by Janae (San Antonio)
My name was Steve. I am 35. I met and started dating Michelle who is my age. We moved in together and for awhile all was fine. I am shorter than Michelle. She is 5'7" and I am 5'5". We both are slim and in good shape. My issue is I am not endowed at all. I also keep my hair over my shoulders. Michelle works as a Executive Secretary while I work from home for a consultant company. Michelle began acting different and our sex life went very cold. She asked me to cut my hair and I rejected her.
She said I looked like a girl and I still told her no haircut. Then one evening we were sitting around and after a few drinks I passed out. When I woke I was completely dressed as a woman. Michelle was laughing and taking pictures. She told me if I did not want the pics sent to my boss I would do as I was told. Twice a week I had to participate in company Zoom meetings. Michelle had me shaving my body. My toenails were kept a pretty hot pink.
No one would have suspected during the virtual meetings that from the waist down how I was dressed. I had on a Spanxx girdle, coffee colored pantyhose, a leather skirt and 3" open toe black pumps. Michelle would video me from a distance and make me watch it afterwards. She laughed and said I would make a good intern secretary. Then one afternoon Michelle took me to her parents for lunch. Her parents are in their early 60's. Bruce and Tina own a top end clothing line and are very rich.
They also did not like me. We got to their 4500 sq ft house and were talking. That is when Tina mentioned she was in a bind as her maid had suddenly quit. Michelle got a big grin on her face and said I bet Steve could help you out. He has alot of free time. I was shocked and caught off guard as they all were looking me over. Tina came and set next to me. She put her hand on my leg and said, what about it Steve, you would look pretty as a maid. I got mad and told them no way.
Michelle laughed and said she had already shown her mother the videos of my Zoom meetings. So to avoid more exposure I ended up with Tina and Michelle in the maids quarters that was above the garage. Tina's maid had left several uniforms and to my disbelief was about my size. In about an hours time I found myself dressed very convincingly as a dutiful maid. Since my body was shaved dressing me was easy. A tight girdle, taupe pantyhose, playtex bra with inserts.
The maid uniform was puffy sleeves, knee length with a princess cut neckline. A lacey white apron tied to my waist. And again 3" open toe pumps. My hair was curled and a face full of make up applied. The finishing touch was my cute maids cap pinned in my hair. To make my shift as Tina and Bruce's maid easier I would take the maids name Amy. From that afternoon I became trapped as their maid. I quit my job and signed a maid contract with Bruce and Tina. My fate as their maid only got worse.
Michelle has a 19 yr old brother Cody. With me being the live in maid I began to see Cody more often. He is average looking and due to his arrogance does not have many friends. I noticed he was hanging around the house more often the longer I was stuck as the maid. Then one night I was awakened in my maids quarter bed by Cody . He had his hand over my mouth and was holding me down. I could not believe how strong he was. He told me he knew I was really Steve but he was attracted to me.
He told me if I wanted to avoid a disasterous scene with his parents I would comply. Cody got into my bed and proceeded to make out with me. He ran his hands all over my body while kissing me. His tongue exploring every inch of my mouth. Then Cody pulled my head to his crotch. His cock hard as a rock slid past my lips and into my mouth. He moaned and called me Amy as he fucked my face. While I was looking into his eyes he ejaculated heavily pulling my head to his crotch. I swallowed all of his cum.
Cody started coming to my room 2-3 nights a week for sex. He really likes taking me doggy style while I am wearing my nighty and high heels. Bruce and Tina would sometimes leave town for several days. Cody started dressing me in his mothers clothes and make me go on dates with him. Him being tall and me so feminized and short we did not attract any attention. He took me to movies and concerts. Always putting me in short skirts and high heels. Eventually Cody told Bruce and Tina about me.
They thought it was great. They did not have to worry about Cody getting someone pregnant. So now Cody takes me out and I have to act like a 19 yr old girl in front of Bruce and Tina. Tina has actually started making me practice with her to develop my teen girl attitude. And like, I think it is working. I love my job as Bruce and Tina's maid.
Cody is super nice to me and he has such a big cock. Cody has a sister named Michelle who comes over with her boyfriend every once in awhile. She always tells me how pretty I am. Sometimes I think I have met her before.
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