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Hungry For Me Bareback

LadyboyObsession episode 114 with Ning. To be 100% fair, I think Ning kind of looks like a dude nowadays, or to be 110% honest, she always kind of looked like a dude to me. But she had been on my wish list for ages. She was one of the few ladyboys that stayed active on Planetromeo or Gayromeo back in the day, actually active is quite a big word as she logged on maybe once every month, but anyway, I had seen her profile pics of her standing outside in body stockings and those photos were amazing. When she finally answered one of my messages we met for a porn session a day later, at first I though, man, what an ugly girl, but then I was like, man, what a sexy boy. The queer in me really lights up whenever I am with her, but I am always really into her or not into her at all which makes it a it more difficult to plan anything with her, but for this video, I had nothing planned, I just contacted her when I felt like a bit on Ning and we had a great time.

Released: October 1, 2023

    User Rating   5.00

Shibari Tied Erect For Bareback

LadyboyObsession episode 113 with Nonny a.k.a. Mi-cha. Personally I rather love JAV. The creativity in kink they bring to the table, it's pretty good when it's good. Their bondage movies are quite fascinating, I would love to have the opportunity to create a space where I could play torture ladyboys and do all the kinky stuff I see in Japan. Unfortunately, we got to be a bit more on the download and ready to bolt in the rest of Asia. But a little shibari from time time is manageable me thinks. I need more practice, I'll be the first to admit it, but this one is for those who like BDSM JAV movies as well.

Released: September 15, 2023

    User Rating   5.00

Pole Dance Pet In Out Buttfucking

LadyboyObsession episode 112 with Nadia. Few things are better than watching a young sexy girl dancing at a strip joint. Something that makes it better is if you're the only ones there and you don't have to compete for eye contact with any of the other guys left and right. The one thing to kick it to the next level after that? A young girl that has a nice meat stick dangling between her legs. This is of course not something you see every day, thankfully there is a place for perverts like myself. I recorded a video to show you what I'm talking about in my pointless intro. Enjoy the beautiful amazon Nadia in her new video.

Released: September 1, 2023

    User Rating   5.00

Lets Go Outside Wet Bareback

LadyboyObsession episode 111 with Premmie a.k.a. Prem. Some ladyboys are just plain old cuter than others, Premmie is in a league of her own, she is nerdy, extremely pretty with dramatic large eyes, she has natural hormone tits, the cutest smile, I could go on forever. She is one of three to five ladyboys I get excited over even when they have short, more boyish haircuts. The only small downside to Premmie is that she is a bit too tall for my liking, I don't mind tall ladyboys but then I prefer them to be much taller and stronger and a bit more masculine so they can wrestle with me and try to overpower me, that's good fun, but hard to film on your own. But back to Premmie, her angelic looks are illegally cute when she makes porn videos, though she looks and acts like an angel.. she actually is one. Premmie loves sex a lot though, maybe that's the one one thing that doesn't allow direct access into heaven, she basically cannot cum unless something is inside her ass so that's a bit of intel for you in case you ever meet her.

Released: August 15, 2023

    User Rating   5.00

Simultaneous Climax Hardcore

LadyboyObsession episode 110 with Peach. I don't know what it was, but I honestly fell in love with Peach the moment she stepped into the room, such a cute, friendly and warm face, unlike a large number of ladyboys in SE Asia, she did not look like someone who likes to engage in forbidden substances too often. Peach is a bit plumb and her boobs look very feminine and realistic, they look, maybe, even more natural than even Pam's pretty orbs. So maybe it was Peach's natural and healthy looking body, maybe it was the cute pink color of lipstick, maybe it was the pretty eye shade make up, I don't know, but she was just smashing, see it for yourself only on LadyboyObsession.

Released: August 1, 2023

    User Rating   5.00

Bubble Bathe with Me CIM

LadyboyObsession episode 102 with Nonny. The danger of being in Asia, more so than being at home in my regular routines. That at any given moment some lovely girl you spent time with before messages you with a picture that makes it very hard to get back to doing what you were doing, that is ok, but the problem is, my hard earned dollar bills evaporate like water on the skin while on the beach. I wish Covid would evaporate this fast I swear, but back to the other danger, so when someone like Mi-Cha drops a pic of her looking into the camera while licking a finger and other finger stuck in her little butthole accompanied by the text her hands are filthy and need to bathe and whether or not I'd like to get a room and pay for that bath, well, I'd have to say yes!

Released: December 27, 2022

    User Rating   5.00

Goth Rebel Stuffed Sprayed

LadyboyObsession episode 101 with Namwarn. Namwarn is kind of unique girl to me, some moments she looks rough as shit, but other moments she is as charming as they come, she's like a chameleon that changes her looks according to her mood. But one thing that never fails is her skinny body and her A'ber tight little hole. Sometimes it's like it'll bite my little snake straight off I swear. If only she's allow me to enter her without that discomfort and irritated skin condoms present when things are too tight, things would be a whole lot more pleasant for both of us, or at least for me, I don't really care if her little butthole hurts, to be totally honest, I love how her face expresses the pain when I fuck her cute little behind.

