I used to hate diapers, not all diapers just the ones I had to wear growing up. I wore diapers my entire life because of a very weak bladder, In fact I had never really grown out of them like most normal boys.
And boy did I get teased for it.
All through school mom insisted that I participate in phys ed like all the other kids so my diapers were always on display. At least mom allowed me to wear pullups on days when I had to go to the gym instead of my normal diapers that crinkled when I walked.
Now, at the beginning of summer after my last year of highschool I was finally about to get rid of them for good. I hadn't had a nighttime accident in three months and it had been nearly a full year since I had a day time accident. And besides, I was eighteen now so as soon as I manage to get a job and move out of my moms house, I'll be free of diapers.
Or so I thought.
The job part was a bit of a sticking point. I just couldn't seem to find anything. Most employers took one look at my slender frame and quickly moved on to someone else.
Mom was understanding though. Unlike most moms she was fine with me staying home, I think she was afraid of losing her only baby.
Still, I wanted my independence so I kept looking.
I was sitting at my computer in my bedroom scrolling through help wanted ads, this time on craigslist, when I came to an ad posted for some yard work and the location tag was damn near on top of my house.
Outdoor worked really sucked. Not because I hated the outdoors but because this was Florida and the heat and humidity made my diaper so damn uncomfortable.
Anyway I sent a reply and was a bit surprised when I got a response in less than ten minutes.
The response was a no nonsense list of yard work and what each one paid. Mowing the lawn, trimming bushes, straightening up paving stones, edge trimming and stuff like that. And the pay was a bit better that I had exped for such things.
I sent my contact info asking for the job and noted that I lived really close.
In fact, when he finally agreed to let me try some yard work on a piecemeal basis, I discovered it was the man who lived next door. Mr Maddox.
I had barely finished typing my response and agreeing to be there bright and early the next day when mom came bursting into my room without knocking embarrassing me for the hundred millionth time as I was just wearing a diaper and nothing else since I was in my bedroom.
"JIm, the widower from next door just called to confirm that you'll be working for him starting tomorrow and maybe for the entire summer." mom said excitedly.
"Mom, knock first." I yelled covering my diaper with a towel and then added, "I don't think he has enough work for the entire summer.
"I'm not knocking on any doors in my own house. Besides I've changed your diaper many times so quit complaining. Besides I always said you look cute in them." Mom said.
OMG, parents are the worst. I know she meant well, but...
"I just finished talking to him and he wants me there at seven thirty tomorrow morning." I said.
"My baby's getting his first job." mom said as she hugged me embarrassing me further. Uggh.
The next morning I got up early, showered and got ready to head nextdoor for a days worth of outdoor work. And my mom, being a mom, had my clothes laid out on my bed. Unfortunately this included one of my very thick nighttime diapers. I knew why she did this, I was gonna be out all day and she just wanted to be sure.
I was old enough to know better than to argue so I just put it on. Pullups would have been better for working outside but to argue would have been ultra embarrassing.
I chose a pair of jeans that were just baggy enough to hide the bulge of my diaper and all my shirts were long enough to tuck in to avoid any chance of my diaper being seen sticking out the top of my pants.
I've had years practicing all the tricks to hide my diapers. Although it didn't help all those times growing up when mom would ask me in public if my diaper was wet.
And so I headed next door.
I had known Mr Maddox all my life and he knew I was diapered all the time and never said anything. The morning work was pretty straight forward. I cleared accumulated yard waste from the backyard to get it ready for some landscaping.
And wouldn't you know, Florida being Florida, it started to rain... Hard. I was thoroughly drenched by the time I made it into my neighbors' house. And the rain running down my body added to the sweat in my diaper to make it swell up.
"Well that ruined a days work." Mr Maddox said as I came through the back door. and then added, "Let's get you out of those drenched clothes."
"Um, that's all right. I should probably go home and change there seeing as I probably won't get much done in the yard today." I said.
"Nonsense, I promised a full days pay and I have plenty of inside work for you if you want it. I'm afraid I had let a few things fall behind since my wife passed. Come on, lets find you something dry to wear and you can wear one of my wife's diapers seeing as the one your wearing is soaked." he said. Sure he had known I was diapered being my neighbor and all but still, talking about it humiliated me.
