“Jimmy! Your babysitter’s here!”
I heard the familiar words from my Mommy–actually, my wife of three years–who was busy getting ready for her date in the other room. I was in my nursery, sitting on the floor, where I’d been told to wait for my babysitter’s arrival.
It still drove me crazy with jealousy to see Denise getting ready for a date with another man, dressing in her sexiest clothing, while I was destined to spend another long, lonely night in my crib. The unfairness of it grated on me constantly and not for the first time did I strongly resent our unequal relationship. On evenings such as this, I was inclined to put up a fuss and be a pest with her, so increasingly, she had relied on the services of Auntie Brigitte, our current babysitter to keep me out of her hair.
I saw the door to my nursery was soon being pushed open and Auntie Brigitte towering over me as she looked down upon me.
“And how’s mommy’s little girl?” she asked solicitously, although her tone of voice couldn’t mask her amusement.
Auntie Brigitte was a distant French relative of my wife. Despite my age, Auntie Brigitte treated me like a four year-old child and Denise had given her the task of babysitting me when she was too busy to put up with me herself.
Auntie Brigitte had taken to the job like a fish to water, enjoying her power over me and Denise had given her full authority to discipline me as needed. And despite the fact she’d been babysitting me for over a year, I still burned with humiliation whenever she came over and saw me dressed as I was.
It certainly wasn’t helped by my wife’s choice of attire for me. I was wearing a frilly pink gingham Sunday dress, anklets, and glossy black Mary Janes looking little different from a precocious toddler girl.
It looked like Auntie Brigitte had just left from work as she was wearing a no nonsense business suit and her hair was tied back in a pony tail.
“What a pretty dress you have on, Jimmy,” she exclaimed as she came over and felt the eyelet lace trimming the short hem, “Is that a new one?”
“Uh-huh,” I mumbled as I blushed with renewed embarrassment.
My wife had made it clear to me when we got married that she would be the one in charge and even gone to the extent of making me sign a prenuptial agreement/contract which established our very different roles. Basically, I was to do as she told me, whenever she told me, and without question. I had been so awed with her incredible beauty and statuesque body that I was willing to agree to anything, so long as it meant living with her. What I hadn’t counted on was her plans to gradually feminize me and lower my effective age to that of a pre-schooler.
Our first argument had ended badly for me.
She’d settled it by yanking me over her lap and giving me a blistering spanking with her wide backed hairbrush, reducing me to tears in just a matter of moments. Not satisfied with my childish display of defeat, she continued to soundly paddle me, driving home her absolute authority over me and forever relegating me to secondary status.
After that, she gradually threw out all my underwear, replacing them with lacy panties and putting me in girly dresses to wear around the house.
But it was when she caught me masturbating that things took a turn for the worse. After another painful and humiliating spanking (this time in front of my Mother-in-Law), she produced a chastity device that she locked around my shriveled penis. She had never been happy with my equipment down there and this was just another way for her to take control over me.
Initially, she was allowing me to cum once a week but that soon turned into increasingly longer stretches between my moments of (brief) relief. One week turned into two, and before long, I was only getting unlocked once a month to get a perfunctory, impersonal handjob before she locked my little wiener back into its restrictive, plastic prison.
We had only been married four months when she happily brought home her latest purchase, a stout wooden paddle with numerous “air holes” drilled in the face for extra sting. Even though I had been on my best behavior that day, she still insisted on “breaking it in” upon my pantied bottom. I was sobbing like a baby by the time she finished, and since that first day, I’ve felt it’s sting many times, often, for only the slightest of reasons.
It was not long after that, that Denise hired some workers to come in and redecorate our spare room as a baby’s nursery. A large, oversized crib dominated the room and the walls were papered with pink cartoon characters. This became my room and I was told the master bedroom was now off limits to me.
Soon, Denise began seeing other men and she made no secret of her weekly liaisons. Her mother fully approved of her plans and she would often come over to babysit me, happy to treat me like an infant and it was her idea to change my bedtimes to 7:30 every night. I knew better than to argue with her since she had shown no hesitation in blistering my bottom with Denise’s paddle. It was also her idea to extend my monthly chastity sentence to three months at a time. She assured her daughter that a big sissy like me didn’t need to cum any more than four times a year and Denise quickly agreed.
“Okay let’s put away your coloring book, Jimmy, it’s time to get you ready for beddie-bye now,” Auntie Brigitte said as she summarily closed the page I had been drawing on and began putting away my crayons without waiting for my approval.
“Aw, is it time already?” I whined miserably. I couldn’t believe it was already after seven but since my nursery had no clocks in it, I never had any way of knowing what time it was.
