Tag: Anal Sex (Cross-Dressing Man)

63 videos

JavGun has 63 JAV videos tagged Anal Sex (Cross-Dressing Man), released from August 2021 to November 2026. Top channels are Das, Glory Quest and MERCURY（マーキュリー）. Most featured are Asahinakou, Kohaku Matsumine and Nanako. It often comes with 123av, Japanese, Famous and Hd.

[Deep Throat Unleashed] A Documentary On The Simultaneous Stimulation Of Three Erogenous Zones—from The Back Of The Throat To The Clitoris And Anus. The Moment Of Feminization As She’s Penetrated To Her Deepest Depths, Her Eyes Rolling Back In Her Head As She Reaches A Mind-blowing Climax—Renka Yuzuki

DSOD-121

[Deep Throat Unleashed] A Documentary On The Simultaneous Stimulation Of Three Erogenous Zones—from The Back Of The Throat To The Clitoris And Anus. The Moment Of Feminization As She’s Penetrated To Her Deepest Depths, Her Eyes Rolling Back In Her Head As She Reaches A Mind-blowing Climax—Renka Yuzuki

TOTK-026 The otherworldly lewd transsexual elf's magic hole FUCK Matsumine Kohaku

TOTK-026

TOTK-026 The otherworldly lewd transsexual elf's magic hole FUCK Matsumine Kohaku

When I Dripped Aphrodisiac Oil Onto Her Swollen Nipples, Her Sensitivity Skyrocketed, Leading To A Convulsive, Stinging Orgasm And An Intense, Mind-blowing Climax—Ruri Mari

FEM-042

When I Dripped Aphrodisiac Oil Onto Her Swollen Nipples, Her Sensitivity Skyrocketed, Leading To A Convulsive, Stinging Orgasm And An Intense, Mind-blowing Climax—Ruri Mari

A Naturally Beautiful Transgender Girl. Mei Usatsuki

DSOD-116

A Naturally Beautiful Transgender Girl. Mei Usatsuki

HUSR-307 Transgender Reverse Pick-Up Sex [BEST] 252 Minutes of Non-Stop Orgasms and Climaxes from Cute Crossdressers – Nishino Megu

HUSR-307

HUSR-307 Transgender Reverse Pick-Up Sex [BEST] 252 Minutes of Non-Stop Orgasms and Climaxes from Cute Crossdressers – Nishino Megu

TIMD-044 Beautiful trans woman Churin: A 3-year record of masochistic training – Nakazawa Churin – Chulin Nakazawa

TIMD-044

TIMD-044 Beautiful trans woman Churin: A 3-year record of masochistic training – Nakazawa Churin – Chulin Nakazawa

New Half-Lesbian: Fully Erect Penis, Female Orgasm, Cosplay Live Stream Collaboration ♂ Yuna Nagisa / Nanako

NVH-089

New Half-Lesbian: Fully Erect Penis, Female Orgasm, Cosplay Live Stream Collaboration ♂ Yuna Nagisa / Nanako

New Half-Lesbian: Fully Erect Penis, Female Orgasm, Cosplay Live Stream Collaboration ♂ Yuna Nagisa / Nanako

NVH-089

New Half-Lesbian: Fully Erect Penis, Female Orgasm, Cosplay Live Stream Collaboration ♂ Yuna Nagisa / Nanako

An Incredibly Cute Boy-Girl Couple From Taiwan! ~ Junjun × Aiai: Lesbians Who Turn Each Other On With Anal Sex And Cocks!

TCD-352

An Incredibly Cute Boy-Girl Couple From Taiwan! ~ Junjun × Aiai: Lesbians Who Turn Each Other On With Anal Sex And Cocks!

An Incredibly Cute Boy-Girl Couple From Taiwan! ~ Junjun × Aiai: Lesbians Who Turn Each Other On With Anal Sex And Cocks!

TCD-352

An Incredibly Cute Boy-Girl Couple From Taiwan! ~ Junjun × Aiai: Lesbians Who Turn Each Other On With Anal Sex And Cocks!

