• Top Rated
  • Most Viewed
  • Categories
Search

Top Categories

  • Fisting
  • Strapon and Pegging
  • Feminization
  • Pussy and Ass Licking
  • Facesitting
  • Mistress and Slave
  • Dirty Talk
  • Russian
  • Blondes
  • Footjob
  • Pissing
  • Brunettes
  • Young Mistress
  • Shaved Pussy
  • Beautiful Mistress
  • Bondage
  • High Heels
  • Handjob
  • Foot and Shoe Licking
  • Sex with Mistress
  • Humiliation
  • Mature Mistress
  • Homemade
  • Whipping and Spanking
  • Rough
  • Two Mistresses
  • Cuckold
  • Japanese
  • Cock and Ball Torture
  • Medical
  • Ballbusting
  • CFNM
  • Trampling

Feminization New Videos

  • Latest
  • Most Viewed
  • Top Rated
  • Longest
  • Most Commented
  • Most Favourited
Maid pegs her crossdressing boss
12:25
92%
Maid pegs her crossdressing boss
15 hours ago
34 168
A new toy for a feminized sissy husband
16:49
93%
A new toy for a feminized sissy husband
1 day ago
44 415
Sissy boy gives a blowjob to a mistress's lover
22:00
89%
Sissy boy gives a blowjob to a mistress's lover
1 day ago
37 755
Lady fucks a sissy boy with a strap-on and teaches him to give blowjobs
8:08
94%
Lady fucks a sissy boy with a strap-on and teaches him to give blowjobs
1 day ago
37 275
Old girlfriend serves anal with a strap-on
14:31
92%
Old girlfriend serves anal with a strap-on
1 day ago
41 810
Surprise for a feminized husband
14:30
91%
Surprise for a feminized husband
1 day ago
42 173
Husband in a dress waits for his wife with a strap-on
11:51
88%
Husband in a dress waits for his wife with a strap-on
1 day ago
150 808
Strap-on girl's tips on how to handle a cock properly
17:03
88%
Strap-on girl's tips on how to handle a cock properly
1 day ago
53 616
Strap-on in the ass of a lustful crossdresser
11:50
94%
Strap-on in the ass of a lustful crossdresser
1 day ago
39 265
Sissy boy gets fucked in the ass while his mistress watches
16:39
93%
Sissy boy gets fucked in the ass while his mistress watches
1 day ago
68 328
Sissy boy gets fucked in the ass and mouth at the same time
13:21
93%
Sissy boy gets fucked in the ass and mouth at the same time
1 day ago
45 452
Sissy boy fucks his mistress's friend with a face strap-on
11:02
92%
Sissy boy fucks his mistress's friend with a face strap-on
1 day ago
38 979
Sissy boy secretary gets fucked in the ass with a strap-on
16:40
93%
Sissy boy secretary gets fucked in the ass with a strap-on
1 day ago
50 842
Sissy sluts get fucked in the ass under a mistress's supervision
19:48
86%
Sissy sluts get fucked in the ass under a mistress's supervision
1 day ago
42 906
Shocking job interview with a boss and her secretary
25:29
84%
Shocking job interview with a boss and her secretary
1 day ago
76 474
Mistress fucks a slave in a dress and stockings with a strap-on
16:20
93%
Mistress fucks a slave in a dress and stockings with a strap-on
1 day ago
77 078
Mistress and a sissy boy maid in femdom porn
23:30
91%
Mistress and a sissy boy maid in femdom porn
1 day ago
41 867
Feminized cuckold becomes a slut for his wife's lover
48:16
87%
Feminized cuckold becomes a slut for his wife's lover
1 day ago
135 304
Feminized maid gets a strap-on in her ass
11:22
97%
Feminized maid gets a strap-on in her ass
1 day ago
42 068
A mistress feminizes a young guy
27:29
86%
A mistress feminizes a young guy
1 day ago
130 802
Feminization and hot strap-on sex with a Russian mistress
13:31
95%
Feminization and hot strap-on sex with a Russian mistress
1 day ago
117 838
My husband is a sissy wimp
18:35
84%
My husband is a sissy wimp
1 day ago
138 231
Milking a tied-up slave's sperm
14:11
82%
Milking a tied-up slave's sperm
1 day ago
90 245
Two Russian college girls humiliate a feminized guy with strap-ons
15:41
90%
Two Russian college girls humiliate a feminized guy with strap-ons
1 day ago
87 828
Cum bukkake on an obedient sissy boy's face
10:17
91%
Cum bukkake on an obedient sissy boy's face
1 day ago
32 066
Three horny beauties offer to clean your teeth with their dirty brushes
0:40
83%
Three horny beauties offer to clean your teeth with their dirty brushes
1 day ago
6 210
Four beauties torment one slave at the same time
4:36
84%
Four beauties torment one slave at the same time
1 day ago
21 803
College girl fucks a dean dressed as a woman in the ass and mouth
16:55
87%
College girl fucks a dean dressed as a woman in the ass and mouth
2 days ago
60 523
Turning a guy into a cock-girl
10:20
95%
Turning a guy into a cock-girl
2 days ago
63 916
Shy or not, you'll get it in the ass
11:31
93%
Shy or not, you'll get it in the ass
2 days ago
114 155
  • 01
  • 02
  • 03
  • Next

