PornPorn Transgender • US
  • Videos
  • Short videos
  • photos
  • Users
    Forgot password
    Sign in with Google
    Sign in with X
    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
    • Black
    • Big Cock
    • 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
    Dating
    Subscriptions
    • Upload
    LET IT SNOW, LET IT SAVE! ☃️ Faphouse Discounts – Winter Edition
    Search in orientations
    Minimum quality
    720p+
    1080p+
    2160p+
    • Relevance
    • Date
    • Views
    • Rating
    • Duration
    Filter by Categories
    • Shemale Fucks Guy
    • Black
    • Big Cock
    • Shemale Fucks Shemale
    • Amateur
    • Shemale Fucks Girl
    • Sissy
    • Ladyboy
    • Guy Fucks Shemale
    • Compilation
    • Blowjob
    • Big Black Cock
    • Cum In Mouth
    • Big Ass
    • Creampie
    • Bareback
    • Cumshot
    • Mature
    • Homemade
    • Teen
    Duration (min)
    Date
    Production
    FPS
    Exclude categories
    Reset all filters

    Sissy Guy Pegging Porn Videos

    Free Videos
    Short videos
    Premium Videos
    Photos
    Best Videos
    By clicking the content you will also see an ad. AD
    Hot Blonde Trans Woman Pegged
    01:12
    Hot Blonde Trans Woman Pegged
    Bailey Wilde
    1.5K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6
    20:07
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 6
    Bailey Wilde
    369 views
    Big cock TGirl body swappers with Lucy and Charlotte
    06:00
    Big cock TGirl body swappers with Lucy and Charlotte
    Spike Essex
    23.6K views
    Hot Trans Woman Pegged by Mistress Pixie
    02:58
    Hot Trans Woman Pegged by Mistress Pixie
    Bailey Wilde
    7.7K views
    Hot Crossdresser Pegged with HUGE Strapon
    02:03
    Hot Crossdresser Pegged with HUGE Strapon
    Bailey Wilde
    2.4K views
    Lady Alice (9:16) 09 Part 3 - Bride Diaries - Full HD 60fps
    09:56
    Lady Alice (9:16) 09 Part 3 - Bride Diaries - Full HD 60fps
    Mesmeriza
    5.5K views
    Sissy Home Pegging
    05:32
    Sissy Home Pegging
    Lola Spais
    20K views
    Hot Trans Woman Pegged by Dominatrix
    12:50
    Hot Trans Woman Pegged by Dominatrix
    Bailey Wilde
    11.8K views
    Wrecking my ass BG buttplug anal strech huge buttplug
    01:04
    Wrecking my ass BG buttplug anal strech huge buttplug
    Nikolhasty
    11.6K views
    Hot Crossdressing Maid Pegged
    07:20
    Hot Crossdressing Maid Pegged
    Bailey Wilde
    3.1K views
    Hot Crossdresser Reverse Cowgirl Pegged
    02:34
    Hot Crossdresser Reverse Cowgirl Pegged
    Bailey Wilde
    1.8K views
    Lady Alice Compilation 10 Lady Alice's Secret View Originals
    11:32
    Lady Alice Compilation 10 Lady Alice's Secret View Originals
    Mesmeriza
    6K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 7
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 7
    Bailey Wilde
    2.4K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 20
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 20
    Bailey Wilde
    1.6K views
    Sissy Joyce getting pegged
    00:23
    Sissy Joyce getting pegged
    Sissy Joyce
    28.4K views
    Sissy Lucy getting pegged in Chastity with the  dildo
    05:19
    Sissy Lucy getting pegged in Chastity with the dildo
    Onlyfans
    22.8K views
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    06:00
    Femdom Double Anal Pegging for Chastity Sissy Lucy
    Onlyfans
    18.4K views
    Lucy Getting pegged with glow in the dark alien knot dildo
    05:21
    Lucy Getting pegged with glow in the dark alien knot dildo
    Onlyfans
    9.3K views
    Hot Crossdressing Babe Pegged with HUGE Strapon
    05:59
    Hot Crossdressing Babe Pegged with HUGE Strapon
    Bailey Wilde
    2.3K views
    Lady Alice compilation 10 Lady Alice's Secret (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR
    11:32
    Lady Alice compilation 10 Lady Alice's Secret (mesmerize version) View originals by subscription 4K UHD 60 FPS HDR
    FapHouse
    7K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 17
    40:24
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 17
    Bailey Wilde
    just added
    Hot Trans Woman Cowgirl Pegged
    04:45
    Hot Trans Woman Cowgirl Pegged
