Tabatha McGurr is a Brooklyn bred-writer currently residing in Bed-Stuy with her boo and dog Coco. She's been running to the Married To The Mob blog for the past six years. In her weekly column, she gives Complex readers insight into what today's young women really think about love, sex, and relationships.

Ah, anal sex! Once the excitement of oral and standard piping wears off, back-door entry becomes the last item an average dude hopes to check off his sexual to-do list. For most girls, the subject remains taboo, and chances are, you’ll have to coerce your girl into giving it a shot. If you've already awkwardly asked her about it, it may seem like she has no interest, but you're just not approaching it properly. Sometimes, women are put off because they never tried it in the right setting or with someone they felt comfortable enough with. Regardless of her reason for holding out, here are a few pointers that will help you infiltrate the elusive derriere. Be warned, they’re not for the faint of heart. Good luck fellas!

REALIZE WHAT YOU’RE ASKING OF HER

Before you go making anal demands on your woman, realize what you’re requesting. Some chicks already have a hard time handling dick the normal way, let alone taking it in the butt, and whether you’re packing tons or not much at all, it’s traumatic and unpleasant to get prodded in a new hole. If you feel that you’re at that point in your relationship where it’s time to up the sexual ante, then have a grown-up discussion about it and see if it’s something she might be into. Almost all girls will be reluctant at first, but if you’re in a happy relationship, then you should be open to trying new things together. If she’s 100% against it and gets bummed that you even asked, drop the conversation and don’t bring it up for at least another few months. When guys press the issue too much, we can’t help but wonder if there’s a little homosexuality hidden beneath the surface.

TAKE A HINT FROM THE PROS

A few summers ago I had the pleasure of working alongside Hollywood’s favorite redhead porn star, Faye Reagan, for a Married to the Mob shoot she starred in. While we prepped her with hair and makeup, questions about her line of work came up, naturally. We were most curious about her “specialty,” anal fisting. Apparently, when she started out in porn, she had an equally hard time easing into anal. Then she explained that one night while having sex with her boyfriend, she was completely relaxed by the ecstasy of a vibrator on her clit when all of the sudden, she realized that dude’s hand was up her ass. Totally not kidding. I’m not recommending fist-play for novices, she is a professional after all, but it goes to show that you should never underestimate the power of clitoral stimulation.

INTRODUCE TOYS IN THE BEDROOM

After sharing Faye’s little story, it should be obvious that your biggest aid in solving the anal equation is putting emphasis on the clitoris. Well, when you’re busy in the backyard, you won’t want to handle that task alone. Invest in some toys that will help you in the process. Go for a sleek vibrator with a few speeds that’s big enough to get work done but small enough to do its job discreetly. Lubrication is a good idea for first timers, but just because you plan on using electronics, doesn’t mean your fingers and tongue should become obsolete. Fingers are an ideal way to gain initial entry without causing too much pain, and your tongue is your greatest ally. Like the great Lil’ Kim once said: “If you ain’t lickin’ no butts, we don’t want it.”

GET HER IN THE MOOD

Now that you’ve got the idea in place and the gadgets needed to play, it’s time to set the mood. Don’t just whisper, “Hey girl, I wanna put it in your butt” or pull an Accidental Dolphin on her, since it’ll probably result in no sex at all. Instead, take her out somewhere sexy and loosen her up with a few drinks. Just be sure not to let her get too sauced or things may get messy later. I’ve heard absolute horror stories about anal amateurs who thought getting stupid off Jameson would help things along, when sadly, all it resulted in was a set of soiled sheets. Which bluntly brings me to my next point: make sure she hits the John before you get in bed. Once you’re back at the crib, all hot from the liquor, spark something up and continue the courtship. You’ve gotta play it like it’s the first time you ever fucked her. It’s only during moments of passion like those that a girl feels like giving herself to you completely.

WHAT TO EXPECT

After you make it to the bedroom, the fun of trial and error can finally begin! Anal doesn’t happen, and boom—she’s addicted. She might become a fiend eventually, but that’s after extensive efforts to see what’s most comfortable. The key is to go slow, both with entry and removal. Fast movements should only be made by experts, because though it may not seem so, the rectum is much more fragile than the vagina. That’s a little something I learned from Dr. Sue Johanson. What up girl! The vibrator will be a key factor in helping you gain entry as smoothly as possible. Without that jolt of electric relaxation, she’ll be way too tense and stiff to let you enter her easily. When you do, be attentive and listen to what your girl is telling you, because she’s ultimately gotta guide you through the motions. If it doesn’t feel good, go back to your normal routine and try again another time. That’s the beauty of happy, committed relationships—there’s always the next day.

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Sex is supposed to be a fun, no-pressure activity where the goal is for everyone to get off and have a good time. Not every girl you meet is going to be down for anal. I know total freaks that cringe at the thought of something poking around up there. The circumstances will always differ depending on who’s involved, but at least you’ll be prepared when the time comes. Now go out there and get some butt tonight!