Questions for those who admire transgender women

[Escierto]

I was going to title this thread “Questions for the tranny chasers” since it is an existing expression with a very specific meaning. However I hate the word tranny as well as the whole expression itself, so I thought, NOPE. Anyway, onwards!

One can’t help but notice the number of threads with pics of transgender women and the popularity of this topic. This should come as no surprise since transgender porn is extremely popular.

These threads elicit many comments from admirers of transgender women hoping that somehow in some unspecified way, their desires for these women will be fulfilled.

My question is this: what, if anything, are you doing to realize these dreams? If not, why not? Do any of you actually contemplate a relationship with a transgender woman?

 

[BiDrew42]

I have had sex with hundreds of trans women dating back to the early 80's. My first was an escort that I picked out of a swinger's magazine called "Unique Encounters" that I found at an adult bookstore in North Miami Beach. I had been sucking cocks through a gloryhole while watching trans porn and was really turned on by the thought of a beautiful, sexy, feminine woman with a cock. After that first experience, I was hooked. I had sex with dozens more trans escorts and prostitutes over the next couple of years. I took a twenty year break from trans women (and everyone else) during my marriage, but I fantasized about them often. After my divorce, I spent a week in Brazil, having sex with as many trans escorts and prostitutes as possible, followed by a week in Bangkok where I developed a lifelong obsession with Ladyboys. I went back to Brazil (Rio and Sao Paulo, mostly) and Thailand (Bangkok, Pattaya, and Phuket) every year for the next five years. My work also required frequent business trips, and I had sex with trans escorts in most of the major cities in the U.S., and various countries in Central and South America and the Caribbean.

I have had two long-term relationships with trans women, the first lasting just over a year, and my current relationship which has been ongoing since I moved to Sydney, Australia in April, 2015. I travelled all over Asia for my job during my first five years living in Oz, and I hooked up with trans escorts nearly everywhere I went. Covid cut out the travel for two years, but I'm gradually getting back to the frequency of travel I was doing pre-Covid. I plan to retire in three or four years, and will be moving to Thailand when I do. I recently purchased a condominium in Bangkok, and I also plan to buy a villa somewhere in the vicinity of Pattaya. Thailand is very inexpensive for ex-pats, and there are thousands of Ladyboys to choose from.

 

[Escierto]

I have had sex with hundreds of trans women dating back to the early 80's. My first was an escort that I picked out of a swinger's magazine called "Unique Encounters" that I found at an adult bookstore in North Miami Beach. I had been sucking cocks through a gloryhole while watching trans porn and was really turned on by the thought of a beautiful, sexy, feminine woman with a cock. After that first experience, I was hooked. I had sex with dozens more trans escorts and prostitutes over the next couple of years. I took a twenty year break from trans women (and everyone else) during my marriage, but I fantasized about them often. After my divorce, I spent a week in Brazil, having sex with as many trans escorts and prostitutes as possible, followed by a week in Bangkok where I developed a lifelong obsession with Ladyboys. I went back to Brazil (Rio and Sao Paulo, mostly) and Thailand (Bangkok, Pattaya, and Phuket) every year for the next five years. My work also required frequent business trips, and I had sex with trans escorts in most of the major cities in the U.S., and various countries in Central and South America and the Caribbean.

I have had two long-term relationships with trans women, the first lasting just over a year, and my current relationship which has been ongoing since I moved to Sydney, Australia in April, 2015. I travelled all over Asia for my job during my first five years living in Oz, and I hooked up with trans escorts nearly everywhere I went. Covid cut out the travel for two years, but I'm gradually getting back to the frequency of travel I was doing pre-Covid. I plan to retire in three or four years, and will be moving to Thailand when I do. I recently purchased a condominium in Bangkok, and I also plan to buy a villa somewhere in the vicinity of Pattaya. Thailand is very inexpensive for ex-pats, and there are thousands of Ladyboys to choose from.

Thank you for your detailed response about experiences which I doubt that anyone on this site can match. You are definitely the last person to whom I directed my questions because you have done it - you have chased your fantasies and made them real. So I salute you!

But everyone else - are you satisfied rubbing one out to only fans girls forever?

