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91
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on December 16, 2025, 01:11:06 PM »
Chapter 285.

She stopped in the doorway.  Lady Middiford had made herself a cup of coffee and was seated in an armchair.
“Well?  Are you coming in or not?”
Thomasina crept a few paces into the room, cheeks burning, eyes fixed on the floor.
“For goodness sake, Thomasina!  Stand up straight and look at me.  Yes, that’s better.  Well, well…  Whoever would of thought it?  My sweet little daughter.  It seems only yesterday you were begging me for frilly dresses.  Well, at least you still seem to like pink…”
“I’m sorry, mummy.  And actually I don’t like pink at all now…”
“Why are you apologising?”
“What?”
“What are you apologising for?”
“Well I know it wasn’t my idea, but I’m sorry I kept it on.  Really, it was just easier than taking it off, so I…”
“Thomasina, darling, do you think I’m disapproving?  Listen – I told you last birthday that I considered you an adult.  You’re old enough to date, to have sex, for heaven’s sake.  I wouldn’t dream of interfering in your private life or making judgements about your choices of anything – let alone something as trivial as clothing!  Anyway, you look great in that.  You must have caused quite a stir at Pitt’s Wood.”
“Y-you’re not angry…?”
“Course not, silly.  I’m not that narrow-minded.  And I have to tell you that the lady who made that for you seems to think you’d make a good model for some of her creations.”
“Really?”
“Yes.  And I can see why.  So I suggest you get yourself along there and see what else she’s got for you.”
“She wants me to model for her?”
“Well, she’s interested anyway.  If you have the nerve it’s up to you to make your pitch.  I have no objections.”
Thomasina was speechless for a moment.
“And Miss Poole seems to hold you in high regard, as a rider and as an individual.  Having met her, I would trust her judgement implicitly.”
“She does?”
“Yes.”
“Did she say anything else…about Sunday?”
Lady Middiford laughed.  “Only that Ponyboy probably ended up with a sore behind, and that you did your job well.  What more do you want?”
“Oh…no nothing…  I just wondered…”
Relief flooded over her.  Relief and excitement.  Modelling?  Modelling latex?  That would be so cool…so sexy…”
“If you think so too, mummy, I will make an appointment at Fantastex…  I owe that to Miss Poole…”
“Yes, I think you do.  Now shall we send out for some food?  It’s too late to cook.  If you want to stay as you are that’s fine by me.  Actually, it would be good practice for you to answer the door when the delivery guy arrives.  Yes?  It’ll be amusing to see his reaction…”

92
Active Sissy Stories
/ Re: His Aunt Nicole
« Last post by Simonssister on December 16, 2025, 12:50:06 PM »
Chapter 284.

That evening, after supper, Lady Middiford sat her daughter down at the table, gave her a glass of wine (to loosen her tongue), and confronted her.
“I met Miss Poole this afternoon.  She told me some very interesting things.  She told me about what happened at Pitt’s Wood on Sunday afternoon, for instance…”
Thomasina turned bright red.  How much had Miss Poole said?
“Oh…r-really…?”
“Yes, my dear.  I can see it through your shirt.  You’re still wearing it.  Bright pink.  Very fetching.  And I can smell the latex.  Did you really think I wouldn’t notice?”
“I…er…  Really. mummy, there’s hardly been time…”
“Well there’s plenty of time now.  Perhaps you’d like to explain…”
“Er…w-what did she say exactly…?”
“No.  I want to hear it from you.  Everything.  About you riding that Ponyboy, and then the pony rides.  But first I want you to take off your uniform and let me see what you look like in pink latex.”
“Mum…please…”
“No excuses.  You spent the whole of Sunday afternoon cavorting around in front of dozens of people.  So you can jolly well show your mother what they were all staring at!”
“But…”
“Now, Thomasina!”
There was no getting out of it.  She rose, blushing, and headed for her bedroom.
“And put your riding gear on.  I want to see exactly what my sweet innocent daughter looked like.  I’ve seen a photo already, so don’t try any tricks!”

