Sissy Jessica Cailin
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sissyjessica37.bsky.social
Sissy Jessica Cailin
@sissyjessica37.bsky.social
A useless, cock-hungry sissy slut, dripping in shame and desperate to be exposed, degraded, and treated like the filthy whore I am
Pinned
It wasn’t just big.
It was him.
And now my hole knows the difference between a man… and a bull.
I moaned. I leaked. I thanked him.

#BBCOnly #SissyForBBC #UsedHole #BetaCuck #ChastitySissy #Feminized #SissySlut #ButtSlut #BullOwned #FaggotTraining #GapingWhore
Reposted by Sissy Jessica Cailin
When daddy orders you to wear your sissy diapers on your run! 😳

📌 From: @boipadded on Tumblr

#diapers #diaper #DaddyDom #abdl #abdlcommunity #abdlphoto
November 15, 2025 at 11:33 AM
Reposted by Sissy Jessica Cailin
My new “Husband,” doesn’t want me trying to escape when I run off to the restroom, so no toilet for me. He said that a “Bridal Diaper,” isn’t even that uncommon, but is it usually this pink?
#ABDL #Diapergirls #Sissy #BDSM #Genderplay
December 1, 2025 at 6:17 AM
Reposted by Sissy Jessica Cailin
December 4, 2025 at 12:50 PM
Reposted by Sissy Jessica Cailin
Happy girly Friday~! Here’s my submission for big diaper friday!
#abdl #sissy #diaper #diaperboy #diaperfriday #BDF
December 5, 2025 at 8:01 PM
Reposted by Sissy Jessica Cailin
[COMM] Fallout: New Pampers
for "T"

Do you like it? Commissions are open!
Feel free to send me a message or email me
linktr.ee/trapdiaper

#trapdiaper #abdl #diaper #diapergirl #adultbaby #diaperlover #abdlart #オムツ #abdldiaper #diaperfetish #sissy #NSFW #messydiaper
December 5, 2025 at 10:09 PM
December 6, 2025 at 5:14 AM
Reposted by Sissy Jessica Cailin
Applying lipstick (or - as in the pic in the middle - getting it done) is one of the most erotic moves a woman can do in public... don't you agree?! 🫦💄
December 5, 2025 at 5:29 AM
December 4, 2025 at 6:27 PM
Reposted by Sissy Jessica Cailin
Have a fabulous evening everyone 💘💋
December 1, 2025 at 6:52 PM
Reposted by Sissy Jessica Cailin
#SissyClitty 🥰🫣
Hope you're all having a fabulous day 😘❤️❤️❤️💋
June 14, 2025 at 12:37 PM
Reposted by Sissy Jessica Cailin
Honest question. I have more receipts but I don't want to post them if you bunnies and hunnies aren't interested.
Receipts. Of course, nothing beats the first time squirting when you're pussyfree, right, @keybarrett.bsky.social?

#blacked #nsfw #qos #bbcaddict #noYtboid #bbc #satnotowhitrboid #handpusdy #pussyfree #pussyAnxiety
December 3, 2025 at 6:25 PM
Reposted by Sissy Jessica Cailin
I do too! Her shock at his load, her beautiful, encouraging voice, her perfect flat cage!

Everybody involved is happy she is being her authentic self, especially her!
December 3, 2025 at 8:07 PM
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I've been under the weather lately and I haven't had great mobility until the past four days. Now that I'm ok, it's time to raise hell again...
September 28, 2025 at 11:13 PM
Reposted by Sissy Jessica Cailin
One of my favorite people in the world, make sure you follow a d support her.
the world outside may be burning, but I'm damn near bedridden today from experiencing frankly staggering amounts of pussy last night so within these walls, (and those walls) good things are possible 😌

VIDEOS COMING SOON HERE!
💒 NikolaOphan.church 💒
November 23, 2025 at 8:44 AM
December 3, 2025 at 6:07 PM
December 2, 2025 at 8:22 PM
November 10, 2025 at 4:00 PM
It wasn’t just big.
It was him.
And now my hole knows the difference between a man… and a bull.
I moaned. I leaked. I thanked him.

#BBCOnly #SissyForBBC #UsedHole #BetaCuck #ChastitySissy #Feminized #SissySlut #ButtSlut #BullOwned #FaggotTraining #GapingWhore
July 6, 2025 at 10:52 PM
Reposted by Sissy Jessica Cailin
My first actual post. Hi there.
November 29, 2023 at 7:20 PM
She is lucky too. Mmmm
It's time to remind you about me isn't it?
June 24, 2025 at 2:04 PM
Lucky girl. Wish I was in her place
If you're seeing this then you're a real one.
June 24, 2025 at 2:03 PM
Reposted by Sissy Jessica Cailin
Suck a dick. No, seriously,suck a dick.
August 9, 2024 at 12:33 AM
Reposted by Sissy Jessica Cailin
Like seriously, what's better than black daddy dick ??
August 11, 2024 at 6:33 AM