© Pornhub.com, 2025

English

English
Bulgarian
Croatian
Czech
Danish
Dutch
Estonian
Finnish
French
German
Greek
Hungarian
Italian
Latvian
Lithuanian
Polish
Portuguese
Romanian
Slovak
Slovenian
Spanish
Swedish
Russian
Japanese
Chinese
Maltese
Irish

This is an adult website

This website contains age-restricted materials including nudity and explicit depictions of sexual activity. By entering, you affirm that you are at least 18 years of age or the age of majority in the jurisdiction you are accessing the website from and you consent to viewing sexually explicit content.

I am under 18 - Exit

Our parental controls page explains how you can easily
block access to this site.

© Pornhub.com, 2025

English

English
Bulgarian
Croatian
Czech
Danish
Dutch
Estonian
Finnish
French
German
Greek
Hungarian
Italian
Latvian
Lithuanian
Polish
Portuguese
Romanian
Slovak
Slovenian
Spanish
Swedish
Russian
Japanese
Chinese
Maltese
Irish

Video poster

Sissy Owned By Girlfriend (Sissy Caption Story)

04:38

AD - 00:00

No valid sources are available for this video.

Resume

Sissy Owned By Girlfriend (Sissy Caption Story)

319K Views

80%

3 years ago

685

167

621

Added to your Favorites

Video Liked View liked videos Video Liked! Sign up to store more Liked Videos Sign up

Login or Sign Up now to add this video!

Login or Sign Up now to add this video to stream!

Close

Jump to your favorite action

Close

Alyssa Bloom TS

30 Videos 7.9K Subscribers

Categories

Amateur Anal Big Ass Exclusive Fetish Hardcore Masturbation Toys Transgender Verified Amateurs

Suggest

Vote on categories

Submit

Pornstars

Thank you for your suggestions! Our team is reviewing them!

Tags

sissy sissy training sissy captions sissy caption story femdom fetish submissive slut anal sex toys gay anal transgender gay amateur hardcore tgirl sissy feminization

Suggest

Vote on tags

Sissy
Sissy training
Sissy captions
Sissy caption story
Femdom
Fetish
Submissive slut
Anal
Sex toys
Gay anal
Transgender
Gay amateur
Hardcore
Tgirl
Sissy feminization

Submit

Production

homemade

Suggest

Vote on production

Professional
Homemade

Added on 3 years ago

View more

7:20 RU

Yanasissy21

572K

90%

1 year ago

put 2 hands in the ass of her sissy bitch. fisting
1:07

Traviezisha

34.5K

83%

3 years ago

Do you want to be a sissy?

Related
Recommended
Comments

6:47

Michelle Flowers

149K

84%

1 year ago

Sissy Super Model - Feminization Captions
0:29

Alyssa Bloom TS

228

60%

1 month ago

🍆✨Cumming in From a New Angle😏🍑
5:00

Alyssa Bloom TS

1.8K

100%

3 weeks ago

Roommate Feminizes You and Forces You to be His Girlfriend (Sissy Caption Story)
0:20

aeroclam

102K

85%

2 years ago

Sissy caption
5:41

Alyssa Bloom TS

238K

76%

3 years ago

Sissified By My New Roomate (Sissy Caption Story)
13:06

Alyssa Bloom TS

243K

82%

3 years ago

Bambi Sissy Transformation (Sissy Caption Story)
0:57

Alyssa Bloom TS

11.6K

71%

1 year ago

Your New Girlfriend is a Cuckold Trainer - A Horny Caption Story 😈👄⛓️💗
0:57

Alyssa Bloom TS

24.1K

83%

1 year ago

Feminized By New Stepfather - A Sissy Caption Story 💘😏🍆
9:17

Alyssa Bloom TS

32.2K

77%

3 years ago

Train Your Sissy Pussy (Sissy Caption Story)
0:28

secretlyvanessa

795

100%

1 week ago

(*Sissy Captions*) Fulfilling your purpose
6:42

Alyssa Bloom TS

30.1K

88%

2 years ago

Sissy Becomes Feminized For The Love Of Cock - Sissy Caption Story
7:14

Alyssa Bloom TS

35.2K

73%

3 years ago

Sissy Mind Control (Sissy Caption Story)
9:44

SissyMilana

5M

90%

1 year ago

Shemale sex with mistress, Shemale Cumming Cowgirl Riding, Sissy cum in pusssy
1:10

Evelyn Tumbles

1.1M

93%

2 years ago

sissy gets caged and trained by a femboy
4:28

Daniela Chanel

7.2M

89%

1 year ago

Daniela Chanel gets thick cock sucked by horny boyfriend before he shoots hot load in her ass.
8:31

