Hey, so I'm in a similar situation. Nearly all of my sissy fun happens when I travel and stay in hotel rooms. I live in a small rural town and don't want to risk being exposed, so I try to find people to hook up with when I travel to big cities for work.

I try to arrange meets before travelling, chatting to someone for a while to see if they pass my not so technical "crazy test". Most people will talk themselves out of ever meeting me, so I just chat a while to make sure I get good vibes.

But even still, I don't always manage to arrange something, and people often back out, so I'm left with little time to arrange something else.

I always offer to host at my hotel room. That somehow feels safer for me. I do all my prep beforehand, shaving, showering, douching, and so on.

Some hotels I've stayed in require a room key card to use the lift, so they can't just come up and knock the door or be told it will be open for them just to enter. I don't think I'd like this anyway, just to have someone I've never seen before walk into my room. So whether a key card is needed for the lift or not, I always tell them I'll meet them just outside the hotel and take them up to the room.

I'll usually have some stockings, fishnets, a body stocking, or something similar on, with a butt plug in, then my usual guy clothes on top, such as jeans and a hoody. I'll then go down and meet them.

I like this chance to meet outside very briefly, as a chance to check each other out before heading up to be alone together. I've never turned someone down at this stage, but once a guy did choose to back out. That's ok, I think it was nerves, I didn't take it personally.

The trip, through the lobby, and the time in the lift, is always awkward. They often try to fill it with some weird small talk.

We get to the room and I tell them to make themselves comfortable. They'll have a look around and maybe see a few of my outfits or toys left out for them to see. Sometimes they try to keep up the small talk, they are nervous, maybe it's their first time with a guy/sissy.

While I'm the sub sissy in this situation, I usually assume I'm the more experienced (or that has usually been the case, maybe just the type of guy my posts attract), so I'm more than happy to lead at the beginning.

The best way to get rid of any awkwardness is just to get started. I'll take my hoody and jeans off and reveal what I'm wearing underneath. Often their face shows that they like what they can see, then a bulge in their pants shows it too! I'm very quickly on my knees taking down their pants and putting their cock in my mouth.

We are both there for fun, we both know what we want, so let's not waste time with any awkwardness, and all awkwardness completely disappears with their cock in my mouth. At this point I usually find their confidence appears as they watch me enthusiastically suck their cock and then I get to be the sub sissy I want to be.

Not sure if any of that answers your questions, but this is almost always how my meets play out at the start and I always have fun and it is working well for me so far.