Anal Sex Cross Dressing Man

MOOC-027 "Let's squirt together," said my transsexual nurse neighbor when I confided in her about my penis problems. She showed me her erect penis and gave me instructions to masturbate, giving me a JOI (jerk off) and helping me cum together. - Miyuki Shirachi

MOOC-027 "Let's squirt together," said my transsexual nurse neighbor when I confided in her about my penis problems. She showed me her erect penis and gave me instructions to masturbate, giving me a JOI (jerk off) and helping me cum together. - Miyuki Shirachi

Mocco/Delusional group · Aug 29, 2026

MOOC-028 Despite having the most stunning looks, this cross-dressing call girl was incredibly cold and unresponsive. I lectured her, held her in a headlock, gave her a handjob until she peed herself and squirted, and once I made her understand, we became intimate, loving, and had anal sex with her. - Yuna Otonashi

MOOC-028 Despite having the most stunning looks, this cross-dressing call girl was incredibly cold and unresponsive. I lectured her, held her in a headlock, gave her a handjob until she peed herself and squirted, and once I made her understand, we became intimate, loving, and had anal sex with her. - Yuna Otonashi

Mocco/Delusional group · Aug 29, 2026

PMGG-032 Too beautiful cheating sex friend ♂ and anal sex with unrestrained sexual desire! "This is the last time today... so I want you to torment my ass pussy to your heart's content..." A slender body x naughty nipples x frustrated ass pussy that will make you uncontrollably aroused as you impregnate her in a memorable fuck. [Izumi] Ayukawa Izumi

PMGG-032 Too beautiful cheating sex friend ♂ and anal sex with unrestrained sexual desire! "This is the last time today... so I want you to torment my ass pussy to your heart's content..." A slender body x naughty nipples x frustrated ass pussy that will make you uncontrollably aroused as you impregnate her in a memorable fuck. [Izumi] Ayukawa Izumi

Giga de rain · Aug 28, 2026

HUSR-306 Forbidden Incestuous Intercourse with Top-Tier Transgender Women: A Luxurious Drama Collection of 8 Episodes (4 Hours)

HUSR-306 Forbidden Incestuous Intercourse with Top-Tier Transgender Women: A Luxurious Drama Collection of 8 Episodes (4 Hours)

Big Morkal · Aug 22, 2026

TCD-346 Japan's first transsexual AV director, Himeoka Shia, directs! Transsexual lesbian sex tape close-up date 5 with Ashiro Rio

TCD-346 Japan's first transsexual AV director, Himeoka Shia, directs! Transsexual lesbian sex tape close-up date 5 with Ashiro Rio

TRANS CLUB · Aug 22, 2026

FEM-037 I thought he was a tough, dangerous type, but it turns out he's an incredibly shy, masochistic cross-dressing boy♂ - Hanasou Maaya

FEM-037 I thought he was a tough, dangerous type, but it turns out he's an incredibly shy, masochistic cross-dressing boy♂ - Hanasou Maaya

O-Peni-Peni World Femboy/Delusional Group · Aug 22, 2026

FEM-038 A non-hormone-using cross-dressing boy ♂, Makoto Kobe, is an all-rounder who can be both the top and the bottom.

FEM-038 A non-hormone-using cross-dressing boy ♂, Makoto Kobe, is an all-rounder who can be both the top and the bottom.

O-Peni-Peni World Femboy/Delusional Group · Aug 22, 2026

HERY-173 Crossdressing Boys, Complete Feminization Collection 57: Yu Kataoka

HERY-173 Crossdressing Boys, Complete Feminization Collection 57: Yu Kataoka

YELLOW / Mousouzoku · Aug 22, 2026

NVH-085 Consecutive orgasms! Full erection double penis clit slut transsexual reverse 3P harem! Nanako/Aise Mei

NVH-085 Consecutive orgasms! Full erection double penis clit slut transsexual reverse 3P harem! Nanako/Aise Mei

Glory Quest · Aug 22, 2026

PETS-071 As a crossdresser, my dick is throbbing today.

PETS-071 As a crossdresser, my dick is throbbing today.

PETSHOP / Daydream Tribe · Aug 22, 2026

SAL-265 Aoi Hibiki, a tall, beautiful cross-dressing boy at 175cm. Three consecutive scenes of anal sex with his exquisite ass and extremely lewd sexual activities!!

SAL-265 Aoi Hibiki, a tall, beautiful cross-dressing boy at 175cm. Three consecutive scenes of anal sex with his exquisite ass and extremely lewd sexual activities!!

