Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Recent Inactive Sissy Stories => Topic started by: Hello24; on April 16, 2021, 04:37:18 PM
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My first try at a story. Let me know if anyone enjoys it. Will continue with it for a while.
With the sun shining, and temperatures rising, it was quite a beautiful May morning. Almost any teenager would be ecstatic for weather like this, almost. Sixteen year old Junior just happened to be that exception. He sat in the back seat of the gray Rav 4 hopelessly staring out the window. Imagining how he’d spend this seemingly perfect day, all the fun he should be having. Junior was quickly brought back to reality though as the music was turned louder, and he wasn’t able to drown out the nursery rhymes any longer, in defeat he let out a heavy sigh. He’d scream, but he knew it wouldn’t do him any good.
After another 20 minutes or so of driving, the childish music finally turned down. As the car approached a red light the driver turned around to face Junior, “are you ready to see Nana today baby? I know she is super excited to babysit this weekend. She kept rambling on and on about it the other day”.
The pink pacifier in Juniors mouth did a wonderful job of hiding the smile so obviously had wanted to wear. Again he wanted to scream, run, to do anything, but didn’t. Knowing it was a rhetorical question, he just hung his head in shame. He just wanted the weekend to be over already.
The driver was Tara Williams, eighteen year old. She was a big girl for her age, slightly over six feet tall and nearly 200 pounds, whereas Junior was 5’6 and 130 pounds, she dwarfed him. It had been a month already Junior had been subjected to this ridiculous treatment. And for the last month, if Junior wasn’t at school or or sleeping at night during the week, he was at Tara’s house, being treated like a baby. On weekends, it’s expected he stays all weekend, as a baby, no exceptions. It doesn’t matter who else is around, or where they are. Tara had also set up a few play dates between her new big baby and her friends babies. To help Junior learn to be the best baby he could be. He absolutely hated his life the way it was. As The duo arrived at her mothers house terra killed the engine exclaiming, “we’re here”!
With a heavy heart, Junior sat still refined to the backseat as Tara gathered her purse and the large pink diaper bag, and exit the vehicle and made her was the the back door. Junior knew better than to open the door himself, and even if he had wanted to, the child lock was on. His door was opened Tara let out a quick giggle seeing her teenage baby. Strapped in the backseat wearing his depends, pink satin fingerless mittens, a pink Barbie shirt that was little tight on his tiny frame, and a cute purple hair band with a sunflower on it.
“Ok sweetie, give mama your hand so baby doesn’t fall when going into nanas house”, Tara said as if she was talking to an actual baby.
Junior didn’t comply quick enough, which was met with a swift slap to his bare inner thigh. Junior let out a slight whimper which was muffled by the pacifier in his mouth. In a flash he was out of the car. If it was possible his face could’ve been anymore red than it already was he couldn’t imagine. As much as Junior hated being treated like an infant he really hated when other people can see the way he was treated. It was so degrading. He always felt so naked and infantile in whatever outfit he was forced to wear for the day, as Tara always decided for him. He especially hated how when anyone would ask why Junior was dressed as such Tara took such delight in explaining how he’s a “special” baby and he’s slow and needs extra help.
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Great start dear i love his discomfort and i hope it gets worse please keep going
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Welcome, Hello 24! Your story shows much promise. I am gratified to find a new story with my favorite theme,i.e., a young, sissy boy who is subjected to diaper discipline with all that comes with it: forced regression back to the toddler, if not the infantile state, and the utter humiliation of having a collection of females of a variety of ages, including his own age or younger acting as both witnesses and participants. What confuses me at the outset of your story is your offering that the boy is sixteen, and the driver, who is allegedly his mom, is but two years older. Since your story is not too far along, I would like to suggest that you change the boy's age to twelve, the dawn of his adolescence when being regressed to babyhood can have such a profound effect. I also suggest that you change the relationship of the driver to the boy from mother to older sister, and describe her at age eighteen as being beautiful and sexy, just like her friends. Thank you, Hello 24, for offering what may turn out to be one of the best stories on this site in a long time. Thank you also for giving careful thought to my suggestions.
