Dear Bearded Confidant,

Great advice column first off, really informative and answers a lot of questions I have/had concerning different areas of masculine intimacy. The new question I have now, has arisen with my cum-swapping friend and I have decided to take it further and try anal sex with each other.  He's mostly a bottom and so am I, his by choice and love for the feeling of a manhood plunging into his netherhole. I, however, am a bottom mostly due to shyness and nerves. I've been told that my cock is rather thick and sometimes is a jaw-stretcher. I hate causing pain and know that a thick/long cock can really make your eyes water. He says that yes it is thick compared to other men but he's experienced (both physically and chronologically) and that he can handle it with minimal pain. So my question is (after a long novel it seems) How can I top for the first time and not feel like I'm tearing up the other man from the inside? Also, the reason why it's a major problem for me is that when I feel that I'm causing pain, I go into a fix-the-matter mindset and lose my erection and all interest on trying it again. Please help?

Dear Bottom on Top,

I have good news for you: you can shove that extra-thick cock of yours up your buddy's netherhole, cause him no pain, and keep your erection throughout.  The two key elements are how you handle foreplay and how you position your buddy upon the initial penetration (and that positioning is important for two reasons).

Here's how to get things started: lie on your back, head propped on a pillow, with lube handy.  Invite your buddy to crawl on top of you in a 69 position.  As he slathers your cock and balls, play with that beautiful ass in front of you.  Wet it with your tongue, if you wish, and very slowly work in some lube with one finger.  As your buddy's sphincter relaxes, work more and more lube deeper into the hole.  Then slowly work two fingers inside him.  If your cock is three finger-widths, then work up to probing your buddy with three fingers, re-lubing throughout.  Once he is warmed up from your fingers, he'll be ready for your cock without pain.  Meanwhile, his oral ministrations will have kept you hard and horny for serious fucking.

Now for the positioning: invite your buddy to crawl forward and sit on your cock, still facing away from you.  This position doesn't allow for eye-to-eye contact, and that's what you want for the initial penetration.  The last thing you need at this moment is to see any wincing or other reactions on your buddy's face.  It's best for him to straddle you because he can lower himself at his own rate.  In other words, he's in charge of his comfort level.  Once you're all the way in have a good rhythm going, the two of you can switch to any position or series of positions you wish.  Keep in mind that each time you change angles, your cock will initially feel a little bit different inside of him.  But your buddy will adjust quickly as his passion intensifies.

Maxi & Max by Maximo Latino
Maxi & Max (Maximo Latino)

Happy topping!  And remember—gay sex never has to be painful.