How did crossdressing start with you all?

[Angelapinks]

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

WOW lucky you. I had a girl friend who I took Figure Skating lessons with. Each time at the Arena she could see I was freezing so the next time at her house she gave me some beige skating tights and white cotton bloomer style panties. She said I would be warmer wearing them under my clothes and I was. When skating was over I asked if I could keep them but she gave me a funny look so I gave them back to her and went and bought my own. Been wearing panties and tights ever since.

 

[pissypants65]

Basically the title says it all. For me I always had the urge but never acted on it. I used to play with my younger sisters dolls with her and in private back when I was still living with her, I once attempted to build a Tea Set with Legos and was envious of girls toys and stuff like that. Also after my fantasies activated at around middle school/ high school they started getting more intense when I started reading stories about diapers and crossdressing. Later I went on Adisc I started acting on it and I loved it.

mine started after meeting a man in his 50,s in a cottage he introduced me to fully dressing not just panties , w/s diapers and role play . wish i could meet someone like him now

 

[BonsaiBoy]

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

I always had that dream, that I could visit the neighbors with their 4 girls and that they would help me dress like a sweet girly. I was rather young the first time I roamed around in the drawers of my sister. Lately I have found that some shops for second hand stuff actually maintains a little box with underwear in a corner. It is bit embarrasing to hunch down and grope a few and hurry to the exit to pay and come home and try them. Some are really cute, but I have not time to make a selection, really.

 

[BonsaiBoy]

WOW lucky you. I had a girl friend who I took Figure Skating lessons with. Each time at the Arena she could see I was freezing so the next time at her house she gave me some beige skating tights and white cotton bloomer style panties. She said I would be warmer wearing them under my clothes and I was. When skating was over I asked if I could keep them but she gave me a funny look so I gave them back to her and went and bought my own. Been wearing panties and tights ever since.

I found some thick thights. They could of course be used for a male, but the dimensions a purely female. I love them.

 

[BonsaiBoy]

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.

soon enough you can dress like you wish. Next time you go shopping, pretend they undies are a gift to your girlfriend. No one will question your choice. it takes some courage, though. I wish you good luck and looks.

 

[Diapersntights]

The roots go back deeper, but wearing started when I was about 14, when my mum threw out a pair of tights in the bin in my bedroom because she didn't have a bin in her room. I came back home from school, had the house to myself, tried them on and they didn't disappoint! Have loved tights ever since.
The history with me and tights goes back to starting primary school and having to go on cold days from the class room outside to the hall for gym. Us boys would be freezing in our shorts and t-shirts, while the girls would keep their tights on under their shorts or skirts - as a result they were warmer and happier, so I've always associated women in tights with being happy.
A couple of years later I was sitting next to a girl who desperately needed to go to the toilet, she asked to be excused, but the teacher said it was a crucial part of the lesson and asked her to hold on. We were all gathered standing round a desk watching something be demonstrated and the girl was really struggling, started walking on the spot and then almost running on the spot before the inevitable happened, spectacularly and with considerable force - the fountain of wee through her thick cableknit tights had an immediate impression on me - I didn't get splashed or anything, but remember thinking it must have been her tights that caused her wetting to be different from the usual previous occasions where it just dribbled down either leg in to a shoe and sock and on to the floor.
Another year or so later the kid who lived a couple of doors away from me announced he had a superman outfit, I'd seen ones where the leggings were like pyjama bottoms, but his were actual proper tights - I was intrigued - tights had been the forbidden fruit and stayed that way until I was around 14, but in the years in between they became ever-more fascinating. Everything else cross-dressing followed from there.
I thought that was it until a few years ago when I got in to nappies - watching porn with women squirting, which was often weeing, from there found wetting and diapers. I got more inquisitive, eventually tried some and found something that I'd been looking for for years - I loved the feeling of having the padding between my legs keeping me secure (even better combined with tights) and then I remembered that when I was just out of toddler years (about 4), there was still a supply of nappies in my bedroom, just in case. I never needed them again, but a few times tried them on, I couldn't get the tabs to work and stick, so got bored and put them back, but there was something about the feel of the nappies I was missing.
I always thought my tights fetish came first, then my nappies fetish - turns out I just just too longer to remember my nappy fetish.

