Porn Porn Transgender • US
  • Live Sex
  • Premium Premium Videos
  • Categories
  • Pornstars
  • Channels
  • photos
GRILL & CHILL DEAL 🔥 Half Price, Full Pleasure

Boy Prison Porn Videos

4260 Results

Free Videos
Short Videos
Premium Videos
Photos
HD
Full HD
4K
VR
Best Videos
By clicking the content you will also see an ad. AD
  • Hot Muscular Futa Poilice and prisoner Public Sex AI Generated
    05:06
    Hot Muscular Futa Poilice and prisoner Public Sex AI Generated
    SecretKum2
    21.6K views
  • Roommate Loses Bet and Gets Locked in Chastity
    07:07
    Roommate Loses Bet and Gets Locked in Chastity
    Cailey Katts
    403.9K views
  • Live
  • Rachel Meets The Rich Sturdy Black Guy With Huge Monsterous Dick in The Prison Cleaning Room
    05:53
    Rachel Meets The Rich Sturdy Black Guy With Huge Monsterous Dick in The Prison Cleaning Room
    Asura
    17K views
  • Sissy Boy3
    33:27
    Sissy Boy3
    2.3M views
  • Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers
    45:14
    Tranny Sherif Gia Darling Declared Miranda's Rules Couple of Taken in Debauchers
    Hot TRANSformations
    5.1K views
  • Older bangs tranny in prison (2019)
    04:57
    Older bangs tranny in prison (2019)
    1.5M 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
    25.4K views
  • sissies in prison
    01:37:44
    sissies in prison
    888.8K 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
    26.1K views
  • Cumming Inside A Femboy
    02:36
    Cumming Inside A Femboy
    Cassie Coyote
    758.7K views
  • The extroverted boy's first day in a maximum security prison.
    09:05
    The extroverted boy's first day in a maximum security prison.
    Bigcockamateur
    13.5K views
  • Long Anal Session for Hurting Emma Tied to the Bench
    01:05:06
    Long Anal Session for Hurting Emma Tied to the Bench
    ActorFab
    522.3K views
  • Brunette tranny punishers take a stud prisoner and fuck him
    07:41
    Brunette tranny punishers take a stud prisoner and fuck him
    Shemale Punishers
    19.4K views
  • Femboy Moans From Getting Railed
    07:10
    Femboy Moans From Getting Railed
    Cailey Katts
    382K views
  • Spreading My Ass Stance to A Prison Inmate to Seduce Him in Bathroom
    05:21
    Spreading My Ass Stance to A Prison Inmate to Seduce Him in Bathroom
    Asura
    6.5K views
  • Bookshop Bois of Prey Episode 2 - Twink Visits Professor At Work
    01:42
    Bookshop Bois of Prey Episode 2 - Twink Visits Professor At Work
    EnbyHalflingBoi
    195.5K views
  • Tranny domina Barbara Cristina fucks her prisoner doggystyle
    06:38
    Tranny domina Barbara Cristina fucks her prisoner doggystyle
    Shemale Punishers
    38.2K views
  • 2032 - the Bwno Future
    15:06
    2032 - the Bwno Future
    ChristineWest120
    261.2K views
  • Three shemales with big tits punish their prisoner until
    07:59
    Three shemales with big tits punish their prisoner until
    Shemale Punishers
    13.7K views
  • The Pizza Boy
    03:38
    The Pizza Boy
    Ftm
    9.5M views
  • Big Booty Fem Sissy Boy Gets Raw BBC
    18:06
    Big Booty Fem Sissy Boy Gets Raw BBC
    DADDYBLACKXXX
    777.1K views
  • Hostel Surprise
    37:09
    Hostel Surprise
    R_logan
    3.8M views
  • Bookshop Bois of Prey Episode 0 - Sexy Bookshop Femboy seduces and gets bred by married man in bookstore
    01:50
    Bookshop Bois of Prey Episode 0 - Sexy Bookshop Femboy seduces and gets bred by married man in bookstore
    EnbyHalflingBoi
    541.7K views
  • girlcock brainwashing - sink even deeper
    17:10
    girlcock brainwashing - sink even deeper
    g gcslave1
    549.2K views
  • Traps and femboys
    11:47
    Traps and femboys
    588.9K views
  • Teaching a Fag his place
    13:47
    Teaching a Fag his place
