How did crossdressing start with you all?

[ozzy4605]

so your sister could steal underwear from you then ...

Nope she never did steel underwear from me, if she ever needed a pear she would just ask if she could borrow one from me

 

[LucyMarie]

Started when I was about 12 and my young Auntie did my make up and made me look so pretty. My mom and dad went ballistic and I had to remove it right away. Then about 6 months after that, my next door neighbour [shared garden] dropped a pair od tiny panties from her laundry basket. I picked them up and wore them the same afternoon. I was so turned on but didn't know what that was about at that time. Move on 20 year and my ex got me a maids outfit from Birchplace to spice up our sex life. It blossomed from there. I've a wardrobe full pf pretty dresses and a knicker drawer most women would die for I'm now single and never mastered the make up and certainly couldn't be passable as a girl/woman but I wear dresses as soon as I reach home and always sleep in a nighty. I just love how girly I feel inside even if I don't look as pretty.

 

[AnalogRTO]

Same here, that was until she found out and told our mum, i didn't get into trouble over it, i just come home from school one day, and found my underwear draw was filled with girls underwear, not a pear of boys underwear to be found, except for the pear i was wearing, i never found out if it was my mums or my sisters idea to replace my boys underwear with girls underwear, my sister was much happyer and i think she was thinking of more ways to get more girls clothing into my everyday wear, and my sister is 1 year younger then me, my youngest sister was born 2 months after this happened, making her 7 years younger then me, and when my youngest sister was 6 we would play dressup with her clothing, and yes i could and did fit into her clothes, when we would play dressup my youngest sister, would have me wear her primary school uniform dress witch i liked to wear, and if she had a frend stay over for the weekend and we played dressup, my youngest sister would have me wear her frends primary school uniform dress, and her frends underwear that she had worn with her primary school uniform dress that day, and later on in the day i got to wear the rest of her frends clothing, that i liked better then wearing my sisters clothing when she had frends stay over, this went on until my youngest sister was about 10 years old, and her primary school changed there girls school uniform from the old uniform dress to a more bland red polo shirt and a black skirt, thats wear the dressup time with her and her frends ended. :-(

Did that take much getting used to? When I first got dressed by mom and then she bought me my own clothes, it took a while for me to get used to the fact that I would open my underwear drawer to find boy's briefs on one side, panties and bras on the other. Or to open my closet and see dresses and skirts hanging there.

My sister and I really didn't borrow each other's clothes, I was a fair bit taller than she was so sizes weren't the same. My stepsisters didn't have as much clothing around since they split time between our house and their mom's place so there wasn't much chance there to share either.

Apparently my stepfather was more than happy to have me as a girl, he felt there were too many problems with me being the 'odd one out' and with all four of us kids being girls it kept there from being as many issues between us.

 

[MikeRotch]

i was around 6 or 7 and my foster parents were lesbians and they would dress me up in my sister clothes and make me dance in front of their guy friends. and ever since then id take my sisters clothes and secretly use them growing up, but then they moved out and im stuck at home living with my bilogical mother... if memory serves me right, my 1st time crossdressing i was in pink panties, a white skirt and light blue shirt with pink flowers on it.

 

[MikeRotch]

i was around 6 or 7 and my foster parents were lesbians and they would dress me up in my sister clothes and make me dance in front of their guy friends. and ever since then id take my sisters clothes and secretly use them growing up, but then they moved out and im stuck at home living with my bilogical mother... if memory serves me right, my 1st time crossdressing i was in pink panties, a white skirt and light blue shirt with pink flowers on it.

also im a middle child one older sis and a younger sis. and a single mother, didn't have to much of a father figure, there were guys that would be around the house and well. maybe the rest will go into stories.

 

[GabyinPurple]

My sister is 1 year younger then me, and no she never corte me, but i did catch her in my clothes twice, once wen she had a frend sleep over, her frend daird her to wear my clothes, then my sister daird me to wear her frends clothes i did wear them, it was what my sisters frend was wearing at the time, me and my sisters frend went into the bathroom to change clothes, just took all our clothes off and we were standing in our underwear, and i sayd i think we should go all the way as we have come this far and she sayd ok, there we were both naked, i think i sayd you look nice or something like that, then we got dressed, my sisters frend put my underwear, shorts and tee shirt on, then she helped me get her underwear on, and then it was her white care bears button up top and her pastel pink care bears shortalls on, then it was out to show my sister, she was stuned that we looked like twins, we stayed like that for over 2 or more hours then we changed back into our own clothes with one exception, i kept her underwear on and my sisters frend kept my underwear on, then the second time i corte my sister wearing my clothes was, when the washing machine broke and she ran out of clean everyday clothes, i let her off that time.



