Sissy Panty Boy Stories
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Sissy Panty Boy Stories
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One-Handed Reading: Sissy Shopping Story (TG) "Can I help you find anything?" The salesgirl's voice startled me a little. I turned and smiled at her, then held up the two tops I had been debating over, one in each hand. "Actually, yes, you can," I answered, still smiling. "I can't decide which of these to get. Maybe you can help me decide?" The salesgirl nodded and turned her eyes to the shirt I I held out first. "This one?" I inquired. It was a lavender stretch shirt, princess seamed with three-quarter sleeves ending in cute turned back cuffs. I already had one similar to it in white, except this one had the longer, more pointed style of collar. "Or, this one?" I held the second one out for her to see clearly. This one was a very cute hot pink knit top in a cotton-lycra blend. Very stretchy and form fitting. It, too, had the popular three-quarter sleeves, but these ended in a one-inch ruffle. The neckline was scooped, though not deeply. "They are both very contemporary styles, ma'am, and either would look fantastic on you!" the salesgirl enthused. I knew she was going to say something like that. I wanted to coax her into doing it so I could drop my surprise on her, see if she really wanted to make a sale or not. "Oh, it's not for me," I said, shaking my head. Her eyes got a knowing look, thinking, I'm sure, I was going to say it was for a friend or relative. She was right, but not the way she imagined. "They're for my brother." The salesgirl's eyes widened in confusion as she turned her head and followed my arm that now pointed at my younger brother standing slightly behind a nearby clothes rack. His face was flushed in humiliation. "You… You're going to make him look like… like a girl?" the salesgirl stammered, looking back at me. Her eyes kept darting back to my mortified brother. She looked like she was trying to keep from laughing in shock or amusement. "No," I answered casually. "He's going to be dressed like a sissy boy. I want everyone to know that he's just a boy in girl's clothes. At least when they see him up close." My brother turned an even deeper shade of crimson and hung his head in shame. The salesgirl's head swept back and forth between him and I, trying to figure out if this was a joke being played on her or something for real. "You're serious?" she asked. I nodded gravely. "Why are you doing this to him? I mean, did he do something bad to deserve this or what?" I motioned my brother to come over and stand next to me. He shuffled over, head still bowed. I placed a finger under his chin and forced him to lift his head. "He is a bully sometimes," I told her. "He doesn't usually use physical force on anyone, but he seems to dearly enjoy verbally teasing and insulting others. Especially boys who are smaller than him. He calls them 'sissy' and 'pantywaist'." The salesgirl was nodding in understanding as I spoke. "Even girl's get unmercifully teased by him; pulling their hair or making fun of what they are wearing. Isn't that right, Chris?" I looked hard at my blushing brother. He shrugged a little, but looked even more scared as he saw the salesgirl was glaring at him. "So, our mother decided he should see how it feels and left it up to me to make sure he does," I looked smug. "This is my solution." The salesgirl muttered how she couldn't stand bullies when she was in school and thought this was a great way to get one back, all the while glaring at Chris. She turned to me and said she'd be happy to help. I was relieved, glad she didn't freak out. She brought my attention to the clearance sign on the rack I had taken the two tops from. Fifty percent off. She said I could get him both for what I was figuring on paying for one, now. I beamed and thanked her, handing the two tops to Chris to carry. "We have some really cute skirts I bet he'll be so embarrassed to wear!" the salesgirl gushed, getting into it. I shook my head, though. "No. Not right now, anyway. Only girls wear skirts and he isn't going to be a girl. Just a sissy. I'd like to find him jeans or shorts. Something girlish, though. He'll only wear skirts for special things." My brother looked sharply at me when I said that. The salesgirl giggled and seemed to think for a moment. "We have a few things that may be just what you're looking for," she said brightly. "Great!" I beamed back. "Tell you what, you find something for him to match the pink top. I want him to try it on before we buy it, if that's ok?" She said it was fine; no one was using the fitting rooms now so it shouldn't be problem. "Good," I smiled, turning to Chris. "Go try on the pink top and whatever bottoms she hands you. Do you understand?" He nodded slowly, face still red, and trudged off towards the fitting rooms. The salesgirl, Judy I now noticed her name tag read, turned to me. "What about a bra to fill it out a little?" She asked. "No," I chuckled at her enthusiasm. "I want him flat-chested. Fifteen-year-old girls would have some development by now, but like I said, I don't want him to look totally like a girl. Besides, he's already wearing a pair of pink satin panties that don't fit me anymore. You should have heard him holler when I made him put them on before coming here!" We both laughed. Judy went off to get the item she had in mind for Chris while I rummaged through a few more of the racks, looking for other things for him to wear. A short time later, I had found a couple more outfits I thought would be cute for him and headed towards the fitting rooms. Judy was waiting outside of them for me. She grinned from ear to ear as I walked up and placed my other selections on the counter. "I had to help him get dressed in what I picked," she told me, conspiratorially winking. "I saw the panties. Very cute!" She giggled. "Are you ready to see him?" I smiled and said yes. Judy stuck her head in the archway and called for Chris to come show us his cute new clothes. He came shuffling out, still red in embarrassment and with his head hung