/crossdressing stories/

I'm a pretty attractive straight guy (besides the life long crossdressing) I got dressed up to drive around for the first time because I was living off campus for the first time and finally learned makeup etc, drove down a road I had driven down like a thousand times that has a turn lane a cop pulls me over and told me I ran a light.

At the time I was shitting bricks because 1. cops wear body cams so there's footage of me being a faggot somewhere 2. I'm not a bad person but I've gotten into fights and shit at bars that could of gone legal but never did so I was afraid I was going to jail (never have been, never will be). He walks up I'm dressed like cersi lannister with a blond bob wig and a full face of makeup and he goes

id

hurr durr im going to a party on campus down the road

goes back to his car

I don't remember if he gave me a ticket so I don't think he did?

told me to go on my way

Parked my car in a parking lot then went home

cute
I think I dressed as a cheerleader in middle school for Halloween once. Was fun to prance around like a faggot while trick or treating with my friends (who thought it was funny as hell but it kind of felt right to be dressed like that?) I miss that time. Now life is all about work and depression

After I moved out, I kept visiting my friend until I moved into their place, they kept insisting for me to visit them, so I went with my friend, there's this gaybar a few blocks away and my friend wanted to buy some makeup, we went away for like 3 hours, when I came back my bag was emtpy and all of my clothes were hanging on the terrace

I use to delete all my pictures because I thought people actually cared what other people did, so here's a recovered and cut out version of a picture I took right before I got pulled over. State was Oregon so maybe the cop was liberal and didn't care

Cute, but yeah if you went to jail like that you would have been fucked, figuratively and possibly literally.

I just realized this makes no sense, my parents wanted me to visit them, my father took all my clothes while I was away and displayed them on the terrace.

that sucks

so there's footage of me being a faggot somewhere

He's going to blackmail you into being his sex slave.

Yeah well, he tried his best I think that was his way of telling me he accepted me I dunno lol, like when I was like 10, he was extremely mad I moved the mirror, he couldn't explain to me why it was bad, he knew I wouldn't deny anything so he just did weird shit like that.

I've got a few stories from my studies of advanced crossdressing faggotry. Still have only had straight sex though. Here's another.

I stole a girls cheerleading costume senior year of highschool

nobody every found out who did it

years later I'm in portland at a LGBT halloween party I drove to

I went super early at like doors open and I'm in full fem in the cheer uniform.

I'm having a fantastic time, enjoying all the attention a few hours go by

at like 12:30 her best friend who I didn't know was now an out lesbian walks in

(it was a very big party like prob around 600 people).

I saw her before she saw me

she's walking into an outdoor smoking area im in

I nope tf out and multiple girls like hey where are you going

uhh the bathroom

I turn my head the other way so she can only see my back

I leave the party without getting caught lmao.

Well im openly bi now so he missed the window of opportunity. I would of been scared enough to suck a cock to avoid jail though

kek

it was late and I was like 15 minutes away from the bus stop if I ran the whole thing

halfway through a car stops in front of me and asks for directions

returns a few moments later and asks me to get on, that he couldn't find the street he was looking for

naturally, I hopped on without thinking twice

he told me he was actually going to a meet with some friends and he needed a partner

don't know what to say so I tell him I have school the next day

doubt this mattered but he didn't insist anymore, but he asked me if he could suck my dick

I nervously say No thanks and tell him I just had sex

>Much better

I laugh again and ask him to drop me off

he does

he was driving slow and barely made like half the way

so I go down, close the door and ask him how much to take me to the bus stop

>I told you, let me suck your dick

I smile nervously and say no thanks again

It's not crossdressing but in my defense, I had been crossdressing the entire day with my friend which is why I was so late.

don’t remember what age, but had to be like 7th or 8th grade

been stealing my mom’s and sister’s panties for years at this point

had like three pairs of my sister’s in my sock drawer

was usually very careful and hid them away out of sight

this day for some reason, I was careless and had them right on display as you opened that drawer

was sitting on a chair that faced the dresser while talking to my mom who just walked in

conversation goes on and mom eventually asks if I need some things washed because she is washing a load and doesn’t have enough for a full load.

asks me if I am good on socks and proceeds to open my sock drawer

all I can do it look in horror as she discovers the panties right there

gasps and says “panties! Of your sisters”

ask me what those are doing in there

I just deny and act like I don’t know

i somehow bullshit my way into changing the subject and she seems to forget all about it.

even leaves the panties there when she leaves the room

thatwasclose.jpeg

Never mentioned it again and I proceeded to hide the panties again and eventually get rid of them

You look really nice/cute.

Also wait, uhhh, the neo nazi Kayla who posts on Anon Babble and Anon Babble and flooded a wine cellar or something?

Was it an old creepy guy? You have to be a European because nobody in America would get in a car or a bus willingly
Lmao she knew you were at minimal jacking off in them and she would have never given them back to your sister even after a wash because of the subtext.

Thanks im 100% sure if I was like five years younger I wouldn't have just done the passable trap Anon Babble thing but would have transitioned. Still think about it alot for the lulz.

I don't know Kayla has dark hair, transitioned im pretty sure and I knew him/her from Anon Babble and Anon Babble we would talk about making a band

Yeah perhaps you are right about her not wanting to give them back to my sister.
I have a bunch of close call stories and stories where I was basically caught.

in second semester of college.

roommates with a girl I knew from my hometown

we have a bunch of friends over to drink and stuff

im at home, so I’m wearing comfortable loose clothing not thinking much of it

have these pretty basic looking bikini cut panties on

no lace or frills, just sky blue, plain panties

put on the balcony smoking with people

my loose shorts fall a bit revealing maybe and inch or so of my panties, but no one noticed as we were all facing the railing and standing pretty close to each other

I picked them up quickly, and relieved they didn’t see

open glass door and go back inside

three girls are giggling, one has sort of a disappointed look on her face

one is kind of smirking

third girl says “you’re not a girl”

I say “what?”

they all sort of look at each other, dont say anything, and change subject eventually

slightly mortified but keep telling myself they didn’t see and she meant something else

eventually get over it years down the road and jerk off to the memory.

