| Gallery Name |
Images |
Quality |
Added |
Sissy Slut Margo
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9 |
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2023-07-15 |
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sissy boytoy #9
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87 |
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2023-07-15 |
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sissy boytoy #8
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97 |
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2023-07-15 |
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sissy boytoy #7
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99 |
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2023-07-15 |
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Sissy muslimah
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21 |
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2023-07-15 |
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Stature Of A Sissy 2 - SISSY COMIC
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10 |
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2023-07-15 |
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Stature Of A Sissy - SISSY COMIC
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12 |
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2023-07-15 |
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sissySky
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3 |
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2023-07-15 |
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SISSIED Pic Captions 8 - Sissy Captions
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100 |
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2023-07-14 |
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Slutty sissy styles my wife should force me to wear in public
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20 |
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2023-07-14 |
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Sissy Summer Captions
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16 |
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2023-07-14 |
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Vintage Buestenhalter fuer eine Sissy
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26 |
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2023-07-14 |
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Gute Buestenhalter fur brave Sissys
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Klassische Miederbuestenhalter fuer Sissys
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4 |
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2023-07-14 |
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Eine brave Sissy traegt auch die "richtigen" Buestenhalter
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SMOKING GIRLS SISSY ADVICE
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21 |
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2023-07-14 |
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smoking women who love sissys.
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SOLO SISSY CAPTIONS
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33 |
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2023-07-14 |
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SISSY CONFESSIONS
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But Grandpappy, I Don't Want To Be Your Sissy Bitch!
|
24 |
|
2023-07-14 |
|
Grandpa promised he wouldn’t tell anyone about how he made me dress up like a little girl and suck his… For more perverted fun like this check out my sissy humiliation e-books at www.lulu.com/spotlight/candy_runt
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Make Me Beg to Suck Your Cock Like Only a Sissy Bitch Can!
|
24 |
|
2023-07-14 |
|
Cum celebrate the world of forced feminization and public sissy humiliation with me and my full-length e-books! Available exclusively online at www.lulu.com/spotlight/candy_runt
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Ashley bieber slut expose got her bother Kik sissyboy586
|
45 |
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2023-07-14 |
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Ashley bieber slut kik her brother expose her kik sissyboy586
|
48 |
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2023-07-14 |
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Sissy Wrapped
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4 |
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2023-07-14 |
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unwrap me
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A collection of Tasty Trashy Trannies sucking on my cock
|
53 |
|
2023-07-14 |
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Different sissy sluts gobbling on my engorged cock.nEnjoy fapping to them
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alyssaavalon captioned by request want to be spread around
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7 |
|
2023-07-14 |
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alyssaavalon a sissy to use for your pleasure
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Early Sissy Me
|
14 |
|
2023-07-14 |
|
My first go at dressing like a sissy. Hadn’t considered my clitty and body needed a good shaving yet! Still finding more old pics to post up, so let me know if you would like to see more!
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exposed_for_you slave exposure photoshoot shaved sissy fun
|
30 |
|
2023-07-14 |
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exposed_for_you shaved and exposed in hot poses, submissive, slave waiting for cocks or strapons. Camming can be difficult to time and time zones get in the way but most instructions can be followed and your wishes satisfied through pictures, just ask...
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Happy Fishnet Friday
|
4 |
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2023-07-14 |
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Sissy, Chastity, Cock
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Wonderful Teen Sissy
|
8 |
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2023-07-14 |
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femdom sissy chastity vol 118
|
49 |
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2023-07-14 |
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Sissy Cheerleader Mouth Spreader
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13 |
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2023-07-13 |
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Mrs. Crenshaw trains a laundry sissy
|
1 |
|
2023-07-13 |
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Mrs Crenshaw uses sissification to make her laundry boy more compliant. Credit to the brilliant fetish artist Hopkings, picture 281, for inspiring this caption.
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Slutty Sissy Cheerleader
|
10 |
|
2023-07-13 |
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Sissy Slut University: Fall Semester
|
26 |
|
2023-07-13 |
|
Part 1 of a three part story telling a story about Sissy Slut University inspired by many other great captioners!! Check out waggerjob, marfisa, and feminyze_captions if you like this story ;)
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Don't Make Me Suck That, I'm A Man - Sissy Captions
|
24 |
|
2023-07-13 |
|
Please visit my online bookstore for my full-length (over 100 pages each) forced feminization and sissy humiliation stories. Visit www.lulu.com/spotlight/candy_runt
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My Sissy Caption Gifs - 2
|
50 |
|
2023-07-13 |
|
I loved the feedback everyone gave. Here's another set of captions for sissies to goon to. Let me know any feedback or kinks to add, happy fapping sluts.
