Sissy Training 1,731 videos

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06:05 69%

Dominatrix Allows Him To fuck Her Cuckold Hard Without A Condom

8 months ago
xHamster
femdom, bisexual, wife, neighbor
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Gentle Bi Encouragement - Will You Suck Cock For Me?

2 months ago
xHamster
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On the public beach, my husband has to keep the chastity cage

11 months ago
xHamster
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07:39 74%

Pump 2 Me - Sissy GOON Trainer

4 years ago
xHamster
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20:16 90%

High Class Sissy Trained - Mistress T

3 years ago
TXXX
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17:24 69%

Mistress Turns out her Slave for Face Fucking, Ass Play, and Facials

6 years ago
TrannyGem
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07:19 85%

Extreme Pegging & Fisting Compilation - Femdom fucks male sub anal whore with Huge cock

6 months ago
xHamster
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Sissy slut workout day fucked deep in her ass with my BBC

1 month ago
xHamster
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06:14 67%

Why is she scared of femboy sissy's cumshot?

2 years ago
xHamster
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My husband has an artificial cock

8 months ago
xHamster
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06:36 78%

Domme Victoria Rey Collars, gags, abases, spits on her steamy chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

2 months ago
HDSex
femdom, small cock, train, gagging, husband, panties, domination
07:17 73%

My Cuckold Slave Cleanup Cum From My Pussy and Beverage My Piss and Licks My Pussy Clean

11 months ago
xHamster
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13:04 46%

Two Mistress's and a Sissy Whore

1 month ago
xHamster
femdom, strapon, train, crossdresser, whore, pegging, slut
15:29 61%

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10 months ago
xHamster
bisexual, train, sissy, blindfolded
1:28:40 67%

Kinky Carmen In Sissy Bitch Training By

3 years ago
TXXX
femdom, train, sissy, kinky
11:16

I Will Make You Suck His Cock, Slave! You Must Please Me! Arya Grander

2 months ago
xHamster
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05:49 38%

On the beach I turn my husband's cock into pussy

1 year ago
xHamster
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09:44 79%

Sunday Humiliation for Sissy husband Full

2 months ago
xHamster
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05:49 47%

Watch Me Become Your Mistress

1 year ago
xHamster
gloves, boots, sissy, femdom
03:14 64%

Happy Hour with Apologetic Domme - a short chastity love story

1 year ago
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Sissy training

6 years ago
xHamster
bisexual, train, sissy
16:20 62%

Girl dominate sissy girls and fuck them

3 months ago
xHamster
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06:05 81%

Cum twice in a row from cock milking with prostate fingering

1 year ago
xHamster
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11:44 55%

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2 years ago
xHamster
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23:09 58%

Sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

1 year ago
xHamster
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What to do with my lover's condom

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50:56 67%

Becky Scolds Sissy bi-atch Michel for Not Cleaning the Kitchen decently

4 months ago
VideoSection
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01:09 48%

Femdom futa Mommy pegs you and makes you her cocksucking sissy slut - full video on veggiebabyy Manyvids

2 years ago
xHamster
pegging, futanari, 3D
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Training Sissy To Be A Good Whore For Her B.f

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Mrs Loving Begins Sissy Training at Mother's Request

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xHamster
train, sissy, granny
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Sissy Maid Cuck Locked in Chastity and Pegged By Hot Milf

10 months ago
xHamster
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06:50

You are my sissy whore and will pimp you out !!!

10 months ago
xHamster
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Become My Sissy Bimbo Beta Bitch - Sissification & Feminization with Lady Julina

1 year ago
xHamster
pantyhose, rubber, crossdresser, nylon
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Tied Up Sissy Gets Wanked Off

1 year ago
xHamster
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Sissy Training - Sucking That Dick and Swallow the Load

5 years ago
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sissy, teen (18+), swallow, train
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Miss Alessa Milano Sissy Bitch Blowjob StrapOn feed used Condoms Part 1

2 weeks ago
xHamster
femdom, latex, strapon, train, CFNM, condom, domination
08:50 78%

Cum training my cock tease

10 months ago
xHamster
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The final transformation - Mistress Tatjana

1 year ago
xHamster
femdom, rubber, strapon, chastity, bondage, sissy
15:28 64%

Mistress trained her new sissy slave bitch

3 years ago
VipTube
train, sissy, femdom
12:30

Therapy session for sissy boys

1 year ago
xHamster
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Checking Locked Dick and Strapon

9 months ago
xHamster
femdom, BDSM, domination, sissy
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12 months ago
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02:38 84%

Cristal Kinky playing with my latex sissy doll Preview

3 years ago
xHamster
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05:35

I widen my husband's ass

11 months ago
xHamster
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09:27 50%

I like colorful my cuckold husband's buttocks

1 month ago
xHamster
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57:05 45%

WHITE COCK BRAINWASH - Redux

4 years ago
xHamster
train, sissy, cum in mouth
05:35 92%

A girl in black boots fucks a guy in a chastity belt hard

2 years ago
xHamster
femdom, boots, sissy, chastity
1:10:38 68%

Sissy Training Day

2 years ago
TXXX
femdom, BDSM, sissy, train
03:28 68%

FUCK ME POV

2 years ago
xHamster
crossdresser, lesbian, domination, bisexual, pegging
55:00 78%

Prostate Milking Anal Training Pspot Orgasm - INSTITUTION X - COMPILATION 1 - 2

2 years ago
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femdom, train, prostate, BDSM, milk, handjob compilation, machine
04:22

Sissy training: The urge to suck

7 years ago
xHamster
sissy
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Sasha De Sade Sissy Inspection Hot!

