fantasy about being found out and moved up one more step

The new company I went to work for was big enough to have their own IT (Internet Tech) guy; Bob, a fellow was about 35, with a wife and a couple of kids. He was a pure tech geek from hello: tall and skinny with a short, bad haircut. Most of my job was working with our customers via e-mail, so I saw him a lot. “There is always something going wrong with these new computers,” he would say. He seemed to be around all the time, looking over my shoulder as I was working, and grilling me about what virus infected websites I had visited. Since I was just out of college, I didn’t know how much of this I would have to put up with, but I kept my cool and kept quiet. I guess this is what these guys do all day.

One afternoon he grabbed me and said we needed to talk about my computer use and that I should go with him for a beer after work to discuss the problem. At the bar he told me there were some prohibited web pages on my browser, and I might get fired. The sites were of a gay nature so Bob asked why I would be visiting those sites and if I was gay. “No, of course not,” I replied. “But sometimes I’m bored at work and these things seem to just pop up from everywhere. I’m not very good with girls and I just seem to get caught up in some of those sites sometimes.” He gave me a long look and said, “There’s a computer seminar in Seattle next week, you and I are going.” He said he would get me work clearance and set up the arrangements. I was a little nervous, but what was I going to say?

When we checked into the hotel, there had been some sort of mistake, because there was just one room with one king bed. “I thought we had separate rooms?” I said. He replied, “The hotel was booked for the seminar, and this was all they had on such short notice. You can sleep on the floor if you want. Let’s go have a drink.”

I wasn’t in the habit of drinking this early in the morning, but what the hell; I was on a company paid trip. After we had a good buzz, he took me back to the room to change and get ready to go to the first meeting.

After I stumbled into the room and sat on the bed, Bob opened a garment bag to reveal a long red dress and all the accessories for me to put on. “This is what you’ll be wearing today. Don’t give me any trouble. Remember, I can have you fired right now for what you had on your computer.” I gazed up at the dress and wonder what was going on. He continued, “I saw what you were looking at all week. You like this sort of thing, don’t you? That’s why were here.”

On the bed he laid out the dress, gray nylons, a black bra and panty, a black lacey girdle with garters dangling from it, and some shiny red four-inch heels. He guided me up and into the bathroom to shower and shave off all that “nasty boy hair.” I struggled with the razor so he stepped into the shower with me, and finished shaving me. Just before we get out, he reached around my back and pulled me close, kissed me deep in the mouth then whispered, “Don’t worry, baby, you’ll be beautiful. I’ve been watching you, and I think this is going to be just right for us. Now dry off and get dressed for me.”

The full panty and long line bra fit a little snug, the bra had two rubber C cup falsies sewn into it, but the open bottom girdle was really tight. It fit me from just under my ribs all the way down below my ass. I carefully secured all eight garters to the tops of the shiny gray thigh highs. Somehow, the red party dress was just the right size for me, stretchy and tight over the full bra cups, and around my round ass. The shoes fit great, too. After I slipped them on, I stood and found they weren’t all that difficult to walk in.

Out from another suitcase came a ladies short, blonde wig and a box full of women’s makeup. “Sit down and I’ll help you with your makeup. Hurry, we have to get going,” he said. Sitting at the vanity together, he made up my face like a pro, and when the wig went on, gee, I almost could pass as a cute young woman. From 10 feet away, I was a knockout! But where were we going? I couldn’t go to any computer classes dressed like this!

He grabbed my hand and out we went, down the hallway and into the elevator. But he sent us up, instead of back down to the conference floor of the hotel. “Where are we going?’ I asked. He just looked at me and squeezed my hand. The door opened on the top floor, and I could hear a party going on. Bob led me around the corner into a huge penthouse party room. It was filled with men and women all dressed up nice, eating from tables of expensive snacks, and drinking from the open bar. The room had a wonderful view of the city, and everyone was having a fun time.

“Is this the company pre-function,” I asked.

“Well, sort of,” he said, “It doesn’t have anything to do with our company, but it is a pre-function.” The more I looked around, I noticed that the women I saw weren’t really all women. Guys dressed up like women, like I was. What sort of party was this? And why was I here? “This is really why we came here this weekend. I’m not really into sitting around listening to computer geeks all day, are you?” he said. I shook my head. “OK, let’s eat, and check everybody out.”

