How did crossdressing start with you all?

[GabyinPurple]

Around the time I joined up, I was at Big Tots' Etsy page, looking through the clothes & diaper covers, when I found myself in the Dresses section...and there was this all-white baby doll dress/nightie that looked so scrumptious, so adorable, it bugged me, screamed for me to buy it! I couldn't understand why it was happening but suddenly I felt an extreme urge to buy & wear a dress as strong as an urge to diaper up...so I bought it.

When it arrived, I ripped opened the package, pulled out the dress, looked it over: it was cuter than ever! So I got naked, diapered up, binkied up, got a teddy ready, slipped into the dress, laid down with Becky for a cuddle...instant bliss! So happy, so comfy...instantly felt like a sweet baby girl!

And that's when Bobbi Sue Ellen was born. After that, I got another dress with a pink print theme & Peter Pan collar, then the adult Mam pacifiers, then bought pink hi-tops, some bows, other things. And being a baby girl was here to stay.

What an amazing experience. Nothing this simple or fast for me.

 

[GabyinPurple]

Not going to be a lot of detail here to start with. Other profile/sites that I have shared more. That may change but if interested I will point you toward them.
My earliest recall is being dressed at 4 y.o. for a Halloween party by parents in total as cowgirl bright medium blue with lots of white fringe leather cowgirl outfit, boots, hat and even girls panties. Probably hand me down from older sister but who knows. Apparently after that a history of feminine Halloween costumes. At some point around 6th or 7th grade acquired a pair of older sisters nylon/rayon panties. Loved the feeling, keep those almost 15 years until got religious and married, massive purge. Maybe another 12+ years marriage basically crap started exploring dressing again. Now realized I am trans but no money and health issues not going any further. About a week ago now found diapers.
Hello from Gaby.

 

[StrawberryPan]

Why would he make a better girl - Is he very girlie ? small dingle ? effeminate ?

No, none of the above, and I'm glad to have no idea what's going on in his pants haha. Idunno its complicated. He never really liked typically 'boy' stuff and I could tell he was too embarrassed to get into 'girl' stuff but occasionally I would talk to him and he would say how he was watching xyz show and it was totally a girl's show. Just, has more of a girl's heart if you ask me. Very sensitive, kind and thoughtful. Then again, gender notions are mostly bullshit so he can be whatever he wants.. I just think he would have been happier growing up as a girl liking girl-ish stuff than a boy living in the cut-throat society that was our schools where he was too innocent and shy to really connect with any of the male chumps that were 'the norm' but way too shy to talk to girls, and forced to pretend to like the stupid boy stuff and mindsets just to not feel like a total outcast... I was lucky enough to be born with a social disposition so I got along with everyone via pure kindness and heart but he was too shy for that and spent most of his time alone in his room.. Anyways now he's living with a boyfriend and seems pretty happy, but never even had a chance to experience being with a girl or even being friends with one, so really has no idea how to quantify the way they think or what his true gender identity might be.. And at this point it's really too late for any of that anyway. But I guess the most important thing is to be happy and loved, and his partner seems to really care for him, which is more than I can say for myself right now......... Its complicated..

In short its just something my intuition tells me. Sorry for blogging about it

 

[Happy2BeInNappies2]

I for one enjoyed reading your blog @StrawberryPan as your description of your brother's childhood sounded very much like mine, except that I wanted to use nappies instead of the toilet and always wanted to be a girl like my younger sisters.
(Never had any brothers).
And yes, I was seen by one of my sisters wearing another sister's panties and dresses when I was home alone, but was caught out by my sister coming back early before I could hide from her.

 

[heymanbaby59]

I don't think I am a crossdresser per say, though before onesies my wife/mummy would put either a short loose dress or short feminine nighty on my to make it easy for her to change my nappy.

I know when she had me in the short feminine nighty, she would ask me to wear a padded bra and lipstick and perfume if we were making love.

I will admit that sometimes dressing like this did excite me sexually with her.

 

[heymanbaby59]

I don't think I am a crossdresser per say, though before onesies my wife/mummy would put either a short loose dress or short feminine nighty on my to make it easy for her to change my nappy.

I know when she had me in the short feminine nighty, she would ask me to wear a padded bra and lipstick and perfume if we were making love.

I will admit that sometimes dressing like this did excite me sexually with her.

I will say there was a time in our marriage where she wanted to dress me up as a girl in a really short skirt and her fantasy was for us both the pick up men and have sex with them in the same bed.

 

[DLJosie]

basically nursery i was put in diispers a girlss clothess as i wet myself because i had a fear of the toilets so i was put in diapers a girls clothing xxx

 

[treehopper]

I will say there was a time in our marriage where she wanted to dress me up as a girl in a really short skirt and her fantasy was for us both the pick up men and have sex with them in the same bed.

That could be a helluva surprise to the men - when it turns out you are a transvestite/she-male.

 

[ozzy4605]

That could be a helluva surprise to the men - when it turns out you are a transvestite/she-male.

There are men out there that like that type of a man as a transvestite/she-male, so thay could of had a good time, and we will never know if we are never told what happend.

 

[treehopper]

we will never know if we are never told what happend.

ayup ...

