Sissy Maid to Be... Ch. 03

Story Info
Sissy Jenny discovers Mistress Lizzy's for her.
3.4k words
4.57
53.6k
34

Part 3 of the 3 part series

Updated 06/09/2023
Created 08/24/2018
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I would recommend reading the first chapters 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 has transformed into Jenny in her pink satin and lace sissy maid outfit 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...

*****

I was done up in my custom-made dress from birchplace that Lizzy gave me as a birthday present. The baby pink maid uniform that zips up into a choker had the pad lock affixed at the back to make sure the dress doesn't come off and keeps me completely under her control. The pink is accentuated with white lace all around the sleeves and hems. I was doing my best to make sure my white lace pinafore and layers of petticoats that that cause the skirt of the uniform to flare out stayed dry while I was doing the dishes as mistress was getting ready. My feet were starting to ache standing at the kitchen sink for so long in my 6 inches heels, but I was unable to do anything to give them a reprieve as they were locked on as well. My lace ruffled panties were encasing my sissy clitty, but I was unable to enjoy the feeling as Lizzy had locked my little thing up in the pink chastity device. I stood at the sink finally completing the dishes and putting them away and moved to clear the dining area table. The bells that Lizzy had sewn in jingling with each movement.

Lizzy called down from the bedroom, "That is exactly what I love hearing. My little sissy jenny doing her chores like a good girl. Make sure you get the tables cleared and when you are done go stand in the corner until I come down for you." Lizzy had designated a spot in the corner of the kitchen by the fridge where I was instructed to stand when not needed when in my sissy maid role. She knew I disliked it as it made me feel like a little kid being punished and I felt, at times, that she forgot that I was standing there with my nose pressed in the corner waiting for her to need me.

I dragged out cleaning the tables as long as I could but eventually, they were shining so that I could see my reflection in them. I obediently walked over to the corner, put my heels together and made sure my knees were touching, flattened the front of my dress and pinafore, and put my nose into the corner. I could hear Lizzy upstairs moving around and was dying to have a seat and give my feet a rest.

I heard Lizzy call down, "Sissy is everything ready and are you in your corner?"

I replied, "Yes mistress, my tasks are complete, and I am standing in my sissy spot."

Lizzy replied, "Good girl, I will be down shortly. Make sure you stay there until I am ready for you." I could still here Lizzy moving around upstairs and after what seemed like an eternity, I heard her walk into the kitchen. I didn't hear the telltale click of heels on the tile floors like I typically do when she is all "dolled" up for an event. She continued to walk around the kitchen then I could hear her walk over to me. She lifted the back of my dress and I could feel the cool air as it swished up. It caused a sensation at exposed part of my legs between the thigh highs and bottom of my panties that sent a chill through my entire body.

Lizzy said, "your butt looks great in those panties. I love seeing the rows of sating and lace. No woman would ever wear something like that, let alone a man. My aunt said she could tell you were "a special boy" at the wedding shower. That's why she bought the maid apron for you."

At this my face burned red. Lizzy's aunt had given her a maid apron at her wedding shower and told her it was for me, but I always thought it was a joke and was not sure she ever did really say that. Hearing Lizzy tell me that her aunt actually did say that and had suspicions put a whole new light on some of the other comments that she made when we were at the lake.

Lizzy tucked the back of my dress into the pinafore and slid her hands onto my waist. She asked, "Didn't you know that Aunt Carol always thought you were a sissy, even before I knew you were a sissy?"

I replied, "I always thought you were joking about the apron and that it was bought for you, Mistress. I did love how you had me put on the panties and put on the apron the next day while I made you breakfast though." The memory stirring my little clitty in my cage.

Lizzy brought her fingers into the top of my panty waistband and slowly slid them down to my knees. I was still facing with my nose into the corner and I felt her slide her hand between my thighs and grab my clitty cage. She pulled my clitty in the pink chastity cage back between my legs and shoved my thighs back together so that my clitty was sticking back between my legs leaving the front of my pubic area smooth like a girls. Lizzy pushed her body up against mine and reached her hand around my waist and slowly slid it down the front of my stomach with her palm flat and her fingers pointing down. She slowly rubbed the front of my crotch where my sissy clitty had previously been. She said, "Aunt Carol loved that picture too. She said she knew she was right about buying the apron for you.

