Ever dressed up with sister?

[Lyric]

I did once in a while with my sister who was 3 years younger than me. She would let me wear her panties and training bra and later her regular bra Many years later we talked about this and my diaper wearing which she rediscovered

 

[dogboy]

When I was in 2nd grade, I found a duffle bag of old clothes in our basement that I guess were my mom's. I asked if I could dress up in them and my mom said yes. My cousin Billy who was a year older than I would come over and we'd dress up as girls. It must have been that Halloween that my mom asked if I'd like to go as a girl. She got me a blond wig, a dress, etc. and she put makeup on me. When we went out trick-or-treating, we went to neighbors who we knew and they all asked who was the cute girl...haha. I don't know if my mom prepped them or if they really thought I was a girl. At age 7 or 8, I'm sure I did look like a girl!

 

[Ghg789987]

Has anyone ever been dressed up all girly with or by you sister before? I almost got to wear some of my older sister’s clothes by her when I was younger but I chickened out and refused to dress up like a girl.

Yes! while playing truth or dare, I chose dare, then my sister dared me to wear her panties. It was my first time, I loved it. I asked her to let me wear them the rest of the day, she allowed it.

 

[Angelapinks]

Yes! while playing truth or dare, I chose dare, then my sister dared me to wear her panties. It was my first time, I loved it. I asked her to let me wear them the rest of the day, she allowed it.

I dressed in my sisters clothes one Halloween when I was about 12 and we went around the area for about an hour. Not sure if anyone we knew guessed who I was but I loved the whole night wearing her panties, tights and dress.

 

[LittleJ123]

I don't currently consider myself to be a sissy or anything. However, I did have an experience like this when I was younger. I was about 4 or 5 years old, and my older sister had this yellow dress that I really liked. It had frilly edges and yellow flowers on it. She put it on me a few times and I loved the freedom of movement for my legs. Something about being in the dress made me feel more emotionally expressive. I was giggly and happy. Eventually, my mom said that enough was enough. She wasn't stern about it, and didn't really explain why. She just said that I should wear my clothes, and my sister should wear her clothes.

 

[Bhuna71]

My sister is 2 1/2 years older than me, so her clothes fitted me fairly well and I "borrowed" them quite often. Only in secret, though; she never dressed me in them or (as far as I know) knew I was wearing them.
On one occasion when I think I was about 7 or 8, I lost a game to her and her friend, and they told me that as a forfeit I had to put on my sister's dance outfit for them: a maroon velvet leotard with a high neck and a zip up the back, and a pink net tutu skirt. Being "forced" to wear that kind of thing for the amusement of two women is very much the stuff of my fantasies now, but at the time I was too embarrassed and I refused. I sometimes wonder what might have happened if I had agreed. Would my sister and her friend have realised how much I liked wearing girly clothes, and would it have become a regular thing for them to dress me up in their clothes? Would it have become "normal" in my mind, and would I now still enjoy the delicious humiliation of being sissified and emasculated?

 

[Angelapinks]

My sister is 2 1/2 years older than me, so her clothes fitted me fairly well and I "borrowed" them quite often. Only in secret, though; she never dressed me in them or (as far as I know) knew I was wearing them.
On one occasion when I think I was about 7 or 8, I lost a game to her and her friend, and they told me that as a forfeit I had to put on my sister's dance outfit for them: a maroon velvet leotard with a high neck and a zip up the back, and a pink net tutu skirt. Being "forced" to wear that kind of thing for the amusement of two women is very much the stuff of my fantasies now, but at the time I was too embarrassed and I refused. I sometimes wonder what might have happened if I had agreed. Would my sister and her friend have realised how much I liked wearing girly clothes, and would it have become a regular thing for them to dress me up in their clothes? Would it have become "normal" in my mind, and would I now still enjoy the delicious humiliation of being sissified and emasculated?

Those are questions for the Universe but I have often wondered the same thing. If mum did not insist I wear my sisters tights to keep me warm in the Canadian Winter, would I have ever tried them on myself? The same with my plastic pants fetish, if our friend had not insisted we put on his brothers plastic pants for the afternoon would I have ever discovered my love for them and all things plastic? The thought of ever being caught was always on my mind and added to the excitement.

