Friday had been an interesting day cleaning, what with three chance encounters. I just knew that Saturday was going to be equally as interesting… and I was right.
I spent the morning shopping for groceries and doing some laundry. I still didn’t know what I was going to be wearing that night as Linda had said anything yet. She had me stop at the dry cleaners and pick up her clothes. I noticed her favorite outfit was among the bunch. When I got home she had me hang up everything except that outfit so I knew she was going to wear it for dinner. She was going all out to look good for Darryl.
I set the table for three, started the food that would require long cooking and then headed for the bedroom to get dressed. Linda had just come out of the shower and asked me to help her get ready. I was shocked when she pulled out her underwear as she had selected her sexiest stuff: matching set of bra, panty, and garter belt along with black hose. I asked her why she was wearing something that sexy just for dinner at home. “A woman likes to feel her best when entertaining a male guest. Maybe someday you will get to experience that. Nothing makes you feel your best then knowing that you have sexy undies on,” she replied with a smile.
“Are you planning on letting Darryl see them?” I enquired.
“Would that bother you?” she purred as she walked by me and back into the bathroom before I could reply. From there she called out my clothing requirements for the evening. I paled as I heard her orders.
“I want you to wear your pink bra and panty set, the white linen slacks and the pale pink and white blouse. Wear your new sandals, the ones with the 2” heels.” So she was planning on me being dressed as
“What are you doing?” she asked as she slipped on the thin red dress which showed off her cleavage and lots of leg.
“I was going to put on my make-up since you want me to dress like
“No, just wear the clothing I told you, no make-up or wig tonight.”
I couldn’t believe it. She wanted me to wear a feminine outfit, one that my pink panty and bra would show through. But I was not to complete the look with make-up and hair. I would look as neither a guy or a woman, but in between; a total sissy. This is how she was going to embarrass me in front of Darryl, by not allowing me to go totally in either direction but instead in the middle like some kind of freak.
I got dressed and looked in the mirror to see the sissy looking back. My face was bright red, and I was sure it would stay that way all night. Resigned, I headed to the kitchen to finish cooking. Linda came in and told me to put an apron on so as not to get my clothes dirty. She smiled as I pulled out a pink apron to match my outfit.
An hour later I heard the doorbell ring and knew that Darryl was here. I heard Linda answer it and let him in. There were a few words of welcome followed by a disconcerting moment of quiet. I didn’t dare think about what that meant. Then I heard the footsteps approach the kitchen followed by Darryl saying “cute” as he saw me cooking. I turned and smiled, took a few steps to shake his hand while I watched his eyes travel up and down my body taking in my feminine presentation. Then he really surprised me. Instead of shaking my hand as we had done many times, he stepped closer and gave me a hug complete with a kiss on the cheek.
“My, you certainly look nice tonight.” He proclaimed. Linda stepped up beside him and rested a hand on his shoulder. “She should be doing that to me as a sign of support, not to him” I thought.
My eyes grew wide as I watched Darryl step back away from me and slide his arm around Linda’s waist as if claiming her. She didn’t step away as she asked me how dinner was coming. I told her it would be another fifteen minutes. She said that they were going to sit in the living room while finished up. They never let go of each other as they walked away. I turned back to my cooking, trying to take my mind off of what had just happened. Oh, it was going to be a long night.