Wednesday’s Ask Heather: The Getting Ass Edition

So today’s Ask Heather is not for your mother to read. Unless your mom likes a little ass play. In that case, she can keep reading.

Here’s an email I woke up to yesterday, confirming the fact that it’s time to get dirty.

Heather,
What music to play to get it on and why are chicks always late — are these really the best topics you have for ask heather? The last one started out well, sucking balls, I thought it was going to be an expose about the fact that women should not actually suck balls, but rather tongue them, cuz they’re sensitive, but no. Disappointing. How about this — when, if ever, is it acceptable for a guy to go for some butt play with his girl? How best to start, discuss first or no, what’s the best reason to cite for wanting said butt play, etc. This took all of 3 seconds for me to think of, you need to step it up…
Signed, JP, Washington, DC

And so today I will answer the age-old question, How to Get a Girl to Take it up the Ass, with a little WHOWHATWHENWHEREWHY session.

But first, guys, jesus CHRIST. What is with the fucking ass play? Obviously this has more to do with wanting what you can’t have than actually enjoying shoving your dick up our asses. Because I can’t really imagine that the actual sex is 8 trillion times better. Unless it is, and then fine, you can freak the f out all you want and go on dying to do us up the ass like it’s the sexual equivalent of winning the Nobel Peace Prize.

Here we go.

WHAT: We already know the what. You want to shove something hard and large (hopefully for you but in this case not for us) up our balloon knots and you are driven mad by the fact that you are not allowed to. Fine. That’s the issue at hand.

WHO: You making ridiculous demands when being given a blow job or a session other than missionary should be suitable but you have to get all selfish and idealistic about things and start demanding whoever you’re with “be open” with you. And as for the girl, the who part goes something like this. WHO would let you shove your dick there? Three options. One, someone that’s madly in love with you. Really, stupidly, would do anything for you in love with you. Two, a whore. Whores have no problem taking it up the ass because they are easy and I assume use their ass as a canvas more than the rest of us and so they don’t mind giving it up. And then lastly, girls that want to impress you for who knows what fucking reason. Primarily because they have insecurity issues and feel like offering you their ass will win your heart. Which it will, for one second, but then you’ll go tell all your friends about how you screwed some skank up the ass and then her poor, stupid, naive heart will be broken, as will her O ring, but that’s her own fucking fault for resorting to the big game to win your heart. Duh.

So now we know what kind of girl is pumped to give you her ass. But that’s not what this question is really about, is it? You want to know how to get your vanilla sex loving woman, who you have been banging for so long that it bores you to tears and forces you to wank in the shower and you’re just dying to get her to do something new. So. How do you turn your woman into a bent over dream? Well, let’s carry on.

WHEN: Well, normally I’d say that unless it’s Christmas or your fucking birthday or you got a promotion or you won the lottery and she gets half, you shouldn’t be asking unless you know she’s into it because she’s just going to be pissed at you for being greedy. That being said, if you can get her to consider the idea, you should know that wining and dining her are a good idea but think logically. Spirits and wine make girls aggressive, bubbly, warm inside and often more aggressive and ambitious than normal. Beer is going to make her bloated and want to shit later and it’s not great for getting in her ass. As for dinner, you should not be dining anywhere disastrous like a Chinese restaurant, Mexican is obviously out and if you’re cheap, skip Popeyes, KFC, Mc Ds or anything else you can drive through a window booth to get. You don’t want to promote bathroom emergencies. In fact, come to think of it, if I were to do this ass game, I’d want some notice so I could stop eating for two days.

Where: The only place that’s suitable for ass sex is the bed. We’re not going to sit on you backwards in a car or let you bend us over in the kitchen or anything cheeky like that. Maybe you’ll get this in the shower but water has never really been a great lube and so I’d just say stick to the bed where you can get out some toys and maybe a towel because who knows what could happen. And comfort is key.

Why: Because you all want ass sex. All of you.

So how do you accomplish this task?

First, you need to tell her, preferably in the middle of some hot and heavy, great, mind-blowing other sex, Honey, I want to do everything with you. Give you everything (this will seem sweet and she certainly won’t know what the fuck you’re getting at) She’ll be all, me too. At this point, you have to see where she’s at mentally. This is where I’d suggest you toss a finger in her ass while doing her. OR BETTER YET, while you’re going down on her. Perfect. This works brilliantly, unless you’re bad at that and then you’re just fucked. I like to refer to this as the finger recce.

So you’re face deep and you reach around and insert said finger and work your magic. If she tenses up, bites you in a non-sexy way, pushes you off her, hits you and screams WHATTHEFUCKISWRONGWITHYOU? I’m guessing she can’t be turned. If she goes wild and loves it, you’re going to probably get to choose your own adventure on this one. If she’s somewhere in between, you have a bit of work to do. Keep at it and break her in slow. Our asses are not used to stuff going in them and even fingers can be awkward and kind of painful at first.

