I've gotten better at makeup, but on these special days it usually takes me a long time to get it just the way I want. I learned how to apply makeup a few years back when I was traveling on business to Chicago. I went to a wonderful woman who specializes in makeovers for CD's. She was a magician with makeup! I returned several times and after a couple of sessions, even ventured out "en femme" for some shopping with her and one of her assistants. Since then, I've always followed her makeup routine.
On Tuesday, by the time I finally slipped on my black wig I look pretty darned good. I had ordered a real cute red strapless dress with a tulle-hemmed skirt and a matching sash belt with a real pretty bow right in the front. It even had a padded bust which, with the breast enhancers I put in my halter style bra, made me look pretty damn sexy. A silver necklace with a heart-shaped pendant, matching earings and bracelet helped finish off the look I wanted. A few minutes before 5, I dabbed just a bit of "Charlie" perfume behind my ears and on my wrists, slid into my heels and waited for Diane to arrive.
She called promptly at 5 to tell me she was just about 10 minutes away and to make sure I was ready to please her. "I'm very ready" I told her. "Good" she said, "then get my strap-on ready girl. I've been thinking about fucking you all day!" I hurried upstairs to get the supplies ready for her and even took the bed down. Here I was all dolled up and I was likely to end up on the bed within minutes of her arrival.
When Diane walked through the front door, I tried to strike my most seductive pose with my hands on my hips and legs crossed. She kissed me and told me I looked absolutely gorgeous. "You must have been primping all day" she teased, "Now get me a glass of merlot. I want a little fashion show."
After serving her the wine, I had to stand in front of her and model the dress. She made me lift the skirt and show her the red panties and taupe colored thigh highs I had on. "What, no garter belt?" she asked teasingly. Her glass of wine went mostly untouched. A few minutes later we were upstairs and she was making love to me.
She insisted on making love to me while I was still in the dress. "It turns me on to see you like this, and to know how hard you worked to look pretty for me." Being taken while still in the dress and with all my jewelry felt so sexy. It also made me feel wanted and lusted after. Diane took me doggie style at first and then had me lay on my back so that she could lift my legs in the air. It was in this position that I came, careful not to mess my dress. "Let yourself go honey" Diane said, "There's always the dry cleaners!" We had a good laugh at that one.
Diane insisted that I wait until later that night to please her, since she didn't want to ruin my makeup just yet. I would have rather done so right then and there, but I deferred and we made our way downstairs where I could get ready to serve dinner.
Just before dinner, I gave her the Valentine's Day card I bought for her. Inside, there was a gift certificate to a spa located in a very beautiful resort not far from where we live. She loved it and said she couldn't wait to put it to good use.
She paused, looked at me and smiled. "I'm having lunch with Brian on Friday. I thought some freshly manicured nails would look pretty sexy don't you think?" she asked me.
I agreed but didn't know how to express myself. The thought that she would use the gift certificate (or part of it - it was several hundred dollars) to have her nails done for a lunch date with Brian seemed like a slap in the face to me. At the same time, it was also a very symbolic "cuckolding" act for her to do to me. To make matters worse, I was going to be the one setting up the appointment for her.
"Well? Don't you agree?" I looked at her and said "Yes. I always want you to look beautiful."
"You still want to be my cuckold right?" she asked me.
I tried not to hesitate this time and answered "Yes. You know I do."
I'm not sure I sounded convincing. Fantasy may be close to becoming reality. I better be ready to deal with it.
