Diaper Sissy Stories
Here’re 4 diaper sissy stories for you:)
Grandma’s Pet Project Pt. 01
So here is another perversion from my perverted mind. This one involves the willing sissification of a nancy boy at the hands of his grandmother. Please feel free to leave a comment or at least rub one out when you’re done reading and don’t forget to swallow.
Damn, I was really gonna enjoy this. I needed it, I needed it badly. My moms stockings were wrapped around my ankles and around the foot post of my bed keeping my legs wide open. I was wearing one of her bras which was way too big but I didn’t care. The pièce de résistance was one of my aunties ultra thick crinkly diapers.
I don’t know why masturbating in a diaper was such a turn on for me but it was. Ever since I had discovered porn when my parents gave me an iPad for my eighteenth birthday I had been hooked. Aunt Sophie had lived with us for a couple of years and there were several packages of her diapers up in the attic and I just had to try one on when I saw diaper sissy porn for the first time.
Today I needed it more than usual. It had been a long day at school. It had started in the locker room like it often does.
“Hey limp dick, the showers are for men, not pathetic Nancy Boys.” was the comment that started the teasing this time. It was always something like that, some comment about my small penis or about my lack of interests in sports or shyness around girls.
I had endured teasing and hazing growing up for my small and girly body but today the other students had forced me to wear my towel up around my chest like a girl does when I finished showering after phys ed.
Coach Benson was no help, oh he put an end to the teasing but he also looked at me with contempt and often told the other boys “Some boys are just sissies, that’s how the world works so leave him alone.” Not very helpful.
So I needed to unwind and that’s why I was about to rub one out. I preferred to rub myself because my dick was only about three inches when hard and it was far easier to rub myself, especially through the thick padding of the diaper than to actually jack off.
I reached down and began to touch myself through the thick padding enjoying the loud crinkling sound as I did. My little dick was already hard and I knew I would come real quick like I always did.
I began to moan loudly knowing I was safe from discovery as my parents were still at work and wouldn’t be home for several hours at least, It having been a half day at school. I reached over and grabbed the giant teddy bear my grandma had given me for Christmas years ago and placed it between my legs and started to diaper hump it.
I loved the feeling of my teddy bear between my legs, especially when my legs were spread apart and tied to the bed. The teddy bears head was perfectly aligned with the bra I was wearing and I always mashed the head of the bear into my bra while diaper humping. It felt right doing it that way.
I let out a long moan as I ejaculated into my diaper.
“I knew it, your a faggot. What the hell do you think you’re doing?” my dads loud and angry voice yelled at me spoiling the afterglow as I held my teddy bear tightly.
Startled, I hurriedly tossed the teddy bear on the floor and grabbed my covers and pulled them over me to hide my shame but it was already too late. He grabbed my covers and ripped them off me exposing my diaper and bra.
“I knew it, I just knew it. The school said you were just a late bloomer and the coach said you were just bad at sports and even your mom defended you saying you were just a shy kid but I knew you were a fag. You’re a homo and I’m not having a homo in my goddamn house.” He said with even more rage if that were even possible and then grabbed me by one arm and pulled me bodily off the bed.
I was pretty sure he sprained one if not both of my ankles as he pulled me from the stockings that had secured my legs to the bed.
I was dragged out of my bedroom and down the stairs. He moved so fast that I never had time to fully stand up and so I found myself bruised from being dragged down the stairs. Then I was bodily thrown out of the front door.
The last words I heard from my dad were, “And don’t ever come back.”
Bruised and half hobbling from what I was sure were sprained ankles and wearing a bra that was way to big and a snug diaper and with nowhere to go, I actually started to cry.
I tried to think of something to do. Grandma’s house was only about five blocks away but I only had on a diaper and a loose fitting bra. Still it was better than nothing. I didn’t want anyone to see me like this.
I yelled, “Can I have my clothes dad, please?” but he never answered even though I knew he had heard me since he was clearly visible through the living room window sitting in his favorite chair in front of the television.
