Sissy Maid to Be... Ch. 02

I would recommend reading Chapter 1 to get to up to speed on the story, but if you want to start in the middle...

Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife.

Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves.

Jeremy is getting ready to transform into sissy jenny for her and her wife's night of sissy maid play and fun. Lizzy has a night planned but refuses to tell sissy jenny the plan. Only to instruct her to put on her pink sissy maid dress that is worn for events and competition. Sissy jenny doesn't know of any event but is expecting an evening of public humiliation out of the house. What the actual plan is will be a surprise she never thought would happen...

Chapter 2

Lizzy got off of me and removed the restraints. I rubbed my wrists to get the blood flowing in them again. I sat up and looked down at my locked up clitty. Lizzy was right. It was the smallest it had ever been. I can only imagine the picture she sent Tiffany. Probably her holding her pinky next to it to show how little it actually was. I remembered how Lizzy had said that Tiffany said it looked "smaller than a baby's" and that started the blood flowing again. I could only imagine what she may say then next time she saw me in person and her always thinking that I was hung like a baby in real life.

I got up and Lizzy said, "You should start getting ready, we are going to be on a tight schedule already as it is and playing with your sissy clitty took up too much time already."

I replied, "sure, I will get to it right way."

"Remember the "mistress", I want you in the right frame of mind even if you aren't in your dress yet. I am going to take complete control and you have to be willing," she said.

"Yes mistress," I replied and cast my eyes down in a submissive nature.

"Now get made up and dressed, so the fun can begin," she instructed.

"Yes mistress, but shouldn't you start getting ready as it takes you longer to get ready for our events?" I asked.

"Who said anything about an event? Now get ready and come downstairs," she said.

"Yes mistress," I replied. The wheels turning in my mind with possible scenarios that were likely to come.

I went into the bathroom and dried my shoulder length brunette hair the rest of the way. I looked in the mirror and saw a long string of precum dangling from the end of my chastity. I took my finger and scooped it up on the fingertip. The string of precum dangling from the end and raised my finger up and lowered the precum into my mouth, something I wouldn't dream of doing if mistress would have allowed for me to cum.

I took a headband with rhinestones, one of my favorite to wear when applying my makeup, and pulled my shoulder length hair away from my face. I applied a generous base foundation on my smooth face, in case it was a longer night out than I had thought. I didn't want a 5 o'clock shadow coming through and clicking the switch in my mind back to male mode. My eyebrows had been waxed two weeks ago on our last sissy outing to the salon so there was no need for a touch up. I applied my eyeshadow in two layers to accentuate my long feminine eyelashes that I had been lucky enough to be born with. I used to hate them when I was younger as I was teased about it incessantly but now they were an asset as both a male and a female as they accentuated my baby blue eyes. A layer of white eyeshadow was applied right under the eyebrows and a dark pink was applied to the eyelids so that they would match my sissy maid uniform. With a hand steady as a surgeons I applied my eyeliner making sure to add a little "v" at the end of the eyes. I applied a light application of mascara to make my "covergirl model" eyelashes look even longer than they already were. Next came the blush on the cheeks; an upstroke brush on each side. A trick I had learned as I got better at doing my makeup to accentuate my high cheek bones. Last I took my lip liner and outlined my lips making them look fuller and lusher. Lizzy still teases me that I like to do my makeup like a tramp and that only girls from the 80's would do their lips that way but I still love how it looks. I filled in the lines with some wet pink lipstick to match the look.

The look in the mirror was perfect. A fully made up face with a trim man's body with a tiny penis, or clitty as mistress liked to call it, locked up in a small pink chastity device. I checked my makeup and made sure that nothing was out of place then removed the rhinestone headband to work on my hair. I was unsure how I should do my hair for this evening's fun so I decided to ask for Lizzy to help out. I called down to Lizzy, "Mistress would you be able to help your sissy with her hair tonight?"

