This was one of many stories I'd been meaning to put on my blog but haven't yet.
So one weekend I and two other trans girlfriends of mine are going to a party and then probably SRO in San Diego from Orange County. Everything is normal, we go to the party, don't make it to SRO before it closes for the night, then get a motel room because it's 2am and we don't want to drive back.
The next day we hang around Starbucks, a Barnes and Noble and eventually my one girlfriend has to head back. The other friend of mine and I discuss sticking around another day because neither of us has to work the following day and aren't especially ready for the mini-vacation to end. We decide that we can just take the train back the next day and opt to get a room again near Sea World at a cheap but really nice motel.
So we check into the room. It's on the second floor and kinda sorta has a view of the ocean. It's also wintertime in SoCal so there aren't a lot of tourists. I throw my bag and purse on the bed and head outside to have a smoke. Just as I'm thinking to myself, "gosh it's nice they didn't put anyone in either of the rooms next door to us, this guy comes up the stairwell. I'm leaning on the railing smoking my cigarette. He walks right behind me. Then I hear him open the door to the room next to us. Crap. Oh well. He was middle aged and normal looking so I wasn't too worried.
So I'm out there just about to finish my smoke when the guy comes back out of his room next door and kind of stands there and stretches, looks out at the kind-of-view of the ocean and tries really hard not to look at me. Whatever.
Then my friend M comes out of the room to have a smoke too.
Now M is very much anti-stealth. She could be what you call passable, but she chooses not to. She wears clothes that are so slutty that it would make a 21 yo club girl blush. She's totally happy with her presentation. She's also very outgoing and friendly. Once you talk to her, you forget about the clothing.
So she says something to me about a guy that called her to go out on a date later. I tell her it is fine and I'll just watch some HBO and chat online. Then she immediately turns to our new neighbor and introduces herself.

They chat for a couple minutes and then she goes back into the room. The guy is staring at me and I smile and ask him how he's doing?
He replies with, "I totally thought you were a real girl when I passed by you earlier. Wow." He's flabbergasted, which I take as a compliment.
So we chit chat for a minute or two. He tells me he's in town on business with his co-worker and is from the east coast. We say our goodbyes and I head into the room.
Around 4 hours later, I'm in the room by myself on the computer when there's a knock at the door. My first thought is that M lost or didn't take her key with her so I go to the door and look through the peephole.
And standing there in the 45-ish degree weather is the guy from next door... wearing a teddy!
I open the door and grin and say, "HI" And I think I said "WOW"
He just stands there with this sheepish grin and doesn't say anything so I am like, "get in here! It's cold out there!" Not to mention the fact I have a guy wearing a red lace teddy standing outside my room's door

So he comes in and proceeds to tell me how he's never really had the guts to do much dressing until he met us that day.