Life Lesson #1: Older Guys Are Fun!

At this point I was basically keeping myself smooth from the neck down on a full time basis, so all I needed to do was apply my makeup, shake out my wig, and get a dress on. I douched quickly before starting my makeup. The makeup was (and is still) the hardest part of my routine, so I didn’t present very well that night. For my outfit, I chose light pink panties with lace strappy sides and a matching bra. I had pads safety pinned inside the bra cups to fill out my top. I squirted a bit of lubricant deep into my ass using a syringe applicator I kept around just in case. I chose a form fitting black cocktail dress with a white collar, what I called my Audrey Hepburn dress, and a pair of black 5 inch heels. My legs were freshly shaven just before Jones showed up, so I skipped the stockings and went with bare legs. At the time my go to wig was a straight, auburn color with bangs that swept to one side (very 90s) and length down to the center of my back.

I walked into the living room and found Jones sitting on the couch. As soon as he saw me his eyes narrowed and a sly smile crossed his face. I’d never been on the receiving end of a look like that from a man; but I liked it. I turned off the living room light, leaving only the glow from the hallway light and television. I figured the low light would help cover my half-assed makeup situation. I sat down on the couch next to Jones and we talked a bit. He complemented my hair and my dress as I did my best to keep a feminine voice through the conversation. I wasn’t perfect by any means; but I could tell Jones was down to play pretend with me anyway.

Jones leaned in to kiss me and I guess because of the age difference or something, I was startled a bit; but let it happen. He moved to my neck and then my ear lobes, when one of my clip on earrings popped off and fell in between the couch cushion. He didn’t stop when the earring fell and I could feel his hand rest on my knee, then slowly slide up the top of my thigh.