 

[Airborne532]

The roots go back deeper, but wearing started when I was about 14, when my mum threw out a pair of tights in the bin in my bedroom because she didn't have a bin in her room. I came back home from school, had the house to myself, tried them on and they didn't disappoint! Have loved tights ever since.
The history with me and tights goes back to starting primary school and having to go on cold days from the class room outside to the hall for gym. Us boys would be freezing in our shorts and t-shirts, while the girls would keep their tights on under their shorts or skirts - as a result they were warmer and happier, so I've always associated women in tights with being happy.
A couple of years later I was sitting next to a girl who desperately needed to go to the toilet, she asked to be excused, but the teacher said it was a crucial part of the lesson and asked her to hold on. We were all gathered standing round a desk watching something be demonstrated and the girl was really struggling, started walking on the spot and then almost running on the spot before the inevitable happened, spectacularly and with considerable force - the fountain of wee through her thick cableknit tights had an immediate impression on me - I didn't get splashed or anything, but remember thinking it must have been her tights that caused her wetting to be different from the usual previous occasions where it just dribbled down either leg in to a shoe and sock and on to the floor.
Another year or so later the kid who lived a couple of doors away from me announced he had a superman outfit, I'd seen ones where the leggings were like pyjama bottoms, but his were actual proper tights - I was intrigued - tights had been the forbidden fruit and stayed that way until I was around 14, but in the years in between they became ever-more fascinating. Everything else cross-dressing followed from there.
I thought that was it until a few years ago when I got in to nappies - watching porn with women squirting, which was often weeing, from there found wetting and diapers. I got more inquisitive, eventually tried some and found something that I'd been looking for for years - I loved the feeling of having the padding between my legs keeping me secure (even better combined with tights) and then I remembered that when I was just out of toddler years (about 4), there was still a supply of nappies in my bedroom, just in case. I never needed them again, but a few times tried them on, I couldn't get the tabs to work and stick, so got bored and put them back, but there was something about the feel of the nappies I was missing.
I always thought my tights fetish came first, then my nappies fetish - turns out I just just too longer to remember my nappy fetish.

Amazing experiences, especially the tights peeing. Maybe she didn’t have panties on under her tights.

During the last couple of years of high school, I shared a room with a cousin, that wet the bed just about every night. When I moved in, she started sleeping in my bed, which was a rather interesting experience. Every night she would go to sleep laying on me with her arms and legs wrapped around. She would literally go to sleep mid-conversation and sometimes talk in her sleep.

It was actually a little uncomfortable, but I didn’t mind at all. After a while I learned to know when she was going to pee and often watched. Probably sounds quite dirty but I liked the feeling of her peeing all over me and often lifted her up to direct the flow. I also rarely had a shower in the morning and sometimes had comments made during the day at school.

She usually wore panties, but they did little to slow the flow. When she didn’t wear them, it was amazing to watch unhindered. I also discovered a girl in my class wore something similar to pullups. She would quite freely let me take one of them, which was also amazing. For me it was the fact she had peed in it during the day, rather than the diaper itself.

Unfortunately, my cousin and her hated each other with a passion.

 

[BonsaiBoy]

Amazing experiences, especially the tights peeing. Maybe she didn’t have panties on under her tights.

During the last couple of years of high school, I shared a room with a cousin, that wet the bed just about every night. When I moved in, she started sleeping in my bed, which was a rather interesting experience. Every night she would go to sleep laying on me with her arms and legs wrapped around. She would literally go to sleep mid-conversation and sometimes talk in her sleep.

It was actually a little uncomfortable, but I didn’t mind at all. After a while I learned to know when she was going to pee and often watched. Probably sounds quite dirty but I liked the feeling of her peeing all over me and often lifted her up to direct the flow. I also rarely had a shower in the morning and sometimes had comments made during the day at school.

She usually wore panties, but they did little to slow the flow. When she didn’t wear them, it was amazing to watch unhindered. I also discovered a girl in my class wore something similar to pullups. She would quite freely let me take one of them, which was also amazing. For me it was the fact she had peed in it during the day, rather than the diaper itself.

Unfortunately, my cousin and her hated each other with a passion.

you seem to have a very good contact with those girls. Has that continued? I am just nozy. sorry. I have several friends that are girls/women, with no erotic connections. I wish I had those encounters.

 

[Airborne532]

you seem to have a very good contact with those girls. Has that continued? I am just nozy. sorry. I have several friends that are girls/women, with no erotic connections. I wish I had those encounters.

I continued to share her room for a couple of years after finishing high school. Mostly because she would get upset if she thought I was going to move out. A couple of the guys I was doing my apprenticeship with thought that was a good idea, and would sometimes say things when she was around. She didn’t like that idea at all and usually cried herself to sleep that night.

