Ask GayDemon: Tight Hole BF

I've been seeing my boyfriend for 6 weeks and I still can't take his cock. He's around 8 inches and it's a really big girth too. How can I make sure I can bottom for him?

-Too Tight in Tukwila

First of all, congratulations on coming to the right advice columnist for this one. If you'd asked Miss Manners, she would have suggested polishing the silver. If you'd asked Ann Landers, you wouldn't get a response at all because she's dead. And if you'd asked Dan Savage, he would have talked about himself and his 40-something wannabe twink husband.

Now on to your asshole.

I can see you're a people pleaser. And in a big hurry to have everything just so. It's a bit demented to call this fella your boyfriend after just a few weeks together, but I'll ascribe that to your desperate need to not be alone. Plus it's just a bit immoral to have gay sex out of wedlock, considering it's legal in thirty states now with Texas close to being next. Still you seem quite anxious about the penetration thing so I'll try to help, in my own perfect way.

I don't know if he pressures you to take it all as a way to show you really care. Because if he does, that tactic isn't really a hole loosener, despite his pressure being totally justified. I mean his dick isn't going to get fucked itself. He needs you and you're failing. You've obviously taken it partway and then pushed him out, due to what I can assume is a combination of physical pain and semi-involuntary muscle contractions. Way to kill the mood!

So if you can't take a guy's cock (assuming you want to) there really is no point in calling him your boyfriend. Otherwise, what are you? Just some cute couple that clicks in every other way (sense of humor, favorite music and movies, glorious make out sessions, being there for each other emotionally, and all that jazz). All completely useless compatibilities if you can't take his cock entirely into your butt rectum.

Then once it's inside, you should be able to take him pounding you, sliding in and out for a minimum of 23 minutes, while you squeeze your sphincter for all its worth, which is exactly nothing unless you can take his cock. Or ride him to the same effect while he plays Fruit Slice on his smartphone.

Assuming he's not pressuring you, it's good for you to be pressuring yourself. Because if you don't take his cock right, he should leave you for someone who will, especially if the new guy will take it correctly that exact evening you were hoping to take his penis correctly. Like if there was a guy who lived down the hall of your apartment building and he presented his actually talented hole for complete penetration right after you had failed yet again. You should then be happy for your boyfriend to leave you for the new hole.

So to avoid all these relationship disasters and just to be a decent human being, you should immediately get a dildo that's 12"long and 8" around. Then, even if it takes hours, penetrate yourself fully. That funny breathing women who are giving birth are supposed to do can help you here. Also practice saying "I love you" to the dildo. That way you can say I love you to your boyfriend's penis later, by taking it fully. And if you can't take it fully, it means you hate him even if it doesn't feel like you do. What is more of a rejection than your tight asshole pushing him out?

I do have to warn you though. Say you do succeed in taking him inside you fully. He knows how big he is so he's just going to see you as a loose hole slut. Because anyone who can take his cock that deep must be a whore. So probably add some gasps of pain to the mix as if he's the biggest you've ever been with and you're suffering for him. It will help if your painful cries are real. And if that makes him even harder and bigger and jabs your insides even more painfully, that's how you know he's Mr. Right.

Good luck! And remember, they make Band-Aids specifically for assholes now. A pack of 50 ought to do it.

Keep me posted on what happens. Like you can send me a picture of his cock in your ass. Or just a picture of his cock. That works too. Yeah, send that. I have a feeling he'll be single soon. While you'll be cruising the "Little Dicks" section of Craigslist. For love.

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