These threads used to be huge back in the day

>>45074826
Nobody crossdresses anymore, everyone either troons or wears that awful femboy uniform

I used to wear my mom's clothes while she was out of town and show my body to men online.

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>>45078187 >>45079620

>>45074826
>be me
>only get apartment by myself after college
>try crossdressing + makeup
>it only highlights my male body and features
>cry
>repress for another 5 yrs

>>45075121
Yeah but you’d assume it’s something like half the people in this board have at least dabbled in

>>45075194
I really don't think so. Half the trannies here identify as manmoders who would rather die than be seen in a dress. Just about everyone here medically transitions for years before changing their presentation. This isn't a demographic that would have fun crossdressing stories.

>>45075073
I member
First time I came to this board there was a huge thread of this and it kept me coming back

>arguing half-heartedly with friend
>make some comment I can't remember about knowing something about him
>he says "yeah well I know your panties are gray"
>I did have secret gray panties and I never knew how he knew and pretended like he was bullshitting and it was never brought up again

>>45074826
Not my story but heard this from my sister about a lesbian acquaintance of hers
>Woman gets engaged to her girlfriend
>Decides she wants her five year old nephew to be the flower girl at her wedding
>Kid is very feminine, has long hair, likes wearing princess dresses
>His mom (her sister) thinks it’s a great idea
>They take him to a bridal shop
>Kid has no idea what’s going on
>They start picking out dresses
>Take him into a fitting room and change him into a dress
>He loves it and thinks they’re just buying him a pretty dress to wear
>They explain to him what a flower girl is
>Tell him he’ll walk down the aisle carrying a basket of flowers
>Kid misunderstands and thinks he’s getting married
>Freaks out and starts screaming and crying
>Thinks his mom is marrying him to a boy to get rid him
>Causes a huge scene in the shop
>They try calming him down but he’s inconsolable
>Quickly change him back into his clothes and leave the store
>They abandon the idea entirely

>>45075249
>>45075194
>>45075121
I'm a guy who crossdresse sometimes, but my stories aren't really cute, it's just me dressing up and showing for or getting railed by bigger guys.

>>45074826
I remember this time when I was still living with my dad and his girlfriend and I was 19 at the time
>Be me
>Retarded fat faggot
>Be awake late in the winters night
>Not a big deal, am really the only night owl
>Be hungy
>Still be retarded
>Venture outside of my bedroom downstairs toward the kitchen
>Wearing only my black hoodie and matching black cotton/spandex panties
>Thought will be quick not a big deal
>In kitchen
>Still hungy
>Look outside window and see the garage light on from the door
>It's over.gif
>Not realizing father was having a late night smoke
>He comes inside
>Eyes locked
>Be still wearing just a hoodie and panties that are getting completely eaten by my ass
>He looks away saying nothing and rubs his eyes with his hands
>He goes back upstairs to sleep
>Kms lol xD
Inb4
>Larp larp sahur
He probably just didn't care at the time from the taking a puff of weed is my thinking.

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i'm a big hairy cis male top and sometimes i like to crossdress. i literally do not know why, i have no desire to be female or even feminine and i have a big dick so wearing panties and stuff is awkward anyway. i think i like it BECAUSE it's so "wrong" and doesn't fit me at all, idk. i'm also way into sph despite having a big dick. i think it's because when i'm jerking off my brain can slip into "performance mode" and it makes it harder to relax, so crossdressing/sph helps me slip into a different mindset

>>45075327
Yeah, you just do it in private, like anyone else nowadays. The people who used to crossdress in public or even daily life are all just trannies now, who wouldn't call what they're doing crossdressing.

>>45074826
I’ve been caught to twice. Once in HS when my parents were out of town and they had this couple stay with me for a week. I didn’t hear the lady come down the hall and she was standing in the doorway watching me watch myself in the mirror with panties on. I dont know how long she was there but I was rock hard and posing. I finally saw her and freaked but she smiled and walked away and never said a word.

Another time in my 20s, I was dressed in thigh highs and panties and a sexy t-shirt and had the sliders open. I was on the phone when I realized a dog walker who passed everyday was just standing there looking at me while her dogs sniffed. I pretended not to notice her and let her look.

>>45075302
Being a flower girl or bridesmaid was something I used to daydream about when I was little. I remember going to a wedding and absolutely seething with jealousy at all the pretty dresses

>>45075162
When I was 13/14 I would post pictures of myself dressed up on one of those early 2010s anorexia/thinspo forums. Sounds fucked up but I’ll make a greentext later if this thread is still up because I have a surprisingly cute story about it

>>45075299
This is hilarious

when I was 22, my gf and I moved into a small apartment together. we fucked at least once a day, usually somewhat kinky stuff like tying each other up or choking and hitting. since prepuberty, i crossdressed whenever i was home alone, and since femboy stuff was becoming more culturally normal at this time, i hinted i wanted to try dressing as a girl during sex. she wasn't crazy about it but was still supportive because i reassured her i wasnt actually trans or anything (lol i guess) and that this was just for some kinky fun. i also felt like giving her some clue of my "big secret" was a step forward in our relationship. i bought some cheap lingerie online that looked cute, found a cheap wig, then she helped me with the makeup. my heart was beating like crazy the whole time and i felt anxious and vulnerable when she was drawing on my eyeliner, but she was still sweet with me. we didn't even have sex. i looked in the mirror and cried when i saw myself: a man in women's underwear, weird clown, rocky horror cosplay, disgusting sissy. for many months after, i was extra depressed and struggled a lot with my identity. twinkdeath had ramped up, and then i came out as trans and started HRT a few years later.

I manmode full-time now out of shame for ever crossdressing and being AGP. Our relationship is better than ever now too, even though it was hard at times. I'm no longer a weird sex pest.

>>45075819
happiest tttt crossdressing story

>>45075847
I have mixed feelings about how it all happened, but it ended up being ok. She told me recently she would still choose to be with me even if she had known I was trans from the start. My only regret is avoiding learning about anything trans related and deluding myself into thinking I was a "normal" crossdressing man for years.

>>45076025
If you're still with her, just be aware that this can also keep you stuck in old patterns and old thinking. Even if she's OK with you transitioning, people still have routines they like and expectations that have been built, and you can find yourself upholding those in ways that hold you back, knowingly or unknowingly. Not saying you should break up, it's great you're still together and the story is cute with this context. But it's something to be aware of.

>>45075611
i wanna hear the story anon

>>45076171
Yeah, I know exactly what you mean. We've always been pretty egalitarian, but I'm still the man and also bigger than her so there's no getting out of that, in this relationship or with anybody else. I've come to terms with it.

>all these stories and not one of them are getting (You)s
yeah this board is dededed

>>45076581
I don't know you, but I really don't believe that has to be true. But I get why it would feel that way. Moving what gender people who knew you before transition can be hard even with friends, and intimate partners are a whole different level still. I don't want to overstep, but I hope you figure out a way to be yourself and to be happy. I'm sure you can.

>be 14, faggot, know I'm trans but Dad is very anti-lgbt
>get home from school at 3:30 usually
>mom always comes home at 6 or later because she does sports stuff with my brother
>usually spend this time trying her makeup and dresses
>one day, be in her bathroom following makeup tutorial
>dont hear garage open
>suddenly she opens door, game was rained out
>scream "don't come in! I'm naked" And hold door to keep it from opening all the way
>suddenly aware of mirror, she's staring me in the eyes
>she lets go and says "okay let me know when you're done"
>cry silently and take off makeup, never use her bathroom again
>she stops asking me if I have a girlfriend and starts asking me if I have a "partner" or "someone im seeing"
Craziest thing is she still says she never expected me to transition. She also saw much worse in my college dorm but thats another story

>>45076756
>She also saw much worse in my college dorm but thats another story
Well, tell us the story!

