Betty Pearl's Sissy Stories 20.1

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=> Topic started by: rt76209 on August 14, 2018, 03:50:58 PM

Title: Once Upon a Time....
Post by: rt76209 on August 14, 2018, 03:50:58 PM
Once upon a time….
I

It was time for the routine inspection of apartments, a thing they did periodically and only after letting the residents know about when they’d be conducting the walk throughs. It was a cursory glance to inspect for damage and what not-nothing exhaustive. The managers fanned out with maintenance men in tow and walked through a maze of apartments in various and unpredictable states of upkeep. It was at times refreshing and at times, made one want to shower.

One unit on the list was in good repair, quite clean and tidy. The only remark was to wonder when and if the tenant had got permission to paint the very tasteful accent wall, but no issue of a reminder to change it back. The occupant of the unit obviously cared for it quite well.

The worst that could be said was that he didn’t always put his clothing away and that was quite a curiosity. There were no children listed as living in the apartment and the juvenile clothing that was on a freshly made bed and a bathroom floor was clearly not of a size that would fit a child. It did correspond to roughly the size of the meek, but ever so polite resident of that apartment. And, this was not some sort of a “fashion” item that might simply be mistaken for baby clothes-these were adult sized, baby clothes. Her curiosity peaked, the manager checked inside a kitchen cabinet or two, a level of scrutiny not all apartments received, and her curiosity was rewarded-baby bottles. 

The resident was a good tenant, paid his rent on time, never a complaint, so there was no reason to see the curious items as anything nefarious that might require action. But, she did want to know more.

The resident got home pretty predictably at around 5:30. The manager showed up at 6.  She knocked on the door. He answered, still dressed from work, in casual clothes, nothing hinting at the very different clothing choices she had observed earlier. She asked if she could speak to him and he invited her in, asking, as a good host, if he could get her anything. As he started for the kitchen, she noticed that as he turned around the slacks he was wearing were not loose in the back, at least not as loose as she would have anticipated and might even have looked like they were stretched over a puffy fabric underneath.

He invited her to sit as he returned with a glass of wine he had poured for himself and again, offered her the same. She once again declined and silently wondered if he had forgone the baby bottle on her account. She started the conversation by mentioning the inspection walk through and then immediately going to the subject of the accent wall. She complimented it, but asked from whom he had gotten permission to paint. He related the details, it had been with a prior management company and then, his speech halted for a moment and he had a very, very brief, but visible, moment of concern. The manager didn’t miss it. She knew that in his mind he had just completed the inventory of what was visible while he was away. She did not leave him hanging.

He had slumped slightly in the chair, a thoughtful gaze had taken over his face where before he had been looking the manager in the eyes with a cheerful gaze.  She had sat upright, hands in lap, an air authority that could not be missed….

“I saw some interesting clothing items, can you tell me about those?”

She had not given him time to concoct a story. She added, somewhat deceptively, that they had concerned her as they might indicate some latent interest in children and require reporting to the proper authorities. He could not have known that her interest was purely personal and that she knew he was harmless; he felt obliged to offer an explanation, only enough he hoped, to dissuade her from any revelations.

As he began to speak, it occurred to her that he was shrinking, shrinking into the chair. It was obvious he very much wanted to shrink away from her stare, which he did his best not to meet. He apologized for leaving the clothes out. He did his best to effusively plead that he had no interest in involving children, an idea she had already settled against. He explained that he only wore those things behind closed and locked doors and involved no one else. It was his personal escape.

She could see a tear forming in his eye. It brought a couple of conflicting emotions to the surface-a maternal sympathy and….something that wanted to see him even further reduced.  She stood, urged him to continue in his exposition and as he spoke, she picked up his wine glass and took it to the kitchen. He didn’t know why, but a part of him thought, “…maybe she knows I’ll need more after this is over.” He was wrong-she made a show of pouring the wine in the sink, while looking him in the eye and without losing his gaze, retrieved the baby bottle from the cabinet and, filling it with milk, returned to sit, holding it for him to grab. He timidly reached forth a hand, to which she offered the correction, “NO. Both hands.”

It was her turn. She questioned him on how long he had indulged this interest. She asked what all he had in the apartment and where it was hidden, making sure to ask in such a way that it sounded as if she already knew and was simply testing his honesty. He didn’t fail the test, relating the location of diapers, plastic pants, pacifiers, adult baby videos, and other things he had never wanted found by anyone.

