Sissy Boy Chuck Becomes Just SissybyKrazy35©
A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, then almost ran back to my room and masturbated furiously. I knew I had found something great.
For a while I only got to enjoy this new hobby every few weeks when my sister would go to a friend's house while my parents were working. Years later, when I was 19 and she 20, while in college she started going to Missy's house just about every day.
As soon as she was out the door I'd be putting on one outfit after another, and beating off between each one. Her nightshirts, her bikini, her short shorts, even the conservative dresses she wore to church. I looked great in them all.
One day after dressing in a short skirt and pull over sweater, I started looking for shoes. Instead, I found her diary. I just had to take a glance. Opening it to a random page, I read some boring blurb about a class she hated, Biology, I think. I flipped a few pages and read a blurb about Marcy, a girl in her class that she doesn't like. Boring, but when I flipped to another page, there it was, "Today when I went into my closet, the dress I had picked out for the dance wasn't where I left it and I think someone has been in my closet." Wow I better start being a lot more careful.
But on the very next page. "Today I found a spot on my new skirt. I know it wasn't there before. I know it sounds paranoid but I think someone's been in my room."
Not good, She's noticing things.
The next page was worse, "Found my panty drawer a little messy. I think Chuck is going through my stuff."
Oh God she knows it's me.
In a panic I looked further ahead. "Once again today I went to Missy's house. Before leaving I carefully arranged all my clothes. I came home and stuff was moved. Not much, but enough. Chuck was the only one home. It must be him. I wonder what he's looking for. You don't think he could be wearing my clothes."
Oh God now she's even guessed my secret. I've got to get out of here. I put her diary back, quickly changed out of my sister's clothes and put them all neatly back where they came from.
I went back to my room and pulled out my dick and started stroking. I couldn't get into it though. Every time I'd think of the sexy feel of those panties, I knew I'd never feel that thrill again, and got a little down in the dumps.
Then suddenly my bedroom door burst open. There stood Jessica glaring at me. Apparently she had come home early.
"Put that away." she said pointing at the dick in my hand.
I turned beat red and tucked my dick back in my sweats. "Get out of my room!" I Yelled.
"Don't get indignant with me. Get up and come with me" She demanded.
I quickly got up and followed her down the hall to her room. I thought she found something out of place. I'll just deny it, and never, ever go in her room again.
As I turned and walked into her room Jessica was sitting down at her computer. "You should have read further into my diary."
How could she have figured that one out "I I I didn't." I stammered
"Shut up!" she yelled as she typed on her keyboard "Not another word. I know what you've been doing little sissy boy. If you would have read further you would have read how Missy showed me how to rig up this web camera, and how I've taped all you're little fashion shows for the last week or so."
With that she hit another key or two and a video of me dressed in one of Jessica's nighties came up on her screen.
I know I flushed beet red and even as I stood there trying to create an excuse I could feel my dick start to harden as I watched myself on her screen prancing around the room.
She hit a few more keys and the video changed to me in a knee length black skirt and pink sweater laying on her bed reading one of her romance novels.
"I I c-c-can explain." I stuttered
"I said not another word." she commanded "Do I need to call up more videos? I have eight days of your little games."
I just shook my head no.
A few more clicks and the screen went mercifully blank.
Jessica stood and walked directly in front of me. "Now here's the deal little sissy boy. Missy and I watched you live."
I blushed again. Missy was about the only one of my sister's friends I liked. She was hot and now she too knew my little secret.
"I wanted to give the tapes to Mom and Dad." she continued
"Please don't. Dad will kill me." I begged
She grabbed my chin and looking me dead in the eye said "If you say another word that's exactly what I will do. Do you understand?"
I just nodded.
She let go of my chin and started pacing in front of me.
"I wanted to give them to Mom and Dad, but Missy talked me out of it."
I always liked that girl.
"Missy said we should hold these tapes over your fucking little sissy head and make you do everything we say or not only will Mom and Dad get them in their work emails, but we'll slip them in at the next school assembly and post them on U-tube."
I hate that Missy bitch.
