The Business Trip

It started out as a simple business trip, nothing unusual for me even if it meant I had a tag-a-long manager for a couple of days. Normally we were sent on these types of contract finalizations alone for the simplest of reasons: all we had to do was be there to notarize the final signature and go home. But on this trip one of the regional managers decided to come along and introduce himself to the new client. The manager's name was Marty, and aside from the occasional screaming match with a client trying to skip a payment on their bills, you would never notice him in or out of the office. In fact the most remarkable thing about Marty was the amount of time he spent on the road by Himself, tracking down new clients personally, etc. Of course, now I know just how remarkable his trips can be.

I tend to stay in a small to midsized motel room when I'm out of town, the company would foot the bill for better (to protect our image and all), but all I really do is find a local tavern, or buy a sixpack and watch whatever game is on the cable that night. So a bigger bed or nicer sheets don't make much sense to me. Entertaining clients is not my forte, sealing the deal is. I get in to town early, finish all the preliminaries and wait for the word, its become automatic for me at this point. I never expect any surprises and am usually not disappointed. Marty one the other hand is like my polar opposite. He like to get to know the clients, do a couple business lunches, hit the towns he's in, live it up. Everyone at the office knows this, because his expense reports for his trips are always a page longer than anyone else's. Two pages longer than mine, I foot the bill for the beer myself. It never matched up to the Marty we all knew and barely saw in the office.

So, we both got into Chicago on a Thursday morning. I came by car, as I was out on the road already. Marty came in on a commercial flight out of New York. The company let me make the reservations since I was scheduled to be there for a couple of days longer with a different client later during the following week, and I chose the usual no-frills motel. Off the interstate about 5 miles from O'Hare. Nothing special. I dare say Marty wasn't thrilled. We weren't use to working together and didn't really know each other, so it came as no surprise when he hinted that he was probably not going to spend a whole lot of time near the motel this weekend. I just headed to my room and bunkered down.

The first two days went by quickly, I finished the paperwork for this contract and most of the paperwork for the following meeting, Marty passed by my window at all hours of the day and night, always in a hurry. I wasn't' trying to be impolite, but I just ignored him as best I could. Then came Saturday night.

Now, as a football fan, I treat Saturdays and Sundays like my own personal holidays during the season. After a full day watching the games, I like to go out get a quick bite, and if I haven't found a good watering hole within walking distance of the motel, I just get a couple sixes from the 7-11 and ice them up in my room for the night games. I was half in the bag by the time the 3;30 games had ended and decided to make a run for some grub. I grabbed my little keycard and headed out to the parking lot. On my way I passed Marty's room. I got a couple of steps past his door when my better angels told me to be a nice guy and offer to pick him up something. Or at least make an effort to be nice. So I knocked on the door, Not to loudly, I could hear music on , but not so loud that it would drown out my tapping on the door. After a couple of seconds with no answer I decided the fates had meant for me to make a beer run alone, and started to turn away from the door. Before I cleared the doorwell, it opened. Not a lot, but enough for me to make out Marty in a bathrobe, and a towel on his head. I almost laughed out loud, I'm on the road at least twice as much as he was and I don't even own a bathrobe, let alone bring one on trips with me. It must have showed on my face because Marty suddenly looked taken aback. I broke what was becoming an awkward silence by blurting out, "hitting the store for some grub, you want me to pick you up something?"

The look of relief on his face was palpable and his shoulders positively fell to his sides with a sigh. I was going to ask what spooked him, but let it slide, it wasn't my business. He said he wouldn't mind a bag of nachos so let him get his wallet. I said I'd catch him on the way back, but he insisted his wallet was right there so it was no big deal. He went towards the little nightstand all these places have next to the colorfully decorated bed, and as he did , I saw something I wasn't expecting. As he got further away from the door, I could see the bottom of his bathrobe. This was only noticeable because his white bathrobe was a sudden contrast to what were quite clearly dark black stockings. Not socks, stockings. As he turned around with the cash now in his hands he saw me looking at his feet and realized what I could see. And suddenly he didn't know what to do or say.