SissyMilana

3.9M

92%

4 months ago

Femdom Mistress fucks bitch sissy ass, double cum anal orgasm
5:11

Alyssa Bloom TS

99K

80%

3 years ago

Caught And Disciplined (Sissy Caption Story)
7:26

Alyssa Bloom TS

55.3K

83%

3 years ago

Sissy Slut Addiction (Sissy Caption Story)
7:42

Alyssa Bloom TS

65K

74%

3 years ago

Recruited By Shemale Mistress - (Sissy Caption Story)
7:29

Alyssa Bloom TS

143K

79%

3 years ago

Caught In The Act (Sissy Caption Story)
8:12

FemboyGebby

2.3M

92%

1 year ago

Femboy gets remotely edged! We live in the future!
3:03

mandyletspandy

20.7K

77%

3 years ago

Sissy Slut Femboy Caption Story PMV Compilation
4:43

KissMySissyPeach

1.9M

89%

2 years ago

PMV Slut Pop - Sissy Peach fuck along
4:36

SissyMilana

5M

89%

1 year ago

Best Pegged Sissy hand free cum transgirl cum
9:42

puppygirlXO

2.6M

88%

1 year ago

POV-Trans girlfriend tries to get him to stop flirting with her gf- deep throat and fucked
11:55

FemboyGebby

2.4M

93%

8 months ago

Twitchy Femboy gets ruthlessly edged by toy!
5:19 JA

shinen2022

3.6M

84%

1 year ago

【Onimai】 Mahiro-chan Playing with SEX TOY💞 Hentai Cosplayer fingering Anime Japanese cosplay
3:07

Skylar737

1.3M

86%

1 year ago

how to use a fufu clip
1:05

MariahLoveCD

1.8M

90%

2 years ago

Verbal Sissy Hoe’s Bussy Makes Guy Cum in 1 Minute
8:54

SissyMilana

18.8M

88%

2 years ago

Best Shemale Sissy Cum Compilation
1:52

Giorgiadoll

1.3K

67%

7 months ago

Sissy Giorgiadoll compilation hot photos. Reblog captions for make hard cocks cum . Crossdresser ass
3:44

Michelle Flowers

1.9K

80%

1 year ago

Sissy Bimbo Maid Loves Blowjob - With Bimbo Sissy Captions
9:51

Ts Lucy Morningstar

816

100%

1 year ago

Sissy Ts lucy (show en vivo)
1:55

seriteman

9.3K

83%

4 years ago

Teen Tranny Showing off Her Shemale Cock and Pussy
3:24

Michelle Flowers

6.1K

97%

1 year ago

Sissy Bimbo Slut - Result of Feminization Training

View More

7:37

kyliesinsxxx

4.1K

85%

7 months ago

Be Careful Sissy! by Kylie Sins
4:20

Kymmy Harper

4.2M

85%

3 years ago

Daddies Little Cum Whore HUGE facial
1:15

Michelle Flowers

1.1K

86%

1 year ago

Sissy Trans Stripper Practicing Some More After Fun Night
5:19

Michelle Flowers

46.4K

84%

2 years ago

Sexy Sissy Slut - Feminization Captions
6:31

Alyssa Bloom TS

23.1K

73%

3 years ago

Female Bodysuit (Sissy Caption Story)
4:00

Michelle Flowers

18.8K

67%

2 years ago

Fun Feminization Captions
25:31

goddessmikajoi

64.5K

81%

11 months ago

Sissy training - Futa/hentai Brainwash
7:06

Ginni Wylde

165K

81%

3 years ago

Sissy Life: Be a slut for Daddy
7:38

Caileykatts

980K

91%

5 months ago

Submissive bottom gets rough sex
2:02

Daniela Chanel

997K

90%

1 year ago

Watch transgender girl let daddy use her ass pussy rough and hard
11:40

SissyMilana

1.3M

90%

1 year ago

Mistress woman fucks shemale sissy bitch
0:40

secretlyvanessa

2.5K

100%

1 year ago

Pathetic sissy crossdressing cock worship
4:52

Michelle Flowers

183K

82%

2 years ago

Happy Whore Feminization
5:18

Daniela Chanel

3M

86%

1 year ago

Nerdy tranny slut rides cock and gets load shot in her ass pussy.
6:18

SissyMilana

1.3M

92%

2 years ago

Mistress BIG strapon fucking a sissy ass, bitch cums
0:45

Sasha de Sade

1.9M

90%

3 years ago

TS Sex Slave DESTROYED & Creampied by Master's BBC - @sasha_de_sade on all websites
15:05

