The Sissy Baby Princess Pageant

[littlediapersissy]

As his mother gently raised the front of the disposable diaper laid out just for him, 15-year-old Fred’s babyish knoblet stood to full attention. He could, of course, not help himself; why on earth would he deliberately become erect in front of Mommy, as he had recently been coaxed into addressing her? He had hoped the effort to lift up his bottom and simply let the extremely public diapering pass quickly, without notice, would overpower any other “special” feelings. But being on display at the Sissy Baby Princess Pageant - held annually, in secret, at an undisclosed location, and well-funded by a small group of extremely wealthy middle-aged women with an interest in the discipline of boys and men - in front of a massive crowd of hundreds of mostly women and girls, including many female classmates and the mothers of other classmates - made Fred feel very “special” indeed. As his mother Susan, a voluptuously large, gentle-eyed woman of 51, cooed at him, whispering bits of baby talk, it was as if she genuinely felt he were truly a baby - and involuntarily, he found himself breaking into a big, stupid, drooling smile, feeling warm, weak and submissive for his Mommy.

Some of this may have been a ploy to try to win the competition. Fred had been warned ahead of time on the scoring system for this section of the pattern. Sissy baby boys being diapered were rated on a scale of 1-10 in the following categories: Obedience, Babyishness, and Fit. A perfect 10 out of 10 would follow any and all instructions given by a woman or girl to the letter, be at all times an intellectual and emotional baby in his behavior for her pleasure, and will aid in ensuring that the diaper fits him tightly and snugly, giving a “cute” appearance that is the perfect accompaniment to ringlets, frilly panties and baby dresses.

On one side of the stage was a Nursery section, with full, towering stacks of enormously thick disposable diapers - the event was sponsored by both Pampers and Huggies, each of which had generously fabricated versions of their classic diapers fit for a wimpy teenage boy - rows upon rows of bottles of baby powder and baby oil, baby bottles, and baby food, a changing table ever-so-slightly angled towards the audience. On the other was the Sissy section, where rows of the girliest, frilliest, most babyish and humiliating dresses hung on full display, with petticoats and matching ruffled panties available in adjoining drawers - these horrors were still awaiting Fred, he knew. And a row of 9 other boys stood waiting in the wings to take his place - all naughty, unruly boys, all here decidedly against their will, wishing they were anywhere else. Fred’s case was special - or so he thought. His mother had caught him looking at sissy baby stories, pictures and art online, and was at first aghast that her son seemed excited not by pretty girls, but by the thought of being mommy’s pretty baby girl. Fred’s mother perhaps misinterpreted this as indicating that Fred literally wanted to be her baby again, only this time as a girl. And once she was set on this path, she became inflexible, determined to get every detail right to make her son’s sissy fantasies come true.

Fred’s diapering was almost complete. His mother seemed to delight in the display, slowly pulling open the tapes from each tab to cover the front of the diaper. Fred was simply mortified.  This crowd, comprised of so many irresistibly pretty women and girls, were not only witnessing him being diapered by his mommy; it was the main event! Peals of laughter rippled through the crowd at Fred’s intense embarrassment. There was not the slightest indication anyone in the audience sympathized with his plight as, essentially, their captive; they clearly believed he deserved this and more, given his weak, sissyish demeanor. Finally, the diapering was done, and as Fred lightly shifted his diapered bottom on the changing table, he could feel how thickly, tightly padded he was. Filled with despair, Fred found it hard not to take a strange solace in the possibility that this portion of the display would lead to him scoring perfect 10s.

It was, of course, customary that any sissy baby being diapered before a live audience would graciously thank his diaperer, before bestowing upon her a kiss. If the diaperer were close in age to the sissy baby - say, close enough for a crush to develop - the sissy was to, at most, blow a kiss, or kiss the foot, as intimacy beyond this is undeserved for weak sissy babies who belong in diapers and frilly dresses. If, however, the diaperer is the sissy baby’s very own mother, grandmother, or aunt, a kiss on the mouth is strongly encouraged - because all good little babies kiss their mommies, Grammies and aunties. “Fank you mommy,” Fred croaked, blushing furiously, as he awkwardly leaned in to kiss his beaming mother on the lips.

[sissykimmy1]

Fantastic start.  Love the premise.  I can't wait for more. :)

[littlediapersissy]

A bashful, sullen 16-year-old, Daniel had been told that the fellow contestants in the Sissy Baby Princess Pageant, like himself, were wayward youths, boys run afoul of their mothers’ authority. Despite besting Daniel’s terrible secret - one he would do anything to conceal, even given the extreme nature of this situation - was that this very scenario was his personal fantasy. That is, to be put into thick, embarrassing, crinkly diapers, ruffled panties, petticoats, a pretty dress, and the kind of Barbie pink makeup a toddler girl might eagerly wear, by his dearest mother, on full display of the entire female contingent of his school and neighborhood. He knew it was absurd, ridiculous, self-destructive - he could do nothing to bury this intense urge to be humiliated and paraded around.

