Sissy Anal Training videos

Browse the most popular Sissy anal training videos in HD, ranked by views and updated regularly. Pick a video to watch it online, or try another tag to discover more.

Kiittenymph - Sissy Training

Kiittenymph - Sissy Training

19:39 · 122,416 views
Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

Secretary Pegging Cucked Boss Cumshot Humiliation BDSM

15:28 · 109,595 views
Sissy anal step by step training

Sissy anal step by step training

17:11 · 93,974 views
Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

Sissy Chastity Slave Boy Takes Huge Load in his Ass from Pegging

10:11 · 62,299 views
PROPER SISSY MASTURBATION by Jenna Chaste

PROPER SISSY MASTURBATION by Jenna Chaste

3:50 · 49,583 views
POPPERS PMV TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION

POPPERS PMV TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION

17:51 · 48,335 views
You Love Cock - Sissy Training Hypno PMV

You Love Cock - Sissy Training Hypno PMV

5:18 · 44,114 views
PMV TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION

PMV TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION

42:54 · 33,292 views
Romantic Pegging Soft Femdom Cuckhold Riding

Romantic Pegging Soft Femdom Cuckhold Riding

13:31 · 29,663 views
SISSY GIRL PLAP SISSYGASM TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION POPPERS PLAPGASM

SISSY GIRL PLAP SISSYGASM TRAINING JOI HYPNO ANAL SISSY TRANNY SHEMALE FEMINIZATION POPPERS PLAPGASM

4:00 · 27,708 views
Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

Your Futa Anal Trainer guides you through TOUGH FUTA SESSION [SAMPLE]

21:45 · 25,097 views
Work it, Sissy Bitch!

Work it, Sissy Bitch!

4:45 · 24,586 views
Late Night Pegging: Sissy Sluts Training

Late Night Pegging: Sissy Sluts Training

10:24 · 23,308 views
FemdomRAW: The Hottest Dominant Bitches

FemdomRAW: The Hottest Dominant Bitches

16:39 · 22,829 views
Anal is Magic

Anal is Magic

3:09 · 21,899 views
SISSY BBC BNWO POPPERS PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS

SISSY BBC BNWO POPPERS PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS

2:23 · 21,228 views
SISSY GETTING STRETCHED AND FUCKED DEEP BY HUBG BBC

SISSY GETTING STRETCHED AND FUCKED DEEP BY HUBG BBC

0:55 · 18,490 views
SISSY CUMSHOT PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS BBC BNWO

SISSY CUMSHOT PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS BBC BNWO

27:05 · 18,253 views
Shoving My High Heel in His Ass Pegging and Humiliating Sissy BF CUMS IN HIS OWN MOUTH

Shoving My High Heel in His Ass Pegging and Humiliating Sissy BF CUMS IN HIS OWN MOUTH

13:12 · 17,183 views
SISSY CUMSHOT PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS BBC BNWO

SISSY CUMSHOT PMV PEGGING TRAINING JOI HYPNO ANAL TRANNY SHEMALE FEMINIZATION POPPERS BBC BNWO

4:10 · 15,688 views
FAP2MYEX Vol. 02 Sasha Rose

FAP2MYEX Vol. 02 Sasha Rose

5:50 · 15,459 views
Sissy Training Dildo Sex Toy Fucking Male Cuck

Sissy Training Dildo Sex Toy Fucking Male Cuck

4:46 · 13,841 views
Sissy Delicious - The Program (Part One)

Sissy Delicious - The Program (Part One)

16:07 · 13,578 views
*Sissy Style*

*Sissy Style*

3:51 · 13,293 views