>>45075397
>but she smiled and walked away and never said a word.
that was nice of her

>>45076756
idgi, what mirror? like she saw your naked ass in the mirror behind you at the back of the bathroom or what?

>>45074826
It's a long story of how I got into this living situation, but I was roommates for some time last year with my best friend and our crackhead friend. He was 51. We think he's dead now. But he was a nudist and a crossdresser.
He'd get clothes and weird shit all the time from clothes donation bins and bring it in. I would have a lot of fun dressing up with him, and he told me once, "I never thought I'd meet anyone like me".
As fucked up as that time was and how absurd and degenerate we were, I'm still touched when I think of how he said that.

I remember wearing my sister’s clothes and pretending to be a girl on Omegle when I was 13...
I wish I could have transitioned at that age; life would have been better.

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>>45077030 >>45077215

>>45076756
>but thats another story
Let's here it!

>>45076859
Picrel for Pajeets that don't know how bathrooms work, the door opens to the mirror and someone looking into it can see behind the door.

I don't have any great stories. Anytime I think about my early experimentation I think about losing nearly $300 of crossdressing clothes to a room-ransacking from my stepdad. And then getting grilled in a "homosexual intervention."
I still haven't forgiven stepdad for that.

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>>45077072 >>45077103 >>45077139

>>45076859
Basically this >>45076955
Here's a diagram though.

I'll type out the college story...

>>45077030
take ur time, i'm waiting

>>45077030
i await your tale with great interest

>>45077030
I hope it's deeply mortifying.

>>45076955
>Picrel for Pajeets that don't know how bathrooms work
you're stupid for thinking every bathroom looks like that, maybe get off /pol/ and twitter and read a book or two

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>>45077215
'tis a joke, nona, relax. She's just japing.

>>45077215
>oooo I'm a dumb nigger who doesnt comprehend 3d space please feel sorry for me

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>>45078241

>>45075073
yeah, i miss these threads from like 2018/9. they were super relatable and one of the main reasons i started using this site

>>45074826
Although this was traumatic at the time, I give you all permission to laugh at this story
>Be a very effeminate 8 year old
>Like so faggy it makes me cringe to think about
>Live in big college town
>At my aunt's house alone with my two girl cousins who are 12 and 14
>Our moms are out shopping
>Cousins ask if I want to play dress-up
>Of course I do
>They take an old pink formal dress out of storage that one of my cousins wore when she was my age
>Very pretty, has a pink sash around the waist with a big bow in the back
>Put on the dress and cousins put heavy makeup on me
>Put on a long costume wig and they style it with a pink bow
>Look so beautiful
>Their backyard is surrounded by a tall wooden fence and has a big flower garden
>Next door is a two story house where a bunch of college boys live
>There is a balcony on the second floor that overlooks my aunt's backyard
>Cousins want to take pictures of me in the flower garden
>Go outside and sit on a stone bench like an elegant little lady
>Cousin says she needs to fix my wig and takes it off
>Didn't notice there were a group of college boys sitting out on their balcony watching us
>Hear "Holy shit is that a boy?"
>They all start yelling down at us and laughing
>One of them calls me a little faggot
>I sprint inside the house sobbing
>Sit on the couch and cry while my cousins console me
>Our moms come home like ten minutes later
>I'm still on the couch wearing the dress, sobbing with makeup smeared all over my face
>Cousins tell them what happened
>My mom is so upset
>They clean me up and change me back into my clothes
>Mom drives me home and I cry the whole time
>Am sullen and depressed about it for weeks

>>45076639
That's nice of you to say :) I'm getting there, and things have for sure gotten better over time. For now, I want to try to ignore how others treat/see me and focus more on how I feel about myself.

>>45075819
Holy shit same....like all of it including the crying and shit
I did it at 28 instead
I really wish I was as brave as you

We mostly worked stuff out and are swinger moms together now
(She planned getting pregnant around me starting HRT)

>>45074826
>14
>discover I like crossdressing
>raid my mother's and sister's (18) clothes
>mother catches me and all hell breaks loose
>she yells at me
>father yells at me
>works like faggot, queer and pussy fly like the spit coming out of his mouth
>sister strangely quiet
>I go to my room
>about an hour later my sister comes over and tells me to follow her to her room
>opens her closet
>"you can use everything on this side. when you want them washed, put them in that bag. don't get caught again."
>hugs me and walks out
best. sister. ever.

I never crossdressed but i wore thigh highs and used my mom's dildo

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>>45088241

Tfw when my greeny doesn't get a single (Yuo)

>>45077896
I'm a coward, that's why I'm still manmoding after over 3 years of medical transition, including FFS.

>>45078101
honmoders are the real cowards
t. 10 years manmode

>>45078101
Im not manmoding except at work
Im ugly though and have thinned hair though so it's not so much girl moding as looking like a fag

I once grabbed the tablecloth to pretend to be a sevillan dancer and my mom clapped, does that count?

>>45075172
>feel bad about your body being masculine
>let it masculinize further
Why are reppers like this

>>45077306
I miss it too, they usually were the only threads I went on and they would last for days. Stories would get tons of replies and people would be vulnerable and opening up about this stuff. It was nice

>>45077912
That's so cute, your sister is awesome

>>45078187
Cuz agp

>>45078000
Yeah i think thats way worse

>>45076198
OK I'm typing it up now. It's going to be long, I've actually never told anyone about my time on the pro-ana forum before. Despite what people now think about those forums it was actually a nice place for me at the time and the girls were really kind and accepting

>>45077912
amazing sister

Well, this was a fun time for me.
>be me 13/14
>go on family vacation with family and extended family.
>entire fall break gone
>extended family wants to go home sooner
>tag along
>get house to myself for a day/night
>get into bag of goodwill clothes we are going to donate
>get into moms make up
>spend the day as a girl at home. Dressed up. Feeling myself. Absolutely horrible make up job
>wash it off and change before parents get home
That one was nice
But also
>be on family trip
>get time to myself to cross dress
>try on some of mom and ousins clothes not realizing can be seen from the window
>mom says later "what where you doing in our room?"
>"uhhh idk"
>"We'll talk about it later"
Never did end up talking about it. Makes me wonder if I would have come out sooner. I loved that goodwill bag as it was my 'closet' for a long time. They forgot about it and it became my way of coping.

>>45074826
I never crossdressed until an older guy I was hooking up asked me to. Then I dressed for just about every guy I met up with.

>>45077912
My older sister knew about my crossdressing too and helped me keep it a secret. My parents weren’t conservative like yours but it still was better they didn’t find out. Also not to brag but my sister let me wear anything in her closet

>>45077912
Giwtwm

>>45075397
>she smiled and walked away and never said a word.
Wonderful story.

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>>45078693

>be me 23
>repper my whole life
>get a gf
>we hang out alot not a fan of the sex bc i dont like women(hadn't accepted yet)
>come out to her about feeling trans bc she is supportive
>she does my make up and straightened my hair, picked out lingerie for me
>see myself
>realize its actually possible for me to pass
>we hang out and cuddle
>she fucks me with a strap on
>egg shattered
>we start going out with me cross dressed sometimes she helps with clothes and makeup
>eventually start hrt
>ffw to now I pass and have been living as a woman for several years
Me and her didnt work out due to her alcoholism but still, thankful for that.