When it was clear to me that dad wasn’t gonna let me back in or give me my clothes, I took off running towards my grandma’s house. I don’t know how, but I made it without being seen. By the time I got there, my ankles were sore and the bottoms of my feet were raw from running barefoot on the concrete.
I was again crying as I pounded on grandma’s door begging to be let in.
“For heaven sake, what’s all the excitement?” she exclaimed as she opened the door. The look on her face was pure surprise when she asked, “Jamie, is that you?”
“Dad kicked me out and I don’t have anywhere to go. Can I please come inside… Please?” I begged still half crying from humiliation and the pain in my ankles not to mention the bruises all over me from being half dragged down a flight of stairs.
“James Francis Willow!!! What have you gotten yourself into?” she said using my full name which was never a good thing.
“I was… I mean I just… Dad caught me… Can I come in please?” I stammered afraid to be seen outside and not knowing how to explain myself.
“Hmm, I think I’ve a good idea what happened. Well come on inside before the neighbors get an eyeful of you.” she said stepping aside to let me in. I was so glad to be inside.
“Have a seat on the sofa and I’ll see if I have anything for you to wear. I’ll see if I have anything for those bruises as well but I think a trip to Urgent Care or even the Emergency room might be in order.” she said before heading upstairs. I flopped into the pillowy softness of grandma’s sofa and grabbed a comforter to hide my shame.
My tears had largely dried up by the time grandma had come back downstairs with a handful of clothes for me to wear and some Tylenol.
“These should do for now, I don’t have any boys clothes so you’ll have to wear a dress or go naked. They belong to your cousin Angela. Her underwear is too big for you so you’ll have to make do with that diaper for now. Here take these.” she said handing me the clothes and Tylenol.
I removed moms bra and pulled the white slip and yellow dress over my head and then took the Tylenol and washed it down with a glass of milk that grandma provided.
Grandma left me alone while she made a few phone calls, before coming back.
“I talked to your father and he explained what happened. I think he severely overreacted. It’s normal for boys to want to explore. Anyway he said you cannot return home or have your clothes back. I also called my doctor and explained what happened to you, he suggests you come in right away and have those ankles looked at.” she said tossing me a pair of fluffy bunny slippers that I knew also belonged to my cousin.
“I think I’ll be alright if I stay off them for the rest of the day.” I said having no wish to go back out into the world, especially in my cousins yellow dress. I did put on the slippers.
“NOW MISTER. Lets go.” and that was that. I knew when bargaining with my grandma was futile, something about her tone that left no room for debate.
So wearing my cousins yellow dress and a white slip over a crinkly diaper, my grandma led me out to her minivan to drive me to her doctor.
The frilly ruffles of the shoulders and neckline of the dress made me ultra self conscious as we drove and all I wanted to do was crawl under a rock and hide.
The doctor was a family practitioner and it was obvious by the decor in his office that he catered to women and children. There were plenty of posters about safe sex and a few about how to help battered women.
I was ashamed as I sat waiting. It was obvious to anyone that I was a boy and there were several other people waiting in the office. One woman was there with a five or six year old girl who promptly asked her mom, “Why is that boy wearing girls clothes momma?” while pointing at me.
“Shh, it’s not polite to point. Some boys just like pretty dresses, just like girls do.” the little girls mother said.
The little girl seemed to accept what her mother told her and went back to coloring in her book while they waited.
Finally a nurse came out and called my name: “Jamie Willow, the doctor will see you now.”
I had hoped that my grandma would let me go in alone but no such luck. I hobbled on my sore feet as grandma followed the nurse and myself to an exam room.
I had my vitals taken and then was made to sit on an exam table while I waited for the doctor. Grandma waited patiently on a chair.
There was a small knock on the door and the doctor let himself in. “Mrs Violet, how are you? I was surprised to receive your call. Tell me what happened?” the doctor asked then said to me, “I’m doctor Manly.”
I didn’t answer as I was too humiliated. Grandma spoke up saying, “He was doing what all boys do when his father caught him and tossed him out of the house half naked. I’m afraid he may have sprained his ankles or worse.”
