Anal sex (cross-dressing man)

When A Feminine Man Seriously Cross-dresses, He Becomes A Stunning Beauty And Makes His Debut As A Newcomer. - Shiroro

When A Feminine Man Seriously Cross-dresses, He Becomes A Stunning Beauty And Makes His Debut As A Newcomer. - Shiroro

Censored
fem-040
Short-haired Crossdressing Gal: A Miraculous Boy Who Blends Boyishness And Cuteness.

Short-haired Crossdressing Gal: A Miraculous Boy Who Blends Boyishness And Cuteness.

Censored
pets-072
[Magnum 18cm Class Giant Penis Crossdresser] Extremely Shy And Introverted Beautiful Girl Becomes A Total Masochistic Slut [Three Rotors Inserted Into Her Anus And She Comes To Tokyo] Sensitive Ass Pussy Instantly Orgasms And Convulses, Soaked In Semen In 4P Sex

[Magnum 18cm Class Giant Penis Crossdresser] Extremely Shy And Introverted Beautiful Girl Becomes A Total Masochistic Slut [Three Rotors Inserted Into Her Anus And She Comes To Tokyo] Sensitive Ass Pussy Instantly Orgasms And Convulses, Soaked In Semen In 4P Sex

Censored
tpns-038
AV Debut: I May Look Like This, But I Have A Penis. - Kano Kawamiya

AV Debut: I May Look Like This, But I Have A Penis. - Kano Kawamiya

Censored
bokd-320
Women-only Penis Night Pool: Marina Ikeda, Renka Yuzuki, Momiji Hiiragi, Ram Ichinose

Women-only Penis Night Pool: Marina Ikeda, Renka Yuzuki, Momiji Hiiragi, Ram Ichinose

Censored
dsod-010
The Secretly Perverted IT Engineer Was A Cum-filled Flesh Toilet, A Cross-dressing Boy Who Was Okay With Endless Deep Throat Swallowing, And A Masochistic Girl Who Would Go Crazy With Pleasure As A Huge Cock Was Thrust Into Her.

The Secretly Perverted IT Engineer Was A Cum-filled Flesh Toilet, A Cross-dressing Boy Who Was Okay With Endless Deep Throat Swallowing, And A Masochistic Girl Who Would Go Crazy With Pleasure As A Huge Cock Was Thrust Into Her.

Censored
tanp-056
The Slutty Crossdresser's Orgasmic Anal

The Slutty Crossdresser's Orgasmic Anal

Censored
timd-043
A 175cm Tall Cross-dressing Man Goes On A Drunken 'reverse Anal' Date With Hibiki Aoi.

A 175cm Tall Cross-dressing Man Goes On A Drunken 'reverse Anal' Date With Hibiki Aoi.

Censored
tcd-348
A Day In The Life Of Me And My Girlfriend With A Penis, A Taxi Date 9 Junjun

A Day In The Life Of Me And My Girlfriend With A Penis, A Taxi Date 9 Junjun

Censored
tcd-349
Influencer Crossdresser Girl Gokkun OFF Meeting Hime Hanamiya Hime

Influencer Crossdresser Girl Gokkun OFF Meeting Hime Hanamiya Hime

Censored
avsa-454
An Eye For An Eye. Exposing The Perverse Sexual Fetishes Of The Transsexual Female Executive Who Blamed Her For An Ordering Mistake, And Turning Her From A Humiliating Groveling To A Masochistic Sex Slave: A Corporate Rebellion And Revenge. Yuzuki Renka

An Eye For An Eye. Exposing The Perverse Sexual Fetishes Of The Transsexual Female Executive Who Blamed Her For An Ordering Mistake, And Turning Her From A Humiliating Groveling To A Masochistic Sex Slave: A Corporate Rebellion And Revenge. Yuzuki Renka

