Ai Sex Chat

Sissytraining - Videos - Longest

Latest
Most Favourited
"Tara Tainton" analmasturbation, analplay, dildofucking, masturbationinstruction, sfw, sissytraining Tara s Sissy Anal Training 4 Manyvids
46:17
Tara Tainton
6.2K
"Tara Tainton" analmasturbation, analplay, d...
"Nyxi_Leon" 18and19yrsold, anal, oralservitude, sissytraining, trans Super long fuck session with my sissy manyvids
31:25
Nyxi_Leon
2.1K
"Nyxi_Leon" 18and19yrsold, anal, oralservitu...
"Nyxi_Leon" amateur, anal, fingering, sissytraining, transgender Sissy Fucktoy Long Manyvids
29:02
Nyxi_Leon
1.3K
"Nyxi_Leon" amateur, anal, fingering, sissyt...
"Nyxi_Leon" ballgagged, bondage, sissytraining, transgender, whipping Sissy Institute Ad manyvids
27:04
Nyxi_Leon
2.2K
"Nyxi_Leon" ballgagged, bondage, sissytraini...
"Lexi Snow" cei, femdom, pegging, sissytraining, slavetraining Landlady Pegs You For Payment Manyvids
25:05
Lexi Snow
11K
"Lexi Snow" cei, femdom, pegging, sissytrain...
"Tara Tainton" analmasturbation, femdompov, masturbationinstruction, sissysluts, sissytraining Tara s Sissy Anal Training for Beginners manyvids
22:43
Tara Tainton
5.6K
"Tara Tainton" analmasturbation, femdompov, ...
"Tara Tainton" crossdressing, femdompov, gendertransformation, sfw, sissification, sissytraining Transforming You into My Sweet Maid Manyvids
22:21
Tara Tainton
8.0K
"Tara Tainton" crossdressing, femdompov, gen...
femdom, friends, sissification, sissysluts, sissytraining nina crowne threesome with my sissy Manyvids
20:10
Nina Crowne
16K
femdom, friends, sissification, sissysluts, sissytra...
femdom, joi, pegging, povstrapon, sissytraining pov pegging joi Manyvids
19:54
HasmikJOI
9.1K
femdom, joi, pegging, povstrapon, sissytraining pov ...
feminization, makemebi, sfw, sissification, sissytraining, virginhumiliation goddess nikki kit virgin feminized by sex coach Manyvids
18:43
Goddess Nikki Kit
14K
feminization, makemebi, sfw, sissification, sissytra...
"Lexi Snow" blackmailfantasy, bossemployee, joi, sissysluts, sissytraining Caught Being A Sissy At Work manyvids
18:37
Lexi Snow
3.3K
"Lexi Snow" blackmailfantasy, bossemployee, ...
"JuliaCrown" crossdressing, cumeatinginstruction, feminization, sissification, sissytraining Sissification CEI Sissy training JOI manyvids
18:31
JuliaCrown
2.2K
"JuliaCrown" crossdressing, cumeatinginstruc...
Mistress slut Part1 Fetish Videos September 24, 2022 Manyvids
17:24
Fetish Videos
867
Mistress slut Part1 Fetish Videos September 24, 2022...
"SneezeGoddess" c2c, camgirl, camshow, cei, costume, cumcountdown, cumeatinginstruction, sissification, sissysluts, sissytraining C2C Sissification Fantasy manyvids
17:06
SneezeGoddess
2.0K
"SneezeGoddess" c2c, camgirl, camshow, cei, ...
Sorry no release but an ass fuck Fetish Videos September 23, 2022 Manyvids
17:01
Fetish Videos
1.1K
Sorry no release but an ass fuck Fetish Videos Septe...
"Nyxi_Leon" 18and19yrsold, anal, oralservitude, sissytraining, trans Home from the Club Manyvids
16:39
Nyxi_Leon
1.5K
"Nyxi_Leon" 18and19yrsold, anal, oralservitu...
Tormenting the Republican Sissy MistressPetraHunter March 26, 2018 Manyvids
16:27
MistressPetraHunter
617
Tormenting the Republican Sissy MistressPetraHunter ...
"HasmikJOI" cei, goddessworship, joi, sissytraining, titworship sissy encouragement cei joi femdom Manyvids
16:00
HasmikJOI
4.1K
"HasmikJOI" cei, goddessworship, joi, sissyt...
"Tara Tainton" cfnm, doctor, feminization, sfw, sissytraining, smalldicks Your Female Hormone Prescription manyvids
15:54
Tara Tainton
6.8K
"Tara Tainton" cfnm, doctor, feminization, s...
dildosucking, femdompov, feminization, imposedcrossdressing, sissytraining miss malorie switch to meet my father Manyvids
15:51
Miss Malorie Switch
19K
dildosucking, femdompov, feminization, imposedcrossd...
Dressing Up My Princess MistressPetraHunter June 06, 2021 Manyvids
15:36
MistressPetraHunter
369
Dressing Up My Princess MistressPetraHunter June 06,...
"Bambi Bluu" blackmailfantasy, cumeatinginstruction, femdom, humiliation, pegging, sissy, sissytraining, strapon, taboo, teens18plus BLACKMAIL PEGGING w SISTER FUTA manyvids
15:21
Bambi Bluu
7.1K
"Bambi Bluu" blackmailfantasy, cumeatinginst...
