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Attractive or has the biggest dick (the porn ideal) does not mean they can fuck well.
I hate all the 'caught in public' fake shit which seems to creep in on most sites...
Bottoming is all about angles and patients, if you aren't going SUPER slow and hitting your prostate it may be a bad experience.
Also, if you've never had anything in your anus before, it is advisable to try it alone and get that experience under your belt.
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Lately I've been watching a lot of gay and transsexual porn and masturbation isn't enough any more.
In my experience, having a dildo rubbing against the prostate while you jack off is a great way to let your brain associate anal play with pleasure.
When you find the sweet spot you will know you have found it.
Depending on your approach, taking it up the ass can be either really uncomfortable and leave you feeling weird or it can be the most amazing experience the male body is capable of having.