The Next Step - Meeting a Man (Part 1)

I was 20 years old, working after graduation and earning decent money but I still was living at home and had no real desire to move out. Wile no longer close to being passable as a girl I was still dressing at home every evening and weekend.

We had moved back to our home in North Vancouver, my mom and I were still attending the “Mission Traditional Christian Family Church” and she seemed to have a steady stream of men that she was dating and bringing home all of whom she met at the church.

I had started to try to date some girls hat I met in my final year at university but being much younger than them proved to be problematic. In the romance department I was a disaster and I really was not into being the sexual aggressor. By chance I stumbled upon a newspaper at the local magazine store on Lonsdale Ave called the “Vancouver Star Weekly”, it had articles but it’s primary function was for sexually oriented ads focused towards various kinks and fetishes. I bought it religiously for months and loved reading the ads and was amazed at all the different fetishes people had. I hid them in my closet and for the longest time thought my secret stash was indeed secret only to find out later that my mother had found my pile long ago.

By this time in my life I was fantasizing more about men than girls, but I was still unsure of where I was leaning. I loved feminine clothing and dreamed about being touched, kissed and the fact that almost every weekend I could hear my mother having sex I often dreamed about being in her place.

I will never forget it was in early September an ad appeared that basically stated;

“Older, professionally employed widower seeks an effeminate acting younger male under the age of 25. Prefer him to be respectful, shy, soft spoken, enjoy cooking become my house boi and dress like a young girl.”

I was stunned because that sounded like me, but I did not have the guts to answer the ad. The ad appeared for weeks but I just didn’t have the courage until one day my mom approached me holding the newspaper opened to the page with the ad that I had circled. I was mortified but my mom was not angry at all she asked if I had answered the ad I shook my head and when she asked if I wanted to I slowly nodded.

She sat with me and reassured me that part of my love of being a girl also has developed in wanting to be treated like one by a man. I was confused because my Catholic upbringing was dead against homosexuality and at the MTCFC it was so family oriented. After dinner she sat with me and helped me write a response to the ad.

About a week later I received a long letter from a gentleman; he was in his early 60’s, lived alone in West Vancouver, was a semi-retired doctor and he said he was very excited to meet me and that I was the only response he received that he would even consider meeting. His name was Dr. Allen and I was always expected to call him either Dr. Allen or Uncle Allen. He provided me with his telephone number and to call at precisely 9pm on weekdays.

It took me a few days to get the courage to call and I was unbelievably nervous and very timid when I did call. Thankfully he was talkative, was not intimidating and made me feel comfortable. There was no discussion about my desire to be a sissy maid or sex instead he asked me if I would like to go to a Vancouver Canucks game on Friday evening.

He picked me up a couple evenings later at my house and I think he was taken aback when my mother answered the door against my objections. I will never forget my face getting beet red when she invited him inside and reassured him that she knew about his ad and she had no concerns.  Dr. Allen was tall, heavy set, had a friendly face and looked about his age. I can’t say that I felt an attraction towards him, but he was a good-looking man who probably got lots of attention from older women.

That first weekend I went to the hockey game with him on Friday evening on Saturday he took me to the horse races both of which I had never experienced growing up and I was completely at ease with him asking questions about the two sports and talking about my job. When he dropped me off at home on Saturday he invited me to attend the ballet on Sunday afternoon followed by an early dinner at his favorite restaurant.

My mom insisted I wear a suit which I resisted but she relented, and I am glad I did because during dinner Dr. Allen told me that he was very impressed that I chose to wear a suit and that he puts a lot of importance on how a person dresses as well as their table manners at a fancy restaurant. The restaurant was indeed a very formal French restaurant with numerous courses. The meal took hours and we were seated in a quiet booth. This was the first time he asked about my teenage years and love of being dressed like a girl. I was completely embarrassed and when he asked me if I ever fantasized about being with a man my face went red. Before I could even answer he asked if I had ever sucked a man’s cock at the same time he slid his hand onto my thigh.

I shook my head and jumped all at the same time. He went on to explain quietly that he would love it if I would be his sissy maid and stay on weekends.  He told me that I would be expected to do the grocery shopping on Saturday mornings while he saw patients at the hospital then I would be cleaning and cooking for the remained of the day. We talked about the foods he enjoyed and what I liked to cook, it was obvious that he had very high expectations and I would not be cooking easy or simple meals. In return I could wear pretty dresses like I wore growing up and he wanted me to wear French Maid uniforms while doing chores.

I nodded my head and told him I really wanted to be a Sissy Maid. It hit me at that point that I would have to tell my mother because now I would not be home on weekends. I started to have second thoughts, but he reassured me that my mom would be happy for me. He confided that my mother had sent him a separate letter when I wrote him and in it she shared my upbringing with him and they even had spoken on the telephone. I learned later that he was a member of the same golf club as my dad and he had my mother had met at before at club social functions.