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My Sissy, James

Posted by: Author: Age: 52 Posted on: 0 comments
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I had two failed marriages that were my fault. I know I am too outspoken and a dominant person. My attitude and temper has also caused me to lose friends and even family members. I haven't dated in over ten years and actually only have one female friend who is willing to tolerate me. I know I am still attractive and built well for my age, since many men have asked me out. You could say I'm in my own little world and became addicted to masturbation. So much so that I no longer want to get involved with a man although I am not gay. Then young James moved into my house three years ago.


Rita is my only true friend but also has a disposition like me. In 2008 she was involved in a near fatal auto accident and is still today paralysed and in a nursing home. Her husband had died two years earlier and her son James was only 17 when he moved in with me. I didn't want to but Rita begged me to let him live with me. Her mother is still alive but too old and sickly. James is an introvert and easily manipulated. I never had any children and doubt if I could have been a good parent. With Rita's controlling attitude I can see now why James is such a sissy. He was still in high school when he moved in with me and in only a few weeks I could see he was as fearful of me as he was of his mother. James and I would visit Rita every Sunday and he is in tears the minute he sees her despite how she treated him while growing up. I had witnessed her spanking him many times and know his father did also. Aside from that Rita often belittled him and had him completely under her control. After a short time I found myself bossing him around and had little tolerance of what he did wrong. I never hit him but he soon became submissive and fearful of my temper and I had complete control of him.

The first year or so while he was in high school he would stay in his room all night after dinner. I didn't pay much attention to him and could tell he avoided me as much as possible. Last year was the first time I noticed him looking at my body. It wasn't as if I exposed myself to him but I was often in night clothes some of which are rather sheer or short. After living alone all these years I had become lax in my manner of dress while at home. I have been masturbating almost daily for the last ten years and have accumulated an assortment of dildos and have three vibrators.

James was 19 by the time I realized he was looking at my body and never noticed if he had previously. I think I must have been flattered by it always thinking of him as a wimpy kid. I often saw him in his underwear and never objected to him being like that but also had no interest in him whatsoever. I had never intentionally exposed myself to him but know he had seen me in my bra and panties a few times and once saw me with only my panties on. I never thought much of it since it was always accidental. I had seen him naked once but again, not intentionally. I then began to wear my nightshirts around him more often and braless. He tried to pretend he wasn't eyeing me up but just the way he did was arousing to me.

I always had him set the table for dinner and right from the start had him do the dishes every night. I also began to realize he got erections often and he would abruptly sit down so I wouldn't see it. It was amusing to me but also caused me to feel good about my figure aside from arousing me. I began sort of teasing him and would make dinner wearing only my nightshirts. If I think back I'm sure James saw my panties many times as he sat at the table. I often bent over to get pots or pans but always had panties on. So then it began, as every night at dinner time I would make dinner in my nightshirt without panties. I intentionally would walk by James to see if he had an erection. I could see he did sometimes but knew he did when he quickly put his hands on his lap or sat down very fast. I had always been abrupt with him and still am and know how controlling I have been. I soon started to humiliate him by making him stand up when I knew he had an erection. I started scolding him about it and the first few times I did this he actually cried. He was almost 20 years old and all I had to do was act angry for him to be in tears. I knew this was a cruel thing to do to him but found it so stimulating how I exposed myself and caused him to get erections so often.

What I did to him next is shameful but I don't regret doing it. We had finished eating and I put some things away bending over a few times exposing myself. Awhile later James was in his bedroom, the tv was on and as I had done many times previously, pushed open his door slightly trying to catch him masturbating. This was the first time he was jerking off and I just stood there watching him. Except for porn or the one time I saw James naked, this was the first time in over ten years that I saw a guy with an erection. It was arousing to me just watching him as he ejaculated. I wasn't going to at first but decided to let him know I saw him. I pushed the door open and just stared at him. He pulled the sheet up over himself, turned bright red and began crying without me saying a word to him. I don't know how I kept myself from laughing at him. For the first time though I felt bad about how I had treated him since he moved in. I should have felt guilt for the way I had been exposing myself to him but still never regretted doing that. He was pitiful crying and kept telling me he was sorry when it wasn't anything he had done wrong. I sat on the bed and told him so and we talked for over an hour that night. It was without a doubt the longest conversation we had ever had.

