What's the best way to do anal sex for the first time?

Question

We have baby oil, but me and my boyfriend need help to know the safe and a less painfull way.

MrOracle · Accepted Answer

My standard post on the subject, which many have found helpful:

- Get some good water-based sex lube, like Wet or AstroGlide.
- Make sure you go to the bathroom a couple of hours before, then shower and clean yourself well. You can use an enema if you are totally paranoid, but if you prepare as I mention here, that's probably overkill.
- Have him slowly work a lubricated finger into you. I said SLOWLY. Get used to having something in there, moving around and such. When YOU are ready, have him use a second finger. Go as slow as you need to in order to be comfortable. If you get to the point where he can move his fingers around a bit without any discomfort, and hopefully with a bit of pleasure, then he can try his penis.
- He needs to agree, and be absolutely clear, that if you tell him to stop, he will STOP moving immediately, and if you tell him to pull out, he will pull out immediately. YOU control the show here.
- After he's lubed up, have him SLOWLY work his way into you. It actually helps if you push out a bit, because that opens you up easier. The goal is to get him inside you and then STOP and give you a chance to adjust to something that size being in you.
- If you are still feeling okay, he can start slowly, gently thrusting. If you feel there is too much friction, have him add a little more lube, and you may need to do this a couple of times.
- If you are still okay, he can pick up the pace a bit. You direct him.

For most girls, the first time, even done right, is such a new sensation that it's hard for the girl to know what to think. If you followed my steps and went slowly, there shouldn't be much if any pain, but the sensation will still be new and different, and you might need some time to get used to it. Usually, by the second or third time, the girl starts to enjoy it (she grows used to the sensation, and isn't as stressed about it, and so can start to enjoy it), and then, she will usually ask for it from time to time when she's in the mood.

TadCurious · Accepted Answer

He should wear a condom to protect him against bacteria and to keep from spreading it around once he comes out of you. So with a latex condom you want to use a water-based lube. Use lots of lube. And then use some more lube. You need to be as relaxed as possible, and he should really try to help you have an orgasm before he even starts playing with your butt. He should wear a latex glove and massage your anus with lube and very gently start by slowly putting one finger inside you. He should let you get used to that feeling, and then try 2 fingers. Either you, or he with his other hand can stimulate your clit while he's playing with your butt. Only after your anal sphincter has opened up and is relaxed should he try penetrating you. He should go very slowly and know that if you say "Stop" he has to stop. He should only go inisde a little at a time. Once your butt has "accepted" him without pain he can begin to thrust, but still very slowly. At any point if you are in pain you should tell him. Anal can be great for both the girl and the guy but you have to do it right.

Anonymous · Accepted Answer

Listen to MrOracle, but a few tips from a woman: If it's hurting just stop where you are, don't get him to pull out - just pause and get used to it. This is so important. Pause and take a few deep breaths, let him touch and caress you as you are still, really concentrate on the sensations and feelings.

I also STRONGLY recommend that you have an orgasm or two before you start. It makes so much difference and really relaxes things down there. I find it far easier if this is the case, faaaar easier!

dazza · Accepted Answer

Use toys or fingers first, and take it slow. And you can't use too much lube. Even if you done think you need more just put more on/in. And just because he is in, you can still need more lube. And he has to listen to you and go at your pase. Also see if he will let you use a strapon on him

AustinMan · Answer

Take a look at the Take here on GAG. It's titled something like comfortable anal sex for beginners. It's a technique that's worked 100% of the time and the women have often come to crave anal.

Bob5555 · Answer

Clean yourself out with an enema beforehand or risk crapping everywhere in mid thrust. I tdefinitely happens. Honestly there are columns and info out there from  p*rn  stars who are gonna know this stuff 100x better than anyone on this site. I'd just google it and do some research if I were you.

roland77 · Answer

Rule 1: Communication and trust are the keys!
Rule2: Do all slooooow!

Pre-phase: Talk a lot with him about with honesty and open heart. Tell him what you have learned and know and listen to what he says. Good common rule: More listen, lesser talking.

Pre-shopping: Maybe go together to a sex-shop or let him buy if you feel ashamed. You should buy silicon-based instead of water-based because your rectum will remove the water from it while silicon remains longer. You also need an anal shower. It is a small rubber ball with a stick attached to it. Don't do it without protection, vaginal and oral sex is okay without condom, but anal not. So you need stronger condoms, than for vaginal/oral (really? you want to blow with a condom? See rule 1: trust is key).

Preparation: Go to toilet, get some warm water into the anal shower (it can also be used on cleaning your pussy from inside) and push it gently into your anus, let it widen, maybe use some lube on it. Then squeeze your anus together, push the shower into it (hold it, it may slip out) and spray the water in. Then let the water out through the anus as usually done and repeat up to 7-8 times while adding more water to your rectum to clean it deeper.

Widening anus: The anus is usually an exit only, means nothing goes in, but out. Normally. That is why anal sex is no regular (vaginal/oral) sex. It is very special. Start with widening your anus with smallest finger first. Your boyfriend should do that to give you some feeling of having something in your anus that is him. Sometimes, apply lube to have no itchy/"burning" sensation on your anus. If you feel you can take a thicker penis, let him insert his pointer or middle finger (now you why it is also known as "dirty finger" ... LOL). Next let him put 2 fingers in until you are comfortable with it. Then maybe 3 fingers, but that can be uncomfortable.

So anytime, you feel uncomfortable repeat it maybe a few hours later and do something completely different than talking about anal sex. Go to cinema or go for shopping, for example.

Anal sex then should be widely prepared and it should be painless as in your pussy. Note to the guys: Don't think, this is easy because on porn they do it with "ease". It is not. And there it is even painful which you don't want to give her, right?

Anonymous · Answer

Warm up with a butt plug first.

I recommend coconut oil over baby oil.

Go slooooooooow, and you might have the receptive one on top, controlling the speed. And practice with butt plugs first :) (Intercourse with the woman wearing a butt plug is a lot of fun, too, and a good way to start getting used to it)

When you're actually doing it, go v slowly, and communicate communicate communicate, and use lots and lots and LOTS of lube. (Coconut oil is solid at cool room temperature... you can push a few chunks up inside to help with lubrication :) ) And be ready to finish with hands if things aren't working out!

Other random thing, my gf has an easier time relaxing if she has a vibrator on her clit when I'm entering her.

Condoms are apparently recommended, but we've never used any. Have fun :)

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