Dominic Rosegarden is a freelance writer from Holliston, Massachusetts. He is the author of such best selling works as "The Scratch and Sniff Kama Sutra" and his self-help book, "Inner Beauty Is A Lie, You're Just Ugly".

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Right now, chances are that somewhere on your block, a young man is propositioning the classy lady that he cherishes and respects if he can do her in the butt. She more than likely will hem and haw, maybe come up with a weak excuse, maybe say no out right, maybe give it a whirl. These days, it’s almost an inevitable part of the relationship evolution. On the first date, you say, “I’d like to see you again”. After a few months, you say, “I’d like to take this to the next level”. And a couple months later, you say, “I’d like to see if I can fit my square peg in your round hole.” You know what I always say, nothing says love like Astroglide. 

There are a few funny things about this. One, there is no easy way to ask about this. You can’t just approach the girl, no matter how well you know her, and just outright say, “I’d like to have anal”. The guy always has to kind of dance around it, but it’s not the same way they might dance around another question, like “can I skip out on dinner with your folks to go to the game with the boys?” That kind of stuff is typical and usually the guy will just try to point out the benefits for the girl so she’ll suggest that he goes, like “I want to give you your space; you should spend some quality time with your family without me”.

When it comes to anal, however, the guy can’t afford to be that direct. On top of that, the mere idea of it makes him feel a subtle giddiness like a kid searching for the Christmas presents two days early:

Guy – “So, what do you want to do tonight?”

Girl – “I don’t know…did you have something in mind?”

Guy – “(tee hee) I don’t know…maybe something new.”

Girl – “Like?”

Guy – “(pfft) Maybe we should experiment a little…”

Girl – “You want to video tape it?”

Guy – “(heh heh) No…”

Girl – “You want to use a vegetable? What is it?”

Guy – “(tssss) No, not really, something else, you know, like, something else…”

Girl – “Just say it, what do you want to do?”

Guy – “(hehehehe)”

Then it comes out in some kind of awkward fashion, like “I think I should fuck you in the ass” or “I want your rectum”. Here’s where the second funny part comes in: The girl’s response. As much as the guy is walking on egg shells to get to the question, there is no way he wants the girl to just give in to it right away. Most guys like their girls to be a little freaky, but any girl that is ready to just hop on board with anal is an instant red flag.

Guy - “I think we should have anal”

Girl - “Sure! Let’s do it!”

Guy - “What? Really?”

Girl - “Yeah! Let me just stuff my face in this pillow.”

Guy - “You aren’t afraid it’s going to hurt?”

Girl - “It really isn’t that bad after you get used to it. I actually love it.”

Guy – “You’ve done it before? Wait, how often do you do this?”

Girl – “Personally, I don’t need lube, but if you want, we can use KY jelly, Vaseline, or grape jelly.”

Uggh. Someone’s not getting brought home to mother.

So the girl has to give at a little resistance. The last awkward part is the afterglow, as in, what kind of a fucking afterglow can there be? You just went in the poop chute. There might be remnants of her lunch on your rodney, and she can’t sit down for 48 hours. There is nothing romantic about that. So do you just spoon, but awkwardly stick your hips back because you don’t want to make contact with her newly sensitive butt? Do you even spoon? It’s eerily similar to the position you were just in. But then you go face to face, and the guy has a strangely satisfied smile while the girl’s face is twisted in pain, like she’s got a bad sunburn. That can’t be much more comfortable.

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It is with all this in mind that I present to you a balanced analysis of the role of anal sex in the modern relationship, weighing the pros and cons from both the perspective of the man and the woman.

 Men’s Point of View

Pros

+ Explore a brave new hole

+ IMPOSSIBLE to get pregnant – the furthest the semen will get is the lower intestines, where chances of seed implantation drop dramatically

+ High fives from all your friends

+ The ability to high five them during the actual action since the girl can’t see what’s going on

+ Ability to watch Sportscenter during sex

+ Girl can’t ask if you love her with her face stuffed in a pillow

+ No need to worry about locating the G Spot, you know it’s not there

+ Her butt will hurt too much for her to sit in your favorite chair for the next few days

+ Endless access to “walking like a cowboy” jokes

+ If drunk, possibility of subsequent blow job, also referred to as “the drumstick”

+ If she ends up being a bitch, you will ALWAYS have the comeback of “I did you in the butt”

+ Free $10 Coldstone Gift Certificate with proof of anal (not positive if they really do this, but if they don’t, they should)

+ She can’t menstruate on you from back there

+ Slap that ass until it looks like a pair of kickballs

+ The opportunity to “superman that hoe”

+ Reason to never call her again – I mean, she took anal!

Cons

- If she makes a mess of the whole thing, you might have to do laundry the next day

 Woman’s Point of View

Pros

+ At least the pillow can muffle your tears?

+ Nothing else. It’s gonna fucking hurt. I suppose if you get used to it, it could feel good, but if you get used to it, it’s probably already too late, everyone knows you’re the bitch likes it in the ass.

Cons

-         Possibility of numerous things tearing back there

-         Loss of self-respect with likely loss of respect from others

-         Don’t kid yourself, he’s not keeping this story to himself

-         You might shit all over the bed

-         Difficult to swivel head around and see if he’s turning a camcorder on or not

-         Completely kills the idea of cuddling afterwards

-         If you guys break up, he’s probably going to throw this back in your face

-         As if walking in high heels wasn’t challenge enough, now you’re going to walk like you have rickets for a few days

-         High fives from all his friends

-         Between this and the blowjobs, your digestive track has essentially become a hidden graveyard for millions and millions of sperm

-         Shitting a combination of blood, giz, and poo, with a possible leakage that could leave a trail on the ground behind you, attracting coyotes

-         Coldstone $10 Gift Certificate does not apply to receiver of the anal, only the giver

-         Read the list from his point of view; he’s probably gonna want to do it again

       -   Simply put: I want you to imagine a ring of uncooked dough, a ring small enough to fit on your finger. Now, imagine a loaf of stale French bread that’s been drying in the sun. Then I want you to imagine the loaf of French bread trying to pass through the ring of dough. How do you think that works out for the dough? You are the dough.

I’m sure some guys are sitting here thinking, “What the fuck is he doing? He’s going to ruin this for all of us.” You’re forgetting something. When do women ever listen to logic and common sense? Don’t they usually go for the wrong thing anyway? I’ve probably augmented your chances. Thank me later when you’re high fiving your buddies and reliving your romp in the rectal forest.

Until next week…stay tuggled.

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