I felt my knees buckle with the words she was saying and the was she was rubbing my smooth crotch. I so wanted to reach behind and release my caged clitty but Lizzy was pushing me into the corner so all I could do was stand there with my face pressed against the wall while she spoke and fondled me.

Lizzy said, "Aunt Carol has a whole collection of pictures of you doing what you love. She has asked quite a few times to have me send you to Atlanta for a week to clean as the sissy maid for her. We should make that happen soon." Lizzy continued to rub my smooth crotch and push me into the wall. "Would my little sissy like that?"

"I would love that very much mistress. A sissy is happiest when she looks pretty and is waiting on others," I replied.

"Good answer sissy" Lizzy said, and she reached down and pulled my panties up. "pull down your skirt and straighten the hems and turn around so I can inspect you."

I released the back of my skirt form the pinafore and straightened my skirt and turned around. I was not prepared to see Mistress dressed how she was. Lizzy was standing there in shorts and a t-shirt. Both were form fitting, but they were things a woman would wear on a day to day basis, not something that you would wear to a fetish event while leading your sissy husband in a maid uniform on a collar and leash.

I looked at Lizzy and said, "Lizzy, aren't you going to get ready?"

Lizzy smacked me across the face and said, "That is the last warning, we had an agreement. You will address me as Mistress for the rest of the evening. No more slip ups, I want you in the right state of mind. Just because your idea of the plan isn't lining out doesn't mean it gives you the right to break the role. Do you understand?"

I lowered my head and replied, "Yes Mistress, sorry Mistress."

Lizzy looked at me and said, "Ok, like I said this isn't probably what you are expecting, and if you do not want to spend all night in the corner in your sissy spot you have better get in line."

I looked at Lizzy and lowered my eyes and curtsied and said, "yes Mistress, what do you require of your sissy maid."

"Good girl" said Lizzy. "Now let's get some things straight. I am hosting guests tonight and I expect my sissy to wait on them like a good sissy maid would. You will be seen and not heard and will only speak when address. Do you understand?"

"Yes Mistress" I replied, "but who..."

"No questions, sissy" Lizzy interrupted, "You will do as you are instructed, or this will not be happening and you and I both know this is something you have always wanted."

Lizzy was right. This is something I had begged for countless times in the past; for her to let me serve as the sissy maid at one of her "Girl's Nights" that she had every so often. Not knowing who was going to see me as the sissy maid was terrifying. The thought of who and how many were coming was running through my head and I was scared that this was a little more than I could handle but I had asked to give up all control and take my true place as a submissive sissy.

Lizzy said, "Guest will be arriving in 30 minutes and I expect things to be ready when they come. Bring up two bottles of wine from the cellar and bring up the hors d'oeuvres from the basement kitchen that I got at the store this morning. When guests arrive, I expect you to meet them at the door and curtsey and take their coats. Do you understand sissy?"

"Yes Mistress" I replied. My heart already racing with anticipation.

"Well what are you waiting for. Get things ready. I want my guests to be impressed," Lizzy said.

"Yes Mistress," I replied and turned to go.

"Hold on sissy," Lizzy said. "One more thing. I have written out what I expect you to say to each of the guests when they arrive" and she handed me a small piece of paper. "I want you to have this memorized perfectly before they arrive so that it looks like this is something you say on regular basis and not something that is scripted."

I unfolded the paper and silently read what she had written on it. Hello sir/madam, thank you for gracing Mistress Lizzy's home with your presence this evening. I am sissy jenny, formerly Mistress Lizzy's husband, but we have both found that I am not a real man and am better suited for serving Mistress Lizzy as her Sissy Maid. Please let me know if there is anything I can do to make your visit more comfortable this evening (and then curtsy and take their coat) If you will follow me I will lead you into the sitting area to start this evening (make sure you walk in front of them and wiggle your ass).