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SissyGirlBella
|
16 |
|
2023-07-13 |
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Femboy/Sissy Hentai Captions 1
|
8 |
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2023-07-13 |
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Grindr Sissy Gif Captions 3
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17 |
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2023-07-13 |
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Sissyfication
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61 |
|
2023-07-13 |
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Sissy Slut Mayhem 1
|
20 |
|
2023-07-13 |
|
First of a series I'm making getting AI to create some sexy sissy sluts. Pink pink pink. ;-)
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SUBMISSIVE SISSY CUCKOLD 20
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50 |
|
2023-07-13 |
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(#4) gay/sissy mind-control captions
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6 |
|
2023-07-13 |
|
I do not own any of the images. I do not condone violence, acts depicted are purely fantasyn n(DM me for commissions.)
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My Sissy Caption Gifs - 1
|
24 |
|
2023-07-12 |
|
I've been thinking about making captions for awhile; here's my first attempt. They should be perfect for sissy sluts gooning to big fat cocks. Let me know what you think, love to get feedback.
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Twisted Sissy Captions - Vol 2
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12 |
|
2023-07-12 |
|
My original Sissy caps. Tell me if you want more ;)
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Sissy Cuckold Stories 16
|
312 |
|
2023-07-12 |
|
The degradation, humiliation and teasing of the feminized sissy cuckold by wives and other significant women in it's life.
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Shiri--Pale, Cute, Naked, Vulnerable Redhead Sissy Gurl!
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12 |
|
2023-07-12 |
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My favorite sissy captions
|
22 |
|
2023-07-12 |
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susan_cd on Imagefap
|
24 |
|
2023-07-12 |
|
This is what happens to sissy sluts that tease me and beg NOT to be exposed. One too many face pics will get my attention quickly.
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|
Sissy Asian Captions ~🎔LeanneLust🎔~ 3
|
10 |
|
2023-07-12 |
|
Found some of my old captions, really glad to be able to share them again. Sissify all asians
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Sissie-cuck Affirmations 3
|
55 |
|
2023-07-12 |
|
Affirmations for facing the challenges of being a fully devoted sissy-cuckold.
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Yummy Bras 14
|
50 |
|
2023-07-12 |
|
Yummy bra images, with gentle sissy-cuck messaging. Nothing persuades a submissive guy to embrace femininity and chastity like an alpha female wearing a delicious bra.
|
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Sissy cheerleader
|
8 |
|
2023-07-12 |
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Captions Vol 2.22 (Sissy, Cuckold, femdom, Bisexual)
|
16 |
|
2023-07-12 |
|
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feminization art, sissy, femboi,cd 7
|
48 |
|
2023-07-11 |
|
I like to see artistic expression, and the representation of desires and fantasies. I continue my collection for those who appreciate C.D. sissy chastity. I wish you a nice day
|
|
|
|
How I desperately need to be used...RIGHT NOW! (gifs) 5
|
19 |
|
2023-07-11 |
|
Another wish series where I imagine myself being used like the sissy slut I really am.nPlease feel free to comment on how you would use my sissy holes for your own pleasure or bring some friends. ;-)
|
|
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|
sissy captions
|
30 |
|
2023-07-11 |
|
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Fuck Responsibly, ALWAYS Wear a Sissy!
|
22 |
|
2023-07-11 |
|
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Sissy Caption Gifs - 3 (Suck Cock Edition)
|
103 |
|
2023-07-11 |
|
If you're here, you're no longer just "curious". You're falling down the sissy slut rabbit hole and you'll be a full-fledged slutty little sissy in no time. Get comfy sissy. Stare at your screen sissy. Listen to the porn, and picture yourself in it....
