Jizz

My sister, not dressed as Link

ass

SO. . .our night basically consisted of me dressed as schoolgirl and getting fucked, and him getting a blowjob and a foot massage. (F) x

gonewild

Three girls one kiss, [f]rom dressing as Marilyn at Halloween

GoneWildPlus

Barefoot girl dressed as a dinosaur from /r/pics

feet

Since everyone liked my Smokey the Bear strip, how do you like me dressed as a bear?

ladybonersgw

Classic Brit boob model Debee Ashby (un)dressed as Cleopatra

VintageBabes

Now I understand why you wanted me to dress as a maid, Brother- you never said I was going to have a mess to clean up

DirtyFamilyPhotos

Petra dressed as a French maid

ShingekiNoHentai

Looking for a new dress as clearly I have nothing to wear.

Sissies

Lana dressed as Bloodrayne

nsfwcosplay

Fluttershy and Celestia are dressed as sexy witches for Halloween(artist Sundown)

FapFap

Lucy dressed as a doll

LatexLucy

Brooke adams dressed as Harley Quinn made me so hard

WrestleFap

Kitty Lynn dressed as a sexy maid

kittylynn

Fanart I did of Lucoa dressed as Kukulkan from Smite, another wind serpent.

DragonMaid, MonsterGirl

Two foot loving girls dressed as angel and nun (more in comments)

Feet_NSFW

Riri dressed as an expensive whore

JerkOffToCelebs

Shot a load to my mates daughter on halloween, dressed as Khaleesi

JizzedToThis

Bai Ling dressed as Leeloo

areolapeaks

I[f] I dress as a christmas tree, will you mount me and put me on display?

gonewild

Wrong holiday, but enjoy a girl dressed as a demon on the toilet anyway

GirlsOnTheToilet

Norwegian Senior BBW dressed as a nurse

BBW

Ava Doll dressed as Harley

BBW

Maisie Williams dressed as a school girl is so fucking hot! I want to hike up her skirt and spank her before fucking her tight little holes!

celebJObuds

I get so hard when I see Angela Kinsey dressed as a nurse in the Office. She seems like the very naughty type behind closed doors. I need her treatment

JerkOffToCelebs

Rest of the dress as requested (assuming that is what they meant lol)

WtSSTaDaMiT

Natalie Portman dressed as a schoolgirl always makes me hard. I fantasize about her riding me and introducing my virgin cock to the pleasures of her pussy.

JerkOffToCelebs, celebJObuds

GF dressed as Harley Quinn (18f)

NudeCosplay

I will never tire of college girls dressing as Lara Croft

jobuds

Beads or a bold necklace can complement the exposed breast when wearing a one boob dress, as this lady demonstrates perfectly

AltBoobWorld

Real Life : a two-part open front dress, as seen here, can be a work of art to be studied for many hours

AltBoobWorld

This Teacher Looks Better Dressed as the School Girl!

u_xc1997x

So jealous of all the lucky guys who get to fuck Margot Robbie, particularly when she's dressed as Harley Quinn

JerkOffToCelebs

Brie dressed as Britney is so fucking hot

WorshipBrieLarson

If somebody would've told me a while ago that: "Soon you will be dressing as a girl, and enjoy posing for strangers in the Internet while wearing lingerie and a corset.." I wouldn't have believed that.. But here I am now….

Sissies

Mommy Emilia dressed as Daenerys watching me... Can't stop blushing...

CelebrityMommy, celebJObuds, JerkOffToCelebs

“Social Distancing” means I don’t have to get dressed as much, right?

GoneWildPlus

Lancer Artoria dressed as MHXX (NDGD) [Fate/Grand Order]

ecchi, rule34, hentai, u_HornyAsFrick

Young stars in the shadow of their older relatives: Taissa Farmiga, Emma Roberts, Maya Hawke (blowjob while dressed as her relative's best role, creampie missionary while her relative watches, doggystyle anal while watching her relative's sex scene)

CelebAssPussyMouth

r/jerkofftocelebs is having an orgy - who's your plus one, and what would you do? (I'd bring Melissa Benoist dressed as Supergirl).

JerkOffToCelebs

Busty goddess Dylan Ryder dressed as Catwoman.

PornIsCheating, pornjobuds

Do you like it when I dress as a school girl meowster~

catboys

Your step-dad caught you smoking and dressed as a sissy- you're going to be in so much trouble...

u_xxxSissyCaps, sissycaptions

Special request from a very polite man!! A little bit of anal play whilst dressed as a nun hope you enjoy

Nudes

Sometimes, I pretend I'm younger, dress as a schoolgirl, and have fun with myself ?

momsgonewild, Slut

The proper way to wear a dress as demonstrated by me ;)

boobs

My male Math teacher let me stay after school in his office to improve my grade with extra credit. It wasn't what I expected. I had to dress as a schoolgirl and give him a blowjob

EffeminacyAndFaggotry

Unidentified model dressed as nurse

PornMuseum

I wish Angela would dress as Velma again (and do The Walk™)

AngelaWhite

5'0 and 80lbs English girl here, dressed as Earth-Chan Girl and showing off my tiny tight pussy

Nudes, NSFWverifiedamateurs, Nsfw_Amateurs, GodPussy, funsized, asshole, adorableporn, GonewildGBUK, GonewildEU, youngporn, xsmallgirls, pussy, PetiteGirls, petite

The classic "o-dress", as seen in paintings from centuries ago, is still seen today - it's a fashion that's stood the test of time

AltBoobWorld