Feminization Femdom Videos - Sissy Training

The feminization femdom category shows dominant women who dress, style and train submissive men in feminine roles. Lingerie, makeup, wigs, heels and dresses are chosen by the mistress, and the slave must accept them. All videos are free to watch online in HD, with no registration.

For many viewers the theme is about transformation and obedience. The mistress picks the outfit, applies the makeup, corrects posture and teaches how to walk, sit and speak. The slave follows instructions carefully, often embarrassed but eager to please. The process may take a whole video and often ends with a new name or a formal introduction.

Transformation stories remain a favorite of fans because they offer a clear beginning, middle and end. A man arrives in ordinary clothes, is guided through changes and finishes as a completely different character under the mistress's approval. Details such as stockings, corsets, nail polish and hairstyles are shown closely, and the dialogue often includes lessons in etiquette and obedience. Some videos are lighthearted and playful, while others are strict boot-camp style sessions with a lot of rules. Whatever your taste, this category offers many creative storylines, and the best clips are easy to find through rating and popularity sorting. New videos are added on a regular schedule. Because the stories vary so much, fans of the theme can easily follow their favorite mistresses from one makeover to another and discover how each of them builds a character step by step.

Dressed, Made Up and Trained

Scenes include dress-up sessions, makeup lessons, maid training, strapon games, humiliation and public-style embarrassment. Some mistresses are gentle teachers, others are strict and mocking. The performers are consenting adults, and the scenes are produced for entertainment, often with a warm and humorous tone alongside the strict commands.

If you enjoy this theme, take a look at our strapon and pegging, humiliation and mistress and slave categories. Sort by popularity to find the most watched videos and visit again for new additions.

Related categories: Strapon and Pegging, Humiliation, or browse all categories.

riding crop whip pantyhose and stockings submissive cuckolds cum milking made to cum barefoot trampling group sex masked slave redheads men in female clothing lingerie strapon on crossdresser brutal facesitting slave in collar pov thigh high boots huge strapon slave cumming big asses slave on leash pegging a guy chastity belt cheating wife medical femdom vibrator gag latex lesbian mistress deepthroat strapon loud moaning slaves ruthless mistress divine bitches trampling in shoes jerk off instruction sole licking big tits face slapping tattoo cums from cunnilingus femdom empire men in stockings small tits strapon sissies kicking orgasm control wife and lover watched by husband russian mistress fingering big cock slave

WifepornHD.com contains adult content. By entering, you confirm that you are at least 18 years old (or the age of majority in your jurisdiction) and that viewing adult material is legal where you live. All models appearing in the videos were 18 years of age or older at the time of filming. The videos are staged and sourced from publicly available internet sources.

  • Home
  • Invite a Friend
  • Support
  • Terms
  • Parental control
  • SITEMAP
© 2026 WifePornHD 18+ All rights reserved. Reproduction in any form is prohibited.