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I’m glad people are enjoying it. And also appreciate the advice as well.
I ended up changing the story right before I posted yesterday. And changed the drivers Taras backstory. She is not his mother, just a girl he had went to high school with. I will attempt to make it more clear in the next update. I also have been writing the story on my phones notepad. It definitely makes writing and editing the story more difficult.
But I have a lot written already, and plan to make it very, so long as people will enjoy it. I’m always open to criticism and ideas.
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Hello24,
I am enjoying the first chapter of your story.
I think it's a really good start, especially for a first effort.
I like to speculate what might happen next, but ultimately you are the author.
I'm looking forward to your next chapter.
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I am looking forward to read more, great start.
A sixteen years old going to playdates with real babies ... must be so humiliating.
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The big baby was anxious as Tara fumbled with the keys to the front door. Junior just wanted to be inside, away from all the peering eyes. As the door opened the two made their way inside the modest house. Tara closed the door behind Junior and wasted no time in reminding him that “babies crawl when no one is holding their hand, right sweetie? Now get down and follow me baby. Remember go up the stairs one at a time”. As she commanded, Junior got down on all fours, made his way to the stairs, sitting one one stair then the next. Just like you’d see any other toddler doing.
Slowly making his way upstairs, he couldn’t help but think back to how he even got into his current predicament. Just a month ago he was your average teenager, enjoying the end of his sophomore year. Juniors home life wasn’t so great. His father had left his mother sometime before he was even born. This really took a toll on his emotionally drained mother at the time. After Junior was born, his mother Sarah, started drinking heavily, something she’d continue to do even now. Junior learned from a young age that his mother never seemed to care about what he did as she wasn’t home much, she was out drinking with god knows who. He also had to learn to take care of himself early on in his life. But school use was a distraction from that, somewhat. Other than the fact he had to endure endless bullying from none other than Tara. She was the terror of the school, and she especially enjoyed picking on Junior, no, she loved it.
Tara as one of her cruel tricks created a fake dating profile and used the picture of a stunning woman she had found online. With the intention of making Junior believe he had a chance with this gorgeous girl, then revealing herself when the timing seemed right. She figured it would be a great way to humiliate him. As soon as she sent the first message Junior, who couldn’t believe this girl was messaging him, answered instantly and took the bait. Things started to progress between this fake lady and Junior, they quickly began to start talking dirty to one another. Tara laughing the entire time decided to ask her victim to send some exposing pictures. Like pictures of him j***king off, wearing a pair of his moms panties, him posed in a variety of poses, and more of the likes. Once Tara had realized what had happened, and the goldmine of blackmail she had just received, fell backwards on her bed wearing an evil grin.
On the first day of the last month before school was over, Tara decided it was time to act. She cornered the teenager at school, one day, and revealed everything and that she had every photo he sent this lady. Without giving Junior time to react, she simply said, “Now if you don’t want these photos and this conversation to be spread around the entire school. You’ll come over to my house right after school. Ok.”, and walked away. With little choice and panic setting in, Junior nervously did as he was told.
As he approached her house, which was only 4 houses down from his, his head was racing a million miles a minute. As he was going to knock on the front door. As he reached to knock on the front door, Tara opened it before his hand even connected. Pulling the nervous teen inside and locking the door behind him. Grabbing his hand she lead him to the living room, sat Junior on the couch and said, “I’m so glad you decided to come”!
“Tara listen can we just work this…”, Junior tried to get out before being cut off by his bully.
“Stop”, Tara commanded staring at the poor boy very intensely. “Do not interrupt me again please. So i’ve been thinking, what I want to do with you exactly. I mean look at these pictures”, she said as she glanced at her phone, swiping occasionally and giggling.
Juniors face went red, and he looked down in shame meekly replying, “no”.
“Good”, she replied, “so this is what going to happen, and this does not require a reply”. Her eyes had a very intense look. “As you know, I had my daughter about 6 months ago. What you don’t know is that my her dad took custody of the child. I only get to see her 1 weekend a month. Its awful, I miss her all the time. But anyway, I think it would be just so amazing if you played baby with me since she’s not here”, She gleamed.