This is something like the shortalls my sisters frend was wearing at that time, hers had the care bears on them,
not the care bear cousins like these have on them, but you get the idea.

Care bear Official dungaree shorties

S$85 | Tag says size Medium; fits UK10-12, IMO. For the young at heart.. adulting is tough isnt it? LOL!

www.carousell.sg

Now that sounds like an adventure I never got to experience with any of my sisters or their friends.

 

[Pantyslave]

I was in my mid to late teens and staying with my Auntie.
Walking past her open bedroom door, I saw a pair of her white silky panties lying on the floor. I picked them up and had a fabulous afternoon wearing them and posing in front of the mirror.When I tired of that, I pulled them over my head.
I was a Pantyslave from that day on.

 

[ozzy4605]

Now that sounds like an adventure I never got to experience with any of my sisters or their friends.

@GabyinPurple the next time that friend of my sisters stayed over, i got to wear here primary school uniform dress, and she had a bag of some of her old clothing for me to keep except, 1 shirt, 1 pear of shorts, 1 skirt and a pink and blue 1 peace swimsuit, was to go to my sister and i got to keep the rest of my sisters friends old clothing, there was some new clothes in the bag for me as well, i just thanked thanked her for the clothing, then she sayd that she had got the same clothes for her, my sister and me, so we could all pretend to be triplets, that was a fun 2 weeks of ester school holidays, that was such a fun time, then we all got together age later on in life and we were talking about what we did back in the late 1980's early 1990's, and my sisters friend sayd that she had a crush on me back then, and was to afraid to tell me or my sister, thats why i got all her old clothes, it was her way of saying that she liked me, if i had of picked up on it, then things could have been much different, but i was to slow to notice it and ask her, and she was to scared to tell me how she felt about me, we only found this out wen we all got back together in 2018, now we are all best friends, and the best thing i found out that my sisters friend lives in the same town as me, and she is living only 2 hours away from me on the south side of the town.

 

[GabyinPurple]

@GabyinPurple the next time that friend of my sisters stayed over, i got to wear here primary school uniform dress, and she had a bag of some of her old clothing for me to keep except, 1 shirt, 1 pear of shorts, 1 skirt and a pink and blue 1 peace swimsuit, was to go to my sister and i got to keep the rest of my sisters friends old clothing, there was some new clothes in the bag for me as well, i just thanked thanked her for the clothing, then she sayd that she had got the same clothes for her, my sister and me, so we could all pretend to be triplets, that was a fun 2 weeks of ester school holidays, that was such a fun time, then we all got together age later on in life and we were talking about what we did back in the late 1980's early 1990's, and my sisters friend sayd that she had a crush on me back then, and was to afraid to tell me or my sister, thats why i got all her old clothes, it was her way of saying that she liked me, if i had of picked up on it, then things could have been much different, but i was to slow to notice it and ask her, and she was to scared to tell me how wishe felt about me, we only found this out wen we all got back together in 2018, now we are all best friends, and the best thing i found out that my work lsisters friend lives in the same town as me, and she is living only 2 hours away from me on the south side of the town.

Now that’s a situation that a lot of us would love to wander back into. Having moved so much growing up I never had the opportunity to reconnect with anyone from youth like that to find out if anyone had a crush on me or had an interest for dressing or diapers.

 

[BonsaiBoy]

I wouldn’t exactly call myself a crossdresser, but there was a phase during my mid to late teens were I wore girl’s panties. It all started when I moved into an aunt and uncles house and had to share a room with my cousin. Not long after my aunt commented on the condition of my underwear as she put my clothes on my bed, after she had done the washing.

