Making of a new Sissy

I became a Sissy at the hands of a friend of my parents. When they worked long hours they would normally ask a friend to check in on me to see if I was OK, despite the fact I was at this point 18. One time it was Tom who came over. He was mid 40's, an old friend of my dad's. A guy who always seemed OK enough, nice guy type of older man the parents knew. This time he came around he said that my parents would be out until late and had asked him to stay until they came back. Nothing out of the normal, kind of thing that had happened a few times over the years, admittedly not as much as now I was older though.

It had gone about 8.30pm and I told Tom I was going up to grab a shower and would be back down soon. After I got out of the bathroom and back to my room to dry off and get changed, only then did I notice the outfit out for me on the bed...a little red dress, black thong, stockings and a blonde wig too. WTF was this? Was it Tom? Whats he expecting here? Now admittedly I had searched a few trans and CD sites while I got a little more curious when home alone and had enjoyed them, but never imagined being anything but the guy fucking these girls, but this outfit did look good & my mind started to wonder what it might be like wearing this kind of thing.

I crept to the top of the stairs and went down a few to be able to look into the front room, managing to catch a glimpse of Tom, cock out and slowly stroking to whatever he was watching on the TV. Before I knew what I was doing I was calling his name, he opened the door cock still out and just stared at me with a look of 'What?' He then explained after Dad has asked him to take a look at the computer he saw a few of the sites that had been visited and if I didn't want him explaining all to them, I would be back upstairs and only down when I looked a lot different than I currently was. There was no way I wanted him telling anyone of what I'd been checking out and figured that putting some stuff on was the lesser of 2 problems I could have here.