PornPorn Transgender • US
    Sign up for free
    Videos
    • Best Videos
    • Short Videos
    • Watch History
    • American
    • Amateur
    • Shemale Fucks Guy
    • Shemale Fucks Girl
    • Big Cock
    • All categories
    Live Sex
    Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • All categories
    Pornstars
    • Pornstars
    • By Countries
    • xHamster Creators
    Creators
    • Top Creators
    • Top Creator Videos
    • Awards 2025
    • All xHamster Creators
    • By Countries
    • Become a Creator
    Channels
    Photos
    • Ladyboy
    • Tranny
    • Big Cock
    • Thai
    • Blowjob
    • All categories
    Faphouse
    Premium Videos
    -60%
    Dating
    Subscriptions
    • Upload
    +14 MONTHS FREE 😱🎉🔥 Faphouse Holiday Sale
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Big Cock
    • Black
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Cum In Mouth
    • Big Black Cock
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Homemade
    • Mature
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Pretty Prison Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Tomboy Lesbians Futa Sexfight - Wrestling Prison Tattoo Girls Having Horny Fun with CUM Play
    09:15
    Tomboy Lesbians Futa Sexfight - Wrestling Prison Tattoo Girls Having Horny Fun with CUM Play
    Futanari XXX
    340.9K views
    Prison Futa Transformation - 18 Years Old Matty Mila Summons Demon and Turns Into Insatiable Shemale
    07:06
    Prison Futa Transformation - 18 Years Old Matty Mila Summons Demon and Turns Into Insatiable Shemale
    Futanari XXX
    245.3K views
    Prison Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER
    01:18
    Prison Guard Fucks Blonde Inmate After FUTA Transformation Ends With Huge Facial TRAILER
    Futanari XXX
    1.8M views
    Hot anal trans sex prison house fantasies
    24:32
    Hot anal trans sex prison house fantasies
    Shemale Strokers
    348.1K views
    Chicks with Dicks - Sexy Latina Turns Into Prison Cum Slut for Redhead Sata Jones Futa Creampie
    01:35
    Chicks with Dicks - Sexy Latina Turns Into Prison Cum Slut for Redhead Sata Jones Futa Creampie
    Futanari XXX
    180.3K views
    Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl
    07:06
    Agatha Vega Tg Prison Fuck - Horny Shemale Detective Gets Blowjob from Latina Girl
    Futanari XXX
    74.5K views
    Paying My First Debt in Jail - Prison Of Sissy
    08:09
    Paying My First Debt in Jail - Prison Of Sissy
    Asura
    25.4K views
    Shemale Officer Fucks Hot Pearl In Prison With A Big Dick - Rough Sex Futa Cumshots TRAILER
    01:35
    Shemale Officer Fucks Hot Pearl In Prison With A Big Dick - Rough Sex Futa Cumshots TRAILER
    Futanari XXX
    217.7K views
    You Are a Prisoner to Your Sissy Porn
    11:48
    You Are a Prisoner to Your Sissy Porn
    Natalie Napoli
    13.2K views
    Nancy In Prison
    18:15
    Nancy In Prison
    Nancy Rose
    11K views
    Captive life, peeing in prison
    06:20
    Captive life, peeing in prison
    alina1235698
    30.5K views
    TSVirtualLovers - Prisoner Kendall Penny in VR
    09:25
    TSVirtualLovers - Prisoner Kendall Penny in VR
    TS Virtual Lovers
    36.5K views
    Prisoner Put His Dick in the Transvestite Police Officer
    06:47
    Prisoner Put His Dick in the Transvestite Police Officer
    Avantajadas
    20.1K views
    Hard Futa Cock Slut Fucks Her Elf Prisoner And Creampies Deep In Her Tight Pussy
    10:18
    Hard Futa Cock Slut Fucks Her Elf Prisoner And Creampies Deep In Her Tight Pussy
    GoodNewsMedia
    6.5K views
    Stunning tranny Bia Gaucha is taken prisoner and gets fucked
    06:52
    Stunning tranny Bia Gaucha is taken prisoner and gets fucked
    Tranny Edge
    3K views
    Super Sexy Trans Girl in Cuffs Gets Fucked Hard by BBC in the Prison
    05:20
    Super Sexy Trans Girl in Cuffs Gets Fucked Hard by BBC in the Prison
    martha 3d group
    4.4K views
    Police Shemale Gets Hard Anal Fuck From Her Prisoner on the Chair
    08:12
    Police Shemale Gets Hard Anal Fuck From Her Prisoner on the Chair
    Shemale Idols
    3.3K views
    Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89
    00:31
    Extreme Anal Cavity Search - Dungeon Under Heathrow Airport - Mule Gets Found Out by valentinarosa89
    Jasmine_dlight
    5.1K views
    Super sexy trans girl in cuffs gets fucked hard by BBC in the prison
    04:34
    Super sexy trans girl in cuffs gets fucked hard by BBC in the prison
    3dxpassion
    9.7K views
    Cock Hungry TS Officer Drika Lima Lets The Prisoner Fuck Her Ass
    15:10
    Cock Hungry TS Officer Drika Lima Lets The Prisoner Fuck Her Ass
    Dream Tranny
    6K views
    TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting  Fucked With Hot Prisoner Kimberlee
    35:45
    TRANS ANGELS - Officer Chanel Santini Cannot Resist Getting Fucked With Hot Prisoner Kimberlee
    Trans Angels
    1.3M views