 

[BenHoping]

Yeah, virtual trans girls are likely to be the extent of things for me. Satisfied though? I'd have to express that in degrees. So on a scale of "miserable and aching for hands-on" to "Damn, can't wait to fire up the laptop and stroke" I'm at about the "I'm a chicken shit, this is the best I can do" stage.

 

[2tallpaul]

Thank you for your detailed response about experiences which I doubt that anyone on this site can match. You are definitely the last person to whom I directed my questions because you have done it - you have chased your fantasies and made them real. So I salute you!

But everyone else - are you satisfied rubbing one out to only fans girls forever?

I was more aroused in a different way. Mine led for hiding like I was straight, to being femmed, crossdressing, to full sissy with my girlfriend to wanting more. HRT and changing my life. I go either way, full bottom and living it. Covid provided a way to hide as I transitioned and my job was/is on the phone. My sister is highly supportive as she questioned this as a child.. My secretary has known my every step and life is good. Finding people for friendship and passion isn't easy. Mine was by chance.

 

[Escierto]

Yeah, virtual trans girls are likely to be the extent of things for me. Satisfied though? I'd have to express that in degrees. So on a scale of "miserable and aching for hands-on" to "Damn, can't wait to fire up the laptop and stroke" I'm at about the "I'm a chicken shit, this is the best I can do" stage.

Good response. I like your honesty about where you stand. Kudos, my man!

 

[Escierto]

I was more aroused in a different way. Mine led for hiding like I was straight, to being femmed, crossdressing, to full sissy with my girlfriend to wanting more. HRT and changing my life. I go either way, full bottom and living it. Covid provided a way to hide as I transitioned and my job was/is on the phone. My sister is highly supportive as she questioned this as a child.. My secretary has known my every step and life is good. Finding people for friendship and passion isn't easy. Mine was by chance.

That’s excellent!

 

[anniebaby10]

I love looking at very feminine trans women as well in particular with those that have HRT induced breasts. They are so soft and beautiful looking and then their hard cocks add a special extra sexual enticement. Being a bi female they excite both sides of my sexuality. Never been with one but sure a fantasy

 

[Escierto]

I love looking at very feminine trans women as well in particular with those that have HRT induced breasts. They are so soft and beautiful looking and then their hard cocks add a special extra sexual enticement. Being a bi female they excite both sides of my sexuality. Never been with one but sure a fantasy

You could make it happen. Many trans women are lesbians.

 

[womaneater58]

I really enjoy looking at pictures or videos of beautiful women while jacking off, they look so sexy and when I notice she has a cock, I cum pretty quickly. I'd love to meet one but I know that will remain just a fantasy.

 

[Escierto]

I really enjoy looking at pictures or videos of beautiful women while jacking off, they look so sexy and when I notice she has a cock, I cum pretty quickly. I'd love to meet one but I know that will remain just a fantasy.

You never know. It could happen.

 

[Escierto]

During the covid lockdowns I started watching trans women porn, which led to interacting with trans women on cam sites. I find this incredibly arousing and am contemplating whether I will ever move this from fantasy to reality. The urge gets stronger as my online interactions continue, so not sure what the future holds.

This is exactly what happened with me. I started interacting with some of the women on the cam sites and that was satisfying for a long time. Eventually I started looking for trans women on some dating sites and this led to actually meeting two of them. The second one has been my girlfriend for the past five years.

 

[Escierto]

So interesting that you had the same early experience I am having. I agree the online cam sites are very satisfying, but they do get me thinking...

These three stories cover much of my journey in detail:
https://www.literotica.com/s/from-family-man-to-bottom-bitch
https://www.literotica.com/s/from-family-man-to-bottom-bitch-ch-02
https://www.literotica.com/s/from-family-man-to-bottom-bitch-ch-03

 

[htobeme5]

This is exactly what happened with me. I started interacting with some of the women on the cam sites and that was satisfying for a long time. Eventually I started looking for trans women on some dating sites and this led to actually meeting two of them. The second one has been my girlfriend for the past five years.

hope you get her in the states soon. I thought you had been together 2 years. She is definitly a keeper.

 

[Escierto]

hope you get her in the states soon. I thought you had been together 2 years. She is definitly a keeper.

Yes, she is a keeper but she wants to remain in the Philippines.

