Jessy the tranny

I was in my attic looking for lamp that I had stored for my sister. It was getting hot so I decided to open a couple of dormer windows to let some air flow. When I opened the last of the thee windows which was on the back of the house I could hear music coming from my neighbors back yard. I knew that they had just left for a 2 week trip to Europe and only their 19 year old son, Jessy, was home so I was a bit surprised to see a sexy young lady laying on her stomach sunning by the pool in a pink thong.

I used my camera and snapped a few pics, I zoomed in and was able to get some pretty good ones. She raised up on her arms and rolled over.,,, wasn't a girl, it was Jessy and the thong just barley covered him. I took a few more pics and decided to go back to my search.

After cleaning up and finally getting to sit down with my lap top I downloaded the pics to get a better look. Jessy was slim, shoulder length light blond hair and only 5ft 7 or so. The pink thong splitting his cheeks made his ass look so girlish. I felt my cock stir a little then I noticed that in the pics of his front side that he was wearing panties, They had a lace front panel and I could just make out the out line of his dick. My cock was hard now. I had never looked at him close enough to realize just how feminine he was.

I decided that I was going to get him to come over and just see if he might be interested in getting to know a middle aged man a little better. I called and gave him a made up story about moving some furniture around and asked if he could help and he was willing. I left my lap top opened on the kitchen with one of the pics of his sweet ass on the screen . I had cropped out most of the surrounding details so that he wouldn't recognize himself, I wanted him to see it and I hoped he would give me a reaction to it.

He rang the front door bell and as soon as he came in I directed him to the guest room and we rearranged the furniture, and had worked up a little sweat so I offered him a cold drink and we went to the kitchen. I grabbed us both a glass and was filling them with ice.and just making conversation, I noticed he was glancing at the pic on the screen and trying not to be noticed so I just said, nice ass, ain't it! and handed him his glass. He smiled and said hell yes! He asked , got any more of her. I said a few and told him to sit down and take a look, the mouse is right there.

He clicked on the next three pics, they were all of him face down, he hadn't realized yet who it was and then the next one was of him on his back and at that point I could see his cheeks starting to turn a little pink then the next pic and the next. At that point I said, nice panties, who's are they? He stuttered a little and then went silent. I said relax, no need to worry, I will keep them to myself as long as you will just answer a few questions for me, now, who's panties? Well, moms, he looked ashamed and I put my hand on he shoulder and tried to assure him that it was ok. You look very sexy in them. Do you ever wear anything else of hers? Well, he was starting to relax a little, She has some thigh highs and heels that I like to put on when I I can. I said nice, I bet you look very hot in them. My cock was semi hard in my loose shorts and I was standing beside him. He noticed and started to try to leave. I said Jessy, there is no reason to be ashamed or scared, its our secrete for now, I could help you get some of your own things and you could keep them here so your mom and dad wouldn't find out. He said I need to go, OK you think about it and when you ready to talk some more just let me know.

He called about noon the next day, Mr Johns, can we talk about yesterday, I said sure. He started to say something and I cut him off and said just slip into that sexy pink thong and come on over. Can we talk about it over the phone, I said when your ready to talk, come on over.and hung up.

A couple of hours passed and I was thinking that maybe he wasn't going to show but there was a knock at the front door, a very weak knock. I answered it and he said may I come in, sure, if your wearing what I told you too. He kinda hung his head a little and stepped in past me and waited. I closed the door and said perk up, go make yourself comfortable on the couch so we can talk, I sat in a chair across from him and said, Whats on your mind? Jessy started to speak and I said wait, first show me the the back of you thong I want to be sure you are ready to talk. He stood up, turned his sexy little ass to me and pulled the top of his shorts down a little, That's nice, now whats on your mind. He started going on about how bad it would be if anyone found out and how his mom and dad would disown him, etc and will you please delete those pics?

I asked, is that the only reason you came over here? I was hoping you might have wanted to tell me more about what you do when you dress up. You know, talk about IT. He blushed a little and softly said what do you want to know. Have you ever let a girl friend see you in panties. He said, I have never had a girlfriend. You ever had a boyfriend? He blushed a little more and said no. I said its ok, I just want to get to know you better, relax, were just two guys shooting the shit here. Hell, after my wife died several years ago I decided to try new things, I have had several bi experiences. No big deal, your safe I wont tell anybody. He seemed to relax a little. He started, I love the way I feel when I am dressed up. I feel sexy. I asked a few questions, Do you ever smell your moms panties, or even taste them, when I was young I did. He was letting down his guard and starting to talk a little and I said, I would love to see you in that thong right now. He stood up and pulled off his shirt and then slowly pulled down his shorts. They fell to the floor and he stood there. I looked him over top to bottom. He didn't have a single hair on his body. His cock was little and it was hard as a rock. I told him to turn around and he did as he was told. You are very sexy. Spread your legs a little and bend over for me, show me that sweet ass baby.

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