Sissy (190,430)

Sissy Gets Butt Fucked!

68% HD 1:01 / 10:34

Sissy Gets Butt Fucked!

FapHouse 10 months ago

SISSY TRAINING: YOU WANT COCK! Bi Encouragement POV for Curious Sissies

SISSY TRAINING: YOU WANT COCK! Bi Encouragement POV for Curious Sissies

LoyalFans 1 week ago

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

72% HD 0:08 / 0:40

BBC Vs Clitty! Adreena Winters Mocks This Sissy Into Cock Sucking Submission

FapHouse 8 months ago

Your Mind Belongs To BBC (Sissy Trainer)

Your Mind Belongs To BBC (Sissy Trainer)

XHamster 1 month ago

Turning You Into My Sissy Slut

Turning You Into My Sissy Slut

XHamster 1 month ago

Cucks duties before and after date

71% HD 1:01 / 27:35

Cucks duties before and after date

FapHouse 3 years ago

sucking cock, thin white sissy, femboi, feminine, video created by AI

sucking cock, thin white sissy, femboi, feminine, video created by AI

Seduced 1 year ago

Borrow My Sissy Boyfriend

66% 0:39 / 25:50

Borrow My Sissy Boyfriend

FapHouse 7 months ago

Fucked him and made him cum inside her

63% HD 1:01 / 29:54

Fucked him and made him cum inside her

FapHouse 5 years ago

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

77% HD 1:01 / 5:45

Exposing My Sissy Best Friend- Goddess Rosie Reed Exposes Her Sissy Best Friend- Ebony Femdom Sissy Training

FapHouse 3 months ago

Introduction to Flr

63% HD 1:01 / 17:06

Introduction to Flr

FapHouse 1 year ago

Amazing Handjob for Sissy and Amazing Funny Cumming

57% 0:39 / 12:11

Amazing Handjob for Sissy and Amazing Funny Cumming

FapHouse 2 years ago

Bi Domination: Not Entirely Straight

52% HD 1:01 / 21:14

Bi Domination: Not Entirely Straight

FapHouse 4 months ago

Sissy Husband Becomes Cocksucking Cuckold

57% HD 0:10 / 16:13

Sissy Husband Becomes Cocksucking Cuckold

LoyalFans 5 months ago

Sissy Training - Teaching My Friend How to Give a Blowjob

65% HD 1:01 / 29:53

Sissy Training - Teaching My Friend How to Give a Blowjob

FapHouse 2 years ago

The Bi Sissy Slut From Husband to Willing Slut!

55% HD 0:39 / 36:01

The Bi Sissy Slut From Husband to Willing Slut!

FapHouse 7 months ago

the sissy with the big ass gets fucked in the ass by big cocks.

63% HD 0:54 / 15:01

the sissy with the big ass gets fucked in the ass by big cocks.

AnalVids 1 month ago

My Sissy Makes Show for Femdom

My Sissy Makes Show for Femdom

FapHouse 2 weeks ago

Sissy Clit Versus Big Black Cock

HD 0:39 / 17:12

Sissy Clit Versus Big Black Cock

FapHouse 1 day ago

2 Hole Maid

58% HD 0:39 / 15:34

FapHouse 2 months ago

Stepbro Panty Humiliation

60% HD 0:39 / 25:52

Stepbro Panty Humiliation

FapHouse 10 months ago

Sex Change Clinic

49% HD 0:25 / 44:57

Sex Change Clinic

IWantClips 1 year ago

Very taboo bisexual threesome JOI

48% HD 1:01 / 18:09

Very taboo bisexual threesome JOI

FapHouse 3 years ago

Mistress Blondy visits me and fucks me again

51% HD 0:10 / 13:14

Mistress Blondy visits me and fucks me again

LoyalFans 3 years ago

Two Sex Slaves Used What They're There for

HD 0:39 / 10:55

Two Sex Slaves Used What They're There for

FapHouse 1 week ago

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

51% HD 1:01 / 13:10

Real Life Couple! Shared Sissy - Pegging the Sissy Hubby

FapHouse 9 months ago

Milking the Sissy

55% HD 0:39 / 11:14

Milking the Sissy

FapHouse 5 months ago

Sissy Sex Slave

62% HD 0:30 / 1:21:00

Sissy Sex Slave

AEBN 17 years ago

Hospitality Whores (full scene 4k)

