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Sissy Training Porn Videos (9,402)

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Femdom Pegging Latex Sissy by Dominafire
99%
14:05
Femdom Pegging Latex Sissy by Dominafire

xHamster 1 year ago

You're not a Man any More: Sissy's new Everyday Life - EP6 Transforming this Wanker: Mistress Julia
91%
3:10
You're not a Man any More: Sissy's new Everyday Life - EP6 Transforming this Wanker: Mistress Julia

Pornhub 2 years ago

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest
87%
1:33:16
Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

xHamster 1 year ago

Sissy Training
68%
12:50
Sissy Training

XNXX 9 months ago

Hot Girl Fucks Shemale Ass until he Cums!!!
91%
2:39
Hot Girl Fucks Shemale Ass until he Cums!!!

Pornhub 5 years ago

Sissy in School Uniform Cosplay Masturbates Anal while Showing "big Ass"【女装 男の娘 Anal Orgasm Femboy】
91%
3:03
Sissy in School Uniform Cosplay Masturbates Anal while Showing "big Ass"【女装 男の娘 Anal Orgasm Femboy】

Pornhub 2 years ago

Sissy Owned by Girlfriend (Sissy caption Story)
91%
4:38
Sissy Owned by Girlfriend (Sissy caption Story)

Pornhub 4 years ago

Dominant GF Wrecks BFs Asshole - Anal Punch Fisting, Double Anal Fisting (011A)
91%
7:43
Dominant GF Wrecks BFs Asshole - Anal Punch Fisting, Double Anal Fisting (011A)

Pornhub 1 year ago

Sissy Anal JOI with Ruined Orgasm and Self Facial CEI Cum Countdown
80%
17:38
Sissy Anal JOI with Ruined Orgasm and Self Facial CEI Cum Countdown

XNXX 2 years ago

12 FEMDOM TIPS for COCK
84%
18:00
12 FEMDOM TIPS for COCK

XGroovy 4 years ago

Sissy in Sexy Lingerie Fucks Cum out of Pussy with Dildo
91%
1:41
Sissy in Sexy Lingerie Fucks Cum out of Pussy with Dildo

Pornhub 3 years ago

Milk ENEMA bath for SISSY slave with full CONDOM inside his ass
98%
13:41
Milk ENEMA bath for SISSY slave with full CONDOM inside his ass

xHamster 1 year ago

Taboo Female Supremacy | Penny Barber
91%
16:00
Taboo Female Supremacy | Penny Barber

Pornhub 3 years ago

Beta 101 - the Beginner’s Guide to becoming the Perfect Beta
91%
21:51
Beta 101 - the Beginner’s Guide to becoming the Perfect Beta

Pornhub 1 year ago

Sissy Anal Slut Training (Sissy caption Story)
91%
7:52
Sissy Anal Slut Training (Sissy caption Story)

Pornhub 4 years ago

Worship Big White Cock 2
94%
17:14
Worship Big White Cock 2

SpankBang 4 years ago

2022 Femdom Cumshots Compilation
91%
12:07
2022 Femdom Cumshots Compilation

Pornhub 3 years ago

“put on some Panties you Sissy” SPH Sissification Humiliation Femdom JOI
90%
7:05
“put on some Panties you Sissy” SPH Sissification Humiliation Femdom JOI

Pornhub 6 months ago

Sissy Wife Blowjob Practice - Clara Dee JOI
96%
7:42
Sissy Wife Blowjob Practice - Clara Dee JOI

xHamster 2 years ago

The Faggot's Wheel
91%
9:36
The Faggot's Wheel

Pornhub 3 years ago

Русский транс дрочит член
91%
6:29
Русский транс дрочит член

Pornhub 3 years ago

Pegged in Pink - Sissy Pegging POV
97%
12:19
Pegged in Pink - Sissy Pegging POV

xHamster 1 year ago

Pegged in Pink - Sissy Pegging POV
97%
12:19
Pegged in Pink - Sissy Pegging POV

xHamster 1 year ago

Bitch boi husband dresses up as a sissy bitch and pegged in his tight boi pussy
99%
2:34
Bitch boi husband dresses up as a sissy bitch and pegged in his tight boi pussy

xHamster 3 years ago

Femboy Sissy Slut Stripped, Humiliated, Fingered, Facefucked & Pegged
91%
13:06
Femboy Sissy Slut Stripped, Humiliated, Fingered, Facefucked & Pegged

Pornhub 1 year ago

The Art Of Sucking Dick (Sissy Suggestion)
97%
5:41
The Art Of Sucking Dick (Sissy Suggestion)

xHamster 5 years ago

Self-Sucking & Sissygasm Compilation Jessica Bloom #2
91%
5:19
Self-Sucking & Sissygasm Compilation Jessica Bloom #2

Pornhub 2 years ago

Homemade Sissygasm i Fuck her Ass until her Dick Flows
91%
0:21
Homemade Sissygasm i Fuck her Ass until her Dick Flows

Pornhub 5 years ago

Tight Sissy Pegged while Gagged in Cuffs on Bench with Huge Bad Dragon Strapon by Mistress Mercer
91%
2:53
Tight Sissy Pegged while Gagged in Cuffs on Bench with Huge Bad Dragon Strapon by Mistress Mercer

Pornhub 3 years ago

Cuckold Sissyslut like to take it both Ways. Sucking and Fucking.
91%
10:26
Cuckold Sissyslut like to take it both Ways. Sucking and Fucking.