Can someone else please post a super long greentext so I don’t feel self-conscious about the one I’m typing up now

>>45078614
DON'T HESITATE YOU GOT THE WHOLE THREAD WAITING
>>45077072
>>45077103
>>45077139

>>45078614
Pls post ive done 2

>>45078586
>we hang out alot not a fan of the sex bc i dont like women(hadn't accepted yet)
I had a GF at 15 who truly loved my crossdressing and it was like our big secret no one else knew about. Like she would really look forward to whenever we could be alone and I could dress up for her. She was frustrated with my low libido though and eventually I had to tell her I’m gay and felt so awful about it. She was very cool about it though and said she always suspected I was gay and we remained good friends

>>45078693
Thats lovely <3

>>45078656
OK it’s coming, sorry I’m doing laundry too so keep getting held up

>>45078714
FOLD FASTER.

>>45074826
i didn't really crossdress because i was raised Catholic, but i have one story. if this wasn't 4chan I'd share the pic my mom took of me lmao

> be me in middle school
>everyone has gfs now except me
>best friend sets me up with his gf's best friend
>very bad at being a manly boyfriend
>she dumps me
>"I just didn't feel a spark"
>realize im trans, and i probably dont like girls
>months later it's Halloween
>holy fuck im so excited
>get an old wedding dress from Saver's
>"it's just a joke haha"
>hangout with my friend and his gf
>she LOVES that im wearing a dress
>she dresses me up, does my makeup and hair
>look in the mirror
>kinda cute? sort of
>suddenly my ex arrives with her new bf
>he's a foot taller than me and NOT in a dress
>we all go trick or treating together
>at point she takes me aside
>"anon you can always be my gay bestie :)"
>i have a panic attack and have to go home

OK I finished typing it up. Feeling emotional sharing this, like I said I've never told anyone about this before
>Be a gay mall goth type of kid
>Best friends with a girl who is the same way
>We were obsessed with the band The Birthday Massacre to give you an idea of what we were like
>Live less than a mile apart so I'm constantly at her house
>I'd always wear her clothes while we hang out
>Her sister is four years older than us and she likes to put makeup on me
>Their mom is very sweet and makes it clear I'm always welcome at their house
>In 7th grade she transfers to the private junior high/high school where her sister also goes
>This sucks but we still hang out all the time
>October comes and her school has a big Halloween mixer every year
>Students can bring a guest from other schools if they want
>Friend invites me as her guest
>Really excited to get dressed up and go to a big dance where no one knows me
>Couple weeks before the mixer her sister takes us shopping at a huge costume store (not Spirit, much bigger and open year-round)
>I buy a fairy costume
>Slutty blue and green halter dress with wings you slip on over your shoulders
>Also get a long blonde wig and flower headband
>We also go to a nearby mall and I buy white high heels, a strapless bra, bra inserts, and panties
>Spent like $300 on my mom's credit card
>Go home and mom doesn't approve of the costume but allows it (my mom is cool)
>Been lurking on a pro-ana forum for a few months
>It's all teenage girls and women in their 20s
>Make a post in the fashion section
>Common topic is how hard it is to find clothes small enough in stores
>Say that I'm a teenage boy who just bought an XS fairy costume and it's still too big on me (which was true)
>This gets a lot of attention since it's all girls on there
>They ask if I can upload pics of me in the costume
>Post multiple pics but crop out my head
>Get tons of compliments which feels really good
Part 1

>>45074826
>crossdress my whole life since childhood
>agp, agamp I don’t know
>try being straight guy for most of my life
>never works
>decide I’ll actually go to club with my CD friend
>it was great time
>felt happy for days after
>start talking to man online
>he’s a doctor who likes troons and crossdressers
>get dolled up
>meet up with him for drinks
>he starts getting handsy and it’s turning me on so much
>go to his hotel
>this is the first man I’ve ever been with
>immediately start passionately kissing
>my tuck has come undone at this point because he was groping me the ride over here
>I pull down his pants and start going to town
>he pushes me on the bed and starts giving me head
>I have to make him stop because i want to have actual sex and not cum right away
>I start riding him cowgirl
>omg this is real
>I can feel myself about to cum
>omg it’s nothing like I’ve ever experienced before
>it just keeps shooting
>whole body feels orgasm as I feel him cum inside
>no going back

I was initially worried I would get some sort of post nut regret if I came while he was still inside me but no.

>>45079008
>Tell them about the upcoming dance and how I'm hoping to pass as a girl
>They actually give me good advice
>Stay on the dance floor, dance with boys but also be stand-offish with them, don't talk to them too much, don't let them touch you
>I answer questions about myself and everyone is really nice
>Become a regular poster on the forum over the next couple weeks
>A 19 year old girl I've been talking to a lot gives me her email address
>Went to my friend's house a few days before the dance and asked her sister to do a test run on my makeup with the wig on
>Said that I wanted to completely pass as a girl if possible
>Had their mom pluck and shape my eyebrows because she was really good at it
>Took pictures of my face before leaving
>Went home and uploaded my face pics on the forum and asked them to be brutally honest about if I pass as a girl
>Everyone said yes which was a huge relief
>Day of the Halloween dance arrives
>Go to my friend's house and we all get dressed up, her sister's friend drives us
>On the way they all promise to not tell anyone I'm a boy
>The girls look super cute in their costumes and I also look amazing
>I'm so nervous and excited
>Get to their school and the dance is enormous, like 500-600 people are there
>It's both indoors and outdoors
>Have so much fun dancing in the fairy costume
>Dance with random boys and follow the advice the pro-ana forum girls told me
>Friend stays by my side the whole time and runs interference when necessary
>Talk to people a bit but thankfully my gay voice and the loud music prevents any clocking
>Use the girl's restrooms with no issue
>Really everything goes perfectly
Part 2

>>45079014
thanks now im hard

>>45079014
oh no, this is hot :(

>>45079021
>The dance ends and I get dropped off at home
>First time my mom has seen me dressed up like this and she absolutely loves it
>Is shocked at how well I pass as a girl which makes me feel so good
>She helps me remove the makeup, I change out of the costume, take a shower, and pass out
>Next day I make a big post on the forum about my night and upload pictures of me dressed up
>Feels crazy back at school, don't say anything about the dance to anyone
>No one knows what I did
>Feels like I have a double life now
>Decide I want to start crossdressing a lot more
>Not like the way I did before the dance, but now fully dolled up and with cute dresses and heels
>Keep posting on the forum over the next year and post a lot of pictures
>Email back and forth with the girl who gave me her email address
>She's a college freshman and tells me all about herself
>Pretty sure she thought I was 16/17 but never asked my age (no one on the forum did)
>One day the forum just suddenly disappears with no explanation
>Really sad about it, had a community of women who were kind of like my mentors and they all seemed to care about me
The end

>>45079032
IT JUST ENDS THERE?!?
I hate that real life doesn't care for carrying a plot line through. I felt how you felt in this post, it must have been crazy.

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>>45079044
Forgot picrel

>>45079032
im glad u had a somewhat positive experience still. I imagine u trooned?

