The next morning, I packed my belongings into a few boxes and put them into my old truck. I dropped a note in my landlord’s mailbox thanking them for renting to me. I had decided since my new boss had been so disappointed at seeing me in my male clothes, I’d show up as cute and feminine as I could. I wore all white lingerie, including some white thigh highs and white 4 inch heels, along with a pretty pink mini dress. I also wore my sexy dark brown wig. Ok, I was ready for the world.
I walked back around the house to my truck, planning on leaving for my last time. As I rounded the corner, there was the cute teachers boyfriend, leaning on his car, looking back up the drive. He turned to see me, and seemed to be speechless. I said, “Hi,” and he muttered a quiet Hi back. He then said,“You’re the guy from upstairs?” I told him I was and all he could say was, Damn. He said his girlfriend said I was the prettiest boy she had ever seen. He said, " You are the prettiest human being I have ever seen." I blushed at that. This guy was sweet. I asked why he was waiting and he said he had a lunch date with his teacher friend, but he was an hour early. He thanked me for stopping and introducing myself. As we stood and talked, I could see him stealing glances everytime I turned or bent over. He asked me about why I started crossdressing and I told him my story, or at least some of it. I told him about dressing for my best friend and doing my first blowjob. He surprisingly said that he wished he had had a friend like me when he was young.
I asked him if he’d like to see what he missed? He said, what do you mean? I told him if he wanted to follow me to the little secluded garden in the rear of the apartments, I would show him. I took his hand and led him around the corner. I pushed him up against the wall and eased his pants down. He had an immediate hard on. His cock had a large mushroom head, like I liked. I sat down at the picnic table and pulled him to me. I slipped my mouth over his cock and gave him a nice, long wet blowjob. He tried to pull out as he was about to cum but I took his cock out of my mouth and told him I loved cum. Then I slipped his cock back to my mouth and made him cum. Mmmm, he tasted good. When I had finished, I asked him if his teacher friend sucked cock like that. He said, not really, and we both laughed. He then said he better get to the parking lot. As we walked around to the lot, the teacher was just getting out of her car. She said, “Dont you look pretty today.” I thanked her and she asked what we were doing around the house. I smiled at her and quietly told her I had been giving him the best blowjob he had ever had. She looked at me and then at him, and said, “Yeah, right.” I told her I was showing him the garden area, and that I was moving. She asked if I was moving in with the little brunette and I told her that we broke up. The teacher said I should stop by if I was ever out that way. I told her I liked her boyfriend, he was sweet. I didnt bother to tell her I loved sucking his cock or that I liked eating his cum.
I got in my truck and backed out, waving at the two cuties. I drove thru town and out to the big house. I parked next to a new white Corvette, wondering who was there. I carried my two small boxes to the front door and knocked. Harold opened the door for me and said, " That’s more like it. You look fantastic. I took the opportunity to pick out a car more suited to your new position. What did you think?" I looked at him in disbelief and asked, “The Corvette?” He just smiled and said if I didnt like it, I could get something else. I gave him a big hug and he told me to go out and give the salesman the keys to my old truck. I did as he said and watched my old rig make it’s way out to the road and disappear.
I went back inside and Harold asked if I was ready to start work? He said I could take my things to the bungalow and settle in. He said one of his secretaries had picked up my uniforms and other necessities and layed out one in my room.
I was eager to see what my new boss expected of me. On my bed was a complete French maids outfit. Fantastic!! I always had a fascination for those short black dresses, the white petticoats, little white lace aprons.
I quickly undressed and put on my first French maid outfit. There was a short sexy wig with a lace band on the top. As I looked in the mirror, all I could think was that I made a sexy maid. I walked over to the big house.
Harold had me model my outfit for him and said he was very happy with it. He asked if I had any reservations about the job and I told him that as long as he let me know what he expected, I was good with it. He said he was expecting e close friends for a meeting in a few minutes. He said they were used to getting what they wanted, so i should go along as i saw fit. He said, dont be afraid to say “No.”
I was to bring drinks and basicly be eye candy. I asked if they knew i wasnt really a girl? He said, “Not yet”, and laughed. The door bell rang and Harold asked if i would greet his guests. I went to the door, opened it and directed the men to Harold. All three looked at me as they went by, one of them uttering something about Harold always having the most beautiful girls working for him.
I went to the bar and waited for the guys to order their drinks. After ordering, they went back to the boardroom to discuss whatever rich guys discuss. I just puttered around the bar, bending over to show my panties, smiling at them when they looked at me. They finally came to some kind of positive agreement. Harold called out, “Miki, can you bring us some brandy?”
I took them the brandy and asked if they needed a thing else. I heard one of them mutter, “A blowjob would be nice.” I walked over to him, smiled at Harold, and asked Harold if he minded, as I motioned Richard, to join me on the deck. Harold said ,“No, of course not.” I escorted Richard outside. I ran my hands up his chest and onto his shoulders, then I knelt down in front of him and pulled out his cock. He apparently was a little frightened by what was going on and his cock had not started to get hard. I could fix that. The other men were standing behind the glass watching. I kissed Richard’s cock and it started to respond. I took his soft cock into my mouth and then eased his balls in with his cock. That did it. He began to harden and I began to suck him. I looked over at Harold and he looked like a proud Papa. I sucked Richard until he finally came. I then stood up and asked if anybody else needed to have their cock sucked? Not so surprising, both guys said sure. I sucked both of them to fantastic orgasms. When we came in, Harold said I certainly deserved a bonus. I smiled at him and told him it was part of the job and I enjoyed servicing his friends.
I escorted the men to the door and I think all three managed to cop a feel of my ass as they left. I came back in and Harold handed me a check for $10,000. I protested but Harold said I earned it. He said during their meeting, the guys were so interested in what I was doing, they agreed to everything. He said he was going to make over a million dollars on that agreement , and he thanked me again.
I took my bonus out to my little place, thinking that I was going to love this job. I changed out of my uniform, into cutoffs peasant top, and high heels and walked out to my new Corvette. The paperwork was in my name and there was an insurance coverage letter there too. I started the car up, thinking, “Boy, this is way better than a 1959 Dodge truck.”
My life had really changed.