She stood, looking down on a grown man suc-king on a bottle of milk and openly crying. The power she felt at that moment was like no other she had felt to that point, it was intoxicating. She still felt a sympathy, but she was not about to let him up now, she had no intention of not enjoying to the fullest that which was coursing through her at that moment. She became faintly aware that it was likewise tingling her in places that might not have been so affected by a grown man, suc-king on a bottle and crying.

She spoke with the same quiet authority, knowing he would offer no resistance, “Take your bottle and go stand in the corner. Do not speak; do not turn around; do not do anything until I call for you. Do you understand?”

He knew, somehow, that an affirmative nod was best.

Having deposited him in the corner, she went to the closet where he had indicated the remainder of his collection was hidden. Right there behind the long coat and the bathrobe was a small, set of plastic drawers. Opening them revealed that he had an affinity for pink. There were disposable diapers, plastic pants, all he had mentioned and some other items he had neglected to mention. She took her time, the look in his eyes as she had turned him to face the corner assured her that she needn’t hurry.  A sniffle from the other room confirmed the spell was holding.

After she had inspected, she returned and standing behind him she noticed a smell, slightly of ammonia and she knew instantly, without even turning him around, that he had wet his pants as he stood in the corner. She could not have denied that she felt a power over him, she had no idea it was strong enough that he would not ask to use a bathroom. Her command to not speak had been one she hadn’t bothered to think would be obeyed to the point of abject humiliation, but here it was-a grown man, face turned to a corner, with a bottle of milk wearing pants he has just pissed. The tingling she had earlier noticed was now a decided throb. She determined then and there, that this was going to continue.
Title: Re: Once Upon a Time....
Post by: rt76209 on August 14, 2018, 03:58:56 PM
Chapter 2

She had determined to play this as far as it would go and moving her face close to the back of his head, still turned to the corner, whispered, “Did you wet your pants, little man?” The words carried a bite that the tone of her voice, a bit of a lilt, did little to soften. He sniffed again and meekly nodded. He had no fight, hadn’t much when she first broached the subject-the attack had come to quickly and now he was in complete surrender. 

She continued, “I would say that that is pathetic, but having seen your closet, I think it’s the best you can do. Am I right, little man…or is little girl a better fit? There is a lot of pink in there?” His sniffles didn’t provide the answer she wanted so she pressed, “Answer me-is it little man, or little girl? I see a man in wet pants and closet full of pink baby clothes so I think I have a good idea, but why don’t you tell me?” Her warm breath on the back of his neck seemed not to have a warming effect, he found himself croaking out her answer-“Little girl.” A few fresh tears followed.

The apartment manager he knew and had had a business relationship with for over a year, would never be that again. That relationship was now gone and in its place was something, he feared, at that moment, approached ownership. She took his shoulders and turned him around, he still held the bottle, but held it near his pants, a fruitless effort to hide the shame of his now soaked jeans. She likewise noticed the jeans and looking at him straight on, but eyes tilted as one might a child being scolded, “I think you may have dressed a bit above your abilities today, shouldn’t you be wearing something…more absorbent”.  He simply looked at the floor.

As she guided him into the bedroom, he couldn’t help but notice that she had laid out his pink training panties and baby print top. The implication was obvious-PUT THEM ON. She stopped short of saying it however, adding, “I think I may have been optimistic in choosing your outfit, you don’t seem ready for those.” She had picked up the training panties as she spoke and placed them back in the drawer and retrieving instead a disposable, pull-up diaper and plastic pants, carefully assembling those on the bed. It was a short instruction-“wipe yourself up, put all this on and…crawl, into the living room and we will talk about how this is to proceed.” Again, the lilting tone did little to soften the bite of her command. She took the bottle, turned and exited the room.

When he crawled into the living area, she was seated in the chair, his chair, had taken off her shoes, poured a glass of wine for herself. She looked down at him and noticed the tingle that was now a throb, quickened. She was so enjoying the power she held over this now reduced man that it made her wonder if she might orgasm just from the sight of it. She held the bottle out for him, again with the admonition, “…both hands”. He took the bottle, and looking up from his position on the floor, he wasn’t sure he wasn’t enjoying this. He had never bothered to conjure up that this could ever happen-it doesn’t happen-only in bad fiction does this happen. The adult thought he was having at that moment was stopped in its tracks when she spoke. She spoke as one might to a small child, small words, and soft voice

“You’re not much of a man, are you? I didn’t see any sign a woman might visit here regularly and I can see why now. You look completely natural sitting on the floor in a diaper with a bottle. Is this natural for you?” Truth was, he did just this, quite alone and unsupervised, several times a month-it was natural. Hearing it from a woman, a woman now squarely in control, didn’t seem comforting though. It was a like the heel of the shoe she wasn’t wearing was being pushed, hard, into a thigh. His failure to answer, along with his red eyes and tear stained cheeks would have sufficed most as a suitable answer to that question; she wanted to hear him to say it, even though it seemed a cruelty. She was not, by nature, a cruel woman, but this was a new and different thing.