“Yes it is, Sissy, its time to get you changed and ready for bed,” she explained in her motherly tone, “Let’s get that dress off and then it’ll be be time for nite-nite.
I pouted as she pulled the frilly ensemble over my head and outstretched arms before hanging it up in the closet. She returned almost immediately with a pink and white fuzzy fleece diaper shirt, decorated with a Disney Princess theme. No sooner was it pulled into place than she presented me with my nightly bottle.
“Here you are Jimmy, drink up your num-nums,” she sang merrily.
I accepted the 32 ounce baby bottle with blocks and giraffes and reluctantly began nursing the warmed milk. I had begun to suspect it was laced with a mild sedative and diuretic to better control me and it wasn’t for nothing that my crib mattress had a waterproof sheet covering it.
Taking my hand, she led me over to the changing table, a low, padded and vinyl covered surface six inches above the floor to sit me down upon.
“I see your mommy has begun putting plastic panties over your trainers during the day,” Auntie Brigitte observed with a trace of surprise in her voice, “Are you wetting during the daytime too, now?”
Her pointed question made me blush furiously but she seemed oblivious to my discomfort.
“I…um, had an accident, the other day,” I mumbled as I stared down at the pink carpeted floor, unable to look into her pretty green eyes.
“Well, I’m not surprised,” she said casually, “A big sissy like you really should be in diapers all the time–not just for bedtimes. I’ll bet Denise will be making a few changes around here before too long.”
I winced inwardly at the idea of losing my last connection to adulthood, however pathetic it was.
“Please-please don’t tell her to do that,” I pleaded with her.
“Everyone knows what a bedwetter you are. If you can’t keep your trainers dry during the day, she’ll have no other choice,” she quipped.
“Now drink up Sissy,” she insisted as she put the bottle back to my lips, effectively ending our conversation, “we don’t have all night.”
I pouted helplessly as Auntie Brigitte snaked my yellow plastic panties down from my thick cotton training pants and put them aside for later use.
“Still dry for now,” she mused aloud, “Oh well, not for long.”
Down came my trainers, exposing my bald, shaved crotch and my embarrassingly minuscule penis, securely locked within its CB6000s chastity device.
Auntie Brigitte giggled as she looked down at my caged member, incapable of growing past the frustrating inch and a half limitation of its tube.
“You didn’t really think you were going to be able to satisfy Denise with this, did you?” she asked as she held my tiny package in the palm of her slim hand and gently squeezed my swollen balls.
Not sure if her question was meant rhetorically, I shrugged lamely and continued nursing from my bottle while my cheeks burned with shame.
“This is so small, it’s of no good to anyone…I think its just as well she decided to lock it up.
“How long has it been now, since you last came?” she asked as she began gathering the thick cotton diapers next to her.
“Um…two months,” I said in barely a whisper.
“Well, only one more month to go, Sissy. That shouldn’t be any problem,” she said with confidence she couldn’t possibly feel. More likely, she just didn’t care.
“No…this is where you belong,” she said as she slid a tall but soft stack of pre-formed diapers under my raised rump, “Securely pinned into a thick, thirsty set of baby diapers with some snug plastic panties to keep your childish wetting under control.”
I wanted to get up and run from the room but I was forced to sit there and endure her humiliating comments.
“Just take a look at these,” she said brightly as she held up a fluffy white diaper, “So soft and comfy, with a nice soaker strip sewn through the middle for heavy wetters like you.”
Just then, Denise strolled into the room unannounced, looking as if she were almost ready to leave.
“Hi Auntie Brigitte, how’s it coming in here?” she asked, completely ignoring me.
“Just changing the sissy into his diapers for the night,” she replied with crisp efficiency.
Looking over the top of my upraised bottle, I drank in the awe-inspiring sight of my wife, framed within the doorway. She hadn’t yet put on her dress and her fabulous body was impossible to ignore. Her tall, five inch stiletto heels lent her a commanding presence and her skimpy black thong intimated at what she had planned for later on. She certainly had never worn underthings like that when we were first dating, I reflected with gloominess.
Her tremendously big breasts were pushed up in the ultimate display of femininity, mocking me with their soft curves and deep, sexy cleavage. Only once had she ever deigned to let me touch them but that was three years ago and it seemed like an eternity now.
I felt my penis struggling to become hard within my chastity device, only to be brought to a quick and effective stop by the short confines of the tube. I bit back the groan on my lips but my heart was thumping within my chest. I was so horny I couldn’t even think straight and these two babes were totally unaware of my need.