Without actually saying it she alluded to suspecting I was still pooping in my underwear. That was enough for my cousin to work out what she meant, and it completely fascinated her. She insisted on knowing, and I eventually admitted to doing it. After that she kept checking my underwear when I got home and every opportunity she got.

I only had about 15 underwear, all of which had clear evidence of being pooped in multiple times and that also fascinated my cousin. My aunt made it clear she wasn’t going to buy me more underwear, so my cousin suggested I could wear hers. Not only did she suggest it she literally insisted on it by telling me she could tell everyone what I did in my underwear.

My first reaction was to say no, but she insisted so I put the ones on she had given me. When I did, I was amazed how nice they felt and how good they looked, compared to my boring boys undies. They were yellow with a picture of a kitten on the front and were actually the ones she had worn the day before.

Wearing them to school that day was an extremely nerve-racking experience, but also very arousing. When I got home that afternoon, she checked I was still wearing them the moment I got home, but was disappointed I hadn’t pooped in them during the day. After that I wore her panties almost every day and although I stopped once I moved out, I still do from time to time.

She also, insisted I wore one of her night dresses which was far too short for me, and she often put make-up on me. That was actually fun, except the day some of my friends came around to see me. They knew I shared a room with her and how “controlling” she was but that didn’t stop them from making fun of me for quite a while after.

a cute story. I am sure that I would have refused and then would have accepted the force. (and I would have loved it...)

 

[Airborne532]

a cute story. I am sure that I would have refused and then would have accepted the force. (and I would have loved it...)

Before I moved in sharing a room with a very controlling younger cousin, seemed like a terrible idea. I soon changed my mind, and she was completely fascinated with me, which she didn’t bother hiding at all. She would even tell my friends to leave when she thought they had been there long enough. That amused them and they were always making fun of me at school when she wasn’t around.

One of them might have even known I wore her panties and what I often did in mine. He regularly made comments and I think he might have been a little jealous. The other interesting experience sharing a room with her was her bed wetting, which she did pretty much every night. The very first night she insisted on sleeping in my bed, which I objected to knowing she wet her bed.

My aunt made it clear it was her room and she could sleep where she wanted to. I soon changed my mind after the very first night when she peed all over me. She wrapped her arms and legs around me like she thought I was going to escape during the night. When she started peeing, I immediately work up shocked, but quickly changed my mind. I think my friend was a little jealous of that as well, as he would often ask me questions.

 

[BonsaiBoy]

When I was about 12 I started wearing my older sisters knickers, bras, skirts etc knickers are just so much better than boxer shorts

I was brought up with brothers and one sister. I loved to touch and feel her clothes, esp. underwear. I also got into my moms drawers, huge underwear, very silky. But I never had "boxer shorts". they were no fashion around us in the sixties and seventies. Only when I was old, really old, I dared put on knickers under my working attire. Who could tell that under my business suit I had pantyhose and panties....

 

[diane]

started in sisters when 11 she was 14 i felt so good and safe in them

 

[MichelleM39]

I guess it started when I was young. My mother had a weird sense of humor, I remember when she would brush my hair in front of the bathroom mirror and suddenly she'd notice that my hair was getting too long in the very back. She would grab up that hair and threaten to turn it into a ponytail and make me become a girl. I would feel shocked and try to run away. But the truth was that her "joke" of turning me into a girl was always very exciting and it put a grin on my face.

When I reached puberty, I watched erotic movies and identified with the female characters. If you are middle aged like me, you might remember those old softcore Euro erotic movies of the 1970's and 1980's. Those movies featured so many female maid characters who were very submissive. I especially loved the job role of hotel maids. By the time I was 15, I secretly wanted to work as a sissy hotel maid when I grew up.

When I was 18, I started wearing pantyhose, slips, and nightgowns. I had found TG stories online and began to think of myself as a "Sissy".

 

[Fireball44]

I guess it started when I was young. My mother had a weird sense of humor, I remember when she would brush my hair in front of the bathroom mirror and suddenly she'd notice that my hair was getting too long in the very back. She would grab up that hair and threaten to turn it into a ponytail and make me become a girl. I would feel shocked and try to run away. But the truth was that her "joke" of turning me into a girl was always very exciting and it put a grin on my face.

