The New Waitress

For the next few days I was depressed. I figured that I lost my girlfriend for good and that I was in falling in love with a guy I could never be myself with. I was a mess. This lasted a few weeks until in early January. The boss was giving funny looks all day, not looking very pleased and it was getting me worried. It was the day before payday and that meant the usual blowjob in the office. I was scared when I went up to his office.

He had some documents scattered on his desk that he was leaning against. Usually we sat on his couch and I would lean over and do him but something was different today. I just wanted to get it over with and get out of there so I sank to my knees on his hard wood floor and unzipped his pants and took out his ugly cock. I went right to work. He seemed to take a while to get hard this time. As I sucked him as best I could he eventually got stiff and started fucking my face like he usually did. This was a good sign. He soon popped his load, right on queue right down into my stomach. As I was getting up, ready to get out of there, he stopped me.

"Robin, that's a boys name right?" he asked.

"Girls or boys, I suppose," I nervously added.

"Ya, but you're a boy, right?" he pursued.

"Or at least one of them queeny fags, right?" I looked at the hunting trophies on the wall and pictured my own head up there. I was silent and shaking in fear.

He went on, "while doing the tax forms I noticed this thing here, stating that your previous returns were filed as a male. I thought it was a mistake so I called your last employer in Boston to tell him. He assured me that you were very defiantly a boy. So I thought about it for a while and needed to take another look at you. I'll give you credit, you had me fooled. I don't like being fooled. Who else knows about this?"

"No one! No one, just me I promise." I pleaded still using my feminine voice. I was horrified that he would kill me or beat the shit out of me at the very least.

"Stop, I ain't gonna hurt ya," He said. I was getting ready to leave and asked,

"So I guess I'm fired then? I'll not say a word to anyone on my way out and you'll never see me again, promise." A look of disappointment came over his face.

"No, your not fired! Hell you're the best waitress this place ever had. Not to mention, you suck cock better than any waitress I ever had. If you can keep up the act and keep your mouth shut about this, you can keep working as long as you want," he continued much to my relief. I was about to go and fix myself up when Carl stopped me again. I was confused. My relief was beginning to slip away.

"There is just one more thing," he said. "Now that you don't have to hide what's under your skirt from me, I believe it's time that I finally get to fuck that hot little ass." He had his brawny hand on my arm and wheeled my around to his desk. As I slammed into it Carl pushed me face down onto the desk. My skirt was hiked up to my waist and I felt him pull my panties down to my thighs. I thought about yelling for help but realized that I preferred not to attract any attention. I heard him haucking back in is throat before spitting a big gob of spit on my ass. He probed with one of his meaty fingers at my anal entrance finding the mark and working the saliva in. After a minute of that he unzipped and pulled out his rejuvenated cock, ready for action. He spit again into his palm and worked the saliva over his angry member. Soon his familiar cock head was pressing against my sphincter. It hurt like hell as he shoved it in rather quickly. He didn't let up until I could feel his hairy balls slapping against my sac. He grunted his approval of how good and tight my ass felt around his dick.

Carl began pounding in and out of me while holding onto my hips. I was in tears from the pain that he chose to ignore. Slam! Slam! Slam! His cock was relentless in its anal assault. It was quite rough and my own cock was free and rubbing against the leather of my skirt, which was pinned against the top of the boss's desk under both our weight. He had just had an orgasm less than ten minutes before and at his age I knew that I was in for the long haul. I was surprised to find that my dick was equally as hard as the one plowing my bottom. It was about ten minutes into the fucking that the pain I was feeling turned to numbness. I started to enjoy the feeling of being filled. I concentrated on trying to get Carl off as quick as possible. I started fucking back. I met his thrusts with mine and worked my ass in a circular motion. I found myself panting,

"Fuck me! That's it baby, fuck my sweet ass!" Carl loved this and shifted into high gear, fucking me with everything he had. I loved it too. Finally after almost twenty minutes of drilling, my boss buried himself to the hilt and released his blistering hot sperm into my rectum. We were both panting like we just ran a marathon. He pulled out of my bum without ceremony. I suddenly began to feel somewhat empty. Carl brought his wet, flaccid unit around the desk to my face. I obediently opened my mouth as he pushed it inside. I dutifully cleaned his nasty cock up for him until it was spit shined. As he was fixing himself up he said,

"Good piece of ass, I'm gonna love fucking that every week before payday from now on. Don't worry you'll get the two hundred I promised. Hurry up and clean up, I need you back to work before the rush. Don't forget to clean my desk too." What did he say? I soon realized what he was talking about. I had not noticed that I had cum all over his desk and my skirt. I must have been paying so much attention to his orgasm that I didn't notice my own at the same time. Wow! Like a kitten I lapped up my jism from his desk and swallowed it down. I used Carl's private bathroom to tidy up my cloths, hair and makeup. My ass was so sore, I didn't think I could finish working but somehow I managed.

I was Carl's bitch from then on; fucking and sucking his angry looking cock anytime he pleased. I did negotiate more free time as compensation. The one thing lacking in my life called me a couple weeks later. Sandra was very apologetic for being so selfish to me. She admitted that she had sex with someone else but regretted it. She said that she loved me and wanted me back and said she would be more understanding from then on. I was happy about that and told her that I would have more free time for her as well. I couldn't wait to kiss and make up and told her so. She told me to meet her at her place right away for make up sex. But before I could hang up the phone to leave she said,

"Oh, one more thing, could you come dressed as the waitress, I have always had this lesbian fantasy."