“Well? Is it natural? Or do feel as pathetic as you look at this moment?”

He was conflicted. He did feel pathetic; and it was natural. A long explanation didn’t seem to fit the situation so he quietly answered only, “Yes, ma’am.”

She took a sip of wine, regarded her prisoner. He had given up without a whimper. At any point he could have demanded she leave, she had no right to be there and the simple presence of a fetish items wouldn’t ever have sustained serious police attention. His apparent effortless surrender seemed at odds with what the surroundings would have indicated was a fairly “squared away” man. She was now curious not only about his things, but about him.

“Tell me-how does a grown man fall to such a place? Tell me, and don’t leave anything out.”
Title: Re: Once Upon a Time....
Post by: sissykimmy1 on August 15, 2018, 04:05:33 AM
Hi! Loving it so far.  This is a very original approach.  I like the kinda forced but kind of wants to thing when it comes to grabbing someone out of their fantasy and into reality because I dream somebody might do it to me someday. :P
Title: Re: Once Upon a Time....
Post by: krystalasbaby2017 on August 15, 2018, 07:23:33 AM
good story love the humiliation of being found out.
Title: Re: Once Upon a Time....
Post by: cutebutt on August 15, 2018, 11:12:20 AM
Great new story. Love it when a pathetic little man is dominated by a superior woman.
Hopefully she will continue to humiliate him with
diaper changes, breastfeeding and exposing his tiny pen-is to her girl friends.
Title: Re: Once Upon a Time....
Post by: rt76209 on August 15, 2018, 12:53:46 PM
Chapter 3

Theodore Simpson was not at all extraordinary. Nothing about him stood out. He was the very paradigm of normal. He grew up, went to school, got good grades. Graduated college with a specialized degree in accounting, Theodore was a tax wiz. He worked for a large bank in the regulatory compliance department and though he was one of a handful of “go-to” people in the department in certain matters, he was almost completely anonymous. Always pleasant. Always knowledgeable and happy to help. Completely forgettable.


For as long as Theodore could remember he had been attracted to stronger personalities. Growing up, the more assertive neighbor boys found him a reliable, and pliable, ally and play mate.  He hadn’t been attracted to most girls since they tended to be flighty (to his mind) and he was far too shy to approach them, a trait that followed him into adulthood.  There were a couple of girls that would share their time with him, if only to be the beneficiary of a generous allowance he received weekly. His parents, both highly accomplished (his mother was college professor and his father a highly regarded researcher),   were able to provide a bit more than some other parents and Theodore was genuinely helpful around the house.  He had the feeling he was being used by girls at times, but he was able to set that aside, considered it a cost of having even that much of their attention. His fortune with girls never improved.


He seemed to internalize the submissiveness early on in his life. It created in him not only his satisfaction with serving all he met with his usual competence without regard of recognition, but also a sense that even the attention derived from the mild (and sometimes not so mild) abuse he suffered at the hands of those with whom he associated was deserved in some way. This created the perfect space in his soul for the woman he later married. He had graduated and was immediately hired to a good job. And, almost as immediately, he was married-to the first woman who had ever let him touch a breast. That was all it took, with that one touch she had overtaken his will. His malleable nature did not serve him well. His parents warned him, but to no avail. Shortly after the marriage the abuse began, the excessive spending, the drinking, but she let him touch her from time to time and that was enough. His sexual frustration (she had none, being as she was attending to that in other places and with other people) kept him faithful and puppy dog loyal, so long as he got to taste a breast from time to time.

It did finally sink in that his marriage was probably not well formed. He did a very Theodore thing with that feeling-he let it make more submissive. He tried to find secret ways to imagine himself more dependent, more submissive to his shrew of a wife. He began to imagine himself as her child. Doing chores became a cheerful again as he imagined he was pleasing a parent. She, not frequently, took notice-which drove him on even more. He began to imagine himself an even younger child, and her his doting mother. There was nothing doting or maternal about her, but Theodore wasn’t dealing in reality here. He was coping.

He came to view himself as almost a toddler age child, anxious to please a not very attentive parent who only occasionally offered any sort of reward. His wife had early on figured out that letting him suc-kle from time to time kept him docile, as if Theodore could ever have been anything else.  Sometimes the suc-kling included her rubbing him through his pants and he came to associate wet underwear with the end-all-be-all of pleasure. He would do it himself from time to time, but he felt awkward doing so. 
It wasn’t that much of a step to start wetting his pants from time to time. His wife never did laundry so she wouldn’t ever find out. It was a bit more of a step to buy the first package of diapers and an absolute act of rebellion to clear out the corner of a lightly used closet to hide them. He was a meticulous person, being discovered was a thing he just knew would never happen.