Junior, now staring at Tara, mouth open in disbelief of what he just heard. He gave a weak attempt to stand and tried to protest. But Tara reach out, one hand pushing him back onto the couch, the other placed over his mouth to quiet him.
“I said I didn’t want you to answer baby”, she said firmly before continuing, “from now on until I say so you will be at my house whenever you can. I know for a fact you mom doesn’t care what you do. So realistically, if were not in school, I want you here. You can go home at night for bed time, but only on the weekdays! I want you here EVERY WEEKEND ALL WEEKEND. And I cannot wait for the summer when you can be here all the time”.
It was so much to take in, Junior didn’t know how to react. As he began to protest again, Tara again pushed him back onto the couch. She pulled her phone out displaying the picture of him in the panties, as a reminder. Junior went quiet and simmered down. Before he knew it, Tara had rammed a little pink pacifier with a butterfly on the end of it into his mouth. Her hand beginning to pull up his tshirt, she smiled widely, reached for Juniors shirt, saying, “Now if we’re playing baby, I think you need to be dressed just a little bit more appropriate”.
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Tara is so sadistic i want to know more about her bullying please keep going!
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Come on little miss, keep it moving please and thank you”, Tara snapped at the big baby. Causing Junior to snap out of his little day dream.
Upon reaching the top of the stairs, Junior immediately noticed the massive haul of baby gear Ms. Williams had gotten since the last time he was here. In the middle of the living room was a big old school wooden play pen. He looked at it extremely unamused, as he was promptly directed to crawl in the gate. Sitting inside the play pen, he noticed that the height of the crib only met just below his shoulders when he was sitting in It. It served no real purpose other than being another tool to humiliate and confine him. From within his temporary infantile prison, he had also noticed a slightly beat up pink, of course, baby play gym complete with the dangling colorful loud toys. Designed to keep a child entertained, he wasn’t happy about seeing it in the living room. Dolls, rattles, blocks and other baby toys were also littered amongst the room.
“Well I see Julianna found her new play pen I see”, smiled Taras mom, Brenda walked right up the the teenager and cupped his chin with her gigantic hands. If Taras size intimidated Junior, he wasn’t sure how to describe Brenda. She was taller than Tara by 5 or 6 inches. And where Tara was big because she was a heavy set girl, her mom couldn’t have been more opposite. She was in incredible shape for a woman her age. She use to be very competitive and active in her younger years. It clearly still showed.
Junior shuddered. He hated that name. He hated being referred to as “Julianna”. To him it was just another way for them to emasculate him. The new name was nanas idea. She had said she wanted “a sweeter name for her sweetness”. Tara only called him Julianna only when she was very angry at him. Which he was glad about simply for the fact he didn’t have to hear that awful name all the time.
Tara laughed while hugging her mother, “Yes she did. And look how adorable baby looks sitting in it. But listen, I don’t mean to be rude Mom, but I have to get going in. I have to get to the airport for the work trip. Oh and before I forget, I didn’t have time to feed this one the morning. So feed her when we please, no rush.”.
After the goodbye to her mom, Tara made her way over to the play pen and knelt down right in front of Junior, who just sat there silently staring at her while nervously suc-king on his pacifier.
“Now little one, mommas gotta run. But she’ll be back real soon ok sweetheart. Now You make sure you behave for Nana this weekend, ok honey. You know she’ll let me know if someone misbehaves”, she sternly said shooting Junior a very serious look. With that she quickly kissed him on his forehead and made her way to the door. Waving goodbye one last time.
“I’m so excited that I finally get to have you all for myself for a weekend! How exciting is that. We’re gonna have such a fantastic time. Does baby want Nana to feed her?”, Brenda said with a smirk on her face. Without getting a reply from Junior, she quickly made her way from the living room the the kitchen. Humming loud enough to be heard from the other room. She returned quickly with he hands filled with things. Which she placed right outside of the playpen. Then opened the gate on the play pen coaxing the big baby “come to nana baby you can do it, be a big girl”.
