I can't transition now because of my health and can't even date, but this is something I've been curious about. Even though I'd like to transition someday I figure I'll most likely stay male indefinitely. Either way, this seems like the best sub forum to post about this subject.

I'm almost 40. Around 20 years ago in college I got into trans porn. Since I was already having health problems back then, I never explored this. I didn't really date anyone after I dropped out of college.

Even without the whole "chaser" stigma in the transgender community, them being on hormones would make it very unlikely for me to try what I wanted to try. IDK if there's any NSFW rules, but I hope everyone knows what I'm talking about. So basically, if I want sex like the women in porn I'd have to get with a crossdresser (I've actually considered finding a guy, but I'd rather not unless very convenient and even then maybe not).

So I'm just curious how this works. I know there's websites so I assume that's where I'd go. Have people had any experience with these kind of hookups? Is it safe? Easy to find a match? Would it be harder (no pun intended) for me to find a match if I was on hormones and couldn't climax or at least visible climax? Would I have better odds finding a match if I showed up as male or crossdressed? I've worn panties and pantyhose before, but I've never put on a wig, makeup, etc.

Like I said, my health is really bad now so I can't really do much atm. I just wanted to find out about this because I was curious and would hope to go this route someday.

You seem to desire to understand a set of rules or normal procedures for dating transgender/crossdresser people. While I'm not really speaking from direct experience, I can safely say there are no such rules or norms. This is a very esoteric area. The closest you'll likely find to a normal way such things happen might be through prostitutes, who often specialize in certain areas of interest.

The whole "trans porn" or "shemale" thing is essentially a fantasy. Most of those models and performers are transitioning in their first months or year or so on hormones. After that relatively brief period they loose the ability to become erect and gradually loose interest in sexual performing. While some remain at sex work for awhile longer for financial reasons, most wish only to meld into society more fully as women.

I'd say the best thing for you to do is to examine your own desires in detail and seek others who share your interests through online contact mediums. I'm sure there are compatible folks in your area. The toughest part of this effort will probably be understanding yourself, which might even take a bit of experimentation. Good luck with it and get well.

The whole "trans porn" or "shemale" thing is essentially a fantasy. Most of those models and performers are transitioning in their first months or year or so on hormones. After that relatively brief period they loose the ability to become erect and gradually loose interest in sexual performing. While some remain at sex work for awhile longer for financial reasons, most wish only to meld into society more fully as women.

Yeah. It's kind of disappointing to know the reality is much different. I know porn in general is unrealistic, but this even more. Once I found out about the hormones (and genital dysphoria) that shifted my perspective. I'm not even sure how interested I'll be in hooking up after going on HRT myself.

That's why it seems like dating crossdressers would be the way to go. I have no desire to be a "chaser". I know that many crossdressers aren't interested in hooking up either (I guess they have a chaser/"admirer" problem too), but there are some dating sites specifically for crossdressers.

Wanabe,
I hope I won't sound condescending with this; I don't mean to.

Your health has to be repaired first.
As part of that, mental health must be addressed, per your other thread.  ;-)

Part of that, if possible, would be counseling ("to deal with the effects of Lyme...") and group "support" meetings.

With any luck, you'll get healthier, and build a network, at the same time.
And that network will get you to clubs, online haunts, message boards...  You get the idea.

BUT, here's the best thing: Maybe! YOU could be the CHASED. Maybe someone wants to help remake you, and maybe you want to be remade.
Sounds like fantasy, I'm sure, but i'm actually talking to someone, out of nowhere, who may fall into that role with me... 

I don't know how to make things START, let alone work, but - I think you can agree, current state of mind isn't working, right? So change your mind! :-)
And the rest can probably happen, given time, luck, and showing up every day.

A thought, if possible - might be impossible given your health right now .
Look for yoga classes. Meet women that way, women talk - be one of the girls that way. Maybe they can help you find a boy, girl, or many, friends.  ;-)
Seems low-risk, low-cost, high return, to me.

-Dianna

Wanabe,
I hope I won't sound condescending with this; I don't mean to.

Your health has to be repaired first.
As part of that, mental health must be addressed, per your other thread.  ;-)

Yeah. I know you're right. I was just curious as it's been 18 years since I've dated anyone. I am seeing a therapist now which is pretty good so far and my doctor is better than all my previous ones. The thing is, my health might never get better and I'm almost 40. Maybe I'm having a midlife crisis  
According to this study, the average life expectancy of chronic illness sufferers is 17 years below the national average so I don't know how much time I have left

The findings suggest patients in this sample are at a significantly increased risk of earlier all-cause (M = 55.9 years) and cardiovascular-related (M = 58.8 years) mortality, and they had a directionally lower mean age of death for suicide (M = 41.3 years) and cancer (M =66.3 years) compared to the overall U.S. population [M = 73.5 (all-cause), 77.7 (cardiovascular), 47.4 (suicide), and 71.1 (cancer) years of age].

And yoga is a good idea. I've tried to get into a routine of doing it, but I'm kind of disorganized and haven't really settled into it. I saw you recommending yoga to someone who was worried about DVT so maybe that can motivate me. I don't really care that much about dying, but that sounds like a not fun way to go out.