Jizz

First time in panties :)

Sissies

First time in this subreddit. Fappy Friday!

penis

First time in softies. PMs/Comments with requests always welcome.

softies

First time in this sub

mangonewild

First time in this sub. What do you want to see?

GoneWildCD

First time in here, showing a little more!

GoneWildCD

First time in this sub, hope y'all like it!

dicks

First time in a thong I promise I would post a picture :) NSFW

Sissies

First time in chastity :)

Sissies

First time in GW. You women are so beautiful!

BHMGoneWild, GoneWildPlus

First time in NYC. (NSFW)

pics

First time in this subreddit, what do you think?

Balls

First time in here ;)

gonewild

First time in this sub. You boys (and hopefully a few girls to ;) like what I got?

Precum

First time in r/sissies. Thoughts?

Sissies

First time in chastity and loving it....

GoneWildCD

First time in these

GoneWildCD

First time in this sub. Thoughts? Just hanging this morning

ratemycock

First time in this Sub

jacking

First time in this sub, any love for a hard chubby guy?

GaybrosGoneWild

First time in public - Chubby Sissy

Sissies

First time in long(ish) term chastity, friendlink inside!

chastity

First time in Panties. What do you think? PMs welcome :)

FemBoys

First time in panties, damn these feel sexy

Sissies, MenInPanties, DragonsFuckingDragons

First time in awhile, tell me how I did

Sissies

first time in this sub

ladybonersgw

First time in chastity.

chastity

First time in posting be nice to me

gonewild

First time in fishnets and heels. ;) What do you guys think?

GoneWildCD, Sissies, FemBoys

First time in thong. Do you like my cute butt?

GoneWildCD

First time in chastity. Do I need to size the ring down?

chastitytraining

First time in too long

FemBoys, Sissies

First time in this sub

PantyBoners

First time in panties and love it

GoneWildCD

First time in a dress what do you think

TrapsUK

First time in her ass

GWCouples, gonewildcouples, AnalGW

First time in a wig, feels so right

Sissies

First time in panties, think my clitty may like them x

Sissies

First time in a body stocking, what you think?? ?

sissypersonals, Sissies

First time in a garter belt.

Crossdressing_xxx

First Time in a Jock Plugged

jockstraps

First time in panties...

Sissies

First time in public, more to come?

holdthemoan, better_holdthemoan, sunnynudes

First time in 25 years showing my feet to the world and thinking about showing them more depending how much love they get.

feet, FootFetish, feetshowing, feetish, Feet_NSFW

First time in lingerie!

GoneMildCD

First time in a dress. I love it ?

GoneWildCD

First time in chastity! How long should I stay locked?

SissyChastity

First time in rubber last week [20M]

GayKink, maleshinyporn

First time in this sub

GaybrosGoneWild

First Time in this sub!

DickPics4Freedom

First time in lingerie. Would you hit it? AIC

sissydressing

First time in small cage, would love for someone to check pic

chastity

First time in lingerie

BarelyClothed, boudoir, clothedwomen, cuteasfuckbutclothed, InnocentlyNaughty, legs, LegsForDays, legsup, innocentturnssexual, lingerie, LingerieGW, LingeriePlus, lingeriewomen, pantyhose, socksgonewild, stocking_paradise, ThickThighs, Thighs, voluptuous, Amateur

First time in chastity

chastity

First time in fishnets what do we think ??

fishnets

First time in full outfit ?

Sissies, FemBoys, traps

first time in public with mini cage

MasculineMaleChastity, chastity

First time in a skirt...I'm a changed gurl.

trapsarentgay, sissypersonals, FemBoys

First time in fishnet ??

TGirl_Feet, Stupidsissyslutsclub, FemBoys, Sissy_humiliation, SexyShemales, TransGirlsNude, SissyHubbies, SissyInspiration, Sissy_hot, SissificationProject, sissyplace, sissydressing, CDgonewild, TransGoneWild, Sissies, Ladyboys, SissyFemdom, trapsarentgay, TrapsUK

First time in years I've sat on a dick... I think i took it like a champ ;)

BBWTrans