Censored
dsod-058
[Boys' School Trip] But I Have A Penis A Beautiful Boy Who Is A Transfer Student Seduces The Straight Virgins And Warps Their Sexual Preferences During A Tempting Overnight Camp. - Momiji Hiiragi

[Boys' School Trip] But I Have A Penis A Beautiful Boy Who Is A Transfer Student Seduces The Straight Virgins And Warps Their Sexual Preferences During A Tempting Overnight Camp. - Momiji Hiiragi

Censored
dsod-057
Her Eyes Roll Back As She's Relentlessly Teased, Her Love Juices Dripping As She Cries And Sobs In A Frenzy Of Orgasms - NH Hiiragi Kana

Her Eyes Roll Back As She's Relentlessly Teased, Her Love Juices Dripping As She Cries And Sobs In A Frenzy Of Orgasms - NH Hiiragi Kana

Censored
dsod-066
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

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

Censored
mooc-028
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

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

Censored
mooc-027
I Thought He Was A Tough, Dangerous Type, But It Turns Out He's An Incredibly Shy, Masochistic Cross-dressing Boy♂ - Hanasou Maaya

I Thought He Was A Tough, Dangerous Type, But It Turns Out He's An Incredibly Shy, Masochistic Cross-dressing Boy♂ - Hanasou Maaya

Censored
fem-037
Crossdressing Boys, Complete Feminization Collection 57: Yu Kataoka

Crossdressing Boys, Complete Feminization Collection 57: Yu Kataoka

Censored
hery-173
Japan's First Transsexual AV Director, Himeoka Shia, Directs! Transsexual Lesbian Sex Tape Close-up Date 5 With Ashiro Rio

Japan's First Transsexual AV Director, Himeoka Shia, Directs! Transsexual Lesbian Sex Tape Close-up Date 5 With Ashiro Rio

Censored
tcd-346
A Day In The Life Of Me And My Girlfriend With A Penis, A Taxi Date 8 - Hana Kanade Maya

A Day In The Life Of Me And My Girlfriend With A Penis, A Taxi Date 8 - Hana Kanade Maya

Censored
tcd-347
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!!

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!!

Censored
sal-265
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.

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.

Censored
tpns-037
A Non-hormone-using Cross-dressing Boy ♂, Makoto Kobe, Is An All-rounder Who Can Be Both The Top And The Bottom.

A Non-hormone-using Cross-dressing Boy ♂, Makoto Kobe, Is An All-rounder Who Can Be Both The Top And The Bottom.

Censored
fem-038
Consecutive Orgasms! Full Erection Double Penis Clit Slut Transsexual Reverse 3P Harem! Nanako/Aise Mei

Consecutive Orgasms! Full Erection Double Penis Clit Slut Transsexual Reverse 3P Harem! Nanako/Aise Mei

Censored
nvh-085
As A Crossdresser, My Dick Is Throbbing Today.

As A Crossdresser, My Dick Is Throbbing Today.

Censored
pets-071
[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.

[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.

Censored
dsod-006
Forbidden Incestuous Intercourse With Top-Tier Transgender Women: A Luxurious Drama Collection Of 8 Episodes (4 Hours)

Forbidden Incestuous Intercourse With Top-Tier Transgender Women: A Luxurious Drama Collection Of 8 Episodes (4 Hours)

Censored
husr-306
My And Her (male) Mutual Insertion Life

My And Her (male) Mutual Insertion Life

Uncensored
sdam-178-mosaic
My And Her (male) Mutual Insertion Life

My And Her (male) Mutual Insertion Life

Censored
sdam-178
I'm Going To Be An AV Actress. Shinonome Yuki, A Crossdressing Sex Slave, Makes Her Debut.

I'm Going To Be An AV Actress. Shinonome Yuki, A Crossdressing Sex Slave, Makes Her Debut.

Censored
tanp-055
Crossdresser's Masochistic Orgasm

Crossdresser's Masochistic Orgasm

Censored
timd-041
60 of 115