Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: Baby Bobby on October 28, 2025, 11:16:48 AM
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When I was younger, about twelve, my parents divorced, which, needless to say, upset me greatly. Unfortunately, at about that time, I began wetting the bed, not every night, but generally about three times a week. My mom took me to doctors, put an alarm in my room, but nothing seemed to help. She finally decided on the very practical solution of diapers and plastic panties.
One day, she came into my bedroom and cleared off my dresser top with its airplane models, replacing them with stacks of fluffy soft cloth diapers, baby powder and diaper rash cream. My top drawer was soon filled with a variety of plastic and rubber panties, in many different colors and patterns.
The first night she decided to diaper me, I argued with her and put up quite a fuss but she responded by yanking me over her knee, pulling my pants down and spanking me until I cried. With my bottom blazing, I willingly submitted to her pinning me into a thick set of diapers and following it with yellow nursery print plastic panties. It made me feel very babyish and humiliated, and that night, I was determined to keep them dry, to prove to her that I was a big boy.
Alas, I woke up the next morning with soggy wet diapers but my mom was no longer angry, since the sheets were still dry. She unpinned my diapers, depositing them in my new diaper pail, and she let me begin my day as usual.
That evening, she took me into my room and began our new nightly ritual of her undressing me and putting my diapers on. At first, this took place right before bedtime, but as time went on, she began getting me ready for bedtime earlier and earlier in the evening, so that I often watched TV in just my pajama top and diapers.
My mom’s younger sister lived two houses down from us, so it wasn’t long before my secret was out. She came in one evening unannounced, and caught me lying on the floor, my fat, shiny diapers in plain sight as I was watching a Disney movie. I gasped in shock and humiliation, scrabbling to my feet to try and escape but she immediately ordered me to come back and face her. My aunt has always been very strict and I never had the nerve to stand up to her.
Keeping my eyes downcast, I reluctantly and slowly waddled back to her, my cheeks blazing hot with shame at being caught like this.
“Well...looks like your mommy finally decided on diapers and plastic panties for your bedwetting. I think it’s just what you need and deserve, don’t you?”
I shuffled my feet and swallowed hard, unable to return her imperious stare.
“Y-yes, Ma’am,” I mumbled obediently.
“Maybe wearing diapers like a baby will make you try harder to stop your wetting, hm?”
My cheeks and chest were a deep red as I nodded submissively.
It wasn’t long after that when my mom had one of her friends over to visit after dinner. At about 7:30, she informed her that she had to get me ready for bed (even though my bedtime wasn’t until 9:00) and she took me by the hand and into my bedroom. Curious as to what was in store for me, her friend followed us and she got to watch as my mom undressed me and laid me down onto a triple set of diapers.
“Bobby has started wetting the bed and this seems to be the most practical solution,” my mom told her.
I fidgeted nervously and tried to look the other way.
“Aww, lots of little boys wet the bed, sweetie,” she told me with a smile, “This will make sure your bed stays nice and dry.”
I blushed hot with shame, not the least of reasons for being called a ‘little boy’.
And this was doubly mortifying for another reason—ever since kindergarten, my boyish genitals had refused to grow any further and they were still very much the same size as when I entered the first grade. As a consequence, when my mom lowered my Spiderman undies and sat me down on the stack of diapers, her friend got a good look at my embarrassing, tiny little package. Even when fully erect, I was no bigger than an inch and a half and when feeling vulnerable like I was now--they shriveled up like three little marbles.
Her friend put her hand to her mouth to stifle her giggle and I felt my eyes misting with tears of shame.
After powdering me and pinning my diapers in place, my mom stood me up to have me step into my waiting plastic panties. I can still remember these—they were shiny white with colorful nursery characters that seemed to scream that I was just a big baby that couldn’t be trusted to keep my bed dry.
It wasn’t long after that, that my mom’s other friends also found out about my nightly diapers and it became my humiliating task to wish them a goodnight whenever they were over for the evening, dressed in just my pajama top and embarrassing pampers. Some of them found it amusing or cute and some shook their heads at my babyish attire.
I’m not sure which was worse; Their smiles and acceptance that I was a big boy who needed diapers or the ones who just thought I was pathetic for needing them.
My mom got a vinyl mattress cover for my bed and before long, my room began to smell like that of a chronic bedwetter’s.