I Can Never Be A Man Again. ~Two Female Bodies Trampled Upon As Sex Slaves For The Insane Ultra-Rich, Their Male Pride Shattered~ Renka Yuzuki, Hime Hanamiya

DSOD-079

I Can Never Be A Man Again. ~Two Female Bodies Trampled Upon As Sex Slaves For The Insane Ultra-Rich, Their Male Pride Shattered~ Renka Yuzuki, Hime Hanamiya

I Can't Stop Cumming!! School Uniform Penis Gal: Moe Kurumi

BOKD-321

I Can't Stop Cumming!! School Uniform Penis Gal: Moe Kurumi

New Half-Lesbian: Sensual Education For A Reclusive Student’s Penis During A Home Visit! A Slutty Teacher’s Special Extracurricular Lesson—Kou Asahina / Mayu Hazuki

NVH-088

New Half-Lesbian: Sensual Education For A Reclusive Student’s Penis During A Home Visit! A Slutty Teacher’s Special Extracurricular Lesson—Kou Asahina / Mayu Hazuki

[18cm Magnum-Sized Giant Penis Crossdresser] An Extremely Shy And Timid Beauty Falls Into Extreme Masochism [Moves To Tokyo With 3 Vibrators Inserted In Her Asshole] Sensitive Asshole Cunt Cums Instantly, Convulses, And Gets Drenched In Cum In A 4P Sex Scene

TPNS-038

[18cm Magnum-Sized Giant Penis Crossdresser] An Extremely Shy And Timid Beauty Falls Into Extreme Masochism [Moves To Tokyo With 3 Vibrators Inserted In Her Asshole] Sensitive Asshole Cunt Cums Instantly, Convulses, And Gets Drenched In Cum In A 4P Sex Scene

Short-Haired Cross-Dressing Gal: A Miraculous "Otokonya" Who Blends Boyish Charm And Cuteness

PETS-072

Short-Haired Cross-Dressing Gal: A Miraculous "Otokonya" Who Blends Boyish Charm And Cuteness

Cum-Soaked Schoolgirl In Uniform: Chapter 2—Nana Himeko

APPT-005

Cum-Soaked Schoolgirl In Uniform: Chapter 2—Nana Himeko

This Super-perverted IT Engineer Was A Creampie Sex Slave Who Was Totally Down For Endless Deep-throat Swallowing, Getting Pounded By A Massive Cock, And Going Wild With Ecstasy, Making Her A Total Masochist.

TANP-056

This Super-perverted IT Engineer Was A Creampie Sex Slave Who Was Totally Down For Endless Deep-throat Swallowing, Getting Pounded By A Massive Cock, And Going Wild With Ecstasy, Making Her A Total Masochist.

"Let's Jerk Off Together, Okay?" When I Confided My Dick Troubles To My Neighbor—a Transgender Nurse—she Flaunted Her Erect Penis, Gave Me Jerk-off Instructions, And Helped Me Cum Through JOI. Miyuki Shirachi

MOOC-027

"Let's Jerk Off Together, Okay?" When I Confided My Dick Troubles To My Neighbor—a Transgender Nurse—she Flaunted Her Erect Penis, Gave Me Jerk-off Instructions, And Helped Me Cum Through JOI. Miyuki Shirachi

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

HUSR-306

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

As A Cross-dresser, I'm Rock Hard Down There Again Today.

PETS-071

As A Cross-dresser, I'm Rock Hard Down There Again Today.

Mako Kobe: A Non-Hormone-Treating Boy Who Can Play Both Top And Bottom ♂

FEM-038

Mako Kobe: A Non-Hormone-Treating Boy Who Can Play Both Top And Bottom ♂

Stunningly Beautiful Cosplayer Strips Down—Shocking Full Erection: Crossdresser Screams In Ecstasy During Her First-Ever 5P Anal Sex, Cum-Drenched Orgy

TPNS-037

Stunningly Beautiful Cosplayer Strips Down—Shocking Full Erection: Crossdresser Screams In Ecstasy During Her First-Ever 5P Anal Sex, Cum-Drenched Orgy

As A Cross-dresser, I'm Rock Hard Down There Again Today.

PETS-071

As A Cross-dresser, I'm Rock Hard Down There Again Today.