"I never knew his late wife wore a diaper and I was a bit curious plus it was a chance to get a full days pay so I said, "Okay, I guess.
I stripped down to my soaking wet diaper in the upstairs bathroom while Mr Maddox went to find something for me to wear.
He came back with and extra long pink ladies nightshirt and what had to be the thickest diapers in the world. "Sorry about this, my things are way too big for you but I found one of my wife's night shirts which should be good just for today."
Its true, he and by extension, his clothes, were far bigger than I was. He was at least six foot two compared to my five foot five and of coarse he was all muscle while I was practically skin and bones.
I changed out of the soggy rain soaked diaper and put his wife's diaper on. God was it thick and despite the pink shirt being little more than a ladies nightgown, I quickly put it on to cover the ultra thick diaper.
"If you want, I have dishes piling up in the kitchen. Should keep you busy for most of the day. Like I said, I have been falling behind on my upkeep." Mr Maddox suggested. And so, in a pink nightgown and disgustingly thick diaper I went to the kitchen to do the dishes.
He was right, there was enough to keep me busy for a while. I guess losing his wife had put him in a bit of a funk about doing the housework.
About an hour and a half in when I was getting the third load ready for the dishwasher, he asked if I wanted to have some lunch in the living room.
"Sure. Just give me a minute." I said and hurried with what I was doing and headed into the living room.
Apparently he had ordered a pizza while I was doing the dishes and was all set.
I sat on the couch and grabbed a slice while he put something on the flat screen for us to watch.
It was porn.
He then grabbed a slice of pizza but when he sat on the couch, I thought he would sit on the other end but instead he sat right in the middle of the couch right next to me. I was so put off my guard that I didn't say anything when he began rubbing himself through his pants.
"Were both guys right, we all do it?" he said to me and then asked. "Do you ever do it in your diaper?
Stunned by this turn of events all I could do was tell the truth. "Um, no. Just in the bathtub where mom can't catch me. You know, privacy and all. Plus my mom changes me and I dont want her to see that in my diaper."
"Bummer kiddo. I tried on one of my wifes diapers once to jackoff in. It was awesome. Go ahead. Give it a rub." And as he said it he unzipped his fly and pulled out his cock.
Not know how to react, I pulled up the pink nightshirt and rubbed the front of my diaper slightly and soon my dick started to tent my diaper while he stroked his cock while we watch porn.
"Have you ever been with a girl?" he suddenly asked.
"No, not really. You know cause of the..." I left it hanging.
"Girls don't really like a boy in diapers do they? Too bad for them. I find diapers to be hot. Have you ever been with a man?" he asked and then before I could say no he said, "You can touch it if you want to."
I didn't quite know what to do so I tentatively reached out and gently touched his cock with the tip of my finger.
"See, that wasn't so bad was it?" he asked and then he stood up and pulled his shoes, socks and pants clean off, his underwear too.
He then took my hand and helped me to my feet and I got up while still rubbing the front of my tented diaper. He then pulled me close and whispered, "I've been so lonely Matty without my wife, so lonely. I wanna take you to bed. Can I take you to bed?" and then he shocked me even further by planting a passionate kiss on me.
"I've never... I mean... I dunno... I mean I'm not gay... I dunno." I stammered but my dick was still hard in my diaper.
He took my hand and gently led me up the stairs to his bedroom and had me lay on my back then he proceeded to remove his shirt leaving him completely naked.
"Are you ready to have me make an honest woman out of you Matty?" he asked but it was rhetorical as he started to remove my diaper.
"Is it gonna hurt?" I asked confused and excited and afraid and humiliated all at the same time.
"Yes but that's why I treasure you and I have something to help with the pain a little." he said and reached into a drawer in the nightstand and produced a small round rubber ball with a strap running through it." Bite on this baby. And then he proceeded to gently place the ball gag in my mouth and secure the strap behind my head.
He then grabbed a tube of something and was soon on the bed between my legs. First one lubed finger went up my ass and then another and then a third and he was fingerfucking me.
"Are you ready baby?" he asked and all I could do was nod my acceptance.
He pulled my legs up onto his shoulders and placed his cock at my ass and started to push in. "Push out baby girl and I will just slide in."