He started to babble about how it wasn't what it looked like, he could explain, etc. I calmly took the cash from his now clenched fists and said , "so you want nachos and salsa right? I'll be back in a couple of minutes." He stood there with a look of panic on his face as I walked to my car and drove off.

Now, as I drove around the corner, I couldn't figure out which one of us was more freaked out. Him for having been caught wearing some women's stockings, or me after seeing it. It wasn't something that would have ever crossed my mind about Marty in a million years. I knew I didn't know him all that well from work but now I realized that even what I did know could probably be thrown out the window. When I finished paying for the beer and snacks, I found myself sitting in the car thinking for more than a couple minutes. It wasn't like this was some dastardly secret he had been keeping from me for years, we barely spoke even when it came to business matters, so I saw no point in getting all worked up over it. And its not like we didn't have some gay and lesbian colleagues so what was one more lifestyle. As I started my car up and headed back to the motel I decided to just let the matter drop and go back and watch the late game like I had planned.

I walked up to his door and knocked. He opened it in an instant and I guessed that he had been standing there the whole time waiting to explain. He started to but I told him it was cool, he could do whatever he liked in his free time, it didn't bother me one way or the other. After I said that, he still looked at me with some furtive looks, Trying to scour my face for any signs something was wrong, or that I was about to drop some kind of bomb on him. He seemed at least a little at ease as I excused myself and headed off to my room beer in hand.

I'd like to say I completely forgotten about the whole thing, and for the most part that would have been true. I threw some ice in the little sink outside of the bathroom to keep my beer cold and proceeded to watch the pre-game show and caught up on any action I missed from the games not on the inroom cable system. Occasionally, mostly during commercials, my brain would jump back to the thought of Marty in women's clothes, and I would laugh a bit. As the game wore on I had already become used to the idea and started to lose interest in thinking about it.

However, at half time, I little football trance was broken when I heard a knock on my door. I got up and for a brief second could not figure out who would be bothering me here. Of course by the time I opened it, I knew it was going to be Marty. Sure enough, he was standing there, still in his bathrobe, trembling. I noticed the stockings were gone now though. He asked if he could come in, he needed to talk. I said sure, and went back to my seat, which I now had firmly planted in front of the TV. He stood in the middle of the room, slightly shifting from one foot to the other and looking fairly nervous. I offered a beer, but he declined. He asked me what my plans were now. I joked that I planned on finishing the first sixpack and then possibly making a run at the second if the late game was interesting. Of course, I knew what he meant, but he didn't seem to be in a laughing mood at the moment.

He asked if I was going to tell anyone, or if maybe I had already. I said I hadn't told anyone yet, and since it wasn't really my business I couldn't see how it was theirs, so he didn't have to worry. His little secret was safe with me.

When he heard this, it was like every ounce of breath in his body rushed out like a deflating balloon. "I'm soooo relieved to hear that, it's not something I want to have to explain to the folks back at the office. Or at home for that matter." I guess I was a little more curious than I thought, because I asked if anyone else at the office knew, it wasn't like this was the first time he had gone on a trip with someone else, so maybe someone else found out or already knew. He said no, nobody who knew him had any idea.

At this point he sat down on the bed, these motels only give you one chair if you're lucky, and started to tell me how this had been his secret for years. He had started to dress up a bit early in high school, and with 3 older sisters he had easy access to girls lingerie. At first, he said, it was just a little experimenting, to see how stockings felt, how a bra hooked and unhooked. But he also noticed it felt more than a little arousing and started to wear them around the house whenever he could. Sometimes his sisters accused each other of stealing the others things, but no one ever looked at him twice about it. As he became a little older his sisters went away to college and so he had the run of the house to himself most days. He was almost giddy as he told me about the hours he would spend laying around wearing one of the confiscated outfits, with the shades drawn playing with himself all afternoon, only to lose track of time and have to scramble upstairs as one of his parents pulled into his driveway. In fact, he said he occasionally wore nothing but a pair of his sister's pantyhose and stayed downstairs as long as possible trying to add a little extra thrill to his day.

