The Bargain Dresses Ch. 01

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Tricked into becoming their Sissy Maid.
1.8k words
4.1
37.8k
13

Part 2 of the 2 part series

Updated 06/08/2023
Created 09/09/2017
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Harold's words raised concerns in my mind but as Jean smiled at me those concerns evaporated. I simply basked in her obvious approval and forgot everything else.

Jean looked at the time and told me I should stay tonight so I could start early and see what a full day as their maid would be like. She called Sandy up to show me to my room for the night.

During our earlier chat both she and Sandy had sprinkled in several questions about my life. Thus they knew that I had the next two days off and, as I preferred to keep my transvestism secret, wasn't very close with friends, family or any of my neighbours. If I didn't go home right away I wouldn't be missed soon.

I'd also explained how I'd found myself addicted to an ever increasing image of feminine perfection. Going from simply dressing to having to shave my body smooth, learning how to use make up when I was dressed and growing my hair out long enough to style femininely. Both had looked pleased when that came up.

Sandy gave me a superior smile then motioned for me to follow her downstairs. I was taken to her deceased Aunt's room. Sandy reached under the bed and pulled out a collar attached to a light chain.

"My Aunt was a sleep walker so we found it prudent to make sure she didn't wander too far. The chain is long enough for you to reach the bathroom and even get into the shower but not much further."

She locked the collar around my neck then unlocked the uniform dress and heels before sitting on the edge of the bed and leaning back on her elbows to watch me intently.

"You can't sleep in your uniform so take your clothes off."

I unzipped the dress and stepped out of it, then folded it to place it on the dresser. The crinoline was folded and placed atop it. Stepping out of my heels I began to tremble a bit.

The very rare times I'd met with someone before I'd always felt exhilarated when displaying myself in lingerie'. I was generally sexually aroused and in control. This time I wasn't aroused but felt exposed, vulnerable and helpless. I wanted to cower and cover myself.

"I told you to undress, Missy. Take everything off, EVERYTHING!" Sandy snarled at me.

My body jerked at her words and my hands shook as I fumbled with the garter snaps to undo my nylons. I placed my nylons over the back of the chair by the dresser and still fumbling uncontrollably managed to undo the garter belt to place with them.

I may not have felt the arousal but my body was responding whether I wanted it to or not. The front of my panties had a large wet spot that embarrassed and surprised me, but not Sandy, who shook her head.

I removed my bra and panties hurriedly, both to remove that humiliating wet spot from sight and so I could do my best to hide my nakedness with my arms and hands. Sandy stood up and walked around me slowly, slapping my hands down and telling me to stand up straight. She chuckled at my hard cock, still dripping pre cum, and slapped it several times till it softened. Shaking her head she wiped the pre cum up with a finger and lifted it to my lips. I licked her finger clean without thinking about it.

She continued walking around me, running her fingers and hands down my back, cupping and squeezing a lower cheek, slowly up my thighs. She was playing with me like a cat playing with a mouse.

Every time my cock started to stiffen again she would slap it till it softened. I lost track of how many times she did that or how often she lifted her finger up to be licked clean; of how often she'd swat my hands away when I'd involuntarily try to cover myself.

"That little thing is repulsive and disgusting to me and it just won't stay down. I should slice it off and at least make you a bit more attractive!"

In shock at what she'd said I looked at her face.

"I told you I like girls. If that thing was gone at least you'd look like a real girl, a little girl with that flat chest but at least a girl! Sighhhhhhhhh."

She reached under her skirt and slid her panties off then sat on the edge of the bed and leaned back. Tugging her skirt around her waist she spread her legs and smiled at me. I stared at her slender creamy white thighs and well trimmed pubic hair, her slightly swollen lips with the glistening fluid between them.

I didn't need any encouragement or orders to know what to do apparently. I found myself kneeling, my hands sliding up her thighs, under her to cup and lift her cheeks. My face bent forward, my tongue flicked out along the length of her moist slit. I heard her gasp in pleasure as her lips swelled apart further and shivered in pleasure from knowing she was pleased with my attentions.

Licking, lapping, running the tip of my tongue over her clit as she writhed and gasped her way to orgasm was all I thought about or considered. Her thighs wrapped around my ears, her heels kicked against my back as she writhed and thrust her hips and ass against my face.