Looking down on me with an enchanting smile on her face, I could plainly see Denise was excited about her date. It was equally clear she was pleased to see me under control–out of her hair, being put into my sissy diapers and readied for bed like an incontinent toddler.
Denise turned on her heel and I was briefly treated to one momentary view of her delicious derriere as she returned to her bedroom.
“Your mommy seems very happy with her new boyfriend,” Auntie Brigitte said as she drew one side of my diapers up and pinned it to the other corner at my hips, “I think this is date number three.”
My spirits sank as I imagined her having wild, passionate sex with some strange man while I was confined to my nursery.
“Don’t look so grumpy, Jimmy,” she chided me as she drew up the other side and pinned it in place, “You should be happy for her that she’s found a man that can finally satisfy her–we both know you were never going to be able to do that.”
My eyes moistened with tears and I looked away, too ashamed to look my pretty babysitter in the face.
Taking a pair of shiny white nursery print waterproof panties, she shook them out with a flourish as she held them up before me.
“What do you think, Jimmy? Do you think these will look fashionable with your Disney Princess top?”
I squirmed with embarrassment as she smiled down on me in anticipation.
“Or would you prefer these cute pink panties with the lace?” she asked as she briefly picked up a polka dot pair of vinyl panties with white lace around the legs and waist.
“Personally, I like the white nursery print so I think that’s just what we’ll dress you in tonight,” she told me without waiting for an answer, “And anyway, it’s not like you’ll be showing off for anyone tonight in your crib. These plastic panties are good because they have nice snug elastic around the legs and waist –that’s an important feature for bedwetting sissies like you.”
Gathering them together in her hands, she began snaking them up my skinny, hairless legs. With some effort, she worked them around the considerable bulk of my diapers, ensuring that none of the soft cloth was exposed outside the elasticized seams.
“There you are, Babykins,” she said brightly, “All safe and secure now in your sissy panties. That should keep your crib dry.”
I whimpered and fidgeted, fussily nursing my milk as she made a few adjustments and checked around my waist. I hated wearing diapers and plastic pants but like everything else in this house–I had absolutely no say in the matter.
After briefly powdering between my legs, she patted the thick, shiny smooth face of my crotch with satisfaction.
“All ready for beddie-bye!” she announced, “Come on–hurry up and finish your bottle, it’s time to brush your teeth and then it’s into your crib for the night.”
I gulped the last of the tepid milk and I could already feel the drowsiness beginning to wash over me. Soon, I reflected miserably, I would be asleep in my crib, helplessly wetting my diapers while my wife was being ravished by some other man.
Awkwardly, I stood up and waddled toward the door, my bulky diaper preventing me from completely putting my legs together. Auntie Brigitte followed me out, slapping the thick seat of my diapers as a way of hurrying me to my task before going to meet Denise in the bedroom.
Dutifully, I did my business, wishing I could make use of the toilet like an adult before returning to the nursery. But I was only allowed to brush my teeth and I knew Auntie Brigitte would be impatiently waiting for me when I finished. I knew from experience that pulling my diapers down or fiddling with them in any way was grounds for a spanking so it wasn’t worth the risk.
A few minutes later, I waddled back to the nursery to see her talking with her boyfriend on the phone.
“Hey–gotta go,” she told him when she looked up to see me in the doorway, “But I’ll see you soon, I’ve just got to tuck the baby in.”
I also hated having to go to bed so early when everyone else’s evenings were just beginning.
“Can’t I stay up a little longer?” I begged her.
“Sorry Sissy–Mommy’s orders. You’re to be in your crib no later than 7:30,” she said as she glanced down at her watch, “Looks like we’re about 20 minutes early tonight but that’ll be just fine.”
“But–” I pouted crankily, “It’s not even bedtime yet.”
I stamped my feet in protest at her apparent indifference.
Auntie Brigitte scooped up the big pink rubber pacifier on the dresser and brought it over, pushing it against my lips.
“Open up for your paci, baby,” she said in a sing-song voice, ignoring my point completely.
“Uh-uh,” I refused petulantly, angrily pursing my lips together.
“Now Jimmy, you can either go to bed with–or without–a hot, stinging bottom. What’s it going to be?” she said in a firm, demanding voice.
Balling my fists together in frustration, I hesitated, but only briefly. Auntie Brigitte had no qualms about putting me over her lap to teach me a lesson as I’d already learned the hard way previously. Acknowledging her superiority, I obediently opened my lips and she pushed the thick rubber nipple into my mouth, ended the discussion once and for all. My cheeks reddened with humiliation at being defeated by this young hottie but I let her remove my Mary Janes before guiding me to the open side of the crib. She pulled back the soft pink coverlet and as I crawled in, I heard the waterproof vinyl mattress cover crinkle audibly beneath my weight, a sound all too familiar to a bedwetter. She pulled up the blankets and handed my teddy bear to me, tucking it in under my arm.