The doctor examined my feet and proclaimed much to my relief, “Well, they are certainly bruised but I don’t think they are broken or even sprained. Some cold compresses and a little rest would be advised. Have him stay off them for the next few days. Since tomorrow is Friday, you might just keep him home from school, that will give him the weekend to rest up and by Monday he should be fine.”
“That’s a relief doctor, I was worried when I saw those bruises.” grandma said.
“The other bruises are superficial but I am afraid there are certain legal matters we must discuss. I am obliged to report any and all suspected domestic abuse and if needed to refer the victim to a battered womens shelter. They will make accommodations for a battered boy.” Doctor Manly said.
“He’ll be staying with me and his father wants nothing to do with him so I can’t imagine any further problem.” grandma said.
“Good, very good but I still have to report this. I will also need to do a pelvic exam.” he said.
“Of coarse doctor.” my grandma said allowing the doctor to examine my… Well I didn’t exactly know what he would examine.
“Jamie dear, normally I would have you bend over for this but seeing as you need to keep off those sore ankles of yours, why dont we go ahead and use the stirrups. Just lie back and place your feet in the stirrups for me.” the doctor instructed.
Great, more humiliation all though neither he nor my grandma was mean or cruel, far from it, both were quite sympathetic but it was humiliating nonetheless.
I lay back on the exam table while the doctor helped me put my feet up in the stirrups.
Doctor Manly took one look at what I was wearing under my dress and said, “I see he’s experimenting with diapers, that’s quite normal. You might wanna keep him in them for the weekend at least so he keeps off his feet.” then he untaped my diaper and began examining my entire nether regions going so far as to put a lubed up finger up inside my ass which made my dick spring to attention.
“That’s quite normal, no need to be embarrassed.” he assured me.
When the pelvic exam was finished, he had a nurse come in and put another diaper on me. This one was far thicker than the one I had been wearing. She also put cold compresses and ankle wraps on me.
When my exam was concluded, the doctor offered me three large bags of MegaMax diapers and a prescription for some painkillers and made a follow up appointment for me in two weeks.
“Now if his feet are still tender Monday, feel free to keep him diapered at night so he doesn’t have to wander around the house when he needs to pee.” he said.
Finally it was over.
I knew my grandma meant well when she said, “Well, at least with those extra thick diapers the doctor gave you, your cousins panties will probably fit you now. At least the ones she wore when she was younger, the ones with frilly lacy ruffles.”
Ugh. How bad was this gonna get?
When we got back to grandma’s house she told me I could stay in cousin Angela’s old bedroom. I made my way upstairs and was greeted by the girliest bedroom one could possibly imagine. Pink walls, pink linens on the bed, pink pillows, closets full of pretty dresses, large vanity, lots of makeup, girly dolls everywhere and drawers full of girly underwear. There were even posters of men flexing muscles.
There was also a drawer full of sex toys.
I was still engrossed with exploring my cousins room when grandma came in and grabbed a nightgown from the closet and handed it to me.
I took off the yellow dress and accompanying slip and pulled the nightgown on over my head. Thank god it reached all the way down to the floor but unfortunately it was ungodly feminine with ruffles and lace everywhere.
“Off your feet means in bed… Now!!!” grandma instructed as she pulled the pink comforter and sheets down for me to get into bed which I quickly did if only to cover up from the shame of wearing a nightgown and diaper.
As I lay in bed, grandma began opening the packs of diapers and placing them on a shelf moving aside several of my cousin’s picture frames and nick nacks to make room for them. She then went to the vanity and opened the drawer which held the sex toys and grabbed a handful of them and came and sat on the side of my bed.
“Now it’s painfully obvious that neither my daughter nor that disgusting brute of a husband she married ever talked to you about sex so I’m gonna have to. Your cousin, my granddaughter, Angela talked at length about sex. I guess women talk more about things like that then men do but since your currently wearing a nightgown like a girl, why dont we pretend to be mother and daughter and have ourselves a little talk, shall we?” she asked as she dumped her handful of sex toys on the bed next to me.