low. "Oh, that's just adorable on him!" I almost squealed when I saw him. "Excellent choice." He stood there in the pink knit top. The ruffled sleeves ended just below his elbows. The cotton-lycra clung to him well, seeming to emphasize his very boyish chest, as opposed to enhancing the small breasts a girl his age might have had. The scoop neck made this contrast even more noticeable as well as making his boyish face and hair very obvious. Judy had even placed two small, pink barrettes in his hair on the left, much like a girl would wear. Yet it did little to make his hairstyle seem very feminine. I loved it. But I loved what else she had picked out for him even more. It was a pair of dark blue denim capris. The legs ended just at mid calf and had a bright pink flower pattern at the hem, fading upwards for about six inches. The capris looked like they might be a bit stretchy as they were a bit form fitting from his waist to crotch. It made the fact he was a boy even more prominent since no effort had been made by him to hide his genitals. A small, very un-girlish bulge made that all too evident on the flat front. I could see they were back zipped, too. I looked to Judy and gave her a quick hug. "That is sooo perfect," I was grinning at how boyishly sissy Chris looked. "I'll take it! Ring them up with the other stuff, please." Chris' head snapped to look at the small pile of clothes on the counter, trying to figure out what was up there. "Go put your sneakers back on, Chris," I told him sweetly. "And, put the clothes you wore before into a bag." His eyes got wide, realizing I wasn't letting him change out of the cute capris and top outfit. "After I finish paying Judy, and since you have not given me much trouble so far today, we can go to the arcade so you can play a few games and say hello to your friends before we get you some shoes to go with that!" I smiled as he looked about to faint… -fin?-
An Early Crossdressing Adventure: The Next Day Since the tale of one of my early real-life crossdressing adventures seemed to spark interest (and judging by some of the comments, some bulging panties), I thought I'd write about the following day and what my friend's step-mom made me do. Again, no real sexual contact in my adventure. As this was 35+ years ago, my recollection of details has been colored by time and fond memories. Thus this (mostly) true tale is lightly embellished by wistful memory and a bit of spice and half-remembered dialogue for reading purposes. To avoid the kind of clunky use of "my friend" and "my friend's step-mom" from the last post, I am going to give them names. These are, of course, not their real names ... or are they? We shall call my friend Geoff and his step-mom Sara. She always told me to call her Sara like Geoff did, though my upbringing caused me to call her Miss Sara as a compromise between her first name and Mrs. "Smith". This was in
(Hello, this story contains heavy diaper and humiliation scenarios. If these kinds of things upset you then you should stop reading immediately, But for everyone else enjoy)
“YOU LITTLE BASTARD!!!!” screamed Natalie as she continued to chase the school’s local prankster James throughout the halls. “YOU BETTER HOPE I DON’T CATCH YOU”
James in the meantime couldn’t stop laughing as he clumsily ran through the halls with Natalie hot on his heels. He had just pulled off another successful prank by super gluing one of Natalie’s hands to a baby rattle and the other to a childish baby tambourine. H
This was originally posted by Feminization-stories, who has since deactivated their account. They gave permission for people to reupload their stories. I had just hit the best homerun of my life. I tore through the bases, not watching the ball as it soared above the head of the outfielder. As I reached third base, the pitcher had gotten the ball. I could risk it all, or play it safe. I decided to go for it. As I sprinted toward home plate, the pitcher threw the ball to the catcher with incredible accuracy. I slid onto the base, just before the ball found its home in the catcher's mitt. The crowd roared. I had won the tournament for the team. I, Wade Peters, was a hero. The horrible ringing of the alarm clock woke me from my slumber. My eyes opened to stare into the soft pink ceiling. The dream ended, and the nightmare begun. I rolled out of my large pink bed, throwing the stuffed animals I slept with aside as I walked over to the pink dresser in the corner of my room. I opened
Before the story begins, I would like to say something. I wrote this story over 2 years ago so when part two is released, it will be much better than this.
I was walking around my old primary school’s summer fete. It was on once a year and I always came to see how my school was doing and to see my old friends but this year none of my friends had shown up. I decided to stay for a bit just in case one of them came late and to look at all the stalls.
“Hey greg.”
I heard a voice coming from behind me. I turned around and saw it was Darcey, a girl who I used to fight with a lot. We teased and bullied each other a lot when we
W
I honestly do not recall if I ever posted this anywhere before now. I know I have sent it to one or two people as a goodie present. Oh, well, yet another tale of the eponymous Chris in yet another incarnation in another situation with the same humiliations. EDIT: Oh yeah! I posted a long time ago as "The Shopping Trip". D'oh! Nothing new or ground-breaking here. Just a one-handed fantasy story. I do recall I had a second chapter in mind, but i never got around to writing it. Or made notes. I don't really recall what it involved but it was not a direct followup at the shoe store or arcade. Hmmmm, maybe it'll come to me. Enjoy! And clean up afterward, dammit! The floor's getting tacky. Like my jokes. >_> ^.^;;;
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Enjoyed your story, especially the description of those cute capris -- perfect for Chris's sissy outfit. (I love wearing femboy outfits myself, including capri leggings -- even tights and miniskirts. So I'll be looking at your other stories!) Hugs.