Often times, my aunt (who I thought was very pretty) would babysit me and I can still remember accompanying her once for a long day of shopping. We were on our way home and I had been holding my need to go pee for at least an hour when finally, I just couldn’t hold it any longer. As a result, to my utter shame, I humiliatingly wet my pants. I thought I might be able to hide it from her but when we went inside, she immediately saw the big dark spot on my pants and scolded me roundly for it. Taking me to her room, she yanked down my wet pants and underwear and placed me on a waiting stack of diapers. With one hand, she held my ankles firmly over my head and with the other, grabbed her oval wooden paddle that she always seemed to have nearby. Six blistering swats were delivered to my bare bottom as I yelped helplessly and howled in pain. I cried like a baby as she powdered me and pinned my diapers in place, followed by a stretchy pair of pink rubber panties.
“Looks like you need to be wearing diapers during the daytime too,” she said sternly, “Your mommy and I are going to be having a talk about this.”
From that day on, whenever my aunt babysat me, I was put straight into my diapers, regardless of the time of day.
Unfortunately, I was soon to become the architect of the next measure of discipline applied during my upbringing. Although I was very intimidated by my aunt, I also found her curvy body very exciting, especially for a young boy like me, in the throes of puberty. Her big, thrusting breasts--which she made little attempt to hide, were frequently the stuff of my boyish fantasies. As a result, it was not uncommon for me to experience an erection during my diaper changes at her house. She would inevitably scold me with annoyance and tell me such things were inappropriate for a boy still in diapers.
Then one day while changing me--before she powdered me, I watched with apprehension as she picked up a strange, small steel ring and she pulled my tiny little package through it. Then, taking a short, cap-shaped metal cage, she placed it over the quivering head of my pen-is and mated the two pieces together, locking them in place with a long key.
Although it didn’t hurt, I could feel it compressing my shy little nub and instinctively, I knew my tiny erections would now be out of the question. I squirmed and whimpered as she powdered me and pinned my fat, sissy diapers around my hips.
“There,” she said with satisfaction, “That will put an end to that nonsense—once and for all.”
Little did I realize how significant that moment would become. Up until then, I had been a chronic masturbator, using my soft, fluffy diapers for my own guilty pleasure. But I soon learned that this terrible device would make sure I was both erection- and orgasm free from now on.
Just the next morning, I woke up in my usual soggy wet diapers, but my baby-sized pen-is was throbbing with need inside its new steel prison. No amount of rubbing the front of my plastic panties could produce the kind of stimulation I had become accustomed to. Finally, I gave up in utter frustration.
Frustration was to become my daily lot, since my aunt often babysat me, and I was constantly being stimulated by her sexy body—yet, completely unable to do anything about it. No amount of begging her to unlock the device would change her mind and in fact, one time when I became particularly fussy and defiant, she pulled my diapers down and took me over her knee. I kicked and cried like a baby as she soundly paddled me, lecturing me on how bedwetting sissies didn’t need to be playing with their wee-wees.
There were several other times when I had accidents during the day, so my mom agreed with my aunt that my wearing diapers during the day made sense and my big boy underwear were simply thrown away. It was so difficult, trying to keep my diapers a secret at school, as the slippery, shiny vinyl was always threatening to peek out of the top of my pants. Of course, it couldn’t stay secret forever, and one time, when a bully yanked my trousers down in the cafeteria, everyone immediately learned what I wore every day. From that day on, I was known as the ‘sissy diaper boy’ at school and my incontinence only got worse.
Although during the day, I was expected to notify my mom or my aunt when I had to use the bathroom, I began becoming more accustomed to my diapers and the number of ‘accidents’ started becoming more frequent. Sometimes, I would be watching TV and would get up—only to discover the seat of my diapers were soggy wet. Other times, it seemed to happen whenever I was surprised by someone or something. Inevitably, I would wet myself in fear before I could stop it.
More and more, my mom seemed to accept it as part of my sissyish personality and my diapers were changed with little more than a scolding.
At home, she stopped making any effort to hide my diapers, and I usually wore just a t-shirt and sneakers around the house. However, my aunt liked to buy tops for me that looked childish and went with my diapers. She loved matching outfits, like the baby blue Barney top with white frills and matching sissy panties she got for me. Once again, I could offer little resistance as she pulled the soft, babyish outfits over my upraised arms, the short, puffy sleeves and toddler motifs on the front making me look all the more immature.
It was on my birthday that she presented me with a particularly humiliating gift—a pair of shiny black Mary Janes and white lacy anklets to go with them. This time, I put up a fuss and ended up over her lap again, getting a blistering hot birthday spanking for my efforts.
That was how I spent the rest of my teen years—as a diapered, chaste sissy, firmly under the strict discipline of my mom and my aunt.
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This deserves more attention. Lovely!
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I am having a "wish it was me" moment. Excellent story!