In her bedroom she stripped off her school uniform, muttering under her breath.
“Shit, shit, shit…  Why is the thought of showing my mum a hundred times worse than showing all those strangers?”  But she knew the reason.  Exhibiting herself in front of all those people had been embarrassing but also exciting.  It had given her a real thrill, especially seeing the men staring open-mouthed.  After the ordeal at the Old House, when she walked out onto the top of the big field, at first she had wanted the ground to open and swallow her up, to use that exaggerated metaphor.  She felt naked.  She might as well have been naked, her body sheathed in fine, skintight latex, with every line and curve visible.  She could feel everyone’s gaze on her, she could see their delight as they ran their eyes over her, hear their suppressed exclamations, gasps of surprise, muffled giggles and whispered comments.  The women were just as bad as the men – no, worse!   She was terrified, trembling and tearful.  But as the minutes passed she felt herself, though still nervous, becoming increasingly aroused.  Out of the corner of her eye she could see the swell of her small breasts, the points of her nipples, which were hardening despite her efforts to stay composed.  The seam of the suit which ran between her legs was slightly raised on the inside and as she moved it insinuated itself deeper and deeper inside her.  Later she had discovered the inner flap on the crotch zip was trimmed with narrow latex piping, which served no apparent purpose other than to titillate the wearer.
But the feeling of being encased was so exciting she’d been loath to take it off.  Wearing it under her school uniform was a huge risk – she’d been obliged to wear a silk scarf on the pretence of having a sore throat in order to hide the top of the collar.  But it gave her such a thrill to sit in class wondering what her classmates’ reaction would be if they knew!  But she had also been finding it rather hard to concentrate.
“Thomasina?  What did I just say?”  Miss Townsend was her eagle-eyed English Literature teacher.
“Oh, er…  You were saying about, er…the metaphor of the…  I mean you were explaining why “With joy and grief, My heart is torn”…”
“Really?  Well I was, ten minutes ago.  We are now discussing the final stanza.  Please pay attention.”
“Sorry, miss…”
“Are you all right?  You look rather flushed.  Is your throat bothering you?”
“I’m fine, thank you, miss…  Sorry…”
A faint ripple of giggling.  Thomasina never normally got reprimanded.  She pulled herself together and tried to focus.  But all she could think about was that shiny red sausage bouncing up and down, and the feeling of Bobby’s spasms as she sat on him…

