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I spent the evening in my bedroom watching porn on my computer. Normally I never watched porn at home or on my smartphone because mom was always barging in without knocking and checking my phone but since she decided to go shopping and I had just been fucked in my ass, I decided to risk it.
I immediately started with gay crossdressers and quickly moved on towards diaper porn and found a huge selection of porn and stories about beta males in diapers getting fucked by powerful men.
I thought about Mr Maddox, I mean Jim, and myself and realized we fit the whole alpha/beta image. He was big, strong and mature while I was small, skinny submissive, wore diapers and fit in his late wife's' dresses.
The strange thing is I wasn't turned off by the idea, far from it, I was excited. I knew I was gonna wear another dress tomorrow and do housework which would almost certainly lead to more sex.
As I thought about it more and more, I reached my hand down to the front of my diaper and started rubbing myself. The diapers mom buys for me weren't as thick as the ones Jim next door had me wear but even so, I began to see diapers in a whole new light. Less like some sort of medical necessity and more like how a pretty girls sees her panties.
As I simultaneously scrolled through the porn on my computer and rubbed myself through my diaper I noticed that there was a term for boys who wear both a diaper and a dress while performing house work for a man.
A sissy maid.
And I saw about a dozen videos of submissive sissy maids getting plowed in their asses by their powerful masters and as I watched I got even more excited.
I was careful not to squirt in my diaper so mom wouldn't see it and instead pulled my diaper down just a teensy bit and filled my hand with the cum. I don't know what made me try it but I gingerly touched my tongue to the puddle of cum in my hand just to see what it tasted like.
Warm and salty and gooey.
I slowly licked my hand clean and went back to my computer and watched more porn till I heard the front door and quickly shut my computer down and got under the covers on my bed. It was still a bit early for bed but it had genuinely been a long day and so I went to sleep.
At some point I heard my bedroom door open like I did many times when mom decided to check in on me but quickly fell asleep again.
And I dreamt of working as a sissy maid.
The next morning, I was wet again. That sucked as it meant I would still need diapers for a while longer but somehow the knowledge that I would still need diapers wasn't so bad knowing someone liked seeing me in them.
I did however have to endure another diaper change from mom. When I was dry it was no big deal but if I was wet mom insisted on changing my diaper herself.
"There now, all changed and ready for work. You go ahead and eat breakfast while I get a few things ready." mom said. At least she didn't call me Missy again. I did take note of the fact that the diaper mom had put on me was the same as the diapers I had worn the previous day for Jim. Ultra thick.
I ate breakfast and then headed up to my room to get dressed. I was truly excited about going back to Jim's house for another day of work. What I saw laid out on my bed was a bit of a shock to say the least.
A complete ladies maid outfit was laid out on my bed. A black frilly maids dress with pink trim, a frilly pink underskirt which was very full, some sort of panty made out of plastic with rows of pink lace all across the back, white girly socks with pink ruffles, black girly flats with a pink bow on top, a pink bonnet and what I assumed was a training bra, also in pink. There was also a whole package of the diapers that Jim next door had me wear yesterday.
And there was a purse but I didn't look inside.
"Mom, what the...?" I yelled.
"Just a few things I picked up last night sweetie. Now get dressed and get ready for work. If your gonna be a maid might as well dress like one. Besides, Jim and I had a good talk yesterday evening and I think he will be impressed." mom explained.
"Mom, I can't wear all this. And even if I could, I wouldn't put it on till I got over there." I exclaimed.
"Nonsense, First I need to tell you a few things. One, I get a notice on every website you visit so I know what you like and two, as I said, I had a long talk with Jim next door and I know what he likes and what he wants. And three, your not really thinking of denying me the chance to see you all dressed up are you Missy? I didn't think so, now if you're a good girl, I will have more things for you when you get home now get dressed, you don't wanna be late." mom said.
I was stuck for it. Mom had seen the websites I had visited all evening yesterday and even talked to Jim.
I put on the horrid plastic panty which had snaps on the sides and was quickly greeted by a crinkling sound at least five times louder than my diapers normally made. Next came the training bra which immediately gave me a tent in my diaper which despite my smaller than normal dick and the thickness of the diaper was still quite noticeable.
There was a slip and after that came the underskirt which flared out horribly. I mean it could have been fun but not if I had to show off to my mom. Then came the dress which fit quite nicely. Shoes and socks came next but I had no idea whatsoever on how to put the bonnet on and I could not zip up the dress myself.