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Suson Fetish 21
|
240 |
|
2023-07-11 |
|
suson sissy nappy diaper abdl fetish pee plastic plasticpanty panty submissive ageplay regression pvc leather latex rubber piss adultbaby ab smooth slippery satin maid
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|
Sissy Lana
|
231 |
|
2023-07-11 |
|
SnowbunnyNative from Saskatoon, Saskatchewan with PumpkinButt / HoneyButt. Follow her on Twitter Sissycaged13
|
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|
|
Girly and sissy stuff I like
|
970 |
|
2023-07-11 |
|
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|
|
Sissy/Trans Brothers 'n Sisters Captions #1
|
22 |
|
2023-07-11 |
|
Sîblinglove is one of the hottest things, right? And it gets turned up to 11 when there are sissies and feminization involved. Leave many yummy comments and let me know if I should do more!
|
|
|
|
Red Sissy Locked
|
4 |
|
2023-07-11 |
|
No Fun Zone
|
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|
Sissy Stuff 17
|
101 |
|
2023-07-10 |
|
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|
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|
Epically ruined sissy comic
|
3 |
|
2023-07-10 |
|
A brief but oh so sexy comic from @DeprivedArt on twitter. The beautiful realisation that her desire to break her clitty has come to fruition makes me leak!
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|
Sissy Stuff 16
|
134 |
|
2023-07-10 |
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|
Sissy Claire, my newest Exposure slut - kik: superbored0392 -
|
26 |
|
2023-07-10 |
|
Claire is 27 year old Sissy slut from the USA. Her discord: sissygirlclaire
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Sissy pasiva
|
3 |
|
2023-07-10 |
|
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SISSY Brothers- GIF'S CAPTIONS - Requested
|
20 |
|
2023-07-10 |
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|
Ruined Sissies Magazine
|
10 |
|
2023-07-10 |
|
Oh look it's me Steve Mack aka Sissy Maria Clayton! In issue 05 of Ruined Sissies Magazine. Now being spunked over by men all over the world, and god i love it
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|
|
Magic Transformation - Fun For You
|
11 |
|
2023-07-10 |
|
Magical transformation story where a cross-dressing guy gets punished by his witchy girlfriend...with a twist! bra, witch, magic, girlfriend, roommate, magic, transformation, curse, coworkers, shower, pee, pov, downblouse, cleavage, skirt, nylons,...
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|
|
|
Other Gender Transformations - 12
|
21 |
|
2023-07-10 |
|
Various gender transformation captions which don't fit into my other categories. Includes: male to female, body swap, sex change, mtf, teen, selfie, bound, asian, chinese, japanese, body hopper, head swap, bra, panties, nylons, high heels, witch, milf,...
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Sissy Series Leftovers 009(retry)
|
16 |
|
2023-07-10 |
|
More new captions from existing series, where there are not enough for a new full gallery in that series.
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Sissy Captions 31
|
16 |
|
2023-07-10 |
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Ballet Boots Sissy needs Daddys Cock
|
10 |
|
2023-07-10 |
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Sissy waiting for Daddy
|
9 |
|
2023-07-10 |
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July Sissy Gurls PT 3
|
31 |
|
2023-07-10 |
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A GALLERY OF A FRIEND, SISSYGEORGINA69 FOR YOUR SHARING.
|
7 |
|
2023-07-10 |
|
I’m asking everyone to share this sissy’s pictures on your pages. Thank you.
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|
Sissy Heidi
|
18 |
|
2023-07-10 |
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Sissy Woods
|
4 |
|
2023-07-10 |
|
Let’s Play in the Woods
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Cute submissive sissy
|
4 |
|
2023-07-10 |
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TeasAndDenial Femdom Captions 50 (Sissy/Cuckold/Chastity)
|
12 |
|
2023-07-09 |
|
Gallery 50 of my original captions for all you betas x
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Diana sissy clit
|
23 |
|
2023-07-09 |
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Collage faggots and sissy
|
40 |
|
2023-07-09 |
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Big dick/Shemale/strapon/sissy/cuck/panty fetish/sex dolls 15
|
222 |
|
2023-07-09 |
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Nadias sissy Clit (she is ready to be locked)
|
28 |
|
2023-07-09 |
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Captions of Jade Storm (Formerly Sissy Nina Jade)
|
15 |
|
2023-07-09 |
|
Captions of Jade Storm from Reddit. Jade previous was know as Sissy Nina Jade on Tumblr. All captions by request. Message me if you are interested in being captioned.
|
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|
Classic Sissy Captions
|
79 |
|
2023-07-09 |
|
Classic Captions from Tumblr and Reddit from 2011 to roughly 2022. In most cases, the models are tagged in the image. All captions by request. Message me if you are interested in being captioned.
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|
|
Michelle on Imagefap__michelle31
|
36 |
|
2023-07-09 |
|
Another sissy slut with the name Michelle. This is one of the galleries that was deleted when I closed my account a few months ago. I added a few pics thanks to aliciacat
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Layla sissy slut
|
4 |
|
2023-07-09 |
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MichelleBlueCD on Imagefap
|
8 |
|
2023-07-09 |
|
This was an impulse gallery post. I felt like I was being dared by this slutty little sissy faggot! See what I did to you Michelle??
