One Weekend

I was sober enough at this point to drive. I got his room number and the hotel name. I started to put on my blouse over the nighty and put that wrap around dress over the lower half. That was my plan at least. I knew the hotel was going to require me to walk through the lobby. I eyed the little black dress and figured "Why not look like a prostitute?" So I did just that, put the dress over the nighty, the thin nighty was completely hidden under the dress.

I got to my car and drove to the hotel. It was a cold and windy night. It felt different to be outside dressed like that, and it excited me.

I was a little nervous walking through the lobby. I know I got some looks. The elevator ride took forever. It was a glass elevator that over looked the lobby. This is where I realized that if anyone was trying, they might get a look up my dress. That turned me on even more. I didn't turn my head to look, I just imagined a few people looking up and liking what they saw. The nighty wasn't low enough to pass even half my thong, so if someone had the right angle, they got a good view of my ass cheeks.

The doors opened on my floor and I followed the signs to his room. My heart was beating and beating hard. The hallway was mostly empty. Occasionally I could hear a couple engaged in sex. Either it would be her screaming or the bed springs. I came to his door and paused for a moment before knocking on the door.

There was nothing. No "come in" no "Just a moment", nothing. I started to worry. If this was a prank it was a pretty good one. As I was considering leaving, the door opened and he was standing there in a pair of shorts and a t-shirt. He welcomed me in and closed the door. I was good looking and assuming he didn't lie to me in our chat earlier, I wasn't going to have someone who was going to freak out on me and leave suddenly, or kick me out suddenly.

We sat down on the couch together. This wasn't a regular hotel room. It was rather nice. He pulled a couple of beers out of the fridge and we talked and flirted. His hands rubbed and caressed my leg as I rubbed his thigh and would occasionally touch his chest. Without warning he kissed me. His body language became aggressive. My legs were spread and my dress was starting to ride up on me. I stopped him and pried him off of me and directed him to the bed. He obeyed.

I stood up, unzipped the dress and let it fall to the floor. There I stood in the wig, make up, see-thru black nighty, black see thru (but a bit darker) thong, stockings and open toed shoes that showed off my painted toe nails. I crawled into the bed where we continued our kissing. I removed his shirt and ran my lips and tongue over every inch of his chest, or so it seemed. I undid his pants and pulled them off. He had on no underwear. I massaged his dick before sucking on it.

As I bobbed my head, I felt his hands run up my legs and massage my ass and then I felt him removing my thong. He pulled my head off his dick. He rolled me over and said, "I make sure to always go down on the woman before I fuck her." and proceeded to suck me off. I had been so horny and frustrated today that I didn't know if I could avoid it cumming in his mouth. I also knew that, unlike with Derek, if I did it, he could just take me regardless of any protest I might issue.

He reached into a bag on the floor and removed a tube of KY and applied it to my asshole. I was face down, smiling, enjoying his fingers when I realized he stopped with the fingers and it was his dick that I was feeling now. I moaned as it entered and clutched a pillow. I entered slowly into me. He felt bigger than I remembered. Then he started to pump in and out of me. It was slow at first. Then he started to get faster.

My face was buried in the pillow, I was moaning. He was fucking me hard and fast, telling me to take it and calling me a slut. I felt him start to reach around me and pull me back a bit. He was giving me a reach around while he fucked my ass. I wanted to tell him to fuck me harder. I wanted to tell him to keep doing just what he was doing. He was a machine and all I could do was moan. He said that I was a cheap cum loving bitch, and I came on the bed.

He stopped so he could pull the pillow from my face and pull me back with him. I was now staring at my cum. He started to fuck me again and told me to lick it up. I asked "What if I don't?" and he stopped fucking me and threatened to pull out. I started to lick and he went back to pounding my ass. He called me a dirty cum slut and I got excited again.

His rhythm changed suddenly. I began to prepare myself for him to cum. He pulled out of my ass and pushed me from the bed to the floor. I got to my knees and he slapped me in the face with my dick before putting it, rather forcefully, into my mouth.

I tasted a mixture of spit, KY, dick pre-cum and ass. I didn't care. I was completely in the moment. He pulled out of my mouth and came over my face.

I licked my lips, taking some of the cum with my tongue. I smiled and stood up, taking his left and in both of my hands. "That was...incredible" I said, catching my breath. He pulled his hand free and told me to get dressed. "I was hoping we could do that some more." I said, with a bit of disappointment in my voice. He picked up his wallet, reached in and handed me some money. "Take it whore and leave now."

I dick was beginning to harden. I opened my mouth to say something and he slapped me in the face. "Get out before I toss you on your loose ass!"

I stepped into the dress and pulled it up and zipped it.

"What a slow fucking bitch." He said as he sat on the bed. "Look, I'm wanting to get some sleep tonight, can we please hurry this up? You didn't take this long getting undressed."

This was actually turning me on, and pissing me off. "Can I get my face cleaned?" I asked, after grabbing my thong.

He got up on the bed, "Incredible." he said as he grabbed my coat. "Dumb slut can't even take a hint." he said as he crossed the room and opened the door, throwing my coat out. "So long skank." he then said as he pushed me out the door.

I sat there in the hotel hallway. I heard the door lock latch. My dick was hard again, my face was covered in cum, I could still taste his dick in my mouth, my ass had that freshly fucked feeling to it and I had my thong in my hands.

I used my jacket to wipe my face off as I stood up slowly and did the walk of shame out to my car.

When I got home, I stripped off the dress and jacked off as I thought about what just happened, and came again in less than a minute. I then stripped off the shoes and stockings and went to bed.

The next day was Sunday. I put on a long shirt and a pair of panties and didn't do much that day. Aside from when I did the laundry, then I put on some pants.

Monday dawned and Alice was a memory, and I had $500 in cash from that prick Saturday night. I used it for a giftcard so I could do some online shopping. I went to work that week, avoiding any conversation that was about my weekend. I had a great time. I wasn't sure if I was going to do it again, but given the stigma attached to what I did, no matter how much I enjoyed it, there was no way I was going to mention any of it. I didn't even mention that I had sex over the weekend. Just kept it to surfing the internet, watching a movie and playing video games.

This is probably where I should end the story, for now. I'm sure I'll have some interesting stories about my next cross dressing weekend.