Crossdressing stories thread. How did it start for you?

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sounds hot anymore happen with this story? How did the dress feel?

>early 2000's were a huge time for homophobia so wearing girls clothes and having make up was not ok
>never got any judgement from my girlfriend or her mum and always had it washed of before i went home
>while sitting in this dress my girlfriend asks to do my nails and i said sure as long as we could get it of
>wearing make up in a red dress and getting my nails done i felt so girly but i didn't really care
>one time i even wore her underwear, just a bikini cut, nothing special, red coloured cotton
>eventually i was cleaned up, old clothes back on and went home later that day
>this relationship continued for two years, with less make up and cross dressing
>eventually she cheats on me with an even blonder and younger kid
>my hair was white blonde but his was bleached chalk blonde, felt so mad
>eventually got over it but i missed the girly fun we had
>could never tell anyone, but i was getting pretty popular at school because it got out that i had had sex
>only me and two other boys had sex but i low key didn't like it and never saw why it was cool
>become friends with this other boy, he also had an older girl prey on him
>we went to an opp shop and i saw this dark red make up, i dont know why but i put it on, felt so girly, got hard
>quickly rub it of before he saw and went home, but stole the make up
>realize i had no idea what to do with this make up
>try it on a few times and eventually sneak it into my mums stash of make up
>couple of years later parents divorced and mum got a new boyfriend
>we went to his place, his ex had up and left all her stuff there, i saw a g string and i stole it
>wore the g string while jacking of so many times
>really got into quizes that told you which character from a show you were, they were popular in magazines
>really liked when i got the girl characters, got me horny
>eventually g string needs washing and would sneak it into the pockets of pants
>learned how to do laundry because of hiding this g string

god that's a perfect bussy

dress felt softer than any of my clothes, it was really fun and freeing
>mum is really happy that im doing my own chorus, im happy i can hide these panties
>eventually start stealing girls underwear
>over the years i suddenly grow massive, im 6.2 by 15 and pack allot of muscle on
>have huge jaw, and went from class clown to getting actual attention from girls
>steal panties of girls i hook up with
>long history of stealing girls clothes, purging and repeating
>it is really hard for me to wear girls clothes, easy to get but im not a cute boy anymore
>get really into sports and putting on muscle, find Any Forums, learn about traps
>want to be a trap but i look more like a chad
>nobody knows my secret, don't even care about hiding the girls clothes in my room
>mum finds girls clothes all the time but knows im hooking up allot so its never brought up
>have girlfriends and always take them shopping
>they love it, always buying them lingerie with the pathetic money i have
>secretly wear it when i can
>this habit continues to this day

and yea thats how i got into it and pretty much where i am today

I would give you $100 if you show them in public

>be me 14
>around friend's house, let's call him Harry
>his sister is 15 and considered a bit weird at school, let's call her Emily
>playing vidya with friend
>his parents are out but his sister is in her room
>friend jumps up and swears to himself
>I ask him what the problem is
>Harry tells me he left his damp swimming kit in his locker at school
>look at the time on his alarm clock
>the school gates will be locked in 20 minutes
>"stay here" he says as he sprints out the door
>I look out the window as he runs to the shed and gets his bike out
>even when cycling the school is like 10 minutes away
>I sit back down, cross my fingers for him and get back to playing vidya
>suddenly the door creaks open behind me
>Emily is poking her head around the door
>because Harry is not there, I feel like I'm not supposed to be there on my own
>I explain that Harry has gone to get his swimming kit from school
>"it's just us then" she says
>"errr... yeah" I say
>she reaches her arm around the door and beckons me with her finger
>I don't know if I'm in trouble or something
>pause my game and save it
>walk out of the door where she's standing in the landing
>she's still wearing her school uniform (white blouse, navy blue skirt and navy blue tights)
>she gives me her hand signalling me to hold it
>I reach out and clasp it with mine
>she leads me into her room and closes the door
>already getting a semi
>"we have 15 minutes"
>still confused but turned on
>she tells me to sit on the end of her bed
>she unbuttons her blouse and takes it off
>then unhooks her bra and slides it down her arms and drops it onto the floor
>first time ever seeing naked breasts like this
>immediately become rock solid
>she does a couple poses for me
>just as I think it's about to go further she pulls her purse from her handbag
>she pulls out a £20 note and holds it upwards with two fingers
>she asks me if I want it
>I nod my head
>she tells me to stand up
cont.

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Fuck!!! Where can I find something like her. Fuuuck

need more, way better than my green text

enjoy ;P

>Emily opens up one of her drawers behind her
>it's her underwear drawer
>just stand there entranced with all the bras and pairs of knickers
>I even spot what look like bikinis
>"strip" she says
>"what?" I ask, kind of struggling to pay attention to what she's saying
>she repeats herself
>I undress myself practically at the speed of light until I'm down to my boxers
>she giggles when she sees that I have been pitching a tent this whole time
>"go on" she continues
>I grab my waistband, slide my boxers down my legs and let them drop to the floor
>cannot stop staring at her perfect tits
>she looks at my boner
>it's not the largest thing in the world because of my age, but it's not too small either
>"now if you want this £20 note, you've got to do a dare for me"
>pause
>"I dare you to pick out a pair of knickers and wear them to school tomorrow. You have to wear them all day, no exceptions. You can then come back here after school to collect this money" she says
>heart sinks and it feels like I have a frog in my throat
>I'm still really horny so I think about it for a second
>haven't got PE tomorrow so it's not like I'd need to change in front of anyone
>£20 would be really nice to have
>no one would be able to know
>"will it be a secret?"
>she smiles in a wholesome way and assures me that this is strictly between her and me
>turn to her drawer again and rummage around
>she glances at the clock
>"we've got about 5 minutes left" she tells me
>I am spoilt for choice. I don't know what to wear
cont.

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I always wore skirts and stuff in public, but not as a trans things. They were just comfy. Then one day on Any Forums I saw some pictures of cross dressers that were pretty hot and thought "I could do that". So I got some lingerie, grabbed my camera and went to town.

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