SHEMALE a la carte · Aug 22, 2026

TCD-347 A day in the life of me and my girlfriend with a penis, a taxi date 8 - Hana Kanade Maya

TCD-347 A day in the life of me and my girlfriend with a penis, a taxi date 8 - Hana Kanade Maya

TRANS CLUB · Aug 22, 2026

TPNS-037 A stunningly beautiful cosplayer is stripped naked and becomes a fully erect crossdresser, screaming and cumming wildly during her first ever 5P anal sex session, getting covered in cum in a massive orgy.

TPNS-037 A stunningly beautiful cosplayer is stripped naked and becomes a fully erect crossdresser, screaming and cumming wildly during her first ever 5P anal sex session, getting covered in cum in a massive orgy.

All-Japan Amateur Photographers Union/Daydream Fantasy Lovers · Aug 22, 2026

DSOD-006 [Ochin Airlines] Dasu! An airline presents a superb flight experience with top-class flight attendants who will serve you with polite language and a sensual touch. Special episode featuring Marina Ikeda, Renka Yuzuki, Momiji Hiiragi, and Ram Ichinose.

DSOD-006 [Ochin Airlines] Dasu! An airline presents a superb flight experience with top-class flight attendants who will serve you with polite language and a sensual touch. Special episode featuring Marina Ikeda, Renka Yuzuki, Momiji Hiiragi, and Ram Ichinose.

Das · Aug 21, 2026

VRPRD-209 [VR] [8K] Continuous nipple orgasms with sticky massage on flat breasts! Newhalf nipple development esthetician Hanamiya Hime

VRPRD-209 [VR] [8K] Continuous nipple orgasms with sticky massage on flat breasts! Newhalf nipple development esthetician Hanamiya Hime

VR paradise · Aug 20, 2026

VRPRD-208 [VR][8K] My subordinate, who I ended up sharing a room with on a business trip, turned out to be a trans woman. We had aphrodisiac sex until morning, with her cumming so much inside her anus that it overflowed. Nanako

VRPRD-208 [VR][8K] My subordinate, who I ended up sharing a room with on a business trip, turned out to be a trans woman. We had aphrodisiac sex until morning, with her cumming so much inside her anus that it overflowed. Nanako

VR paradise · Aug 15, 2026

KTKN-014 A charismatic transsexual sex worker secretly made an appointment privately, then passed the information around to her friends, and for a flat fee of 18,000 yen, she had unlimited anal sex with 6 men.

KTKN-014 A charismatic transsexual sex worker secretly made an appointment privately, then passed the information around to her friends, and for a flat fee of 18,000 yen, she had unlimited anal sex with 6 men.

Kitixx/Mousouzoku · Aug 15, 2026

TANP-055 I'm going to be an AV actress. Shinonome Yuki, a crossdressing sex slave, makes her debut.

TANP-055 I'm going to be an AV actress. Shinonome Yuki, a crossdressing sex slave, makes her debut.

Dandelions/Daydream Family · Aug 15, 2026

TIMD-041 Crossdresser's Masochistic Orgasm

TIMD-041 Crossdresser's Masochistic Orgasm

Sanwa Shuppan · Aug 14, 2026

TIMD-040 Stunningly beautiful cock-loving Kana-san gets fucked in a wild orgy with multiple cocks and continuous anal cumshots!! Sakiyuki Kana

TIMD-040 Stunningly beautiful cock-loving Kana-san gets fucked in a wild orgy with multiple cocks and continuous anal cumshots!! Sakiyuki Kana

Sanwa Shuppan · Aug 14, 2026

YAKO-098 [Leaked from the Kabuki Host Club Scene] Video of extremely handsome straight men losing their anal virginity while cross-dressing for the first time

YAKO-098 [Leaked from the Kabuki Host Club Scene] Video of extremely handsome straight men losing their anal virginity while cross-dressing for the first time

MERCURY · Aug 12, 2026

VRPRD-205 [VR] [8K] Bullied, hard-on masochistic transsexual gets massive anal cumshot. Kotori Takanashi Kanon

VRPRD-205 [VR] [8K] Bullied, hard-on masochistic transsexual gets massive anal cumshot. Kotori Takanashi Kanon

VR paradise · Aug 8, 2026

SAL-264 Cute-smiling crossdresser Kondo Mumu gets aroused and erect! ~Tight pants showing, black pantyhose attack and verbal abuse from two girls with big dicks in a 3P sex with three consecutive raw cumshots!

SAL-264 Cute-smiling crossdresser Kondo Mumu gets aroused and erect! ~Tight pants showing, black pantyhose attack and verbal abuse from two girls with big dicks in a 3P sex with three consecutive raw cumshots!

SHEMALE a la carte · Aug 8, 2026

TCD-344 A day in the life of me and my girlfriend with a penis, a taxi date 7 AiAi

TCD-344 A day in the life of me and my girlfriend with a penis, a taxi date 7 AiAi

TRANS CLUB · Aug 8, 2026