Pornhub 3 years ago

Sissy clit bitch boi gets humiliated & his boi pussy pegged
99%
2:06
Sissy clit bitch boi gets humiliated & his boi pussy pegged

xHamster 2 years ago

Sissy faggot husband gets fucked in his ass
99%
1:34
Sissy faggot husband gets fucked in his ass

xHamster 1 year ago

Red Lipstick for Sissy
95%
5:16
Red Lipstick for Sissy

xHamster 2 years ago

Pegged in Pink - Sissy Pegging POV - Elle Eros
91%
12:16
Pegged in Pink - Sissy Pegging POV - Elle Eros

Pornhub 2 years ago

Christmas Spirit Turns you and your Wife's Body how it should be [futa Anal JOI]
91%
25:06
Christmas Spirit Turns you and your Wife's Body how it should be [futa Anal JOI]

Pornhub 1 year ago

Sissy Wife's First Anal JOI - Clara Dee JOI
69%
17:38
Sissy Wife's First Anal JOI - Clara Dee JOI

XVideos 2 years ago

Feminine for Mommy - FEMDOM FEMINIZATION
91%
8:52
Feminine for Mommy - FEMDOM FEMINIZATION

Pornhub 2 years ago

Sissy Mantras Mindwash - Femdom POV Mindfuck for Sissies
91%
8:42
Sissy Mantras Mindwash - Femdom POV Mindfuck for Sissies

Pornhub 1 year ago

QOS Sissy Lola Crystals Gets 2nd Creampie from HUGE BBC Fuckbuddy
91%
3:07
QOS Sissy Lola Crystals Gets 2nd Creampie from HUGE BBC Fuckbuddy

Pornhub 3 years ago

SISSY Shopping List - 5 Essential Items for NEW Sissy Girls (teaser)
90%
7:18
SISSY Shopping List - 5 Essential Items for NEW Sissy Girls (teaser)

Pornhub 11 months ago

Look at you wearing my panties you sissy bitch...GoddessLola
96%
11:02
Look at you wearing my panties you sissy bitch...GoddessLola

xHamster 1 year ago

Goddess JanneAllen Turns you into a Cock Sucker
91%
18:37
Goddess JanneAllen Turns you into a Cock Sucker

Pornhub 2 years ago

Dominant Wife Ruins her Husband's Ass with HUGE Dildos
91%
13:28
Dominant Wife Ruins her Husband's Ass with HUGE Dildos

Pornhub 2 years ago

Amazing CUMshot Compilation
91%
5:26
Amazing CUMshot Compilation

Pornhub 5 years ago

Hot Cumshot Compilation of Wet Orgasms Bitch Femboy Sissygasm Slut Ass
91%
10:21
Hot Cumshot Compilation of Wet Orgasms Bitch Femboy Sissygasm Slut Ass

Pornhub 6 years ago

Sissy Slut Huge Dildo Sucking Training JOI
91%
8:48
Sissy Slut Huge Dildo Sucking Training JOI

Pornhub 3 years ago

Ria Bentley Pile Drives sub TGirl Thea Daze into Submission
91%
7:03
Ria Bentley Pile Drives sub TGirl Thea Daze into Submission

Pornhub 1 year ago

My Boyfriend wants to Dress like a Slut
91%
2:43
My Boyfriend wants to Dress like a Slut

Pornhub 2 years ago

Dominafire Rough Pegging her Pantyhose Sissy
91%
2:38
Dominafire Rough Pegging her Pantyhose Sissy

Pornhub 3 years ago

Turning Son into Sissy - Femdom - Goddess Alexa
91%
6:00
Turning Son into Sissy - Femdom - Goddess Alexa

Pornhub 4 years ago

Double Domme Spanking, Pegging, and Finger Banging, oh My!
91%
0:33
Double Domme Spanking, Pegging, and Finger Banging, oh My!

Pornhub 2 years ago

Turning my Boyfriend into my Girlfriend and Pegging him like a Slut.
91%
4:14
Turning my Boyfriend into my Girlfriend and Pegging him like a Slut.

