Most Popular Sissy training XXX Videos. Page 2.

Showing 25-48 Of 109 For 'Sissy training'

Shemale Sissy Training - Step by Step guide to becoming a sissy

07:23

Shemale Sissy Training - Step by Step guide to becoming a sissy

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Femdom Pegging and Anal Play in a Compilation of Bondage and Pleasure

05:09

Femdom Pegging and Anal Play in a Compilation of Bondage and Pleasure

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Sensual Mistress Training with Smooth Skin

13:11

Sensual Mistress Training with Smooth Skin

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Part 8 of the institution x anal prostate milking compilation

05:00

Part 8 of the institution x anal prostate milking compilation

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Sissy ballerina gets humiliated by dallas dominatrix

09:09

Sissy ballerina gets humiliated by dallas dominatrix

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Nylon mistress teases and humiliates with foot wrosh instructions

10:21

Nylon mistress teases and humiliates with foot wrosh instructions

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Femdom femdom dominates sissy in chastity cage and cock milking

06:01

Femdom femdom dominates sissy in chastity cage and cock milking

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My French maid uniform is perfect for you to dress up as a sissy boy

07:07

My French maid uniform is perfect for you to dress up as a sissy boy

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Older Mistress Gives Sissy Training in POV

06:12

Older Mistress Gives Sissy Training in POV

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Part 10 of the Compilation: College Girls and Femdoms in Anal Training

05:00

Part 10 of the Compilation: College Girls and Femdoms in Anal Training

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Part 2 of College Anal Play with Strapon and Orgasmic Milking

04:19

Part 2 of College Anal Play with Strapon and Orgasmic Milking

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Cuckold mistress gives jerk off instructions to her sissy slave

09:55

Cuckold mistress gives jerk off instructions to her sissy slave

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Sissy training under a femdom mistress' guidance

08:42

Sissy training under a femdom mistress' guidance

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Older dominant mistress dominates her sissy slave on Thursday

12:18

Older dominant mistress dominates her sissy slave on Thursday

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Compilation of Anal Training and Ass Play with Strapon

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Compilation of Anal Training and Ass Play with Strapon

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Older sissy gets dominated and humiliated

08:10

Older sissy gets dominated and humiliated

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Lesbian anal play and penetration in part 32 of this compilation - institution x

09:59

Lesbian anal play and penetration in part 32 of this compilation - institution x

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Femdom Mistress Teases Her Submissive Slave

07:25

Femdom Mistress Teases Her Submissive Slave

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Cuckolded mistress will humiliate her sissy slave

06:47

Cuckolded mistress will humiliate her sissy slave

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Dominant mom humiliates sissy with dirty talk and milking

09:48

Dominant mom humiliates sissy with dirty talk and milking

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A sissy's training session with Lady Latte, the femdom dominatrix in this POV video

09:41

A sissy's training session with Lady Latte, the femdom dominatrix in this POV video

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Cuckolded mistress gives you jerk off instructions from her goddess

10:23

Cuckolded mistress gives you jerk off instructions from her goddess

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11:23

Older woman dominates young sissy with strapon

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Femdom mistress teases and humiliates her sissy slave in fetish video

08:09

Femdom mistress teases and humiliates her sissy slave in fetish video

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