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  #51  
Old 09-12-2014
michneo michneo is offline
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Victoria aka Miriam
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  #52  
Old 09-13-2014
Pastorn Pastorn is offline
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Quote:
Originally Posted by 13spaceman View Post
Kimber James for me. Before she had the surgery. Still a hottie. Never will forget my first crush
Totally agree!!
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  #53  
Old 09-13-2014
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Mine was Long Mint but seeing so many on here,
elsewhere everything is now a blur of cock\cum and ass!
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  #54  
Old 10-24-2014
omni omni is offline
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Quote:
Originally Posted by 13spaceman View Post
Kimber James for me. Before she had the surgery. Still a hottie. Never will forget my first crush
Dayum

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  #55  
Old 11-01-2014
siennagrace69 siennagrace69 is offline
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Long ago----Julie Bond
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  #56  
Old 11-13-2014
luis raccuglia luis raccuglia is offline
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Default Areeya & Longmint

I love Areeya's body, boobs, tight ass, beautiful cock that I would love to suck and get it real hard in my wet mouth, even taste her cum in my mouth or feel it in my ass, love to kiss Areeya georgeous mouth, wow

Longmint is another georgeous ladyboy I love , love to taste that massive cock and love to fuck that sweet tight hot ass till I cream up all my over that ass
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  #57  
Old 11-14-2014
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Yasmin Lee
I saw her in Joey Silvera's Road Trip 11 and fell in love. Her beautiful , exotic Asian features, those long legs and that beautiful big cock. I am still in awe of her.
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  #58  
Old 11-22-2014
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Default Sulka was the best!

I fell in love with Sulka - she was the first actual person. But there was someone before her. I had not experienced my first orgasm yet, but I began to have fantasies about women who had cocks. The thought of looking up at a beautiful face framed by two lovely breasts as I sucked her cock - well, that was incredibly exciting. Keep in mind, I hadn't started masterbating yet. Then I got the 'bad news' from another kid that women with cocks was an impossibility - and there went my fantasy. Years later, I saw a porn advertisement in a magazine. It was Sulka being sucked by some lucky guy. These were the days when they were still censoring pictures, so there was a black dot pasted over the lips/cock contact point. But Sulka was so hot! Her cock was big and hard, her breasts full, and she had such beautiful red hair framing a face with gorgeous lips and eyes. I have never seen that picture again, but it lives in my memory.
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  #59  
Old 11-23-2014
slimjimviking slimjimviking is offline
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Quote:
Originally Posted by petty adams View Post
Pls post a picture also.
Kimber James, found her by accident been fapping to shemales ever since
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  #60  
Old 11-27-2014
malaysia malaysia is offline
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my first was with filippino ladyboy. Her cock was hard to erect due to taking hormone. I suck so hard but only made it partially erected. I want she do fuck me but fail to do it...
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  #61  
Old 01-04-2015
bigbonz88 bigbonz88 is offline
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Bailey Jay in Line Trap. Had to buy it after seeing the infamous toothbrush GIF
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  #62  
Old 01-11-2015
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Going back to my early teens over a decade ago it was for sure Barbie Woods. This photo actually was the one that let me know I truly was a boy attracted to trans girls. I am still a big fan of Barbie's.
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  #63  
Old 01-11-2015
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Default Barbara Verissimo

I was a big fan of Sunshine Films in the 90s. Barbara was one of my favorites... her ass is/was AMAZING!
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  #64  
Old 01-26-2015
lmc lmc is offline
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Miriam rivera. Back in 2000.. beautiful
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  #65  
Old 03-14-2015
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ladyboy moo
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  #66  
Old 03-14-2015
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Quote:
Originally Posted by izzanod View Post
I would have to say mine is Bailey Jay
I'll second that Click image to open a larger version of 2curious01-o61ez-75b0cc.jpg. Views: 13.
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  #67  
Old 03-16-2015
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First tgirl i jerked off to was helen, my first crush was mint
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  #68  
Old 02-28-2016
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Quote:
Originally Posted by rabeche View Post
First tgirl i jerked off to was helen, my first crush was mint
Asian boys in porn got short penises, i dont know why so many asian shemales got that big.
There's no way to make penis grow, as we know, even so for any reason cumshots are usually long distance shots cmpared to a man, always according to porn i've seen.
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  #69  
Old 02-29-2016
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Default There were a lot but this one was my first

she was my first
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  #70  
Old 03-02-2016
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ARIES666 ARIES666 is offline
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Was fascinated by both Candy and Sulka when I first saw photos of them in the 1980's (or was it 70's?). But my first real "crush" was for Pasha when I stumbled upon her photos a few weeks later. At that time (late 70's to the 80's) I thought that Pasha and Shannon were the most feminine T-Girls I had seen. They could have fooled the biggest homophobic red-necked muscle-headed guys with no problem.
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TS Pasha 01.jpg   TS Pasha 02.jpg   TS Pasha 03.jpg  

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Last edited by ARIES666; 03-02-2016 at 11:22 AM.
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  #71  
Old 03-12-2016
barrell barrell is offline
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has to be Caroline Cossey for me , i was mesmerised by her pure beauty
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  #72  
Old 01-18-2024
luis raccuglia luis raccuglia is offline
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Default Areeya my first crush

Quote:
Originally Posted by LadyboyJerker View Post
That's gotta be Areeya.
I remember the exact scene.
Areeya's World - Persian Queen or something like that.
Andc of course, the pictures.
I should get some free time to watch it again, for the nostalgia and the hard-on.
When I saw photos and videos of Areeya, I just automatically had a massive crush, it was the most gorgeous perfect ladyboy I ever laid eyes on, wow :heart
:
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  #73  
Old 4 Weeks Ago
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Default El Bimbo

Must be 50 years ago.
CD in the Red Light District of Amsterdam.
Little South American girl.
So sweet and beautiful modest.
Even now a can get off seeing it.
The quality of the movie is antique.
But who cares ....
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  #74  
Old 3 Weeks Ago
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EdwardSinclair EdwardSinclair is offline
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Default Camila Saenz and Miriam Rivera.

First ever that I remember is the Argentinian Camila Saenz.

https://www.ashemaletube.com/model/camila-saenz-413/

As far as I was concerned I saw her as a cis girl, because when I was smitten by her I did not even know what a trans was, and I did not know she was one. She truly opened my mind to a whole new world of sexuality.

The other one is Miriam Rivera, which makes me sad to this day, to lose such an angel. She was without a doubt one of the most magnetic and charming people you could ever meet.

They have a documentary about her on channel 4 right now actually:

https://www.independent.co.uk/arts-e...-b2535485.html
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