Mind you , hearing this kind of talk from any guy would be enough to make my mind boggle a bit, but hearing it from Marty, I thought my head was going to explode right on the cheap motel carpet. I was thankful I had beer at the ready, because this was just too weird for me to take in all at once.

He must not have noticed how shocked I was, or the beer left my face a little slack-jawed, or maybe he just wanted to get it off his chest. For whatever reason he kept talking. In college, he had a much easier time than most people he that he had heard about, or read about who liked to cross dress a bit. He had his own dorm room, which he never left unlocked, and he was out of state, so he felt comfortable going out a bit in full dress. Occasionally he went to a local gay bar he knew that was far from his campus, and with no one there who might possibly know him, he started to experiment with other things too. At first, he said he used some drugs and alcohol to lower any inhibitions and would hit on some of the guys. When he said this, he looked at the beer in my hand for more than a couple seconds. He said as time went on though, he stopped using them as a crutch and just to flirt with the guys naturally.

I told him that answered my question then. He asked what question? So I told him I had wondered if his crossdressing meant he was gay or not. He laughed at that. He said he at least considered himself bisexual, and did in fact like to have sex with women too, but not while he was dressed as "Kate". I did a bit of a spit-take when I heard that, and that made him laugh a little harder. Kate was what he went by when he was dressed as a woman. He didn't think of himself as a man in a dress then, but rather as a woman.

Now at this point my curiosity was starting to get ahead of me. I asked him if he always dressed up when he was on business trips. Did the clients know? Did he take them to gay bars on the company expense accounts? Now he was laughing quite a bit. No, he said, the clients never knew. He wined and dined them in the old fashion business sense with nice dinners, the occasional ball game, depending on the client a strip club or too, That sort of thing. In fact, he made it a point of throwing the works at them for a day or two, piling it on the expense reports, so they never asked what he did in town when they weren't there. And the company never worried he wasn't showing them a good time. It was the perfect cover for him. And he said he was really hoping I would keep my word and not tell anyone about this. I assured him it was safe with me. Hearing this again, he got up and started to leave, but as he did he told me that now that he wasn't so worried about being "outed" he was going to go get dressed, and maybe hit a local club or two. Maybe I would care to join him, he was more than happy to show me a bit of the wild side if I'd like. He had a mischievous look in his eyes when he brought that one out. I politely declined, citing football and sleep as my priorities for the weekend, and with that he left. As he did, I thought for a second he was going to lean over and give me a hug goodbye, but when he didn't I thought maybe it was just my imagination.

Sunday afternoon was not quite as eventful. I spent the morning finishing the rest of my work, drowning my hangover out with sports radio and Dr Pepper. We both got a phone call from the main office postponing our meeting until Tuesday, but that wasn't a complete surprise to either of us. What it did do for me was give me the opportunity to go out Sunday and watch the pros. I hit a nice sized sports bar and watched the the games on about 15 screens at once. I left the waitress a nice tip and headed back to my room to crash for the Sunday Night game. It was expected to be a bit lopsided, but the basic cable package in the room was going to have it on, so I decided best to play it safe and watch the game there rather than in an unfamiliar area when I was out of town, and more than a little tipsy already. I entered my room, clicked the pregame on, and quickly dosed off.

I awoke to the sound of knocking at my door and once again I forgot I wasn't alone on this trip. So I was going to be a little shocked when I opened it up and saw Marty there. However when I opened the door and saw Marty in full fledged drag, I was absolutely floored. Sure enough he was standing at my door in a really short skirt, a wig, makeup, and what I could only imagine were the stockings he had been wearing the night before. I started to say "Marty, what are you thinking?" when I was interrupted . "now, I told you last night I like to be Kate when I'm dressed silly" A little slurred, but even I could smell the alcohol coming from "her" lips. "See, I brought you some beer as a thank you for keeping my little secret." And like that I had beer thrust in my hands as she walked into my room. She sat down on the bed, and said she struck out at the bars here.

