My step brother is 5 years younger than I am and he has had a crush on me since he was 14. He started wearing my panties and thought I would never catch on. Soon enough I found out and told him he could continue if he wanted but would soon have to get his own. Once he hit 18 our relationship took a turn to a new level. He was sitting on my bed talking to me one night and I noticed he had a pair of panties on under his pajamas. I asked him if they were mine or his and he admitted that he had borrowed a pair of mine. I asked him to take his pajamas off so he could be more comfortable. He did and soon the two of us were laying on my bed talking and the conversation was gradually getting more and more erotic. I started by asking him what it felt like to wear panties and he was very candid in his explanation. I had on a terrycloth robe from after a shower but had put on a bra and a thong under neath. I nonchalantly let the robe fall open so he could see my thong panties. Although he was talking to me his gaze was on my panties and I also noticed he was getting a very prominent boner. After a couple minutes I put my hand on his cock through the nylon panties and said to him "what have we here." He just gave a little moan so I continued to stroke it very lightly. I had never seen a guy cum or jerk off and figured now was my chance. he rolled over on his back as I continued to stroke him. I finally pulled the panties down and took his cock in my hand and slowly stroked it. He was really getting hot, moaning and writhing around so I slowly stepped up the pace. Pretty soon he gasped "I'm going to cum." I kept stroking and in a few seconds he started jerking and then the white cum shot out of his cock and over my hand.I decided then that I wanted to control him and I knew he would let me.Well, over the next few weeks I discovered that he was masturbating several times a day. Every few days I'd have him join me in my bed and I'd give him a hand job. One day I told him I wanted to watch him jerk off and he readily obliged. I then asks him how often he did it and he admitted he was having a problem because he couldn't stop. He admitted to jerking off at least twice each night and 5 or 6 times during the day. He told me he wore rubbers so that he wouldn't leave mess whenever he came. I told him one day that I thought it was time he did something about the chronic masturbation and asked if he wanted my help. He agreed but didn't know how I could help since he admitted I was part of the reason he was jerking off so much. A few days later I had him come into my bedroom. I asked him to take off his clothes. He removed his jeans and I saw he was wearing a pair of white nylon panties with lace trim. I had him pull down the panties and stand in front of me. Then I reached into my purse and produced a chastity device I had ordered for him. 'This is a chastity device, also called a cock cage and you are going to wear it to help you stop jerking off. I'll allow you to cum at least once a week but the rest of the time I will have the key. Now put the cock ring on and we'll get you all locked in." He put the cock ring on and then I took the cage and after putting some lube on his semi hard cock I inserted it into the cage and then attached it to the ring. I then gave him the lock and showed him how to put it on the device. "I want you to lock it and then give me the key." He obeyed me and then gave me the key. That night I had him sleep in my bed for the first time. I had him wear a pair of my panty briefs which I'll admit was a bit sadistic because it only made him hornier. He wore the cock cage every day and admitted he wanted to jerk off but knew he couldn't. On Friday night I told him that since he'd worn it for 6 days I'd take the cage off for him to be able to cum. I unlocked it and removed the cage after pulling down the panties he had on. His cock immediately went rock hard and stood up straight. I asked him if he wanted to jerk off and without a word he started to stroke his cock. Pretty soon he had shot cum all over the panties and on his groin. After he came we both lay there for a long time and then he was getting hard again. I don't know what made me do it but I simply bent over him and took his cock in my mouth. He about went crazy with that and it didn't take long before he came in my mouth.after a while I told him I had to put his cock back in the cage. He didn't resist. I told him that every week if he was good I'd give him a special treat. This has been going on now for several weeks. He's caged all week night and day but on Fridays he gets his reward. My plan is to slowly turn him into my subordinate along with feminization and discipline. I've hinted at this and judging by his responses I think he's not only ready but eager.