>>45074826
>friend's 16th birthday is coming up
>talk with other guy friend how funny itd be to wear sailor uniforms for it
>he thinks it's funny too
>bring it up to birthday boy
>"yeah ill buy them"
>other guy agrees it'd be fun too
>we have 4 people doing this
>fast forward to day of
>we go upstairs to a room with a closet
>take turns going inside and dressing up
>far right brother of birthday boy enters the room
>everyone wears a blank expression
>"you guys are funny"
>he leaves and we pose for photos
>keep crossdressing with them every so often in higher quality outfits
>never see them again after highschool

>>45079085
how is this crossdressing?

>>45079097
japanese sailor uniforms with skirts

>>45079103
oh. I thought.u meant like gay us navy crackerjacks

>>45079123
yea i shouldve clarified

>>45079044
It really is insane, isn’t it? I’m actually looking at pictures from that night right now. Unfortunately I won’t post them due to my age at the time but god I looked so amazing and am now feeling sad but also very glad that it happened

>>45074826
not sure if this really counts but it's the closest i've got.
>1st grade
>Perpetually embarrassed child (still am) with the fear of God in me who would never risk invoking my family's ire by crossdressing
>No sisters, no girls cousins, no friends of either gender, no access to girls clothes, only female presence in my life outside of school is my emotionally neglectful mother
>only outlet for feminine expression (which i cherish deeply and am terrified of having discovered) is playing girl characters in videogames for short sessions before deleting my save file in case my parents or older brother check it for some reason
>whole class plays club penguin together, in and out of school
>one day at home i'm playing it and i see this light blue princess dress with a blonde wig and tiara in the catalog
>I just, want it. Really badly.
>Against all my instincts I buy it. Terrified of being walked in on.
>Go out in the game and talk to strangers and pretend I'm a girl
>Inexplicably happy in a way I don't understand
>This virtual dress is my most prized possession in the entire world
>A couple days later, "accidentally" (in retrospect, a part of me wonders if i wanted to be caught, but I can't honestly remember) forget to take the dress off
>The next day at school we have a little 20 minute computer break, we're all playing club penguin
(1/2)

>>45079080
Amazingly I did not troon but definitely considered it. I would have pretty severe periods of dysphoria that would come and go throughout my teen years. By the time I was 18 it mostly died down though. Kept dressing up the whole time though

>>45079023
>i’m hard
Do something about it
>>45079024
Go out there and get a similar experience

>>45079185
(2/2)
>The moment I log in someone looking over my shoulder notices my penguin is in a princess dress and draws everyone's attention to it
>*entire* class laughs at me and makes fun of me for dressing up like a princess
>mortified
>insist it wasn't me and that somehow "my account was hacked"
>no one believes me (obviously)
>never again
>can't remember if it started here or not or if it was something else I did, but for the next 5 years everybody in my class calls mockingly calls me by the gender-swapped version of my birth name

Reading the experiences the rest of you had I feel this pit of despair opening up inside me. I fantasized about these exact kinds of scenarios every single day when I was a kid but nothing like that ever happened to me. I eventually caved to dysphoria when I was 19 and now I'm a clocky ugly twinkhon in my early 20's who just wears jeans every day. never anything cute because I can't pull it off. the most i ever got to express femininity as a child was in a fucking videogame.

For the remainder of my childhood I made a habit of going on those talk to stranger websites and telling the truth about my age but lying and saying I was a girl. I would talk to pedophiles online for a couple hours a week and they'd ask me things like "what are you wearing" and I'd make up something I wish I was. Some of them would tell me about how they were touching themselves while talking to me, but I never did. It was the only time I got to be a girl.

>>45079257
>Reading the experiences the rest of you had I feel this pit of despair opening up inside me. I fantasized about these exact kinds of scenarios every single day when I was a kid but nothing like that ever happened to me. I eventually caved to dysphoria when I was 19 and now I'm a clocky ugly twinkhon in my early 20's who just wears jeans every day. never anything cute because I can't pull it off. the most i ever got to express femininity as a child was in a fucking videogame.
ugh same. nobody ever taught me how to do makeup or dress myself. I wore a dress a few times but I looked so disgusting that I am permanently averse to it now.

yknow, i should've expected this thread to be horny. i typed up my story and was like
"what a cute memory :)" and then the next stories were all horny lmaooo

>>45079283
a hsts in a sea of agps

>>45077072
>>45077103
>>45077139
Im so sorry I was out with my husband and completely forgot... i feel like I set unrealistic expectations... I tried to reduce the smutt
>be 22, HRT femboy, have a bichad bf who's 24 that I met at a coffee shop on campus
>younger brother (20) attends the same university as me
>parents are in town visiting him for parents' weekend
>they know I'm not interested, so they just ask if I want to go out to dinner
>tell them no, I have leftovers at home that I'll eat
>bf asks if he can bring his computer and spend the night
>yes, obviously
>before he gets there, I put on some cute makeup and an oversized T-shirt, white stockings
>he gets there and forgets to lock the door behind him
>we sit on the couch in the living room gaming for like 2 hours
>I have more women's clothes than men's, and the men's are androgynous at best
>bf really likes "traps," so I have a lot of generic maid, bunny girl, qipao, etc. outfits
>he wants me to roleplay as a brothel femboy
>I put on the shitty Amazon bunny girl costume; I have a semi-puffy chest, but it's mostly empty so the top doesn't lie flat
>I get into the roleplay and we're both having a fun time
>think I hear a soft knock
>probably just the neighbor
>don't want to be paranoid and ruin the mood
>straddling him on the couch and making out
>for context, my mom treats knocking as a courtesy
>hear the door open and my mom's voice: "ANON! I have some leftovers for you—OH!"
>I'm straddling my bf in cutefishnets with bows on them and full makeup
>don't have time to react or come up with anything, so I just blurt out, "This is C!"
>he enthusiastically says, "Hi, ma'am!"
>she nonchalantly says, "Well, I'm going to leave this on the counter here and leave you two alone."
>on the way out, she says, "Make sure he wears a condom!"
>she leaves
>my bf tries to calm me down and we resume
>a while later, my phone buzzes
>it's a text from her saying she loves me no matter what but I should talk to my father eventually

>>45079397
awwww thats really cute

>>45079397
Thats sweet but also holy fuck that IS mortifying

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Forgot to attach layout in case any else asked again... lmao

>>45079408
She's a great parent if you ignore the whole lack of privacy things she has going on. She basically tells everyone everything, this was the only thing she didnt and instead she basically said if I didnt tell my dad she would...

>>45079455
Yeah I feel like that moment changed my mom's whole opinion of me

>>45074826

Ready to feel jealous?
>Beginning of 8th grade
>Got addicted to crossdressing over the summer because a couple of female friends would dress me up
>Never did it at home though, just at my friend’s house
>Sister has just moved away for college
>One entire wall of her bedroom is two wide closets next to each other with double doors
>Closets in my bedroom are the same way
>Mom decides to use my sister’s empty closets as storage for boxes and stuff
>Pretty much all the clothes in her closets that she didn’t take to college either got donated or thrown out
>Everything except for the best stuff however
>Two homecoming dresses, her junior prom dress, her senior prom dress, and two other formal dresses
>Mom moves those into MY CLOSETS
>They’re basically my dresses now
>Addicted to Adderall so stay up until 2-3 AM pretty much every school night already
>Am also rail thin because of the Adderall so have no problem fitting into a size 2
>Parents go to bed at 10PM every night
>My nightly routine is to wait until 11PM just to be safe, lock my door, and get dressed up
>Sister left behind plenty of bras and panties in her dresser so I keep a stash of those hidden away in a small duffle bag on a shelf in my closet
>Feel a little perverted about wearing her panties but have no other option
>Soon I get more confident and decide to add makeup to my nightly routine
>One of my female friends knows about my private crossdressing because I told her
>She gives me a ton of makeup, like way more than I even need
>Keep the makeup hidden in another bag in my closet
>Friend also gave me a circular mirror so I can sit at my desk while doing my makeup
>Have a big stash of makeup remover wipes
>Every night I put the used wipes in a big ziploc bag which I later throw away when the coast is clear
>Have a TV in my room so every night I put on a bra and panties, slip on a dress and do my makeup while watching TV
Cont.