Lizzy came up the stairs and let out a little giggle when she saw me. "You look very pretty sissy, I was hoping you would ask for some help," she said. "Take a seat on the edge of the whirlpool tub and we will get you all pretty for your big night. Lizzy placed a towel on the edge of the tub and instructed me to sit. "We don't want you little sissy tooshie getting cold, I think your little parts have had enough of the cold already," she said laughing.

I took my seat as she instructed and sat there while she pulled out the necessary tools to do my hair. I was turned away from the mirror as Lizzy insisted that I could not see the final product until she was done. I sat on the towel with my legs together with my locked clitty between my legs to give it the illusion that I was smooth between my legs. Lizzy pulled out the hair clips and bunched the hair from the top into a pile and clipped it place by applying a pink crocodile clip so that she could work on the lower section of the hair. I felt her take up the first section of the hair in her hand and twist it in the curling iron. She release the strand of hair from the iron and I felt the hot curl drop against the side of my face. I was thankful that mistress had insisted that I sit on a towel as I felt my clitty quiver and precum drip out. She repeated the process having me turn this way and turn that way, bunching up my hair and fastening it with pink clips until she stood back and viewed her work. She reached into the bathroom closet and produced a can of hairspray and applied it to her work. Taking time after each spray to step back and "fluff" a section of hair here or there until it met her approval.

Lizzy said, "Let's get you up sissy and take a look at my pretty girl."

I stood up hoping that the towel had soaked up my excitement, but felt a strand of precum running from my chastity down my leg almost reaching my left knee. Mistress saw this too and instructed me to stop where I was.

"I have no idea how you are going to make it through the night tonight when you insist on making a mess with everything you do? Stand here and don't you dare move toward that mirror until I come back," she said.

I stood in place with my head down. I could feel the full curls against my face and couldn't help but release another thin line of precum from the tip of my locked chastity and watch as it fell to the bathroom floor. As it touched the ground Lizzy walked into the bathroom and said, "I swear I have never seen so much cum come out of a sissy's clitty as yours has in the last 20 minutes."

I could have told mistress that there was more when I was doing my makeup but then I would have to explain how I had consumed it like a greedy girl in one of the adult movies that we watched together on occasion.

"Well what do you have to say for yourself sissy?" she asked.

I kept my head down and replied, "Sorry mistress, you know how dressing pretty and getting special attention turns me on. I can't help that I get so turned on and drip all over the place."

Lizzy looked at me and said, "Well maybe you are more girl than either of us realized, getting all wet when you get turned on. I thought real men got hard when they were excited, not soft and dripping wet. I have a temporary solution for our problem right now and we will have to find a more permanent one later, but first you have to take care of the mess you made when I was out of the room for LESS THAN 30 seconds. Thankfully that towel soaked up your other mess when I was doing your hair but you will have to clean this mess up. Get on your knees sissy and clean up your sissy milk for mistress."

I dropped to my knees and grabbed the towel that I had been sitting on when mistress was doing my hair and reached to wipe up the precum puddle that had formed when mistress grabbed the towel and asked, "What do you think you are doing sissy?"

I replied, "Cleaning up the mess as you instructed mistress."

"Not with my towels you are not. You already made a mess of this one and it is covered in precum. You are not spreading more all over my bathroom floor. Bend down and use your tongue to clean up your mess. You know it is what you want to do anyway," she said.

I bent over and put my face close to the puddle of precum I had made on the floor and stuck out my tongue. I was grateful that the cleaning lady had come the day before so I knew the floor was clean but I was more worried that I would mess up my makeup or get cum in my hair, so I touched it with the tip of my tongue first. I tasted the salty thin puddle of "sissy milk" on the floor. I retracted my tongue with the precum back into my mouth and savored the taste. Normally the thought of eating cum turns me on until it comes to the actual task after I am allowed release, but when I haven't t had any release eating cum comes naturally as it feels like it puts me in my place as the sissy. I bent my face back down and felt my hair fall around my face as I lapped up the mess I had made on the floor. I heard another "click" from Lizzy's camera phone and the telltale "swoosh" as another text message went out.

