As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans.
Lydia could not resist reaching out and squeezing the bulge in my jeans, and her knowing that my cock was encased in satin thong made her hotter that normal. I even unzipped at her request so she could rub the satiny bulge as it pushed its way through the zipper.We were in a booth in the back of the restaurant, and the long tablecloth hid our actions.
On Tuesday we stopped by her friend Queenie's shop; she was glad to see us. While I admired all the sexy clothing, Lydia questioned her about makeup. She left with everything we needed, and I left with an idea. As soon as dinner ended she made me take a shower, shave my body hair and return to her room when I finished; she even furnished me a silk shorty bathrobe to wear.
When I entered her room, there on her dressing table was all the makeup she had purchased at Queenie's. She sat me down and talked me through the whole process of applying makeup. About two hours later, she placed the brunette wig on my head and stepped back to survey the image. "Not bad, and it can only get better."
The days passed. I set my alarm to get me up very early and head to the gym. I returned home just as Lydia was getting up, and, after a shower and breakfast, I would don the stilettos and keep them on my feet while I assisted her in doing the housework. Every evening I practiced applying makeup using the lessons I had already been taught. Lydia stood over my shoulder and assisted if needed. Soon her assistance was not required.
All too soon, her vacation ended and she returned to work. I continued to practice my makeup and walking in my stiletto heels everyday. It was after dinner one night that she dropped a bombshell on me. "I have invited some of the girls from work for cocktails next week," she announced. Why did she bother to tell me this, I wondered, it was her house. "I informed them that Melissa would be serving us drinks." Melissa was the name we decided on for my alter-ego.
That was never discussed. Dressing up for her and going to a Hallowe'en party was one thing. Dressing for her pleasure and mine behind closed doors was another, but this was out of the question and I protested, struggling not to to yell. She tied to placate me. "Your makeup skills have evolved a hundred percent and so has your walking in heels." I was unmoved by the compliments, and bade her good night as I headed for the door. "My friends are like me, and have expressed a desire to see you. I would not allow you to be ridiculed," she added.
She asked me to wait a minute and ran to her room, she returned with the item that changed my mind. It was a French Maid costume, and was the most beautiful garment I had ever seen. This was not some cheap Hallowe'en costume you buy at the local party store; it appeared custom made. "I had Queenie make this for me using your measurements."
I no longer protested, and was getting excited. "So be it," I said. Her smile brightened the room. I wondered what next week would bring.
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<a href="https://www.lushstories.com/stories/crossdressing/my-first-time-part-3-1.aspx">My First Time - Part 3</a>