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Old 04-28-2009
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I think most of the guilt comes from the "What would ___ think if they found out?" type of paranoia. I have two kids (24/17) and there is no way I would feel comfortable with them knowing. Then again, if i had a gf who was into anal or bondage or midgets or whatever, I would not let them know that either. So I can attribute part of the guilt to it being something that i have to hide.

On the other hand, i think it runs deeper, but I cannot put my finger on where.
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Old 04-28-2009
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Default guilt

Psychologists generally agree that guilt is the state where you experience some sort of conflict at having either done something you believe you shouldn't have done, or having failed to do something you believe you should have done. In the former, the "shouldn't have done" may be related to a moral standard, which can be established at any level from individual to societal. In Western society, particularly in the United States (with its abhorrent Puritan history), morality is all too often associated with matters sexual, as opposed to truly immoral things that are prevalent in U.S. society, such as poverty, the absence of social safety nets, and so on.

In my view, an examination of feelings of guilt about having had sex with a transsexual ought to begin with an assessment of whether the "guilty" party feels that she or he has done something wrong. If the answer is yes, the next step ought to be to assess whether "wrong" is an external imposition that can be ignored (for instance, a church's admonition against premarital sex) or one that the person genuinely believes to be true. If not, the guilt is most likely about violating some arbitrary, and unnecessary, "moral standard" that involves others telling us what we can and cannot enjoy. The guilt may, though, be about violating trust. For instance, having sex with a transsexual may make one feel guilty, but not because it involves a transsexual but because it involves "cheating" on, say, a spouse.

In all of this it is worth keeping the differrences in mind. Freud wrote of guilt as being the result of internal conflicts. Buber wrote of guilt resulting from the harm we do to others. In either case, guilt is a miserable feeling, and one is advised to address it head on, first and foremost by uncovering its roots.

Whatever one does, one should not allow society to dictate that we feel guilty for enjoying any aspect of life, so long as no one gets hurt!
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Old 04-28-2009
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Maybe guilt is the wrong term. It is certainly conflict. I seriously enjoyed the few times I have been with shemales and usually masturbate to either those memories or pics.

But I don't think I could feel comfortable with anyone I know finding out. As I said, if I had a sexually deviant relationship with a female (I am not trying to use a wrong term here ladies, just struggling to express something), I would likely hide that too.

So I find myself wanting to go back and enjoy the pleasures of a shemale relationship again, but avoiding it over the internal conflict. It is painful. I wish there was an easy way to overcome it.
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Old 04-28-2009
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And like many here, I do not think it is a gay thing. I have no interests in men. And I am really not into anal that much. But a beautiful shemale makes me want to suck her. I never feel that about a guy.
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