It was Darren's 18th birthday last May 23rd. His sister Laura is my best friend since we were in third grade. Darren is not a very good looking boy and was never very good in school. He isn't dumb but long ago I knew he wasn't very smart but was always a good kid while we were growing up. His birthday party was well planned by his parents and myself and another girlfriend Judy, stayed overnight after the party was over. We all liked Darren very much even though we did tease him sometimes. We also took him to the mall with us and took him to the state fair and movies lots of times.
His party was mostly in the afternoon and into the evening hours. He never went to bed until after ten o'clock and Laura, Judy and I decided to scare him by putting sheets over us and bursting into his room. We expected he would be sleeping but when we pushed his bedroom door open he was laying naked on his bed, masturbating. All three of us stood there dumbfounded, seeing him ejaculate. Instead of scaring him we were the ones shocked by it. It was so humiliating for him he began to cry and was so traumatized he didn't know what to do. He rolled over still naked and the best we could do at the time was apologize to him. We stood there telling him how sorry we were as he pulled a cover over himself. I felt so bad about it but there was nothing any of us could do to settle him down. He was so mortified he wouldn't look at us and we tried to tell him it was our fault for coming into his room.
It must have been five or six weeks before he was able to talk to me and Judy and I must have apologized to him five or ten times by then. It was a Saturday months later that he was willing to talk about it with his sister and I, Judy wasn't there that day. We knew he wasn't popular with girls and had yet to ever have a date or a girlfriend. He told us that day that he did masturbate and looked at porn on the computer but also admitted he had never had any sex with a girl. Later that day Judy came over and her Laura and I began talking about Darren and how unhappy and lonely he is. It was Laura who first suggested that me or Judy could have sex with him but both of us adamantly said we could never do that. Then Laura asked us if we would at least masturbate him and again we both refused. It came up in our conversations for a long time and a month or two later Laura told me that Judy did masturbate Darren one weekend when her parents were away.
Laura had told Darren she would masturbate him but because she is his sister he refused, so she talked Judy into doing it. When I questioned Judy about it she told me she had done it to him four times over a few weeks and that Darren was so excited when she did. I have a boyfriend and had jerked him off but did wonder what it would be like to masturbate Darren. Laura kept asking me to and I knew Judy was jerking him more as time went on. It was sometime that September that I told Laura I would do it if Darren wanted me to. By that time Judy had masturbated him a lot of times.
Darren did seem timid with me the first time I touched him but got an erection as soon as I touched his penis. Its small when he is limp but at least six inches when he has an erection. He is so grateful when Judy or I masturbate him but we both know he has no other contact with girls. When Judy and I talked about him he has asked both of us to take our clothes off but we never do. I am not sure how Judy feels about masturbating him but it gives me a degree of power over him. Judy has told me things he likes and I find he enjoys us playing with his testicles as we jerk him. He is also very sensitive in the area between his scrotum and anus and Judy has told me she has penetrated his anus with her fingers often. I have never done that but have seriously thought about doing it to him.
His sister knows when we masturbate him but never tries or wants to watch us. As pathetic as he was that night of his birthday he has become the most submissive person I have ever met. He no longer has any inhibitions of Judy or I seeing him naked and tries to have us masturbate him more often than ever. I keep telling him I will only do it to him a few times a month but I do it more often sometimes only because I feel sorry for him. I know he asks Judy to do it more often but she is more firm with him than I have become. I never admit this but I get aroused myself most of the time knowing how much this satisfies him. I find myself jerking off my boyfriend more often than usual only because I like the way both of them react to it. My boyfriend doesn't know about what Judy and I do to Darren and he never will.
Laura always thanks Judy and I after we masturbate her brother and I know she is very concerned about him. He has had trouble getting jobs and still has never had a girlfriend. He is withdrawn with most of the people he meets yet is so open now with Judy and me. I feel bad for him, but at the same time know how he is so dependent on me and Judy to satisfy him sexually. It amazes me at how submissive he has become and how he allows Judy or I to manipulate him. Judy has told me some odd things she has done to him as far as positions she puts him in and the ways she touches him. I am more subtle about it but do enjoy some of the ways I have him display himself as I masturbate him. Some of the ways we treat him we never tell Laura about. Judy and I do admit to each other that we like to dominate him even though we are the ones satisfying him. He never objects to anything and just a few months ago Judy shaved his pubes. I was surprised the first time I saw him without pubic hair but have never shaved him so far. I don't think Laura knows about that unless Judy told her.