And, he did avoid being discovered. So much so that he grew his collection by adding other clothing items, some he could wear while at work, under his regular clothes. He even did so, very discreetly, when his wife was home, it added to the delusion of his being her dutiful child.  But, all deception fails.

After a four years of a horrible marriage they divorced. They were not rich, and by his nature he wasn’t going to argue with a property settlement that favored her. She walked away with much of his savings and the deed to the house, which he had been dutifully paying extra mortgage payments on-it would be all hers in just a few years. He was left with his personal items, some of his savings, and an impressive collection of juvenile and infantile clothing, which his wife had found as she was clearing a closet to hide her secret wardrobe of lingerie, worn for other men. Her collection no longer fit its previous hiding place. She would have kept him around, but one of the others made more money.

After the divorce, still very gainfully employed, he found his way to a quiet apartment complex, not far from his office. The very apartment where he now kneeled before the apartment manager, wearing a diaper, a juvenile print shirt with snaps on the shoulder, and holding a bottle.

Title: Re: Once Upon a Time....
Post by: rt76209 on August 15, 2018, 01:02:29 PM
A quick thank you for the kind words!  This is my first effort at this sort of thing so I am glad to have the feedback.
Title: Re: Once Upon a Time....
Post by: rt76209 on August 16, 2018, 11:37:46 AM
Short Chapter...more to follow, provided work doesn't impose...

She looked at him, there on the floor and the story he told had served to mitigate some of the feeling of power she had felt earlier. That power had been replaced by pity.  The manager had no children, her marriage had likewise been ill-formed and was peacefully concluded shortly after it had begun. That said, she almost wanted to call what she was beginning to feel, maternal. But mothers are powerful. As quickly as it had been mitigated, she began to see other avenues for this to travel.

An interesting tale….Mr Simpson.”  That name is hardly appropriate, given the current situation. Theodore isn’t quite right either, is it…Mr. Simpson?”

Theodore simply looked at the floor, not what she wanted so she sharply reiterated, “Is it?”
“No, ma’am.” It was all he could squeak out. She continued, in the lilting, but biting, tone, “What do you think we should call you? I certainly can’t call what sits here in front of me a ‘man’ so perhaps something more…feminine? What do you think Teddy?”

He simply looked at her, again with smallish tear set to drop. Sensing that there was little left to defeat, she did not require his further participation, “I think I will change the name on your lease to Theodora Simpson. And we can call you call you Teddy for short.”

The tear dropped. She, again, continued without his taking part, “I can see that you like it. I’ll make the changes.” 

At about 6pm, the manager of his apartment had entered his apartment. It was now 6:40pm. In the span of only 40 minutes, his life and his name, at least to her, had changed. Forever he feared. At least until his lease expired.  His complete surrender and re-subjugation had taken less than an hour.

“Well…Teddy; I’ ve to go home and see to some things, but I think I’d like to check back in on you tonight, after you’ve wet that diaper. I’ll come and supervise your changing your diaper.” She stood and walked to the counter to retrieve his phone, and using his phone dialed her number.

“When you’ve wet your diaper, you will call me and…I think since babies cry when they have wet diapers, maybe you should be crying when you call.” She placed the phone on the counter, looking down at the pitiful man on the floor, a slight smile creeping across her face. “Yea, you need to be crying when you call me. I have a key, I’ll let myself in.”

The feeling of power had returned. Still a little maternal, but powerful.
Title: Re: Once Upon a Time....
Post by: wailer on November 09, 2018, 07:13:26 AM
This is a very very very good story...
Title: Re: Once Upon a Time....
Post by: Sissieann on November 09, 2018, 01:25:27 PM
 ;) What a great start more please Kevin???  8)
Title: Re: Once Upon a Time....
Post by: wailer on November 10, 2018, 05:25:38 AM
oh my goodness, I live on my own in my apartment, if my landlady did an inspection I think I'd be in a similar predicament, and possibly with a very sore bottom for having it so messy. I wonder whether Teddy will have to become a maid in her nappies as well as a naughty little sissy?
Title: Re: Once Upon a Time....
Post by: sweet baby katie on November 11, 2018, 08:57:18 AM
Well written, creative and shows an understanding of the (universal) desire to have “the secret” involuntarily discovered and accepted.  Thank you.