Sex Ed Chapter Two

Over another drink, I learnt how David Lawrence had been dressing up as a girl since he was a teenager, always keeping it secret from his family and what few friends he'd had. He was shy around women and sex and had never had a girlfriend, instead he'd buried himself in his studies and dressing as a girl at home and jerking off to his fantasies. Since starting work as a teacher at my son's school, his feminine wardrobe had expanded greatly and he had become pretty skilled at looking and acting like a girl.

Tonight was the night that he had decided to throw caution to the wind and go out dressed as Cindy. He/she said that he didn't exactly feel like he was a girl but he knew that as Cindy he felt much sexier and more comfortable than as David and that he wanted to experiment with the possibilities being Cindy could bring him. He had always liked women, he was pretty sure of that (and so was I given how quickly I was able to bring him off in the toilet cubicle), and had always lusted after them even as he envied them their beautiful outfits. At the same time, a lot of his fantasies involved Cindy being taken by a hot, studly man, and although he had never acted on these either, he was quite curious about it. I told him my plan for what I wanted from Cindy and he was happy to oblige after very little persuasion from me.

You may remember how I told you that my husband, Terry, objected to my desire for a threesome with another guy even as he encouraged me to bring home girls for one and even as I could tell how turned on he was by my tales of guys that fucked me. Needless to say, I thought gorgeous, sexy but hung Cindy could be just the one to bring my husband around to sucking cock. For once, I didn't give him all the juicy details of one of my sexual adventures. Instead I told him that I had a surprise for him, that I had met a very special girl in a bar and that I had invited her around to have a bit of fun with the two of us. I could tell that he was already pretty excited by the prospect.