my one and only enconter with a ladyboy

I want to talk about the filthiest and most erotic experience I have ever had…and it just so happens it was my first and only time with a shemale! I have always ben a horny guy, masturbating a lot and sex but always with/over girls. However I first played with my ass when I was about 18 and I remember the feeling when I managed to get a but plug all the way inside me. Even though this was fun I could never enjoy it fully. I got into shemales through porn, I love anal play and the older and more sexual I got I realised there was a fantasy I had, to be fucked by a cock but it had to be a pretty lady boy doing it! I travelled europe a year ago and the first stop was amsterdam. After walking around the RLD and smoking drinking and generally being high and horny, I found Blooedstraat which is a LB area. I was instantly aroused as I saw the selection of shemales holding their dicks and giving me the eye so I came back later for another look (about 3am) whilst i was away i was thinking if i really wanted to do it and i so, i knew it would have to be special because it was going to be a one off secret. the shemale i chose was from brazil and called Regina. she was gorgeous, curvaceous and had incredible eyes. she told me she had an 8 inch cock and i entered the door… I tolg regina it was my first time and that i wanted it to be pefect. i said i wanted to be treayed like a bitch, made to suck her cock and fucked. immediately she pushed my head doen to her cock and made me suck it . it was hard aready and so big, i am an average 6inches but her cock was big, thick and nice looking! i tried to suck the best i could as i was really enjoying being treated like her bitch. this was helped by the fact her cock was bigger than mine and that i had never put anything as big into my ass before she bent me over and lubed up my ass, all the while talking dirty to me about how she was going to push her thick shaft inside me. she loosened me up surprisingly quick with 1,2 then 3 fingers, telling me not to worry and that she knew what she was doing. i loved being the one to bend over with my ass in the air and no control. she was so gorgeous damn! i felt completeley at her mercy. she gripped my buttocks and forced her dick in as i groaned. she got into a rhythm and pushed deeper and deeper in side me, spanking my ass and telling me i was her little bitch in her soft, portugese accent. after about 10 minutes of this i pushed her back and asked her of i could rider her. she smiled and lay vback with her dick in her hand. i masturbated a little as we kissed and i sucked on her big breasts. i licked her brown skin and then slowly lowered myself onto her. it was incredible, i found myself riding her harder and harder, groping her tits and moaning like i have never moaned before. i realise my ass was really being fucked hard for the first time and i lo ved it. i kept riding her hard until she told me to slow down. my ticht virgin ass was making her come. i leant in and reminded her that she was the first person to ever enter me and she grinned and kissed me. we fucked like ths for a long time, i was aware my time was up but she was enjoying it and so was i. after she came again we went into spoons position. she was fingering me still, really hard with 3 fingers and i sucked her small balls and licked her beautifull asshole. i felt ike suck a whore, a distgusting filthy whore and it was my dirty secret. my ass got sore and i asked if i could return the favour. she oulled her legs up by her head and allowed me to lick her ass furiously until i was hard enough. we fucked and then i pounded her big ass doggystyle until i came. i wanted to fuck her hard because she had done the same to me all in all i was in her room for over an hour, when it was to be a 30min session. i walked out feeling amazing, my ass was so sore but i couldnt believe i had done it and enjoyed it! now i think about it more and more, find myself sneaking off to wank to shemale poen and am considering another trip back to the dam to indulge my fantasies. i would like to have 2 at once, maybe we will see one day! i hope you enjoyed my story, i just felt like i had to tell someone!

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my one and only enconter with a ladyboy, 8.7 out of 10 based on 3 ratings

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  1. MasterHank says:

    Pretty good story, I hope you follow up with more TRy to add more detail to really help everyone get harder Maybe your next experience with a ladyboy will develop into your threesome with the ladyboy’s dom boyfriend

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