Ever dressed up with sister?

[KittyninjaW]

Sadly, I've never had a sister. I think if I did though I may have been more comfortable to explore my gender earlier. Sadly, I never got a sister though. It took me years to accept that I am actually a girl.

Same but I never had any older sisters. I had a younger sister from my stepmother that I used to play with her Barbies but no older sisters. I wish I had a older sister though.

 

[Ali123]

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

Are you sure she never found out? Maybe she just never said anything because she liked the idea of her big brother wearing her clothes?

 

[Pantyslave]

Strangely enough, no, although there must have been plenty of opportunities.
I always sneaked my Aunties panties and a couple of times my 2 cousins swimsuits. They both fitted me but I preferred my youngest cousins swimsuit as it was a bit tighter .
I usually retrieved them from the laundry basket although once I went through my Auntie's panty drawer when she was out. I can stil remember that heart-in-mouth feeling as I carefully touched those beguiling items of satin, silk and cotton with their lace, frills and bows.

 

[goodniteswearer89]

Are you sure she never found out? Maybe she just never said anything because she liked the idea of her big brother wearing her clothes?

I’m pretty sure she didn’t cause I think she probably would have said something to our mom. I also think she might have been freaked out if she would have found out.

 

[Pantysnpullups]

My neighbor dressed me in an outfit one time in middle school. I confessed to her that I wore her clothes one day while she was away at camp. She seemed intrigued and delighted and picked out an outfit.


Another time. I was caught by my younger sister in a pair of her panties. She giggled and said "those look to small for you" which they were.

And my cousin caught me in one of her old training bras once. She was annoyed and forced me to wear it every time we were together at her mom's house that summer.

 

[Angelapinks]

My neighbor dressed me in an outfit one time in middle school. I confessed to her that I wore her clothes one day while she was away at camp. She seemed intrigued and delighted and picked out an outfit.


Another time. I was caught by my younger sister in a pair of her panties. She giggled and said "those look to small for you" which they were.

And my cousin caught me in one of her old training bras once. She was annoyed and forced me to wear it every time we were together at her mom's house that summer.

Was your neighbor the same age as you and your cousin also or were they older than you. I can't ever remember being caught by my sister or parents but mum did find my girls clothes more than once. My father was very upset that I was hanging around with all the neighbor girls but never directly asked me why.

 

[Pantysnpullups]

Was your neighbor the same age as you and your cousin also or were they older than you. I can't ever remember being caught by my sister or parents but mum did find my girls clothes more than once. My father was very upset that I was hanging around with all the neighbor girls but never directly asked me why.

My neighbors were twins (a boy and girl) the same age as me.

Sister is younger. As she grew up her wardrobe got more plain and boring

Cousin is2 years younger. She went through phases. Girly girl, "juicy couture " teen to "professional " in college. So there were lots of options throughout the year.

Caught me in one of her middle school training bras when we were in high school. Wasn't mad...more annoyed (and I think a bit embarrassed because she couldn't even fit in it anymore) but she made me wear it all summer....probably 15-20 times....for up to 24 hours each time

 

[goodniteswearer89]

My neighbors were twins (a boy and girl) the same age as me.

Sister is younger. As she grew up her wardrobe got more plain and boring

Cousin is2 years younger. She went through phases. Girly girl, "juicy couture " teen to "professional " in college. So there were lots of options throughout the year.

Caught me in one of her middle school training bras when we were in high school. Wasn't mad...more annoyed (and I think a bit embarrassed because she couldn't even fit in it anymore) but she made me wear it all summer....probably 15-20 times....for up to 24 hours each time

The last part of that where she caught you with her training bra is something I have fantasized about for a while especially when I was younger I had a few fantasies about my cousin that is a year older than me catching me wearing some of her stuff like her bra or her panties and then next time we were alone her making me wear some of her panties and maybe even her bra and then her seeing me get hard and her helping me out.

 

[Ali123]

The last part of that where she caught you with her training bra is something I have fantasized about for a while especially when I was younger I had a few fantasies about my cousin that is a year older than me catching me wearing some of her stuff like her bra or her panties and then next time we were alone her making me wear some of her panties and maybe even her bra and then her seeing me get hard and her helping me out.

Being caught wearing a bra must be exquisitely humiliating, There's really no explanation possible, and you're at their complete mercy.

 

[Stephlau2000]

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.

No but looking back I think I could shave as she would have liked to take control of me and humiliate me so I should have investigated it.
This is where it all started for me as I have shared before in previous posts, my parents and sister went out for the afternoon and I tried on her training bra, panties, school dress, tights and t-bar shoes and never looked back
Steph

 

[BuddyBoy]

No but looking back I think I could shave as she would have liked to take control of me and humiliate me so I should have investigated it.
This is where it all started for me as I have shared before in previous posts, my parents and sister went out for the afternoon and I tried on her training bra, panties, school dress, tights and t-bar shoes and never looked back
Steph

A boy who allows himself to be dressed by his sister in her clothes has surrendered his masculinity to her. After that he needs very little discipline; the clothes do it all. After the initial self-consciousness passes he finds he is more content that he has ever been.

