The Diapered Wife Pt. 01

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.