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A 22 Year Old Wealthy, Weird, Wimp

Posted by: Author: Age: 28 Posted on: 0 comments
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I've gotten myself involved in something that has become very arousing to me but am too ashamed to tell my boyfriend about it. All together there are five other girls involved and we all like to participate in humiliating Keith.


My best friend Heather is a very pretty girl and knows it. She uses guys whenever she can get them to pay for things and manipulating them into buying her gifts. She began dating Keith last year and the first time I saw him I was stunned that Heather would date such a wimpy guy. I found out he was from a very wealthy family and absolutely adored Heather. He isn't the least bit handsome, isn't very tall, a total dork and only 22. Heather admitted she was only using him and within the first few weeks he began adorning her with expensive gifts. They went to the best restaurants and he treats her like a queen. Since last April he has taken her to Las Vegas, Cancun, Niagra Falls, many times to the Outer Banks and just recently been on a cruise. She began telling me about her sex with him and she laughed as she told me she had him completely under her control. She said he was the weirdest guy she ever went out with and she could do anything she wanted to do to him. Heather told me details sometimes of how she would humiliate him and said his favorite thing was to have her masturbate him. She also said he preferred just feeling her up and masturbating her instead of intercourse.

Each time I saw Heather she would tell me more derogatory things about Keith. She enjoyed demeaning him and said how she would shave his pubic hair and had began using a dildo to penetrate him as she masturbated him. It seemed she did everything she could to embarrass him and get him to dislike her. She really has no loving feelings for him and it was so obvious she was only taking advantage of him.

It was last July when Heather called me and asked me to come over to her apartment. When I came in she took me into her bedroom. There was Keith, tied down spread eagle and naked on the bed. As soon as he saw me he turned fire engine red. Heather did tell him she asked me to come over and that she wanted me to see him naked. His penis was just as small as Heather had told me about and a few times it looked as though he wanted to cry. His embarrassment was obvious but after a few minutes she told Keith to tell me whose idea it was to expose him to me.

Keith then said he is the one who asked Heather to do this. I thought it strange since Keith is not built very well and the size of his penis isn't anything to be proud of. It's not tiny but far from large. Over the next hour or so Heather had me sit and watch as she kept playing with his genitals letting him get hard then leaving him get soft a few times and starting all over. He finally begged her to make him cum and I couldn't believe what a wimp this guy really is. Heather then inserted a dildo into him and proceeded to masturbate him. He had no pubic hair and oddly no body hair at all. Heather was shaving all his body hair and he doesn't even have hair under his arms. After the first half hour she untied him and forced him into different positions as she played with his genitals. When she told him to get on his hands and knees he pleaded with her not to expose him like that but she ordered him to and he reluctantly obeyed. He was on his knees with his head on a pillow with his rear facing me and Heather. That's when she satisfied him jerking him off and putting the dildo in him. I couldn't believe he let her do all this to him while I was there. As I was leaving Heather told me she was even going to spank him after I leave. I didn't know whether to believe her but soon found out she wasn't lying.

About a week later she asked me to come over again and told me she was going to have another friend there to watch. When I got there it was Peggy who let me in and right away we began laughing about it. When we went into the bedroom Keith was naked but this time not tied down. Heather first began shaving his pubic area and right away Keith got hard. What I don't understand is the way Keith is so embarrassed, why would he let Heather's friends watch her do this to him. She had plastic sheeting on the bed and made him kneel down again with his butt up but this time only to shave his rear and around his anus. I can't think of a more humiliating or degrading way to be exposed but the entire time Keith was aroused.

Heather kept touching and playing with his penis and testicles while shaving his butt crack. After shaving him she took out a small strap and spanked him for about ten minutes. She wasn't hitting him very hard but again he remained aroused while she did this. In betweeen swats with the strap she would hold his penis and insert the dildo into him then take it out and swat him again. It was amusing to me but also in a way arousing me. It is something I never dreamed of to do to a boy. I know my boyfriend would never put up with such a thing. It was evident that this entire thing was humiliating to Keith but he did whatever Heather told him. He seldom spoke and did only when Heather asked him a question and most of his answers were 'yes' or 'please'. This was the first time Peggy saw this done to him and she just kept shaking her head when she looked at me. He did cum twice this time and Heather constantly called him a good boy. I just can't imagine anyone, whether male or female, that would allow themself to be so degraded. I know I would be completely mortified if my boyfriend exposed me the way Heather does to Keith. Peggy and I agree that Keith really is embarrassed but also think it is part of his excitement and probably a fetish he has.

By the end of last August four other girls had watched Heather do these things to Keith. There are a total of six of us who watch three to five times a month. One night in January there were four of us there at the same time and since last summer Peggy began either masturbating Keith or putting the dildo in him. One other girl does it also but as many times as Heather has asked me if I want to do anything I have only masturbated him once. I would rather just watch the things done to him and it does arouse me enough that I often masturbate when I get home. Heather likes humiliating him and I suppose Keith himself likes the idea of being embarrassed. I don't think he ever expected Heather to get this many girls to watch him being made a fool of.

Lately there is always three or four of us there and all I have to do is look at Keith's face to realize he is truly humiliated. He avoids eye contact with all of us but does erverything Heather wants him to do regardless of how degrading it is. Peggy even shaves him somtimes but he will never look at her when she does. He remains stimulated all the time and usually cums twice every time I am there. I just can't comprehend how a guy could allow himself to be treated like this with an audience each time. Heather sometimes humiliates him verbally. She makes him answer demeaning questions, things about his penis size, how it feels to have a dildo in him or if he likes the girls watching him. She'll ask what position he hates being exposed in the most and then makes him do it. She always has him on his kness during these sessions and his anus, penis and scrotum are in full view to us. He admits he is most embarrassed this way but also knows Heather will tell him to get on his knees with his butt up. When he answers these questions his voice quivers and he stutters with embarrassment. He continues to adore Heather and has no conception of how she talks about him behind his back. As she does all these things to him she grins at us constantly and I can tell she enjoys treating him this way. A few weeks ago he bought her diamond earrings that have to be worth a few thousand dollars. Next month he is taking her to Atlantic City for four nights and he still thinks she is 24 but she will be 29 in May. She has him wrapped around her little finger and he doesn't know she thinks he is a fool and likes the idea of humiliating him as much as she can. He evidently likes it though which I can't understand.



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