 

[babybev]

I started sneaking into my older sister's room and taking stuff when I was 4 and she was in 2nd grade. I loved the petticoats and pretty panties and would take them back to my room and wear them while she was at school. She found out and told Mom who thought it was cute. So when my sister got a cowgirl outfit Mom bought an identical one for me. We loved dressing up in them and playing around the yard and riding our ponies. We did this until she outgrew hers, then she handed it down to me so I could keep dressing up like a cowgirl.
We rode our ponies in our small town's parade each year. One year sis and Mom dressed me as a bareback rider in a gold dress, tights, and scarf over my short hair. I was really embarrassed riding through town dress in front of all the people, but secretly loved it as well.
As we got older my sister would babysit me and we would play dress up the whole time our parents were out. She would curl my hair and put make-up on me, then dress me in her pretty dresses. This continued until she went off to college. She left me many outfits and underwear when she left. After she got married she left her wedding dress back in her old room and told me to "enjoy myself". I wore it many times until I could no longer fit in it.
Growing up I had a great life.

 

[jamie72]

Not my sister, but I used to often stay at my cousins - when I was about 7 I had gone there and was staying the weekend - unfortunately I had an accident and peed my pants - with no spare clothes I had to borrow some of my female cousins clothes - she was about the same age as me.
So I ended up in girls pants and vest, socks and shirts and tee shirt - at nightime I chose to wear one of her nighties instead of my pj’s - really liked it - and played with my cousin like a little girl - the next day I wore one of her skirts and was a girl for the weekend.
After that everytime I stayed I would wear her clothes, even played outside - her friends thought I was her girl cousin

 

[Ali123]

Not my sister, but I used to often stay at my cousins - when I was about 7 I had gone there and was staying the weekend - unfortunately I had an accident and peed my pants - with no spare clothes I had to borrow some of my female cousins clothes - she was about the same age as me.
So I ended up in girls pants and vest, socks and shirts and tee shirt - at nightime I chose to wear one of her nighties instead of my pj’s - really liked it - and played with my cousin like a little girl - the next day I wore one of her skirts and was a girl for the weekend.
After that everytime I stayed I would wear her clothes, even played outside - her friends thought I was her girl cousin

You were lucky you weren't put back into nappies if you peed your pants.

 

[BabyHailey1977]

I’m pretty sure she didn’t cause I think she probably would have said something to our mom. I also think she might have been freaked out if she would have found out.

I had an older and a younger sister. I used to wear both of their clothes. A couple years ago I opened up to my older sister about stealing her clothes and she said she always blamed our younger sister and she always denied it. She said girls always know when someone has been in their clothes. I tried so hard to be stealth, but yeah. I’m sure your sister knew something was off.

 

[JazzBaby]

No, I never did with my sister, as far as I know. Even though I was always small growing up and was like a living doll, I think it mostly had to do with our nearly 10-year age gap. Maybe if we had been closer in age, she would have dressed me up in some girly doll clothes. I'd like to have to be dressed as a girl in cute frilly dresses.

 

[1baby]

This is how it all began for me. I dressed up with both my younger sisters until I turned 10 years old. I remember it was my first time trying on girls clothes. i was around 8 years old and I had wondered for a while what it would be like to wear a skirt or dress They were playing dress ups one day and I wanted to play as well. They were a bit surprised when I asked if i could join in and with that of my sisters handed me one of her netball skirts to try on. I remember it like it was yesterday. I was so nervous and excited so she helped me by wrapping it around my waist over my shorts and fastened it on. She said it looked silly with it on over my shorts and with out a second thought I took my shorts off right there and the rest is history. It was my first time ever in a skirt and I loved how it felt. Over the next couple of years I played dress ups with them now and then with various skirts and dresses of theirs. I just loved how comfortable the clothes were and how lucky they were to be girls. The dress up games stopped after I turned 10 years old and that is when the dressing in their clothes in secrete started.

 

[Lilschoolfox]

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 wore my sister school uniform she wore mine

 

[Ali123]

This is how it all began for me. I dressed up with both my younger sisters until I turned 10 years old. I remember it was my first time trying on girls clothes. i was around 8 years old and I had wondered for a while what it would be like to wear a skirt or dress They were playing dress ups one day and I wanted to play as well. They were a bit surprised when I asked if i could join in and with that of my sisters handed me one of her netball skirts to try on. I remember it like it was yesterday. I was so nervous and excited so she helped me by wrapping it around my waist over my shorts and fastened it on. She said it looked silly with it on over my shorts and with out a second thought I took my shorts off right there and the rest is history. It was my first time ever in a skirt and I loved how it felt. Over the next couple of years I played dress ups with them now and then with various skirts and dresses of theirs. I just loved how comfortable the clothes were and how lucky they were to be girls. The dress up games stopped after I turned 10 years old and that is when the dressing in their clothes in secrete started.

What a shame your little sister didn’t hand you a pair of her knickers to put on under your little skirt.

 

[daisycupcake]

I played dress up with my cousin until she left for uni