 

[Katiecduk]

I started by slipping into my sisters knickers and bra, loved the feel of silky material on my young cock and how I looked I was about 13....roll on 40 yrs and still dressing and have a huge collection of lingerie, dresses, skirts now and now have added diapers and plastic rumba pants to my collection

 

[Andy86]

I started by slipping into my sisters knickers and bra, loved the feel of silky material on my young cock and how I looked I was about 13....roll on 40 yrs and still dressing and have a huge collection of lingerie, dresses, skirts now and now have added diapers and plastic rumba pants to my collection

I used to wear my sisters also

 

[ozzy4605]

I used to wear my sisters also

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. :-(

 

[ozzy4605]

basically nursery i was put in diispers a girlss clothess as i wet myself because i had a fear of the toilets so i was put in diapers a girls clothing xxx

i have a frend that had prity much the same thing happen to him minus the fear of toilets, he was put into girls clothing at day-care at the age of 4yo, after being told not to get his clothing dirty for the umpteenth time by the day-care teacher and his mother, how it happened from what i have been told, it gos something like this, 10 minutes after we arived at day-care he just ran out into the day-care outdoor play space, he just jumped and slid on his tummy into the sandpit, and riped his pants from tha croch all the way down the left leg, opening them up so you could see his underwear, and his shirt had a big hole riped in it, the teacher had parents bring clothing in for the towns yearly charaty clothing drive, more girls clothing then boys that year, and after seeing how dirty and riped my frends clothes were, the teacher took him strate into the day-care changing rooms, and got a bag with some clothes in it that was just handed in for the clothes drive, but the teacher had another use for them, after about 10 to 15 minutes out came my frend dressed in girls clothing, he had a girls nappy/diaper on under a pastel pink toddler girls dress, with pastel pink frilly socks and black patient mary jain shos on his feet, and a headband with a pastel pink bow on it on his head, his hiar was put in 2 pig tails, he looked just like a little girl out of 1 of the clothing catalogues of the 1940s, 1950s, he hated it but he new that if he mucked up it was this outfit for a week, for the rest of the day he was a well behaved little boy, and he got to keep the outfit to remind him not to reck his clothes ever again and he never did again ever.

 

[DLJosie]

i have a frend that had prity much the same thing happen to him minus the fear of toilets, he was put into girls clothing at day-care at the age of 4yo, after being told not to get his clothing dirty for the umpteenth time by the day-care teacher and his mother, how it happened from what i have been told, it gos something like this, 10 minutes after we arived at day-care he just ran out into the day-care outdoor play space, he just jumped and slid on his tummy into the sandpit, and riped his pants from tha croch all the way down the left leg, opening them up so you could see his underwear, and his shirt had a big hole riped in it, the teacher had parents bring clothing in for the towns yearly charaty clothing drive, more girls clothing then boys that year, and after seeing how dirty and riped my frends clothes were, the teacher took him strate into the day-care changing rooms, and got a bag with some clothes in it that was just handed in for the clothes drive, but the teacher had another use for them, after about 10 to 15 minutes out came my frend dressed in girls clothing, he had a girls nappy/diaper on under a pastel pink toddler girls dress, with pastel pink frilly socks and black patient mary jain shos on his feet, and a headband with a pastel pink bow on it on his head, his hiar was put in 2 pig tails, he looked just like a little girl out of 1 of the clothing catalogues of the 1940s, 1950s, he hated it but he new that if he mucked up it was this outfit for a week, for the rest of the day he was a well behaved little boy, and he got to keep the outfit to remind him not to reck his clothes ever again and he never did again ever.

i probably wouldve wrecked the clothes again so i couldve kept wearing them what you described sounds divine xxx

josie xxx

 

[OriginalWetone]

I agree. When I go to the gym I wear my diaper, running tights, sports bra and men’s shirt to run on the treadmill. Nobody has ever batted an eye at the gym. I tried wearing breast forms while running, but they never stay in place and I end up pulling them out.

You need to find pocket bras for running. They're listed as 'padded' but the pad is just a thin piece of plastic foam to hide the shape of the nipple. It can be pulled out and a breast form inserted, but it has to be the style with individual cups. The shelf style will result in one large lump in the middle of your chest.

 

[OriginalWetone]

I have collected a large 90+ collection all in the vintage chiffon over nylon baby doll nighties with matching panties

So NOW I know why I can't find any . . .

 

[treehopper]

i just come home from school one day, and found my underwear draw was filled with girls underwear

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

 

[vp39]

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

...so that's where it went....

 

[ozzy4605]

i probably wouldve wrecked the clothes again so i couldve kept wearing them what you described sounds divine xxx

josie xxx

My frend got to keep the girls nappy/diaper on under his pastel pink toddler girls dress, with his pastel pink frilly socks and his black patient mary jain shos on his feet, and his headband with a pastel pink bow on it on his head, plus ge got to keep the pack of girls nappys/diapers that his came out of, and his mother got given a big bag of girls clothing in his sizes, some more socks and the black patient mary jain shoshe was wearing, plus the pack of nappys/diapers when she came to pick us up, it was his mothers idea when she got the phone call about what my frend had done to his clothes that day, his mother had taken all of his boys clothing out of his wardrobe, closet and bedside table and draws, to be replaced with the big bag of girls clothing, when we got to my frends house his mother took the bag of girls clothing into his room and dumped it out on his bed, then she started putting them in his wardrobe, closet and bedside table and draws, he was told that this might happen if he keeped wrecking his clothes, after all his new clothes were put away except, for the 3 pear of girls sleepwear witch he had to choose from to sleep in that night, there was a toddler girls nightie/nighgown, a toddler girls satin nightie/nightgown and a toddler girls pastel pink unicorn print onesize with the zip that went from the foot all the way up to the bottom of the neck, he choosed the unicorn print onesize as it was the most boy thing there, i was taken home and the next day at day-care he was wearing a light pastel blue A line dress, a girls nappy/diaper underneath a pear of white leggings, pastel blue socks and black patient mary jain shos, he looked just like one of the girls, and he never again wrecked his clothes, and he dressed like a girl all through primary school and high school as well, i will just say this, he did look cute in the full girls primary school uniform, the schools uniform dress, cardigan and girls socks and black patient lether mary jain shos.