>>45079585
>After a couple months I manage to get a wig and add that to the rotation so my life is basically perfect
>Friend gives me a bunch of hair accessories too
>Hair clips, barrettes, bows, ribbons
>Become really good at styling my wig
>Never once get caught or even arouse suspicions
>Eventually get a second wig

>>45079244
no way, i'm too scared of getting aids or murdered i even chickened out of accepting a date with a mtf girl because i'm afraid she will give me stds :(

>>45075172
same except 10 years

>>45079599
You can have fun and still be cautious. Honestly you should stereotype at least a little bit. No druggies and in general no low class people. You can get on stuff like prep too.

So far this is the best thread I’ve seen on this board in at least a year. These stories are great

>>45079659
For fucking real. This thread is great.

A major takeaway from some of these stories is that the secret to being a successful teenage crossdresser is to be just totally shameless about it. And also be skinny

>>45079626
the girl was a real missed opportunity (hsts with a normal life and career but she has a gay friend and is very active in trans and lgbt circles so i thought she must be in some degenerate gloryhole dark room sauna shit), i regret it all the time, i'm gonna end up like that guy who is too scared of the outside world and dies a virgin in that chekhov story :(

>>45079819
being fat is associated with poor outcomes in general

>>45078187
true story that event led to me finding /lgbt/ a decade ago but boymoding hadnt become the meta yet

>>45078693
I’m now thinking about that GF and getting teary-eyed, she was so cool and sweet about everything. It’s crazy that I even knew a girl like that at 15. I’d go to her house and she’d do my makeup and we’d wear her dresses and make out on her bed. But sadly for her making out is all I’d ever want to do. I really hope she’s doing well

>>45074826
>at summer camp
>counselers decided were doing a cross dressing day
>im the smallest boy so i swap with the smallest girl and some of the other girls need my clothes cause the boys are so big
>cute tank top and shorts, I shave my legs already and tank top shows off my freckles
>we do some random activities I’m having a great time other boys look embaressed
>some random woman on the activity we’re doing calls me cute
>best day ever
>we finish up take photos
>get told we’re gonna change back when we get back
>start trying to bargain and ask to keep doing it
>every one looks at me weird
>go back get changed and feel sad
2nd story that probably doesn’t count
>troon out 2 years later at 15
>boy mode at school
>3 months hrt go to anime convention with friends
>i girlmode and go by my girl name
>i actually crash into a class mate as she rounds the corner to leave the bathroom and i try to enter
>next day at class she turns around and keeps looking at me
>eventually asks if i was at con yesterday
>immediately respond what’s that
>she kinda glares and never brings it up again

>>45080023
going to cons is awesome but seeing a classmate sounds like worst nightmare LOL

>>45079397
>I tried to reduce the smutt
What? Whyyy?

It was every bit as mortifying as I hoped. 10/10. Please tell me there's more.

>on the way out, she says, "Make sure he wears a condom!"
Did he? Or did he rawdog it?

>>45080109
I can talk about the smut but I didnt want to be excessive and it was really relevant to my mom finding me out.

I preferred he didnt but he did specifically because my Mom said to... >->

I can write out what happened leading up to her coming and what happened after... I dont write smut though so it might be dry

>>45080249
You can probably lean literal and have it still be hot

does part of the cis afab fascination with gnc amabs relate to the fact that there is no longer a cultural prohibition on ftm crossdressing in the west?

>>45080249
>I can write out what happened leading up to her coming and what happened after...
Yes please!

>>45074826
>be me
>5’6” secret crossdresser Asian
>long time friend from Montana is coming
>hes 6’4 and genuinely a classically attractive straight guy
>he only knows me as just as straight bro
>he stays at my place
>we meet up with are mutual friends at a bar
>he passes out on the couch
>I go to my room
>when I’m drunk and high I always start feeling like being in doll mode
>start doing makeup
>get a nice lingerie outfit on to post on my cd hoefiles
>hear some faint sound behind me
>door latch spring sometimes allows the door to just open with the slightest effort
>hes there
>FUCK
>I’m in a wig and makeup all exposed
>my heart is racing
>he says sorry steps back and pulls the door shut
>”I just wanted to say the toilet is not working”
>fuck he’s right and I forgot to mention it
>”ok” I said
>”uhhh sorry”
>”it’s ok… please keep this to yourself”
>”of course. Can I open the door a little more to talk?”
>invite him in after I cover up
>can’t tell if he’s still too weirded out or not
>”is this new for you?”
>basically say no and generic blah blah
>he seems understanding
>he tries to lighten the mood by making a joke
>asks to see my nails (which are cheap shit)
>lay my hands out for him to see
>he pulls gently grabs my hand and pulls it towards him so he can see
>I lightly tighten my grip on his hand and gently pull towards me to see if he’s receptive
>he sits down next to me
>we both have the look in our eyes
>we start touching our inner thighs
>I pull his dick out and start blowing him
>he pulls my panties off
>proceeds to fuck me from behind on the bed
>insane orgasm
>most I’ve ever coomed in my life at that point
>pretend nothing happened next day :(

>>45080934
>>most I’ve ever coomed in my life at that point
Did it make a mess?

>>45081118
Absolutely. It was one those times where I was still hard for a while after cumming too. Like it still felt good stroking even after cumming because that’s how turned in I was.

>>45081145
Did you cum a second time?

>>45080347
No it's because they find joy in mocking you for not being beautiful and feminine like them. Crossdressing highlights all of your most masculine features.

>>45075249
This. I dress 100% fem at home and just throw on a hoodie whenever i need to video call (work from home). But i'm also an Eastern Eurofag, so there's that.

>>45081165
Only by myself. He went to bed. I couldn’t tell if that was his first time with a crossdresser before.

>>45078882
Incel to tranny.
Brutal

>>suddenly my ex arrives with her new bf
>>he's a foot taller than me and NOT in a dress
Pantsied.
Sissified.
It's fucking over for incels.

>>45081253
has... has it ever *not* been over for incels?

>>45081178
Well thank you for sharing such a hot story. I'm going to go touch myself to it.

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>>45081257
50 years ago there weren't even incels so yeah.

But the hat just had to go flying

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>>45084443

>>45080018
No fucking way this is real.

>>45081253
I know it's not the thread for it but damn fucking a tranny in front of their ex from before they transitioned would be hot

>>45080054
sounds like one of the good ones

>>45081265
I wish my other stories were this hot. But they’re all really just sex where I cum a lot.

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>be me
>repper
>crossdressed 100 of times, often with people in the same house and doors unable to be locked
>never been caught
>sister was surprised im a faggot when i drunkenly came out to her

>>45075121
True I've never crossdressed in my life.

>>45081172
So true I had lots of female friends that wanted to feminize me earlier in my transition that ended up hating me when hrt made me prettier than them.