When I finally did it wasn’t far from her house, so she would come over quite a lot, she also slept over regularly. Having a cousin that was clearly fixated on me amused my friends, but being very pretty they didn’t mind having her around. The house we rented also had a pool, so she often wore her swimming uniform. My friends seemed to like that and would often suggest she go swimming.

I eventually moved away, but she still kept in contact and visits from time to time. For a while and until she found a boyfriend, she was still rather fixated with me and want to sleep in my bed. Virtually every time we meet now, she discusses what we used to do, and how she loved me much more than she should have.

The girl in my grade that wore diapers also came around to my house and she still wore diapers. We were never in a relationship, but starts sleeping together occasionally and only when my cousin wasn’t going to be there. I don’t recall her saying she liked wearing them, but I am sure she did. Like my cousin I learned to know when she was peeing and that was often in close proximately to a toilet. The other reason I am sure was it was often early, and she would continue to wear it.

 

[Diapersntights]

Amazing experiences, especially the tights peeing. Maybe she didn’t have panties on under her tights.

During the last couple of years of high school, I shared a room with a cousin, that wet the bed just about every night. When I moved in, she started sleeping in my bed, which was a rather interesting experience. Every night she would go to sleep laying on me with her arms and legs wrapped around. She would literally go to sleep mid-conversation and sometimes talk in her sleep.

It was actually a little uncomfortable, but I didn’t mind at all. After a while I learned to know when she was going to pee and often watched. Probably sounds quite dirty but I liked the feeling of her peeing all over me and often lifted her up to direct the flow. I also rarely had a shower in the morning and sometimes had comments made during the day at school.

She usually wore panties, but they did little to slow the flow. When she didn’t wear them, it was amazing to watch unhindered. I also discovered a girl in my class wore something similar to pullups. She would quite freely let me take one of them, which was also amazing. For me it was the fact she had peed in it during the day, rather than the diaper itself.

Unfortunately, my cousin and her hated each other with a passion.

Did the girl in your class pick up on the comments you were receiving at school and see you as an ally? If so, your cousin still did her a favour.

 

[Airborne532]

Did the girl in your class pick up on the comments you were receiving at school and see you as an ally? If so, your cousin still did her a favour.

They didn’t comment all that much, but vocal enough she would have heard. She was probably also familiar with the smell, being a pants or diaper wetter. I had discovered how good peeing in my pants felt a while before and I liked how it made me smell. My cousin and the girl in my class also liked it and often made comments to let me know.

The girl in my class offered me one of her diapers after she caught me checking. She was quite secretive about wearing them with other people and was with me for a while. Then one day while we waited for the bus, she very intentionally sat so I could see she was wearing one. That completely fascinated me, and I wondered what they would have been like inside.

I like the way my cousin panties looked after she had peed in them and they had dried out, especially when she wore one of her white panties. When I discovered the classmate wore diapers, I wanted to see what they looked like. Until then I had declined going to her house but the next time, she asked I agreed.

Curiosity eventually got to me, so I checked in the rubbish bin in her room. Instead of getting angry she told me I could have it with a comment something like, “you can have it if you want, I know you pee in your pants a lot”. She eventually discovered the other reason I often smelt like pee, the day she visited my house.

She must have heard about my cousin but didn’t believe it until that day, and it was clear she didn’t like the idea. When my cousin came in, she made it extremely obvious another girl in her room was not allowed. From that day on they hated each other.

 

[Fireball44]

WOW lucky you. I had a girl friend who I took Figure Skating lessons with. Each time at the Arena she could see I was freezing so the next time at her house she gave me some beige skating tights and white cotton bloomer style panties. She said I would be warmer wearing them under my clothes and I was. When skating was over I asked if I could keep them but she gave me a funny look so I gave them back to her and went and bought my own. Been wearing panties and tights ever since.

love the thicker denier and feel of skating tights. They will wear several years of fit , no runs, under a leotard.

 

[Angelapinks]

love the thicker denier and feel of skating tights. They will wear several years of fit , no runs, under a leotard.

I still have three pink leotards, one with a net skirt, one plain pink and one with a sequin heart motif on the front. I have had many over the years but only these three survive now, as I don't wear that often. As for tights well I have many but right now it is the fleece lined ones I wear almost everyday.