Released: November 29, 2022

    User Rating   5.00

Purple Bodystocking Deep Anal

LadyboyObsession episode 100 with Pepper. Pepper and her hypnotizingly cute face and seductive body are back for another video today. She is just so perfect, what a find she was, I am forever thankful to her friends who introduced her to me. Today she wears a purple body suit but of course, she picked one with an open crotch, she knows exactly where I'd like to stick my dick in so she kept it easily accessible. First she sucks me with her wonderful pierced tongue and then we move on to her tiny ass. Although she trains hard to take thicker than what she is used to things up her little stinky hole, she still has a long way to, she still suffers when taking it, she loves the idea of being fucked though so she keeps coming back for more. We'll get there eventually, I'll make sure to get her back often and make video diaries of our sessions for anyone who like me, cannot get enough of this beauty.

Released: November 1, 2022

    User Rating   5.00

Go For Round 2 Anal Training

LadyboyObsession episode 99 with Tanya. Tanya had met up with me the day before to do her first ever porn shoot but because it was her first time taking a white dick up her ass and she was excited, the pain she experienced took away some of the fun. She contacted me the next day saying she wanted to try again, I told her that her ass needed some training first maybe and once she was used to taking bigger things up her tiny pooper she should come back to see me. But that advice fell on deaf ears, she texted me to be ready for her in about an hour. Watch round two right here.

Released: October 4, 2022

    User Rating   5.00

Hello Cutie Hairy Cock Hole XXX

LadyboyObsession episode 108 with Nadia. Yes, I admit it, I am a sucker for tall skinny ladyboys with thick lips and beautiful shiny hair, then if they wear things that are usually meant for younger audiences it makes them so extremely naughty because they know full well how provocative they look when wearing innocent clothes. Nadia is one of the prettiest faces I have seen in a very long time. I always try to monitor the scenes for prospects as much as I can so I have the chance to record videos with both before and after surgery looks, unfortunately I missed my chance with Nadia but what does it matter anyway. She can't possible have looked cuter than she already does. Watch this rare beauty being a very bad girl on LadyboyObsession.

Released: June 13, 2023

    User Rating   5.00

Red Hot Bareback Debut

LadyboyObsession episode 107 with Patty. I had been trying to get Patty to make porn with me for a while, she had caught my attention when I walked by and she got me to enter the venue she was working for and I knew straight away she'd be hot in porn videos. She would giggle every time I asked her and we talked about it several times and I patiently waited for her to make a decision and finally she agreed to do it. When she showed up I nearly jazzed my pants, she always has this dirty grin on her cheeky face and for the occasion she had bought a new outfit that reminded me of that show that used to be aired that showed lifeguards working on the beach wearing red bathing suits, I used to love that show for exactly that, fit women in red bathing suits running around the beach. Did she somehow see straight through me or perhaps I'm not the only perv who liked that show and she found out about this another way? Anyway, she was such a turn on, it was already an accomplishment not to bust a nut when she walked in with her stilettos clanking the floor but I couldn't help but to cum prematurely with such a naughty girl on my dick in her first ever porn shoot and bareback at that. This screams for an encore and I promise it will happen.

Released: May 16, 2023

    User Rating   5.00

Gaping Obsession Casting

LadyboyObsession episode 106 with Nadine. I was hanging around in an area with lots of colleges and therefore even more coffeeshops to have some tea as they wouldn't sell me any spirits. And I noticed the large groups of students walk by after finishing their classes. Some of them came in to the shop and among them I saw Nadine, whom I had talked to a couple of times after she was introduced by one of her friends. She acknowledged my presence with a little smile and a nod but didn't come near me. Fair enough, what would her friends say? So after I finished my drink I up and left and went back home. On the way I received a text from her asking me whether or not I really made porn videos like her friend claimed. I told her sorry and yes, then she asked me if I wanted to make a tape with her as well. You know the answer as you're reading this obviously, watch her very first porn video ever only here.

Released: April 18, 2023

    User Rating   5.00

Cuffed Sleepover Bareback Facial

LadyboyObsession episode 105 with Pop. Cute petite Pop had just turned eighteen when we first met, she had a couple of friends who were a few years older than her and she knew they had been making porn videos and she had been wanting to follow her friends but just had to wait. So a few weeks after her birthday I was back in town and she got her wish. In this video she was dressed up in her pajamas, she wanted to play out a sleep over fantasy and I thought that was a great idea. See Pop in hardcore action only on this channel.

Released: March 21, 2023

    User Rating   5.00

Fluffy Stockings Big Cock Bareback

LadyboyObsession episode 104 with Pooh. Today we have Pooh back for another video, me and her go back a long time, I don't mean as in we're close friends, but I do mean when it comes to making porn videos we go back a long time. Nowadays there are few ladyboy admirers that haven't seen her, if you google big dicks and ladyboys she is bound to show up. All that is great, but it has been getting more difficult to meet her, but you know me, I don't give up easily, I know there are many people including myself who like to see her play so I just kept trying and at least I secured another video with her for you all to see. Please enjoy her new scene only here.

Released: February 21, 2023

    User Rating   5.00

Lovely in Pink Willowy Buttfuck

LadyboyObsession episode 103 with Pepper. Pepper is back for another video today, as if she wasn't feminine and seductive on her won already she decided to wear a white leather collar and cute pink stockings. This girl is so unbelievably sexy with her perfect silky hair and her pierced tongue. She really knows how to drive a man wild when she gives head. She hadn't been on hormones for a while so her cock was hard virtually the whole way through, watch pink hot Pepper in her new video only on LadyboyObsession.

Released: January 24, 2023

    User Rating   5.00