Mako Kobe: A Non-Hormone-Treating Boy Who Can Play Both Top And Bottom ♂

FEM-038

Mako Kobe: A Non-Hormone-Treating Boy Who Can Play Both Top And Bottom ♂

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

TIMD-040

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

I'm Going To Become An AV Actress. Yuki Shinonome: Crossdressing Sex Slave Debut

TANP-055

I'm Going To Become An AV Actress. Yuki Shinonome: Crossdressing Sex Slave Debut

I'm Going To Become An AV Actress. Yuki Shinonome: Crossdressing Sex Slave Debut

TANP-055

I'm Going To Become An AV Actress. Yuki Shinonome: Crossdressing Sex Slave Debut

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

YAKO-098

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

Orgasm Game 2: A Big-Breasted Girlfriend Driven Wild And Brought To Orgasm By The Men She Hates. Kazuka Misono, Kana Yura, Mirai Nakamaru, Kasumi Matsumaru, Momiji Hiiragi

DSOD-010

Orgasm Game 2: A Big-Breasted Girlfriend Driven Wild And Brought To Orgasm By The Men She Hates. Kazuka Misono, Kana Yura, Mirai Nakamaru, Kasumi Matsumaru, Momiji Hiiragi

The Fleeting Blossom Of Flesh, The Nectar Of Subjugation. Pushing The Limits: Developing A Female Orifice To Reduce A Transwoman To A Female. Momiji Hiiragi, Mina Kitano

DSOD-013

The Fleeting Blossom Of Flesh, The Nectar Of Subjugation. Pushing The Limits: Developing A Female Orifice To Reduce A Transwoman To A Female. Momiji Hiiragi, Mina Kitano

SDAM-178 My and her (male) mutual insertion life

SDAM-178

SDAM-178 My and her (male) mutual insertion life

Before I Knew It, My Childhood Friend Had Turned Into A Black Gal With A Huge Ass—and A Boy’s Body. Jealous Of Her, She Teased Me By Flashing Her Asshole, And I Couldn’t Help But Get A Hard-on. We Ended Up Having Wild Sex, With Me Cumming Deep Inside Her Insatiable Asshole, And She Milked Every Last Drop Of “friendship Sperm” Out Of Me—and I Fell In Love With Her. Moka Tsunanatsu

MOOC-026

Before I Knew It, My Childhood Friend Had Turned Into A Black Gal With A Huge Ass—and A Boy’s Body. Jealous Of Her, She Teased Me By Flashing Her Asshole, And I Couldn’t Help But Get A Hard-on. We Ended Up Having Wild Sex, With Me Cumming Deep Inside Her Insatiable Asshole, And She Milked Every Last Drop Of “friendship Sperm” Out Of Me—and I Fell In Love With Her. Moka Tsunanatsu

A Cross-dressing Male Daycare Teacher Who Soothes Exhausted Parents With Sweet, Babyish Dirty Talk, Lets Them Suck On His Fully Erect Penis, And Heals Them With His “cock Milk” As He Ejaculates In Spurts—Mumu Kondo

MOOC-025

A Cross-dressing Male Daycare Teacher Who Soothes Exhausted Parents With Sweet, Babyish Dirty Talk, Lets Them Suck On His Fully Erect Penis, And Heals Them With His “cock Milk” As He Ejaculates In Spurts—Mumu Kondo

A Cross-dressing Male Daycare Teacher Who Soothes Exhausted Parents With Sweet, Babyish Dirty Talk, Lets Them Suck On His Fully Erect Penis, And Heals Them With His “cock Milk” As He Ejaculates In Spurts—Mumu Kondo

MOOC-025

A Cross-dressing Male Daycare Teacher Who Soothes Exhausted Parents With Sweet, Babyish Dirty Talk, Lets Them Suck On His Fully Erect Penis, And Heals Them With His “cock Milk” As He Ejaculates In Spurts—Mumu Kondo

Nanako's Reverse Anal Lesson

FEM-035

Nanako's Reverse Anal Lesson

YAKO-096 A super rare black gyaru/transgender woman has arrived in Kabukicho.