The dress itself came down to about mid thigh and would easily expose my diaper if I bent slightly or twirled a little.
Reluctantly I yelled, "Mom, I need help." and she came quite quickly having anticipated my needs.
"I can't zip up and I have no idea how to put this on. And where did you get all this anyway?" I asked as curiosity trumped my embarrassment momentarily.
"Jim, you new boss and boyfriend told me about this wonderful store in Newhaven thats open till eleven. Now as for the dress, it's not just a zipper, it also has buttons to hide the zipper so you will always need a little help getting it on and off. The bonnet just ties losely under your chin baby." mom said as she fastened up my dress and did my bonnet then she added, "Oh you look so precious. I have to have a picture."
And so I endured several pictures of me in my new maids dress.
"Off to work now baby." mom said swatting me quite hard on my diapered and pantied ass but with all the padding I barely felt it. I headed to the back door figuring I would just cut across the yard and into Jim's backyard.
"Front door Missy." He expects you to use the front door." mom said suggestively. She then said, "And don't forget your purse. I already put your wallet and phone in there as well as a few other things, Plus two extra diapers.
So, dressed like the biggest little sissy on earth I walked outside and towards my neighbors house to work as his maid. Fortunately no one saw me and yet I was curious what would happen if someone did see me.
I was ultra self conscious as I rang the doorbell despite the fact that he was the one who had me wear a dress the day before and had fucked me.
The look in his eyes when he answered said volumes and I actually saw his pants tent right before me.
"Wow, your mom said she was buying you something special but wow." He said with a look of awe.
"I'm here to be your maid as we agreed." I said suddenly terrified that he had forgotten and instead had outdoor work for me to do. "Where should I start?"
"Laundry has been piling up forever I'm afraid plus I haven't vacuumed in a long time. But could you maybe help with this first?" he said pointing at the tent in his pants. He then almost tenderly guided me to my knees and unzipped his fly to expose his cock.
I had never sucked a cock before but I knew the basics like I'm sure everyone did so I opened wide and took his cock in my mouth and with some effort to keep my lips over my teeth, I gave my first blojob.
Sucking cock was very different than getting fuck in my ass, for one thing, it was far more work. Getting fucked didn't require any effort, I just had to lay there and take it but sucking cock was different.
The rewards were different as well, when Jim fucked me I shot a load of cum into the nightshirt I had been wearing but sucking cock left me a mouthful of warm sticky and salty cum which was a huge turn on for me.
After my very first blojob, I spent the morning doing laundry and vacuuming the upstairs of Jim's house but what I really wanted was to get fucked again. There was something about wearing a maids dress along with a thick diaper and ultra noisy plastic panties that just made me want to bend over and take it up my ass. I was so damn horny. To make matters worse, I got to see all the sex toys that were in Jim's bedroom when I vacuumed or put away laundry.
So I hatched a plan.
It felt a bit strange to deliberately wet my diaper as I had spent my entire life practicing to do just the opposite but I managed to let loose a stream of pee pee and completely drench my diaper.
I grabbed the purse mom had sent with me and the extra diapers took up nearly the whole purse. I grabbed one and went to see Jim in the living room.
"I need help." I said, "I had an accident but I can't change my diaper by myself while wearing this dress and I can't take the dress off by myself. Can you change my diaper please?"
Jim took the fresh diaper from my hand and led me upstairs to his bedroom and had me lay on my back on his bed. "What's say we play a little game while I change your diaper huh Missy? Would you like that?" He asked.
"Sure, like yesterday?" I asked excitedly.
"Something new perhaps." he said and went to a drawer and removed another ball gag but this one was different. It looked like a giant cock. He placed the rubber cock in my mouth and secured it with a pink ribbon behind my head and I took to it right away and began sucking on it. He then pulled out some bondage cuffs from under the bed and placed my arms in them and pulled them tight out to the edge of the bed.
He then place some sort of leather cuffs on my knees and attached a steel bar to them forcing my legs to stay open wide and attached a chain to the bar and the headboard forcing my legs to stay open and up for his attention.
All the videos I had watched the night before of sissy maids getting used and abused by their masters came flooding back to me and I eagerly awaited the fate I had planned for myself when I deliberately wet my diaper.