>be me
>with my younger cousin
>we are both girls
>on vacation
>swimming in a small pool
> two british girls join us
>they greet us
>they start to sing ‘Sigma Boy’ song
>one girl points at another and says that girl has crush on my cousin (ma cousin is hella homophobic btw)
>they ask where we from
>we reply
> one girl asks if we have bellybuttons
>i say yea?
> then she dives in water to see or bellybuttons
>they ask if we like to eat horses
>then they ask a lot how english words sound in my native language
>me annoyed
>one of those girls admits she is lesbian and has a gf
>they ask us whether we know what word ‘lesbian’ is
>my cousin becomes hella akward
>me pissed off because it felt like they are bithching with us, like OF FUCKING COURSE WE KNOW WHAT THAT MEANS
>we decide to go away like losers from a pool

>>45081172
That’s only true in certain contexts. For example a major reason women enjoy dressing up younger gay boys is because they often can pass as girls

>>45081821
shut the fuck up you fucking LIAR. that never happens. it never happened to me and i looked like a girl until puberty. fuck your gay lies you fucking gay, gay liar

>>45074826
hey cool thread! crossdresser here
I actually just went out in girlmode for the first time and it was liberating.
Went with two local CD friends to a fancy lgbtq dress event, checked into hotel as guys left in fancy dresses, we looked decent (not passable, well maybe I pass from a far lol)
met a lot of likeminded ppl and got a few compliments here and there
felt very relaxing and liberating being a girl for one evening, will propably do it again with them, lets see how things progress now

>>45081835
Sorry you missed out…

>>45081941
stop the lies, lyin' don

>>45075121
It’s been largely forgotten that back in the 90s/2000s there were gay crossdressers who could entirely pass as women without surgery or hormones. They were just naturally feminine and talented at makeup. And crossdressing was just like a weekend hobby they did for going out to bars and clubs

>>45082592
where have they all gone? i thought testosterone levels were lower than ever

>>45082856
Transitioned into well-adjusted stealth women

>>45074826
>be a 15 year old gay twink
>been crossdressing with my older sister (17) for years
>she takes me to a Halloween party at someone’s huge mansion
>I’m wearing a little black dress, heels, and a shoulder length wig with a red devil horn headband
>sister does a 10/10 job on my makeup
>I’m looking really hot NGL
>get separated from my sister at the party
>some really drunk guy starts flirting with me
>I flirt with him back
>after a few minutes of talking he pulls me into a room and shuts the door
>holy shit I seduced a guy
>start kissing and I ask if he knows I’m a boy
>he just says “that’s cool” and we make out and he feels me up
>after 5-10 minutes of this he says “i have to piss” and tells me to stay there
>he leaves the room and I sit in a chair
>wait for like 15 minutes and realize he’s not coming back
>this was the first time I ever fooled around with a guy
>feel embarrassed
>leave the room and go find my sister, tell her what happened
>get really drunk
>sister takes me home
>I throw up and cry

>>45082592
in the paris is burning documentary there were literally tranny drag queens taking hormones who wanted to go stealth lol. theres nothing new under the sun

>>45082905
stop the lies, lyin' don

>>45074826
>sad stories
I tried it once, when i was ~14. Did it with people i concidered to be close friends. They took a photo of me and spread it around for a laugh. It was last couple months of middle school so at least i had that. Never tried it again. Never got the confidence for it.

>>45082933
The difference between this and the success stories is that you probably looked like a younghon instead of being a passoid.
Fee milimeters of bone. All there is to it.

>>45082949
the world is not your gay sissy anime. that isnt how it works

>>45083001
Coping incel

>>45083019
lole my bf and i had sex lit-ra-ly two days ago. women and girls (cis afabs) actually hate gnc amabs and would never participate in this fetishy "induction into femininity". the whole thing is a psyop designed to deceive gnc amabs into being vulnerable for the sake of later humiliation

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>>45083160 >>45083214 >>45084381 >>45084398

>>45074826

both my mom and dad found out about my crossdressing and e-grooming/whoring, but surprisingly they didn't ground me or really prevent me from engaging in it later

>be 15-16
>discover AGP as a concept and realise it fits me perfectly (also genuinely homosexual though)
>parents go out one day
>mom's pretty layered white dress is just hanging near her wardrobe, decide to wear it
>i look so hot
>decide to take it for myself and keep it in an old school backpack
>wear it every night in my room as i'm allowed to lock it at night
>sleep schedule is destroyed because i stay awake until 2:30-3:00 AM, completely enamoured by the dress (either sexually or in some other way)
>eventually steal some lingerie too, and some other stuff
>the bras and panties feel so good
>eventually start sending pictures of myself to predators on discord like an idiot
>mom must have gotten suspicious, because she goes through my phone and eventually sees EVERYTHING while i'm ar school
>given "the talk", surprisingly she's a libtard but wants me to either FULLY troon out or fully be a manly moid, no GNC
>wimp out and say it was just weird teenage hormones and i don't want to be a girl (a lie)
>she buys it
>doesn't ask for the clothes back for some reason so nothing changes and i continue my activities but more secretly this time
>dad later asks who i was messaging on "that app"
>say it was AI, he buys it with a huge sigh of relief (LMAO?)
>eventually realise how fucked up doing this on discord is and quit the app
>troon out recently as an adult (~3 years later)
>never gave up those clothes though
>still fit in them

dad also separately gave me the later but was probably too awkward to spell things out explicitly like my mom did. i was caught stealing her clothes again but nothing came of it the second time too. i never stole clothes after the second time but i did seriously consider taking a pair or two of my cousin's lingerie while on vacation. don't really regret any of this at all

I dont crossdress. I am a woman

>>45083095
the thrill of stealing/wearing my mom's clothes was like a drug for me. honestly i'm surprised by how fervently i did this. i'm fervent in other parts of my life too but it was like i was possessed when in this head-space. i lost control and could do nothing but heed my desires.

i can nominally acknowledge that this was questionable but i don't *feel* that it was wrong at all. i would do it again. in fact i regret not doing it more. i don't know what's wrong with me but i guess i'm like de Sade petioning that Nature crafted me this way and i have no free will to act otherwise

>>45083095
How old are you rn that at 15-16 you said you were talking to AI.

>>45083214
18 and 3 months

>>45083302
Nigga why are you getting groomed. Youre like that one gag character from American Dad that keeps getting molested. Go play the binding of isaac and drink some rum+coke nigga.

>>45079588
Can tell you’re either gay or HSTS by your excitement at wearing homecoming dresses and no mention of gooning lol

>>45083386
i'm not anymore and can't since i'm 18 now but i feel mostly apathetic to me being groomed, like i *knew* what i was getting myself into. i willingly searched for those kinds of spaces. i wouldn't ever drink or do drugs though i don't trust myself to not ruin my life if i ever got ensnared by those things

Since everyone else is sharing Halloween stories
>9 years old
>amy winehouse just died a few months earlier
>my very eccentric mother decides to dress me up like her for Halloween
>buys me a dress and long black wig
>puts temporary tattoos on my arms
>does my makeup in amy’s signature style
>look really pretty
>takes me to a party at her friend’s house
>get tons of attention
>REALLY enjoy it
>end of the night I don’t want to take the dress off
>haven’t been the same since

>>45081973
“I’m bitter that it didn’t happen to me so clearly it didn’t happen to anyone else”

My mom said i used to be into wearing dresses as a small child (5yo or smaller.) but i recall.none of it and doubt it even happened.

