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

    Sissy Boy And Old Man Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Sissy
    Old
    Boy
    Man
    Sissy Old Man
    Sissy Boy
    Old Man
    Boy Sissy
    Sissy Man
    Sissy Crossdresser
    Sissy Training
    Lady Boy
    Bbc Sissy
    Sissy Feminization
    Teen Sissy Boy
    Sissy Husband
    Sissy Chastity
    Sissy Compilation
    Sissy Fucked
    Trans Man
    Best Videos
    By clicking the content you will also see an ad. AD
    Grandfather fuck hard
    01:15
    Grandfather fuck hard
    626.5K views
    Sissy boy.... nice old dick to suck on..
    06:04
    Sissy boy.... nice old dick to suck on..
    65K views
    my friend s grandfather
    23:25
    my friend s grandfather
    178.1K views
    Sissy boy fucked by older step daddy bear RAW FOOTAGE
    02:15
    Sissy boy fucked by older step daddy bear RAW FOOTAGE
    Viper Fierce
    36.6K views
    Will you play with granny tranny Vick's bush?
    07:07
    Will you play with granny tranny Vick's bush?
    Victoria Lecherri
    230.9K views
    30yr Old With Bubble Butt – Small Waist Club
    03:23
    30yr Old With Bubble Butt – Small Waist Club
    Karma Rainbow Smith D
    130K views
    Blonde sissy has fun with a Grandpa
    04:01
    Blonde sissy has fun with a Grandpa
    Crossdressing Amateurs
    339.8K views
    Indian desi bhabhi and hot boy sexy video.
    07:54
    Indian desi bhabhi and hot boy sexy video.
    Permi_pooja
    2M views
    Redhead tranny fucking with a old man
    15:58
    Redhead tranny fucking with a old man
    995.3K views
    20-year-old trans woman, rich, anal sex
    05:09
    20-year-old trans woman, rich, anal sex
    Sexytransjordana25
    5.7K views
    Cross Dressing Student and Tutor Playing with Each Other
    08:12
    Cross Dressing Student and Tutor Playing with Each Other
    Crossdressing Amateurs
    295.7K views
    19 Years Old Cute Sissy Jude's Serves Her First Day in Gloryhole Handjob
    05:32
    19 Years Old Cute Sissy Jude's Serves Her First Day in Gloryhole Handjob
    Asura
    6.6K views
    Daddy's Good Girl!
    08:12
    Daddy's Good Girl!
    Pure Ts
    901.5K views
    BBC Tranny TS fucked a RAW white boy like a bitch - wicked whims
    14:56
    BBC Tranny TS fucked a RAW white boy like a bitch - wicked whims
    SimsLust
    78.8K views
    My stepmom is a tranny
    16:46
    My stepmom is a tranny
    Combat zone transsexual barebacking
    1.1M views
    My Busty Fit tranny Boss owned my mouth - WickedWhims
    15:28
    My Busty Fit tranny Boss owned my mouth - WickedWhims
    SimsLust
    125.6K views
    My lingerie night with my 2 hot young men!
    12:32
    My lingerie night with my 2 hot young men!
    Victoria Lecherri
    76.8K views
    POV delicious blowjob from my 20-year-old trans neighbor
    05:10
    POV delicious blowjob from my 20-year-old trans neighbor
    Sexytransjordana25
    3.2K views
    I came from college and daddy was waiting for me
    06:57
    I came from college and daddy was waiting for me
    Sebnem
    397.4K views
    Sexy Shemale fucks herself with a Huge Vibrator Dildo before taking a Shower making Her Anus loose
    05:28
    Sexy Shemale fucks herself with a Huge Vibrator Dildo before taking a Shower making Her Anus loose
    CaliFauna
    108.3K views
    Amateur trany hard fucked -He Made My Hole Huge -
    31:55
    Amateur trany hard fucked -He Made My Hole Huge -
    1.2M views
    Tranny Fisting and Prolapsing her Asshole
    00:40
    Tranny Fisting and Prolapsing her Asshole
    CaliFauna
    25.1K views
    Married Mature Daddy Doggy Fucks Trans Girl Bareback
    07:22
    Married Mature Daddy Doggy Fucks Trans Girl Bareback
    KittyKaash
    303.5K views
    Tranny fingering her Ass before putting her Dick inside her own Asshole  Self-fuck
