Jizz

Straitjacket and Chastity

hentaibondage, hentaichastity

2 futa on 1 boy :) (x-post r/futanari) [wokada]

FutanariPegging, hentaichastity

Locked in, and hanging out.

hentaibondage, hentaichastity

Pink haired cat eater. (31/?)

hentaibondage, hentaichastity

(Not) Breakin' the chains of love

hentaibondage, hentaichastity

A few of my favorites... (543 of ???)

hentaibondage, hentaichastity

Chained in Chastity

BDSM_Artwork, hentaichastity

Sissy boy doing what sissies do best (causticcrayon)

traphentai, DeliciousTraps, hentaichastity

Pink and Purple

traphentai, hentaichastity

Princissy

SissyArtwork, hentaichastity, uAnimeGirlIrl

Safely Displayed

BDSM_Artwork, rule34bondage, hentaichastity, StuckHentai

Caffeine training

HookedUpHentai, hentaibondage, hentaichastity

Zelda Pegging Link by void nosferatu

traphentai, DeliciousTraps, PeggingArt, TheLostWoods, sissyanaladdicktion, Voidnosferatu, hentaichastity, u_purelytraphentai

Flirting

BDSM_Artwork, hentaichastity, uAnimeGirlIrl

Brutal anal pounding

HardcoreHentaiBondage, hentaichastity, HentaiAnal

Race

PredicamentHentai, hentaichastity, HentaiFunAndGames, NSFWTiedTogether

Sissy Maid Bukkake (PoisonCupid)

traphentai, DeliciousTraps, hentaichastity

Such A Pretty Boy. ?

DeliciousTraps, traphentai, hentaichastity

Everyone needs to know that she's owned

HentaiHumiliation, hentaichastity

Chelle's Lipstick

BDSM_Artwork, hentaichastity, uAnimeGirlIrl

Chelle's Dream #2 (Artist: Anasheya)

futanari, FutanariPegging, hentaichastity, u_Perusing-your-wears, ButtsVsBoobs

Demon GF takes you out [feminization]

hentaicaptions, hentaichastity

All locked up (combos-n-doodles)

traphentai, DeliciousTraps, hentaichastity

Pic of the day for January 09, 2019

hentaibondage, hentaichastity

Modern Marriage (OC)

DeliciousTraps, hentaichastity, traphentai, u_elizabethsissybottom, SissyHentai, femboyfemdom

Mistakes were made

HardcoreHentaiBondage, hentaichastity

Discipline [Chastity] [Orgasm Denial] [Punishment] [Spanking] [Paddling] [Schoolgirl] [Teacher] [Feminization] [Humiliation] [Femdom] [Bent over desk]

hentaicaptions, hentaichastity, TransgirlHentai

Bondage anal fucking

hentaibondage, hentaichastity, u_TipsyTime_

Teased for her pleasure

HotorNotFemDom, hentaichastity

Using the only option left to him

HentaiHearts, hentaichastity, HentaiForcedOrgasms, HentaiPetboys, hentaibondage, AdorableBDSM, u_jchastity

Embarassed and denied [Chastity] [Orgasm Denial] [Femboy/Trans Girl/Trap/Sissy/Insert Label Here] [Blushing] [Teasing] [Humiliation] [SPH] [Pink] [Latex]

hentaicaptions, hentaichastity, keyholdercaptions, positive_feminization, u_SissyJackie93, SissyHentaiCaptions, traphentai

Chastity control

hentaifemdom, hentaichastity

Good girl [Anal]

AnimeHighHeels, HentaiPetgirls, u_throwawayaccount4927, IWantToBeHerHentai, hentaichastity

QoS Sissy Cuckold Commission collab [OC]

netorare, hentaichastity, spicytuna, u_purelytraphentai, u_A-Great-Disguise

Chaste

AbandonmentHentai, hentaichastity

Link and Zelda

traphentai, hentaichastity

Feminized, chaste, and shared around the internet

HentaiBullying, hentaifemdom, hentaichastity

Reina Morimoto facesitting

BDSM_Artwork, thick_hentai, hentaichastity, husbandwifegoals

Facesitting - Chastity version

Skyldfri, hentaichastity, hentaifemdom

Bitchsuit-chan (Original) (りびむら) [Original]

hentaibondage, HardcoreHentaiBondage, HelplessHentai, hentaichastity, HentaiPetgirls, PetgirlHentai

Gamer Girl

Skyldfri, hentaifemdom, hentaichastity, u_purelytraphentai

sissy a la carte

traphentai, hentaichastity

"It's only some sissy hypno, it can't effect me THAT much" oh how wrong you were...

StraightToSissy, hentaichastity, Hentai_Interracial

Chastity Choice Caption! Choose your Keyholder v2! [Hentai] [Chastity] [Choice]

chastitychoice, hentaichastity, u_A-Great-Disguise

Chastity Choice Caption! Choose your Keyholder v3! [Hentai] [Chastity] [Choice]

chastitychoice, hentaichastity, u_jchastity, u_A-Great-Disguise

Chastity Choice Caption! Choose your Keyholder v4! [Hentai] [Chastity] [Choice]

chastitychoice, hentaichastity, u_A-Great-Disguise

Draw me like one of your Chastity Sluts (thanks to u/LongJohnSilver96 for the illustration!)

LatexModelDoll, hentaichastity

Me and Mahkara spending some romantic quality time toghether :3

Skyldfri, hentaichastity, hentaifemdom, gentlefemdom

Astolfo in Chastity Presenting Butt (TazzyMcFrazzy) [Fate/Grand Order]

hentai, hentaichastity

Sissy Nigh School

SissyHentai, BlackedArt, GayHentaiInterracial, Hentai_Interracial, chastity, NSFWart, Sissies, FemBoys, hentaichastity, sissyanaladdicktion, u_purelytraphentai

Nice and padded :)

hentaistraitjackets, hentaibondage, hentaichastity

Chastity-jacket? Someone must've been horny...

hentaistraitjackets, hentaibondage, hentaichastity, starstruckenf, AnimePossession

It's so big...

netorare, PenisAwe, hentaichastity

In a jacket and chastity belt.

hentaistraitjackets, hentaibondage, hentaichastity

Doktorsour drew me

LatexModelDoll, hentaichastity