 

[MsSissyMissi]

My female neighbor had me dress up in her old maternity clothing looking like a pregnant teenaged tart on Halloween and I was escorted by her son who at first publicly embarrassed and humiliated me while we went door to door yelling trick or treat. When I started seriously thinking about it I realized that I enjoyed what he was doing to me which aroused me to the point later on when I was in their bathroom alone, that I had the biggest orgasm of my life. I tried wearing one of my mom's panty girdles but was caught and punished by her and my step father. It didn't stop my desire to crossdress and be the sissy girl that I was on the inside but since I wasn't able to crossdress during those teenage years I would take the big catalog book we kept in our house into my room secretly and then while looking through the pages I would fantasizing about being one of the models dressed in either one or many of the bra & panty set combos. This went on until I discovered Adult Magazines which led me to fantasizing about being the nude centerfold model which I believed at the time every woman wanted to be!!! After leaving home I went into the military and down through the years I bought, wore and threw away a good amount of lingerie on the DL of course and now years later I told four different women that I occasionally crossdress and half of them don't care and the other half don't really like it but accept me as I am.

 

[Littlebaby1999]

My fascination with cross-dressing began with a situation that took place when I was 12 years old. On vacation, we had a younger cousin who loved dresses and when she left, she forgot to pack one and stayed with us. My mother put it in the closet and a few days later I was looking for something in the closet and found it. I was so curious what I would look like in it and, during my mother's absence, I put it on for a while. I was her height, so it fit perfectly, and I had long, shoulder-length hair at the time (my mother fought to get me to go to the hairdresser, but I was stubborn and resisted it - puberty) I looked almost like a girl.

However, my mother came back sooner than I thought and I hurriedly ran to the bathroom. My mother realized that something was wrong and told me to open it immediately or risk being grounded for the entire vacation. Embarrassed, I opened the door for her and when she saw me in my cousin's dress, she was angry. She explained to me that boys are not allowed to wear dresses and for this behavior I deserved punishment. I listened to her embarrassed and after a while she told me to lie on her lap, which meant spanking me. After receiving a few slaps, I went to the corner with tears in my eyes as she ordered.

After some time in the corner, she called me to my room and told me to put on white tights, which embarrassed me even more. That wasn't the end, because she also took care of my hair. She combed them and made pigtails and used scissors to create eyebrow fringe.

When I looked in the mirror I was shocked. I looked like a 10-year-old girl in a pink dress and the embarrassment made me cry. I asked my mother to let me put on my clothes and she just said:"No way, as punishment you will wear a dress all weekend. And after the weekend you will definitely go to the hairdresser."

Fortunately, she didn't carry out her threat and I only wore the dress that day until the evening. And I regretted that I hadn't gone to the hairdresser earlier and the next day I had short hair.

I didn't wear that dress again, but this situation made me miss dresses after a dozen or so years and made me like crossdressing.

 

[morro]

I dont recall a specific point, more it evolved. Which is different to wetting & messing myself, which started in childhood. . But I do remember buying my 1st bra, which really did open the lid on my femme side. That was about 15 years ago. and now I am dressed most days and with an extensive wardrobe of undies, tops, skirts, jeans, stockings and suspenders, heels, makeup, etc But even when I need to show my male persona I will have my undies - bra and knickers - on underneath shirt and jeans. I have also become very good at buying femme tops and jeans that I can get away with when in male mode. Femme leggings and skinny jeans are also great at keeping poop in place when messed - allowing me to enjoy being a very naughty lady!

 

[michaelmc]

My firt time was about 8 years old my auntie was clearing out my cousins old clothes and i helped myself to a pair off knickers with carebears on them white with pink frilly elastic and a pair off bikini bottoms pink with barbie on them .
When i got home i put on the knickers an wore them for ages and the bikini bottoms i wore in the bath it felt so right to me , i kept them hidden behind a draw

 

[BabyLouise]

I always had that dream, that I could visit the neighbors with their 4 girls and that they would help me dress like a sweet girly. I was rather young the first time I roamed around in the drawers of my sister. Lately I have found that some shops for second hand stuff actually maintains a little box with underwear in a corner. It is bit embarrasing to hunch down and grope a few and hurry to the exit to pay and come home and try them. Some are really cute, but I have not time to make a selection, really.

Some of 5he second hand shops/charity shops near me sometimes have underwear. I think it depends on the staff. I got an amazing full body girdle in one and some knickers in others.

 

[scrtadssy75]

I still love pretty dresses. Flowers or home coming dresses! Love wearing tights and cute panties. I also wear my dresses with diapers and leggings.

 

[LucyMarie]

Me

I still love pretty dresses. Flowers or home coming dresses! Love wearing tights and cute panties. I also wear my dresses with diapers and leggings.

Me too!