FIRST TIME ANAL

Hey, I’m a guy and looking into trying anal with my girlfriend. She’s definitely interested, but neither of us want to force it and cause her any pain that can be avoided. She said she would be ready for a little pain when push comes to shove, as it might take time getting used to the sensation, but we want to minimize it if at all possible. Can you give me some tips to help start us off and maybe give me, as a guy, some tips to really help soothe her and help her out?
– Anonymous

GO. AS. SLOWLY. AS. YOU. POSSIBLY. CAN.

That’s numero uno. The first time is always the hardest and it does hurt in the beginning and she will be sore as hell afterwards, but if you do it right, it won’t hurt nearly that much and after the first time, it gets easier. I’m glad you’re asking about it because that really shows that you want to do the best you can for your girlfriend. 🙂

Here are some basic guidelines to anal. I’m going to direct the tips to girls and what they can do. You can either have your girlfriend read this or suggest these things to her.

1) RELAX. Spend a few minutes relaxing your mind and your entire body. You can also relax your anal muscles – which would help you so much! Try tightening them by squeezing your butt muscles and hold for a few minutes, then release. Do this a few times and you’ll start to feel more of what it is you need to relax.

2) LUBE, LUBE, LUBE, AND MORE FUCKING LUBE! You seriously cannot use too much lube when it comes to anal. You don’t have any natural body juices helping out here so this is extremely important. The more lube you use, the more comfortable and enjoyable it will be. Use a water-based lubricant. The skin naturally absorbs and it dries up a little more quickly than the others, but that’s why it’s the safest form to use. You don’t want to risk infection because cleaning out the ass is more difficult. So water-based lube and lots of it!!! Keep it close by in case you feel like you need more during!

3) Before going right to it, start off by using a finger to get your anal muscles to relax and open to the intrusion. Slowly insert more fingers as it becomes more comfortable for you. Rimming is also a good idea (tongue fucking your ass). The anus has a concentration of nerve endings and can be an erogenous zone for some women. So the more gentle finger play and stimulation you have there, the better intercourse will feel.

4) Communicate! Talk to your partner about your fears or desires for anal sex. Continue to communicate when first trying anal sex by letting your partner know if it hurts or if you would like him to move more slowly or more quickly. It is important that you feel comfortable so don’t be afraid to talk to them about it! Just biting your pillow is NOT going to help you here. If you’re willing to try this in the first place, then you need to be in a position where you feel comfortable directing your partner in exactly what you need. Never force anything. This is all about easing into it at the pace that YOU need.

5) Women—you stay in control! Especially the first time you are trying anal penetration, it is good to be in control of your man’s dick so that you can guide it at a pace and pressure that you are comfortable with. Take your time in getting it in. This is also good because the lining of the anus is very sensitive, so pay attention to your body and stop if it is too painful. Some good beginning positions for when trying anal sex are missionary, doggie style, and laying on your side with your partner behind you on his side. These positions are the best because your anal muscles relax more easily in them. Men, you need to be on your toes and listen to your partner. Follow their cues without question. If you don’t listen, you risk hurting them and causing real damage to their body. So be extra aware of everything that you’re doing!

6) It WILL be uncomfortable at first, though the pain should not be overwhelming. If it is, stop, and keep using foreplay until you’re ready to try again. Real pain, pinching, intense discomfort, are all signs that you haven’t fully prepared your anus for penetration so you need to keep working on it. Don’t hold your breath when you feel the discomfort – breathe through it. Men, you can help to remind your partners by gently encouraging her to breathe. Whisper it in her ear, be reassuring, touch her, talk to her – just stay in constant communication so she doesn’t feel like she’s in this place of discomfort alone and you’re just there to fuck her ass.

7) Be safe! Shower before and after, taking extra care to clean down there. Do not go from ass to pussy, it can lead to infection or complications. Always use a condom! (That’s not even just about safety, it’s provides extra lubrication and it’s easier to slide in and out…) If you try anal and want to switch to pussy again, discard that condom and put on a new one to minimize the risk of infection.

8) Stimulating both your ass and your pussy will maximize your pleasure. Either have him finger your pussy or maybe even bring a vibrator in and use that while he’s playing with your ass. It feels great for BOTH partners! It’s important not to forget your clit and your pussy in general just because you’re focusing on anal sex. It all works together! Most women can’t climax just from anal so that’s why you need both.

9) For those receiving, it’s ideal to make sure you use the bathroom to empty all contents before starting. It’s rare, but it happens, so try to avoid any messy situation with a quick trip to the bathroom.

Okay, so some particular advice for guys…

Don’t do what you’ve seen in porn. NEVER. I beg of you. Porn is the worst model you can use for sex. In most porn, you see a guy just ram it home in one shot. NEVER DO THIS. It will not only hurt your partner, but it’s also a mood killer and major turn off. You need to gently ease into her. If she tells you it’s too much, either stop where you are or pull out completely (depending on what she’s asking).

– When it comes to anal, you’ll be pushing in a little, then stopping, pulling out, try some fingering again, then go back and ease in a little more. It can be frustrating for you, I know, but you will hurt your partner if you do anything overzealous in the beginning. You can cause tearing and bleeding and your partner will NOT want to try it ever again. So patience is your best friend. Think of this as fun, not as some frustrating thing where you can’t just get into her already! Play around with it, enjoy the new sensations, listen to your partner, and you’ll be making both of your experiences very enjoyable!

– The best way for women to enjoy anal is to orgasm at least once before trying it. So try getting her off with oral sex (you can also start slipping your digits up the other way to begin preparing her – massage her anus first and then gently insert a finger). Women also prefer having regular intercourse before switching to anal. So have sex, make sure she orgasms, and then for the next round, that’s the best time to try anal. She’ll be aroused, ready, and relaxed – which is key! Jumping straight to anal without anything else is a bad idea and you’ll likely be rejected.

– I can’t stress this enough, listen to your partner. Do what they ask you to do. If you get too eager and go too fast before they’re ready, you’ll hurt them and the chances of them wanting to try anal sex again are slim to none. So do what you have to do to mentally prepare yourself to be patient and understanding. If your partner doesn’t enjoy it after the first time, then you need to respect that. Anal sex isn’t for everyone. Some people love it, others do not. Never pressure your partner into doing it again if they don’t want to or make them feel guilty for not wanting it. Respect their wishes. There are many…many…many different ways to explore and have fun with sex that doesn’t involve anal. So don’t be so disappointed! You’ve got plenty more to try!

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