Jizz

Ill Cross-dress and you set up the camera!

yiff

Cross Dressing Fap Game "For sissies that don't want stuff up their butt."

faproulette

First time post! I have large boobs for a guy and can't get enough of cross dressing! Go easy! =P

GoneWildCD

Cross dressing is my new hobby! Ladyboner worthy?

ladybonersgw

Cross dressing Soarin anybody? (M)

ClopClop

Cross Dressing, Alice in wonderland crossover, gay pony porn (MM) AKA the best picture ever. by Hasana - Chan

ClopClop

If you are tempted to cross dress I would suggest some tighter shorts underneath that skirt.....

funny

Cross-dressing nurse Spongebob with enormous boner and a syringe up his bum

rule34roots

First time cross-dressing [19/m]

GoneWildCD, Sissies

When cross dressing goes wrong - NSFW

cringepics

Humiliate this cross dressing sissy slut (more in comments)

FemdomHumiliation, Sissy_humiliation

Haven't cross dressed in ages! What do you think?

GoneWildCD

Having my first go at cross dressing... I can't say the same for anal play! [cd]

BDSMGW

I am so tired of keeping my cross dressing secret.

GoneWildCD

paying the rent [cross-dressing]

xxxcaptions

[50/50] Sexy girl outside in the summertime (NSFW) | Cross-dressed man outside in the summertime (NSFW)

FiftyFifty

A little cross dressing fun

LoliShota

Bianca Anchietta - Cross-dress (it's not what it sounds like)

tightdresses

I love cross dressing!

GoneWildCD

Misha Cross dressed in red

ginger, assinthong, tattooed_redheads

I made this so you can masturbate to a caption that doesn't include animals, cheating, cross-dressing, hypnosis, shit, or urine. Remember to clean up your semen afterwards. [Maid Costume] [Female Perspective]

xxxcaptions

More from first time cross dressing

traps

Does a birthday suit count as cross dressing?

GoneWildCD

Diapered, cross dressing, & pajamas, oh my! (m)

ABDL

Need help finding this doujin/manga most likely about a guy cross-dressing and programming.

manga

cross dressing fun ;)

GaybrosGoneWild

Why? Oh. That's why. [Humiliation] [Cross-dressing]

xxxcaptions

Josou Seme or cross dressing top is a relatively new named sub-genre of yaoi which features a male character in women's clothing, appears rather feminine or young, much like the stereotypical uke

yaoi

Dressing up and watching some cross dress porn!

crossdressing

Not exactly cross-DRESSED....(=

GoneWildCD

New to Cross Dressing, is anal better in a skirt, or without a skirt?

GoneWildCD

One of the fetishes that I have not gotten a chance to try out is cross-dressing ?

AsiansGoneWild

Cross Dressing Witch. ?

DeliciousTraps, traphentai

This is my first day posting as a cross-dressing boy. I want to post more!

GoneMildCD, Sissies

Cross Dressing, hmu for kik

FuckingTweakers

Would thiss till be considered cross dressing?

GoneWildCD, Sissies

Been getting a little into cross-dressing recently, what do you think? ?

GoneWildCD

cant get enough of cross dressing~

Asiantraps, Sissies

I was listening to music while taking a bunch of new pics and this is the moment my roommate’s gf came home and caught me cross dressing

crossdressing

Cross dressing when no one is looking except....

Sissies, FemBoys, traps

Girls Suck, Boys Fuck [Femboy][RESCUED][Cross-dressing][Convoluted Narrative]

hentaicaptions

Dressing up like a girl for my buds is so hot. I’ve been working out just to make my ass as hot as possible. Kik contranym. To be clear: I am cross dressing

jobuds

Who Said Boys Can't Get Brands? [Trap][BRANDED][Cross-Dressing][MtG Caption][Convoluted Narrative]

hentaicaptions

Cross-dressing always makes my cage shrink! ?

u_SissyStephaniex, GoneWildCD

Used inflatable cross-dressing vagina pants

BrandNewSentence

Who else loves Link cross-dressing? ;) I drew his Gerudo outfit for a Patron

yaoi

Sleeper-Cell Cross-Dressing Slut [M Femboy Feminization; Corruption/Hypnosis] (FanterFane)

transformation, DeliciousTraps, traphentai

Isn't it nice at the end of a cross dressing comic the character realizes they're trans?

traaaaaaannnnnnnnnns

Cross-dressing with a futa girlfriend went further than expected [Futadom][Cross-Dressing][Anal] (Repost since I messed up the link. Sorry :P )

hentaicaptions, HentaiCity, Futadomworld, u_elizabethsissybottom

She comes home with a new bikini, but it's not for her... [Cross-dressing][Gentle Femdom]

hentaicaptions, HentaiCity

A soft dom is patient with her new sub. [Gentle Femdom][Cross-Dressing][Oral]

hentaicaptions, HentaiCity

LF Mono source: multiple characters, school, cross dressing

HentaiSource

Cross-dressing with a futa girlfriend went further than expected [Futadom][Cross-Dressing][Anal] (Repost since I messed up the link. Sorry :P )

Futadomworld

Dance class (cross dressing) (Humiliation)

Futadomworld

Cross-dressing soiling

HentaiScat

「A Boy Who Is Too Gullible to Realize That He Is Being Humiliated by Cross-Dressing」 [M Femboy Feminization] by ysdo968

transformation

「A Cross-Dressing Boy Made to Understand Women Through Feminization」 [MTF/TGTF; Feminization] by Amulai and moroheiya_farm

transformation

China Dress Jeanne & Jalter

thighdeology, AnimeBooty, grailwhores, u_blake_cross, u_CheetahSperm18

SEXY CROSS DRESSING SISSY pulls his pants half down to show you his ASSHOLE! Damn that motherfucker looks dark and pretty! His balls look cute too! I will fuck him in his ass while I jack his dick off! Im going to make sure he cums! NO SURGERY just a guy

DogHoes, randomtgirl, Seehimfuck, SexyShemales, shemaledepot, sissyneeds, TgirlModels, TrannyPorn, transanal, TRANSDREAMS, Transex, TransBodies, TransFeet, TransNudesClub, TransSnapchat, Tsasshole, TsAssholeBehindThong, TSDomme, TSLingerie, TsObession, tspee, tsporn

Cross dressing pegging[FOTD #507]

HemdomBlog, u_BlaBlaBla1913