This past weekend I stopped by my buddy's house to check on things while they were away, as they had requested. It didn't seem that either of the boys were home so I decided to snoop around and went upstairs. I happened upon my best friend's youngest son wearing his mother's lingerie, in full makeup, wig and all. He was watching porn on his laptop and nearly fainted when he finally noticed me watching him masturbate to a video of a crossdresser sucking cock. He was very frightened until I assured him his secret was safe with me. I complimented him on his appearance and asked him if he was interested in sucking my cock. His eyes went wide and he became quite nervous. I assured him that he didn't have to unless he wanted to suck me.

I decided to try and seduce him, I wanted his painted lips around my cock. I went across the hall into his parent's room and selected a little black dress his Mom was wearing when she sucked my cock one very drunk night. My plan was to have her son wear it while my cock was in his mouth. He sheepishly agreed and looked cute as hell as he slipped on the tight dress. I had him model it for me and after I had him turn slowly on his heels, I pulled out my stiff cock and reached for his arm, gently guiding him to his knees before me. Any apprehension seemed to disappear as he willingly wrapped his ruby red lips softly around the head of my cock. Slowly at first he took my hard dick in his mouth. Then he pulled off and licked up and down the length of my rod, teasing the tip with his tongue. I took his head in my hands and forced my cock deep and made him gag a bit as I skull fucked him just like his Mom.

I relaxed my grip and let him take my cock as he wanted. He lovingly licked and sucked my cock as if he been doing it all his life. My first spurt of cum startled him and he gagged and pulled off as it hit the back of his throat. I came again across his chin and he opened his mouth and I finished on his tongue. He got very anxious and almost ripped off his mother's dress. He was scared and full of remorse. I calmed him down with soft kisses and began massaging his tight hole. I lightly penetrated his pulsing asshole with a finger and he came violently all over his mother's dress and stockings. I gave him a deep kiss and we both agreed to do it again. I'm looking forward to him getting his first driver's license next month.