After months of working from home I have to make a customer visit again. And not close by, I will have to fly. Could it get any worse?

Oh yes, my boss is coming too. She's quite capable, especially on the server side stuff, but she's not a very sociable person. On top of that she's not very fashionable either, always dressed up like a guy in a bad suit. Could it get any worse?

Oh yes, the company is very low on cash, so we have to take the cheapest flight. Which happens to be the one at 6am on Saturday morning. Could it get any worse?

Oh yes, the return flight is not until Sunday a full week later at 9pm, so I won't be home until way past midnight. So essentially I will have to spend two weekends in Orlando with a person that I have nothing in common with, other than that we work for the same company. Could it get any worse?

Oh yes, she picked me up at 3.30am so that after half an hour drive we have two hours to get checked in and through security. Now I don't move very well until my first coffee, but my machine broke down, just when I needed it most. Could it get any worse?

Oh yes, nothing was open yet at the airport, and without caffeine in my system I hardly noticed that she was actually dressed quite nice for a change. She was joking with the attendant when we checked in our bags and then she actually kissed the woman behind the counter. Could it get any worse?

Oh yes, due to safety concerns there was no coffee during the flight either. And despite social distancing I had a kid behind me kicking my seat and preventing me from catching up on my sleep. Could it get any worse?

Oh yes, her luggage came down the belt just fine, but my bag was nowhere to be seen. When I made up a report I found out that it was on it's way to Hawaii and it would take at least a week before I would have it back. Could it get any worse?

Oh yes, somehow they turned it so that it was my own fault and therefor they would not reimburse me for any clothes that I would buy this week. Besides that I had racked up my credit card during the few weeks I was on furlough and the hundred dollars that I had in cash I forgot to bring. Can it get any worse?

Oh yes, when we reached the hotel I learned that to save money we had to share a room. And the only room available for early check in was with a king bed, rather than two queens. I needed to sleep so badly by now that I went along with it. Could it get any worse?

Oh yes, when we were in the elevator I searched my wallet for a dollar to give to the guy that carried her bag, not mine as I had no bag. And my driver's license dropped out exactly into the little void between the door and the elevator and it was gone. The guy said he would report it to the elevator maintenance but they only come once a week due to the pandemic and they were there just last night. So I have no ID for a week, no credit card, no clothes and hardly any cash. Could it get any worse?

Oh yes, in the room there was only decaf and my boss was fine with that but I really needed some caffeine. Or sleep. She made it clear that she had no problem sharing the bed with me as long as I would behave. I wanted to protest but I realized it would not help my case. And when she came out of the bathroom in very sexy lingerie my mouth dropped open and I could not hide my hard-on. Could it get any worse?

Oh yes, she repeated that I was supposed to behave and I was clearly showing that I was not. She said she would take care of it and before I know it my pants are down and my dick is in her mouth. I have to confess that this part was actually quite nice and when I came she swallowed it all. For a minute I was in a bliss that beat caffeine while she was cleaning me and who knows what, but then she kissed me full on the mouth and before I knew it I was swallowing my own cum, that she apparently kept in her mouth. Could it get any worse?

Oh yes, after I got rid of my own taste I realized she had locked something on my shrunken dick. She called it a chastity cage, to make sure I would behave from now on. She had the key and she would give it to me when we get back home. Then she threatened me that if I didn't do what she commanded she might actually drop the key in the elevator shaft. Could it get any worse?

Oh yes, she accidentally dropped her coffee on my pile of clothes and now I had nothing to wear. She put it all in a dry cleaning bag and hung it outside the door. It would not be ready until tomorrow. She gave me one of her panties and a nightgown and told me to put it on. She would not allow me to sleep naked in the bed. Could it get any worse?

Oh yes, I was so tired from the trip and I slept so deep that I didn't notice when she glued fake breasts on my chest. I woke up because I had to pee so bad and she warned me to sit down with that thing on my dick. In the mirror I caught sight of myself and I suddenly realized what the weight on my chest was. But I had no time to investigate as I needed to go so badly. I pulled down my panties and sprayed the whole seat. Could it get any worse?

Oh yes, I quickly managed to dry the seat and sat down while I let go of my bladder. It trickled into the bowl and I felt like a girl. And when I felt the weight of my tits in my hands I realized I was more a girl than a guy now. Could it get any worse?

Oh yes, when I was finally done I had to wipe myself clean. And when I washed my hands I saw my face covered in makeup. It was pretty actually but shouldn't be on me. I considered washing it off but I figured my boss would not be happy if I did so. And I was right, when I came out she was holding the dress for me to wear. Could it get any worse?

Oh yes, I had to wear a bra and matching panties, stockings and a garter, a slip dress and when she finally zipped the dress on me she started on my hair. I always wear a ponytail but in a manly way, but she styled it very feminine. Could it get any worse?

Oh yes, she asked me why my skin was so totally hairless. I proudly told her that I had won a full body laser hair removal treatment during an office party. Well sort of, because the two guys that won it before me returned it back to the pot. But I liked it, I hated shaving so I was glad to win that prize. Then she mentioned that she had donated that prize for the party. Could it get any worse?

Oh yes, she made me wear heels. They looked good on me I have to confess, but walking in them was hard. She didn't give me any break, I think I walked for miles until it finally became easier. Then she made me sit, pulling my skirt under me, crossing my legs. Then get up again and walk, over and over again, until I could do it without thinking. Could it get any worse?

Oh yes, I looked, walked and sat like a girl now but I still sounded like me. She gave me a little pill and after I took it I felt a bit giddy. My voice went up indeed but I couldn't stop giggling. I suddenly became extremely aware how sexy I was and when I rubbed between my legs I became painfully aware how that cage kept my dick small. Could it get any worse?

Oh yes, she told me my name was Jaclyn now and I better get used to it. She confirmed what I had assumed, that she was a lesbian and I was to act as her lesbian girlfriend. No, not just act, be! Could it get any worse?

Oh yes, she made it clear I was the girl in our relationship. And to proof the point she pulled her own panties down revealing quite a large dick on her. I was stunned... could this get any worse?

Oh yes, she reminded me of the blowjob she gave me and I owed her one. And I better make it good and swallow. I had to sit on my knees in front of her and then she filled me up. I could hardly breath and I realized that by bobbing up and down I could get some air. But it also made her member grow in my mouth. It hit me deeper and deeper and when I tried to pull away she held my head. And then she came. Could it get any worse?