Search: first time crossdressing - 280 movies

Filter
My first crossdressing adventure: exploring new horizons
My first crossdressing adventure: exploring new horizons
Inexperienced sissy takes her first dildo on camera
Inexperienced sissy takes her first dildo on camera
Gia itzel strapon, big ass fucked
Gia itzel strapon, big ass fucked
My first time crossdressing got me hot with blowjob, anal and lingerie
My first time crossdressing got me hot with blowjob, anal and lingerie
First-time crossdresser Kitty enjoys making steamy videos in her room
First-time crossdresser Kitty enjoys making steamy videos in her room
First time crossdresser gets his tight ass pumped for the first time
First time crossdresser gets his tight ass pumped for the first time
First-time crossdresser Kelly enjoys a morning drive in black pantyhose and boots while pleasuring her sissy cock
First-time crossdresser Kelly enjoys a morning drive in black pantyhose and boots while pleasuring her sissy cock
First-time crossdresser Kellycd2022, a gorgeous cougar, enjoys wetting her panties during a scenic drive in pantyhose, fishnet stockings, and high heels
First-time crossdresser Kellycd2022, a gorgeous cougar, enjoys wetting her panties during a scenic drive in pantyhose, fishnet stockings, and high heels
First time, first crossdress
First time, first crossdress
First time virgin crossdresser, first time
First time virgin crossdresser, first time
First time, first
First time, first
Steamy masturbation as a hot Latino crossdresses for the first time
Steamy masturbation as a hot Latino crossdresses for the first time
Crossdresser cumshots, crossdresser mature sex
Crossdresser cumshots, crossdresser mature sex
First, first time virgin crossdresser
First, first time virgin crossdresser
Sissy first blowjob, crossdresser blowjob
Sissy first blowjob, crossdresser blowjob
Inexperienced sissy dressed up for the first time to please daddy
Inexperienced sissy dressed up for the first time to please daddy
Boy first time fucking, young amateur boys
Boy first time fucking, young amateur boys
First-time amateur crossdresser experiences a new adventure
First-time amateur crossdresser experiences a new adventure
First time virgin crossdresser, first time
First time virgin crossdresser, first time
BBW dominatrix pegs her crossdressing sissy husband for the first time in black dress and bra while wearing a mask and socks
BBW dominatrix pegs her crossdressing sissy husband for the first time in black dress and bra while wearing a mask and socks
My first time exploring crossdressing as a sissy felt so freeing
My first time exploring crossdressing as a sissy felt so freeing
Trans hottie Alex Vicious gets down for her first time in a wild romp
Trans hottie Alex Vicious gets down for her first time in a wild romp
Unforgettable first experience as a sissy surpasses all expectations!
Unforgettable first experience as a sissy surpasses all expectations!
My journey to sissyhood: experiencing it for the first time
My journey to sissyhood: experiencing it for the first time
First time experience for a handsome crossdresser
First time experience for a handsome crossdresser
My debut as a crossdressing sissy: a first-time amateur experience
My debut as a crossdressing sissy: a first-time amateur experience
Crossdresser's debut solo with toy for the first time
Crossdresser's debut solo with toy for the first time
Travestis amateur french, first time
Travestis amateur french, first time
Crossdresser whore enjoys kinky crossdressing sex fun
Crossdresser whore enjoys kinky crossdressing sex fun
Crossdresser first time dressed, first time swallowing loads
Crossdresser first time dressed, first time swallowing loads
Peeking under skirt reveals hidden trouser snake
Peeking under skirt reveals hidden trouser snake
Sissy's unforgettable first experience with crossdressing and self-pleasure
Sissy's unforgettable first experience with crossdressing and self-pleasure
IvoryFemboiTrap enjoys some solo fun... once more.
IvoryFemboiTrap enjoys some solo fun... once more.
First time shemale, all new
First time shemale, all new
Satisfy my tight ass with a passionate rimming session - I crave it!
Satisfy my tight ass with a passionate rimming session - I crave it!
Amateur crossdresser enjoys a self-facial cum gulp in lingerie
Amateur crossdresser enjoys a self-facial cum gulp in lingerie
First time virgin crossdresser, virgin crossdresser
First time virgin crossdresser, virgin crossdresser
Cd bbc creampie, argentina
Cd bbc creampie, argentina
Discovering my sissy side for the first time was truly empowering
Discovering my sissy side for the first time was truly empowering
Inexperienced crossdresser barebacks with white top in November meeting
Inexperienced crossdresser barebacks with white top in November meeting
Transgender virgin boy explores pleasure with silver-haired Japanese Newhalf college girl
Transgender virgin boy explores pleasure with silver-haired Japanese Newhalf college girl
Amateur crossdresser naylon27 explores their feminine side for the first time!
Amateur crossdresser naylon27 explores their feminine side for the first time!
Mature crossdressers, crossdresser cum
Mature crossdressers, crossdresser cum
Youthful t-girl with blue hair takes on a huge 15-inch dildo from Bad Dragon
Youthful t-girl with blue hair takes on a huge 15-inch dildo from Bad Dragon
First crossdressers sex, crossdressers first time fucked
First crossdressers sex, crossdressers first time fucked
Naughty sissy kitty gets drilled by experienced crossdressing MILF
Naughty sissy kitty gets drilled by experienced crossdressing MILF
Lunn's Solo Anal Adventure: Japanese Transgender Babe Explores Pleasure with Adult Toys!
Lunn's Solo Anal Adventure: Japanese Transgender Babe Explores Pleasure with Adult Toys!
Inexperienced teen cross dresser experiences public bathroom sex and cum in mouth
Inexperienced teen cross dresser experiences public bathroom sex and cum in mouth
Popular categories
TeenWorkplaceCreampieDeepthroatAnal creampieHomemadeAmateurFistingReal lifeshowShower bathOutsideThreesomeUpskirtEbonyGirly guy