Ivory Mayhem Pecan Gap

Cast: Jade Venus, Natalie Stone
Genres: Male on Shemale, Shemale on Male, Hardcore, Anal
Video language: English
Jade Venus, Natalie Stone  is here. She might like a woman, but she fucks just like a man, because this chick got dick! So get your sperm enough smoking hot transsexual cock.
Format: mp4
Duration: 27:50
Video: 3840x2160, AVC (H.264), 7033kbps
Audio: 132kbps



File size: 1.4 GB


DOWNLOAD FROM FILESMONSTER: Ivory Mayhem

Author signature

Nathy Vaqua - Ms.Vaqua is Feeling Herself Edgard

Video language: English
Folks today we bring to you this sexy blonde little cutie showing us some self-loving action. There's one thing we can all agree here at Trans500. It's that when it comes to definite jerk-off skills, Nathy Vaqua has 'em. Don't let her shy demeanor fool you. This one's a full out freak. She stuffs her ass as if it's her last time having that dildo in her hand. Now as we say here at Trans500. "Let's get right to the fucking action!"
Format: mp4
Duration: 26:22
Video: 1920x1080, AVC (H.264), 4878kbps
Audio: 184kbps



File size: 978.8 MB


DOWNLOAD FROM FILESMONSTER: Nathy Vaqua - Ms.Vaqua is Feeling Herself

Author signature

Trans-Ference Pt.2 Sc.1 Bernardston

Cast:  Brittney Kade, Cherry Mavrick, Kasey Kei, Lena Moon, Eric John, Johnny B, Micah Martinez, Michael Del Ray
Genres: Anal, Asian, Big Boobs, Big Cock, Big Dick, Big Tits, Blonde, Blowjob, Brunette, Cum Swallow, Cumshot, Deepthroat, Doggystyle, Face Sitting, Fishnets, Handjob, Hardcore, Interracial, Lingerie, Male Fucks Trans, Missionary, Open Mouth Facia
Video language: English
These trannies are born to be wild! And these T-girls have big tits, huge cocks and an insatiable appetite for hardcore sex! Watch them suck and fuck each other before they take turns splooging on themselves and each other! There's plenty of hot scenes and plenty of tranny action going on here!
Format: mp4
Duration: 29:06
Video: 3840x2160, AVC (H.264), 14647kbps
Audio: 125kbps



File size: 3.1 GB


DOWNLOAD FROM FILESMONSTER: Trans-Ference Pt.2 Sc.1

Author signature

Yenny - Late Night Pillow Talk Mazarron

Video language: English
It's that solo time again. Don't you just love watching your favorite TS go at it all on her own? We know we do. Watching her stroke her cock until she bursts is simply intoxicating. Today we have the gorgeous Yenny making her debut with one of the ultimate jerking scenes to date. She feels extra comfortable rubbing herself against her pillows. Those are some lucky pillows indeed. Sit back, relax and enjoy lovely Yenny in "Late Night Pillow Talk"
Format: mp4
Duration: 24:41
Video: 1920x1080, AVC (H.264), 9762kbps
Audio: 184kbps



File size: 1.8 GB


DOWNLOAD FROM FILESMONSTER: Yenny - Late Night Pillow Talk

Author signature

LadyBoyGold Jasmine  Juicy Ass Red Devil Big Cum Top Farber

Release Year: 2015
Studio: LadyBoyGold
Cast: Jasmine
Genres: Ladyboy, Transsexual, Hardcore, Anal, Blowjob, Bareback
Jasmine's beautiful round ass is divine. If there's a heaven would imagine the entrance would look similar with to those smooth chocolate buns, thick thighs and clean winker. That ass is...
Format: mp4
Duration: 37:35
Video: 1280x720, AVC (H.264), 1663kbps
Audio: 156kbps

File size: 502.3 MB


DOWNLOAD FROM FILESMONSTER: LadyBoyGold Jasmine  Juicy Ass Red Devil Big Cum Top

Author signature

Trans-Ference Pt.2 Sc.4 Sangerville

Cast:  Brittney Kade, Cherry Mavrick, Kasey Kei, Lena Moon, Eric John, Johnny B, Micah Martinez, Michael Del Ray
Genres: Anal, Asian, Big Boobs, Big Cock, Big Dick, Big Tits, Blonde, Blowjob, Brunette, Cum Swallow, Cumshot, Deepthroat, Doggystyle, Face Sitting, Fishnets, Handjob, Hardcore, Interracial, Lingerie, Male Fucks Trans, Missionary, Open Mouth Facia
Video language: English
Beautiful as women with huge tools ready to drill. The charming and sexy Beatrice in a hot encounter with her slave who will take you to the maximum of pleasure. He is already waiting for her very excited ready and eager to take it all and suck it.
Format: mp4
Duration: 28:39
Video: 3840x2160, AVC (H.264), 14655kbps
Audio: 125kbps



