Ask Carly #11 “Face down, Ass up, that’s the way we like to fuck”

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By Carly Pentewyn

Welcome to the eleventh edition of the ‘Ask Carly’ column here at The Observer.

Shortly after the last edition was published, I received following letter:


Dear Carly,

Thank you for all the advice given in your former columns, they really morphed my sex life into something far spicier.

I’ll start this off by saying, my fiance is an ass lover. He is OBSESSED with my ass, and he even brings home dinner form Gein Burger every other night in hopes it will grow bigger over time. Don’t get me wrong, I like their fries and shakes, but it’s getting a little old, and I am also not sure about the mystery meat. Prior to having sex, he takes out the measurement tape to check on the progress, and says “soon”, but nothing ever happens.

For the love of god, I’m vegan, and I can’t take it anymore, I just want him to pop my anal cherry and be done with it, so I don’t have to eat any more fast food for a while. I’ve also never tried anal before, so I was hoping you could save my diet, by explaining how to spring my ass on him as fast as possible.

With love, Miss Clee Torres


Dear Miss Clee Torres,

Thank you for following my advice column, and I am glad it is transforming your bedside manners into something better. Helping people is why I am doing this.

Your fiancé sounds like a real charmer, and since you haven’t dumped him yet, I guess there’s more to him than meets the eye. For most girls, having anal sex for the first time, can be a big decision, although for me it happened on the pool table at Lou’s after about 6 drafts.

If he is such a big ass man as you claim, I doubt he will need much persuasion to get it on, and it seems the far easiest way is to get on top of him in a hotsquatting cowgirl position kniown as the ‘See-Saw’, and ask him if he would like to see his dick in your butt. This is one of my signature movies, as he will be able to watch every inch get swallowed by your black hole in real time. If he doesn’t stop bringing home burgers after that, you should make him your ex-fiance as fast as possible, or you will lose the right to any plausible compliments when trying on jeans at the store.

With love, Carly


Christmas Bonus – Carly’s Favourite Anal Positions

Since this is 2023’s last edition of the “Ask Carly Column”, I will offer some insights into my favourite anal positions, so you can get on Santa’s naughty list. Also, don’t worry if you don’t have any lube for these positions, as a gram of coke up the rear will do the trick just as well. (Do not try that advice at home – Ed)

  1. The See-Saw: (as mentioned above)

In addition to the information already explained, this also works welt with a dildo for some DP action, all while the ability of eye contact exists. (That is if you don’t have the average genitalia of a Spanky’s employee).

  1. Reverse Cowgirl:

Reverse Cowgirl (or Cowboy!) is a pretty well-known sex position for a reason – it’s simple and great for anal sex. To perform, the giving partner needs to lie down on their back, after which the receiver can lower themselves down, facing away from them.

  1. Face down, Ass up:

“Face Down, Ass up” (That’s the way we like to fuck) is not just a song by ‘2 Live Crew’ but also my all time favorite position for both number one and number two action. If you know this, you wont ever really need another position, and it can even be spiced up with cuffs and a ballgag for additional “fun”. My love for this position is also shared by my new husband.

  1. Leapfrog;

“They were only playing Leapfrog” As Yoda sang in pornhub version of “The Phantom Menace”. A variation of the doggy style. With the Leapfrog position, they actually need to squat with their knees bent and their upper body leaning forwards, hands down flat on the bed or floor in front of them. If you are training for porn, this is a great position to both build your pain tolerance and your fitness.

  1. The Bulldog

The Bulldog position is perfect for when the giver really wants to dominate and give the receiver a vigorous pounding! It’s a similar anal position to doggy style, with the receiver down on their hands and knees.

And that was todays edition of the Ask Carly Column. If you have a dilemma preventing you from living your life to the fullest extent, don’t hesitate to write me at [email protected] (( IM Carly Cox (Calanthral Falodir) ))

Until next time!

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