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Sissy Spence
|
16 |
|
2023-07-09 |
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Melasissys Goonfuel (non-nude) captions
|
41 |
|
2023-07-09 |
|
Dirty comments are welcome
|
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Exposing sissy roxanne
|
24 |
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2023-07-09 |
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Sissy roxanne bimbo fakes
|
9 |
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2023-07-09 |
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Me, slut sissy for exposure
|
25 |
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2023-07-08 |
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Sissy Fucked
|
10 |
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2023-07-08 |
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Sissy Sammy can´t get enough Exposure - kik: SissySammy222
|
25 |
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2023-07-08 |
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Sissy Fag Trisha House
|
54 |
|
2023-07-08 |
|
Sissy fag Trisha House crossdresser. Loves sucking cock.n
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Sissy bunny
|
5 |
|
2023-07-08 |
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Captions: Sissy, Cuckold, Ballbusting, Domination2
|
108 |
|
2023-07-08 |
|
Some of these I made, some of them I got from you guys, some of them I saw on-line and wanted to change something. I hope you enjoy them, they are in this file it is because I did!
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Sissy tribute
|
12 |
|
2023-07-08 |
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Sissy Candi Doll (Chubby or Fat Tgirl)
|
27 |
|
2023-07-08 |
|
Found on reddit: Sissycandidoll
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Sissy Ashley
|
44 |
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2023-07-08 |
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sissy boytoy #6
|
99 |
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2023-07-08 |
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sissy boytoy #5
|
99 |
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2023-07-08 |
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Sissy girls and their masters 2.
|
47 |
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2023-07-08 |
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Sissy Bitch Kendall Mckenna Exposed
|
20 |
|
2023-07-08 |
|
Download my pics: files.fm/u/7k567kv6sj
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sissy feelings
|
1 |
|
2023-07-08 |
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SissyGirlBella
|
16 |
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2023-07-08 |
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Slut Sissy Fuckhole Jay Gapes
|
58 |
|
2023-07-08 |
|
Cam Guy Jay Gape fucks himself and fucks friends and friends fuck him..
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SISSY CAPTIONS 77: SWORDS AND SORCERY (HENTAI) III
|
10 |
|
2023-07-08 |
|
hihi~! we're going back to swords and sorcery this week, with a bunch of little sissy elves and beastkin and human loooosers who are just way too easy to subdue and sissify!! this week's theme was commissioned by a lovely anon over on twitter, so many...
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A day in the life of a Sissy Whore (3): Blowjobs!
|
24 |
|
2023-07-08 |
|
Hello once again! I'm Gabrielle, a sissy whore and today I'll tell you how to get shy guys to let you into their car and how you should treat them to get them to cum in your mouth, keeping in mind our motto "Time is money". Come with me! (you can see...
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Sissy Bitch Bondage 5
|
16 |
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2023-07-08 |
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Sissy Bethy
|
5 |
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2023-07-08 |
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Sissy Alex Marceau exposed - kik: alexandra.kink -
|
26 |
|
2023-07-07 |
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Sissy Victoria Parker needs lots of Exposure - kik: cdvpark3001-
|
29 |
|
2023-07-07 |
|
Victoria is 36 years old and lives in Victoria/Texas.
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Sissy Captions 3
|
57 |
|
2023-07-07 |
|
Sissy captions
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After party of sissy in chastity (sub517)
|
47 |
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2023-07-07 |
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trad wife sissy shit
|
63 |
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2023-07-07 |
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Nina1971 captioned showing what a sissy slut she is
|
6 |
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2023-07-07 |
|
nNina1971 a feminine submissive sissy for you all to enjoy
|
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Sissy Caption Gifs 1
|
5 |
|
2023-07-07 |
|
Some of my Sissy Caption Gifs that I have made. Includes Latex, Gloves, Pink, Chastity, Thigh High Boots, Corset, Stockings, Panties, Butt Plug, Ass Play, Condom Play, Hypnosis, Dildo, Cum Facial and Sissygasm.
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Good Gurls Rehab - 12
|
23 |
|
2023-07-07 |
|
Good Gurls Rehab - Using Swap Clinic technology, GG Rehab swaps troubled, disruptive boys into productive young women. Some are taken to the clinic by their parents. Others are forced to attend after getting in trouble with the law. A few even...