My face was burning with embarrassment just reading the text and let alone she expected me to say this to each guest. The thought of actually doing this in front of people though had me ultra-turned on and my sissy clitty was straining against the chastity cage and I could feel my panty liner getting even wetter than it already was.

I looked at Lizzy and said, "Mistress you want me to say this to each guest?"

Lizzy replied, "Of course sissy. I wouldn't have written it down if I didn't want you to and what did I say about questioning me?"

"Sorry Mistress," I replied, "you say Sir/Madam, are there going to be men here?"

"Tut, tut, tut, again with more questions. You will see when people come in. now go downstairs and get the things instructed and come back up and we will do a practice run before the guests arrive," Lizzy said.

I curtsey to Mistress and turned and walked down the stairs to retrieve the wine and hors d'oeuvres. I grabbed a bottle of white and a bottle of red from the cellar and brought up the tray with the snacks for tonight's event. Mistress was seated at the couch texting on her phone when I had everything arranged and I walked over to her and stood next to her until she addressed me.

"Do you have everything ready sissy?" she asked.

"Yes Mistress", I replied.

"Very good. Let's do a quick inspection then we can do a rundown of your greeting before people start coming over." With that Lizzy stood up and walked around me. "You know the drill sissy lift your dress."

I lifted my dress while Lizzy walked around. She checked my nylons to make sure they were even and that the seems were straight. Checked the locks on my 6-inch heels to make sure they were secure, and I could not get out of them. While my still had my dress pulled up, she instructed me to drop my panties so she could inspect my sissy parts. I dropped my panties and lifted my skirt back up.

"My, my, my," Lizzy said as she was looking at her sissy husband exposed from the waist down and locked into the pink chastity device. "Still dripping your sissy cum and making a mess, and look your pantyliner is soaked with precum. I am guessing you are loving the idea of what is to come and not knowing who is going to actually meet sissy jenny finally." Lizzy grabbed my locked up clitty and inspected. "I can tell you are excited with how swollen your clitty is. I think it was the right choice to deny you release so that you follow through with tonight's plan. I stood there with my wrists limp hold my skirt up high. Lizzy smacked my ass hard with her hand causing me to jump also causing my clitty to shoot a stream of precum. "Good thing your panties caught that sissy, or else people might have seen my pet licking cum off the ground.

My mind flashed to the picture Lizzy texted her friend Tiffany of me earlier in the day licking my puddle of cum off the bathroom floor and the picture that Tiffany texted back to Lizzy where she photo-shopped poodle ears and a tail on me on all fours on the floor with cum dripping off my tongue.

Now stay there while I get you a new pantyliner." I stood in the middle of the room with my skirt held high, my panties around my ankles, and my exposed clitty open for everyone to see.

Lizzy returned with a new panty liner and pulled the precum soaked one out and replaced it with the dry one. She raised my panties back up and patted my ass. "Fix your skirt and get on your knees so we can finish the inspection," Lizzy said.

I straightened my skirt and pinafore smoothed them as flat as my layers of petticoats would allow and knelt on the floor with my head down. The first thing Lizzy did was take my curled hair and from behind me and raise it up. She grasped the padlock and made sure it was secure so that I would not be able to take my dress off. Lizzy let my hair fall back across my dress and fluffed it up.

"I want my sissy to look pretty tonight and I want to make sure that you stay in that dress. Now stand up and let's practice how you are going to greet my guests tonight," Lizzy said.

"Yes mistress," I replied as I stood up and straightened my dress.

"Now sissy, let's pretend the doorbell rings and I am on of the guests. You will run through what I have asked you to memorize so that you are ready when people start showing up. Now move you butt over to the door and lets practice," Lizzy commanded.

"Yes mistress," I stated as I curtsied and walked over to the door.

Lizzy walked outside and rang the doorbell.

Heart in my chest, knowing that the next time the doorbell rang there would be someone else behind the door I opened it. I started to speak, and Lizzy interrupted by screaming, "Oh my God is that you Jeremy! Holy shit! What a faggot!"

