Crossdressing Stories

THE PUNISHMENT

The Punishment Crossdressing Story

It all started innocently enough. I never meant to do it, it just sort of happened. I got home from school, when I was in the 10th grade. I put my bag down on my desk, and noticed that mom had left the laundry basket on my bed. This was her signal that I was supposed to put the clothes away in my drawers, and bring down any dirty clothes I had.

So I put everything away, except when I came to the underwear, there was a problem. Mom had accidentally left one of Jody’s panties in my pile. Jody is my elder sister who is just 2 years older than me. I held her panty in my hands, feeling the silky material. I was a typical 10th grade boy, so as you can imagine, my mind raced at the thought that I was holding panties in my hand.

I had naughty thoughts on the mind all the time, and I had wanted to get into a lot of girl’s pants at school. For some reason, I had an urge to try them on, to see how they felt. I locked my door, closed all the shades, and put them on.

They were so different! Not rough or clingy like what I wore, but the smoothest, silkiest feeling, like I was wrapped in softness.



“Nick, are you in there? Why is your door locked!” said mom.

I didn’t know what to do, so I quickly pulled on my jeans, and then went to unlock the door.

“Why are all your blinds closed? What were you up to? Wait, don’t tell me. I don’t think I want to know” she said.

I was so close to being busted! I was lucky she didn’t see me. What would she have said?

“Come on, we’re late. We’re taking your father out to dinner tonight for his birthday. Don’t you remember?”

“Oh yeah” I said. She dragged me on out of the house, and we got in the car. With every step I took, I noticed the panties. The silkiness against my skin. I felt so turned on! I couldn’t explain it. And now I was wearing them in public! Without anybody knowing! When we sat down and the waitress came out to serve us, all I could think of was the fact that I was wearing panties, just like her.

Needless to say, I was excited all night. When we got home, instead of putting the panties back in Jody’s room, I hid them in my closet. It was only a few days later that I wore the panties again. And again, I got really excited. So for some reason, I decided to sneak into my sister’s room. Nobody was home, so who would know?

I dug through her underwear drawer, until I found her bras. If the panties made me that excited, I wondered what the bra would do. I took it back to my room, and tried it on. That excited me even more, so I stuffed it with some of my socks, then put on a white T-shirt. You could clearly see the bra underneath, and it jutted out, like I had breasts. I almost came in my pants. I made myself climax, then quickly took everything off and hid it back in my closet. I felt shamed and embarrassed, but it was so exciting! I knew I was hooked, and would do it again tomorrow.


In fact, almost every day I would wear Jody’s under garments. I even wore the panties to bed one night. But they were starting to smell from having been worn too many times. So I reluctantly put them in the wash. I waited a few days, and then dug through Jody’s drawers when I had a chance to find them, or a similar pair.

Nobody would know a thing! Some time passed, and I was still doing it. It was so exciting that I wanted to try to push the envelope, and do something more daring. So I waited for a good time when nobody else was home, and went into Jody’s closet. I dug through all the things on hangers, until I found one of her blouses that might fit me. She didn’t wear it too often (I didn’t think), so she wouldn’t notice it. And there was a red plaid skirt that she used to wear to school, but didn’t anymore.

I took that too, and went back to my room. With the door locked, and dressed up in full female attire for the first time. It felt wonderful! When I was fully dressed, I laid on my bed like a girl does,and read a book. I slid forward a bit, and felt some warmth between my legs. I moved back and forth a couple of times, and bam! I climaxed.

I ran to get tissues to clean it all up. That was stupid of me! But for some reason, thinking of myself as a girl made me really turned on, and made me climax so easily! I wanted to be with a girl so much, but this was exciting too. I would just do both. If I could get Lynn, my crush, to go out with me, I’d still do this in my spare time. Perhaps, I could get some of her panties too. Then I’d be wearing *her* clothes. Now *that* sounded really exciting to me! Over the next few weeks, I kept dressing up. Sometimes with just the panties, but sometimes in full outfit. I stole a pair of pantyhose from the laundry room, and started wearing those too.

The cotton crotch turned me on for some reason. I tried on some of Jody’s shoes, but they were too small. I found an old pair of mom’s, and I could get them on with a struggle. But I was afraid to try makeup or anything. That would be too hard to get on and off. But I did take one of Jody’s necklaces. The rings and bracelets were too small to fit on me.


Too bad. I had a couple of outfits now. I loved the one yellow floral dress, because it was such a soft material, and when I whirled around, it would swish against the pantyhose, and send shivers up and down my spine. I just loved it! It turned me on so much! But one day, even in full dress, it didn’t seem like enough. I wanted more! Nobody was home, so for the first time, I left my room dressed as a girl. I was *so* afraid that someone would look in the windows and see me!

But I got into Jody’s room safely, and took a couple of her books, and a magazine. Then I went back to my room. I had something to do now when I was dressed up like a girl. I read her copies of some girly magazines. I was so thrilled that I was reading *girls* magazines. I also read her fashion magazines, and was fascinated by all of the women’s clothes, makeup, and accessories.

I loved reading about girls, and wanted to know all there was to know about them. One day I finished her copy of Cosmo, so I went to put it back, and find the next thing to read. I was sure that nobody was home, so I snuck into her room. I dug around, and found a couple of things that looked promising. I held them to my chest, like the girls at school held their books, and turned around. There, standing in the hallway was my sister. I tried to turn and hide, but she saw me.

I was so embarrassed. She grabbed my hand and took me to her room.

“I.. I.. I am… s..so..sorry!” I stammered, looking down on the floor.

“I knew something was going on with you. You have been acting kind of strange for a few months now Nick.” Jody replied, looking a bit tensed.
“I don’t know what got over me. I am really sorry Jody. I promise.. I will never do this again.” I answered, almost about to cry.

