Jizz

Sissycaptionstories pics

Obligatory Christmas Caption

Obligatory Christmas Caption

genderotica, xxxcaptions, SissyCaptionStories

The Dress

The Dress

genderotica, xxxcaptions, SissyCaptionStories

Women's Studies [crossdressing]

Women's Studies [crossdressing]

xxxcaptions, SissyCaptionStories, Sissyperfection, MEFetishism, genderotica

Emerald Quest

Emerald Quest

genderotica, SissyCaptionStories

Lucid Dream

Lucid Dream

genderotica, SissyCaptionStories, xxxcaptions

Vengeful Ex

Vengeful Ex

genderotica, SissyCaptionStories, xxxcaptions

Going for a Tan (part 1)

Going for a Tan (part 1)

XChangePill, SissyCaptionStories, Sissyperfection, u_Shemale6911

Girlfriend Possession

Girlfriend Possession

genderotica, xxxcaptions, SissyCaptionStories

Reluctant Swapper

Reluctant Swapper

genderotica, xxxcaptions, SissyCaptionStories

Genderitis - Roommates

Genderitis - Roommates

genderotica, xxxcaptions, SissyCaptionStories

Beauty Potion [caption]

Beauty Potion [caption]

genderotica, xxxcaptions, SissyCaptionStories, opentgcaptions, XChangePill

Sissy's First Job

Sissy's First Job

sissycaptions, SissyCaptionStories, u_Koklick

Contemplating [caption]

Contemplating [caption]

genderotica, xxxcaptions, opentgcaptions, SissyCaptionStories, tgcaptions, XChangePill

Dominant new Dorm-mate.

Dominant new Dorm-mate.

sissycaptions, SissyCaptionStories, Sissyperfection, xxxcaptions

An (un)fortunate snapchat sissy

An (un)fortunate snapchat sissy

sissycaptions, SissyCaptionStories, Sissyperfection, xxxcaptions

Forced Feminization Caption - An Easy Decision

Forced Feminization Caption - An Easy Decision

genderotica, Sissyperfection, xxxcaptions, MEFetishism, SissyCaptionStories, tgtfbot

Warm Welcome [caption]

Warm Welcome [caption]

genderotica, opentgcaptions, SissyCaptionStories, tgcaptions, xxxcaptions, tgtfbot

Operation Chad [caption]

Operation Chad [caption]

genderotica, xxxcaptions, SissyCaptionStories, opentgcaptions, u_bucketbath11, Thingsthatgetmeoff, tgtfbot

Magic Sexy Santa Outfit [gif] [caption]

Magic Sexy Santa Outfit [gif] [caption]

genderotica, xxxcaptions, opentgcaptions, tgcaptions, SissyCaptionStories

Consuming Succubus

Consuming Succubus

genderotica, penectomy, transcubus, SissyCaptionStories, Feminization, gendertransformation, transformation

First Time

First Time

genderotica, Feminization, SissyCaptionStories, transformation, XChangePill, PussyEnvy, gendertransformation

I really thought I was going to keep it...

I really thought I was going to keep it...

genderotica, penectomy, PussyEnvy, SissyCaptionStories, Feminization, opentgcaptions, tgcaptions

Temple Supplicant

Temple Supplicant

genderotica, Feminization, SissyCaptionStories, PussyEnvy

Sweet Irony

Sweet Irony

genderotica, PussyEnvy, Feminization, SissyCaptionStories, opentgcaptions

I told myself I wouldn't post this but I wanted to share how amazing Daddy was at

I told myself I wouldn't post this but I wanted to share how amazing Daddy was at making me realise how much more fun being a woman is xXx

Feminization, SissyCaptionStories, sissycaptions, u_pitchardg, Sissyperfection

A Reluctant Camgirl

A Reluctant Camgirl

sissycaptions, Sissyperfection, SissyCaptionStories

You decided to stream with him from now on

You decided to stream with him from now on

sissycaptions, u_Night-Gift, SissyCaptionStories, u_Call-Me-Cutie, u_lilbadwolff11, u_naelsya, u_lil-cumslut

Sexy caption someone made of my image

Sexy caption someone made of my image

sissycaptions, Sissy_humiliation, FemBoys, XChangePill, Sissies, SissyCaptionStories

Let's get rid of that dry spell

Let's get rid of that dry spell

sissycaptions, SissyCaptionStories, Sissyperfection, r4rSydneyXXX

[EDIT]Cocks and Candy: Susan knew exposing her son Jamie to her *SlutCandy* was a

[EDIT]Cocks and Candy: Susan knew exposing her son Jamie to her *SlutCandy* was a great idea. Now her new daughter could quit college and help entertain her new daddy and friends............ (Long time fan here. This is my first edit. WDYT?)

johnpersonsthepit, SissyCaptionStories, futanari, u_purelytraphentai

You have become nothing more than their sissy hobby project.

You have become nothing more than their sissy hobby project.

Sissyperfection, genderotica, SissyCaptionStories

An unexpected surprise.

An unexpected surprise.

Sissyperfection, SissyCaptionStories, sissycaptions, u_pitchardg, u_A-Great-Disguise

The Dildo - Part 1 [caption] (parts 2-5 in comments)

The Dildo - Part 1 [caption] (parts 2-5 in comments)

genderotica, SissyCaptionStories, xxxcaptions

Bikini Trouble [caption]

Bikini Trouble [caption]

genderotica, SissyCaptionStories, u_SSAmberN, u_My_SecretConfessions, iwanttobeagirl

Keisha Gray

Keisha Gray

MagicNsfw, Hotdogging, SecureFolder, KeishaGrey, SissyCaptionStories, sissycaptions

2 choices what will you do ?

2 choices what will you do ?

NSFW_Caption, sissycaptions, SissyCaptionStories, xxxcaptions, SissyCaptionDump, SissyInspiration, u_lilbadwolff11, u_sissyboyjessica666

only 1 controller oh well

only 1 controller oh well

Cutesissycaptions, NSFW_Caption, sissycaptions, SissyCaptionStories, Sissyperfection, xxxcaptions, u_meanthickbald, u_JamieIsASlut, u_My_SecretConfessions, u_FUN1s, u_nimblybimbly436, u_Sissyjennycuckold

truth or dare gone too far

truth or dare gone too far

Cutesissycaptions, sissycaptions, SissyCaptionStories, xxxcaptions, u_FUN1s, Dutchsissies, u_makemeagurl4u

TGT Pledge Part 1 - 2

TGT Pledge Part 1 - 2

XChangePill, SissyCaptionStories

it's his now

it's his now

Cutesissycaptions, NSFW_Caption, sissycaptions, SissyCaptionStories, Sissyperfection, xxCaptions, xxxcaptions, BlowingClouds, u_gto1738

Guys will fuck anything if they're drunk and horny enough

Guys will fuck anything if they're drunk and horny enough

Cutesissycaptions, NSFW_Caption, sissycaptions, SissyCaptionStories, Sissyperfection, stillstraightcaptions, xxCaptions, xxxcaptions

just perfect

just perfect

Cutesissycaptions, NSFW_Caption, sissycaptions, SissyCaptionStories, Sissyperfection, stillstraightcaptions, xxCaptions, xxxcaptions, u_nimblybimbly436, u_SnooCakes8755

Keep stroking.

Keep stroking.

DEATHbyBBC, SissyCaptionStories, BNWOPropaganda