This BigOne fits in I ll make sure of that Fetish Videos March 23, 2025 Manyvids
15:19
Fetish Videos
1.6K
This BigOne fits in I ll make sure of that Fetish Vi...
"Nyxi_Leon" 18and19yrsold, analplay, missionary, sissytraining, trans The Bondage of Bailey Love manyvids
15:15
Nyxi_Leon
568
"Nyxi_Leon" 18and19yrsold, analplay, mission...
Maximum anal punishment Fetish Videos December 09, 2022 Manyvids
15:15
Fetish Videos
1.4K
Maximum anal punishment Fetish Videos December 09, 2...
cuckolding, financialdomination, sfw, sissification, sissysluts, sissytraining teaching my cuck to be a girl Manyvids
15:06
SneezeGoddess
5.7K
cuckolding, financialdomination, sfw, sissification,...
"SneezeGoddess" cei, cumeatinginstruction, pegging, peggingfantasy, peggingpov, sissification, sissytraining, strapon, strapongoddess, straponpov POV Vile Strap On Sissification CEI manyvids
15:06
SneezeGoddess
3.7K
"SneezeGoddess" cei, cumeatinginstruction, p...
"MissValentina" sissification, sissy, sissyboy, sissysluts, sissytraining Sissy Maid Transformation manyvids
15:05
MissValentina
2.3K
"MissValentina" sissification, sissy, sissyb...
"Nyxi_Leon" maidfetish, mistress, oralservitude, sissytraining, transgender Sissy Nyxi FEMINIZED manyvids
14:58
Nyxi_Leon
2.0K
"Nyxi_Leon" maidfetish, mistress, oralservit...
armpits, cei, doubledomination, hairyarmpits, sissytraining xkristyleex Double Domme Armpit Fetish Worship and CEI Manyvids
14:47
xkristyleex
15K
armpits, cei, doubledomination, hairyarmpits, sissyt...
"Ruby_Onyx" analplay, doubledomination, pegging, sissytraining, strapon Trixie The Office Sissy Part 3 manyvids
14:42
Ruby_Onyx
6.8K
"Ruby_Onyx" analplay, doubledomination, pegg...
Sissy stored and sexually used Fetish Videos January 18, 2025 Manyvids
14:38
Fetish Videos
2.4K
Sissy stored and sexually used Fetish Videos January...
"Annabelle Rogers" blowjob, cumontits, sissysluts, sissytraining, sph Goddess Encourages Sissy Slut To Suck Cock With Her SPH manyvids
13:56
Annabelle Rogers
4.9K
"Annabelle Rogers" blowjob, cumontits, sissy...
RubyPrincess gets feminized while babysitting & men follow orders to humiliate her
13:56
RubyPrincess
976
RubyPrincess gets feminized while babysitting & men ...
"Charlette Webb" cei, dirtytalking, pantyfetish, sissysluts, sissytraining Sissy Brad CEI Cum Support manyvids
13:35
Charlette Webb
1.1K
"Charlette Webb" cei, dirtytalking, pantyfet...
Sissy maid education Fetish Videos August 04, 2021 Manyvids
13:30
Fetish Videos
754
Sissy maid education Fetish Videos August 04, 2021 M...
Pretty Sissy Transformation MistressPetraHunter November 13, 2017 Manyvids
13:19
MistressPetraHunter
597
Pretty Sissy Transformation MistressPetraHunter Nove...
Secret FUTA Secretary 2 Turning my BOSS into a SISSY August 12, 2025 Manyvids
13:10
Tonnia
2.7K
Secret FUTA Secretary 2 Turning my BOSS into a SISSY...
"JuliaCrown" femdom, sfw, sissification, sissy, sissytraining, sluttraining Ass To Mouth sissy anal training manyvids
13:06
JuliaCrown
2.4K
"JuliaCrown" femdom, sfw, sissification, sis...
Sissy Aftercare MistressPetraHunter September 11, 2020 Manyvids
12:59
MistressPetraHunter
271
Sissy Aftercare MistressPetraHunter September 11, 20...
They must suck each other s cocks Fetish Videos March 29, 2025 Manyvids
12:42
Fetish Videos
3.4K
They must suck each other s cocks Fetish Videos Marc...
"kristenwylde" cumcountdown, femdom, joi, sissytraining, strapon joi while i make you suck my dildo manyvids
12:38
kristenwylde
1.5K
"kristenwylde" cumcountdown, femdom, joi, si...
Sissy Hormones and Castration for You lucyaura April 23, 2021 Manyvids
12:37
lucyaura
2.6K
Sissy Hormones and Castration for You lucyaura April...
Rubber Sissy has to suck her first real cock Fetish Videos August 19, 2025 Manyvids
12:31
Fetish Videos
1.6K
Rubber Sissy has to suck her first real cock Fetish ...
"Lexi Snow" femdompov, pegging, sfw, sissyboy, sissysluts, sissytraining Unveiling Party For My Sissy manyvids
12:28
Lexi Snow
7.6K
"Lexi Snow" femdompov, pegging, sfw, sissybo...
"SavannahxSiren" analplay, femdompov, redhead, sissysluts, sissytraining Sissy Slut Anal Training manyvids
12:23
SavannahxSiren
1.5K
"SavannahxSiren" analplay, femdompov, redhea...
Sissy is trained to suck the first real cock Fetish Videos August 19, 2025 Manyvids
12:23
Fetish Videos
1.2K
Sissy is trained to suck the first real cock Fetish ...