Videos

00:32

Goon collection - Videos

Pervgooncreeper 20.8K

01:21

Caption Incest Sissy stuff

santas_lap 61K

01:56

Bnwo

Pervgooncreeper 7.8K

00:18

sissy caption

Story_Writer 6.9K

01:00

Cuckold captions and some sissy pics

Sissy_Perv 9.2K

01:34

Goon mix 4

Pervgooncreeper 2.4K

00:08

Goon mix 3 - Aspects of findom

Pervgooncreeper 1.7K

00:32

Instagram vs twitter

CaptionStories 1.1K

00:20

Submission Caption

Pakistani 10K

02:46

Sissy Chink (claim)

ImThatGuy_ 3.2K

00:46

BNWO tattoos and captions 2

Pervgooncreeper 331

00:13

BNWO tattoos and captions 2

Pervgooncreeper 126

Galleries

Sissy Captions-From my Tumblr page 0 Videos • 56 Images

Sissy captions 0 Videos • 11 Images

Sissy captions 0 Videos • 10 Images

Sissy captions 0 Videos • 9 Images

sissy captions 0 Videos • 86 Images

Sissy captions 0 Videos • 10 Images

WTF?

Nothing Is Sacred Anymore

anonymous 767

Married Woman vs. Gang Bang

anonymous 589

The Absolute Worst of Pornhub VII

anonymous 1380

The Most Obnoxious Cameraman in Porno History

anonymous 720

Intellectual Fail

anonymous 1503

Girl Gets Publicly Jizzed On

anonymous 535

Sissy Captions

2,818 Uploads · 1,981 Members · 139 Forum Posts · 1,573,244 Visitors

Group for purpose of sharing sissy caption images including sissy, crossdress, transformation, bodyswap and bodysuit. Please just be respectful, were all here for the same reason.

Sissy Training

13,171 Uploads · 3,996 Members · 122 Forum Posts · 1,490,999 Visitors

A stockpile of sissy training videos and captions

Sissy Boy Fuck Toy

553 Uploads · 241 Members · 6 Forum Posts · 177,668 Visitors

Captioned SISSY,TRAN,FAG,SHEMALE and CROSS DRESSER Pix.

Pegging Captions

535 Uploads · 365 Members · 1 Forum Posts · 153,359 Visitors

Captions of Men being fucked by women with dildos. All Female pegging male captions are allowed, so Sissy fucked by woman, femdom, marriage role reversal, etc all at play.

Censored Porn For Sissies

321 Uploads · 39 Members · 2 Forum Posts · 77,938 Visitors

A place for sissies to "enjoy" pics and vids of sexy celebrities and porn stars etc. without actually seeing the naughty bits which should be reserved for REAL men! Only non-nude/clothed and/or edited and/or censored (ex:blurred, pixeled, bubbled, black bars,cropped, handbras) are permitted here. No exceptions! Sissy porn (ex:babecock) and pics with captions are encouraged too but not required. Have fun loooozers :)

Local sissy support

3,611 Uploads · 510 Members · 40 Forum Posts · 195,175 Visitors

A group for sissies, bimbos, and their admirers to post vids, pics and captions and maybe even get together in hopes of helping sissies please real men

Sissy__Time (:

845 Uploads · 109 Members · 0 Forum Posts · 19,493 Visitors

Sissy, shemale, gurl, boipussy, femdom, trap, transgender, tranny captions and best pics!!!!

Board Posts

-2

Anonymous

@confessions

04 Nov 2025 10:04PM

• 47 views • 0 attachments

[ − ] thread [ 2 replies ]

Hi, ladies and gentlemen, please comment whether you enjoy this confession or whether it repulses you.

Just got back from visiting my plug and he generously offered me 25% off if I stroked his cock and sucked his balls until he got off. I appreciated the offer so I did just that after we passed a glass cock back and forth and got ourselves spun the fuck out. Now I'm back home, blowing clouds, and stroking to sissy caption galleries here on motherless like a good little sissy slut.

reply favorite add to gallery permalink Share

Copy

Anonymous

@guys

15 Dec 2024 12:17AM

• 141 views • 1 attachment

[ − ] thread [ 0 replies ]

Sydney sissy caption slut
fucking Asian sissy bitch raw

reply favorite add to gallery permalink Share

Copy

Anonymous

@guys

15 Dec 2024 12:25AM

• 0 views • 1 attachment

[ − ] thread [ 0 replies ]

Sydney sissy caption slut

reply favorite add to gallery permalink Share

Copy

-1

Anonymous

@requests

05 Nov 2022 9:14PM

• 0 views • 0 attachments

[ − ] thread [ 0 replies ]

Does anyone have a collection of sissy captions (gifs, images or videos) that mentions something along the lines like "multiple loads" "for hours" etc?

reply favorite add to gallery permalink Share

Copy

eluna_84

View posts View profile

@requests

21 Feb 2023 9:27AM

• 275 views • 1 attachment

[ − ] thread [ 6 replies ]

I want to be in sissy, trainer etc caption, is there a chance ?

Woman inside, crossdressing, feminizing

reply favorite add to gallery permalink Share

Copy

Anonymous

@requests

15 Nov 2025 5:52AM

• 0 views • 1 attachment

[ − ] thread [ 0 replies ]

Caption this sissy

reply favorite add to gallery permalink Share

Copy

Anonymous

@guys

12 Dec 2024 10:07PM

• 0 views • 1 attachment

[ − ] thread [ 0 replies ]

Sissy will caption your foreskin cock pic

reply favorite add to gallery permalink Share

Copy

-1

cdnicole

View posts View profile

@motherless

06 Apr 2012 12:49PM

• 756 views • 0 attachments

[ − ] thread [ 2 replies ]

Hi, im new and I started a new group but need members to get it public, if you enjoy sissy captions then please join. http://mlps.pika777.eu.org/g/sissy_captions

reply favorite add to gallery permalink Share

Copy

Nude Vista Content

Intimate Lessons - Sissy Caption Story

12:11 13.7K

Soldier to Bitch Part 01 - Sissy Caption Story

06:59 18.4K

Sissy Anal Sex toy Training with Captions

09:30 8.7K

Sissy Caption Story - I Switched Bodies With My Stepmom

07:59 8.7K

Lana Rhoades In Stepdaddy And His Friends - Sissy Caption Story

07:24 6.6K

Bad Teacher Part 01 - Sissy Caption Story

10:39 10K

sissy captions porn results Showing 57 of 27,702

Videos

Images

Galleries

WTF?

Nothing Is Sacred Anymore

Married Woman vs. Gang Bang

The Absolute Worst of Pornhub VII

The Most Obnoxious Cameraman in Porno History

Intellectual Fail

Girl Gets Publicly Jizzed On

Groups

Sissy Captions

Sissy Training

Sissy Boy Fuck Toy

Pegging Captions

Censored Porn For Sissies

Local sissy support

Sissy__Time (:

Board Posts

Nude Vista Content

Intimate Lessons - Sissy Caption Story

Soldier to Bitch Part 01 - Sissy Caption Story

Sissy Anal Sex toy Training with Captions

Sissy Caption Story - I Switched Bodies With My Stepmom

Lana Rhoades In Stepdaddy And His Friends - Sissy Caption Story

Bad Teacher Part 01 - Sissy Caption Story