The feelings of sexual arousal, the thrill of being stared at and the sense of power that came with it, and now the risk of being discovered, all combined to give her a fantastic buzz, a sort of psychological high which, once experienced, was difficult to relinquish – hence her reluctance to take off the suit.  It was so different from anything she could have imagined a couple of days ago, she felt so different as a person, that she knew it was some sort of turning-point in her life.  But as she pulled on her riding boots in her bedroom all such pleasures had evaporated.  She was sure she was going to get a good scolding.  Did her mother know everything about her Ponyboy ride?  What if her lovely new catsuit was confiscated?  As she returned to the living-room she was trembling with anticipation…
93
Active Sissy Stories
/ Re: The Little Sisters of Gamma Delta
« Last post by Dancer4Fun on December 11, 2025, 02:11:51 PM »
So glad your  writing. I have missed the little sisters. Your writing is so descriptive it's almost like i am their watching the story unfold. Keep up the good work. Thank you.
94
Active Sissy Stories
/ Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on December 10, 2025, 06:56:16 PM »
Appreciate the nice comments BabyJay!  I have a lot of raw material for this story. Keep trying to organize it to make it more manageable and entertaining ;)  More soon...
95
Active Sissy Stories
/ Re: Peter was a petty criminal
« Last post by Howarth66 on December 10, 2025, 09:29:23 AM »
All of them brook down and cried knowing they had failed the task set by Lady Forrester and Judge Strickland as the two ladies returned to the room they were dressed differently almost as if they had expected the girls to fail, they were dressed in black rubber cat suits. Lady Forrester said right then it seems you have chosen to stay as girls so when we move to next room there will be lots of girly things to do very naughty but lots of fun. The girly boys look at each other they were not sure they would be having fun. As they entered the room it was like a ladies Victorian Parlor except all the girls were dress like Peter, Primrose, Mandy and Clare instantly the girls all became very horny they could not understand why but the blushed and went very coy. The ladies or the more mature women were dressed like Lady Forrester in black rubber catsuit with the added appendage of a strap on dil-do and when Peter turned around, he saw that Lady Forrester and the Judge had put a strap-on on. In a corner of the large room was a large play pen with very high playpen fence around eight foot high and next to it was a door name changing room, In the play pen was around a dozen girl all dress in very frilly dresses and diapers looking like toddler girls. There were also six girls dressed in shorts and t shirts but if you looked closely, they had padded knickers that look very much like training panties you give toddler that you are trying to potty train. The girls were carrying drink trays serving the women in rubber catsuits of the girl that were dress in sexy underwear. To one side of the room there was a row of stocks some empty some with the girls with crotchless knicker were secure by their wrists and neck all peter could see was their bottoms in the air showing their vagina and bum hole other girls in the stocks had no knickers just their bare bottom. In the centre of the room the was a mixture of girls in the same outfits as Peter but also there were girls in t shirts with diapers and clear plastic pants you could see the waist band of the plastic pants was secured by a gold lock and chain. Peter could see they were desperately trying to take off the plastic pants but they were very securely fixed. You could also clearly see which girl had accidents in the diapers as the clear plastic did not hide the yellow stain from peeing their nappies. Lady Forrester led Mandy and Primrose to the stocks they were place in the stocks their crotchless panty girdles were taken off and both Primroses bushy Vagina and Mandy’s bald one was in full view. Lady Forrester and Judge Strickland put their strap on dil-dos on. They then started to pump the two sissy girls with their stap Ons getting faster and faster Mandy and Primrose started to moan as Lady Forrester and Judge Strickland continued getting faster than Primrose and Mandy started to scream as they started to climax as they climaxed, they squirted vaginal c-um all over their legs.
The girls had a funny smile on them as if they had been hypnotised Lady Forrester released the girls but Mandy and Primrose made no attempt to put their knickers back on instead, they headed to the room marked changing room like mind-controlled robots. Thirty minutes later the two sissies returned very differently both were dress in short red with white trimmed sailor dresses the dresses had white yoke collar with lace trim. At the back of the collar a small heart shaped lock could be seen locking the dress on. Mandy and Primrose had thick white woolly pantyhose on with white lace socks and shiny black t bar Mary Janes which had a locking strap with a small pad lock. The hem of the dress came down so short that the girl’s cloth diapers and clear plastic knickers could be seen they were heavily diapered with what looked like a very thick cloth soaker pad   under the cloth diaper. They had traditional white leather reins on over the dresses the centre had a pink butterfly on the leather breast plate with their name in pink. They went over to lady Forrester and Judge Strickland shouting mummy and hugged them and kissed them as if Mandy and primrose were little girls.