    Kimberhaven
    1M views
  • Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial
    07:03
    Asian Femboy Tap Forty Punished by Stepbro with Rough Anal & Facial
    Andre Stone
    155.1K views
  • Ruthless TS turns guy into her little bitch
    03:44
    Ruthless TS turns guy into her little bitch
    3.2M views
  • He Couldn't Hide His Desire to Fuck Me Hard with My Chastity Cage
    05:53
    He Couldn't Hide His Desire to Fuck Me Hard with My Chastity Cage
    missangell_
    140.4K views
  • Girly Boys
    50:16
    Girly Boys
    susiecd1
    438.8K 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
    2.1M views
  • sadistic sissy boy Lucy with his bound slave
    03:41
    sadistic sissy boy Lucy with his bound slave
    slave Martin
    53.4K views
  • I Dominate This Bottom Boy so Good
    06:35
    I Dominate This Bottom Boy so Good
    L LadyboyMaria
    241K views
  • Shemale and boy
    03:56
    Shemale and boy
    3.1M views
  • Loser Boyfriend Gets Feminized and Fucked
    08:12
    Loser Boyfriend Gets Feminized and Fucked
    Pure Ts
    546K views
  • Imagine You Are Fucking a Boy!
    06:15
    Imagine You Are Fucking a Boy!
    KinkyHome
    300.8K views
  • Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    08:09
    Hard spanking,severe punishment with heavy belt style tawse. KitsyMe0w restrained gagged and crying.
    Kitsy Meow
    236.5K views
  • Cock Prisoner Aroma Obsession
    04:57
    Cock Prisoner Aroma Obsession
    Natalie Napoli
    4.3K views
  • Diddled
    08:07
    Diddled
    houseofangellxt1
    2.4M views
  • Boi Hunter: Vanniall Cruises Fox and Uses His Holes
    07:34
    Boi Hunter: Vanniall Cruises Fox and Uses His Holes
    Vanniall
    462.9K views
  • Road Trip Day 4
    08:12
    Road Trip Day 4
    TS Seduction by Kink
    170.4K views
  • The Boy Came Straight From Work to Fuck Me.
    08:22
    The Boy Came Straight From Work to Fuck Me.
    Tsdanisantos1
    690.8K views
  • Locked for cock
    10:00
    Locked for cock
    pupott
    272.6K views
  • Anal distractions on a sick penis
    17:34
    Anal distractions on a sick penis
    Schokk077
    42.1K views
  • How to Train Your Sissy Boyfriend
    08:12
    How to Train Your Sissy Boyfriend
    Brat Perversions
    290.4K views
  • Trans Boy Rocki Takes Huge Cock in Tight Ass Til Creampie
    05:05
    Trans Boy Rocki Takes Huge Cock in Tight Ass Til Creampie
    Andre Stone
    356K views
  • rosario prison style
    01:07
    rosario prison style
    d dubdubber
    295.3K views
Next page
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. ...
  8. 41
  9. ...
  10. 80
80
Categories
American
4K Porn
HD Videos
VR Porn
The Handy
Shemale Fucks Guy
Big Cock
Black
Shemale Fucks Shemale
Amateur
Shemale Fucks Girl
Sissy
Ladyboy
Guy Fucks Shemale
Blowjob
Compilation
Big Black Cock
Cum In Mouth
Big Ass
Cumshot
Mature
Bareback
Creampie
Homemade
Masturbation
Anal
Teen
Domination
Asian
Solo
BBW
Brazilian
Vintage
Transgender
Young
Big Tits
Mexican
Interracial
Cartoon
Japanese
Small Cock
Lingerie
Threesome
Gangbang
Thai
Trans Woman
Trap
Colombian
BDSM
Public
Pretty
MILF
Couple
Petite
Anal Masturbation
Rough Sex
Dildo
Cuckold
Outdoor
Stockings
Small Tits
Babysitter
POV
Indian
Handjob
Group Sex
Trans Man
Hentai
Fetish
English
Futanari
Ass Licking
Hardcore
Massage
Bondage
Chinese
Nude
Pissing
SFW
All recommendations
Monetize your content
Become a creator
xHamster
  • About us
  • Blog
  • Creator's Blog
  • Advertising
  • xHamster Awards 2025
  • SEO Specialist Job
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
Earn money with us
  • Camgirls Wanted
  • Creator Contest
  • Сontent Creators Program
© 2026 xHamster - Free porn videos.
Desktop Version
U.S.C. 2257 Notice
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