When I reached puberty, I watched erotic movies and identified with the female characters. If you are middle aged like me, you might remember those old softcore Euro erotic movies of the 1970's and 1980's. Those movies featured so many female maid characters who were very submissive. I especially loved the job role of hotel maids. By the time I was 15, I secretly wanted to work as a sissy hotel maid when I grew up.

When I was 18, I started wearing pantyhose, slips, and nightgowns. I had found TG stories online and began to think of myself as a "Sissy".

been wearing diapers and pantyhose over 40 years, love being a girl and a boy, never knowing what tommorrow bringsme.

 

[goodniteswearer89]

I started cross dressing when I was around 14 I would take some of my younger sister’s clothes mainly her bras or panties or a skirt. I would also occasionally take her bikini tops and bottoms and wear them occasionally. I liked how they felt and how easily I could rub myself down there and how it felt to secretly wear them even though I wasn’t supposed to. To this day I will occasionally wear some of my girlfriend’s panties.

 

[1baby]

So how are you today you big baby girl?

 

[GabyinPurple]

I guess it started when I was young. My mother had a weird sense of humor, I remember when she would brush my hair in front of the bathroom mirror and suddenly she'd notice that my hair was getting too long in the very back. She would grab up that hair and threaten to turn it into a ponytail and make me become a girl. I would feel shocked and try to run away. But the truth was that her "joke" of turning me into a girl was always very exciting and it put a grin on my face.

When I reached puberty, I watched erotic movies and identified with the female characters. If you are middle aged like me, you might remember those old softcore Euro erotic movies of the 1970's and 1980's. Those movies featured so many female maid characters who were very submissive. I especially loved the job role of hotel maids. By the time I was 15, I secretly wanted to work as a sissy hotel maid when I grew up.

When I was 18, I started wearing pantyhose, slips, and nightgowns. I had found TG stories online and began to think of myself as a "Sissy".

Okay but did you ever get the hotel maid job?

 

[Deleted member 77157]

It was the thrill of being different when I picked out some of my first diapers, I decided to try the girl ones because they looked more babyish and cuter and I felt so happy for that , that eventually spread to other cross dressing and after playing with it with my OC drawing them in situations I found out about otokonoko and was hooked

 

[Pantysnpullups]

I had wanted to wear girls clothes for awhile. I was always jealous of girls in school with bright colors, glitter, and cute outfits. Boy stuff was always plain and boring.

My crossdressing actually started with a friend. It was the summer before 7th grade and his twin sister was away at camp. And his parents were at work all day so we stayed at his house and played videogames. I asked him nervously "do you ever wear your sisters clothes?" And he said "no...why would i?" But I could tell he was nervous too. So I continued, "don't you want to know how a skirt feels...or bras...or how panties fit?"

After a moment he looked up an replied "ya....I thought I was the only one..." almost ashamed. I said "me too...I thought I was the only guy who wanted to wear girly stuff".

We sat for another moment before he got up and said "....well...should we...." and we both silently with nervous excitement wandered into her room.

It was exactly what you'd picture a room as. Boy band posters on the wall, absolutely spotless, and pink purple and light blue everything (bedding, wall paper etc) ..

He opened the middle 2 drawers of her dresser and I pulled out a plaid skirt. And he put on one of her neon yellow shirts that said "certified princess " in pink glitter letters. We continued to dig through the drawers playfully daring each other to wear more and more (dresses, hair clips, shoes etc).

Then we opened the top drawer and both froze. It was her underwear drawer. We were met with an absolute mountain of panties and over a dozen training bras. We were both so nervous. We promised we would never tell anyone. We closed are eyes and each picked a bra and panties then went to opposite sides of the room and put them on. They felt absolutely amazing! Like electricity. My bra was a pullover style. Light pink with green straps and little silver stars on the cups. My panties were orange with cartoon cats wearing sunglasses and surfboards. Both fit incredibly well and I fell in love instantly.

My friend had a white bra with little yellow bows where the straps met the cups and panties with Cinderella and glass slippers all over them. We met in the middle of the room and admired ourselves and each other in them .


We repeated this the rest of the week. I eventually told his sister a few months later (just that I didn't I didn't tell her her brother was too) and to my surprise she made me dress in a complete outfit (panties bra, skirt crop top etc) she seemed delighted