As he crawled out of the playpen he sat where Brenda had motioned for him to go. As soon as his diaper and bottom was flat on the ground again, Brenda picked up the oversize babies bib and fastened it around Juniors neck. “Well now doesn’t somebody look absolutely adorable”, Brenda exclaimed and began slightly ticketing juniors stomach, “ I could just about eat you up. Gosh. Absolutely precious”.
This was so awkward, Junior absolutely hated when they would tickle his stomach, or give him raspberries. It truly made him feel like he was nothing more than 6 month old. It also didn’t help that Junior was very ticklish. So he couldn’t help but laugh anytime his new Nana subjected him to this torture. He felt his inability to stop himself from laughing just made him look like he was really having fun and enjoying it. Which was far from the case. When she was finished having fun with the grown child in front her, she picked up the pink Disney princess bowl she had brought out earlier along with an infantile pink butterfly spoon. Mixing together the bland concoction she kept exaggerating how good the food looked and pretended to eat it. Just like a mother attempting to get her young fussy kid to eat.
“Ok Julianna show Nana how a big girl eats. I can’t wait for you to try this honey. It’s a new all organic brand. One of the ladies I work with had told me her granddaughter refuses to eat anything else”, was the last thing Brenda said before removing juniors pacifier & shoving a spoonful of the bland mush into His slightly opened mouth.
Though Junior has eaten his fair share of baby food this past month, most of which wasn’t very appetizing, he wasn’t prepared for the taste of what he was being fed. As soon as the first spoonful entered his mouth his tastebuds were screaming at him. His first instinct was to immediately spit out the terrible food. But Brenda was able to read his little face. As soon as he spit, Brenda had already brought the bib up to his mouth. Catching the food as not to waste any, also smearing some of the excess on The boys face.
“Bad baby, bad Julianna.”, Brenda said while angrily shaking her finger back and forth like she was scolding a child. She began scraping the remnants of food of the big white bib patronizingly saying, “you know the rules Julianna. Bay eats what and when it’s time. No if and or butts. Do you think mama would like to hear you’re misbehaving already little missy? Now open up, her comes the airplane”. She smiled as the her little one opened his mouth and reluctantly ate the morsels of food he had just tried to dispose off.
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Poor Junior i hope he puts up a fight such suspense.
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Brenda was beside herself. She honestly couldn’t remember the last time she was so happy. Probably not since Tara was a little girl herself. At first Brenda was a little skeptical about how this whole situation would play out. Though she quickly realized two thing; how much she truly missed taking care of a baby albeit even a baby like her Julianna, and how powerful she felt treating this teenager as nothing more than a helpless infant. On top of that she really enjoyed the fact her daughter seemed all around in a better mood lately.
As the spoon went into the bowl, Junior was relieved when Ms. Williams announced that baby did a good job and ate all of his food. His stomach still turning from the nastiness he just had to eat was only made worse when the nipple of a baby bottle was jammed in between his quivering lips. As soon as the liquid from the bottle hit his tongue, it sent a shiver down his spine. It was formula. Baby formula. He despised formula. He hated the taste. It was so odd, almost like a metallic taste, he’d never tasted anything like it before to compare it to. He was so sad he was thinking to himself, “I’m supposed to be having the best times of my life right now. Yet here I am dressed as a baby, a girl baby, being fed from a bottle from my new ‘nana’, what am I going to do”. Just as his thought ended he looked up and locked eyes with Ms. Williams and didn’t like the way she was grinning, not at all.
“Good job Julianna, you finished your bottle without a problem just like a big girl”, beamed Ms. Williams. She took the bottle out placing it on the ground, putting the hated pink pacifier back in place. Then started rhythmically rubbing his back and gently patting it. “Come on, burp for nana. Babies going to feel so much better after she burps”, Brenda repeated until she heard a modest burp which caused her to giggle, “good job sweetie, good job”.
Junior didn’t have to burp. He never had to after he was given a bottle. But he learned that making himself burp rather than not burping worked out better in his favor. As he wouldn’t get threatened or punish for not “acting his age”. He sat still and watched as the giant women took off his bib, gathered the childish bowl and empty bottle, then made her way out of the living room. Growing more nervous by the second thinking about what Taras mother had planned for him now.
