A Date With [M]yself [20’s][crossdressing][solo][feet][anal]

Please go easy on me, this is my first story! 🤭 I hope you enjoy! 😊❤

For context I’m a 5’5″ bi-curious male weighing in around 200 pounds, a little on the chubby side yet still firm. I looooove crossdressing, but am waaay too shy to go out dolled up! Every now and then I get the strongest compulsion to dress up and go to town on myself, and this was one of those times. 

I woke up that morning determined; that night I was going to treat myself to a date and have a little fun afterwards. My body was still smooth after shaving a couple nights ago, and my toes were painted a lusty glossy black. In the mirror I looked so femme, yet was slightly bummed I couldn’t flaunt it. With a pout I showered up and put on what femme clothes I could; I wore a toe ring on each index toe, a nude thong and nude sheer pantyhose with a cute silver anklet on my right ankle. Over this I slipped on my boy clothes, and headed out the door to start my day.