Bob seemed to know a lot of the people here. I think he went out there a lot. Most of the ‘women’ didn’t look too feminine, but everyone tried real hard to look as good as they could – very clean shaven and expensive, pretty dresses. Bob led me around like I was on display, and everyone seemed to like what they saw. I liked the attention. As the afternoon ran into evening, I noticed Bob getting pretty friendly with some of the more attractive ‘girls’ – grabbing their butts and hugging them; sometimes kissing them like he kissed me in the shower, deep and passionate.

Soon other men were bumping against me, and groping my ass too. I quickly turned and stared at one man who grabbed my ass pretty hard. He took me like a dancer, and bent me back and pushed his long wet tongue deep into my mouth. He held me there for a long time, French kissing me like a date on prom night. He had me pushed back on my heels so I couldn’t resist. He had my head with one hand, and with the other he pushed up my dress, all the way past my corset – exposing my sexy shaved legs, gray seamed back nylons, tight black lacey girdle and one bra cup. He squeezed my breast like it was real; I could feel the crowd watching, and heard them applauding as he molested me. Then his hand fell to my crotch and he rubbed and squeezed me as he kept deep kissing my mouth. After a moment, he stood me back up and let my dress slip back down over my foundations. He told Bob I was a real catch, and off he went. Bob said I passed some test, and it was time to go.

With a big strong drink to go, and back in our room, Bob got really romantic: telling me how great I looked and how jealous he was when I let that guy kiss me and feel me up. He told me he’d been dreaming of dressing me up like this and having us sleep together for a long time. He said he’d been practicing with make up and buying all sorts of different clothes for me to wear. When he saw the websites I had visited, he got so worked up that he couldn’t wait to take me away somewhere.

As he was telling me all of this, he was hugging and fondling me, pulling at all the pretty straps and rubbing all the silky stuff I had on. He sat me on the big bed and spread my legs, pushing the dress up to my waist. He asked if I’d like my cock sucked. Just kidding around, it must have been the whisky talking, because of course, after being groped and kissed like a girl all night, a nice blowjob sounded perfect. But joking, I said I was supposed to be the girl, so I should be performing that act on my man. “Are you really getting into this,” he asked. “Well”, I said, “You brought me here on expenses, bought me all this new stuff, and went out of your way to try to make this a fun weekend for me, what am I supposed to do?”

I’d only had one blowjob from a girl before, and it wasn’t a very good one. And I certainly never had another man’s cock in my mouth before. But somehow I knew what to do for Bob. I slid off the bed to my knees and pulled his crotch up into my face, undoing his pants and pulling his belt all the way off. As his pants hit the floor, his big half hard cock flopped out and hit me right in the cheek. As I opened and took it, he gripped my head with both hands and moaned as if he’d been waiting for this forever.

My head bobbed as I took him deeper and deeper in my mouth, he was face fucking me like some whore. My hand was around his long cock so it couldn’t go all the way down my throat and choke me. I looked up at him as I tried to suck harder, but he was looking to the side, at a full length wall mirror. I looked too. There I was, kneeling in a tight red party dress, boobs bouncing and sucking a man’s cock. I looked just like a young school girl, being violated by her bad school teacher.

He said he wanted to cum in my mouth – and all over my face and dress. I nodded, and kept pulling at his cock and licking and sucking the last 4 or 5 inches of it. He liked it. My other hand was up between his legs, fondling his balls and ass. He looked down and told me to slide a finger in. So I licked one and probed his ass as deep as it would go. He jerked and squeezed my head harder, filling my mouth with my first ever load of warm cum.

I tried to back away at first, but he held my head firmly. “Take it, baby, you earned it.” I gasped for a breath and swallowed what I could, and felt the rest drool down my chin all over my pretty dress front. I choked a little and some cum filled my nose and I had to pull him out. Looking right at his cock head, I squeezed it again and pushed my finger up deeper in his ass. He shot another long stream all over my face, and more dripped all over the front of my wet, slippery dress.

“Yes, keep that up, baby,” He pleaded. He knelt closer and with both hands smeared the cum all over my dress, groping my tits, squeezing and rubbing them, enjoying my new breasts in the silky, wet dress.

I stroked and squeezed him until he was dry and exhausted. I licked all the cum I could find off of him. He fell on the bed and said with a sigh, “Wow! We get to be here together all weekend!”