My friend's father, Mr Webster, had turned out to be anything but the pillar of the community he pretended to be. Despite his regular Sunday church attendance with Mrs Webster, it transpired he also enjoyed the company of other men. He was certainly enjoying me, and within a few weeks I had fallen into the role of his sissy girlfriend and was acting accordingly.
Discretion was obviously important to him so when I was visiting my school friend, Mr Webster would slip me a little note with a place and time to meet and I would confirm with a nod or a wink if it suited. Typically that would be a quiet corner of town and I would keep low in the passenger seat until he had driven well out of town, then he would find a lonely layby or forest carpark and I would change into one of his preferred outfits. His favourite was my schoolgirl outfit, black pleated skirt and white blouse, with the black stockings, suspenders and black Mary Jane heels he had bought for me. I had been experimenting with makeup too and, being a tad effeminate, was quite passable as a girl.
When I was dressed I always felt excited and couldn't wait to take my mature lover's large penis into my mouth. Mr Webster informed me that his wife performed oral sex on him but wouldn't allow him to ejaculate in her mouth. I was only too happy to perform that duty for him and enjoyed fellating him in the drivers seat until his semen filled my throat.
I was happy with this arrangement as it fulfilled my love of crossdressing and desire for cock but after a few meetings Mr Webster informed me that he wanted to try something else...
One evening he drove me to a forest far from town and parked a half mile or so up a secluded lane in the middle of a heavily wooded area. I was feeling deliciously feminine in my schoolgirl skirt and sheer stockings, this time with a pair of black stiletto pumps. He told me to get out of the car and led me by the arm into the trees. He was carrying a pillow and a little plastic box, the purpose of which escaped me.
[M] Trans Pool Party