My (24m) GF (22f) is interested in trying anal, we’ve done our research and followed guides online, even purchased a few toys, however I’m still a little apprehensive about it. I have a couple of concerns, firstly being cleanliness and secondly about pain. The first is fairly self explanatory, but I am mostly concerned with the second. I’ve heard anal can be quite painful and I’m worried that with my size (8.5x6inches) I’ll cause more pain than pleasure. Should we just stick to toys or should we go further and if so is there any sort of preparation necessary for larger sizes?

11 comments

  1. My partner and I are currently trying anal too. We have done it only one time for now. I have licked her anus before, for lubrification, and then, I put just the top of the penis for start. We take like 10 minutes in that way before going more deeply. We haven’t put all the penis inside and it was a little painful at the start, a strange sensation she said, but it was exciting at the same time. So my advice is to take a lot of time before putting all the penis inside, go progressively, with time. Communicate at every moment about what she feels, don’t forget the lubrification part, it’s very important too

  2. Yeah. I have slightly more girth. It probably won’t be the most comfortable for her and don’t plan on being able to go very deep. Pay LOTS of attention to her body language, and you will know when it is time to stop. Don’t make her ask you to.

    Use TONS of lube.

    And if you are really lucky, you might be able to get to play “just the tip” every year for your birthday.

  5. Jumping right into anal sex is going way to fast and is a recipe for too-much-too-soon. Try a butt plug in her ass during foreplay, then keep it in during vaginal sex. She has to first get comfortable with the sensation and relaxing her muscles.

    As far as cleanliness… it is what it is. You can experiment first in the shower and clean as you go, but you can expect some smell and dirt sometimes if you are doing anal.

  6. Yeah, you train for bigger sizes. Start slowly with toys and only move up once she’s fully comfortable. It will take time but that’s part of the fun imo. Also, always use more lube than you think you need lol.

  7. Wife and I do anal all the time. We’re both clean so it’s not an issue. When I first started having anal sex with my current partner, her ass was super tight and even though I’m average sized, it took a lot of lube and a few sessions to fully penetrate her. She doesn’t feel pain more so a pressure as I get harder and closer to cumming. She does have dildos which she used to practice with

  8. Personally, I would spend weeks (maybe a month or two) working up to where your girlfriend is begging for PiA.

    Start with your pinky, then your middle finger, then two fingers, and (based on your size) maybe even three fingers. Once you are comfortably there and she is fully into it, only then would I even consider full on PiA.

    Good PiA take foreplay just like good PiV.

    Lick her ass, massage her asshole with the pad of your finger or thumb. When it is ready, it will sort of suck your finger in with very little pushing. And, it will keep swallowing your finger deeper and deeper.

    You can try butt plugs. But, personally, I find them less than useful. The whole point of anal is fit your penis in there. A butt plug once in has a very thin stem. You need something that is going to train and stretch the anus to accept your penis. A series of small to larger dildos would be much more effective than a butt plug, in my experience.

    Obviously, a ton of good lube. Water based is fine (we prefer thicker gel water based lube). Silicone is great if you don’t mind the clean up.

    When you are finally read for PiA, slowly insert just the head of your penis. Again, just like your finger, it should get sucked in. Slowly, and I mean extremely slowly, slide further in. Allowing her to dictate the speed. I would suggest you slide in, stay perfectly still, and let her rub her clit to orgasm. Do this a couple sessions. Then build up to actual slowly fucking her with an in and out motion.

    As far as position, forget doggy style. Seriously. Being on all fours naturally tightens all those muscles back there. Do modified missionary. She lays on her back with her butt at the edge of the bed. You are standing on the floor. If needed, put a pillow under her ass. Have her slightly pull her legs/knees back. This naturally relaxes all the muscles back there. This position gives you excellent communication skills to talk and see her face. You both have complete full use of your hands to communicate, play with her clit or breasts or body, she can also use her hands on your thighs or stomach to dictate speed and/or depth.

    As far as cleanliness, a lot of people are just clean by nature. My wife can have a bowl movement a couple hours before sex and she is completely clean. She has never had to do an enema or anything like that. And, we have never once had an accident. If this is something that you guys get really into, a fiber supplement can really help keep things clean and healthy down there. Diet goes a long way. Don’t eat watery or greasy items like a salad or big burger or streak before hand. Again, go for fiber or carbs.

    You should be doing lots of foreplay with your fingers anyway. So, you put a finger in, oops you feel something. No big deal. Not tonight honey. Nothing to be embarrassed about or freak. Just is what it is.

    If you cum in her ass, be warned, it will leak out for hours. If my wife wants that, it is typically on a night that we plan to say in. Or, I just pull out and cum on her belly or ass as normal.

    Anal had given my wife some of her most power orgasms she has ever had.

    It should never be painful. Sure, maybe a slight discomfort for a 1/2 second as you adjust. Or maybe you got the angle slightly wrong. Nothing different than vaginal sex.

    It is something that we work into rotation once or twice a month. Although some form of anal play (tongue, fingers, toys) happens almost every encounter.

    YMMV, good luck, have fun, and just communicate!

  9. Fuck her with the toy until the tooter hole gets all opened up and relaxed. Lube up the dong and fuck that ass

  10. Use (training) plugs of increasing size, with plenty of lube, until she can take one just about your girth without pain. Some sessions might only involve the plugs, and you can bring her to orgasm with it in.

    Eventually, and probably quickly, she’ll be prepared to take you. But take your time and let her be in control of the progress.

    Regarding cleanliness: sometimes there will be poo. No big deal. And definitely don’t go back to front. Nothing that’s been in her ass should go in her pussy without a thorough cleaning first.

  11. There are two easy solutions to your problem.

    1) While you are still getting used to the idea of anal, wear a condom – that way you will not get anything yucky on your cock. Truth is that as you get more comfortable, your learn to ignore the “uncleanliness” angle. She learns to clean herself well before you have anal sex and you learn to clean yourself after having anal sex.

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    2) Lube lube lube. Use lot of lube and then add more. Start by using your lubed fingers slowly so that she gets used to relaxing. Once you have used a finger or two or three, then leverage the toys you have purchased. Always remember to lube everything well and take things slowly. Once you have used larger toys then she will become ready for taking you. Again use lot of lube and then add more. Push very slowly and don’t attempt to go all the way the first time around. Gradually each time go further and have her ass recover inbetween. Always make sure she is well relaxed and never hurry things.

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    Hope that helps!

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