Lady Forrester turned to Peter and Clare said it is your turn know Peter and Clare were led over to the stocks their head and hands were placed in them. Peter kept think I must not climax he felt his panty girdle knickers being taken down and saw Lady Forrester smell them and put them in her purse. Poor old Clare kept shouting please no please I will be a good girl but Judge Stickland just laughed and said you will be when I have finished with you as she put Clare knickers in her handbag. Peter felt a spray being used on her vagina and her Vagina started to tingle. Lady Forrester Strap on entered Peter all he could think of was if he had not failed the challenge he would know be a man again and Lady Forrest would have been having the payback. As Lady Forrester started a rhythmic up and down motion pumping Peter with her stap on Peter started to get aroused he tried to think of other things like he used to play rugby and football but as Lady Forrester continues it was getting harder to focus his clitoris started to tingle and he became more and more aroused and his vagina was starting to juice up his mind wondered to girly things thinking he would like to do cooking more ballet and equestrian riding just then he let out moan and started panting it was no good he shouted faster faster Lady Forrester obliged by know he was help with his bottom rhythmically going in synchro with Lady Forrester he was moaning then he let out a large scream as he climaxed. It happened in an instant his mind fogged over and had this urge to be treated as a little girl he had no fight in him. Lady Forrest released the stocks she looked at Peter and Clare they had the same funny little smile on their faces as Mandy and Primrose. They were led away to the changing room when they entered the room the two maids there stripped them so they stood there naked they were escorted to what looked like old style barber chairs placed in them and restrained by their wrist and ankles.  A short of old-fashioned hairdryer was place over their heads the maid explained that these were there to wipe their minds reintroduce mind of special girls. Girls with a mental disability of a mind of a two-year-old who are incontinent and wear special girls’ underwear or special diapers. The maids laughed you will remember as an adult but you will not be able to communicate properly. While they were being spoken to the main shaved their pussy’s so they were bald as a new born baby. With in a very short period of time Peter’s brain became fuzzy he tried to speak and all that came out was grunting and squealing noises nothing comprehendible.  Next the nurses released Clare and Peter from the chairs lead them over to a changing table were Clare and Peter were placed a cloth diaper was pinned on both of them it had a very thing soaker pad in the diaper so it would take more than several wettings. Then they were place in cream plastic knicker which had a waist lock to prevent un-wanted removal the nurse locked the special needs plastic knicker on Peter and Clare next came a white blouse semi see though which was place on both sissy their breast could be clearly seen though the material especially their nipples. The nurse put purple tight fitting track suit bottoms and track suit top on Peter and Clare the cloths did not hide the large bulge of the special needs diapers after the track suit the sissy were fitted with a special needs harness that buckle at the back it also had strap that went from the waist down past the crotch back up past the bottom and secured at the back with the chest harness preventing any removal of cloths. The Nurse connected walking rein to the harness know both Peter and Clare were secured the nurse took hold of the rein and walked them back into the main room over to were Lady Forreste. Judge Strickland, Mandy and Primrose were Lady Stickland then said Well girls it is time to go home and by the way Primrose and Petra {peter} Judge Stickland and Mandy and Clare are moving in because Judge Strickland is my longtime lover and know she is going to be my partner so you will all be step sisters won’t that be great.  Lady Forrester and Judge Stickland gathered the sissy girls together walked them to the lift poor old Peter looked like a teenage girl or young lady that is wearing diapers because he has a handicap especially as he is wear a special needs full body harness making his padded bottom look even more big with the straps pushing the padding out. It Make Peter waddle even more when he walks. They got out of the lift Peter tried to run on ahead because of the embarrassment of how he was dress but the harness prevented this so as he walks down the store isle his bottom waddle left to right, he could her people laughing a how he and Clare were dressed finally they got to the exit where a people carrier was waiting for them. Mandy and Primrose got in and were seated they had normal seats with a booster pad which meant when they had belt their safety belt on you could clearly see their cloth diapers and plastic knickers then  Peter and Clare were put in special car seats which secured them in.
96
Active Sissy Stories
/ Re: The Little Sisters of Gamma Delta
« Last post by BabyJay on December 10, 2025, 04:42:29 AM »
Delightful. Now the Delta Darlings are finally shopping for their frilly lingerie I hope the girls tempt them into buying the girliest and frilliest sets available in lovely pastel colours. Look forward to next episode.
97
Active Sissy Stories
/ Re: The Little Sisters of Gamma Delta
« Last post by sissyboy1212 on December 09, 2025, 08:54:50 PM »
Lace and Grace

