Jizz

One of the hottest black latex dresses out there

ShinyPorn

One person's skirt is another hiked up dress :D

GoneWildCD

One of my friends dressed up as Cinderella [NSFW]

pics

One thing I love about wearing a dress to work is the convenience of being able to take pics like this for you.

gonewildcurvy

One of the first set of shots i ever took x-dressing, let me know what you think!

GoneWildCD

One of my favorite things. Dressed to the nines, prim and proper. Secretly hoping somebody will see her for what she is, and use her like the slut she wants to be.

maledom

One More Quick Of Me Getting 'Dressed' (F)

gonewild

One of my fav dresses :) care to see the new lingerie hiding underneath?

GoneWildCD

One more tease before showing the goods ;) I just love this dress do you?

GoneWildCD

Dress shopping this afternoon and immediately thought o[f] GM when I tried this one on

GoneMild

One more (cross dressing) Christian 'Dog' on BRUUUCE Jenner

Sidehugs

Dress appropriately, it's gonna be a hot one! (F)

GoneMild

One more (F)or you ladies then I guess I'll get dressed.

gonewild

Dress up --pick one--

HARDchoicesNSFW

One more pic of me all dressed up

diaperpics

One of the many perks of working from home is the relaxed dress code policy...

tinydick

Dressed to impress. Which one would you take home?

Ifyouhadtopickone

One o(f) my tight dresses

tightdresses, burstingout

Dressed up, tied up and fucked ? [F] and one with [M]

NakedCurvySluts

One of my new dresses ? I LOVE it!!

FemBoys

one submissive act dare: Dress up in something really cute and submit the photo to r/Sissies/ ... so here it is!

Sissies

One thin dress

pokies

One of those smeared off lip stick, stained dress kind of nights..

traps, GoneWildCD

One post awAy from catgirl boogaloo 2, here's some pics of me in the "stolen" maid of honors dress, story below

traaNSFW

Dressed like a hotwife and ready to become one.

Cuckold, WouldYouFuckMyWife, NSFW_Tributes, 40plusGoneWild, gonewild30plus

Dress for the job you want, not the one you have! kik: sissy_bell

sissykik, sissymaid, Sissies

One short dress has to win

TrueFMK

One year ago- in a suit, with my hetero girlfriend. Same party next year- functioning as a girl myself, short dress, pantyhose, visible feet to attract alfa male

Sissies

One of my favorite "dresses" ;)

nsfwoutfits, Slut, lingerie, WhyEvenWearAnything

One of the many reasons to wear dresses at work :)

gonewild

One of my first pictures just getting started at dressing

GoneMildCD

One positive of running in Florida is dressing like this for a February race...

SexyTummies

One of the hottest dresses I’ve seen on her

AsianCuties

One sexy dress

myfavpicspostsandmore

One of my current waifus dressed up as my childhood waifu? YES PLEASE.

u_WolfieByNature

One of my favorites dressed up as a goth sissy, should i fall back down the rabbit hole?

Sissies

One of my favorite dresses to show off cleavage ?

mycleavage

One of my first times dressed up, is it time to start again?

Sissies

One minute was in my room, the next I was in an unfamiliar place with blonde locks covering my face. I kicked off the unfamiliar shoes around my suddenly dainty feet. I lifted up the strange dress I was apparently wearing, revealing the body of some older

bodyswap

One of my favorite gala dresses. I think it fits me quite well. ;)

cuteasfuckbutclothed

dressed up for this one! what do you think?

Ratemypussy, LabiaGW, crotchlesspanties, pussy, u_sweetsugarX

One of my fav cocktail dresses ? 36F

tightdresses, cuteasfuckbutclothed, boltedontits

dressed up like a bitch, make me cry like one?

gayasshole

Dressed up today and teased some guys.....made one cum on camera too ☺

sissydressing

One of the first dresses I ever bought, Still bulges in all the right places though xXx

tbulges

Dressing up during lockdown only leads to one thing ?

pussy