5 years ago
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femdom, train, bondage, crossdresser, sissy, BDSM
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Arab woman humiliates submissive client in Paris

9 months ago
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femdom, french, train, sissy, kinky, arab
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Slut Training My Sissy Sluts Ass + Whipping

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HClips
femdom, latex, strapon, pegging, sissy, BDSM
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Mrs Loving Begins Sissy Training at Mother s Request

8 years ago
TXXX
femdom, train, sissy
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Sissy cumslut training

5 years ago
TXXX
train, sissy
06:45

Put these stockings and mini skirt on if you want me to make you cum

7 months ago
xHamster
mature, BBW, bisexual, chubby, skirt
12:52 86%

I put him in Pink Panties and started Pegging him

1 month ago
xHamster
pegging, sissy, chastity, german, femdom, anal
23:09

Sissy training, I transform my husband into a real sissy. I fuck him and make him suck like a slut!

3 weeks ago
XXXDan
pantyhose, femdom, strapon, train, bondage, dildo
06:34

Mistress Victoria Rey Collars, gags, humiliates, spits on her hot chastity sissy slave husband. SPH loser Chastity Pt 1 of 5

2 months ago
xHamster
femdom, train, gagging, lingerie, cuckold, husband, dirty talk
14:05 68%

Femdom Pegging Latex Sissy by Dominafire

6 months ago
xHamster
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07:50

Married couple home pegging training

6 months ago
xHamster
czech, BDSM, pegging, sissy
08:09

Dominatrix Mistress April - Two Mistresses and a Sissy Whore P2

3 weeks ago
xHamster
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09:23 58%

Sissy Date

4 years ago
xHamster
JOI, sissy, BDSM
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Sissy Cuck Clean Creampie After Wife's Date

7 months ago
xHamster
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05:23 60%

The cuckold licks the lover's sperm

11 months ago
xHamster
homemade, wife, cuckold, husband, sissy
08:55 44%

She spread Her Pussy wide to be pleased by Her Sissy in swimsuit and tights

8 months ago
xHamster
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05:16 55%

Stepmother helps her horny sissy stepson cum hard

7 months ago
xHamster
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32:55 52%

Girlcock Hypnosis Pt.7: 555 Foxy Babes (and their cocks!)

4 years ago
xHamster
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10:28 54%

Tonguing my Jizm after Toying with my Budding Sissy Puffies

4 years ago
TrannyGem
train, nipples, puffy nipples, sissy, hands free
23:48

Sissy Maid Femdom Pegging Compilation

9 months ago
xHamster
maid, femdom, pegging, compilation, sissy, strapon
10:29

Fuck Doll Training - Prepped for Crossdressing Bisex Deepthroat

1 week ago
$$ FapHouse
sissy, kinky, blindfolded, crossdresser, femdom
03:06 84%

Sissy Training Cock Sucking

3 years ago
PornL
sissy, handjob
19:26

SISSY TRAINING...EAT YOUR OWN CUM

8 months ago
SunPorno
train, sissy, kissing
05:50 53%

My husband is getting used to his girly panties

7 months ago
xHamster
femdom, cougar, sissy, chastity
10:21 38%

Cum eating cock tease warm up

10 months ago
xHamster
femdom, strapon, bisexual, cuckold, sissy, american
08:50

Sexy Wife with Big Strapon pegging her Husband with Handjob

2 months ago
xHamster
husband, mom, pegging, anal, polish, handjob
12:01 44%

Dominatrix Mistress April - cane Training Day 3

1 year ago
xHamster
latex, domination, enema, sissy, german, bondage
10:40 78%

ASMR sloppy caged cuck chastity cum (locktober final reward)

1 year ago
xHamster
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30:40 42%

30 minute extrem ass training from Sissy "D"

8 months ago
xHamster
bondage, sissy, german
14:09 75%

Cum Addict, by Jlodalisque

4 years ago
xHamster
instruction, compilation, sissy
47:59 62%

Sissy Maid Cleaning for 2 Warm Dominatrixes

4 years ago
TrannyGem
femdom, french, train, gagging, bondage, spanking, sissy
05:20 60%