I did as he said and pushed out and he slid in but it was painful and I practically screamed through my ball gag... but my dick was still hard as a rock.
He stayed hard in my ass without moving in or out for a few minutes while saying things like, "That's a good girl." and, "It'll feel better soon princess." and, "Your doing real good baby." and, "Oh my, what a tight pussy you have little girl." But all I could concentrate on was the pain in my ass and my own hard cock.
After a few minutes and as the pain began to subside, he started to really fuck me and I started to really enjoy it. I began playing with my dick and quickly shot a rope of cum all over the pink nightshirt I was wearing and he kept pounding my ass.
After what seemed like an eternity but was probably only a half hour or so he asked, "Are you ready my sweet darling?" and I knew he wanted to cum inside me and all I could do was nod yes.
His pounding increased like he was trying to tear me in half with his cock and soon I felt my insides filling up with his sperm. He then collapsed on top of me and we stayed like that for the better part of an hour before he got off me and went to grab another diaper for me.
"That nightshirt needs laundering so I grabbed you something else to wear sweetie pie." he said tossing what was obviously a dress on the bed next to me before he put another ultra thick diaper on me.
The dress was blue and came down to just above my knees and flared out slightly because the sewn in underskirt was very stiff. And it fit, except in the chest as I had no breasts. I suspected I was exactly the same size as his late wife. I had met her a few times but being a shy kid never really talked to her.
"Why dont you go and finish the dishes honey while I see if your clothes are dry." he said and then swatted me hard on my diapered ass to send me on my way.
Curiously, neither he nor I seemed in any hurry to remove the ball gag that was in my mouth. It wasn't uncomfortable so I didn't try and complain.
I did the dishes for another hour or so and then Mr Maddox led me back to the living room. He was still naked. The pizza had grown cold but I was still hungry and so I pointed to the pizza and then to the gag in my mouth. He quickly removed the gag so I could have another slice.
"So tomorrow kid, yardwork or housework?" he asked and I knew exactly what he was asking.
I wanted this to happen again but didn't want to seem queer so I answered "At least the house is air conditioned." and a smile crossed his face.
"Housework it is then, I'll lay out some things for you before you get here Matty. Actually, can I call you Missy instead? It'll be our little secret. You can call me Jim instead of that formal Mr Maddox all the time." he said.
"Umm, okay, sure I guess." I said feeling a little uncomfortable but also remembering the many times he called me something girly while he fucked me.
We sat and finished off the pizza and he even offered me some beer and I drank three cans by the time I had to head back home. When he paid me for the days work it was more than the ten dollars per hour we had agreed upon, it as double, two hundred dollars for ten hours.
I took off the dress and put my clothes back on noting that these new diapers were clearly obvious under my jeans as they were so damn thick. As I was noting that little problem, another one came up. After a full year of being dry during the day, I wet my diaper. It must have been all the beer, or maybe from getting plowed in my ass.
Anyway I went home with an ultra thick wet diaper on under my pants.
And mom, being mom noticed right away how bulky the diaper was and just had to ask if I had an accident.
"I was just gonna change myself and get some rest after working all day. I already had pizza at Mr Maddox's house." I said hoping I didn't have to endure another diaper change from my mom. It was bad enough she always changed me before bed.
"Upstairs mister." Was all mom said and I knew she meant to change my diaper. It was a routine of sorts, I strip and lay on my bed and wait for her.
She came into my room and grabbed a fresh diaper from the shelf next to my dresser, (One of the reasons I never had friends over.) and proceeded to remove my wet diaper.
"This is a new brand, did Jim next door give it to you?" Mom asked.
"Yeah, they belonged to his late wife and when it rained my diaper got all soaked." I answered.
"I see, humm, I also see you're quite red and irritated as well. It looks like you may have been having sex. Have you? Tell me the truth?" mom insisted but not in a harsh way, almost tenderly but still insistent.
After a little hemming and hawing as she put it she got the truth out of me, all of it.
"I see, so you have a boyfriend. Well, I'm happy for you. Tell me, did you like it when he called you Missy?" she asked inquisitively.
"I guess. It was just a game between us." I said. The air of embarrassment was killing me.
"All right then. You have had a full day and I will leave you to it. I have some shopping to do and if you need anything you know where the fridge is Missy." mom said calling me Missy.
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.