“That’s a good baby,” she said, once more in her pleasant mood. Reaching down, she kissed me on the cheek briefly and I inhaled her wonderful perfume. This one fleeting kiss was as close I got to having any kind of sex and I savored the instant, wishing somehow to make it linger.
But Auntie Brigitte was already closing the side of the crib, latching it in place before she turned and made for the door.
“Nighty-nite, Jimmy,” she said as she gently closed the door behind her.
After the door closed, the lights went out and the nursery became dark, save for the dim light put out by my Dumbo nightlight on the far wall. Denise had designed it that way so that the lighting could only be controlled from outside of the nursery. The door was also only lockable from the outside and I heard Auntie Brigitte gently turning the knob to make sure I was secure for the night. It would be another twelve hours before someone came in to check on me and by then, my diapers would be thoroughly and completely soaked.
In my utter frustration, I was tempted to spit out the pacifier and let loose with a string of colorful curse words but even with that, I knew better. A baby monitor stood on the dresser top, a permanent way for Denise or Auntie Brigitte to listen in on my nursery activities when I wasn’t being supervised. Among my other restrictions, I was forbidden to swear and it wasn’t worth a spanking and mouthsoaping just for a few words said in haste.
Except for the crinkling and rustling of my plastic panties and the mattress cover, the
room was quiet, and I tried to listen to see what was going on in the rest of the house. Denise was saying something to Auntie Brigitte; I heard the two of them giggle at something, and before long, I heard her heels clicking followed by the front door closing. A moment later, I heard the sound of her Lexus pulling out of the driveway and fading away down the street.
Without realizing it, I suddenly felt a slight warm wetness seeping between my legs and a trickle of pee flowing against my skin. With a panicked gulp and a cry of despair, I managed to shut off the flow but the damage was already done. Now I’d have to try and go to sleep with a distracting wet spot in my diaper.
It was going to be a very long night.
I do love a good sissy training tale :)
“Please what Nick? Or is it Jessica right now?”
“God. Please…I need….to cum.”
Ms Brigitte laughed, softly at first, and then louder, knowing what that would do to him. It excited him almost as much as it did when she called him names. Names like Jessica.
“Right now? Does my little slut Jessica need to cum right….this….instant?”
“Please…please. Now…and…I just…I need to cum MORE.”
Now she REALLY laughed. She knew this was coming (and she laughed at her own pun), but just hearing that from Nick’s lips, from his painted red lips…it filled her with a warmth that she savored.
“What ever do you mean, sweetie?”
“I…I…I’m just all tense and frustrated all the time. I just can’t concentrate. Please, can I PLEASE cum more often?”
“Ooooh. That is a VERY big request for a sweet little girl. But you know I do love when you ask me things. That pleases me very much.”
“Please…PLEASE. I just need to cum more often. Please. Will you please let me?”
“Hmmm. I suppose we could work something out. And I’m even feeling generous. What if I even offered to let you wear boxers again?”
Nick blushed visibly. “For real?”
“Yes Nick…I mean Jessica.” Did he just blush even harder? It was so freaking delicious.
“What do I need to do? Please…PLEASE.”
It almost sounded like his voice was getting higher…this was intoxicating.
“Well Jessica…I have been thinking. You’ve been pretty good whenever you’re my sweet little girl. And you’ve been learning do to SUCH slutty things when I make you be my whore….but…well..there’s a difference between learning…and training, isn’t there?”
He couldn’t answer. It was too much. Just too much.
She went on. “You see Jessica, I’ve been thinking. You wear panties for me every day. You are…used to it. But I don’t want that. I want you to CRAVE it.”
“Actually Jessica – I want you to crave more than that.”
“So…here is what I am going to offer you. You can cum…any time you want. And I mean that – you can spend all day in your princess bed and just touch your little clitty all day long if you want, and I KNOW you want to.”
Nick/Jessica couldn’t hide it. He blushed…but nodded.
Ms Brigitte smiled. He was too precious. “You can cum any time you want. BUT…and pay attention to this – you will ONLY cum if you are wearing panties.”
She wasn’t finished. “Panties…and heels.”
“I…I don’t understand.”
“What’s to understand sweetness? You can cum every time your little heart desires, but you will put on clean panties…and pretty shoes, before you do.”
