Just the Tips

Anal Play Tips for a First Hookup

Woman on Top of Man during Foreplay

If you love anal sex, you probably already know that it’s a rare experience on a first hookup. It’s just something that takes a certain level of trust and comfortability to happen. Even women who love opening up the back doors are going to want to get to know you first. But, that doesn’t mean various kinds of anal play are out of the question.

Anal play between the right partners can be very exciting, a little taboo, a little raunchy, and an extremely exciting type of foreplay. So let’s look at some types of anal play that might just happen with the right kind of lover, and how you can be ready to broach the subject.

Tips for Anal Play on a First Hookup

Reread Her Profile

I know that a lot of men skim women’s profiles, and sometimes don’t even read them before sending a first-contact message. When you do this, you’re missing out on a lot of valuable information. And sometimes that info contains sexual preferences, boundaries, and kinks. So go back to find out if anal play is welcome, a hard no, or an unmentioned possibility.

Know Your Boundaries and Respect Hers

What kind of anal play are you into? Do you want to put your finger inside her, or do you want her finger in you? Is it more about rimming, a little tongue action? Would you use a dental dam? Are erotic enemas something you would like to try later on? Know what you like and want, and find out her anal play dos and don’ts.

Be Prepared for the Play

This isn’t going to be something you bring up over dinner or drinks at the bar: “Hey, do you mind if I rim you later on, back at your place?” No. It needs to happen organically. But what you can do is be prepared, so if it does you have any necessary accoutrements on hand. Lube is a must for many fun kinks or types of anal play, so keep some handy. The other recommendation is clean towels for showering or washing up… inside a clean bathroom.

Take Your Time Getting There

If everything anal is a fetish, you know it’s going to be on your mind. But if that’s your only thought, it may prevent you from being the best lover you can be. A first hookup is the time to make a great impression, so that it won’t be your last hookup (unless you just love one-offs). Think of it this way: a woman is not going to let you get near her starfish, unless she’s aroused to the max, so the initial effort in to take her to that place.

Let It Unfold Naturally

When you’re both naked and in the make-out stage of a great hookup, that’s when anal exploration usually happens. If your hand gets too close for comfort for her, she’s going to let you know. If you want to ask permission or if she’s interested, that’s always a great idea. If she’s into you but not into that, it’s not going to ruin the vibe to bring it up. If it’s a no-go zone, there’s plenty else to enjoy.

Wait Until Next Time

If your anal play desires do not manifest in a natural way, don’t lose hope or push it. Enjoy whatever this hookup entails—making out or oral or something else—and save it for another time. Like I said, anal anything is almost too much to hope for on a first hookup, so don’t be surprised or disappointed if it’s not on the menu your first night together. Getting to know someone more usually means you’ll get to know their body more too!

And on a practical note: Most women like to keep their bush and back entrance trim and tidy for visitors, so she may want notice of your desires beforehand so that she has the time to prepare.

What are you top tips for anal play on a first hookup?

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