Most Helpful Guys

  • I have a lot of experience with anal sex (with women) and have taught three women who had never tried anal to love it. Here are the things I have learned that have worked well for me.

    The first thing you need to do is get her interested in trying it. You can’t do it without her giving her consent, and the best way to approach that is by showing her how good it can feel and how intense orgasms can be with anal stimulation. Start with a well lubed finger in her ass while giving her oral, or while she rubs herself. Make sure your nails are trimmed and your skin is not rough. Clitoral stimulation is key here. Be gentle and move slowly. This will accomplish two things. First, it will get her used to the feeling of having something in her ass. It will be a different feeling for her so plan on giving her time to adjust. Second, it will allow her to associate the feelings of anal stimulation with pleasure in her brain. This is super important. Many people don’t realize that there are a ton of nerves around the anus, and the anus and anal canal are connected to the clit and vulva by the pudendal nerve complex. It can take a while for those nerves to register feelings of pleasure from anal stimulation, but once they do, they can seriously enhance a woman’s orgasms. The combination of anal and clitoral stimulation can result in super intense orgasms.

    Once she has learned how to enjoy anal orgasms, you can move on to preparing her ass for sex. There are a lot of women who have tried anal sex and hated it, and the biggest reason by far is that they tried it without adequately preparing first. The sphincter muscles, especially the outer one (at the opening), are like any other muscle in that they won't easily stretch initially to do something they are not used to doing. If the average person tried to do some of the things a gymnast can easily do, they would be in a lot of pain and may injure themselves. The same is true for anal sex. Gymnasts have taken the time to stretch and develop their muscles. You need to do the same to prepare for anal sex, and that means using toys. The best thing to start with is a butt plug that has a small tip and a smooth taper so you can gently stretch her more and more over time, and she can learn to relax her sphincters on demand.

    Dildos are good once she can comfortably take the size of a butt plug because a dildo will help her get used to the depth and in-and-out movements of sex without the pressure of feeling like she has to take a real dick long enough for her partner to orgasm. During real anal sex, once you get in, you’re not going to want to stop, and she won’t want to ask you to because she knows you’re enjoying it. There isn’t that pressure to keep going with a dildo, so she can stop any time if it’s not comfortable. It's also important for her to masturbate while using the toys so she continues to associate the feelings with pleasure. Use a good water based lube. Trust me when I say that oil and silicone lubes suck for anal.

    • Once she can comfortably take a butt plug and dildo the same size as your dick, it’s time to try the real thing. You need to know you can't just push it in and start going at it. That is a guaranteed fail. Put the head of your penis on her butthole and press gently, then back off, and repeat until she relaxes enough that you can pop the head in. The goal with each push is to help her relax a little at a time. It can take a minute or three before you can get in, especially the first few times. Alternatively, you can use her favorite butt plug to relax her first before you go in yourself. Once your head is barely inside, just relax and stay still for a minute or two to allow her to adjust. Then push in very slowly until you're all the way in. Sometimes it’s also good to do really slow and shallow strokes at first, going a little deeper with each one. Once you are all the way in, or as far as she can take you, stop again and wait a minute for her to adjust to that. Finally, start moving in and out slowly, increasing the pace a little at a time. She may not be able to take your full length at first, but she’ll relax inside and be able to take you a little deeper after a while. Just take it slow and communicate with her to make sure she is comfortable and enjoying herself. You don’t want her to have any discomfort. It’s better for both of you in the long run if she always has a positive experience because she’ll want to do it again. And again…trust me. This may seem odd to some but I recommend starting with her on her back with a pillow under her ass. That allows you to rub her clit with your thumb. It’s also incredibly hot to see the expression on her face when she cums the first time while you’re fucking her in the ass. Or, if she prefers, she can be on her knees and rubbing herself or using a small vibrator.

    • TL;DR: there are three keys to successfully teaching a woman to love and crave anal sex: 1) Teach her to enjoy the feeling of a small object (a finger) in her ass while masturbating. It’s super important that she has a lot of orgasms this way so she associates the feelings with pleasure in her brain and learns how amazing anal orgasms can feel. 2) You must take time to train her ass slowly and gently until she can relax her sphincters on demand and comfortably take the size of a hard dick. This takes time, and by time I mean weeks or months. Don’t rush this. 3) In every step of this process, you have to approach it with a long-term mindset. It takes time to do it right and the process can’t be rushed. If you rush any of it and cut corners, you risk her having a bad experience and that is definitely a bad thing for both of you. It’s worth the wait, so take your time with the knowledge that the pay off in the long run is definitely worth it.

