Ask A Dick: Popping The Cherry

First times are almost always awkward and not that good. First dates, first fucks, or first anythings really. There is all that buildup to the event itself that it will never live up to the expectation that movies, books, and society have set. It’s all bullshit really though. Smoke and mirrors. Don’t resent them for it because after all you are doing it too. The problem is that if you are going to come with the real you. It’s got to be the whole thing. If you are a filthy mouthed jackass, or a dirty whore (this isn’t an insult ladies) then you have to be 100% clear on that shit, which is tough. You will turn lots of people away, but maybe it’s better for everyone involved? Who knows? Like I said last time, I am full of shit.

(No Longer) Sleeping With The Enemy

“So, I dated this guy for a while, and hung out with him. He even met my family and friends. I later found out that he has been living with his girlfriend for seven years! He lied to me about where he lived and several other things. What is the best way to seek revenge on him? Ahhhhh!”

~A Dish Best Served Cold

Revenge is always something that works out better in your head than in reality. You can tell his girlfriend, but he will just flip it back onto you. There is even a good chance that she already knows he is a piece of shit, but just wont leave him. Love and all the romantic movie shit, right? Really the best revenge is to move on and find a real winner, which is what you want anyway. Not some pseudo-player that can’t even bring up the idea of an open relationship to his girlfriend. Flaunt that shit in front of him. Even us real dirt bags feel a little twang at the heart strings when we see someone from the past with another guy. Especially, one that is better than us.

Ticket To Ride

“What is the appropriate response to having a one night stand and then the individual have a panic attack mid-requested-fisting? I didn’t want to just yank my hand out, but at the same time it seems strange to be trapped there and all concerned at the same time when you barely know the person…”

~Friendly Inside Some Times

You know that saying, “Look before you leap”? I am going to start a new one that goes something like this, “Know who you are shoving your fucking hand in before you do.” What do you think? I mean, I am not one to advise anyone to turn down bedroom requests. We have all been caught in the, “one more finger” scenario. Yes, ladies we know what you are doing there. Anyway, yes, yanking your hand out of a pussy would be a bad idea. She is the one having a panic attack. That doesn’t mean you need to have one too. It’s like a fire drill. Quickly and calmly move to the nearest exit. If you buy the fisting ticket be prepared to take the five finger ride. This is the risk you are taking.

An Anal Request

“I have been in a relationship my girlfriend for 8 months. We have always had a great sex life, but I have always wanted to have anal sex with her. Is there any good way to bring it up to her?”

~Backdoor Buddy

This question is really about getting what you want when you fuck someone. It is really such a simple answer. If you want to bring the asshole into the bedroom routine start bringing it in. Simple enough, right? If you are eating her out start going lower and lower on her. That’s right Buddy, you might have to toss a salad if you want to stick your dick there later. It isn’t an immediate thing, but by doing that you have brought the asshole into the game. Then work up to a finger, and before you know it you are shoving your dick in there. I’d recommend you let her go to town on your butt too. If it’s good for the goose and all that shit. Now, if at some point along this line of work you are putting in she expresses a desire to go no further you have to respect that. Hopefully, this isn’t a make or break kind of thing for you because at the end of the day a pussy feels better anyway.

Have a question? Email me at askadick@purgeatl.com