    Bailey Wilde
    13.7K views
    Abusing My Boi Pussy Full Length Video
    19:26
    Abusing My Boi Pussy Full Length Video
    Tiffany Ciskiss
    32K views
    Sissy Peg is back in town
    05:25
    Sissy Peg is back in town
    16.7K views
    Amateur sissy pegging
    02:42
    Amateur sissy pegging
    xxxycaption
    7K views
    Pegging My Sissy Gurlfriend
    00:40
    Pegging My Sissy Gurlfriend
    Fetish Explorers
    3.1K views
    26cm (10 inch) big strapon deep in femboy ass
    05:48
    26cm (10 inch) big strapon deep in femboy ass
    Marie CD
    5.9K views
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 12
    08:12
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 12
    FapHouse
    4K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 10
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 10
    Bailey Wilde
    2.5K views
    Lady Alicepart 1 (original Version)
    05:20
    Lady Alicepart 1 (original Version)
    Mesmeriza
    6.8K views
    SHEMALE SEXYBRODY GETS A PLUGGED IN HOT IRON IN HER CUNT
    00:58
    SHEMALE SEXYBRODY GETS A PLUGGED IN HOT IRON IN HER CUNT
    Many Vids
    7.6K views
    Hot Trans Babe Pegged in HUGE ASS
    02:15
    Hot Trans Babe Pegged in HUGE ASS
    Bailey Wilde
    2.9K views
    Princesses Olivia loves to be pegged
    02:53
    Princesses Olivia loves to be pegged
    Olivia Soren
    1.9K views
    Mistress Pegs Emo Crossdresser and Makes Her Swallow Cum
    00:29
    Mistress Pegs Emo Crossdresser and Makes Her Swallow Cum
    Bailey Wilde
    4.1K views
    Jasmine_dlight & Valentina Rosa & Ava Black - the Slut Sandwich Extreme Strapon Domination - Extreme Anal Shemale Slut
    00:31
    Jasmine_dlight & Valentina Rosa & Ava Black - the Slut Sandwich Extreme Strapon Domination - Extreme Anal Shemale Slut
    Jasmine_dlight
    3K views
    Jasmine Dlight & Mistress Prin - Hard and Heavy Pegging
    00:30
    Jasmine Dlight & Mistress Prin - Hard and Heavy Pegging
    Jasmine_dlight
    1.2K views
    TS SEXYBRODY IS TRANS NASTY AS THE HAIRDRESSERS FUCK SLUT
    01:06
    TS SEXYBRODY IS TRANS NASTY AS THE HAIRDRESSERS FUCK SLUT
    6.8K views
    Hard fucking with a big fat dildo
    01:33
    Hard fucking with a big fat dildo
    Zoeycdgirl
    2.5K views
    Sissy Pegged by Mistress Pixie
    02:23
    Sissy Pegged by Mistress Pixie
    Bailey Wilde
    2.4K views
    Hot Sissy Babe Pegged
    03:33
    Hot Sissy Babe Pegged
    Bailey Wilde
    1.9K views
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 4
    08:12
    Mistress Pixie Strapon Fucking Sissy Bailey Wilde - Compilation 4
    Bailey Wilde
    2.4K views
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 15
    20:07
    Mistress Pixie Pegging Crossdresser Bailey Wilde - Compilation 15
    Bailey Wilde
    just added
    Hot Trans Woman Reverse Cowgirl Pegged
    04:06
    Hot Trans Woman Reverse Cowgirl Pegged
    Bailey Wilde
    5.8K views
    Sissy pegged by mistress
    00:27
    Sissy pegged by mistress
    6.2K views
    TS SEXYBRODY AND MISTRESS SARAH FONDLY REMEMBER STEPDAD
    01:05
    TS SEXYBRODY AND MISTRESS SARAH FONDLY REMEMBER STEPDAD
    6.3K views
    Huge 13 incl XXL dildo in sissy - Part one
    05:03
    Huge 13 incl XXL dildo in sissy - Part one
    Ylvis88
    19.2K views
    NikolHasty playing  with huge buttplug monster toy anal destruction BG
    02:11
    NikolHasty playing with huge buttplug monster toy anal destruction BG
    Nikolhasty
    5.4K views
    • Back
    • 1
    • ...
    • 6
    • 7
    • 8
    • 9
    • 10
    • ...
    • 80
    • Next

    Searches Related to Sissy Guy Pegging

    • Cuckold Humiliation
    • Crossdresser Domination
    • Pegged in Panties
    • Crossdressed to Be Fucked
    • Truckers Fuck CD Tway Crossdressers
    • Bdsm Fisting
    • Femboys and Sissys
    • Femboy BBC
    • Shemale Bondage
    • Ladyboy Fucking Straight Boy Tailand
    • Big Dick Stroking
    • Cum in His Mouth
    • Deep Pussy Pounding
    • Slutty Nasty Crossdressing Gurl
    • Step Mom Made Some Into a Sissy
    • Monster Cock Domination
    • Extreme Anal Dildo
    • Straight Guy BDSM
    • Girlfriend Pegging
    • Cuckold Crossdresser
    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