BBW stepmom sissy Training with strap on dildo - crossdresser fucked

1 year ago
xHamster
crossdresser, sissy, desi, BBW, dildo
11:24 62%

Only Pegging

1 year ago
xHamster
boots, pegging, sissy, BDSM, heels
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I fuck a stranger in a parking lot to humiliate my husband

11 months ago
xHamster
homemade, stranger, cheating, train
13:58

Milf Pegging and Anal Training Sissy

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xHamster
strapon, pegging, femdom, sissy
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Stars Of Salvation - Ep.2 - The Awakening By MissKitty2K

8 months ago
xHamster
train, anime, japanese mom, sissy, cartoon, 3D
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I Will Make You Suck His Cock, Slave! You Must Please Me! Arya Grander

3 months ago
xHamster
spandex, feet, bisexual
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You Will Be Wearing a Headscarf Today Sissy Kelly

11 months ago
xHamster
train, granny, panties, sissy, lipstick
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My first introduction to Lady Mell B

4 years ago
xHamster
train, vibrator, sissy, chastity, femdom, maid
17:46 74%

Admission of being a Sissy - Mean girls

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xHamster
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12:50 70%

NEW sissy gets deflowered with monster DILDO

1 month ago
xHamster
german, sissy, pegging, femdom, amateur
07:36 44%

Gagging Sissy Girl With My Huge Long Dick Down Her Throat

3 years ago
xHamster
sissy, panties, bra, dildo
07:25 55%

Sissy tramp instructing

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VideoSection
bisexual, instruction, sissy, femdom, train
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French Cuckold Wife And Lesbian Anal Sissy

1 year ago
xHamster
train, cuckold, lesbian
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I destroy my husband's ass

1 year ago
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femdom, leather, pegging, BDSM, cuckold, cougar, sissy
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Sissy Cock Training

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xHamster
sissy, beauty
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Mistresst - High Class Sissy Trained

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InPorn
femdom, sissy
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Pegging Femboy and Making Him Lick Ass and Pussy

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xHamster
ass, pegging, ass licking, sissy
05:27

Fuck Doll Training - Prepped for Crossdressing Bisex Deepthroat

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xHamster
femdom, cuckold, crossdresser, bisexual
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Bisexual husband gets fucked by three strapons

10 months ago
xHamster
femdom, bisexual, czech, pegging, sissy
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Slave fucking and dick locked in chastity belt

5 months ago
xHamster
strapon, mature anal, czech, BDSM, chastity, sissy
13:30

Fantastic pulsating ruined orgasm with spikes chastity on big dick. Amateur femdom handjob

1 week ago
xHamster
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15:49

Wife Swap Strapon Slave Husband

1 year ago
xHamster
wife swap, pegging, sissy
11:12

Femdom POV: Sissification, Dirty Talk, Sph, CEI, JOI. Arya Grander and Mistress Priest

10 months ago
xHamster
rubber, instruction, JOI, sissy, lesbian
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Sissygasm Tutorial - Sissification with the Lady of Feminization

2 years ago
xHamster
instruction, spandex, nylon, sissy, bra, latex
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A GangBang for the Sissy Slut

4 years ago
xHamster
latex, strapon, sissy, chastity, bondage
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Maitresse Julia - Femdom - Teasing, Edging, Denial and Facesitiing for my Sissy Slave in Chastity Cage !

2 years ago
xHamster
train, sissy, chastity, pantyhose, BDSM
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Domina Liza - Sissy Maid Caning Training - Femdom

1 year ago
DrTuber
femdom, spanking, sissy
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Scene 1 - Sissy Dreamland - Punk rock dominates & makes feminized femboy suck BBC strapon dildo

6 months ago
xHamster
strapon, femdom, sissy, cuckold, mom
02:21 56%

Couple in Pantyhose - Wife in Nylons gives Crossdressing Hubby a Handjob

2 years ago
xHamster
mature, crossdresser, sissy, cougar
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Sissy Training at Work

1 year ago
xHamster
pegging, JOI, sissy, femdom
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BBC Broken by Drogon

4 years ago
xHamster
sissy, double penetration, pissing
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Mistress Mommy Spanks Round Sissy Ass

4 years ago
xHamster
crossdresser, sissy, pantyhose
08:31

Sissy Secretary: Submissive Male Feminized into Bimbo for Job Interview, Learns how to Pee Like a Girl, Bonus Pegging & Fisting

6 months ago
xHamster
sissy, pegging, femdom, fisting, pissing
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Sissy would not swallow

4 years ago
xHamster
bisexual, sissy, chastity, BDSM, femdom
07:35

Arabic mistress wants to fuck submissive bisexual guys in their asshole

8 months ago
xHamster
arab, femdom
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Sissy anal step by step training

5 years ago
JizzBunker
train, sissy
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SISSY JOI

6 months ago
xHamster
bisexual, CFNM, BDSM, cuckold, sissy
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Dominatrix Mistress April - Rose Garden Part one

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femdom, bondage, BDSM, domination, sissy

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