Pornhub 4 years ago

Positive Femdom - Affirmation for Sissies - Stop trying to be a Man
91%
2:50
Positive Femdom - Affirmation for Sissies - Stop trying to be a Man

Pornhub 3 years ago

Femdom Orgasm Control - FULL CONTROL OF YOUR COCK
90%
6:11
Femdom Orgasm Control - FULL CONTROL OF YOUR COCK

Pornhub 1 year ago

Sissyfication. Part 1.
91%
10:55
Sissyfication. Part 1.

Pornhub 2 years ago

Bi Confusion Sissy Cock Sucking Trainer POV Cum On Face (Whispers Positive Instructions No Insults)
84%
15:22
Bi Confusion Sissy Cock Sucking Trainer POV Cum On Face (Whispers Positive Instructions No Insults)

FapCat 4 years ago

Playing Dress up with My Step Brother (slut Diaries Ep08)
99%
15:30
Playing Dress up with My Step Brother (slut Diaries Ep08)

xHamster 1 year ago

Playing Dress up with My Step Brother (slut Diaries Ep08)
99%
15:30
Playing Dress up with My Step Brother (slut Diaries Ep08)

xHamster 1 year ago

Step Mom Sissification Roleplay - Femdom Sissy POV - Goddess Alexa
91%
8:08
Step Mom Sissification Roleplay - Femdom Sissy POV - Goddess Alexa

Pornhub 3 years ago

Sissy - Be Confused and Try Not To Cum
96%
7:19
Sissy - Be Confused and Try Not To Cum

xHamster 5 years ago

Sissy Faggot Fuckdoll for Mistress Encouraged Bi Sissy Whore Femdom Training
91%
14:05
Sissy Faggot Fuckdoll for Mistress Encouraged Bi Sissy Whore Femdom Training

Pornhub 3 years ago

Sissy - Be Confused and Try Not To Cum
96%
7:19
Sissy - Be Confused and Try Not To Cum

xHamster 5 years ago

Crossdressing Sissy Hoe Strokes Tiny Dick and Nuts on Mirror
91%
1:49
Crossdressing Sissy Hoe Strokes Tiny Dick and Nuts on Mirror

Pornhub 3 years ago

Sissy Cuckold Story and Cum Eating
76%
11:29
Sissy Cuckold Story and Cum Eating

XNXX 2 years ago

Sissy Cums twice while Mister Watches Her!
91%
1:26
Sissy Cums twice while Mister Watches Her!

Pornhub 4 years ago

Sissy Caption Story: 1 Month
96%
29:17
Sissy Caption Story: 1 Month

xHamster 5 years ago

You are now my property!
89%
6:39
You are now my property!

xHamster 2 years ago

Daddy Talk: Daddys special dirty playtime fucked my sissy ass
79%
11:18
Daddy Talk: Daddys special dirty playtime fucked my sissy ass

XVideos 2 years ago

MILKED AND EAT OWN CUM
91%
5:23
MILKED AND EAT OWN CUM

Pornhub 3 years ago

Vends-ta-culotte - Introduction to feminization by a young and pretty French dominatrix
91%
11:23
Vends-ta-culotte - Introduction to feminization by a young and pretty French dominatrix

xHamster 1 year ago

Anal Orgasm Prostate Dildo Double Sissygasm Fuck Machine Deep Anal Fucking makes him Cum twice
91%
7:32
Anal Orgasm Prostate Dildo Double Sissygasm Fuck Machine Deep Anal Fucking makes him Cum twice

Pornhub 2 years ago

I Tease and Squeeze his little sissy balls
94%
8:59
I Tease and Squeeze his little sissy balls

xHamster 1 year ago

Intense SISSYGASM on Huge BBC Dildo!
91%
23:33
Intense SISSYGASM on Huge BBC Dildo!

Pornhub 2 years ago

Femboy in Heels Fucked HARD by Fuck Machine with HUGE Rosebud - Pornhub Gay
91%
21:10
Femboy in Heels Fucked HARD by Fuck Machine with HUGE Rosebud - Pornhub Gay

Pornhub 3 years ago

Sissy Training
91%
7:04
Sissy Training

Pornhub 3 years ago

XXXBat mistress uses a big gape plug from DKink to insert various toys into the ass of her boyfriend while he is in chastity cage as always without the possibility to have a normal orgasm.
80%
7:46
XXXBat mistress uses a big gape plug from DKink to insert various toys into the ass of her boyfriend while he is in chastity cage as always without the possibility to have a normal orgasm.

XNXX 3 years ago

Sissy Slut Training Part 6
94%
13:36
Sissy Slut Training Part 6

xHamster 1 year ago

BLACK COUPLES WHITE SLUTS
98%
4:58
BLACK COUPLES WHITE SLUTS

xHamster 5 years ago

Oral Sissy Workout
91%
2:13
Oral Sissy Workout

Pornhub 4 years ago

FPOV BBC Blowjob with Cumshot
91%
5:00
FPOV BBC Blowjob with Cumshot

Pornhub 1 year ago

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