  • Slow. Ease into it so you guys enjoy it.

    my girlfriend and I were first opposed to it, but her friend recommended it so we gave it a try. I think it took us a month to build up to penetration…. we first played with the hole, rimming , fingering , etc. also use lots of lube.. she was tight and my dick is above average. We ended up really enjoying it

    • Same for us... we are experimenting a lot of stuff and she's got a friend that really likes anal and reccomended it.

    • That’s cool man, same! The deal for her was if she tried it, I needed to try it too. So after I was able to penetrate my girlfriend , she got to use her dildo on me. It hit my prostate and gave me a mind blowing orgasm

    • That sounds so hot! I kinda want to try it too and she was interested as well. We want to try everything!

    • Show All

Scroll Down to Read Other Opinions

What's Your Opinion? Sign Up Now!

Related Questions

How come lube (sexual lube) sales fluctuate and why, any insights?
What am I supposed to do in this case? help with brother?
Have you ever been caught masturbating?
Who has more intense and longer orgasms, men or women?

What Girls & Guys Said

2 19

  • 1. If you can't get a finger in don't expect to get a dick in.
    2. Massaging the sphincter relaxes it's grip, skipping this part tightens it.
    3. Avoid water based lubes, they dry too quickly. Silicone is better.
    4. If you're straining on the toilet it's best to leave it a few days.
    5. You can open your sphincter by pushing it out like you're trying to break wind

  • Numbing cream it's really inexpensive considering and don't be stingy with it plus give it about 10 mins then apply lube again don't be stingy with it and lay a towel underneath just incase it gets messy

  • Hygiene - both

    Learn how a sphincter works.

    ignore porn

    Lube, time, pace, gentle at first

    as with all things listen to your partner and talk to them

    put a towel down and have tissues handy.

    don’t worry about dirty bits, it washes off.

    communicate to each other about what position works best for both,

    talk about how it feels

    learn to tease their arse and get it ready to play.

    It’s about patience, lube, understanding how an arse works.

  • OK, first off, you need to break her ass in slowly by using plenty of lube and inserting fingers. Start with one, preferably your pinky, and then work your way up to the thumb, and then two fingers, then three and so on. As you increase the size and number of fingers in her ass, be sure to get her used to those fingers moving in and out. Then when it’s time for her to take your penis in her ass, use lots of lube and go very slowly. Once you push the head of your penis in, you can pause and have her move her hips back to take more of it. Again, go slowly, lots of lube, and have fun with it!

  • Take it slow... use birth control every time and talk to each other.

  • Know your bodies, go slow, lots of relaxing foreplay, and always remember that too much lube is almost enough.
    The best position for beginner receivers is knees high to chest in as relaxed a position as possible. Penetrator should choose their relative position understanding the natural shape of the rectum and the shape of their “equipment”. It’s not sexy, but you need to be very knowledgeable and very careful or you could hurt yourself or someone you care about. Lastly, don’t try porno stuff until you’re both very comfortable with the fundamentals. You don’t want to end up in the hospital for trying pro moves as a rookie.

  • Use more lube than you think you need. Keep calm and relaxed, and don't be afraid to laugh at yourself.

  • A lot of lube

  • On a male or female?

    • Female

    • Have her practice with a very small anal plug or bead until she is comfortable doing it on her own before you try anything. Definitely want her to be aroused so foreplay is obvious. It can be useful to try vaginal penetration and clitoris stimulation while trying to enter her analy. If one or the other doesn't work try a combination.

  • Butt flush so no poop when doing

  • Lube, ass fingering or a butt plug, she needs to want it and be relaxed

  • use lots of grease

  • (1) BE prepared.
    (2) BE relaxed.
    (3) GO as slow as she wants: LISTEN!
    (4) Use lots of lube.
    (5) USE LUBE.
    (6) USE LOTSA LUBE!
    (7) Did I mention lube?

  • Search on Google

  • get clean, lots of lube

  • ahh just shove it in their

  • Yeah. Don’t put your dick where shit comes from.

    🤷‍♂️

  • Lick it before you stick it

  • The best advice I can give to a girl is to not do anal until you have practiced a while on your own. Anal can feel great for a girl and you can have super strong orgasms, but it will be painful the first time if you don't practice first.

  • Avoid anal?

    • Nope

    • Okay, but don't say I didn't warn you when the health problems show up.

  • Show More (1)

Latest Questions

Which one is a better aphrodisiac: Scent of Sandalwood, Freesia or Rose?
Any tips for giving oral to a man?
How does it feel to be dominated by your partner?
Have you ever had threesome?
Home >  Sexual Relationships  > Anal sex tips for beginners?