52% 4K 0:30 / 42:01

Hospitality Whores (full scene 4k)

IWantClips 2 years ago

Maid to Suck

57% HD 0:07 / 0:40

FapHouse 1 month ago

Chaste sissy

59% HD 1:01 / 25:28

FapHouse 6 years ago

Sissy Chastity Cuckold Humiliation, Hotwife Locks Her Caged Sissy Dildo Dummy

HD 0:39 / 19:20

Sissy Chastity Cuckold Humiliation, Hotwife Locks Her Caged Sissy Dildo Dummy

FapHouse 6 days ago

Sissy Sex Slave

49% HD 0:30 / 1:21:00

Sissy Sex Slave

AEBN 17 years ago

Anal Loving stepmom Sissy Neri loves getting fucked in the ass by her horny stepson

55% 4K 1:14 / 31:50

Anal Loving stepmom Sissy Neri loves getting fucked in the ass by her horny stepson

Mature.nl 3 years ago

teen sissy begs for some cock

46% HD 0:30 / 28:38

teen sissy begs for some cock

AnalVids 4 weeks ago

Everything that happened in 2022

50% HD 0:10 / 2:33:28

Everything that happened in 2022

LoyalFans 3 years ago

Teaching My Cuckold - SNOWBALLING & HUMILIATION

63% 1:01 / 20:17

Teaching My Cuckold - SNOWBALLING & HUMILIATION

FapHouse 3 years ago

Spanked Sissy - Part 1 Miss Jessica Wood & Mistress Ava Starts off Their Naught Sissy Punishment with Hand Spanking

66% HD 1:01 / 8:24

Spanked Sissy - Part 1 Miss Jessica Wood & Mistress Ava Starts off Their Naught Sissy Punishment with Hand Spanking

FapHouse 1 month ago

I Fuck Her Ass Like a Bitch and Make Her Cum on Her Face

56% HD 1:01 / 9:40

I Fuck Her Ass Like a Bitch and Make Her Cum on Her Face

FapHouse 1 year ago

Man Enough to Be My Boytoy?

Man Enough to Be My Boytoy?

FapHouse 1 week ago

Making of Sissy Sasha

45% HD 0:25 / 33:34

Making of Sissy Sasha

IWantClips 2 months ago

Sissy Anal Exam

64% HD 1:01 / 17:14

Sissy Anal Exam

FapHouse 10 months ago

Sissy College Lesson 2 Chastity

55% HD 0:08 / 0:40

Sissy College Lesson 2 Chastity

FapHouse 10 months ago

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

64% HD 1:01 / 11:28

Shivering and Leaking of Lust and Frustration! - Chastity, Sissy Training, Pantyhose and Orgasm Denial with Miss Adrastea

FapHouse 2 months ago

Get her ready for the Cage

HD 0:39 / 11:40

Get her ready for the Cage

FapHouse 5 years ago

SissyJoyce Roomtour and Sissygasm

65% HD 0:10 / 11:17

SissyJoyce Roomtour and Sissygasm

LoyalFans 3 years ago

Sissy & cuckold training

52% HD 1:01 / 11:51

Sissy & cuckold training

FapHouse 5 years ago

Two Sex Slaves Used What They're There for

HD 1:01 / 10:55

Two Sex Slaves Used What They're There for

FapHouse 1 week ago

Femboy and Vilu Vidish Compilation

67% HD 0:39 / 1:05:58

Femboy and Vilu Vidish Compilation

FapHouse 2 months ago

Baby in paradise part 1

63% HD 0:39 / 9:01

Baby in paradise part 1

FapHouse 4 years ago

Sissy Clitty Affirmations

51% HD 1:01 / 9:15

Sissy Clitty Affirmations

FapHouse 5 months ago

Group Bi Training with My Three Girlfriends

Group Bi Training with My Three Girlfriends

XHamster 2 months ago

Mistress Fiona likes to play with me

60% HD 0:10 / 20:59

Mistress Fiona likes to play with me

LoyalFans 3 years ago

Spanked Sissy - Part 3 - Miss Jessica Wood & Mistress Ava Finally Get Their Canes on the Naughty Sissy with Classic Caning