“Well, I am going to tell mom and dad that you have been going through my stuffs without my permission!” Jody scolded me.

I was paralyzed with the thought of it. My parents would surely beat the crap out of me and things would never be the same ever again. I begged Jody not to tell our parents and was at her mercy. Seeing me so scared; she had a change of heart.

“Okay, I won’t tell them but from now on you have to do as I say.” She said. “Fine, just don’t tell them. I will do anything Jody, please.” I said hopelessly. “You better get changed now. Mom’s going to be home soon.” Jody said with a smile, knowing that I was completely under her control.



I rushed to my room and tried to undress as fast as I could. I couldn’t believe how stupid I had been and keep scolding myself in my head. After I cleaned up, I took all the girly stuffs that I had collected over the months and gave it back to my sister. She was a little pissed off that I used her stuffs but she didn’t say anything else. After that I went into my room and just laid in my bed feeling very ashamed and guilty. I promised myself that I would never dress up again, ever.

For the next couple of days, everything was quite normal. My sister rarely bothered me and I was pretty much over the things that happened before.

One day, we got an invitation for a wedding program from a distant relative. Me and my sister were just too persistent not to go, so just my parents were going to the wedding. They would be gone for 3 days as the wedding was happening in another city quite far from where we lived. I was already planning to have some beers and chill with my friends after my parents would be gone. The wedding dates arrived and my parents left.

They warned us not to do anything stupid when they were gone. As soon as they left, I got back to my room and was just about to text my friend, Jody comes in. “What do you want?” I ask her, feeling annoyed.

“Oh, you will understand what I want in the next few moments dear.” she said with a laugh.

“What?” I asked her again. “I want you to do all the house chores for the next few days until mom and dad arrives. You know, cook food, do the dishes, do the laundry and everything else.” She said with a grin on her face.

“No way! I won’t.” I said angrily. “Fine, if you won’t then I will tell mom and dad what you were doing with my stuffs!” She said and turned around marching to the door.

“Wait…” I screamed, realizing I had no other options. “I will do it.”

“Good, now that’s like my good little brother. But there is also one other thing I want you to do.” She said.

“What?” I asked.

“You will have to dress up like a girl and pretend to be a girl. You will only wear girl’s stuff from now. I know you want to. So, it will be fun for you too.

But I will decide what you can and can’t wear, understand?” She said. It was more of a command.

I knew it was pointless arguing with her and the thought of actually pretending and living like a girl full time seemed to be quite exciting. So, I nodded to her and she told me to come into her room. We both went into her room and there she put makeup on me, did my hair and also made me wear some of her accessories; her necklace, bracelet and her earrings. It was a very tingling sensation. I was really loving it.

Then she told me to get into her white summer dress and black pantyhose. I was blushing now. I changed into her dress and pantyhose, it was just amazing. I checked myself in the mirror and seeing me dressed liked that turned me on really hard. I tried to control my emotions as much I could. My sister was happy with what she saw in front of her. I was her slave for the next 3 days. That was the punishment of my sister but to be honest, I think it was more of a dream come true for me.

The End

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11 Comments

  1. I can relate.

  2. I wish I had a sister like that dress me up in vintage lingerie and dresses

  3. Love the stories!!

  4. Love the stories!!❤️❤️

  5. Similarity, my older sister used to dress me up for many years starting when I was quite young and take control of our time together to her satisfaction; often with a girlfriend sleeping over for the night. Loved the attention then, and now with my wife. Women are such gorgeous and complicated creatures, who wouldn’t want to be one, if only in dress?

    1. I wish my sister had found out jasmine

  6. I can relate to that, but it started with me putting on lipstick then slowly moving on to wearing clothes. So now I go the whole girl. Full makeup and clothes, the sexier the better.

  7. When i was 13,my sister,Jenny was 15 and a very good looking girl,slender and petite and had blondish hair.She was just out of puberty,but was still having the problem of bedwetting,that i was told was somewhat common with girls going thru puberty. Since her bedwetting started before she was 12.mom and dad had her wear cloth diapers and plastic pants to bed every night and at bed time mom would go into her room and put the diapers and plastic pants on her and i would often see them on her and thought to my self how much she resembled a baby with them on! That spring in May,i was 13 and jenny was 15,and we finially made our First Holy Communions together in the class with the 7 year olds.That sunday morning,i put on my suit and ty and jenny took her bath then went into her room where mom and dad were waiting to dress her in her communion outfit.A while later they brought her out and she looked very cute in her short sleeve,poofy,top of the knees communion dress and veil with her lace socks and white mary jane shoes! Mom then lifted up the front of her communion dress and showed me the cloth diapers and plastic pants that they had her wear under the dress and told me that she was like the littl girls and that i wasnt to tease her! Being 13,i got an erection right away seeing her and thinking how cute she looked! Later on that next week,i got home from school and mom was out shopping and Jenny stopped at a friends house,so i was alone.Her communion dress and veil were on a hanger in her room along with her lace socks and shoes.I quickly got naked and pinned on her cloth diapers then put the plastic pants on over them,then put her dress on,then the veil and was walking around in the outfit!I didnt know that mom had come home and she caught me in Jennys outfit!As she was yelling at me,jenny had come home and also saw me and called me a pervert! I was made to wear some of jennys bedwetting diapers and plastic pants for two months as my punishment after school and on the weekends!

    1. To Jeremy-Your sister was dressed correctly for her First Communion! In many parishes,a cloth diaper and plastic pants and under shirt is worn under the communion dresses to represent the girls purity of her baptism as and infant.

  8. I won’t to go shopping dress up

  9. So loverly the first time you dress fem you want to do it all the time

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