Now it was a little disconcerting hearing a fairly male voice coming out of her mouth. I guessed that it was not a high priority to sound extremely feminine to her. Or maybe it was the alcohol. Either way, it was only slightly higher than Marty's normal voice, but with cherry red lipstick and eye shadow under a curly black wig.

I thanked "Kate" for the beer, and cracked one open, offered it to her. I shouldn't have be shocked that she accepted, I mean she smelled like she had had more than her share, but none the less I was. I was starting to wake up as we started to talk. She asked me what my plans were for the evening now that we didn't have a meeting in the morning, and I shrugged and pointed to the TV, said football and then sleep. Again, I'm pretty low key most of the time. Suddenly she popped up off the bed, and popped into my lap and said I was being silly, we should go out somewhere and raise a little hell.

Now mind you, I too had been drinking, but not enough that I was out of my mind in any sense. Still, it may have been enough that I felt no urge to toss her off my lap. And when I didn't toss her off she seemed more than a little pleased, and started move her hips back and forth a little bit. And in no time it became physically apparent to both of us that I was enjoying myself. When she felt my cock becoming erect she started to move her hips more and more, smiling like a cat who swallowed the canary. I smiled when I realized what the canary could be.

Up until that point it never crossed my mind that I might want to do anything at all with Marty or Kate. To be honest, while Marty may make for a fairly nondescript man, it doesn't quite carry over into making him a knockout female. While I have in my travels seen crossdressers and transsexual who could easily pass for female, Hell Maury Povich seems to have them on his show every other week, Marty/Kate wasn't quite there. She looked liked a slightly feminine, but unmistakable Drag queen, but I still found my hands running up and down her very smooth panty-hosed legs. After a few minutes of dry rubbing and fondling, she made a move and shifted on my lap, moving in for a kiss. The thought of possibly feeling some stubble crossed my mind for a split second, and vanished as my tongue passed through her silky lips. At this point, I was no longer sporting a bit of an erection, I was sporting a raging hard on. And she knew that too. She stopped kissing me long enough to ask me quickly if I was sure I wanted to do this. I answered her the only way I could think of, I leaned in for a long kiss, lifted her up off my lap, and carried her straight over to the bed, where I dropped down on top of her. I asked if that answered her question? She was positively beaming with lust in her eyes.

In no time at all, she had pulled off my shirt and was unbuckling my pants, while had unzipped her little mini skirt, and pulled it down her legs and threw it on the floor. I unbuttoned the little blouse she was wearing, and started kissing down her chest. At that point I would not have cared if her chest looked like she pumped iron with Arnold, but instead I found a soft and slightly rounded chest that fit nicely into her small bra. I had her nipples in my mouth for what seemed like hours, licking them slowly, sucking on them, biting them, sometime biting hard enough to hear a whimper or two, and it drove me wild. As I moved further down her body, I took a second to kick off my pants, and pulled off her pantyhose. Her legs were as smooth as silk. She let out a moan as I ran my tongue up the inside of her thigh and over the gauzy material of her panties. When I did this, I could not help but run my tongue over what was now Her erect penis. I pulled her panties off and it sprang up a bit once I had the material completely clear.

For a second I could see her face looking down, uncertain of what I was going to do next, but she shouldn't have worried a bit, I had her little cock in my mouth in a heartbeat. I may not have done anything like this before, but I knew how I liked having my cock sucked on, and I went to town. For the first couple of minutes, I slowly sucked her cock stopping to put one of her balls in my mouth while I stroked her with one hand. The other hand was slowly entering her tight little ass. I wasn't being gentle, I was methodically getting deeper each time, playing with her prostate as I pulled her deep into my mouth. Her moans got louder and louder which only urged me on. Her cock wasn't very large, maybe 5 -6 inches, but as I held it in my mouth, my tongue caressed every inch of it. As she moaned louder, I started to positively fuck her with my finger, until she screamed she was going to cum! I kept my mouth on her as it erupted, my first taste of sperm was fantastic.