62% HD 1:01 / 10:01

Spanked Sissy - Part 3 - Miss Jessica Wood & Mistress Ava Finally Get Their Canes on the Naughty Sissy with Classic Caning

FapHouse 3 weeks ago

Complete Shrink & Hole Discipline Ritual - Full Femdom POV Session

Complete Shrink & Hole Discipline Ritual - Full Femdom POV Session

XHamster 5 months ago

Out of the Cage - Into Ass-punishment

65% HD 1:01 / 9:21

Out of the Cage - Into Ass-punishment

FapHouse 1 month ago

Sissy Training in Chastity

57% HD 0:39 / 9:54

Sissy Training in Chastity

FapHouse 1 year ago

Maddie's Dick Ratings

HD 1:01 / 10:07

Maddie's Dick Ratings

FapHouse 6 days ago

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

65% HD 1:01 / 47:50

Sissy Secretary: Feminization, Pegging, Fisting, & More Full-length (1080p)

FapHouse 6 days ago

Sissy’s 7am Grindrr Hookup

64% HD 0:10 / 10:06

Sissy’s 7am Grindrr Hookup

LoyalFans 7 months ago

Sissy Maid Caught in My 12cm Heels

Sissy Maid Caught in My 12cm Heels

StiefMutter 1 week ago

Ria Bentley Loves a Big Strong Black Man

64% HD 0:10 / 25:46

Ria Bentley Loves a Big Strong Black Man

LoyalFans 4 months ago

A hyperfeminine sissy bride having, video created by AI

A hyperfeminine sissy bride having, video created by AI

Seduced 1 year ago

Hot Prostate Massage with an Epic Cumshot

75% HD 1:01 / 17:54

Hot Prostate Massage with an Epic Cumshot

FapHouse 11 months ago

she squats and masturbates until she cums all over his sissy face

she squats and masturbates until she cums all over his sissy face

PissVids 4 days ago

Who

HD 0:25 / 10:50

IWantClips 2 months ago

Lift the skirt, suck that cock, milk his cum!

64% 1:01 / 14:07

Lift the skirt, suck that cock, milk his cum!

FapHouse 3 years ago

Sexy tight waist blonde, trap sissy, c-cup, video created by AI

Sexy tight waist blonde, trap sissy, c-cup, video created by AI

Seduced 6 months ago

Sissy Mel gets the works

60% HD 0:10 / 12:00

Sissy Mel gets the works

LoyalFans 1 month ago

Sissy Slut Transformation - Sph

HD 1:01 / 18:03

Sissy Slut Transformation - Sph

FapHouse 3 weeks ago

Tonight You Suck Cock for Me - 1080p HD

63% HD 1:01 / 6:03

Tonight You Suck Cock for Me - 1080p HD

FapHouse 2 months ago

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

HD 1:01 / 17:26

Sissy Gamer Gurl: Feminization & Throat Fucking Part 1 of 3 (1080p)

FapHouse 5 days ago

Sissy Dressup Party With Sasha De Sade

62% HD 0:10 / 25:05

Sissy Dressup Party With Sasha De Sade

LoyalFans 11 months ago

Electra Joness Party on Apr 13, 2026 - Part 3

52% 4K 2:00 / 1:00:15

Electra Joness Party on Apr 13, 2026 - Part 3

Flirt4Free 4 months ago

Purity Chastity Cage

60% 0:39 / 15:53

Purity Chastity Cage

FapHouse 3 weeks ago

modern gothic anime punk fetish girls are into feminization!

57% HD 0:30 / 19:47

modern gothic anime punk fetish girls are into feminization!