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Hi my name was Timmy and i was a normal boy of 6. I do all the boy things like baseball and playing outside, video games and other things. My mom always said about my hair being longer than boys should have, but i had secret passion that my mom didn't no about. Well you’probably wondering what my favorite thing to do is, been about years now that I have been stealing and wearing my cousin’s pink pull ups diaper when they would come over for holidays and spend the weekend. Me and my cousin were same height ans she is only 4 years old and everyone thought that i looked like toddler around 3 or 4 years old. One day i was riding my bicycle wearing one of my cousins pink pull-ups under my shorts, and they are thick between my legs. I was daydreaming how these pull ups fit me very good and even started to giggling like a little girl as i rode my bicycle chair stuck and i hit curb and went flying until i hit ground and my pink pull ups were in plain sight. I opened my eyes cute lady with little girl. Lady came and asked: Are you okay sweetie that bicycle looks to big for you honey you should ride little kids bicycle. I seat up and saw big rip in my shorts. Is she going to be alright mommy little girl asked? I don't no sweetie little girl mom said. I said yes i'm fine i hit ground because bikes chain got stuck. Look mommy she ripper her shorts little girl said. After hearing what little girl said I realize she thinks I’m a little girl too because of the pink pull-ups diaper im wearing. Then she asked what's your name I"m Jessie and im 4 years old little girl said. I didn't wanted to say my real name and that im actually a boy not a girl so i had to thing something quickly so i said I"m Susie. I stand up and I see the little girls mom staring at me, i tried to keep fabric together but no luck. Darn it looks like I ruined my shorts my mommy is going to be very upset for what i did It's ok sweetie for little girls it happens sometimes. Then they both came to me and i saw that little girl is almost same height as i am. Her mom said you can't go home looking like this you should come with us that you could barrow outfit. “Ummmmm I don’t want to be a bother you both and make trouble. It's ok sweetie lets go inside. And it happens that i hit bike near the little girls and her moms house. Then little girl grabbed my hand and led me up into they house. “Let’s race to the top of the stairs Susie, Jessie offered. Ready? We started running up the stairs as fast as we can. “Girls no running in the house specially up the stairs" We turned around that we could say sorry but something happen my shorts fall down reviling my pink pull-ups diaper. Oh it looks like she is wearing potty training panties and let me know sweetie if you need to go potty. Jessie bends down by my feet and helper me to get out of my ripped shorts. I'm been standing in their with princess pull-ups while Jessie holds my torn up shorts. Then she gives my torn shorts to her mommy that she could throw them away. Now sweetie now get her dressed up than your new friend can have lunch with us. Jessie took me to her room and i saw that it was pink baby girl nursery room. Then i said: wow Jessie you have really nice room. Thanks, Susie she said i bet you have same room like me. Of course i had you lie” yes i said a little bit similar” Then she got to her closet an opened it and i saw just skirts and little dresses I don’t see any pants or shorts. I said wow you got a lot cute clothes i said. All I see is skirts and little dresses I don’t see any pants or shorts. I don’t have any shorts or pants my mommy said girls wear dresses and skirts and only boys wear shorts and pants Jessie said thank you now lets get you a new outfit she said. The came back with pink camisole, she took of my red t-shirt and put camisole on me. Jessie walked over to her dresser and opens one of her dresser draws and holds pink girly disposable diaper and pink plastic panties. These fits me and looks like they will fit you too because we same height. So you still wearing diapers i said? Yes im wearing them all the time its better for me and for mommy then she changes me. My mom thinks I sleep better wearing a diaper with the plastic panties. Susie now go to a bathroom and change because i see your training pants are wet. I looked down and of course i saw my wet training pants. She handed me pink disposable diaper and panties and said : go to bathroom change and come back. I grabbed the diaper and panties and got to bathroom I seat down on the top of the toilet seat took off wet pull-ups cleaned myself then wrap the diaper around me, i taped both sides tight. I look at myself in the mirror and saw myself wearing a diaper with pink camisole, then i slide op pink diaper panties and left the bathroom. Then i came back Jessie picked up hello kitty sundress she walked to me slide over my head making my hair all messy. Oh that dress looks so pretty on you Susie you should always wear dresses because they are more comfy than pants or shorts. I look at myself in the mirror wearing the pink sundress, then i fell how Jessie puts pink socks one me. Susie sit on bed that i could put your shoes on i sat on her bed, and she slid black Mary Jane shoes on my feet. The suddenly she started to brush my hair and putting them in pigtails with pink hair bows holding them. Its done she said you can look in mirror if you like Jessie said. I stare at my reflection in Jessie's full size stand up mirror on her wall next to her closet door and i saw myself looking like 4 years old baby girl not a boy. Wow I look like a total different person i said. "Yes you look very pretty just like me. The we hear her mommy calling us for lunch. We run into the kitchen and see grilled cheese sandwiches ready for us. "Wow Susie you look like a totally different girl jessie mommy said. I think you should wear dresses all the time like Jessie. We both continue to eat till were done and Jessies mom walks in and see's us
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