    Relevant Short videos

    You Are a Prisoner to Your Sissy Porn
    You Are a Prisoner to Your Sissy Porn
    Natalie Napoli
    1.4K views
    Stunning moment from "Straight boy disguises himself as hot femboy in prison. Prison of Sissy."
    Stunning moment from "Straight boy disguises himself as hot femboy in prison. Prison of Sissy."
    Bigcockamateur
    448 views
    Thrilling moment from "Super sexy trans girl in cuffs gets fucked hard by BBC in the prison"
    Thrilling moment from "Super sexy trans girl in cuffs gets fucked hard by BBC in the prison"
    3dxpassion
    280 views
    Sexy Latina Agatha Vega Grows 3d Hermaphrodite Futa Cock - Transgender Prison Fuck Creampie Trailer
    Sexy Latina Agatha Vega Grows 3d Hermaphrodite Futa Cock - Transgender Prison Fuck Creampie Trailer
    Futanari XXX
    3.3K views
    Futa Prison Witch - 18 Year Old Matty Mila Summons Hentai Sex Demon And Turns Into Tg Shemale
    Futa Prison Witch - 18 Year Old Matty Mila Summons Hentai Sex Demon And Turns Into Tg Shemale
    Futanari XXX
    1.3K views
    Prison Thug Jacks off Huge Big Black Cock
    Prison Thug Jacks off Huge Big Black Cock
    SweetDWillie456
    819 views
    Older bangs tranny in prison (2019)
    04:57
    Older bangs tranny in prison (2019)
    1.3M views
    sissies in prison
    01:37:44
    sissies in prison
    707.1K views
    Prison Guard Ts fucks another prisoner tranny 02
    07:00
    Prison Guard Ts fucks another prisoner tranny 02
    877.3K views
    rosario prison style
    01:07
    rosario prison style
    233.8K views
    TSVirtualLovers - Sex with the Prisoner in POV
    09:24
    TSVirtualLovers - Sex with the Prisoner in POV
    TS Virtual Lovers
    168K views
    intense prison style
    00:28
    intense prison style
    1M views
    Prison of Sissy 3 the Pr Manager Fucked
    11:10
    Prison of Sissy 3 the Pr Manager Fucked
    Johannesgaming
    18.7K views
    My First Day in Prison: Bathroom Experience
    07:30
    My First Day in Prison: Bathroom Experience
    Asura
    113.1K views
    Nathalia Fontes Is Dominated and Punished in Abandoned Prison
    13:00
    Nathalia Fontes Is Dominated and Punished in Abandoned Prison
    Nathalia Fontes
    96.2K views
    Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give
    25:08
    Prison of Sissy 2 Adam Used the Glory Hole Not to Get a BJ but to Give
    Johannesgaming
    21.1K views
    Prison of Sissy 4 I Love to Suck Cock
    14:54
    Prison of Sissy 4 I Love to Suck Cock
    Johannesgaming
    9.9K views
    Travtchoin fertilize 5 times by a former prisoner from Lyon
    03:04
    Travtchoin fertilize 5 times by a former prisoner from Lyon
    182.5K views
    Female alien in a prison gets fucked hard by a hot dickgirl
    27:56
    Female alien in a prison gets fucked hard by a hot dickgirl
    martha 3d group
    40.6K views
    Straight boy disguises himself as hot femboy in prison. Prison of Sissy.
    09:39
    Straight boy disguises himself as hot femboy in prison. Prison of Sissy.
    Bigcockamateur
    9.9K views
    Prison of Sissy - Crime Is Not the Way to Go.
    31:05
    Prison of Sissy - Crime Is Not the Way to Go.
    Johannesgaming
    15.6K views
    julie bond fucks girl in prison
    11:19
    julie bond fucks girl in prison
    113.8K views
    Tranny domina Barbara Cristina fucks her prisoner doggystyle
    06:38
    Tranny domina Barbara Cristina fucks her prisoner doggystyle
    Shemale Punishers
    24.8K views
    A Demand for The Cure - Prison of Sissy
    09:07
    A Demand for The Cure - Prison of Sissy
    Asura
    22.2K views
    Hot Trans Prostitute Fucks A Prisoner
    13:02
    Hot Trans Prostitute Fucks A Prisoner
    Devils tgirls
    58.2K views
    Transsexual Prison Guard Fucks An Inmate
    28:25
    Transsexual Prison Guard Fucks An Inmate
    Wonder Shemale
    71K views
    Big cock Jesse gets a blowjob from her prisoner before
    07:20
    Big cock Jesse gets a blowjob from her prisoner before
    Shemale Punishers
    15.9K views
    Policewoman with a huge cock turns her prisoner into a dick slut
    08:28
    Policewoman with a huge cock turns her prisoner into a dick slut
    DotadaSP
    221.2K views
    PORNSTAR TS BIG BOOTY BIANCA FUCKS ESCAPED PRISONER !
    01:44
    PORNSTAR TS BIG BOOTY BIANCA FUCKS ESCAPED PRISONER !
    Ts Big Booty Bianca
    90.3K views
    Prison of Sissy - Crime Is Not the Way to Go
    31:05
    Prison of Sissy - Crime Is Not the Way to Go
    Johannesgaming
    19K views
    Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell
    07:35
    Dickgirl Ladyboy Is Fucking Girl Standing in Her Prison Cell
    Wraith931
    9.9K views
    Prison of Sissy: The First Friend
    06:43
    Prison of Sissy: The First Friend
    Asura
    33.2K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    xHamster

