What I write below is a true story of my first time out as Jessi and everyone is at least 21, but most are much much older.
Understand while I would not call myself a prude, I have never been a slut. At 48 (basically married for 20 of them) I’ve had three female partners, one male one night stand, and one regular hook up. While I have done some wild things with some of them, bondage, blindfold, spanking, I’ve never really let go. With my regular hookup I’ve played around with Crossdressing. But never tried to be passable. But over the last six months I’ve fooled around with makeup, heels, nail polish, and a few nice outfits.
Last night changed all that. I knew there was a party Friday night at the Red Barn in Berlin New Jersey, and T-girls and CD got in free. So, I kept myself horny all week and decided I was going to drive the hour down there and let myself have some fun. I went to work in a red lace thong to keep myself horny all day. I came home from work and immediately showered and shaved. As I am doing this my regular hookup, who due to mutual scheduling issues, we haven’t met in over a year, called, and said he was free tonight. I told him I was getting ready for a party and would send him a picture as soon as I was ready and could head to his place first if he liked what he saw.