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01:21
Sissy Joyce Challenge
Sissy Joyce
158.4K views
15:33
14 Days Sissygasm Challenge handfree only Cumshots
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04:05
ABT250116 20cm Dildo Challenge
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02:46
Ride Dildo Challenges 2
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01:36
AB2503 Secretary 50cm long dildo challenge (Chinese and English subtitles)
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02:52
Edging Challenge
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01:16
Tranny Girl has fun with two small-dick losers! Nasty torture for their tiny cocks! Chastity SPH
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09:13
Warm and sticky cum inside nylon pantyhose (SisK Vlog Pantyhose Challenge EP2.2)
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07:55
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17:14
SisK Pantyhose Challenge EP3.1: Shiny White
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09:24
Vicki's JOI nasty slut challenge!
Victoria Lecherri
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01:17
Challenge for small dick losers! Cum with 5-second interval wanking! Tranny Femdom SHP!
TV_Helena
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05:23
Sissy Challenge A Task from PlayBDSM.vip
femboylina2026
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01:39
Performance test for stroke losers! Can you ruin your orgasm 10 times? JOI GERMAN DEUTSCH
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01:13
Great girl-girl show for her master! Jerk off challenge for two hot tranny girlies!
TV_Helena
53.2K views
22:30
Femboy MILF in the Ultimate Gooner Boy Challenge
Bella Roar
4K views
30:14
The 30 minutes challenge for myself - Riding the 12 inch King Cock
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40.8K views
07:56
SisK Pantyhose Challenge EP3.2: Jerking off until cum
SissyKanisa
44.3K views
03:09
A femboy try on coffee color pantyhose (SisK Vlog Pantyhose Challenge EP2.1)
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16:00
2022 Christmas Cum Eating Challenge CEI
April Bee
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05:26
sissy webcam challenge
Sissy Webcam Whore
1.7K views
07:12
Sissy's anal dildo challenge
Marie Julianne
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02:58
Hotel Hallway Sissy Ice Machine Challenge by Sissy Mindy
11.8K views
06:50
Finally all in with the ultimate challenge - Dick Rambone to the balls
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45:24
SISSY 22 cm VS VITTORIA 20 cm - (TGIRLS CHALLENGE 138)
zenzetosrl
52.4K views
07:23
PlayBDSM.vip Gave Me This Challenge. So I Did It in a Public Toilet
femboylina2026
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02:19
100 Punches Challenge Second Attempt in Bodystocking Fisting
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12:12
A Thai crossdresser rub her limp clitty with her new pantyhose while trying on it (SisK Vlog Pantyshose Challenge EP1)
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07:54
Submit to Daddy's Edging Challenge: POV JOI Strapon
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00:32
Playlist Edging Challenge
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04:04
ill Sophies 4 minute Cum Challenge
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01:28
AndrewMist tries a Huge Anal Plug Challenge
9.8K views
02:09
Sissy challenge 4 Days only in sissy clothes
Sissy Steffi
33.4K views
13:38
Futanari Ninja The Colosseum Challenge
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23.2K views
07:47
Playing with my booty and enjoying the moment. Another playful challenge inspired by PlayBDSM.vip
femboylina2026
2.2K views
06:21
The Princess Udders Six Minute Skittle Spank challenge
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3.7K views
00:43
You want out of your cage? Then cum in a minute! Chastity Release Challenge by sweet Tranny Girl! GERMAN
TV_Helena
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08:42
Crossdresser in chastity and his daily dildo challenge
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06:18
Big Cock TGirl Lucy and the Big Black Mamba Dildo Challenge
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09:39
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02:45
My new sissy challenge - deepthroat
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03:10
Sissy Magic Bomb Chastity Cage Challenge
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01:04
35 or more upvotes on reddit challenge
SlutyCourtney
4.2K views
03:26
The challenging task for a mature crossdresser to look beautiful for a date.
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2.1K views
09:12
WorldWide Sissy Pregnate Challenge from 666AmberRayne666
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11:15
New very thick anal plug challenge & Speculum 01-Feb-2021
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00:22
Wipe It Down Challenge (Sissy Version)
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