A courier brought the package that morning, my secretary had told me. I opened the express envelope to find a key card with the name of a high profile hotel near the airport. A room number and a time were written in permanent marker on the back scribbled next to her initials.
The appointment was for that day of course, not more than a few hours away. I'd had to make excuses and told my secretary rearrange my schedule. I wouldn't miss this appointment. I'd been waiting for so long for her to come around. At that point she knew I would even blow off a board meeting to get in her pants. We'd spent too many nights in the last few years hanging on my office phone whispering desperate, deep, dark fantasies to each other while my wife slept obliviously two floors above. She'd become a habit, and worse a fixation.
But lately, I hadn't called her at all. We had to slow down because of my wife. Now that the heat was off, I tried getting her to meet with me by email for two weeks but she were always too busy or something. Oh yeah, she knew I'd drop everything and come. I always came when she wanted to play a game.
I parked discreetly in the hotel's lot to avoid the valet. I couldn't have my name officially tied to a sordid affair. Although, I really got off on the time she'd tied me to whatever she'd wanted to. I made it to the suite evading help and dodging eye contact, acting like I knew where I was going.
I let myself into the room. There was a note sitting on the coffee table of the suite. "Steve, there is a suitcase in the bathroom. Put on everything in the case. Everything. Shave if you have to-no facial hair-no moustache, no beard. When you are finished, turn off all the lights and light the candles. Put on some music and wait for me. There are wine coolers in the refrigerator. Be on the last one when I get here. Do not drink the beer."
What the hell!! I had to shave my moustache and drink wine coolers. Good god. I was going to have to make up some bullshit story for my wife to cover my bare upper lip. She was pushing it this time. And we both knew she was in the position to do it.
I checked out the fridge. There were three cartons of wine coolers. I started with a grape and headed for the bathroom. I had about an hour. The first cooler was very sweet, that I definitely remember. I was glad I hadn't been able to break my lunch meeting. My idea of a good time was not twelve wine coolers on an empty stomach.
I hung up my suit and dress shirt. I opened the suitcase and rifled through it first. After pulling out some of the clothes, I was really starting to wonder what game she had in mind. I found the razor and shaving cream. Given the contents of the case, I considered myself lucky the razor wasn't pink and plastic.
After loosing my moustache, I returned to the case. I pulled out the thigh high black stockings. I vaguely remembered telling her about wanting to wear hose once. This wouldn't be the first time she'd gotten me drunk and had her way with me. I took a swig of the cooler and shrugged. I pulled a stocking up one leg and was instantly hard. I thought, "Whoa I need to slow down." I had to reign this in already.
I pulled out a short black skirt next. I rolled my eyes wondering what the hell she'd been thinking. She was either really pissed at me or... or what? I finished the cooler and pulled the skirt up over my hips and briefs.
On a trip to grab another cooler I saw myself in the mirror. I was blown away. My cock jumped under my skirt. God, I liked how prissy I was starting to look. She must have known I would get off on that.
I think I grabbed a strawberry cooler that time. It was still hideously sweet but I stomached it. It wasn't a far stretch from the Kool-Aid we used to drink as kids.
I dug into the case and found a bra with falsies attached in the cups. She was always so retentive--- I wondered how long she'd devised a bra with fake tits already attached. I rolled my eyes at the thought. It might have been funny but I loved that detail orientation. It made her a great lover.
It took a hell of a struggle to get the bra on- I realized how much easier they are to remove than put on. Next I found a pair of panties at the bottom underneath a long blond wig. I haphazardly stuffed the wig on my head-my focus was all about the panties at that point. They were a silky black pair with a thong running up the back. The front just covered me. My cock throbbed as I danced out of my briefs and pulled the panties up. They held my cock with a constant silky pressure against my cock and the thong strap ran up my ass like a wedgie. A very sexy wedgie.
I shuffled around in the case to find a pair of shoes in there. I slipped on the black heels. They weren't too high, but high enough to make me wobble. The wobble reminded me to keep the pace on my coolers. I went to the fridge to grab another. I think I had a pina colada cooler next. I realized then that she was one of those people who mix and match coolers at the store before buying them. I hate that.
There I was in the mirror again, standing there with my pina colada cooler. The wig was all-wrong. And well, the rest looked pretty wrong too. But it was right enough to have me straining against the panties. What was right was that I looked so... humiliating. God. My head was spinning and my cock was so heavy. I wondered if I should wack off before she got there. I decided I had better not and went back to finish getting ready. There wasn't much left in the case. There was only a button down shirt and a bag of make-up.
I pulled my arms into the shirt and buttoned it over my straining breasts. It was cropped and barely covered my stomach. The buttons pulled across the front when I turned certain ways. I wondered if she had known when she'd packed how nicely my bra would pull across my chest?
I took the make-up over to the mirror and start pulling it out. Let's see... the instructions said put everything on. I set it all out and looked at it. And then I decided I needed another wine cooler before I started. Margarita was next. I thought I must have been getting drunk because that one sounded like it might be alright. I caught my reflection in the mirror and feel a surge of power. It made my cock throb against the silk panties. I kind of strutted back to the bathroom. The power was so heady I forgot the wobble that almost toppled me earlier. I swayed my hips and rolled my shoulders across the room and nearly spilled my pina colada down my shirt. I sobered a bit. It would not be a good thing to fall and sprain something and have to explain that outfit to a paramedic.
When all was said and done, I must say that I didn't do a bad job with the makeup. I'd watched the women in my life enough that I knew what goop went on what part of my face. It looked subtle except for the lipstick. The lipstick was whore red, glossy and tasted sweet. It was very striking against my blond wig. I realized what a bad job I had done on the wig and adjusted it, hiding the stray hairs. I blew myself a kiss. My lips were heavy, pouty and wet. I even wanted them.
Then I really wondered if maybe I really was getting drunk from the wine coolers. I had some serious beer-goggles-- only without the beer. Coolers were really a girl drink. I checked the clock by the bed; it said 3:00. Where was she? She was supposed to be there.
I lit the candles. There are at least a dozen in there-each smelling of vanilla or flowery. I set them around the suite and turned off the lights. When I saw that I still had more coolers to go through, I was glad she was running late. I swiped a wild berry one and something lemon-lime and sat on the couch in the lounge area of the suite. I cringed at the lipstick I left on the bottle. I would have to keep re-doing it. I wanted her to see what a good job I'd done. I wanted her to want my mouth like I had.
I finished another cooler and thought about masturbating again. I walked over to the mirror and watched myself. I turned one way and then another and swayed my hips a bit and remembered I was supposed to play some music.
Thankful for something to do, I found a station on the hotel TV channels whose music wasn't too terrible, soft rock and mushy. I am sure that she intended me to pick that for this game.
I worked on my cooler and glanced at the clock.
She was almost 45 minutes late when I reached for the last half of my last pack of coolers. I was starting to get mad. And worse I was mad and drunk. Surely she would show up. I thought there was no way she could stand me up after she went to all this trouble. I relaxed a little at that. Was there a ballgame today? There might be. Traffic was always hell down by the airport on game days. I thought to myself as I finished the coolers from that pack that I would drink her beer since she was late.
But I didn't. I wanted to see how the whole thing would play out. I had to check my makeup three times and pee twice before there was finally a knock at the door. I got to the door on wobbly legs and peered through the peephole. There she was... only she looked different.
I opened the door and said, "Where have you been?"
She looked down the corridor one way and then another to see if anyone had seen me. She tossed her head back and laughed at me. I realized how vulnerable I'd made myself and waved her into the room.