File size: 3.0 GB


DOWNLOAD FROM FILESMONSTER: Trans-Ference Pt.2 Sc.4

Author signature

Crossdressing Girlfriends Get Down On A Big Dick - Full HD 1080p Cooksville

Cast: Amanda Becker and Joanna Queen
Joanna and Amanda are crossdressing girlfriends who live the life more and more with each passing day. They met and have fallen in love...not just with each other but with sharing a big dick together too!
Format: mp4
Duration: 15:57
Video: 1920x1080, AVC (H.264), 7806kbps
Audio: 229kbps



File size: 939.1 MB


DOWNLOAD FROM FILESMONSTER: Crossdressing Girlfriends Get Down On A Big Dick - Full HD 1080p

Author signature

Trans Gamer Chick Gets Fucked By A Boomer Lignano

Release Year: 2022
Cast: Raven Gray
Genres: Shemale, Hardcore, Blowjob, Anal, Bareback
Video language: English
Raven Gray is a trans gamer chick that is helping her boomer friend play a video game on his phone. She is a very horny girl of course and soon she is grabbing at his package and taking his mind completely off the game!
Format: mp4
Duration: 25:10
Video: 1920x1080, AVC (H.264), 7815kbps
Audio: 231kbps



File size: 1.4 GB


DOWNLOAD FROM FILESMONSTER: Trans Gamer Chick Gets Fucked By A Boomer

Author signature

Seducing The Coach Is Too Easy Mount Dora

Release Year: 2022
Cast: Ava Holt
Genres: Shemale Hardcore, Blowjob, Anal, Bareback
Video language: English
Right after the Coach is done screaming at one of his players for his attitude on a road trip, someone knocks on his hotel room door.
Format: mp4
Duration: 27:37
Video: 1920x1080, AVC (H.264), 7795kbps
Audio: 236kbps



File size: 1.6 GB


DOWNLOAD FROM FILESMONSTER: Seducing The Coach Is Too Easy

Author signature

Thais Anderson - Thais Anderson North Ferrisburg

Video language: English
If anyone has an experience that we can share commonly, that is to have great steamy sex with this beauty named Thais Anderson. Our macho this time didnt have any problems and locating this babe in the streets of Barcelona and after the typical chit chat, they went straight to business. After some touching and good dick sucking that Thais did to our boy, he shoves that hard rock cock all up in this babe.
Format: mp4
Duration: 23:52
Video: 1280x720, AVC (H.264), 2142kbps
Audio: 184kbps



File size: 408.0 MB


DOWNLOAD FROM FILESMONSTER: Thais Anderson - Thais Anderson

Author signature

Jenny Kennedy - Always There When Daddy Needs Her Williamsfield

Release Year: 2021
Genres: Shemale, Hardcore, Blowjob, Anal, Bareback
Video language: English
When Daddy wants her, Jenny Kennedy is always there for him. She is fully feminized and ready to get on her knees and suck cock.
Format: mp4
Duration: 27:24
Video: 1920x1080, AVC (H.264), 7809kbps
Audio: 223kbps



File size: 1.6 GB


DOWNLOAD FROM FILESMONSTER: Jenny Kennedy - Always There When Daddy Needs Her

Author signature

Melanie Brooks - Interracial Barebacking Dos Rios

Video language: English
Our veteran star Sean Michaels is back and ready to throw down some cock on Melanie Brooks in this interracial bareback scene. That slim body and cute face, we know we're excited. That sexy little black dress gets peeled off and ready for some lovin'. That penetration is fire! Let's get it started folks. Sean Michaels along with Melanie Brooks in "Interracial Barebacking"
Format: mp4
Duration: 33:14
Video: 1920x1080, AVC (H.264), 14649kbps
Audio: 309kbps