So you get that far. Now it’s your job to continue to break her in slowly and make sure she’s having a good time with it or you are not putting yourself anywhere. This is where you introduce lube and possibly anal beads into the equation. And by lube I don’t mean lick your finger or spit on your dick for fucks sake. I mean get some KY out. Nothing kept in a kitchen pantry should be used, either, and I have no idea why I felt the need to clarify on that one.

Now I should note that probably 75% of girls are freaked out by anal beads. They look scary, they’re hard and we all just have visions of you pulling them out covered in shit, which makes us feel sick and awful in the stomach and that’s a nightmare to us even when you totally lie and say, I really WILL NOT CARE if that happens. Really, you won’t? You’d be thrilled to pull out a string of my shit and we’d just what? Carry on like nothing just happened? Yeah right.

I almost forgot vibrators. Vibrators are very essential in this process. YOu’ll be too busy behind us being pumped that you’re getting in that you’re focusing like a maniac so you don’t blow it the minute you get in and we’ll be too busy biting our lip and praying to god nothing rips or there’s no bleeding and we’ll be deep breathing and thinking of the best sex we’ve ever had to ensure we’re as fired up about this as possible and I think everyone involved will be too busy mentally to focus on diddling the bean while you’re ass fucking. So grab a vibrator and put it on her clit because that will help with the nerves and keep her in the mood for somewhat painful sex and being outrageously horny will make the ass sex a good, I kind of like the pain, experience and not some unlubed personal violation that mentally scars you for life.

Now your size. This will be a factor. Typically, we are obviously pumped if you are hung like a baby’s arm (like a two-year olds). But in this case, we would prefer a penis of the smaller variety. Smaller penises are going to be less scary to begin with and will give us less anxiety going in. Also, NOTE TO SELF. In this type of sex only is it acceptable and somewhere preferred to go in half cocked. Not limp, but halfway there works. That way you can kind of squish it in and then we can feel it grow gradually, kind of like when a sponge gets wet. This reduces any sort of painful push your way through issue that’s bound to happen when you’re trying and we’re ass tightening and you keep trying and we’re like, no no no, and you pretend it’s one of those good no situations but seriously we’re like, OHMYGOD I take it back, get your dick away from me and then you push one more time like my ass is going to unpucker and when we scream WHATTHEFUCKISWRONGWITHYOU and you’re like, oops, sorry, I didn’t mean to.

OOPS, SORRY, I DIDN’T MEAN TO? In what situation does that type of denial ever work? And we know you meant to. I’ve never just happened to slip and land jage first on your lips and you didn’t accidentally just try to jam however many inches of hot cock up my ass because that’s where it landed, so let’s not be all cute about it.

Ok, so we’ve covered that you need booze to loosen her up, but not to blackout status because that’s just not fair or fun. Then you need to sweet talk, start slow with some lesser ass play, bring in the lube and sex toys, go in not so hard, yadda yadda.

But now you’re in. So now what?

Just go for it. Slowly. And not like a fucking jackhammer. Not like you’re fucking jabbing at something and have some rhythm so she can get as into it as she wants and there’s some chance of it being enjoyable. And while you’re doing this, you better be fucking moaning our name because I want to HEAR the enjoyment and the deep breathing. Also, a nice, firm, hands on each side of the ass, pulling us back and forth would be nice. That’s taking control of the situation and it’s nice. Also, keep with the vibrating toy. This will help her get into it more. If you feel her rocking back, like she’s interested in what’s going on and is kind of fucking you back, consider this method a winner. If she makes any noises that seem pleasurable, lucky you. You are a lucky man and she is a champ.

And to end? You have two choices. Blow it in her and risk her being pissed that her ass will leak for a few days. Or pull out and shoot it on her back. And if you do the shooting method, don’t even fucking complain that you had to pull out and do that because you were just in her ass so I don’t want to hear it.

The clean-up. If there is ANY sort of mess, there should be no mention of such, no gagging, no throwing up and especially no, OHMYGODTHATISDISGUSTING. You need to pull out and walk yourself straight to the bathroom, wash your dick and wash your hands. Toss her a towel, give her a kiss and leave the room and go get some juice for her or a snack. Not only is this thoughtful in general, but it also gives her the chance to stand up alone and redress. Standing up is a bit of a nightmare because who knows what noise or leakage could occur, wiping probably needs to be involved, we are probably going to want a shower and no matter how long you’ve been together, this particular clean-up, especially the first time, is best alone until you feel like you’ve mastered what you’re ass is going to do as a reaction.

So that, boys, is my advice on how to win the prize. Good luck and may the force be with you.