I quaked with anticipation and fear.

"What do you think?" Ms asked looking down at me while still massaging my crotch with her foot.

"It looks scary Ms." I said meekly.

"Don't worry muffin," Ms said with a wry smile, "I'll be gentle."

Ms slowly started to move my head up and down making sure to bury the dildo as deep into my head as she could. She slowly picked up the pace and intensity. I felt incredibly slutty and sexy and wanted to beg for more. No, I wanted to scream for more and savor this feeling forever. Then Ms took it even further!

"Like that slut!" Ms hissed, her voice dripping with disdain. "Suck it whore!" Her words, her voice, her hands controlling my head and ramming it into her massive phallus, I could feel my clitty ache and ooze precum. "Ohhhhhhh someone likes that doesn't she?" Ms growled deepening her voice. "Someone likes being called a whore," Ms continued, "and being treated like a whore too don't you?" I groaned yes around the massive shaft. "I'll bet if I wanted," Ms said slowing her hands down for a moment, "I could bend you over this couch and fuck your pussy with this shaft couldn't I?" I couldn't answer, all I could do was tremble. "Just what I thought," Ms Allison laughed, "my little whore really wants to be used like one!" Ms Allison pushed me back and stood up. While she's not tall she seemed to tower over me. "Get up slut!" She commanded. I immediately stood and waited her next command. "Knees on the couch, elbows on the back and keep looking straight ahead!" Her voice was stern and authoritative.

Ms pulled my thong off my hips and over my butt letting it sit at the top of my thighs. I felt vulnerable and very, very slutty. My emotions and senses were on overdrive. I even felt as if I could feel every single strand of hair touching my face. While I had never considered being in this position the feeling was amazingly intoxicating. Ms seemed to take forever and when her fingers finally touched my backside I practically jumped.

"Just relax." Ms said in stark contrast to how she had spoken moments ago. "Take nice controlled deep breaths," Ms continued as I felt several slick fingers rubbing around my pussy opening, "it will be easier if you just stay relaxed."

"Yes Ms." I replied breathlessly.

When I felt something press against my pussy opening I immediately tensed. It was a natural bodily reaction but I chastised myself for doing it. Ms seemed unphased and continued to talk softly to me reminding me over and over to relax and breathe. On the third attempt the latex phallus Ms had in her hand started to penetrate me. I couldn't help but moan.

"You're doing fine muffin," Ms said in a soft and smooth voice, "this one is just a bit bigger than the one you're used to but you'll get used to it soon enough."

Ms Allison wasn't kidding when she said it was bigger. She used the plug like a dildo inserting just a little more with each slow push. Eventually the largest part of the plug slipped inside my pussy which then clamped down around it. Ms then pulled my thong back up making sure to tug it into place. The thong was now even tighter around my swollen tessies and aching clitty.

"I think you've had enough for one night." Ms said letting her fingers gently glide over my burning flesh. "Take your bra off and fold the panties in the cups," Ms said stepping back so she could watch, "and I'll help you get ready for bed."

A moment later I stood before her wearing just the wig and tiny thong. While I felt a bit silly I was still so aroused it didn't matter. Ms picked up the pale yellow nightgown I had fallen in love with and held it up in front of me.

"While I'm sure you'd like to put this on right now," Ms said cupping my clitty and tessies, "these will make it difficult and will ruin the look. Don't you agree?"

"Yes Ms." I said unsure of what she was up to.

"I know of a quick way to fix it," Ms said stepping a bit closer to me, "but you may not like it."

Just then I felt Ms Allison's hand lift off my crotch. She must have flicked her wrist because a second later her four fingers gave my tessies a not so gentle swat. It wasn't hard enough to double me over or even make my eyes water but instantly what had been a raging hard clitty began to shrink.

"Sorry sweetie," Ms said turning and reaching for the CB, "but if I told you I was going to flick your tessies like that you would have complained." Ms was of course right as usual. "Now pull down your thong so I can lock you away again." Ms put the CB in place and locked it with the small brass lock. "Now pull back up your thong and put on your nightgown."

The nightgown was everything I expected it to be. It was light, soft and oh so delicate feeling. My clit tried to swell again but was stopped quickly by the cage. Ms ran her hands over the soft material driving me crazy. The feeling of the soft material over my shaved body was amazing. Ms handed me the robe which I put on as well. I couldn't wait to see myself in the mirror!

"Okay muffin," Ms said releasing me, "why don't you head off to bed. Make sure to kiss all your new toys good night like a good little slut, take care of your wig and leave your heels by your bedside."

"Yes Ms Allison." I replied dutifully.

I made my way past to the dildos along the way and did my best to take them as deep as I could into my mouth. In the bathroom I was able to see my reflection. The robe was really more for show and when I walked the generous slit in the leg showed through the robe too. With heels it would show even more! I couldn't wait until morning. Thirty minutes after Ms had sent me off to bed the wig was on a Styrofoam head on my dresser, my heels were next to my bed so I could slip them on before I got up and all the dildos had touched the back of my throat. I couldn't imagine what kind of dreams I'd have after the night I just experienced but I couldn't wait!

Ms_Allison
Ms_Allison
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26 Comments
AnonymousAnonymous27 days ago

You surely know how to work a sissy Ms Alison, both mentally and physically. Makes me wish it was me 🎉

friskyboifriskyboiabout 1 year ago

Oh so hot, loving these stories,only thing that would make them better for me if there was some foot worship

AnonymousAnonymousabout 1 year ago

Completely terrible.

danieelledanieelleover 1 year ago

This gets better and better! Thank you!

AnonymousAnonymousabout 2 years ago

I love crossdressing but the rest about the sucking is just a fantasy for me and I never intend to actually do that but I love the clothes.

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