Lizzy laughed and said, "Tiffany is loving your transformation. She said you look like a little puppy eating off of the floor. She still can't believe that you are licking cum up off the floor so readily. I told her I told you to grab a towel but you begged me to let you do it with your tongue!"

I couldn't believe what I heard and I wasn't sure if what Lizzy was saying was true but I had heard the distinct sound of the "swoosh" of a text being sent and, as if to read my mind, I heard the ping of a received text, followed by Lizzy laughing.

"Tiffany used her photo editor and put poodle ears on your head and a tail coming out of your ass," Lizzy said laughing uncontrollably. Lizzy turned her phone to me to show me what had her laughing so hard and I saw it. There I was my tongue hanging out with precum dangling off the end. My done up hair had two white "poof balls" edited onto my head and a white tail with a "poof ball" at the end. To top it off at the top of the screen I saw the name "Tiffany" so I knew the message was real. "I think we might have a new idea for a future outing but we will have to save that for another day as tonight is all laid out." My face burned red with shame knowing that my uncontrollable need to submit and horniness had turned me into a cum loving pet. To top it all off a picture of my shame modified to make me look like a common house pet was out there now and I am sure a topic of conversation the next time we got together.

I finished cleaning the floor of all precum with my tongue, greedily lapping up the last spots and looked up at Mistress with me still on all fours. My cock hardening in my chastity over my ordeal and the humiliation of another person seeing me, not as a person but, as a pet; causing my locked clitty to stick out between my legs behind me.

Lizzy said, "On your feet sissy; time to take care of your leaking problem." And with that she produced my pink ruffled satin panties. They were a custom order as part of the maid uniform. Two layers of satin to encase the sissy's clitty with rows of white lace surrounding them and a little pink bow on the front to top it all off. Lizzy said, "I have made a little modification so I know where you are at all times tonight and have sewn some jingle bells into the ruffles. I think I went a little overboard with the bells but I was too excited." There sewn into the panties were twenty little bells that all jingled at the slightest movement. "Now step into the panties sissy girl so you can finish getting ready for your big night."

I lifted my legs and Lizzy slid them up my freshly shaved legs and I started to drip again. Lizzy said, "Two layers of satin may not be enough." And with that she dug under the counter and produced a large panty liner. "This should help with all that sissy milk dripping out," she said, "we don't want it looking like you piddled your panties tonight." She removed the adhesive cover from the panty liner and affixed it into the crotch of the satin panties and pulled them up the rest of the way, encasing my locked up clitty in layers of satin and lace that jingled with every breath I took.

I stood there and Lizzy finally said, "Now you may take a look at how pretty of a girl you have become."

I said, "Thank you Mistress" and turned and looked at myself in the full length mirror. Starting back at me as the image of a developing girl. I looked from the bottom up. My smooth legs leading to thick ruffled panties covered with little silver bells. My hairless stomach leading to a flat chest that could have been a teenage girls developing hoping that one day she had large breasts. My face made up like a china dolls, all topped off with hair curled and teased to look like a runway model. I felt my clitty stiffen and was thankful that Mistress had put the panty liner in.

Lizzy walked up behind me and gave my nipples a tweak. "I can tell you love how you look and are all worked up with the fun we had before this. I am going to go downstairs to finish up work. Come down when you are dressed and we will get things moving for tonight."

I replied, "Yes Mistress" and curtseyed like I would if I had my dress on. Pinching my fingers like I was holding the hem of my skirt and bowing with my head down and my knee slightly bent. This caused Lizzy to giggle and say "now don't be playing with yourself or starting at yourself in the mirror too long, you have lots of work to do." And with that she left the room.

I knew it wouldn't take me much longer to get fully dressed but it took some time to tear my eyes away from the mirror and get back onto the task that Mistress told me to do. I was snapped out of my trance by Lizzy yelling, "I don't hear those bells jingling. You better get your butt moving sissy." With that I turned from the mirror and got back on the task of getting dressed.

