There in the box was a selection of womans and girls under things, along with some other items I was not sure of, including a well worn pair of handcuffs. My cock twitched when I saw the girls underwear, and I picked out a nice pair and put them on over my very hard cock. I also pulled out a pair of womans underwear and handed it to him with an encouraging look. He was very excited, and told me to put them on him. I leaned down and put them on him, pulling them up to his now rock hard cock. They did not really cover his penis, but I liked how they looked on him. I realized that he was a little chubby in the hips and with the underwear on, his ass looked very feminine. Now he held me at arms length and looked very serious. I want you to do what I ask of you, he said. But if any of this makes you too uncomfortable, just say "I want to stop now M0mmy" and we will stop. Do you understand? I repeated it back to him and he said good. Now the best part. I am going to have you take this mask. As I finished my third glass of wine I then slid on my flesh stockings and silky short yellow dress. As I then applied my make up i heard my sixteen year old son come in downstairs. He shouted up that he brought an old friend back but that he was going out again soon. I put on my high heels and went downstairs.Just then I had a phonecall from my so called date who was cancelling, so I told him never again. I was devasted and went to the kitchen for more wine. On my arrival I couldnt believe that my sons friend Andrew was now a good looking strapping lad. He must be six foot too with good looks too. I sat on the worktop flashing my legs a little no intentionaly at first. He couldnt take his eyes off them and kept trying to glimpse further up. I then realised that there was no wine and Andrew offered to get some more. My son had plans and was going out so I told Andrew to get two bottles. He flashed me a smile as he and my son went off.Twenty minutes later he arrived back. I poured two.
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