"So sissy boy from now on your going to do exactly as I command. Is that clear?"
I just nodded, what else could I do.
Just then the doorbell rang. "Good timing." Jessica said "Let's try a little test. Take off those sweats."
"What the hell for?" I said
Jessica glared at me "That'll be your last outburst, or the entire town will get to know you as I do sissy boy. Now get them off or else."
I flushed beet red again but did as I was told. I was mortified standing in front of my own sister butt naked.
"Better." she said "now go let Missy in and get back here quick."
I reached for my sweats but Jessica snatched them away before I had a chance, pointed at the door and said "Like that!"
I walked down the steps and through the foyer covering as much as I could with my hands. I turned the knob on the door then ran all the way back to my sister's room.
Missy let herself the rest of the way in , closed the door then joined us in Jessica's room. Missy put a box on Jessica's bed and said "that's what I could part with." then turned and looked me up and down.
I was doubly mortified.
She said "He really is kind of girlie isn't he."
Jessica said "He says he'll be good.
Missy said "We'll see. Tomorrow after school." then she turned to me and said "I'll see myself out" and left.
Jessica just left me standing there looking stupid and went over and started looking through the box Missy had brought. When she turned around she handed me a pair of plain white cotton bikini panties. She said "Put them on sissy boy."
I did as I was told.
She said "come on turn around."
I did a little turn so she could see them all around,
"They'll do sissy boy." She said "Mom and Dad will be home in a few minutes. Keep those on under your clothes. You will be right here in this spot wearing only those tomorrow as soon as you get home from school. Got It?"
Once again I only nodded.
"And don't go cumming all over them. Those are Missy's. Now get out." with that she tossed me my sweats.
I went to my room, locked the door, then sat down and almost cried. They had me. What could I do. I had to figure something out. I tried to think but my thoughts kept wandering. Wandering to my growing dick. The fact that I was wearing Missy's panties would not leave my head. I pulled my sweats and Missy's panties off and began to stroke my boner.
A second later I heard my mother yell that she needed help bringing in the groceries. I let go of my cock and started to pull on my sweats. Then I thought better of it and pulled on the panties, then my sweats and t-shirt.
My sister made sure I spent a lot of time with my parents that night. After dinner it was a couple games of cards, then a long game of monopoly all at my sister's request and of course I agreed with all her suggestions, whether I really wanted too or not. Once, when we were alone in the kitchen, she pulled my sweats down a little. She smiled and whispered "Panty check." patted my ass, and went back in the other room.
It was obvious she wasn't going to let me get away without wearing them.
The next day at school, I had a hard on most of the day. It was so kinky having these panties rubbing on my cock all day.
When Jessica and I got off the school bus I went to my room took off all my clothes and then went to my sister's room. Jessica was waiting on me.
"It's about time sissy boy." she said. "There are two boxes on my bed. They are filled with clothes that Missy and I no longer wear or want. You want to wear women's clothes? These are now yours. You will dress in these clothes from the time you get home from school until Mom or Dad gets home from work. Do you understand?"
"Yes." I said, my cock growing hard at the thought.
"Pick out an outfit and get dressed." She ordered
I went straight to the box Missy brought over. I had tried most of Jessica's clothes before. I found a nice leopard print mini, a black lace bra, and a black button front shirt I thought would go with the skirt.
I started to put on the bra when Jessica yelled "Change your nasty panties, Your not a skank." and tossed me a black lace thong from her box.
I changed into my new outfit, then was made to do a turn so I could be checked out again.
Jessica told me to put the rest of the clothes away in my room, she expected them to be in my drawers and closet where they belong. I took the two boxes to my room and as I sorted out my new wardrobe, my hard cock ached for release. There was some nice stuff in the boxes and I was somewhat anxious to try them all on. Before I could get much put away the door bell rang.
"Answer that Sissy." Jessica bellowed.
Down the stairs I walked praying it wasn't the UPS man. I peeked out and saw it was Missy. I opened the door and let her in. She asked "Is Jessica upstairs Sissy?"
I said "Yes." and she started up the stairs. Damn she looked good. Missy attends the local catholic school so she was wearing her plaid skirt and white button up shirt.
