First time jitters

[FtWorth_texan]

Ok, so during my hobbying, I’ve somehow managed to become so attracted to TS girls. Still love straight girls but da-umm these Tgirls are just amazing! Yes I’m nervous, but I don’t think it’s about the meeting itself, but more about being and wanting to be that bottom. The thought of this one particular Tgirl and her on top of me drives me crazy!! But certainly concerned about the first time pain it may cause. Plus, will I be able to hide it from my SO? Will she know I’ve been playing with someone else due to being bottom?
What’s it like for a first timer? Can someone tell their story? I’m a straight white guy who wants to play, and play hard with a Tgirl! Please fill me in!!

[BostonBad]

SO, spouse?

I wouldn't cheat if I were you.

[Cereal Escapist]

Ok, so during my hobbying, I’ve somehow managed to become so attracted to TS girls. Still love straight girls but da-umm these Tgirls are just amazing! Yes I’m nervous, but I don’t think it’s about the meeting itself, but more about being and wanting to be that bottom. The thought of this one particular Tgirl and her on top of me drives me crazy!! But certainly concerned about the first time pain it may cause. Plus, will I be able to hide it from my SO? Will she know I’ve been playing with someone else due to being bottom?
What’s it like for a first timer? Can someone tell their story? I’m a straight white guy who wants to play, and play hard with a Tgirl! Please fill me in!!

In order.
1) Receiving anal is NOT painful if you prepare correctly and relax (and I guess if you are not taking a 12" cock dry). There are millions of men and women taking it up the ass right this very second so don't build the moment of penetration up so much that you make it painful. Loosen yourself up (or have her do it for you) meaning lube well and just push out/relax.

2. Cheating is often not worth it, because you risk a lot when cheating whether you are married or not. If you don't value your SO enough to preserve that relationship, then cheat away. As for hiding it, unless she inspects your asshole moments after you are fucked, or you start to try to get her to peg you an/or introduce a transwoman to your relationship, how else would she know. If you avoid spending time with her to get fucked, she might figure it out but really, it isn't that hard to hide being with an escort so long as there isn't a paper trail.

3. YMMV. My first time was not good because i was too anxious and as a poor college kid, paying for it was a big deal for me so I was too obsessed with "getting my money's worth" and "trying everything." Again, just relax an do what you feels natural in the moment instead of trying to check boxes

4. Your proclamation of being a straight white guy who wants to bottom can invite vitriol from labelers

5. I can't fill you in...I don't want to top you for no amount of money. I am sure you can find an escort to fill you in.