    • Press
    • Blog
    • Creator's Blog
    • Advertising
    • xHamster Awards 2025

    Help

    • FAQ
    • Contact us
    • Content Removal
    • Improve xHamster

    Legal

    • Terms of use
    • Privacy policy
    • Cookies policy
    • DMCA/Copyright
    • Parental Controls
    • EU DSA
    • Trust and Safety

    Start making money with us

    • Camgirls Wanted
    • Creator Contest
    • Сontent Creators Program
    Monetize your content
    Become a creator
    © 2007 - 2026, xHamster.com
    Mobile Version
    18 U.S.C. 2257 Record-Keeping Requirements Compliance Statement
    RTA Restricted To AdultsRTA Restricted To Adults
    xHamster is adults only website!

    The content available on xHamster may contain pornographic materials.

    xHamster is strictly limited to those over 18 or of legal age in your jurisdiction, whichever is greater.

    One of our core goals is to help parents restrict access to xHamster for minors, so we have ensured that xHamster is, and remains, fully compliant with the RTA (Restricted to Adults) code. This means that all access to the site can be blocked by simple parental control tools. It is important that responsible parents and guardians take the necessary steps to prevent minors from accessing unsuitable content online, especially age-restricted content.

    Anyone with a minor in their household or under their supervision should implement basic parental control protections, including computer hardware and device settings, software installation, or ISP filtering services, to block your minors from accessing inappropriate content.

    To enter xHamster you must be 18 or older
    how to protect your minors
    RTA Restricted To AdultsRTA Restricted To Adults