PornBox 6 days ago

Marriage Bitch Gets Lesbian Fucked, Sissy Cuckold Has to Watch

71% HD 1:01 / 8:56

Marriage Bitch Gets Lesbian Fucked, Sissy Cuckold Has to Watch

FapHouse 1 year ago

SISSY DRESS UP

65% 0:30 / 9:04

Clips4sale 1 year ago

Dressed up in Gloss to Suck My Cock

Dressed up in Gloss to Suck My Cock

XHamster 3 days ago

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

Femdom Pegging Sissy Training, Strap on Anal for the New Recruit

XHamster 5 days ago

Sissy CumShots Compilation

Sissy CumShots Compilation

SortPorn 4 years ago

4 Benefits of Being a Sissy

48% HD 0:39 / 5:57

4 Benefits of Being a Sissy

FapHouse 3 months ago

Sissy and I in the Bathroom

Sissy and I in the Bathroom

FapHouse 1 week ago

Sissy Academy Part 7 - Sissy Come and Sip

59% HD 0:39 / 5:31

Sissy Academy Part 7 - Sissy Come and Sip

FapHouse 2 months ago

Sissy Maid Slave

48% HD 0:30 / 1:02:00

Sissy Maid Slave

AEBN 17 years ago

Rubber Sissy: Anal & Oral Training

55% HD 1:01 / 13:53

Rubber Sissy: Anal & Oral Training

FapHouse 3 weeks ago

Anal Sissy Slut in Chastity

57% HD 0:10 / 15:25

Anal Sissy Slut in Chastity

LoyalFans 5 months ago

Goddess Sabrina - 2 of 6

60% HD 1:01 / 10:17

Goddess Sabrina - 2 of 6

FapHouse 1 year ago

Step-mommy's Forever 2

64% 1:01 / 34:34

Step-mommy's Forever 2

FapHouse 2 weeks ago

femboi, short blonde hair, pink latex sissy, video created by AI

femboi, short blonde hair, pink latex sissy, video created by AI

Seduced 1 year ago

Sissification and Humiliation

72% HD 1:01 / 50:07

Sissification and Humiliation

FapHouse 4 weeks ago

Our Sissy Is Sucking Our Cocks

HD 0:39 / 16:55

Our Sissy Is Sucking Our Cocks

FapHouse 6 days ago

Black or Pink boots while I fuck myself?

51% HD 0:10 / 13:55

Black or Pink boots while I fuck myself?

LoyalFans 3 years ago

Part 1 Locked and Conditioned for This Sissy After 6 Months with No News - Maitresse Julia

54% HD 1:01 / 15:43

Part 1 Locked and Conditioned for This Sissy After 6 Months with No News - Maitresse Julia

FapHouse 2 years ago

Sissi Pussy Whip 37232

50% HD 0:39 / 4:10

Sissi Pussy Whip 37232

FapHouse 5 months ago

training zero femdom sissy slave shock collar lapdance humiliation

60% HD 1:33 / 9:15

training zero femdom sissy slave shock collar lapdance humiliation

PornBox 1 month ago

Your Ass Is Ours!

HD 0:39 / 15:02

Your Ass Is Ours!

FapHouse 2 weeks ago

Sissy Heel & Foot Worship

Sissy Heel & Foot Worship

LoyalFans 2 weeks ago

Electra Joness Party on Aug 10, 2026 - Part 3

69% HD 2:00 / 1:36:56

Electra Joness Party on Aug 10, 2026 - Part 3

Camster 4 weeks ago

LILY DUPONT : SISSY GO TO SCHOOL AND LEARN TO DRINK CUM

HD 0:10 / 16:58

LILY DUPONT : SISSY GO TO SCHOOL AND LEARN TO DRINK CUM

LoyalFans 1 month ago

Chaste Sissy Slut One Bar Prison Tease

68% HD 0:10 / 13:25

Chaste Sissy Slut One Bar Prison Tease

LoyalFans 3 years ago

Asian Girl Pegs her Sissy BF [8K Remastered]

56% VR 1:14 / 18:49

Asian Girl Pegs her Sissy BF [8K Remastered]