“I….I can do that,” Nick stammered.
“Shhh….shhh….hold on. It’s very important for me that you understand this. And that’s because I want to enjoy this gift you’re about to give me as much as possible.”
She stroked his face. “Oh yes. Because you’re going to agree to this. We both know you are. But you’re going to agree to it with full knowledge and acceptance of what you’re doing.”
“You see…Jessica. I am going to train you. I am going to train you to YEARN to wear panties. I am going to train you that every time those sissy panties touch your little clit, and every time you walk around in slutty heels that make your feet ache to deliciously….that you will feel pleasure.”
“I am going to TRAIN you to associate panties…and heels…with cumming. I am going to train you, so that every time you touch your little clit, you go further and further down that rabbit hole. You can fight it all you want, but we both know it will be inevitable. One day you will wake up, and you will simply want to wear panties and heels for me. And I am betting that day is very, very soon.”
“Put simply Jessica – I am training you to have a women’s shoe fetish. Among other things.”
“Three other parts to our little deal, before you go up to your little canopy bed. You can cum whenever you want, but after you do you will send me a picture of your pretty little feet in whatever heels you are wearing. And after you cum 10 times….I expect you to buy a new pair of heels. I cannot WAIT to see how big your shoe collection gets in the next 3 months.”
“Three months? Why 3 months?”
“Because, Jessica – in 3 months…you’ll only get to cum if you’re wearing panties and heels….and a skirt.”
I just love dressing up my sweetheart sissy girl, Jessica. Besides, the transformations that stick are the ones that start out subtly and work their way in.
Have you ever found yourself being transformed into a sissy through sexy lingerie and tease and denial?”
It could only have been about fifteen minutes, but she couldn’t check her watch as she had her hands on her head, facing the wall, outside the headmistress, Miss Brigitte’s, office. Fifteen minutes, but it felt like an eternity.
She had started out fourth in a line of miscreants, and now it was down to her. Two girls had already come and gone, dispatched from the office in varying states of distress. Now it was the turn of the third girl, Roberta Jamison, and she had been in there an age. Sissy Miranda was musing on why this might be when, suddenly, the heavy mahogany door of Miss Brigitte’s study swung open, and out stepped Roberta. ‘Your turn now,’ mumbled the girl to Sissy Miranda, ‘she wants you in straightaway.’ Sissy Miranda turned round, managing to raise a brief half-smile to her tear-stained fellow, before knocking on the dreaded door herself.
Miss Brigitte was sitting behind her desk, a fine, crook-handled cane prominently on display before her. This was a weapon Sissy Miranda had become familiar with over the past few years – that and, of course, the strap. She did not know which she hated the most, but having tasted the bite of both, she was at least prepared for their sting: Miss Brigitte couldn’t really hurt her.
‘Well Sissy Miranda, I haven’t seen you in my office for a while,’ began Miss Brigitte. Sissy Miranda remained silent.
‘I assume you have a note?’ continued Miss Brigitte.
Sissy Miranda stepped forward and held out the note she had placed in the top pocket of her blazer.
‘Cat still got you tongue I see,’ went on the Head, as she picked up her glasses and read through the missive.
Sissy Miranda said nothing.
‘Well, this sounds like a very childish offence,’ asserted Miss Brigitte at last, surveying the tall fifth-former before her.
‘Go and fetch me that chair,’ she suddenly instructed, indicating a low wooden chair near the window, ‘and put it in front of the desk.’
Sissy Miranda didn’t move.
‘Do it, right now!’ commanded the Head.
Sissy Miranda’s feet obeyed, despite her mind reeling in confusion: this was not how she took the cane, or the strap for that matter.
Miss Brigitte stood up, waited for the chair to be settled, then sat down.
‘Come here and bend over my lap.’
Again, Sissy Miranda didn’t move.
‘Come here at once,’ continued Miss Brigitte, her voice rising to a crescendo, ‘or I will spank you harder and longer.’
Spank? Sissy Miranda was horrified: she had never been spanked before; never had to lie across the lap of the head mistress – this was too much.
‘Come here!’ ordered Miss Brigitte, and this time the girl did move, approaching the Head and then lowering herself carefully over her lap as indicated.
Before she could do anything else, Miss Brigitte had pulled back her skirt, pulled down her pink frilly panties and slammed her hand down hard on her behind.
‘Ow…ouch!’ issued from Sissy Miranda’s lips in shock, as another blow, and another rained down.
‘Be quiet!’ ordered Miss Brigitte, Sissy Miranda gritting her teeth as the blows increased in intensity; ‘This is not your place to speak!’