I Caught a Crossdresser in my House

I came back from a business trip a day early and heard noises from my bed room and when I looked in it was our neighbor’s son dressed in my wife’s clothes’ masturbating. What a rush, I stepped back before he saw me to catch my breath and decide my approach. My wife is very attractive and has sexy clothes and I have seen him looking at her, I just knew he wanted to fuck her, now I wanted to fuck him.
I peaked in again and he had also put on makeup and brought a wig with him that he was wearing. Wow, the wig must mean he is a crossdresser and has done this before for his sexual pleasure.
I walked into the bed room and he saw me and was startled, saying “Oh My God, please, Oh my God!!” He started apologizing and saying all kinds of things and was starting to cry when I told him I was fine with what he was doing and I would never tell anyone about what he was doing. I told him to “trust me and that he looked beautiful, don’t be embarrassed we are friends and it would stay that way”.
I sat down on the edge of the bed and told him I jerked off to adult movies about women and crossdressers in pantyhose and high heels. I asked him, if he ever did also and he said yes, all the time. He asked me if I went to adult movie houses and I said yes. He said he just starts going after he turned 18 and loved the way he could go from one movie to another, lots of different movies.
I told him he had a beautiful cock and I reached out, pulled the skirt back up and put my hand around his cock. He said “oh my god, what are you doing” and I said “what do you think”? The pantyhose were down around his balls and he reached for my hand and said “I don’t know about this? I said “but you have been francizing about this for a long time and being friends we should do this”.
There was more hesitation but I persisted telling him I was going to make him cum and I put my hand up on his throat and held him while I stroked his cock. He was excited and I told him he was and I knew he loved it.
Then I started telling him a story about fucking my wife with him watching and then fucking him. He got hotter and said he would like that and I said I would fuck him without her there and he just moaned and said he did not know about being gay. I told him” the fuck with that, think what you want, you and I know you want it”. I asked if he ever thought of being a bitch or a sissy and he said yes, that he had gotten off thinking about being fucked be a man and that man could be me. That was it; I rolled him over, got lube from my night drawer, lubed his ass, dropped my slacks and started entering his ass. He was crazy with pain and passion and I told him to relax and it would be better. As he relaxed I slowly entered him.
He said “oh my god I am gay” and I said “no, you are a woman getting fucked in the ass”. I was fucking him and I put my hand under him and started stroking his cock against the mattress. I kept pumping him and whispering thoughts in his ear through the wig. I could feel his excitement with his cock in my hand and his quivering body. I looked down and saw his shiny pantyhose legs in high heels and I knew I was going to explode inside his ass. Then he started cumming and a few seconds later I filled his ass.
I stayed on top of him with my cock in his ass and told him we were now far more that friends, we are now lovers. He was pleased with my feelings and said he felt the same way…. More to cum.