As I darted my tongue as deep as possible into her I felt her hands grab the back of my head. Her body arched high and she convulsed, moaning loudly. Gasping for air she fell back on the bed. When she caught her breath she sat up and pulled her skirt back down then laughed as she looked down at me.

"Did you play with that thing or did orally servicing a real woman make you so messy? Either way it just proves what a pathetic little sissy you are."

Still laughing she stood up and left the room. I cleaned myself in the washroom and crawled into bed, my mind whirling with confused thoughts. I'd always tended to be passive but never considered myself to be truly submissive! Yet hearing the first lock click shut had taken away any will I had, leaving me completely servile.

Whatever they asked or told me to do became the most important thing in the world. I basked in their approval of a job well done or felt like crying if they didn't. Why? Why? Would it have been different if they hadn't used the locks?

I'd never once thought about leaving or not doing what they wanted after that first soft click. Would it have been different if they hadn't locked me in the dress and heels? Would I have been able to resist them if they hadn't? Would I have been able to walk out the door? Did they know that it would affect me this way? Why did I need their approval or feel bad if I didn't get it? Was something wrong with me?

I must have fallen asleep at some point as Jean was standing over me to wake me. I clutched the blankets around my neck, feeling so naked, vulnerable and small even tho she was at least four inches smaller then me and at least thirty pounds lighter.

Smiling she undid the chain from the collar, but left the collar locked on me. She got a fairly sheer babydoll nitie top from the dresser and handed it to me. I was told that this was the usual working uniform her sister had worn indoors during the mornings. When I didn't move she put her hands on her hips and looked at me sternly with a tight smile.

"You have five minutes to make yourself presentable, Missy. There are other nities in the top dresser drawer my sister wore for her morning duties if this one doesn't suit you! "

I got out of bed and tried my best to make it upstairs in five minutes but it took at least twenty before I had my face done, my hair brushed and sprayed into place, and slipped into the very sheer babydoll top she'd set out.

Jean sighed and looked at the clock then at me. She guided me through how to make coffee for her and waited until I had placed a cup in front of her before telling me to get myself one and sit down across from her.

"I guess I'll either have to get you your own alarm or get used to you taking this long. My sister just had to wash her face and usually slept in the nitie so she didn't take long at all. Your results seem to be worth the extra effort and time I will say. You were rather a mess when I woke you. Now in a half hour or so you can fry me two eggs with two slices of toast and make the same for yourself. Sandy will be up in two hours and tell you what she wants. Harold will want his breakfast in bed about an hour after that. You take it in on the tray behind you. Keep up with the dishes and do some dusting in between. Now was it today and tomorrow you have off where you work or was it yesterday and today?"

Today and tomorrow I answered. I have to be back at work Tuesday.

"Ok then you can spend the night again and we'll get two full days out of you, unless you decide to quit your job and move in here to be our permanent maid. Now stand up and come around here. There's something we need to do about your appearance."

Nervously I stood and moved to stand in front of her. Jean stared into my eyes as her hands started to stroke my very stiff cock.

"I won't be doing this everyday so maybe you should do it before you come upstairs. Not that I mind really but having this thing standing there like that is distracting and very unladylike."

Her eyes left mine only after she bent forward to start sucking it. Jean was very good at sucking. Maybe not an expert but that hardly mattered at the moment. I put one hand on the table and the other on the back of her chair or I wouldn't have stayed upright as my legs nearly buckled.

It didn't last long though it felt like an eternity until Jean was swallowing my fluids. She smiled up at me and told me she'd wanted to do that for some reason from the first minute I'd come upstairs.

When I'd recovered I started breakfast for us. When I'd finished the dishes Sandy came up and I served her bacon and eggs with toast and coffee. She swatted my erection lightly whenever it rose till it went down then stared at her mother strangely as Jean commented on how she'd forgotten how quickly young boys recovered.

I cleaned up the kitchen and table as soon as Sandy disappeared back to her room. Jean had gone to draw a bath and called me in to bathe her.

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4 Comments
AnonymousAnonymousover 1 year ago

wow - super hot! I hope there are more !

AnonymousAnonymousover 2 years ago

lucky guy.

AnonymousAnonymousover 6 years ago
Isn't this a repeat

?

AnonymousAnonymousover 6 years ago
Good start for a story

Maybe it's me, but I didn't see much original about the story. However, it IS well-written and intriguing, so keep going.

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