All parties involved are over 18 years of age, all acts described are between adults.
The parking lot was cold. Well, not especially. It just felt that way because I stayed in my car in the parking lot of the hotel long enough that it got cold. It felt like I was there for hours, nervous about going in. Really it was half an hour, but long enough to get cold. I thought about what I was doing, being there. About going in and first, asking whoever was at the desk for what he had left for me, then getting ready for him, then doing what he wanted, only to be paid for my time, and then giving some of the money to Sir. I still didn't know why I agreed to any of this. I kept telling myself it was for the money, but I didn't need it.
So...am I doing this or what?
I got out of the car. It was cold out, but nothing I couldn't handle in my regular clothes. I hated to think about what this lot would be like if I had worn what I could only imagine I was about to be given. My pace slowed as I approached the lobby.
It was a middle tier hotel, not a Super 8 but certainly not a Hilton. After some effort, I went inside. I must have looked pained as I entered, as the attendant cocked her head some when she asked how she could help me.
"...uhhh.... Yeah...I'm going be seeing a- staying with um...Mr.- A Mr.... Johnson? He said to go and ask about...that..."
She was cute, too. Same age as me, I thought.
"Certainly, let me see...that was probably before my shift."
She looked innocent, like she would be horrified if she knew why I was there. After looking through her computer and looking around the desk, she lifted up a key card.
"Yeah, like I said, sir, he set it all up before my shift, but it's all here. Mr...Mr. Johnson yes, left a key card for you, and a a note... 'only give the room key if the person asking for it [... She hesitated, confused...] knows my favorite color?"
"Pink. It's pink."
She didn't piece it together herself, she wouldn't have the dirty mind to think of it. Mr. "Johnson" didn't want me to have to show my ID, so he set up a password of sorts.
"Yes, his favorite color IS pink, hehe."
She couldn't help but giggle a little.
"And, he won't be back until 6. That gives us an hour and a half."
Us?
"May I show you to your room, sir?"
"Uhh...sure..."
"Right this way."
The room was on the second floor, almost all the way down the hall. That made me more comfortable, if only slightly. Hopefully wouldn't be heard as much. When we arrived, she opened the door, and gave a brief rundown of the amenities. I was barely paying attention, as there was a bag, a brown generic shopping bag on the bed. I was very focused on it.
"Sir?"
"I'm sorry?"
I looked at her, she was looking at me as though I had missed what she said.
"Will there be anything else, sir?"
If only for a moment, she bit her lip, and looked up expectingly. Even in my nervousness and my confusion, I saw that she wanted me to ask her to stay. I could have, I had time, and could have just left right after...but I didn't.
"No, I'm all good."
"Oh, okay, sir. I'll be right at the desk until 8, if you change your mind."
She left, seemingly disappointed. I was too, in myself.
It took me a moment, but I finally looked in the bag, after making sure the door was shut and locked in every way possible. There was a seemingly simple makeup kit in the bag, remover wipes, a black wig, and a black and orange bra and panty set. It looked like something out of a Halloween sex store, if such a thing existed.
I had watched a few tutorials the week before so I thought I had an idea of what to do. I showered and dried off like instructed, and sat down to do my makeup. Still so weird to think in those terms. I must have applied five times and cleaned off and started over four times before being satisfied. It was harder than it looked. And even then, it was just lipstick, some blush and mascara. The wig was uncomfortable as hell but eventually it looked...like I had a centered wig on. Finally I put on the bra and panties. They...fit. But both felt so weird. Riding up my ass and the bra was just, it felt like a completely unnecessary item on me and didn't stop feeling like that for a while.
I looked at myself in the mirror when it was all done and I looked...like a man in drag. But, it wasn't as bad as I thought. I did a few poses, and even took a photo. One of Sir's requirements. I wasn't as disgusted as I thought I would be. I just was ready to get it over with. I was still so confused about what I was doing.
I sat on the bed and just scrolled through my phone for a bit after that. I was trying not focus on the time. Eventually, there was a knock. Well, the sound of the electric lock cycling and the door handle jiggling, to no avail and then then a knock.
I quickly got up and went to open the door. I didn't have time to collect myself, the polite need to open the door when someone is knocking overcame my need to compose myself, or even look to see i was opening the door for the right person.
"Hi sorry I forgot to unlock it when you were supposed to arrive I lost track of-"
"Hey, it's alright. Wow, you look great."
I blushed, standing there awkwardly, with my hands across my torso.
"Why don't you sit on the bed." He said, and it wasn't a question. Not rude, but not passive either.
He was taller than me, taller than Sir. Well over six feet. Thin hair, but not bald. His six inch beard made up for any hair loss he may have been experiencing on his head. He started to take off his collared shirt. He was probably in his 40s, but his skin made him seem older. He wasn't fat, just a bit of a gut, but his skin looked like maybe he lost a fair amount of weight in the past few years. He was very hairy, too. Sir was not, other than short hair on his head and a small amount above his cock, it was like he was waxed.
"How are you doing? Not too much trouble?"
"No...it was easy getting here and...putting everything on..."
"Try to speak a little higher."
"Oh, umm...is this better?" I said, trying to sound more like a girl. He was down to his underwear, old style briefs.
"This is your first time dressed up?"
"Uh yeah. I have had a sissygasm before, with ummm this one guy, but never did this, I'm not really a sissy I think."
"Could have fooled me."