>>45084040
the lyin' don internet defense force

>>45079819
that's it I think. it's sad how looking back how shameful I was, with the benefit of hindsight my parents were pretty lib and would have been accepting. I almost wish I got caught more.
>>45083095
I probably could write an essay about how young trannies are especially vulnerable to grooming. its sad honestly, we only wanted the validation. it seems everyone I know has a story like this

>>45083095
>rejected trooning young with supportive parents to continue being a pathetic cd-er

>friends with girl
>girl dresses me up as a girl for fun
>I like it but can't explain why
>make a pass at her, ruin our friendship
>rep for 6 years
I hate myself so fucking much

>>45081298
It really happened, honestly I don’t even blame you for not believing it (though maybe you do) because I know this is like an ideal situation for so many people but almost never happens irl

>>45084398
i look mostly the same as i did when younger (it's only been 2-3 years and puberty was forgiving), but i wouldn't exactly call them "accepting", they just don't think in the same way most Americans do and it's just as likely they would've tried to convert me (in the aforementioned "later talk" dad gave me he seemingly implied that there was medicine - probably testosterone - that could supposedly help me fight against these urges)

plus i'm not willing to undergo the social humiliation this would have brought from my wider family anyway, my parents don't hide ANYTHING from my wider family and i know that they mentioned my being caught to my aunts/uncles in some way, though my cousins seem to be unaware so it didn't affect me much outside of just wanting to ignore my extended family (not like they can pull me aside like my parents could)

>>45084381
>young trannies are especially vulnerable to grooming. its sad honestly, we only wanted the validation.

yeah, i feel apathetic to what happened to me but i know i should actually be shocked and appalled. it was a really dark and miserable time for me and my extreme desires were my mind's way of balancing the extreme suffering, or at least that's how i like to conceptualise it. i wonder how much healthier i'd be mentally if i had a community around me to sate the desire i have to be understood and accepted and cherished

also estrogenboy is a name i use online so for a second i thought i was tripfagging without having any memory of ever doing so XP

>7 years old
>out clothes shopping with mom
>wander into the girls section and start admiring the pretty dresses
>mom sees and asks if I want her to buy me one
>feel embarrassed and say no
>mom asks are you sure
>say yes
>immediately regret it
>regularly think about that moment over the next few years
>finally get to wear a dress at age 10 so I really shouldn’t complain

>>45084381
Also I guess it depends on what your appearance and personality already is. If everyone already knows you as a femme gay boy, being like “I want to wear girl’s clothes” isn’t exactly shocking

>>45084632
can't believe you didn't recognize /tttt/'s very own estrogenizedboy

i really like this, this should be a recurring thread, i feel a lot of kinship with the people here

>>45085009
Before covid hit these used to be some of the most popular threads on the board and then something changed

>>45085412
Nobody was able to crossdress in private anymore

>>45074826
I crossdressed a bunch of times as a kid but here’s the story of my first time

>be a faggy 11 year old
>on summer break
>sign up for a daytime tennis camp at a nearby rec center
>the boys are mean to me for being a scrawny little unathletic fag
>befriend a girl at the camp who is my same age
>she sucks at tennis too
>we bond over being skinny and bad at sports
>find out she lives just a few blocks from me
>invites me over to go swimming in her pool
>we become good friends and I go over to her house a lot
>her older sister is 13 and she teases me a lot for being so feminine but not really in a mean way
>one day we’re watching clueless in her finished basement
>her sister has a friend over too
>they go into the storage/laundry room
>can hear them giggling about something
>they call my friend into the room
>wtf are they doing
>friend calls me over
>walk into the room
>the girls are standing at a long rack full of costume dresses
>her sister says they want to dress me up like a princess
>friend says she’ll get dressed up with me too and it will be fun
>says they both like to go as princesses every year for Halloween and that’s why they have so many costumes and she never has an excuse to wear them
>say okay
>asks which princess I want to dress up as
>uhh Cinderella I guess
>she flips through her multiple Cinderella dresses and hands me one
>go around the corner to have some privacy while I change
>take off my clothes and realize I don’t know how to put on a dress
>her sister comes over and helps me
>it feels surprisingly nice and comfy
>friend puts on a Belle costume
1/2

>>45085742
>her sister takes us upstairs to her bedroom
>she and her friend put makeup on us
>go back to the basement and we put wigs on
>sister and her friend laugh because they can tell how much I’m enjoying it
>friend tells me not to feel embarrassed
>amazingly I don’t
>we finish watching clueless while dressed like princesses
>finish movie and hang out for a while longer while still dressed up
>eventually I need to go home
>change out of the dress and her sister removes my makeup
>start walking home
>realize I like dressing up like a girl and want to do it again

>>45081433
So...hot lolol

I only crossdressed in secret so my conservative mother wouldnt find out still even as a boymoder of many years ive never dressed as a girl :/

this isnt really cd cuz I was technicly out
>first day of school (12th grade) post trooning
>name changed in system, but people don't know
>wear a dress with a biker jacket and probably some horrible boots I don't recall.
>extremely nervous, practically not able to talk, no voice training
>walk in to class exactly on time so nobody can talk to me or notices
>after the period ends I notice this metal head guy wearing a kilt
>he clearly thinks we are the same.
>"hey deadname/anon, you like skirts too, badass"
>go cry
>very quickly tone down my outfits over the next month, from leggings sometimes to just skinny jeans.
>eventually just wear my boy clothes again
>boymode from then until now and into the future (8 years)

Recurring theme I’ve noticed is femme gay kid + liberal single mom + exclusively female friends= dressing like a girl. Whether this is good or bad depends entirely on your worldview

>>45086795
jfmstl

>>45086795
You can either have males in your life, or you get to wear dresses and makeup at age 12. What do you choose

>>45086930
I didnt get either. why would u want males in ur life

>>45086930
To be fair if you’re a femme gay kid you might as well choose the latter, your childhood will be more fun

i'm 16 and just two months ago I tried out my mom's clothes and put on some makeup and when I looked in the mirror, I thought I looked nice. But then I curled on the floor and crying and shit. saying how i didn't want to be a son to my parents anymore and stuff like that. I also got caught by my mom once, but she didn't find out and since then just been trying to live in content.

>>45087168
you must be 18+ to use this website

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I've been wearing moms panties and clothes since I was like 12-13 ish. Every time I would get the house to myself I would go to my parents room and put her panties and bra on, sometime her dresses and jeans. I'll pose and strip at first but then I'll started pretending to get fucked by my dad and come up and act out a bunch of shit. Like" fuck me like you fuck mom" and I'll masturbate and moan. Sometimes I'll put on some girl slut music and dance, strip pretending I was doing it for my dad. I remember when I was 14 on my older brothers High School graduation. They had to go pick some people up and I had the house to myself. I was wearing my mom's pink panties and her tight mom jeans and I'll bending over checking out my ass and rubbing myself while moaning for my dad. They came home faster than I thought. And I didn't have enough time to take it all off. So I grabbed my clothes and went into their bathroom. Put my clothes on but I was still wearing the pink panties because I was scared they would see them as I make my way into my room. Use a bath towel to hid my mom's jeans and pretended I got out of the shower. They were late for the graduation so we had to leave quick. So I went to my brother's graduation wearing my mom's pink panties under my pants, and I had to sit next to my dad the whole time after I just fantasize about being his whore and screaming his name as I jacked off. It was a weird feeling. I'm in my 30s and I still crossdress and do the same from time to time.