Not at all, he seemed very well groomed, smelled nice, his car was completely clean, he had some stuff on the back but not even dust, he was wearing a polo and he looked kinda athletic, he was bald but it looked like he shaved constantly, he had a beard but it was well kept, he seemed nice at first glance. I don't know why I got in his car, my friend lectured me several times about it and I won't do that again I hope.

be me, twinkhon crossdressing at a con

get a lot of looks by attendees cuz my cosplay is good and looks cute on me

pretty sure I ate poisonous food last night

puke like 7 times randomly during the event

old lady finds me and takes me to the con pseudo infirmary

try to keep my cool in front of nurses and doctors testing my blood and pressure while I dress like an idiot

20 mins later, some girl at the con wants to take photos of me

reject her by puking in the floor

oh ffs lmao that's rough

Another story

be me, 3rd grade

would wear my moms or sisters panties to school pretty regularly

must have liked the idea of getting caught because this day, I intentionally wore the panties above the waistband of my pants

the thought of someone seeing was exciting to me but knew it was social suicide

did it anyway

when I would bend over, you could straight up see like two inches of panty because my shirt would ride up

had on a light green satin pair that had picot trim all along the waistband

desks in class were set up like four desks in a square.

boy who sat next to me didn’t really like me and was often cold to me or didn’t talk to me

class in session

i drop my pencil off my desk and have to bend forward in my seat to pick it up

forgot how on display my panties were when i do this

i get back up after grabbing the pencil

boy next to me slightly gasped and is looking at me with a big smile

he was really nice to me after that day and we even became good friends

he never mentioned seeing anything so I’m not 100% sure if he saw

was always friendly after that to me and would playfully call me a girl

I am guessing he used to wear panties in secret too and was relieved someone else was doing it and being so bold.

parents come visit want to see some videos I've taken and stuff

start playing them on the big screen

remember I took some photos en femme

tell them I have more on my PC

open gallery

had sync on

last row displayed has one of those

brother snickers

father sighs

Similar to that one!

be me, about 24

work at a department store

often use my employee discount to buy panties from there.

start dating a girl who worked there

she wasn’t very cute, but she asked me out so I said yes because I appreciated a girl taking the initiative

we date for a bit, and I eventually tell her I like wearing women’s underwear

she’s cool with it and ends up being supportive, even bought panties with me sometimes

we eventually break up over other shit

it was bad break up where I didn’t want to see her for a while

tell my boss I’m quitting for some bullshit reasoning about school

boss begs me to stay since I am such a good worker

says she will give me two weeks off to do what I gotta do for school and such

everyone thinks I quit

I come back after two weeks and my ex is surprised

I eventually find out she told at least two other cute college girls who work there about my panty wearing

one who used to be interested in me was no longer interested

they would all sort of giggle at me when they were all together in a room

again slightly mortified, but trying to make the excuse that they don’t know

eventually get over it years later and jerk off to the memory.

if I was like five years younger I ... would have transitioned. Still think about it alot for the lulz.

you do realize that this "I kinda wanna be a woman" thing never goes away and having sex with dudes doesn't replace it, right?
you're here reminiscing about being a young crossdresser, saying you still think about it... that's called repression anon

Another college age one

in school library

not many people around as I was studying kinda late

towards end of my studying day, I am sort of careless and didn’t realize my pants had ridden down a bit

wearing black satin panties with lace all along the top

hear a girl giggle

turn around and realize some girl had taken a seat at the desk behind me, facing my back

she is just looking down at her iPad and giggling to herself

suddenly realize my panties were on display as I was stood up gathering my things into my backpack

left as quickly as possible

meh no one will notice

Often when I need to buy shit and I don't want to undress I just put on some pants and a jacket, every single time someone notices.
I started being more careful when I went to a convenience store and my jacked was unbottoned, I was wearing a bodystocking and this cashier guy noticed, he became increasingly aggressive towards me, or so I thought up to the point where I overheard him saying he wanted to beat some "fags", I was so lucky that he just stopped working there.

Not a story, really, but the first time I ever got intimate with a girl she remarked how impressed she was at how fast I undid her bra. I hid the flash of embarrassment well, but didn't bother telling her how I had gotten so good at it. I literally owned the exact bra I had just helped her remove, in a different color and cup/band size.

lol
I had to teach a friend how to do it with one hand, and this other one that did it backwards and just twisted it around

Yeah around those times I always tired to wear very gender neutral looking panties. But it seemed like the occasional days I picked something girly, with lace or something, I’d end up in a situation where someone was gonna see, and sometimes did.

Yeah, doing it onehanded and in one go is what shocked her. I was 16 I think and had been buying my own clothes for a while by then. I was terrified that we shopped at the same Target and that she'd catch me one day. She was gossippy, too and I had this irrational fear that one of the friends she told about my little skill would know exactly how I had picked it up, since I wasn't any kind of ladies man.

I only ever stole clothing very early on, around the age of like 11 or 12. I've been buying my own stuff since I was old enough to walk to the store on my own. I got caught every time I "borrowed" something and I hated the feeling more than I feared someone seeing me buy women's clothing.