The next evening as we ate dinner I again wore a night shirt, sans panties. As we talked I began telling James that I knew he was looking at my body for a long time. I admitted to him that I intentionally started wearing revealing clothes knowing he was getting erections by seeing me that way. I also confessed to being aroused by his interest and the fact that I also masturbated almost everyday and sometimes watched porn on my computer. He just sat there with his jaw open and I think surprised at what I was telling him. I asked him if he enjoyed looking at me and he sheepishly admitted he did.

After he washed the dishes I called him up to my room. I don't know exactly what my intentions were but I began showing him my collection of dildos and explaining how I used them on myself. I could tell he was fascinated when I took out the three vibrators from my dresser drawer. He turned slightly sideways and I just looked at him and asked if he had a hard on. He blushed but thankfully didn't cry and without thinking about it I told him to masturbate for me. The way I said it was more like an intimidating command. I didn't mean it to come out that way but I was so used to ordering or demanding him to do something I'm sure it embarrassed him. I told him to lay on my bed and to take his pants off. His face was fire engine red again but he obeyed me and began masturbating. By this time he had lost his erection and I gave him hand lotion to put on himself. I knew he was humiliated, not just because I was watching him but also the way I spoke to him. It took him a couple minutes before he was able to get a full erection again. I didn't feel bad for telling him to masturbate in front of me but did because of the way I said it. I sat on the bed beside him and pulled his hand away from his penis and I began jerking him off and holding his scrotum. In less than a minute he ejaculated and was moaning loudly. He just lay there for several minutes and then began thanking me. He was no longer embarrassed and looked at me as I watched his penis go limp. His penis is smaller than average I think, but when he has an erection it is 5 or 6 inches. I didn't say anything to him about the size of it. His testicles are rather small but when he did cum there was an awful lot of semen.

After I masturbated him we went to the kitchen and drank some soda and he thanked me three more times. He began asking about my dildos and in particular one of my vibrators. As I sat there telling him how I used them I became wet while all James did was blush. I told him how a dildo and vibrator stimulate me to the extent of having multiple orgasms when I use them. His face turned different shades of red as I explained things and began telling him how I used them anally as well. By talking about it with James after just masturbating him I was totally aroused. I began fingering myself while sitting at the table across from him. I hadn't planned it but looked him straight in the eyes and asked him if he would like to watch me masturbate. He blushed again and only nodded his head that he would. We went back to my bedroom and his eyes were locked on me as I took my nightshirt off. That was the first time he saw me completely naked. I laid on the bed next to the dildos and vibrators but first only began fingering myself. I was the one now in a humiliating position but James was the one who was still blushing as he watched. The only other man who ever watched me masturbate was my second husband many years ago. There I was, like a dog in heat, letting this young man watch as I satisfied myself. Altogether I used two different dildos and my favourite vibrator. I wasn't embarrassed that James was watching me but at the same time knew I was making a fool of myself. Not just how I was exposed to him but by the sounds I made and my reactions when I orgasmed several times. Just seeing his reactions and the expressions on his face was enough to arouse me. When I penetrated my anus with the vibrator his eyes widened and his jaw dropped but he continued to blush the entire time. He didn't touch himself but I could see he had an erection the whole time he was watching me.

The next night we masturbated at the same time watching each other but not touching each other. Then I began masturbating him and always let him watch me satisfy myself. That went on for weeks and even though I had just masturbated him he would again jerk off while watching me. James never asked but I'm sure he was afraid to touch me. He had seen every inch of my body but not once ever asked to touch me. I was and still am abrupt with him and he does whatever I tell him. After a month or so I finally had him use the vibrator on me. I had him kneel on the bed and masturbate me with it as I masturbated him at the same time. He had finally stopped blushing all the time and eventually had him fondling my breasts and fingering me.

Now we masturbate each other all the time, at least four times a week. I have him shave my pubic hair and asked if he wanted me to shave him. He didn't so I just trim it with scissors now and then. What's so funny about James is that he still shows signs of being afraid of me. Just last week he was kneeling beside me on the bed and apologized for cumming on my breast when he ejaculated. He still does the dishes every night and basically does anything I tell him to do. He's a grown man but still a timid sissy. He's never had a girlfriend that I know of and is very shy with everyone. He has yet to ever instigate our masturbation sessions. It is always me who starts it. I simply open his bedroom door and wiggle my finger for him to come to my room. He knows what we are going to do but I always have to tell him to get undressed. He is a strange guy but I'm now happy that he did move in with me. I still visit Rita every Sunday and James usually visits her twice a week. She would die if she knew what her son and I do to each other.



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