Get Stuffed! A Guide to Beginners Anal Sex

Kayden Kross and Nick Jacobs

We’ll ease your anal anxiety in no time!

Traditionally, we express our Thanksgiving gratitude by shoving mounds of turkey and pie down each other’s throats. When contemplating my last Thanksgiving, though, I recalled not the tasty meal prepared by my best friends, but the stuffing that took place following our meal. Thanksgiving of 2011 was both an eye and ass opening evening for me. It was the first night I successfully and enjoyably took a pegging, so I’d like to take this opportunity to officially redefine Thanksgiving. As a life-long fat kid I am first to enthusiastically partake in any feast, but I think it’s important to satisfy our sexual hungers as well. So this Thanksgiving, why not give thanks to your loved ones with a different kind of stuffing — in the butt!

I’d been inherently against anal sex for a long time due, unfortunately, to partners who’d gone about it the wrong way. My number one rule for any type of sex is to be 100% certain that this is an entirely consensual act. If you have to really beg and persuade your partner to do it, they’re probably going to give in half-heartedly, tainting the experience for the both of you. If your partner isn’t into it, especially a partner on the bottom, they’re not going to be as comfortable and relaxed as one needs to be during a first-time pegging. And when it comes down to it, it’s just not fair to pressure your partner into anything — ever. Instead, try talking about it when you’re not in the midst of intimacy. Express your anal interests while clothed. Do some research on how to ensure that it’s an enjoyable experience for the both of you. Don’t just beg and plead. Show your partner that you care about their experience just as much, if not more, than you’re concerned about your own.

Our chocolatey Real Feel No. 9 is a perfect post-turkey dessert!

The second most important aspect of anal sex is lube. Use it. Use a LOT of it. Seriously, you can never, ever, ever use too much lube when preparing for rear entry. Our Silicone Moist lubricant is your best bet, as silicone lube won’t dry out, maintaining slick and easy entry through the entirety of your playtime. Never combine silicone lube with a silicone toy, though. The silicone molecules can bond together and create holes in the toy, which promotes the growth and spread of bacteria, making it impossible to sterilize. So if you prefer a condom-less silicone toy, our water-based Moist lubricant will suffice, though you may find yourself re-applying more frequently.

Avoid using numbing ointments when diving into your behind. Yes, anal can hurt, but that’s usually only because you’re rushing into it! Pain is your body’s way of letting you know that something isn’t right. If you numb the area you run the risk of being completely unaware in the event that something goes wrong. You really don’t want to numb yourself in order to take a pounding because as a beginner with absolutely no anal experience, anal tearing is a distinct possibility if you rush into rough anal sex. Anal rips can heighten the risk of STIs, as well as just being generally painful as hell! Be nice to your butthole and ease into it, because if it’s your first time, you need to gradually work up to a hardcore anal pounding no matter how much you may crave it.

It’s best to experiment with smaller probes before jumping into rough penetration. Your ass hole really is elastic, but it needs a bit of guidance to reach easy elasticity. Start with a finger. Massage the opening (with lube!) to really relax yourself and the area before slowly prodding it (with more lube!), then eventually slipping the entire finger in (where’s that lube at?!). Once you’re anally acclimated to the girth of a finger, try some toys.

Heat things up on this chilly Thanksgiving night by placing our Icicles No. 2 in a warm bowl of water prior to playtime!

Patience is key in gradually stretching your anus in preparation for a nice, hard pounding. Start with our Anal Fantasy Collection Mini Silicone Plug, it’s only 1 inch in girth at its widest point, before slowly graduating to our larger AFC Silicone plugs until you reach your desired size. Once you’ve mastered the AFC anal training plugs, move on to a slightly larger toy like the Fetish Fantasy Elite 7″ Vibrating Dildo. This luxurious, super-smoooooooth silicone toy should slide in with ease (with lube, yes, more lube!) You can even stick it on the wall for hands-free penetration while tickling your tush with seven vibration patterns.

The Icicles No. 2 is also a great, gradual stretcher as its smallest bulge has a girth of only 4 centimeters. Glass toys are a ton of fun for temperature play, too. Send shivers up your rump by freezing your Icicle, or heat up those buns by placing the toy in a bowl of warm water prior to use. If you’re going to use a toy like this, though, be sure to NOT insert it very far. The safest toys to put in your butt hole will have wide, flat bases that are wider than the widest point of the toy. If it doesn’t have a base, you mustmustmust practice extreme caution.

High five! You’re no longer an anal amateur and can graduate to the real stuffing! Those with two holes should definitely check out our Real Feel Deluxe No. 8 7.5″ Double Penetrator for more wall-bangin’ satisfaction. The squishy Fanta-Flesh material mimics the softness of real skin, while remaining stiff enough to penetrate that tough heinie hole. But beware — these toys feel so real, you might just lose your appetite for the real thing!

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