I didn’t say anything. What could I say. I was wearing a nightgown and a diaper and way to mortified to speak.
“Good then, lets begin. You like playing with yourself while wearing ladies things and a diaper too… yes?” she asked. I just nodded.
“We cannot have a conversation if all your gonna do is pout. I want you to actually say things, not just nod your head. Do you understand me young lady?” she said emphasizing the young lady part.
“I guess so. It’s just embarrassing.” I said.
“That’s why we talk, so you won’t be embarrassed. Angela told me all her desires and we talked often. You might not know this but it really is quite normal for boys to experiment. Now you tied your legs to the bed, do you like being tied up?” she asked me.
“I guess so. I saw it online and wanted to try it. It was fun.” I admitted.
“Being tied up is fun for both girls and boys. Have you been with a girl or boy yet?” she inquired.
“No.” I answered but then added, “Girls think I’m to sissy and boys just tease me all the time. If anyone saw me running over here or riding in your minivan wearing a dress, I will get killed when I get back to school. Can I take the rest of the year off? I have enough credits to graduate, it’s only five weeks?” I asked almost pleading.
“So you’re afraid to go back to school? That’s understandable. Tell you what, I’ll make a deal with you. You agree to a few terms and school is officially over. What do you say?” she offered.
“What kind of terms?” I asked hesitantly.
“One, I get to sissify you. Two, I think I will keep you diapered, at least for peeing and three, you have to be honest with me all the time, no matter what. Do we have a deal?” she asked.
“Sissify? You mean turn me into a girly boy?” I asked afraid and excited.
“Not just a girly boy, the frilliest and feminine girly boy imaginable. I used to love seeing your cousin in her adorable dresses and I believe you would fit into them without much trouble. And I know you want this even if you won’t admit it. Well… Yes or no?” she pressed.
“Would I have to wear a dress or girly things outside?” I asked.
“Yes, but I promise that you will look so much like a girl that no one will know you’re a boy. You already look like a girl anyway. Just look at you, long hair that when styled properly will be quite feminine, pretty face that with the tiniest amount of makeup will be quite adorable, hairless legs than men would love to stare at, small delicate hands just like a lady. You’re practically a girl now and certainly a sissy so why not just go with it?” she explained.
Her assessment of me was both painful and accurate. Everyone always called me a sissy anyway. But wear a dress and makeup and wear a diaper all the time?
I thought about it for a minute and asked, “Do I have to decide right now?”
“Why don’t you sleep on it. See how it feels to sleep in a nightgown. Tomorrow morning I’ll change your diaper and you can wear a dress for breakfast. It’ll just be us two girls.” she suggested.
“Okay, I’ll think about it.” I said.
“It’s settled then. You get some rest and feel free to use your cousins toys.” she said.
Grandma left me alone with my cousin’s sex toys and me under the covers in a diaper and nightgown. I thought about wearing a dress all the time and looking like a girl and the thought made me excited.
I took one of the toys, a smaller flesh colored rubber cock and put it in my mouth to see how it felt. I then reached under the covers to rub myself through my diaper. I took a bigger rubber cock, a black one and placed it between my legs just to get a feel for it.
Then I did the unthinkable, knowing I was supposed to wet my diaper as per the doctors orders that I stay in bed and partly because grandma seemed to want me too, I let loose a stream of warm pee into my diaper. It was erotic.
I rubbed myself till I exploded in my diaper never taking the rubber cock out of my mouth.
The orgasmic afterglow had me drowsing by the time grandma came to bring me dinner and check in on me. I had the black cock shaped dildo in my hand when she sat my dinner tray on the bed.
I decided then and there what I was gonna do and told grandma, “Okay, I’ll do it, I’ll let you sissify me.”
She smiled and said, “You’re such a good girl, I knew you’d agree. We’re gonna have so much fun. can’t wait to get you into the salon and have your hair done.”
She looked under the covers and saw my wet diaper but only said, “You’re good for now.” and left me to my dinner and thoughts of sissification.