I started back for my room to put the rest of my stuff away when I got called into my sister's room. When I walked in Jessica walked up and lifted my skirt showing off my thong. "See." she said "She's just not right."
Missy agreed and told me to strip. I thought about protesting then decided I better not. I did as I was told. As soon as I was naked I was escorted into the bathroom and made to stand in the shower. The two girls produced safety razors and shaving cream. First they shaved my legs then my arm pits, then giggling the began to shave my pubes. By the time they were done I didn't have a hair on my body and my cock was rock hard.
They took me back into Jessica's room and explained to me that I was to shave myself hairless, like they just showed me, every third day.
Next Missy produced a wig and showed me how to wear it. Then the two girls taught me how to do my make up although they assured me most days makeup would not be required.
Then I got redressed in the clothes I had on before minus the panties. Missy stuffed fake breasts into my bra then looking down said "Now take care of that." pointing at my hard-on.
I just stood there. What was she wanting me to do?
Jessica took over the lead "She means do what we all know you want to do. Beat off."
I was in shock. I didn't think I could get myself off with my sister watching, but I knew better than to argue so I grabbed my cock and started slowly stroking it.
My sister walked out of the room and left me alone with her hot friend. Missy stepped in front of me and replaced my hand with hers. Her soft hand stroked gently but quickly driving me straight towards the edge. Just as I thought I would cum, Jessica reentered the room.
Missy quickly let go before Jessica could see what she was doing. "Hurry up Sissy. We don't have all day" She scolded.
"Here." Jessica said handing me a washcloth, "Don't you dare get any of that on my carpet."
Jessica walked past Missy to her computer. As soon as she was occupied and could not see what Missy was doing, Missy raised her hand and licked my pre-cum from her hand.
That was all I could stand. I shot a huge load into the wash cloth. My knees went weak as I pumped out shot after shot. Before I was even finished Jessica stepped in front of me and said "Good. Now get yourself cleaned up."
I finished the last few pumps then gently wiped off my softening cock then started pulling on my panties.
"Hold on Sissy." Jessica said "We have something to do first."
Jessica had me stand with my feet spread as far apart as I could get them. I had no idea what these two were up to now, but Missy circled around behind me. Before I knew what she was doing, She reached between my legs, grabbed my flaccid cock and tucked it up between my legs. As shocked as I was, the next move shocked me even more. Missy placed a huge piece of tape over all but the head of my cock, taping it securely in place.
"Now put your panties on." Jessica demanded.
Once again I did as I was told.
Jessica and Missy both held my skirt up and admired their handy work. "It worked." said Jessica.
"I told you it would." Missy said then looked at me and continued "Not only will you remain shaved, but you will remain taped as well. You may remove it at night for your shower, but in the morning, before you dress it will be taped up.
"But how will I pee?" I asked
"You'll have to sit." Jessica said "like the little lady you are."
"If you feel the need to play with that thing." Missy said, "You better do it at night, while it's not taped. During the day you are Sissy. And Sissy doesn't have a cock to play with."
With that she escorted me over in front of Jessica's full length mirror. With my face done up and the wig on I really did look like a girl. My only thought was that if my cock wasn't all taped up, I'd probably have a raging hard on.
Just then Mom yelled "I'm home."
Oh no we'd lost track of time. Quickly I started to undress. "Not in my room you don't." Yelled Jessica.
I gave her a pleading look, but seeing no mercy I peeked out the door then ran to my room to change clothes and remove the makeup. As soon as I was in my sweats and t-shirt and had cleaned myself up, I went downstairs to get a drink. In the kitchen mom stood talking to Missy and Jessica. I stepped around them and got a soda from the fridge.
"Jessica tells me her and Missy are working on a project after school here at the house." Mom said.
I blushed beet red and said "Yeah I guess so."
"They tell me they may be working on it everyday for a while." Mom continued "I hope that doesn't cramp your style."
Both girls giggled and the tape on my cock seemed to tighten. I looked at both the girls and without missing a beat said "I don't care. If they need anything, all they have to do is ask."