 

[AnalogRTO]

With dressing up in my teens supported and encouraged by my mother, there were multiple times I was dressed up around my sister. One that I do remember was when my mother and stepfather wanted to get a professional family photo taken. Mom was telling us that we were going to have the photo session and that my stepfather would be wearing his suit and she wanted to go out and get matching dresses for her and all the girls. I remember asking what I was going to wear when mom just reiterated that all the girls would be wearing matching dresses.

I got the hint.

 

[Lickingatallsorts]

This is probably one of my earliest semi sexual experiences. I didn't have a sister but my friend did. It was fairly common we would end up staying at each others houses at the weekend.

We would be roughly 10 and his sister 1 year younger. We ended up playing this game where all 3 of us had to remove all our clothes and put them in the middle of the room where they were all mixed up. We would then dance until one of us shouted stop. The winner was whoever had the most of somebody elses clothes on. I made a beeline for her stuff.

 

[PinkyJujubean]

I used to play dress up with my sister all the time. She's always been my bestie and we're so much alike that it's crazy.

 

[Sissyleslie]

I have an older sister, but we never played "dress-up" together. However, when she got married and moved out, I did try on some of her old clothes. It was whilst wearing an old 'Bardot' dress of hers that I discovered the joy of wearing women's clothing, for which I am eternally grateful.

 

[sbmccue]

I didn't have a big sister, but I certainly enjoyed reading the responses from those who did. Thanks to the OP.

 

[BuddyBoy]

Has anyone ever been dressed up all girly with or by you sister before? I almost got to wear some of my older sister’s clothes by her when I was younger but I chickened out and refused to dress up like a girl.

I am an olny child, Christian. But I preferred to play with girls and had a "girlfriend" who encouraged me to try on her dresses when we played dolls together. I remember feeling better when I did, like being "dressed for the part".

 

[FCiara]

Unfortunately, my only sister was 5 years younger than me so her clothes didn't fit me. I had to content myself with my mother's clothes.

However, there was one one-piece yellow swimsuit that I was able to put on. It was tight but not too bad. I played in the bathtub for a little while before talking it off.

I had a swimsuit too and bikini but from my 10-12 year old sister, who was 6 years older than me. As I got her age I wore it.

 

[diane]

Has anyone ever been dressed up all girly with or by you sister before? I almost got to wear some of my older sister’s clothes by her when I was younger but I chickened out and refused to dress up like a girl.

i did when i was 11 sister was 14 she dressed me up so i could go to mall with herive never felt the same since that day i really should have been a girl

 

[BuddyBoy]

i did when i was 11 sister was 14 she dressed me up so i could go to mall with herive never felt the same since that day i really should have been a girl

We live and we discover selves we did not know.

 

[Cottontail]

My sister is two years younger. We never dressed each other up, but we several times dressed up in our parents’ clothes while they were away. I think on those occasions I mostly wore Dad’s stuff, but I can remember wearing Mom’s heels and finding them extremely uncomfortable!

 

[Manzanita]

A few times by my older sister's. There was one time I remembered vividly, I was hanging out with sisters in their room, one of my sisters had a Disney Alice costume and I remembered getting dressed up in it, then we heard our mom walking towards the room and my sisters hid me in the closet, I could hear my mom and sisters talking while I was in the closet, my mom thought I was in my room sleeping not being dressed up in a dress and a petticoat hiding in a closet. My mom left the room and my sisters and I continued playing quietly. I was like 5 or 6 at the time, 2002 or 2003.

 

[Ali123]

The first time I ever wore girls’ clothes was when I was put into a pair of my sister’s knickers for a spanking.

Lucy is two years younger than me, so it was terribly embarrassing.

 

[goodniteswearer89]

I never got to cause I didn’t have an older sister I was the oldest sibling. I do have a younger sister but never dressed up as a girl around her. I did however borrow some of her clothes like a Jean skirt and some of her panties and a bra and one of her bikinis. She never found out about it though