File size: 3.6 GB


DOWNLOAD FROM FILESMONSTER: Melanie Brooks - Interracial Barebacking

Author signature

Wendy Williams Gilcrest

Video language: English
Wendy Williams is considered a pioneer in the Transsexual adult genre. She has paved the way for many and is currently the most rewarded transsexual star in the business winning in all of the major award ceremonies. It was only right that we put her at the top of our list of targets we had to have appear on trans500. The way this plays out is I called Wendy and told her I was coming to Vegas and was interested in shooting with her but the catch was I could not reveal to her who her partner for the scene would be . Luckily she agreed and off to Vegas we went . Our scene starts out with a little tease from Wendy and then she spends a bit of time preparing and loosening up her tight ass with a toy .. Knock Knock .. Whose There? Its Fucking Ramon!!! Ramon's in tha house and hes got one thing on his mind. Hardcore, ass pounding action at its best!! He tears that tranny ass like he's known to do around these parts. When Ramon comes out to play, you know there's no telling what may happen to the target at hand. Watch Wendy Williams lay down and get stuffed with that Monster of a Cock. Simply one of our best hardcore ass pounding scenes! Enough talking, let the mouth stuffing, cock-slurping and anal destruction begin with Wendy Williams in "Wendy Meets the Monster"
Format: mp4
Duration: 26:15
Video: 1280x720, AVC (H.264), 2142kbps
Audio: 184kbps



File size: 448.4 MB


DOWNLOAD FROM FILESMONSTER: Wendy Williams

Author signature

Transgressivefilms - Learnbydoing Benson

Release Year: 2022
Studio: Transgressivefilms
Cast: Joel Someone, Zerella Skies, Kasey Kei
Genres: Threesome, Anal, Natural Tits, Small Tits, Fingering, Teen, 69, Old Young, Asian, Facesitting, Interracial, Pussy to mouth, Blowjob, Deepthroat, Cumshot, Cum swallow, Cum in Mouth, Big Dick, Gagging, Student, Teacher, Cum Swap, Face Fucking, Ebony, Bubble
Video language: English
Principal Walker (Joel Someone) is busy in his office when a student, Charlotte (Zerella Skies) asks to speak with him for a moment. Principal Walker welcomes her in with a smile and offers her his full attention. Principal Walker respects Charlotte, her being student president and a straight-A student. She's a natural leader, and Principal Walker is glad to give such a model student the time of day.
Charlotte tells Principal Walker what's on her mind. She has come here today to criticize a rule where teachers are not able to discuss trans/+ topics with students. She recounts a recent experience where her sex-ed teacher appeared unable to discuss these issues with her class, even though there was a student who was dating a trans person from another school and could have used some information on the topic. Charlotte recounts how after the class' encouragement, the teacher opened up and even shared aspects of her trans journey. All the students felt more empowered because of it.
As Charlotte speaks, she doesn't notice Principal Walker grow more and more agitated. Whatever calm and welcoming demeanor he had at the start of this discussion evaporates with every word Charlotte utters. When Charlotte reveals a signed petition against the rule in question that she wants Principal Walker to bring to the school board, he dismisses it. Instead, he calls Ms. Peters, Charlotte's sex-ed teacher, to his office with the intent to discipline her. Charlotte is devastated, realizing her plan may have caused more harm than good.
Charlotte begs Principal Walker to reconsider- the thing she wanted to do was put Ms. Peters' job on the line. But when Ms. Peters (Kasey Kei) arrives, Principal Walker announces that he must report her to the school board for breaking protocol. Ms. Peters won't go down without a fight, however, and she enters into a tense debate with Principal Walker about trans rights. Although Principal Walker claims he is powerless to bend the rules, Ms. Peters wins him over, convincing him to reexamine the rules, and himself.
When a hidden attraction between him and Ms. Peters is revealed, Charlotte motivates them to consider getting to know each other a little more 'closely'. Principal Walker seems willing, but is hesitant since he wouldn't know the first thing about trans sex. Ms. Peters, however, is happy to guide Principal Walker through his first trans sexual experience. Though he is nervous, Principal Walker agrees. They have foreplay, with Charlotte guiding Principal Walker in his first blowjob and then joining in for a threesome. Principal Walker's insecurities vanish into thin air as he dives into new sexual territory with gusto. As they say, sometimes the best way to learn is by doing.
Format: mp4
Duration: 47:27
Video: 1920x1080, AVC (H.264), 4938kbps
Audio: 187kbps



File size: 1.7 GB


DOWNLOAD FROM FILESMONSTER: Transgressivefilms - Learnbydoing

Author signature