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Anal Sex Issues

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20s gay male

I am not sure if this is the right forum for this question/issue, but here goes.

I have had several relationships over the years with guys, some serious, many not-so-serious. In all of these relationships I have been designated as "the bottom" almost by default, by every guy. I don't really have a problem with this as I do enjoy (thoroughly) being submissive. The problem is when anal sex comes into the equation.

I try to hold off on anal sex as long as possible because it's very difficult for me to enjoy. And I want so bad to enjoy it. I literally want to get fucked like the bottoms I see in porn movies but it never seems to work out that way. Anal sex with me is always awkward. If a guy does manage to get his cock inside me I can only take it for a few seconds and then I have to....well....."tap out".

I am alone in a hotel room right now after yet another failed attempt at anal sex. He has been asking to fuck me for about 2 months and I finally gave in. It's embarrassing because I was talking so much shit in text to him like "yeah I want you to fuck me so hard"....but when he gets here and puts it inside me I literally almost start crying. He said I was "too tight," which is true. And he is very well endowed so there is that as well. I was able to finish him off with a blowjob (no problems there) and he shockingly scheduled another session in the near future.

So I guess my questions are:

How can I make anal sex more enjoyable for me and my partner? How can I be "less tight"? And will I ever achieve an anal orgasm?

I want to be the well-versed slut bottom I claim to be in text messages for this dude the next time we meet. Any advice?

P.S. - I just read this entire post in "preview" and the tone is a little sarcastic but I want to be clear...I am 100% serious.

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