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.

 

[Barbelle]

Probably not what the thread is looking for, but hope it’s ok to share from a cis female perspective.

I appreciate the noted opposition to the term “tranny”, albeit my experience with admiration for trans women kicked off in a bar in San Francisco named the”Tranny Shack” (holler if you frequented, or the End Up, close enough). This was the early 00s, and I just remember great times being introduced to gloriously authentic, artistic, beautiful, badass women. Being pan I would have been open to explore a mutual attraction/connection if ever one arose, alas that was never quite the vibe with anyone I met.

 

[markchamberlain]

Interesting topic! I've been with many trans women. I'm basically straight - married, with kids, and my porn viewing is about 93% straight, 5% trans and 2% gay. By far my favorite MM activity is frotting. I've done this mostly in missionary-like position, with two cocks covered in massage oil and stroked together, while their undersides slip and slide against each other. For whatever reason, this is an absolutely breathtaking feeling for me. I immediately get rock hard and have to pace myself.... I cum huge spurts with minimal stimulation this way.

With trans woman, it's the same activity except way better. In addition to the cock-on-cock stimulation, I can enjoy her beauty, her tits, her soft lips. I find kissing a guy repulsive (not in a judgmental way, I just mean for me personally I can't enjoy it). But if a trans girl is reasonably passable, I can enjoy looking into her eyes, softly caressing her, tenderly stroking her hair, kissing up and down her body, kissing her neck and earlobes, hungrily kissing her soft mouth,.....all the beautiful things associated with straight lovemaking. It is mind-boggling how hot this can be, combing both pleasures simultaneously.

To me, there are two key aspects. The first is that when I feel her warm hardness against mine, I absolutely know firsthand how good that feels for her. With a vagina, I can never know first-hand how my partner feels. And I can't directly observe her arousal. But with an erect cock, the vicarious enjoyment of my partner's pleasure is way more intense because I can directly feel the hardness, and directly know how good it feels for her. The second aspect is a little bit of "forbidden fruit." Being with a trans girl is more forbidden, and more exotic. I feel more daring, and more brazen. I have a heightened awareness of my nudity and hers, as if showing her cock is even more "uncovered and revealing" than a plain bare vagina. I've been watched having sex with a cis woman, and also with a trans woman. With the trans woman, the sense of exhibitionist pleasure was even more intense. Unashamedly showing others that I'm aroused by a trans woman feels like a deeper, more revealing exposure of my soul and my sexuality.

Regarding a relationship - I don't know. I've only experienced short term engagements, like less than 5 times with the same girl. I would definitely be open to having a steady trans girlfriend. One of my unfulfilled life wishes is traveling with a trans girlfriend. I'd absolutely love to got to exotic locations with a trans lover, and go out to dinner and dancing, and take a romantic walk with my arm around her waist. I'd love to kiss her by the lake shore under the stars, before taking her back to the hotel for passionate lovemaking. I'd love to finish in a big splash of her cum and mine, and fall asleep cuddling together in the afterglow, with the scent and feeling of slippery cum on and between our bodies. I'd love to wake up together and go to breakfast, to greet the day holding hands and smiling at each other.

But in the long term, I think some part of me would miss the ultimate biological satisfaction of depositing cum inside a womb. Despite the delightfulness and diversity of kinky pleasures in the world, there is something "ultimate" about filling a womb with sperm. It feels like it completes and satisfies both partners at a primal, biological level, in a way that nothing else quite does. Also, a lifelong relationship has to last through more than just the horny sexual attraction of youth. I have no idea how my emotions would develop across all phases of life with a trans partner. And I guess I'll never know.

 

[CatGirl69]

As a trans woman, I don't like being seen as some kind of "exotic" "forbidden fruit." I'm just a person living her life. I have a wife and a job and a house and cats. I'm not some kind of strange entity from an alternative universe. I'm a woman. There are certainly some trans women out there who love making love with men who see them as exotic forbidden fruits, but I find it more objectifying than affirming or fulfilling.

And, as a trans woman with cis-woman levels of hormones, my penis does not work much like it used to, at all. Generally, the kinds of sensations that would've gotten me off when I was running on testosterone? It feels very different. Estrogen and progesterone make it so the sensations map into the erotic programming differently. Stroking and penetrating just doesn't really "click" anymore. It works better for me to think of it like a big clit. I imagine feminine thoughts, buzz it, and then I can cum. But thinking like, I'm a girl and I'm gonna stroke my member until I spew jizz everywhere? That's way more likely to send me into dysphoria than orgasm. (And I'm not likely to ever "spew" anything ever again, unless I can learn how to squirt someday.)

 

[Escierto]

As a trans woman, I don't like being seen as some kind of "exotic" "forbidden fruit." I'm just a person living her life. I have a wife and a job and a house and cats. I'm not some kind of strange entity from an alternative universe. I'm a woman. There are certainly some trans women out there who love making love with men who see them as exotic forbidden fruits, but I find it more objectifying than affirming or fulfilling.

And, as a trans woman with cis-woman levels of hormones, my penis does not work much like it used to, at all. Generally, the kinds of sensations that would've gotten me off when I was running on testosterone? It feels very different. Estrogen and progesterone make it so the sensations map into the erotic programming differently. Stroking and penetrating just doesn't really "click" anymore. It works better for me to think of it like a big clit. I imagine feminine thoughts, buzz it, and then I can cum. But thinking like, I'm a girl and I'm gonna stroke my member until I spew jizz everywhere? That's way more likely to send me into dysphoria than orgasm. (And I'm not likely to ever "spew" anything ever again, unless I can learn how to squirt someday.)

I believe you probably speak for the vast majority of trans women. Thank you!