YAKO-096

YAKO-096 A super rare black gyaru/transgender woman has arrived in Kabukicho.

TIMD-035 A cross-dressing boy in a cage: Perverted masochistic breeding – Oryo

TIMD-035

TIMD-035 A cross-dressing boy in a cage: Perverted masochistic breeding – Oryo

PMGG-029 A nymphomaniac-type crossdresser and a slutty asshole sex session! 2D-level stunning visuals × nonstop sweet sadistic dirty talk torment that will drain you of sperm with a cum-filled anal fuck! [Eve-chan] Yumishiro Eve – Dream Castle Eve

PMGG-029

PMGG-029 A nymphomaniac-type crossdresser and a slutty asshole sex session! 2D-level stunning visuals × nonstop sweet sadistic dirty talk torment that will drain you of sperm with a cum-filled anal fuck! [Eve-chan] Yumishiro Eve – Dream Castle Eve

PMGG-030 A national treasure-class big dick beautiful girl ♂ and a super slutty asshole sex! She has a boyfriend but her sex friend's dick is a different story ♪ "Please put your dick in me, it's bigger and harder than my boyfriend's…//" A lovey-dovey sex session filled with dick-flirting dirty talk from beginning to end. [Fuyuka] Tsukishiro Fuyuka

PMGG-030

PMGG-030 A national treasure-class big dick beautiful girl ♂ and a super slutty asshole sex! She has a boyfriend but her sex friend's dick is a different story ♪ "Please put your dick in me, it's bigger and harder than my boyfriend's…//" A lovey-dovey sex session filled with dick-flirting dirty talk from beginning to end. [Fuyuka] Tsukishiro Fuyuka

"Master, You're A Pervert, Aren't You?" A Little Devil Slut Maid Who Pleases Your Asshole: Transgender Reverse Anal Sex♂ Kou Asahina

NVH-083

"Master, You're A Pervert, Aren't You?" A Little Devil Slut Maid Who Pleases Your Asshole: Transgender Reverse Anal Sex♂ Kou Asahina

"Akari Shinmura" Destroys Transwoman "Ena Hisa" With Strap-On Anal Sex!!

CEMD-864

"Akari Shinmura" Destroys Transwoman "Ena Hisa" With Strap-On Anal Sex!!

No Script, No Direction, No Acting—A 1-on-1 Encounter Where She Surrenders To Pleasure, Guided Solely By Her Instincts: Yuki Takeuchi

DSOD-104

No Script, No Direction, No Acting—A 1-on-1 Encounter Where She Surrenders To Pleasure, Guided Solely By Her Instincts: Yuki Takeuchi

At That Personal Gym Everyone’s Been Talking About, I Fell Into The Seductive Trap Set By Hamichin, A Super-sexy, Muscular Female Instructor, And Before I Knew It, I Had A Full-on Erection And Was Pumped Up! She Took A Liking To My Rock-hard, Massive Cock, And As She Rocked Her Little Dick Back And Forth In The Cowgirl Position, She Milked Me Over And Over Again. Suzune Nico

MOOC-023

At That Personal Gym Everyone’s Been Talking About, I Fell Into The Seductive Trap Set By Hamichin, A Super-sexy, Muscular Female Instructor, And Before I Knew It, I Had A Full-on Erection And Was Pumped Up! She Took A Liking To My Rock-hard, Massive Cock, And As She Rocked Her Little Dick Back And Forth In The Cowgirl Position, She Milked Me Over And Over Again. Suzune Nico

The Story Of How I Asked My Friend’s Younger Sister—a Cross-dressing J-style Girl—about Anal Masturbation Out Of Curiosity, Only To Be Taught How To Have Anal Sex With A Huge Cock During My First Prostate Stimulation Session And End Up Experiencing A Female Orgasm. Yuri Ichinisan

MOOC-024

The Story Of How I Asked My Friend’s Younger Sister—a Cross-dressing J-style Girl—about Anal Masturbation Out Of Curiosity, Only To Be Taught How To Have Anal Sex With A Huge Cock During My First Prostate Stimulation Session And End Up Experiencing A Female Orgasm. Yuri Ichinisan