Most embarrassing of all, many of his fantasies culminated in being “paired off” with a fellow sissy baby, a boy whose fervent adoration of diapers and little girl dresses shone brightly as his. Daniel stood just offstage in an outfit just little girl enough to be embarrassing but mild enough to lend sharp contrast to what was to come: a Dora the Explorer t-shirt, pink corduroy pants, and underneath them, Disney Princess panties lined with lace. As he observed wimpy young Fred kissing his mother on the lips, Daniel could not keep his “Mr. Noodle,” as his own Mommy called it, from standing to attention. Deep in his heart of hearts, Daniel liked Fred - pretty, prissy, weak, whimpering, babyish Fred. Did he *like* like him? Daniel wondered if he was losing his mind, admiring the thickness and tightness of Fred’s gigantic Pampers, the fun, cute nursery-print design on the front tapes featuring smiling cartoon characters he vaguely recognized, the crinkliness of the diapers, or - *gulp* - what Fred might look like in one of the many adorably pretty dresses on display.

“What a sweet sissy baby he is!” Daniel’s mother remarked at Fred and Susan’s kiss. “I hope you have a big wet ready one for me, sweetie,” she remarked to Daniel, tightly gripping his arm. Daniel’s mother Nicole, 44, was blonde and heavyset, wore glasses, copious makeup that made her intimidatingly expressive, and was at once lilting, mocking, and a little crazy. “No way,” Daniel mumbled, trying to tear away from her subtly enough to prevent a response. “Excuse me, sweetheart?” she loudly remarked, cupping her hands to her face in a mock-gasp. “That doesn’t sound like something Diapered Danielle would say!” Daniel was in disbelief; his face blushed beet red. How did she know? “How did…” he found himself muttering aloud, unable to finish the sentence. “How did I find out you’re nothing but a big sissy?” Nicole continued for him, grabbing his arm again - this time, he could not release himself from her grip. “How did I know you love to visit websites where boys and men dress like baby girls? How did I know that all this time, with your sullen demeanor, you were just trying as hard as you could to hide that you wanted me to dress you in diapers, frills and lace - and you still couldn’t? That you were too much of a stupid wimp to bother deleting your browser history?” Daniel screamed, “I’m NOT! I’m NOT!!!” He sank to the floor, and his mother could only laugh. “Oh but you should be happy, sweetheart - all your dreams are about to come true.”

[Sissieann]

 8) I love this story more please Kevin.  ;)

[sissy servant 737-820-633]

Oh my Goddess, the fear and pleasure of being a diaper loving sissy..in a pageant no less with a fellow sissy as well.. One can only wish for moments like this. :-[

[krystalasbaby2017]

Lovely story love to see this continued to see where it leads with the two new sissy babies

[littlediapersissy]

Thanks to all of you for your sweet words of encouragement - and a special thanks to sissy servant for that wonderful picture.



Now that Fred was effectively imprisoned in his extra-thick Pampers, with his mouth freshly kissed and smeared with lipstick by his doting Mommy, it was time for a few accoutrements. Susan first placed a pink, lacey bonnet atop her teenage son’s head, from which a small rubber object lightly dangled. Fred would not realize it was it was a Minnie Mouse pacifier until Susan had brusquely shoved it in his mouth, and the crowd roared with approval. Susan turned to them, gave a wide smile and announced, “I present to you my sissy son, who will henceforth be named Felicity!” Fred - was that really his name any longer? - was so shocked that he couldn’t help but open his mouth in astonishment, his pacifier falling out; it was lucky for him that his Mommy was present to place his pretty binkie back into his mouth.

“Buuuh maughhhyy!” Was all one could hear shouted behind Fred’s pacifier; it was, of course, presumed that he meant to say “But mommy!” This drew the biggest wave of laughter at the event thus far.

“Wasn’t Felicity just a trooper for her diapering? I was surprised — her itsy bitsy ‘thing’ looks so tiny most of the time, but as soon as her Mommy starts putting fresh Pampers on, suddenly it’s so stiff, I could hardly fasten the tapes on her diapers!” More squeals of delight could be heard from the audience - and some seemed oddly familiar to Fred. It had a lightness, a hushed quality - could that have been Kate?!

Fred had feelings for many girls - okay, the immature wimp melted at the chance to talk to *any* girl in his class at high school. But he sometimes imagined that there was no girl on earth for whom a boy’s feelings were so tortured, so intense, so feverish, as for Kate. While publicly, Fred poked fun at Kate, taking every opportunity to put her down, privately, he found himself fostering a maddeningly intense crush on her. He had never felt anything so intense for any girl before, and yet he felt he had to keep up a facade of superiority. For Kate was a girl of contradictions: in many ways traditionally beautiful, tall - taller than Fred - extremely slender, blonde, always wearing a touch of lip gloss that made a strong contrast with her pale skin, she was also shy, awkward, and perhaps seen as stunted, donning pajamas to school until just recently, wearing extremely feminine clothes at odds with her quietness and plain, muted features. One day, Fred went from finding her risible to being mesmerized - and there was no turning back. Her being at this terrible, humiliating event was just about the worst thing he could conceive of - it was awful beyond imagination.

“And here to judge Felicity on her the Diapering round of this year’s event,” Susan continued, “is one of his schoolmates - in fact, Felicity has a big crush on her.” Fred froze, began to sweat and feel hot and cold all at once. Could it be? No, it couldn’t… no… No!! The teenager involuntarily trickled into his Pampers. “Hi Fred,” he heard Kate gleefully offer to him in her quiet, awkward voice, as she climbed the steps to the stage. “Or should I say Felicity? All this time, I thought you wanted to kiss me. Oh, you thought I didn’t know? I guess it turns out the whole time, you really wanted to kiss your Mommy. I don’t blame you - she’s so pretty!” The crowd was putty in Kate’s hands.