My first experiences were with 100% passable ladies. I even dated one briefly in college who did model work for Clinique. I brought her to my pad a couple of times and my roommates had zero clue. For me, I kept the fantasy of her being all lady as much as possible. She was hotter than any of the pussy carrying ladies I was pulling.

 
And when it came to the bedroom, we kept the fantasy this way. She actually preferred I was all straight man like with her. I didn’t do anything with her she cock. It was as close to straight sex with a trans woman as you can get. And it was hot as fuck.

 
I did try sucking her once. She was a little weirded out by it. I didn’t like it. We both had a good laugh after. It wasn’t until later in life that I found myself enjoying sucking a tranny off.

U may miss it, assuming there is any left in 70 year old women.

My first experience was with a girl I picked up at a club who I thought was a cis female. I just jacked her off and she sucked me. I never intended to pick up a TS, but behind closed doors I figured "what the hell". Glad I did. It was incredibly erotic and just so fun. Started my love of TS gals. I say go do it. Leave no stone unturned!
As Voltaire said "Once a philosopher, twice a pervert." That means you get a pass on anything once....in the pursuit of knowledge.

My first experience with a trans was nothing to write home about.  This was back during the BP days, circa 2011.  I got off work early so I wanted some play time.  I stumbled upon a pic with some of the most perfect tits I ever saw.  Being a tit man, I said wth and just went for it and sent a text.  I told myself if she provides a verification pic then I'll see her.  After some back and forth she sent a pic and I felt obliged to honor the agreement that I had made with myself, plus I was super horny lmao.  We agreed on a price and arranged for her to come to me for an outcall.  She wasn't the best looker in the face, but her body was crazy.  Tall, but skinny, nice enhanced ass, and man her tits were the best I'd ever seen in person.  We got the business out of the way, I dropped my trousers and she proceeded to suck me off on my living room couch.  Her head game was out of this world and maybe it was the taboo feeling of "am I really doing this or is this wrong?" but I damn near came in like 3 mins.  I had to stop and strap up for some doggie.  I can't say I lasted long because I was too aroused and she had some good bussy.  I felt sort of conflicted but the session sparked my interest.  

 
As a beginner you may feel a little nervous, I know I did.  It took a little while after my initial encounter to see another TS provider, maybe 3 or 4 years, and my first time actually sucking TS dick I was hesitant as well. Now I don't really put much thought into it, I just look at it as pleasing my partner sexually, no different than DATY on a cis-girl.  I'm a visual person and idk why but the sight of a hard cock and tits just does something for me.  I enjoy the visual sight of seeing a hard cock and thinking that maybe the provider is just as horny as I am.  For me a TS girl provides that "I'm horny too" visual that cis girls in this business don't always portray.  Nowadays I think I get off just as much watching TS porn as I do regular porn.  

Go treat yourself to a real hot ts gal. Its a fun time.

My advice is to find a girl that’s extremely passable with the best tits. You’re gonna question what you did after the fact for a little while. You’ll come to terms with it better if she is all woman besides the cock.  

Been seeing TS girls for years and don’t have much interest or practice sucking dick but I’ll eat her ass just as eagerly as I’ve chowed down on some pussy.

I've had three. Good passable ones can be difficult to find and quite expensive. I consider myself hetero. My main curiosity came from enjoying an orgasm with a dildo up my ass. I figured I could accomplish the same feeling with a trans partner. None of three I saw were successful on accomplishing that deed. Actually some TD women can be real jerks. Still looking to find the right one.

If you wanted to read more replies. I’d asked a few months back. Hope it will be helpful

My curiosity got the better of me and I planned two dates a day apart.  I didn't want a potentially bad 1st experience taint my  outlook.  If both were bad, then I was done with the experiment.

I chose providers that were very passable, versatile, and slight builds with 5-6" cocks (cut). I also figured that the worst that could happen is that I'd make out, suck titties and go greek.  I also told each one that I was new to this and gave my age (70s) and description.  

First girl was tall thin Asian model.  No kissing and more mechanical, but wow what a body. I did suck my first dick and while wierd,  I felt the same way as eating pussy, namely wanting to give her pleasure.

Second girl hooked me to it. All American cutie. We made out the entire time, and she was into it as much as I was.  

Recently I had another great experience with an Asian trans girl. I am still interested in women but find myself always checking the shemale ad section at sites.  I avoid dominant girls that only top, ones that are flat, and girls that don't get hard (read reviews to find out).  I am not looking to get bottomed, but if the situation presented itself, who knows?