DreddyHypno

237K

88%

2 years ago

Furry Cock Worship - BrainWash JOI
12:45

Maskedloki9

274K

90%

3 months ago

Goth Femboy gets bred by BBC
2:21

lolacrystals

1.7M

90%

2 years ago

BBC Sissy Slut gets fucked with cage on by Ali Da Reaper
9:13

Michelle Flowers

383

100%

2 months ago

Sissy Crossdresser Double Penetration Blowjob Practice to Sissy Slut Captions
9:18

Traviezisha

13.9K

73%

5 years ago

Sissygasm experience with captions. (Dildo taped up inside asshole)
65:32

Miss Lofn

641K

88%

3 years ago

Positive Sissy Affirmations with Binaural Beats by Miss Lofn
2:14

seriteman

1.8K

83%

4 years ago

Long Leg Tranny in Lingerie
8:48

JulesVerneAnal

1.2M

80%

3 years ago

4 loads of cum dump into my PigHole JulesVerneAnal HUGE GAPE
4:03

margo-apollo

22K

88%

8 months ago

Sissy motivation 5: cum with a dick in your ass (sissy trainer, sissy instruction, sissification)
2:27

seriteman

1.7K

100%

4 years ago

Sissy Femboy just Playing Around
15:15

Mommy Mari NSFW

39.9K

90%

1 month ago

Lovingly Feminized & Face Fucked By Your Best Friend(ෆ˙ᵕ˙ෆ)♡
2:18

lolacrystals

1.2M

91%

2 years ago

QOS Lola Crsytals taking MASSIVE 10 inch BBC and getting creampied!!!
0:18

Bestfemdom

4.4K

83%

2 years ago

A cheap whore was fucked in ass on the chair- Full clip on Onlyfans (link in bio)
6:35

MariahLoveCD

3.3M

91%

2 years ago

Submissive Sissy Crossdresser Slut Gets Man Handled
11:09

FerSuicide

4.4K

93%

4 years ago

Long haired femboy in bodysuit
5:11

Steve Rickz

4.3M

89%

1 year ago

Horny Trans Girl Gets HARD Anal Pounding by Big Cock - Steve Rickz, Jaynethevirgin
6:36

Eva Rex

5.5M

92%

2 years ago

19 year old femboy vs huge knotted bad dragon dildo (while moaning constantly)
0:14

Bestfemdom

6.1K

92%

2 years ago

Mistress fucks the rag hard in the toilet -full clip on my Onlyfans (link in bio)
7:23

CDsindy

123K

91%

4 months ago

Huge dildo fuck machine rough anal session
1:03

CockMongrrr

2.4M

85%

1 year ago

Tied up while these fat cocks broke my mind and asshole

View More

All Comments (13)

Login or Sign Up now to post a comment!

Sissy Annie Grace Williams

Sissy Annie Grace Williams

3 years ago

I wish i would be owned by someone

7

Subsmoothbuns

Subsmoothbuns

2 years ago

Be nice just to have love. Just my opinion.

0

Justhavingfunnnn20

Justhavingfunnnn20

3 years ago

Same

0

Jennyfeminine6969

Jennyfeminine6969

1 year ago

I have been a sissy since my teens, once you've been fucked . Your fate is sealed. Be feminine become who you were always destined to be. Cocks are pleasure and so girly pleasing. So hormone up and start your journey to becoming the sexy hot cum dump your dying to be, you will be so happy.

3

Jessr333

Jessr333

1 year ago

I'm glad my girlfriend caught me cause now she's turning me into her sissy and it's better for me cause she's trans as well

2

Mistysecrets

Mistysecrets

1 year ago

Looking for men to fuck me. Gonna start posting videos.A daddy to pimp my mouth and pussy out would be ideal. But have to start somewhere..

2

Toffee Apples

Toffee Apples

3 years ago

This is so hot 😍💕

1

Britney Cd Slut

Britney Cd Slut

7 months ago

My wife caught me dressed up in my sissy clothes then told me that she was fucking all my friends and black guys for years behind my back and sitting on my face so I could clean her used cum filled pussy it turns her on when I suck cock and fuck my ass with my toys which I love to do now I even love creampies and her cum filled pussy especially when she fucks other guys she has turned me into the perfect sissy cuckold

0

aspiringsissy98

aspiringsissy98

1 year ago

I want my girlfriend to find out the real me and do this to me 😭

0

tentwentyfourfunab

tentwentyfourfunab

1 year ago

You have an amazing ass I wish I could pount you into your bed sheets

0

CdCUMPIG

CdCUMPIG

1 year ago

I need a girlfriend to pimp me out.

0

bicumwhore4all2use

bicumwhore4all2use

2 years ago

Own my ass please!!

0

[[dateAdd]]

[[commentMessage]]

0

© Pornhub.com, 2025

This website is only intended for users over the age of 18.