       On Wednesday afternoon, the boys assembled in the quad. They quickly had realized they couldn’t really postpone shopping for new lingerie, since they only had the one set each. Their Big Sisters had dropped strong hints about a particular boutique in the quaint college town with knowing smiles and cryptic encouragement. The task ahead felt daunting, and they exchanged uneasy glances as they set off together. Lingerie shopping was uncharted territory, and the prospect of selecting such intimate things made their cheeks burn with embarrassment and nerves.

       The disquieted Little Sisters slowly made their way to “Lace and Grace.” As they approached the cozy shop, the boutique’s window display sparkled in the afternoon sun. In the display window, delicate pastel bras hung alongside embroidered silk robes and a multitude of other dainty and feminine apparel.
 
       Nate paused, uncertain. “Are we really doing this?” Nate muttered, his voice wavering.

       Milo tried a brave smile, “Let’s just… get in and out, quick as possible.” Then Milo nudged Nate through the door first.

       Every head seemed to turn at the soft tinkle of the bell above the door. Although there were only a couple of other customers, they were all surprised to see the four cringing college boys enter. The incredibly feminine space glowed with soft pinks and lavenders, and the air was thick with the scents of sachets and soft new fabrics. Velvet chairs and gilded mirrors enhanced the overall sense of feminine elegance.
Two of the store clerks, Anna and Becca, recognized the boys immediately from the moment they stepped in. They smiled mischievously at each other. They knew precisely why the boys were there. Anna, feigning ignorance, approached first and said, “Welcome to Lace & Grace.” She then asked with playful curiosity, “Are we shopping for our girlfriends today?”

       â€œOr maybe your sisters?” Becca chimed in, her voice teasingly sweet. “We have some beautiful sets for gifts, if you’re not sure what to pick.”

       None of the boys knew how to say the words, so they just stood there in cringy silence.

       Becca let the pained silence linger for a moment. Then, she exchanged a glance with Anna before adopting a mock-serious tone. “So, if it’s not for sisters or girlfriends, what brings you in today?” she asked, eyes twinkling.

       Milo fidgeted, shifting his weight from foot to foot, and Julian stared at his shoes. The boys exchanged desperate glances, each silently willing the others to speak up first. Finally, Owen cleared his throat and stammered, “Actually… uh… it’s not for anyone else. We’re… shopping for ourselves.”

       Anna’s brows shot up in mock surprise, and Becca’s lips curled into a knowing grin. “Oh really?” Anna replied, feigning innocence. “That’s so fun! You want some pretty things for yourselves?” Grinning, she pointed to a delicate pair of lavender panties on the nearest rack. She asked innocently, “What did you have in mind? Perhaps something soft and lacy like these here? Or maybe something a bit more sheer?” Her eyes sparkled as Owen’s cheeks turned a deeper shade of red.

       Nate attempted to explain, his face nearly as pink as the pastel bras on display. “Well, umm… we already have some… but we need more.” He added weakly, “It’s, uh, a sorority thing.” His feeble words hung awkwardly in the air. His explanation didn’t seem to explain much at all.

       â€œA sorority thing?” Becca asked teasingly, “I didn’t know boys could join sororities, but more power to you!” Anna couldn’t hold back a laugh, and Becca giggled with her, their amusement genuine but not unkind. With a wink, Becca said softly, “Relax boys, we’re Gamma Deltas—Madison told us you might stop by.”

       Anna added somewhat conspiratorially, “Just so you know, we have a surprisingly large clientele of trans women… and also quite a few adventurous and open-minded men… more than you might expect. So we are well ‘equipped’ in all kinds of frilly things that might match your anatomy!” She chuckled a bit more as she finished.

       The boys didn’t know whether to feel relieved or even more uneasy.
A moment later, Anna said, “Well let’s get started then! This is going to be such fun!” Her tone was warm, but her eyes danced with playful mischief.

       Then, Anna and Becca led them over to some of the racks of frilly, lacy lingerie sets. “Alright, boys, drop your jackets,” Anna instructed, “we need to check your sizes—bust, waist, hips, and all that.”

       The boys reluctantly placed their jackets on one of the velvet chairs, and Anna and Becca set to work collecting their measurements. Anna started with Owen, wrapping the measuring tape around his torso. She smiled, “Let’s get your bust first—stand up nice and tall, sweetie.”
 
