Jizz

[CD]Line posing in bed. (also posted on crossdresser)

gonewild, Tgirls

I never knew crossdressing could be such fun. (NSFW)

GoneWildCD

not really nsfw, but maybe too much for the regular /r/crossdressing

GoneWildCD

All smiles (crosspost /r/crossdressing)

traps

Teen Crossdresser! 1st post got 17k views. this is my 2nd post!

GoneWildCD

Any love for a well-tucked crossdresser/sissy?

Sissies

I love crossdressing while wearing my diapers!

ABDL

A first crossdressing try. What do you think about it?

GoneWildCD

sparkly broke club slut [crossdress] [forced]

xxxcaptions

working the streets for fun [sissy] [crossdress]

xxxcaptions

open door policy [crossdress] [forced] [gif]

xxxcaptions

Modeling on the bathroom floor [x-post r/crossdressing]

GoneWildCD

Amateur Crossdresser. Sexy Pics. (;

GoneWildCD

Second (failed? :o ) attempt to crossdress

GoneWildCD, FemBoys, Sissies

Had to delete my pictures on /r/crossdressing today. So here, have another one on the house, /r/sissies!

Sissies

Red Corset. [x-post from r/crossdressing] Enjoy!

GoneWildCD, traps

sissy crossdresser first post. Let me know what you think ;)

Sissy, GoneWildCD, traps, Sissies

First outfit, new to crossdressing, hella nervous, hope yall like

LGBTGoneWild, GoneWildCD

New to this! Trying to crossdress while living with parents (18 years old). Kik - inneedofdaddy

Sissies

Judging skirt lengths [crossdressing] [punishment]

xxxcaptions

After coming out in /r/crossdressing two days ago I decided I had to go a little more wild ;)

GoneWildCD, FemBoys

[M] Tiger experimenting with crossdressing - vu06

FurrySoftcore

I'm a crossdresser and I can lick all around my tip.

autofellatio

I want to be a sissy. What do you think about my first time crossdressing? Please be gentle :)

GoneWildCD

Proud Crossdresser Slut

Sissyperfection

sissy crossdresser in short skirt and heels...

GoneWildCD, Sissies

Posted some tame ones in /r/crossdressing. Felt like showing off a bit more skin. ;)

GoneWildCD

[M] Oh, Hello There [Meru13] [Domination] [Crossdressing] [Implied Rape] [Request]

yiffcaptions, hentaicaptions

[FFM] The girl club [iskra] [Crossdressing]

yiffcaptions

First time crossdressing... I think it suits me [M, 18]

GoneWildCD

Cress Crossdressing [M]

FurrySoftcore

Akihisa can crossdress too!

CuteTraps

my favorite crossdressing time

DarlingInTheFranxx

What happens when you finally get caught crossdressing

Sissyperfection

Anyone up for a MILF crossdresser :)

Asiantraps, Sissies

Does it still count as crossdressing if all I have on is kneesocks and a collar?

GoneWildCD

Technically not crossdressing here but i'm told I have a cute tummy ?

FemBoys

Hit me up if you're a crossdresser x?

GoneWildCD

Women's Studies [crossdressing]

xxxcaptions, SissyCaptionStories, Sissyperfection, MEFetishism, genderotica

All are welcome to pm women trans. Crossdressers, traps

MassiveCock

Not sure how this sub likes crossdressing, but was feeling cute in my new nighty and decided to post again for the first time in a while

DudesInDiapers

Too wholesome for GoneWild and too NSFW for r/crossdressing!

GoneMildCD

I'm super into hucow and breeding. Especially being turned into a cow and teased the whole time about how big my breasts are getting and how I'm just a "dumb, fat cow, only good for breeding" (i'm also a crossdresser)

KINK

Rethinking This Break-Up [Hypnosis] [Crossdressing] [Femdom] [Hentai]

xxxcaptions, hypnocaptions, hentaicaptions

Matching! [Chastity] [Crossdressing]

xxxcaptions, keyholdercaptions

What's That Saying About Old Flames And Being Hard? [Crossdressing] [Sexting]

xxxcaptions, u_A-Great-Disguise

Does it still count as crossdressing if I’m naked??

GoneWildCD

22 New fan of the sub and we'll this happened browsing. I love frotting/sword fighting and crossdressing. Snap me @ strtown!

Mexicancocks

Can you crossdress when your barely dressed, I think so hehe

GoneWildCD

Cure Macaron Cos-flation Sequence {M Crossdressing Feminization Rubber/Latex Kigurumi of Cure Macaron from Pretty Cure} from FieryJinx

transformation

[Feminization] Animal Crossdressing by Slemka

Inanimate_TFs

Too weak even to punish normally.. [Wrestling][Scat][Pegging][Humiliation][Crossdressing]

Grossdom_academy

New to crossdressing, honest thoughts and opinions? ?

GoneWildCD

My mom came home early one day and caught me crossdressing in her clothes. I was so humiliated, but she smiled and said, "You know, I've always wanted a daughter." She took me to see her friend who turned out to be a powerful witch, and had me permanently

bodyswap

A Year's Difference [Femdom] [Chastity] [Feminization] [Sissy] [Forced-Bi] [Cuckold] [Crossdressing]

xxxcaptions, keyholdercaptions, cuckoldcaptions, u_moonlight_unknown, u_A-Great-Disguise

Massive Dick Strong Latin Crossdresser Jerks Off

CDporn, thedirtycollection, stronglatintranscds

[F/s] Papa, Boku no Onna ni Natte (wholesome story about crossdressing father and son)

IncestDoujinshi

Please, I'll do anything...[crossdressing]

keyholdercaptions

As a teenager, I became so addicted to crossdressing that I wore my sister's clothes and emptied out her entire pantyhose drawer putting them all over the bed. Unfortunately, I fell asleep like that. When I woke up, my sister was yelling at me calling me

EffeminacyAndFaggotry

23 Georgia crossdresser looking for friends / fun. would I make a good secretary?

sissypersonals