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Jessica sissy slut exposed
|
12 |
|
2023-07-07 |
|
Sissy slut Jessica, always craving humiliation and degradation is now an exposed sissy whore. dressed, locked in chastity, and ass filled.
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Big dick/Shemale/strapon/sissy/cuck/panty fetish/sex dolls 14
|
222 |
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2023-07-07 |
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Sissies And Their Mistresses 2
|
143 |
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2023-07-07 |
|
Sissy Manor - Nottinghamshire 2019
|
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Sissies And Their Mistresses
|
67 |
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2023-07-07 |
|
Sissy Manor photoshoot, August 2020
|
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My Twisted Sissy Fantasies 68
|
18 |
|
2023-07-07 |
|
Enjoy my 68th caption set! Some of my captions contain dark sexual themes that scratch my fantasies and I in no way advocate or support real world violence or aim to offend anyone.
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July Sissy Gurls PT 2
|
30 |
|
2023-07-07 |
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Olivia Holt sissy captions
|
12 |
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2023-07-07 |
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Chantellesissy -sissy faggot for exposure, abuse and humiliation
|
10 |
|
2023-07-06 |
|
Im a sissy faggot tranny submissive who loves use, abuse, exposure, degradation, humiliation, ridicule, and anything bizarre to make me feel like the limp clitty sissy girly pansy fairy that I am
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Sweet Sissy Baby
|
25 |
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2023-07-06 |
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Sorry I've been gone so long. Hope you all enjoy me being a cute sissy baby! Please share my pics, use them in captions i want everyone to see what a cute sissy diaper doll I am.
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Sissy Micki collages
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12 |
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2023-07-06 |
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A few of my favorite images of my sissy self. Feel free to download/repost--I love being exposed!
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Kimnylons captioned show what a slut she is as requested
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6 |
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2023-07-06 |
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Kimnylons such a slutty sissy for you all to enjoy and toss off with.
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Psychologists who treat pathetic losers 12
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24 |
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2023-07-06 |
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They say admitting it is the first step to recovery, only there's no recovery for you. Dominant female psychologists don't suffer pathetic, sissy, bitches. Dominant psychologists prefer not to waste their valuable time on beta wimps like you. They are...
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there is a place for you, sissy
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14 |
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2023-07-06 |
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Only you are missing, dear sissy, come, show your ass, the party is about to begin
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Valli on Imagefap
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20 |
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2023-07-06 |
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You would never know this little sissy slut was once a boy. My cock aches to be inside of her slutty little holes.
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sissy Titia trying to be a good pet girl
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36 |
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2023-07-06 |
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MISTRESSES AND SISSY SLAVES MAIDS 36
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100 |
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2023-07-06 |
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femdom sissy chastity vol 117
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50 |
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2023-07-06 |
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Sissy Captions 7
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211 |
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2023-07-06 |
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Secret Sissy Seeks Sexual Domination and Humiliation - Captions
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24 |
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2023-07-05 |
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Timid men bullied and blackmailed into sexually servicing Alpha males in the most humiliating manner imaginable. If this theme ‘floats your boat,’ then please check out my full length sissy humiliation stories at...
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Sissy Stuff 15
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60 |
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2023-07-05 |
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Sissy Stuff 14
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74 |
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2023-07-05 |
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Sissy and Feminization Captions 27: Feminized by Family 4
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20 |
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2023-07-05 |
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Beta bois are forcibly feminized into submissive sissies by sinister stepsisters, and demoted to docile darling daughters by sadistic stepmothers and merciless moms.
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Born to be Your Sissy Bitch - Captions
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24 |
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2023-07-05 |
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Slutty Jessy seeking attention - kik: subsluttyjesssy -
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25 |
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2023-07-05 |
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Sissy Jessy loves dirty comments and messages. She is public domain, so fell free to download and share her pics. This little slut loves to see her stuff on other pornsites or getting used for Sissy Hypno vids. Check out her gallery on erome, it has...
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Sissy Bianca's cuffed struggles
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10 |
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2023-07-05 |
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Bianca loves the feeling of being restrained by cold unyielding steel while encased in skin tight latex and PVC outfits, struggling for balance in high heels.
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What sissymaster2022 likes Sissies
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42 |
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2023-07-05 |
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Sissy Exposed by Master Black Knight
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7 |
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2023-07-05 |
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PoppyBimbo captioned showing what a lovely feminine sissy she is
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6 |
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2023-07-05 |
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PoppyBimbo A sissy for you all to enjoy and get off with.
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Sissy Bitch
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11 |
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2023-07-04 |
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