Harold said he would like to meet him first but he was going to be out of town for 3 weeks. I told Harold that was perfect, that I could train him. Harold asked if he would be interested in moving in with us. I told him that would be perfect.
I called Billy and told him I’d pick him up at his place, his Mom’s house. I pulled up to her house and got out. I was wearing a modest floral dress with 3 inch heels. His Mom answered the door and greeted me, inviting me in. She seemed relieved that Billy had a girlfriend. I told her that my boss wanted Billy to work for him and live on site. She said that would be nice.
Billy came out and I went up and hugged him and gave him a nice quick “girlfriend” kiss. His Mom asked where we had met and I quickly told her it was at the bookstore. Illy looked a little frightened, but I didnt say it was an adult bookstore.
We left and on the way, I told Billy today was the first day of the rest of his life. I told him his training started as soon as we got back to Harold’s place and got settled. I walked Billy to the other apartment next to mine. I had already ordered Billy’s new clothes and told him to get showered and I would be over to help him.
I called my friend at the beauty salon and asked if she had time to give a makeup lesson and she said she had the rest of the afternoon clear. She came over and i took her back to Billy’s apartment. I knocked and Billy told me to come in. He was wearing a cute nightie and was shocked at a woman coming in with me. I told Billy that Barb was familiar with girls like us. I left to allow Barb to teach Billy how to do his makeup.
I was sitting on my patio when Barb came out. She stopped and told me she thought Billy had it but she would come over in a few days and see how he was doing. I thanked her and gave her a crisp hundred dollar bill.
I walked over to see how Billy looked. I knocked and he answered. I was impressed by how he looked. He made a very cute girl. I told Billy his new name would be “Billie”. I told him that from now on, he would only wear the clothes I gave him. I told him Harold wanted to meet him when he came back from his business trip. I told him that sometimes he would wear the French maids outfit, other times, sexy things. I told him if he had questions about how to dress to just ask me. Billie had shoulder length blond hair and Barb had helped him steal it. I told him to pick out something sexy and we would go out onto the property and discuss his duties.
Billie dressed in a white frilly blouse and short pink skirt, pantyhose and some cute 4 inch high heels. He looked very sexy. He was a little nervous as we went out and strolled around the grounds. I gave him some pointers in how to walk like a woman in high heels. I reminded him again that he had to do what I told him, when I told him. He said, OK, to that but I wanted to test him. As we came around to the front area the landscaping crew was working. I sat down on one of the many benches and pulled Billie down next to me. The landscapers were watching us as we sat together. I be t over and kissed Billie on the lips. We kissed for a long time, our tongues probing each other’s mouths. Then, I said, “Billie, I need you to suck my cock until I come, then eat me”. Billie said the guys were watching. I told him that it turned me on. I layed back, pulling my dress up exposing my legs but hiding my cock. Billie looked at my cock and immediately lowered his face to it. He began sucking me and I must admit, he was pretty good at it. I looked over at the landscapers and noticed they had moved closer, pretending that they were working. It excited me to have them watching and I came at Billie’s blowjob. I spread my legs and told him to eat me, and his lips found my sensitive opening and his tongue skipped into me, eating me like I had asked. I looked up to see that the landscapers had came right over to where Billie and I were putting on a show. They were Hispanic but I knew they were turned on. But I figured Billie had enough fun for one day. We walked hand in hand back to the main house, where I took Billie in my arms and we kissed again while waving at the groundskeepers.
I was ready to teach Billie more of what was expected of him. I made my appointment for my surgery and was ready to move on. Billie asked me about my hormone therapy and said he would like to do what I had done. He asked if he could get tits like I was getting. I told him that would depend on how he did his new job and it would be Harold’s call, but i told him i was sure there would be no problem. Next time, more training for Billie.