A few minutes later Brenda returned to the living room holding a pink yoga mat, which was used as the babies changing mat. She knelt down next to Junior, unrolled it, and motion for him to crawl over and lay down. Which he did with no resistance.
“Ok miss I want to get you cleaned up, and smelling sweet. Babies nasty body hair is beginning to grow back a little, so we’ll take care of that as well so Mama doesn’t have to”, Brenda began saying as she began to pull down the depend. Once completely off, she smiled as the pink chastity device wasn’t being by concealed any longer. “I see baby still has her favorite little toy on, isn’t that just wonderful”, she said mockingly as she began examining the cage. She laughed to herself seeing how red and embarrassed this caused the baby to get. “Awe honey, it’s ok, baby doesn’t need to be upset. It’s just to make sure baby is behaving all the time. And it just looks so adorable”, she continued.
“This is all just a joke to them, to everyone but me”, Junior thought silently to himself, growing redder in the face, as this lady was proudly examining his locked up manhood. The cage was torture for the poor little sissy. Being a 16 year old, his testosterone was raging through his body, and he was quite literally always horny. Before Junior was locked up like this, he was playing with himself at least twice a day. So when Tara began the baby treatment, whenever he would get a diaper change, or whenever she gave him a bath, he would almost instantly get hard. Each time without fail, he was scolded and punished by Tara because “thats not something a baby or a little girl would ever do”. Luckily, on school nights when he was temporarily freed, he made up for the wasted erections.
That was until the second weekend Junior had to endure at his bully/neighbor/mommy’s house. He arrived that fateful Friday after school was over, knowing he’d have to play baby all weekend as was part of his new routine. Holding his head in shame as he approached the front door, opening it, and entering without knocking. As the door shut behind him, the poor boy sighed heavily before resigning himself onto all fours, slowly crawling towards the stairs.
“Well hello sweetie”, Tara eagerly said while unrolling the pink changing mat in the living room, “Do I have a special surprise for you my dear! Quickly baby, crawl to Mama, you can do it. Come on baby girl”.
Slowly, but surely crawling towards his mat, he tried to avoid looking at Tara. He really wanted to hide the fact he was so incredibly ashamed of himself, as he always was when he complied with her demands. Before Junior even laid down on the mat, Tara already started tugging the boys “adult clothes” off. Eventually leaving him laying stark naked and very vulnerable. As expected, Tara began to wipe the big babies p*nis, causing it to get hard.
Tara had a wicked grin, “Oh my baby girl likes getting her di-di put on, doesn’t she baby”?
She began wiping his p*nis faster, and with a firmer grip. Something that really shocked Junior, although he wasn’t complaining as this has yet to happen. It was amazing. As he opened his mouth to let out a big breath, his hated pink pacifier was lodged into his mouth.
“Shhhhh, baby needs to be quiet if baby wants to play”, Tara said in baby talk, while playing with the sissys member even faster, “be a good girl and show mommy how much fun you're having miss”.
While the hand job was amazing, the awkwardness of the entire situation made Junior feel strange. That he shouldn’t be enjoying this. That he should protest. But he couldn’t. Soon enough, he erupted in complete euphoria as he finally c*me. He sat there with his eyes closed, in pure bliss, and so relaxed. So much so, when he felt Tara grab a hold of his p*nis and put something around his balls, he didn’t pay much attention to it. Then she put something over his actual d*ck.
Click
Frantic, Junior tried to see what the hell was just put on his privates. But as he went to sit up, Tara shoved him right back to the ground. “What the f*ck”, he was screaming to himself. His eyes were open wide, and filled with fear.
“Thats none of babes concern anymore. Its just extra insurance that my little baby, stays and behaves as she should”, she said very firmly staring at Junior right in his watering eyes. “Now lets get you dressed for the day little missy”, she continued while sprinkling baby powder on the newly locked up toddler teenager.
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Could one of them use hypnosis to brainwash him into being a baby