    02:25
    Tranny fingering her Ass before putting her Dick inside her own Asshole Self-fuck
    CaliFauna
    12.4K views
    Shemale fucks grandpa bareback on cam
    11:00
    Shemale fucks grandpa bareback on cam
    159.5K views
    I want you inside of me so bad
    01:01
    I want you inside of me so bad
    CaliFauna
    5.6K views
    Ts Fuck Mature Man
    12:24
    Ts Fuck Mature Man
    1M views
    Tranny stretching her little Tight Asshole with a Massive Wide Dildo in Reverse Cowgirl
    05:36
    Tranny stretching her little Tight Asshole with a Massive Wide Dildo in Reverse Cowgirl
    CaliFauna
    10.4K views
    Crossdresser with Grandpa
    04:17
    Crossdresser with Grandpa
    Crossdressing Amateurs
    334K views
    Sex Machine Making my eyes roll
    00:40
    Sex Machine Making my eyes roll
    CaliFauna
    9.5K views
    Old Man Fucks Old Shemale.
    31:56
    Old Man Fucks Old Shemale.
    495.1K views
    T-girl riding a Huge 13-inch BBC Dildo struggling to put it in
    02:10
    T-girl riding a Huge 13-inch BBC Dildo struggling to put it in
    CaliFauna
    6.8K views
    Cute Pathan boy fucked by shemale
    09:48
    Cute Pathan boy fucked by shemale
    Erzi
    70.2K views
    Pink Slut
    01:37
    Pink Slut
    violet_bisex
    372 views
    Daddy fucks his sissy maid
    10:01
    Daddy fucks his sissy maid
    120.6K views
    Triple-BBC 12-inches Deep in Tranny's Ass
    00:40
    Triple-BBC 12-inches Deep in Tranny's Ass
    CaliFauna
    6.4K views
    Very Old Trannies
    01:41:54
    Very Old Trannies
    1.1M views
    Tranny Flopping her Dick, Stroking it and then Frotting with another Cock
    02:19
    Tranny Flopping her Dick, Stroking it and then Frotting with another Cock
    CaliFauna
    6K views
    Construction Worker Barebacks a Trans Man
    02:37
    Construction Worker Barebacks a Trans Man
    BI MEN CLUB
    160.9K views
    Tranny Oiled up Anal in the Bed with her Feet up in the air
    02:32
    Tranny Oiled up Anal in the Bed with her Feet up in the air
    CaliFauna
    3.5K views
    19 year old trans fucked hard by stranger in hotel room
    05:38
    19 year old trans fucked hard by stranger in hotel room
    Crystal Phoenix
    123.4K views
    Trans Girl devouring a huge 11-inch Realistic Dildo and Stroking her Dick
    00:59
    Trans Girl devouring a huge 11-inch Realistic Dildo and Stroking her Dick
    CaliFauna
    3.6K views
    Dads Bestmate Bangs Femboy
    05:11
    Dads Bestmate Bangs Femboy
    mothplayboy
    737.5K views
    Fauna enjoying Herself Fucking her own Ass
    02:22
    Fauna enjoying Herself Fucking her own Ass
    CaliFauna
    6.2K views
    Big daddy fuck 19 years old sissy
    06:34
    Big daddy fuck 19 years old sissy
    Crystal Phoenix
    119.4K views
    Filling my ASS with CUM and fucking it with a BBC  CUM-PLAY
    02:17
    Filling my ASS with CUM and fucking it with a BBC CUM-PLAY
    CaliFauna
    7.9K views
    Old Daddy Teacher fucking her fucked up Student
    09:29
    Old Daddy Teacher fucking her fucked up Student
    Latina Tranny
    176.3K views
    • Back
    • 1
    • 2
    • 3
    • 4
    • 5
    • 6
    • ...
    • 80
    • Next

    Searches Related to Sissy Boy And Old Man

    • Daddy Fucking Sissy Femboy
    • Old Man and Young Tgirl
    • Sissies Love Older Men
    • Step Dad Fucks Me
    • Mature Crossdresser With Straight Guy
    • Crossdressing Daddies
    • Fuck My Ass Please Dirty Talk
    • Secret Sissyboy
    • Transsexual Granny Mexican Shemale
    • Daddy's Girl
    • Crossdress Gangbang
    • Asian Ladyboy Grannies Shemales
    • Sissy-Virgin
    • Feminine Boys
    • Very Girly Ladyboys
    • Sissys Get Blacked
    • 2 Crossdressers Hotel
    • Tranny Stepmom
    • Real First Time
    • Dady

    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