My first (and only) TS experience was with this stunning woman from Brazil that I met on a dating site. We were immediately smitten with each other and we DFK'd/canoodled within in 15 minutes of meeting each other. We couldn't keep our hands off of each other, it was so hot and I had no idea. After a few dates we decided to pursue our relationship sexually and we ended up back at her place where she finally revealed that she was trans. Wow I was shocked. I felt a little upset at first because lying thru omission, but honestly I was so turned on too! I told her I was ok with it and even curious. She laid back and I pulled up her skirt to reveal a rather large uncut she cock bursting out of her silk panties. Well push came to shove and we had a very passionate time with lots of mutual oral, mutual rimming and I ended up topping her. I think I came 3-4 times that night. She shot a giant load at one point. It was a super hot and we saw each other a couple more times for some raunchy fun, but ultimately it just wasn't for me and we lost touch eventually.

If you're in Chicago, spend the money for Rachel. She is great with first timers. Pricey but for how she will work with you, it will be worth it.

I had occasion to have my first foray into the TS world with a beautiful woman who went by Authentic Asian Coco my visit was awesome and I am concerned thats most of the others will pale in comparison.

Reading about all these first time stories! It's never too late to take the plunge and try something new!

recently have done a threesome,a women and a ts :u get both world!

Found myself fantacizing for years, then, about 6 months ago, I did it, and have not looked back.  Typically Asian (Thai mostly) providers in nice hotels.  I have not yet been penetrated, but have pretty much done everything else.  Yes, sucking a cock is great.  Found one provider and have seen her now 4 times.  And I've gotten burned a few times.  I guess that seems to happen with all the providers out there, some are better and some are fakes.  YMMV as they say.  Not planning on stopping any time soon.  I also have a price point of 400, 300 most of the time.  But I'm sure that will change at some point.

I was curios for a long time.  I was in Panama City and saw some ladies hanging out along a street.  I went up to check them out.  I didn't know a lot of the country's language.  I used a dictionary to communicate.  After while 4 of them got in to the car and they told me where to go.  We got a room at the No-tell hotel.  That was my very first time and the last time I was ever with 4 T-Ladies at one time.  It was okay.  I was mainly between their nice legs.  My gateway dream lady Carla came soon after that.  Some T-ladies don't want you if you are over 40, but will still take your money.  And they might go through the motions for a few minutes.  The best way for possibly having a good time, is to be super nice and really respectful to them!  Plus really good hygiene.  Ran into one bad hygiene lady in Costa Rica.  The others were okay.

I've been with some real awesome ladies since, but some bad ones also.  Personally, I think most of the good ones where down in South America.  I met some pretty good ones in the country of Spain!  In other parts of Europe I met some good South American talent.   Thailand was my favorite place in Asia.  The favorite place was in Example, Barcelona!.  More lovely T-Ladies in a mile, than most cities!   South America was the most economical, except for Rio de Janeiro.  
I did most of my looking on the local T-lady web-page.  I'd go to www.DuckDuckGo.com to do the search and type it in their language.  And I also used www.Distintas.net a lot.  Plus this web-page has a "Search" engine.  My Job paid me to travel the world.  And I took full advantage of doing that!  

I got a lot of Post, sharing T-Lady and other info.  I also got some Reviews that were allowed.  Hope this helps and that you return the favor!      

I was never curious about other than online.  
I went to a Thai massage shop 10 years ago where the girls lined up. I picked a cute girl and went for my massage.  
Lying down naked she messaged me playing with my cock and balls. There wasn’t much roaming except her rubbing her against me. On the flip she gave me a bbbj. While she was doing it I played with her nips. Then roaming to find her pussy and to my surprise she didn’t have one. I let her finish. I went back the next morning with more on my mind. Pick a different girl. On the flip she was clearly a tgirl. She was just hanging out. Instead of oral on my I performed a bbbj.  
I’ve been hooked ever since been with TS, CD and post op TS. Even with MMF and MTM.

I'd gotten intrigued by two factors: first was a great S&M gal including a little strap-on action in our first meet.  (I later went back to her strictly for GFE.)  It mostly felt awkward and uncomfortable at the time, but I think a mental seed was planted.

It was months or years later when I started getting into TS porn.  The first video was a simple thing, a gorgeous, bodacious woman sitting and stroking a big, hard cock.  It was a moment when I got kind of addicted to the whole scene.

Again, it was months or years later before I took the plunge to see a local TS lady.  She was tall, busty, just a bit above average in endowment.  She was enthusiastic starting off intensely GFE.  When things proceeded to me giving her a bbj, it was odd, but pleasant.  She was not as I recall one of these aggressive throat fucking types.  Later on, she lubed me up, put on the condom, and started fucking my ass.  I couldn't believe that I was doing that!  That's really my dominant reaction - thoughts along the lines of "What The Actual Fuck Am I Doing???"  it was a mix of 1/3rd uncomfortable, 1/3rd painful, 1/3rd an intense sexual turn-on.

Slowly, over the years, I've turned into a rather cock hungry bottom whore.