VRPorn 11 months ago

Sissy Gets to Cum on Two Faces at Once

Sissy Gets to Cum on Two Faces at Once

XHamster 1 month ago

Date mit dem Alpha – Sissy darf helfen

Date mit dem Alpha – Sissy darf helfen

LoyalFans 6 days ago

Turning You Into A Cock Sucking Sissy

HD 0:10 / 18:40

Turning You Into A Cock Sucking Sissy

LoyalFans 1 year ago

Sissy Maid Caught in My 12cm Heels

Sissy Maid Caught in My 12cm Heels

Itsrealamateurs 1 week ago

Permanent Sissy Life (4K)

4K 0:10 / 12:20

Permanent Sissy Life (4K)

LoyalFans 3 weeks ago

Stepson Straps Himself on in Cowgirl Position While Riding a Curvy MILF

Stepson Straps Himself on in Cowgirl Position While Riding a Curvy MILF

XHamster 1 week ago

Femdom Humiliation - Oops, I've Made You Gay!

44% HD 1:01 / 18:20

Femdom Humiliation - Oops, I've Made You Gay!

FapHouse 4 months ago

Nylon Foot Licked

Nylon Foot Licked

FapHouse 2 days ago

Erotic Humiliation

48% HD 1:01 / 51:56

Erotic Humiliation

FapHouse 9 months ago

Sissy Husband Jerks Off While Riding On Monkey Rocker

Sissy Husband Jerks Off While Riding On Monkey Rocker

Eporner 6 years ago

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

Mistress's Command: Edge & Slap Control Game (Male Submission) Clip 2

XHamster 9 months ago

Punished Sissy Husband Part 1 of 4: BDSM Bimbo Humiliated & Whipped in Bondage with Stellina Obscura

HD 0:25 / 13:45

Punished Sissy Husband Part 1 of 4: BDSM Bimbo Humiliated & Whipped in Bondage with Stellina Obscura

Clips4sale 1 week ago

Prissy Sissy Maid Training Stage 5

HD 0:10 / 12:43

Prissy Sissy Maid Training Stage 5

LoyalFans 2 weeks ago

Lock it Up for Life! Sissy Slave PERMA-CHASTITY & Slave TATTOOS! Femdom Feminization Training by Goddess Kyaa Chimera

HD 0:10 / 10:39

Lock it Up for Life! Sissy Slave PERMA-CHASTITY & Slave TATTOOS! Femdom Feminization Training by Goddess Kyaa Chimera

LoyalFans 3 days ago

Sissy on Sissy Sex and Stimulation

48% HD 0:10 / 8:13

Sissy on Sissy Sex and Stimulation

LoyalFans 4 months ago

morning wild sex, he like to eat own sperm creampie eating after sex

morning wild sex, he like to eat own sperm creampie eating after sex

PornBox 2 days ago

A SISSY MAID OFFERING

60% HD 0:10 / 15:04

A SISSY MAID OFFERING

LoyalFans 3 years ago

Little Sissy

VR 1:12 / 15:04

VRPorn 6 months ago

1 2 3 4 5

190,430 results found

Related categories

Transvestite Crossdressing Femboy 18+ Feminization Ladyboy Trans Domination Strap-On Trans Chastity Tgirl Trans Femboy BBC Instructions Trans Fucks Trans Trans Fucks Guy Hermaphrodite Slave Trans Big Cock Trans Fucks Girl Chastity Cage Edging

Narrow your search

femdom sissy sissy training sissy caption story sissy caption sissy femdom sissy joi sissy maid sissy cuckold sissy pegging sissy bbc sissy slave pegging sissy sissy chastity sissy bondage sissy husband bbc sissy sissy humiliation sissy neri sissy mature sissy compilation

Categories Pornstars

Parents

Shortporn.com uses the “Restricted To Adults” (RTA) website label to better enable parental filtering. Protect your children from adult content and block access to this site by using parental controls.

© 2026 Shortporn.com. All rights reserved.

© 2026 Shortporn.com. All rights reserved.