       Meanwhile Becca sized up Julian and remarked on his graceful build. The two clerks quickly got what they needed and began holding up delicate bra and panty sets on the cringing boys. They began a running commentary on which ones suited them best. The two sisters then began interrogating the boys on their preferences for colors, fabrics and styles. They insistently coaxed the Little Sisters to be more specific about the lingerie they wanted.
98
Active Sissy Stories
/ Re: My Childhood in Diapers
« Last post by sonnysis on December 01, 2025, 01:07:15 PM »
Just want to add my appreciation for your writing BB. It’s like enjoying a parallel universe of human sexuality that I don’t need to physically experience, but can so easily fall into a make believe world to enjoy almost as well. ??🍷🥳
99
Active Sissy Stories
/ Re: Peter was a petty criminal
« Last post by sissy servant 737-820-633 on November 28, 2025, 06:26:41 PM »
WOW! What a long and exciting read
100
Active Sissy Stories
/ Re: Peter was a petty criminal
« Last post by Howarth66 on November 28, 2025, 12:00:27 AM »
The Two ladies approached the girls said why you naughty little girls you will pay dearly for this firstly we are going to take you to the special part of the department store to arrange special cloths for you. You will learn to be girls even if I have to use more magic follow me if you know what is good for you the girls follow Lady Forrester with Judge Stickland bring up the rear. They entered the lift and Lady Forrester pressed the button for the top floor when they arrive there was a reception desk with a sign sexual training for girls. Peter thinks about the sign and has a lot of apprehension what was going to happen. Lady Forrest says right girls first an injection this will stop any incontinence temporary for the purpose of this punishment when the punishment is finished you will revert back to nappies and rubber knickers. A nurse came out an administered the injections to all the girls they were then escorted into a changing room the nurses quickly stripped them of their boy’s attire and took of the rubber knickers and diapers.
All the girls Peter, Primrose, Clare and Mandy were naked they were placed in chairs and faced a big screen. Lady Forrester said time for you girl to watch a movie they all sat as the movie started there were flashing different colours made the girls feel dizzy as they got doper and doper Judge Strickland gave them a second injection this was to make them into sexy bimbos. The subliminal message was saying that they would choose the sluttish girly clothing even though they wanted to wear boys’ cloths that they would want to have sex with any girls they saw knowing they boy that had been physically changed into girls and as soon as they had climaxed, they would have a unbelievable need to dress back as diapered dependant toddler girls. Laid out on four different table was a set sexy underwear containing see through panties suspenders stockings and see through bra next each sexy item was a piece of boy’s underwear or clothing. Judge Strickland said right girls if you manage to dress like boy’s as you did earlier, I will immediately order that you can be changed back to your original male status, but if you fail, I will add time on your sentence as a diaper dependant toddler girl. The girls got up from the bench Lady Forrester got out a wand she waved it Peter hair ginger vagina got thicker the girl that had shaved vagina suddenly had hairy ones the girl could not stop themselves jumping up for joy singing I have a hairy vagina but their brains were say I want my pen-is back they were confused that they were so over joyed Lady Forrester smiled knowing it was part of the girls programming.
All the girls arrived at the table each had a section with their name on it. Peter looked at his first garments there was a plain pair of men’s y front type British superstore style next to the was a pain of emerald panty girdle with white lace around the top and leg openings the sort of firm control panty girdles the more mature ladies would wear except there was a large crotchless slit in the gusset which was also line with white lace. Peter thought no brainer men’s y front so he picks up one of the garments a put it on the he smiles that’s one up on Lady Forrester he then looked in the mirror looking back at him was a young girl in a mature panty girdle and his ginger vagina look like the girdle was made for him. Peter looked around all the girls had chosen crotchless panty girdles with suspender straps all in different colours pinks, red’s. white. Peter thought perhaps he would have better luck with the next garment on the table a men white vest would not be so bad he could hide his knickers with men’s trouser he just had to choose the vest. Next to the boy’s normal white vest there was also a green see-through nylon bra this would show his breast to their full even the nipples would show through.  Peter said not a problem pick up the garment but was confused again why was he use his hands behind his back to fasten the vest on and again when he looked in the mirror he saw he was in the bra. So, where the other girls next came the choice between boys’ socks or stockings you guessed it five minutes later Peter was look at his pale green stockings which he had fasten to the straps on his crotchless panty girdle he was looking more and more like a slut so were the other girls just in different colours. Next came pair of boy’s trainers or a shiny green pain of t bar Mary Janes before you could say Jack Robinson Peter had done up the Mary Janes. Peter looked around all them had failed they were dress looking like ladies of the night. Peter could see Clare bushy dark black pussy were as Primrose ‘s was bushy blond poor old Mandy had been kept with a bald pussy no hair just a slit in full view.
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