I started to stammer, unsure what to say and Lizzy shoved me back, "On your knees" she commanded. "You need to be prepared for that. I expect that will be the reaction that most people will have. Especially the men."

My heart started beating a mile a minute. There were going to be men coming over and seeing me in a pink maid uniform with the skirt sticking out straight with layers of petticoats exposing my ruffled satin and lace panties. They would be getting a full view of them while I walked in front of them with my 6-inch heels locked on and me wiggling my ass causing the bells that Lizzy sewn into my panties to jingle uncontrollably while escorting them to Lizzy.

I stammered, "Mistress, there will be men here?"

Lizzy replied, "What did I tell you about asking questions? Now let's try it again and make sure you get it right this time."

"Yes mistress," I replied and stood up and straightened my dress.

Lizzy walked outside and rang the doorbell again and I opened the door. This time she reacted by saying, "My, my, my, I always knew there was something different about you Jeremy and now I understand why Lizzy looks at other men like she does."

My face flushed red and my clitty stirred in its chastity. I responded by saying, "Hello Madam, thank you for gracing Mistress Lizzy's home with your presence this evening. I am sissy jenny, formerly Mistress Lizzy's husband, but we have both found that I am not a real man and am better suited for serving Mistress Lizzy as her Sissy Maid. Please let me know if there is anything, I can do to make your visit more comfortable this evening." I curtseyed and pretended like I was taking her coat and hung it up. "If you will follow me, I will lead you into the sitting area to start this evening" I indicated that she should follow me and wiggled my ass causing the bells to jingle all the way as I walked her to the sitting room. I could hear her giggling at the wiggling which made me shake my butt even more.

"So, Jeremy, it's jenny now is it?" she asked, still playing the part of the guest.

I turned and said, "sissy jenny, madam. I need to be addressed as sissy in front of my name since I do not deserve to be addressed as a real woman."

"Is that right?" she asked still playing the part.

"Yes, Madam" I replied. "No woman would wear something like this, nor would want to dress like this, and no real man would be caught dead dressed like this. Only a sissy, and that is what I am. I am not a woman and shouldn't pretend to be one and I am as far from being a real man as I can get." After giving my explanation, I curtseyed and stood with my eyes downcast.

Lizzy said, "very good sissy. I am sure you will do great this evening. I am so excited, but probably not as excited as you. Now go get me a glass of wine while I am waiting for my guests."

I turned to go to the kitchen and fulfill her request when the doorbell rang. I froze in my steps. I felt my heart turn on full speed and drop to my stomach.

"Well it looks like people are showing up early, you know what to do sissy. My wine can wait but not the guests at the door," Lizzy said. "Now get your sissy butt in gear."

With that I walked to the door heels clicking on the hardwood floor and the bells on my panties jingling, but I was unable to hear them over the sound of my beating heart. I reached the door and turned the knob and slowly pulled it open...

To be continued...

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16 Comments
1Martiniman1Martiniman27 days ago

This story looks interesting and I want to read it, but it looks abandoned after 5 years. I hate to spend the time reading to only end up frustrated with no conclusion to the story.

missjennymaid…if you are still on Literotica, do you have any plans to finish this story?

4Leather4Leather8 months ago

Loved it so far. Can’t wait for the next chapter.

Just got my sissy maid dress from ( BitchPlaceShop ) it’s forest green the color my Mistress sister loves. This will be the first time Lady Terry will see me in the maids outfit.

AnonymousAnonymousover 1 year ago

What a lovely story, such a pity you haven't written more episodes, I love wearing my pink sissy maid's uniform and serving Master and Mistress and their guests, please write again soon x sissy Lucy

AnonymousAnonymousover 1 year ago

Brilliant, send constant tingles down to my cock.

AnonymousAnonymousover 1 year ago

More more please maybe where he is used by the male guests or gets cuckold and has to provide clean up services or female guests bring other sissies and they are forced to suck each other’s clittie while being filmed.

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