 

[desire30]

I feel the same. I’m lesbian but very curious about Tg. I don’t dislike any gender or preference but I don’t have any experience except for female.

I feel the same as well . the great part for me is one of my great friends isTG. Stunning body, Amazing cock, and a dream more assertive type lover

 

[LovelyLadyLicker]

I was going to title this thread “Questions for the tranny chasers” since it is an existing expression with a very specific meaning. However I hate the word tranny as well as the whole expression itself, so I thought, NOPE. Anyway, onwards!

One can’t help but notice the number of threads with pics of transgender women and the popularity of this topic. This should come as no surprise since transgender porn is extremely popular.

These threads elicit many comments from admirers of transgender women hoping that somehow in some unspecified way, their desires for these women will be fulfilled.

My question is this: what, if anything, are you doing to realize these dreams? If not, why not? Do any of you actually contemplate a relationship with a transgender woman?

My [somewhat recently] ex is a transgender woman (or we say “trans” for short). I wouldn’t say it was a dream to be with a trans woman, as im pansexual; it just kind of happened. Although I first discovered my attraction to trans women when I kept having crushes on gay men and/or effeminate men. I eventually connected the dots and a year or so later, she walked into my life. The relationship ended for insecurity reasons and I still think about all the ways I admired her: her beautiful shape that happened to be fluid due to hrt; her goth fashion; her eyes that reminded me of autumn trees and meadows; her wolfish smile; her absolute MONSTER of a cock (though that’s not necessarily a preference ); her pretty laugh; her ever-changing voice; her sensitive, perky breasts; soft moans at a moment's caress; and love for worshipping my feet. I think it’s safe to say, although I’m Androgynous…I may be a lesbian.

 

[Escierto]

My [somewhat recently] ex is a transgender woman (or we say “trans” for short). I wouldn’t say it was a dream to be with a trans woman, as im pansexual; it just kind of happened. Although I first discovered my attraction to trans women when I kept having crushes on gay men and/or effeminate men. I eventually connected the dots and a year or so later, she walked into my life. The relationship ended for insecurity reasons and I still think about all the ways I admired her: her beautiful shape that happened to be fluid due to hrt; her goth fashion; her eyes that reminded me of autumn trees and meadows; her wolfish smile; her absolute MONSTER of a cock (though that’s not necessarily a preference ); her pretty laugh; her ever-changing voice; her sensitive, perky breasts; soft moans at a moment's caress; and love for worshipping my feet. I think it’s safe to say, although I’m Androgynous…I may be a lesbian.

It sounds like you are still in love with her. The way you describe her reminds me of how I would describe my girlfriend who I adore.

 

[Escierto]

My mom said she always thought I was a bit light in the loafers growing up. Just from my mannerisms, the inflection in my voice, my interests, and my absolute failure in doing well in any male oriented activity like sports and scouting. She told me of a story about when I was much younger about when I threw a nuclear temper tantrum to get a little mermaid swimsuit like my girl cousin had. It was so bad she gave in. So she wasnt too suprised when she found my stash of girls clothes in a couple of backpacks I kept under the bed when she decided to vaccuum my room one day. We had the big talk, I returned the clothes to the school lost and found where I took them from. Thanks to virtual site like here and IMVU I have been able to nuture my feminine muse and experience a life that I am now starting to explore in RL. And, after a serious chat between me, my mom, and a counselor from the LGBT center mom is more open and actually supportive. But she doesnt know all my secrets...wink

Would you describe yourself as a transgender woman? It's good to hear that you are taking the steps towards being your authentic self.

 

[LovelyLadyLicker]

It sounds like you are still in love with her. The way you describe her reminds me of how I would describe my girlfriend who I adore.

I still have love for her and I doubt that’ll ever change.

 

[Not Normal]

I'm not even sure how, but I became friends with some trans women and female presenting enbys through Twitter. There is a women I tried in earnest to start a relationship with. She wasn't sure about how she felt about men. We had some nice flirty chats, but I realized she was never going to let her guard down enough for even a long distance thing with me. We're still friends, and she's going through a huge thing right now, and I think I probably am better off.

That doesn't mean I wouldn't ever again attempt to be with a trans woman.