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First ladyboy experience at what Age?

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  • daveduke007
    Legendary Member
    • Jan 2005
    • 7737

    #106
    Welcome aboard this forum Jet , I dont know the reasons why you have not been back but you dont know what your missing back in LOS
    Your got yer Mother in a whirl
    Shes not sure if your a Boy or a Girl

    Comment

    • alan1chef
      • Jun 2007
      • 1086

      #107
      I made my only other comment on this thread in late January a year ago. I was still a virgin in regard to ladyboys. I was hoping to have my first experience while visiting the Philippines last year...did not happen...too much family stuff going on.

      I am happy to say that thanks to a filipino LB I met up with while she was on vacation here in California, I am no longer a virgin and  had one other experience with another LB who was also visiting California last year.  Enjoyed both experiences. I was 57....never too late to enjoy life.  


      Comment

      • Evan
        Apprentice Member
        • Dec 2019
        • 3

        #108
        First time ladyboy was 39 in spore
        now 45

        Comment

        • Evan
          Apprentice Member
          • Dec 2019
          • 3

          #109
          So far tried ladyboy from Thai, Phil and Indonesia

          Comment

          • WinniePooh
            Aspirant
            • May 2019
            • 88

            #110
            22 I am at least 40+ years older than that now and I still get a boner every time I spot one in the wild and immediately go to hunter mode until I am rejected or rewarded. Doesn't matter where or when.

            Not sure what does it to me? The thrill of the chase? The thought of what I am going to find under those panties? Wondering if this one is going to be a tiger lady so full of lust and femininity that I will hardly be able to ride the wave of sheer lust?
            Last edited by WinniePooh; 12-28-2019, 03:52 AM.

            Comment

            • Escierto
              Senior Member
              • Jun 2020
              • 498

              #111
              My first actual encounter with a transgender woman did not happen until I was in my early 50s and even then it was only online. That led to a decade of soul searching that finally resulted in a week long escapade of mind blowing sex about three years ago when I was 63.

              I think if I had discovered that I like fucking trans women same way I have always fucked genetic women, it would have been easier to deal with. Instead I had to confront how much I wanted the cocks of beautiful women. So now I just accept it and enjoy my life as my girlfriendâ's bottom lol.

              Comment

              • pm2508
                Apprentice Member
                • May 2020
                • 8

                #112
                29 ... and am 32 now .. but she was post op .. i dont think if it counts .. do let me know plzz

                Comment

                • Aaron S. Young
                  Senior Member
                  • Dec 2019
                  • 159

                  #113
                  At the age of 18 I spent time with lady boy this is my first time i booked from Luv escort, and I feel like I was in heaven and I cannot forget it, this is my best memory.

                  Comment

                  • byden
                    Apprentice Member
                    • Jul 2025
                    • 1

                    #114
                    I started watching ladyboy porn when I was 22, but back then it was really hard to find good content. Recently, I began watching on some of the best pay porn sites, and I really liked what I found. The best part is that I no longer need to search elsewhere because these sites update their lists daily with fresh videos if you want to enjoy this stuff then look at http://www.best10pornsites.com/

                    Comment

                    • Escierto
                      Senior Member
                      • Jun 2020
                      • 498

                      #115
                      Here in Makati with my honey. First, I sucked her after we came back from dinner. Then later in the night after we had been asleep, we woke and she fucked me as though it was a dream. A very good night indeed.

                      Comment

                      • Rockheart
                        El Guapo
                        • Jul 2014
                        • 5273

                        #116
                        Originally posted by Escierto
                        Here in Makati with my honey. First, I sucked her after we came back from dinner. Then later in the night after we had been asleep, we woke and she fucked me as though it was a dream. A very good night indeed.
                        You scoundrel!
                        www.ladyboysthai.com

                        Comment

                        • Escierto
                          Senior Member
                          • Jun 2020
                          • 498

                          #117
                          Originally posted by Rockheart

                          You scoundrel!
                          I laughed. Yeah!

                          Comment

                          • Escierto
                            Senior Member
                            • Jun 2020
                            • 498

                            #118
                            I created a monster lol. All she wants to do is face fuck me and cum down my throat. Good thing she has sweet tasting cum.

                            Comment

                            • Jockadam
                              Apprentice Member
                              • Jul 2025
                              • 2

                              #119
                              Will never forget the effect of seeing some tranny porn in a girly magazine when I was pre-pubescent. 10 years later I walked past a few trannies/ladyboys on the streets off of Ermita in 1992 (notorious red-light district in Manila) and had a powerful physical reaction, overcome w horniness! It frightened the hell out of me.
                              As life would have it, at 34 I was on holiday with my girlfriend in Phuket when I finally succumbed and banged the hell out of a gorgeous post op only the sly. As luck would have it, got home, and my girlfriend was preggers so I spent the next 20 years wacking off to lb porn and seeing one or two girls each year. Finally, I am single again, late 50s and just had the filthiest few weeks in BKK and Pattaya. Will return in a few months to live and will be making up for lost time!

                              Comment

                              • Rockheart
                                El Guapo
                                • Jul 2014
                                • 5273

                                #120
                                Originally posted by Jockadam
                                Will never forget the effect of seeing some tranny porn in a girly magazine when I was pre-pubescent. 10 years later I walked past a few trannies/ladyboys on the streets off of Ermita in 1992 (notorious red-light district in Manila) and had a powerful physical reaction, overcome w horniness! It frightened the hell out of me.
                                As life would have it, at 34 I was on holiday with my girlfriend in Phuket when I finally succumbed and banged the hell out of a gorgeous post op only the sly. As luck would have it, got home, and my girlfriend was preggers so I spent the next 20 years wacking off to lb porn and seeing one or two girls each year. Finally, I am single again, late 50s and just had the filthiest few weeks in BKK and Pattaya. Will return in a few months to live and will be making up for lost time!
                                Sounds like you have a plan. Hope to hear about your adventures making up for lost time!
                                www.ladyboysthai.com

                                Comment

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