One time I wore a dress and then my whole family kept encouraging me and then it felt really weird

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>>45087644

>>45074826
Not really a story but I used to cross dress alone in my room in highschool. I just bought tons of cheap clothes of AliExpress and I would just sit in my room or play games. I bought a brest plate one and I cried for like an hr then threw it away. A girl I was talking to ask to see pictures of me dressed up and just kinda made a few awkward jokes then ghosted me. I got caught a bunch near the end of it because my mom would go through my stuff and it got to a point where I was grounded for like 3 months and I just gave up on it all and pretend to be normal until I moved out. I got hrt and have been on it for 3 years and I can count the times I've worn womens clothing since then on 2 hand. Ik it's pathetic but I miss those times because it genuinely felt like I was discovering something about myself and moving towards a happier life. Now I've just kinda stagnated and hid in my manmoder shaped hole. I think I'm gonna detrans. I have a lab I need to get done before I get a refill on my prescription and I only have like 3 days left of pills and its at least a week till I can get labs. Oh well. It's not like it made me any less of a moid anyway.

>>45087616
at least stay on hrt. manmoding beats the alternative

>>45079303
100000% actually
>>45081253
definitely not an incel lol

i remember posting a pic of me with makeup, probably my first time wearing some too at 18 asking if i had potential and got negative responses and ended up starting hrt 1 1/2 years later.

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>>45085009
>>45085412
>>45085617
making a new thread about this would fill me with a strong sense of dread about my past so one of the anons here please do it after this one dies out ^_^

>>45078068
I love (You)

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>>45088260 >>45088662

>>45080269
>>45080556
Since the threads still up I wrote it out, not a writer and its been a couple years, be gentle
Context here: >>45079397


>bf knocks on the door
>answer it, he looks at me, tells me I look cute with my oversized tee and makeup and kisses my forehead, then my lips
>"I gotta grab my monitor, can you take this in?"
>he hands me his PC and I set it next to the empty desk, a few seconds later he brings the monitor in and sets up
>I'm honestly a bit bratty when I'm gaming and he's pretty nonchalant
>we play like 2-3 games of counter strike
>I play terribly and he plays well
>he's full of himself so I start teasing him to throw him off
>mostly cringe stuff like "senpai's cock is so big", "gulp! I hope I don't get pregnant", you get the point
>start calling him sir/daddy/milord/whatever after a while and it starts taking a toll
>we finish a game and he looks over at me with clear annoyance in his eyes
>"apologies sir," I say, and salute him like an idiot
>he cracks a small smile, doesn't say anything, and moves over to the couch
>"I think I need a break from gaming"
>I go sit next to him and lean against him, "well, what do you want to do?"
>"what happened to that annoying brat?"
>I just giggle and shrug
>his tone changes, "so now you're pretending to be a good boy after being a brat for the past hour"
>"nooooo I AM good"
>"you're a brat"
>"no I'm not"
>we go back and forth like this for a bit, touching each other softly
>"if I was a brat, would I do this?" I tease, and suck on his finger
>"yes you would!"
>I giggle, he just grins
>he changes his tone, "can you wear something for me?"
>like what
>"your bunny suit"
>nod and run to the bedroom to change, heart racing obviously
>when I come back he's leaning back on the couch, arms draped over the top like some mafia boss

Cont.

>>45088255
>"are you the new hire I ordered?"
>oh god, I'm cringing, he's committed to rping
>"...yes sir," I say, unable to hold back my smirk
>"I heard you're a bit of a headache for management"
>oh, I get what he wants me to do
>I scowl at him with my hand on my hip, "well, do you want me or not?"
>to be honest I think I got him more interested by doing that
>"be a good boy and bring me some wine"
>I bring him pineapple cider since it's all I have
>try to arch my back and pour it delicately into a shitty cheap glass
>he takes a slow sip, swirls the glass, "ahhh"
>I just stare at him, acting unimpressed while trying not to laugh
>he puts his hand on my thigh, right below my ass, "good boy"
>really turned on, but I pretend to hate it
>"what are you doing?" I say, as coldly as I can
>"just checking out what I paid for"
>I almost laugh from embarrassment, "well obviously, I wouldn't be here otherwise"
>I start walking off to put away the empty bottle, but he grabs my arm and roughly pulls me down onto the couch
>I'm wearing heels as part of the costume and one falls off as I collapse onto the couch awkwardly
>he breaks character to apologize, "oh my bad, you okay?"
>I decide to stay in character, "you break it, you buy it, SIR"
>"and if I break you?" (I had a mindbreak fetish, so he knew exactly what he was doing)
>I don't have a retort and I'm really horny and flustered, so I avert my eyes
>he leans in and gently says into my ear, "come sit on your master's lap"
>I break character, "god, you're so evil"
>he just laughs while I straddle him
>he kisses me gently, "you lost so easily"
>I'm half pissed that he pushed all my buttons, so I pout a little
>he tilts my chin up and kisses me again, and this time he doesn't pull back
>I wrap my arms around his neck while he holds my waist
>I start grinding against him and he teases my nipples a little
>hear soft knocking, which takes me out of it a little, but we keep going
>door opens, we stop and my Mom walks in

My mom wasn't very fem and was fat. She only had one pair a clothing, an old nightgown hidden in the back of her closest, that I ever bothered to try on. I'd also use her lipstick, which she never wore after I was born.

Otherwise, I made do with a black cape I had from an old Halloween costume. I used pins to make it into a dress.

When I got my license, I would drove 30 minutes to the closest Walmart and perused the Halloween isle (I never got the courage to go into the women's section). I bought some striped tights and some nail polish that I would wear when my parents weren't home.

When I got older and had my own place (after college) I bought some women's lounge wear (nothing revealing) and would wear that around the house.

I'm in my early 30s now. Looking back, shit really sucked. I cross dressed on and off for most of life. Only just started my transition last year.

>>45088260
Super hot. Shame on him using condom afters loloo

>>45088255
>>45088260
Based. Thanks, Nona.

If you don't mind a follow-up, how was the talk with your mom after?

>>45074826
i don't have any FUN stories... just kind of sad pathetic lonely ones that i don't wanna dwell on
thinking about teen crossie days just makes me fucking sad

>>45088688
Anything you want to get off your chest?

>>45088734
idk. all my youthful crossdressing experiences felt kind of isolating and melancholy. it took way too long to actually come out and transition, long enough i screwed myself out of being able to dress young and cute while actually being young and cute. i'm out and officially "a woman" but i don't even dress feminine like i always hoped i'd get to. just a great feeling of "is that all there is?"
sorry to be a downer

>>45088752
>but i don't even dress feminine like i always hoped i'd get to.
Don't let your dreams die, Nona. You should dress feminine.

So jealous of people like >>45079008 who were brave enough to go out in public all dressed up when they were young enough to naturally pass

>>45088662
She basically just said she loves me no matter what and wants me happy. Lots of crying from me. Same with my dad but more awkward.

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>>45088260
>door opens, we stop and my mom walks in

>>45089781
>Same with my dad but more awkward.
Yeah? What happened?

>>45088264
>My mom wasn't very fem and was fat.
lol same, i would actually get my mom's clothing sometimes as handmedowns but it was all stuff like t-shirts and sweatpants that were massive on me.

>>45090538
This sounds kind of mean but I’m so glad my mom was thin and I didn’t have any fat female relatives. Fat women grossed me out so much when I was a kid. I probably wouldn’t even have been comfortable expressing femininity if I were surrounded by fat women

>>45090830
nah i get it. not to get too drama queeny but i basically ruined my life repressing not just femininity but any kind of personality at all.