Is She A Beautiful Girl? No, I Am A Beautiful Boy Dressed As A Woman. "II

NVH-082

Is She A Beautiful Girl? No, I Am A Beautiful Boy Dressed As A Woman. "II

Is She A Beautiful Girl? No, I Am A Beautiful Boy Dressed As A Woman. "II

NVH-082

Is She A Beautiful Girl? No, I Am A Beautiful Boy Dressed As A Woman. "II

TOTK-023-UNCENSORED-LEAK

TOTK-023

TOTK-023-UNCENSORED-LEAK

I Fall In Love With A Boy-Girl: Kohaku Matsumine

HERY-171

I Fall In Love With A Boy-Girl: Kohaku Matsumine

Excavated Man's Daughter♂AVDebut Amane Rui

FEM-034

Excavated Man's Daughter♂AVDebut Amane Rui

I Fall In Love With A Boy-Girl: Kohaku Matsumine

HERY-171

I Fall In Love With A Boy-Girl: Kohaku Matsumine

A Tall, Good-Looking Trans Woman (175 Cm) ~ Forced Orgasms With No Escape Through Reverse Anal And Hard-Pounding Sex Training ~ Aoi Hibiki

TCD-338

A Tall, Good-Looking Trans Woman (175 Cm) ~ Forced Orgasms With No Escape Through Reverse Anal And Hard-Pounding Sex Training ~ Aoi Hibiki

"Raira Kurusu," The Girl With Amazing Skills, Trains A Professional Male Performer! ~ Anal Training And A Huge Dick: Female-Style Orgasm Reverse Anal Sex

TCD-339

"Raira Kurusu," The Girl With Amazing Skills, Trains A Professional Male Performer! ~ Anal Training And A Huge Dick: Female-Style Orgasm Reverse Anal Sex

"Mel," A 176cm Tall, Model-Like Trans Woman—Three Consecutive Anal Sex Scenes As She Falls Into Depravity Through Anal Rape, Sleep Rape, And Housekeeper Rape!!

SAL-263

"Mel," A 176cm Tall, Model-Like Trans Woman—Three Consecutive Anal Sex Scenes As She Falls Into Depravity Through Anal Rape, Sleep Rape, And Housekeeper Rape!!

After Discovering Each Other’s True Identities, I Met A “beautiful, Mature” Mom Friend At A Brothel And Had A Secret Affair. Reika Natsume

DSOD-070

After Discovering Each Other’s True Identities, I Met A “beautiful, Mature” Mom Friend At A Brothel And Had A Secret Affair. Reika Natsume

After Discovering Each Other’s True Identities, I Met A “beautiful, Mature” Mom Friend At A Brothel And Had A Secret Affair. Reika Natsume

DSOD-070

After Discovering Each Other’s True Identities, I Met A “beautiful, Mature” Mom Friend At A Brothel And Had A Secret Affair. Reika Natsume

TOTK-022 A stunningly beautiful woman with a top-tier penis, unleashing her primal instincts and getting a full erection for anal sex.

TOTK-022

TOTK-022 A stunningly beautiful woman with a top-tier penis, unleashing her primal instincts and getting a full erection for anal sex.

MAQQH-007 A straight, handsome man's shocking anal debut transforms him into a slutty crossdresser—a must-see video for enthusiasts.

MAQQH-007

MAQQH-007 A straight, handsome man's shocking anal debut transforms him into a slutty crossdresser—a must-see video for enthusiasts.

YAKO-094 The beautiful career woman's true nature was that of a secretly perverted, masochistic transsexual. A leaked video of her having sex six times would be the end of her career if her colleagues saw it.

YAKO-094

YAKO-094 The beautiful career woman's true nature was that of a secretly perverted, masochistic transsexual. A leaked video of her having sex six times would be the end of her career if her colleagues saw it.

Supernova: New Half AVDEBUT - Kou Asahina

NVH-081

Supernova: New Half AVDEBUT - Kou Asahina

AV Debut - I Look Like This, But I Have A Penis. Chika Saotome

BOKD-320

AV Debut - I Look Like This, But I Have A Penis. Chika Saotome