Jim then stripped naked and got on the bed between my forcibly spread legs and removed my plastic panty and diaper. Then he entered me.
It hurt but not like before, less pain because I was expecting it, anticipating it even wanting it. He fucked me for a good half hour before my own cock exploded sending a load of cum into the underskirts of my maids dress. Somehow the thought of working for the rest of the day with a cum stain in the skirts of my dress was exciting.
But what if mom sees' it? I thought to myself as the afterglow of my orgasm was shattered by the pounding my ass was taking.
My thoughts about my mom were sidetracked as Jim's cock exploded inside me completing my violation and the feeling of being inseminated thrilled me.
Jim pulled out and got off the bed. After he cleaned up a bit, he undid the spreader bar and diapered me again and then snapped the plastic panty back on me.
He didn't release me from my bondage and I still had a giant rubber cock in my mouth that I could not spit out. He turned off the lights and whispered, "You've had a hard day sweetheart, get some rest." and left the room closing the door behind him.
As I lay on the bed with my bound arms forcibly stretched out to the edge of the bed and happily slurping on my rubber cock, my thoughts returned to my mom.
Surely she knew that with this maids dress on I would end up getting fucked again so was she okay with it? It seemed so.
Mom seemed so giddy to see me in a maids dress and even took a few pictures of me. Did she want me to be a girl?
Normal parents would have been angered when they found out their son had watched sissy diaper porn on the computer but mom responded by buying me a pretty maids dress with a promise of more if I was a good girl.
Unable to move was a bit uncomfortable and so I shifted my weight a bit and was greeted every time I did with the rustling and crinkling of my diaper and plastic panty.
The answer to mom was simple, she wanted a girl, a daughter in a diaper and pretty dress just like Jim did. She wanted me doing housework dressed as a maid. She even wanted me to take Jim's cock up my ass and probably suck him off too.
Boys are told to get over it but girls are comforted and any time I got teased growing up, mom always comforted me.
My thoughts were interrupted when Jim came back into the bedroom. He took off my plastic panty and diaper and snapped a chastity cage on my dick. "Give this key to your mother when you get home sweetie." He said holding up my purse and dropping the key in it.
He then released me and then loosened the ribbon so I could take the cock gag out of my mouth while leaving it to hand around my neck for anyone who looked at me to see.
We had lunch, pizza again and beer and he was sure to make sure I had drank four full beers and I was sure he wanted me to wet myself again.
I spent the rest of the afternoon finishing up the laundry when the urge to pee hit me again and instead of fighting it like I had practiced for a lifetime, I just let it happen hoping it would lead to more cock up my ass.
When I told Jim I had another accident, he said, "Why dont you knock off for the day. You've done so much already sweetie. Go home and have your mom change your diaper." then he put a hand around me grabbing me by the small of my back and pulled me into him and he passionately kissed me.
And I kissed him back.
After the wonderful kiss, he grabbed the cock gag hanging around my neck and gently placed it back in my mouth and pulled the ribbon tight to keep me gagged. He then whispered in my ear, "How about tomorrow we forget about housework for a day and go for a drive? Would you like that?"
Terrified at the prospect of being seen dressed as a sissy but excited by the same thought, I just nodded my head yes.
He placed another two hundred dollars in my purse, handed it to me along with the last diaper I had and ushered me out his front door. I walked next door to my house and the only difference between now and when I came over this morning was an ass full of cum and a rubber cock in my mouth not to mention the chastity cage in my wet diaper.
Not able to talk with my mouth gagged with a huge dong, at least not coherently, I just handed the diaper to my mom. I was still holding onto my purse when mom had me lay on the floor in the living room and proceeded to remove my plastic panty and soggy wet diaper.
"My my, what a pretty little thing your wearing." mom said noting the chastity cage which until then I hadn't known it was pink. I opened my purse and handed mom the key but she left the thing on me and proceeded to diaper me and replace the panty.
She took the cock gag out of my mouth and asked me how my day was.
"So how was your day Missy?" she asked.
"Okay, can I ask you a question?" I countered.
"Go ahead sweetie. What's on your mind?" She said sounding for all the world as if she were talking to a three year old.
I chose my words carefully and asked, "So, do I get to be your daughter now?"
"Sweetie pie, you were always mommies daughter. You just needed a little time to figure it out." Mom answered.
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