I am a 23 year old guy that has never been with another guy before. The exception was when I was younger, I messed around with a friend. We just put on some female clothes, rubbed on each other and then jacked off. Nothing much and afterwards there was nothing more. Since I was about 15 or so I have constantly been looking at gay porn on the net. However, my moods seem to come in spurts. Sometimes it sort of disgusts me and I can't believe I ever thought of having sex with another guy. While other times I work myself up for hours looking at gay porn and finally get myself off. Now, when I do finally get off I have the feeling of disgust come over me again. Sometimes this will wear off in a matter of minutes and I am back to thinking of men again. Other times it will last for a few days or so.
Since I was a kid I have liked to dress up in women's clothing for some reason. It just feels so much sexier than what is deemed appropriate for men to wear. Over the past few years I have really gotten into watching transexual porn and fantasize about it often. At one point I really thought that I might want a sex change.
Anyways, every so often I put up an ad looking for someone to play around with, but I always chicken out and come up with an excuse. I'll usually get extremely horny thinking about the possible encounter and then jack off imagining it. As soon as I am done I ask myself why I even thought of meeting up with another guy. Additionally, I used to go to an "arcade" back where I used to live and would watch videos while looking through the glory hole. I was too chicken to actually do it though.
This dilemma has plagued me for years and I can't seem to shake it. I have noticed that the frequency between my feelings of disgust have diminished considerably over time though. As I mentioned already, now it lasts minutes to days. Years ago it would last weeks and months. My biggest fear is that if I did go through with meeting a guy, is that I would get a little freaked out as soon as I cum. Is this feeling normal and will it go away once I finally experience something? Thanks in advance!
I think there are a few issues to address here:
Your user name indicates you consider yourself bisexual - have you had sexual relationships with women?
Did you feel disgust after you dressed up and messed around with your friend when you were younger?
Have you dressed up in female clothing and been caught by someone?
Your information gives the impression that you are turned on by the dressing up in female clothes, is that where your desire stems (only what really gets you going) or do men excite you (without the feminine appearance)?
What causes the variations in the lengths of time you feel disgust/guilt? You always feel the disgust after you've reached climax, is that correct?
Is your disgust directed mostly at yourself or towards your objects of desire or those who represent what you feel you are or want?
You say you watch gay porn, and then you say your moods "come in spurts" - does that mean your disgust comes and goes depending on the situation or that your desire for gay porn comes and goes?
Do you watch straight porn or participate in heterosexual sex without these feelings of disgust?
Here's a point of concern/interest to me: you thought you might want a sex change. Dressing up and/or enjoying transsexual porn is not indicative of gender identity disorder. I mean why did you think you would want a sex change? Are you uncomfortable with being a man? Do you identify with/as a woman vs. a man? Examine your thoughts and motivations behind that.
Yes I agree with those who say experience will quell the anxiety and doubt you're feeling. But I disagree you are at that stage. The very idea causes you to fill with self loathing and anxiety at this point - you won't get anything out of an experience except more anxiety and a hard to combat fear to try again.
I agree you should get some gay friends. Emphasis on friends. People who can support you as you come to terms with who you are - not lovers. In the meantime see if you can't seek out gay role models, explore gay history. Most importantly - this helped me actually - visualize yourself more enjoying sex with another man, enjoying intimacy with a man. Practice being okay with yourself. Do this not just in the context of masturbation. Have it as part of your day dreams and imaginings.
Finally, give yourself permission to enjoy yourself. You are a person who deserves to be happy and experience pleasure just like anyone else.
Once you are comfortable fantasizing yourself with another man, then you might be ready to actually seek out an experience. If your guilt/disgust are so great that it affects how you feel about yourself and your daily life, then I would say seek out some professional help in this matter.
P.S. - Those questions are for you to answer. You can answer them here if comfortable or answer them to yourself. Just answer them. Honestly look at yourself and you'll have a better shot of working past this