Both girls gave me a sly look as I slid past them into the living room.
It took a couple days for me to get comfortable taping up my cock and keeping it that way all day. But as I got used to it, it wasn't so bad.
The girls worked on their project everyday at first. I was taught how to sit like a lady. I practiced doing my own make up. I was corrected anytime I let my voice deepen at all. And anytime I did something, as they would say, like a man, I was forced to repeat the action over and over again as Sissy until I got it right.
After just a couple weeks, most of Chuck was gone in the time between school and the time Mom got home. During that period of time each day I became Sissy.
I know my sister thought she was torturing me but in truth I derived great pleasure from being Sissy.
Because I was so thoroughly Sissy for those couple hours each day my training had pretty much ended. The girls made Sissy do their homework, do their hair and their nails, and all kinds of chores around the house. Oh and when Missy had her period, so did Sissy, and I had to wear a pad in my panties for a week.
By the end of a month I was beginning to think they were done trying to torture me and were beginning to be friends with Sissy.
Oh they still had me waiting on them hand and foot, but some days I was left alone in my room, to do as I pleased, as long as I did it as Sissy. Other days we talked about boys, read romance novels or just watched TV.
It seemed us three girls, were growing tight, which was funny because anytime I saw the two of them and was dressed as Chuck, they wouldn't give me the time of day.
Another month passed, and Sissy was being treated as more of an equal. We did each others nails and hair. Sissy still had her chores to do, but Jessica had taken to doing her own instead of making Sissy do them.
Then one day as the three of us were sitting around talking, Jessica admitted that she had grown fond of Sissy.
Missy said to Jessica "I still hate that creepy brother of yours, but I like Sissy a lot."
"Yeah." agreed Jessica "I wish he'd just disappear altogether and it would be just me and my little sister Sissy." with that she gave me a hug. A hug. I can't think of the last time my sister hugged me. It kind of freaked me out.
When she broke the embrace, I said "I've come to like you girls a lot too. But, since school is out soon, I guess we only have a couple weeks left"
Samantha's jaw dropped. When she recovered from her shock she said "Sissy, I'm a little surprised. You think this ends with school." Then her voice got a lot more threatening "Mom leaves for work every morning at seven AM and gets home sometime after six. That means for 11 hours a day you WILL be Sissy. Remember I still have the videos and we're about to ratchet Sissy up to the next level." Her voice then returned to the friendly tone she had been using "Won't that be great?"
"Yes." I answered, "I hadn't thought of that." I really hadn't. I'd been enjoying being Sissy for a few hours a day, but eleven hours a day and what the hell did she mean about the next level. I thought I would get to spend this summer like the ones in the past, outside playing ball, but it looked like Sissy was going to be inside playing dolls.
The next day after school, I was getting dressed when Samantha appeared at my door. She threw me her little yellow sun dress. She said "I believe you have a yellow bra and panty set with butterflies on them that will go nicely with that."
I said "Yes I do, but why?"
"I'm not wearing that any more." She said "Besides you're not supposed to ask a bunch of questions."
She turned to start to leave then stopped "Oh yeah. Do your makeup today too. I have something special planned." then she left.
I got dressed then sat at my dresser and carefully did my makeup. Part way through I heard the doorbell ring. Missy is here, I thought. Jessica yelled from downstairs "I'll get it."
A few seconds later I heard the girls giggling as they came up stairs and into Jessica's room. "Hurry up and get in here Sissy." Jessica yelled. "The conversation may start without you."
I hurriedly finished my makeup, arranged my wig and then got up and admired Sissy in my full length mirror. "Damn boy, you make a pretty girl." I said and with a bit of a pirouette headed for my bedroom door.
I loved the look and feel of this sundress so much I damn near skipped down the hall and into Jessica's room. That's where my elation ended. Standing in the room was Jessica, Missy, and another girl. This drop dead gorgeous blonde was about 5 foot 6 and dressed in the catholic school's uniform just like Missy, but her skirt was much, much shorter, and her shirt was stretched tight over the largest breasts I've ever seen.