I finally found her big two story house and knocked. Mrs. Elliott answered the door. She was beautiful. She smiled and invited me in.

She showed the room to me and told me, I would be sharing it with her 18 year old son and I thought it would be perfect as I am only twenty.

The room had two double beds and an adjoining bathroom. The price she quoted for the room was about half of what she could have rented it for, but who am I to argue.

We sat and chatted for a while and she made us a strong drink. Then she said she wanted to tell me something before I committed myself to the room.

She then moved closer to me and started to tell me about her son Joe. He is a closet sissy and he is very lonely and unhappy and that she was hoping I would draw him out of his shell. She told me that she knew he is taking and wearing her panties and nighties when she was not home but that he was unaware that she knew about it. I was really tenting my pants as she told me about it and she reached down and fondled me. We spent the rest of the day in her bed. She was absolutely wild.

I went to my hotel to pick up my suitcases, knowing my mission was clear. I was to bring out the sissy in Joe Elliott and gently guide him into happiness.

When I returned to the house Joe was there, in fact he helped me get my stuff to the room. He was a very good looking young man. Short and a little chubby but very neatly dressed. He sat on his bed and we chatted as I unpacked. It was late when I got squared away and I told Joe I was going to shower and go to bed. I undressed and went into the shower and I could feel his eyes on me.

"I sleep in the nude joe will that bother you?"

He assured me it would not bother him, so I finished drying my body and then slipped into bed. In the middle of the night I had to go potty and when I returned to bed I made sure the covers would not be hiding my body.

I woke with my usual morning wood and was just laying there pretending to be asleep when mom called us to breakfast. I hopped up and dressed in a hurry and Joe and I went to breakfast. Mom looked wonderful, she was wearing a pretty nightie and matching robe. I sure wanted to get some more of that.

Joe and I sat around and talked and since it was Saturday we decided to go clubbing that evening. We got to the bar and I asked Joe what he wanted and he told me he does not drink, so I ordered him a long island ice tea. Needless to say after a couple of them he was totaled. I managed to get him home and up to our room. He sprawled on the bed fully clothed as I undressed. It became apparent that I would have to undress him or he would sleep in his clothes. I sat on the edge of the bed, naked and slowly removed his shoes and socks. I massaged his feet and toes in an attempt to get him to wake. No luck, I slowly unbuttoned his shirt and my hands touched his little nipples as I removed the shirt. He moaned but still did not wake, at least I did not think he was awake. I gently pinched one of his chubby little titties as I fondled the other one and he continued to act as if he were asleep but I could see his penis was hard. His nipples hardened and I bent down and nursed on one for a few minutes. He had nice little titties, at least an A cup, I made a mental note that we would have to get him some bras.

Time to take off his pants. I opening the belt and pulled down the zipper, and slowly pulled them off, I noticed he was tenting his tight white jockies. I reached up and pulled them down, making sure my hand felt his hard penis as I did it. I sat there looking at him sleeping and gazing at his 4 inch cut penis. Giving it a squeeze, I started covering him and he started to cry.

He told me how lonely his life had been and how lonely he was and asked me to keep him company in his bed. I spooned in behind him and put my arms around him. My hand moved to his hard little penis and I slowly fondled it as he talked to me. My other hand was gently squeezing and touching his hard little nipples. He told me how happy he was to be with me. I kissed his neck as I touched him and my 8 inch cut cock pressed into his cute little ass crack.

I reached over to the night stand and got the tube of lube I had placed there. He spread his legs and I slowly lubed his tight behind. I rolled him over on his back and moved over him. As I bent down to kiss him I slowly started to press into him. He moaned and I stopped and he begged me to keep going. I did not want to hurt him so I went as slow as I could until I was deep inside him. I slowly fucked him as I kissed his lips and sucked on his chubby little boy titties. Finally we had a mutual climax. I collapsed exhausted and held him tight.

Needless to say we did not get much sleep that night. We awoke when mom called us to breakfast. He was cuddled in my arms. He seemed like a new person as we chatted at the breakfast table. He had to hurry off to work and mom and I sat around and discussed what happened.

We both were turned on so much that nothing got done that day. She showed me some pretty clothes she had purchased for Joe but never had the nerve to give him. Panties, nighties, robes and more.

Joe returned from work and we had a nice dinner. Later in the evening when mom was out of ear shot I told him to get ready for bed and that I had put a nice present on the bed for him, and I wanted him to wear it tonight. He went to the room and saw the pretty pink nightie and silky pink panties I had put out for him. I also had put the matching robe and slippers on the chair where he could see them. When I went to bed an hour later he was dressed in his pretties and waiting for me.

The next morning, instead of mom calling us to breakfast, she just barged into the room with coffee. She saw us in bed together with Joe dressed in his pretty nightie and me spooned up against him, holding him in my arms. She told us breakfast was getting cold and put Joe’s robe and slippers on the bed and said to hurry down. Joe was so humiliated that his mother had seen what he was wearing and that she knew he was gay. I then told him she had arranged the entire thing. He was mortified that she knew, but it also excited him beyond belief. I helped him put on the robe and then after jumping into my pajamas I led her down to breakfast.

To be continued