I unzipped the protective cover over my pink formal sissy maid dress. It is a custom made dress from birchplace that Lizzy gave me as a birthday present. The dress is baby pink and zips up into a choker where a lock can be affixed at the back to make sure the dress doesn't come off. The pink is accentuated with white lace all around the sleeves and hems. The dress has a white lace pinafore that locks in the back all of this is accentuated with layers of petticoats that cause the skirt to stand out almost like a ballerina tutu. The outfit is topped off with white stay up nylons where the lace top is clearly visible and a pair of pink and white six inch locking heels with a pink bow at the toes. This outfit is typically reserved for going out to special events as it shows a clear view of my pantied bottom and stocking tops, a view that most dominants prefer while serving them at fetish events.

I was positive that Lizzy had found an event that I was not aware of and I was excited about standing on stage and being judged with other sissies based on my appearance and my knowledge as serving as a submissive maid. I rolled my sheer white stockings and slid my foot in savoring the feeling of the nylon on my shaved legs, sending a slight shiver up my back and inside my panties. Next I pulled out my white lace underwire bra. A respectable size 40C and reached behind my back and fastened the clasp. I reached inside each bra cup and pulled on my chest toward the middle of the bra to add the illusion of a little cleavage. I topped off the full breast look by inserting C-cup breast forms. The bra was thin enough so that the nipples on the breast forms were prominent enough through a thin shirt to look I was a woman whose "high beams" were on and draw eyes from my face to my breasts. I stood in the mirror now seeing a woman in lingerie staring back at me and turned this way and that and heard the bells jingle while I twerked my ass in the mirror.

Satisfied that my underwear was sexy enough for the competition I thought I was preparing for I slid into my dress. I stepped into the dress and slid the satin fabric over my smooth body as I did not want to ruin my hair or makeup. I felt the coolness against my hairless body and a tingle in my panties. I slid my arm into the puffy quarter sleeves and reached behind my back to zip up the dress. I pulled the zipper to the top and felt the choker collar snug. I pulled down on the dress to align the waist with my waist and twirled in the mirror, causing the bells on my panties to jingle very loudly. I heard Lizzy call from the office.

"Is my little sissy playing with herself after Mistress warned her not to?" Lizzy called out.

I stopped twirling and replied, "No mistress, sorry mistress" I was just twirling in my dress.

Lizzy laughed, "You better stop looking at yourself in that mirror and finish dressing that pantied ass."

"Yes mistress", I replied and set back to finishing my attire. Having secured my dress I stepped into my petticoats. They were so full that I had to lay them on the ground to find the opening. I slowly pulled them up enjoying the feeling take me over as I transformed from woman to mincing sissy. I hiked the petticoats up to a level so they showed just below the hem of my dress. I smoothed out the dress so that they lay perfectly over the petticoat again and went to twirl, but stopped myself remembering Mistress's warning just a few minutes ago. I slid the pinafore over my head and secured the four straps so that it pulled in to accentuate my waist and lay over the skirt at the 45 degree angle that the petticoats held it at. I sat down on the bed and opened up my shoe box and found my locking 6-inch heels. The heels were patent white leather accentuated with a pink leather strap running around the heel and a pink bow at the open toe. Mistress had ordered them with a locking strap so that once they were locked on there was no getting them off without the key. I always wait until last to put them on as I knew my feet would be sore before the night was over. I slipped each foot into the heel and locked them on. I stood up admiring my nylon clad legs in the towering heels. I walked to the vanity mirror, wiped the small traces of precum I missed when licking it off the floor and touched up my makeup.

I opened the last box that was part of my sissy maid uniform and removed the little pink satin hat. I placed it on my curled hair and affixed it with bobby pins. I did one last look in the mirror, turned sideways and flipped the back of my dress to expose my pantied ass and walked out the bedroom door.

I walked to the office where mistress was finishing up on the phone and stood silently until she acknowledged me. Lizzy hung up the phone and looked at me smiling. "You make sure the darling sissy maid, jenny." I loved how she addresses me as a girl when I am dressed as one and she knows it so keeps in the spirit of things.

"Thank you mistress," I said as I curtseyed.

"Well kneel down so we can lock on your dress," she said.