How to Have Anal Sex with a Big Penis

Can a penis be too big for anal sex? Probably not, though size does matter. However, a big penis doesn’t have to be a deal breaker. With proper preparation, enough lubrication, the right position, and relaxation techniques, having anal sex with a big penis can be comfortable and pleasurable.

1) Preparation. One way to prepare yourself for anal sex with a big penis is butt plugs. Get one butt plug as large as the diameter of your partner’s penis and one or two smaller ones. Use the smaller ones as “trainers,” if necessary,  and work up to being able to insert the largest one. You can wear a butt plug during the day to prepare for anal sex that evening, or wait to insert it prior to foreplay. If you wear it while having vaginal sex, he will love how tight it makes your vagina feel. Once you’re able to insert and wear the large butt plug, penetration with his penis should then be fairly comfortable.

2) Lubrication. Since the anal region is not self-lubricating, lubricants are essential to reduce friction and discomfort during anal sex, and even more so with a big penis. A good choice for anal sex is Astroglide, a super-smooth, long-lasting lubricant that can be found at many neighborhood pharmacies. Use as much lube as possible. You really can’t use too much.

3) Position. Though doggy-style may be the most popular anal sex position, it’s not necessarily the best one if your partner has a big penis. Missionary position (man on top, woman on bottom) allows the woman to fully relax her anus, making penetration much easier. Another good position is side anal or “spooning.” The woman lies on one side, and the man approaches from the rear. The woman can relax her anus, and the man can easily access the entire anal area.

4) Relaxation. If you have pain when his penis is inserted, have your partner stop, but not pull out. He should just hold his position while you take several slow, deep breaths and relax the anal muscles. Pushing out (as you would for a bowel movement) will help to open those muscles and allow them relax against the penis. The pain should subside though you may still might feel some discomfort from having something pushing into you and being stretched open. Try to stay relaxed as he continues to push his penis in further. Any time it hurts, have your partner stop while you take slow, deep breaths, push out, and relax until the pain subsides.

If the man exercises patience and control, most women will be able to accommodate any size penis using the above techniques. The incredible sensations of fullness for a woman and tightness for the man make anal sex with a big penis worth the extra time and effort.

My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here

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58 Responses

  1. I dont think its necesary so much training or so much thinking before to have anal sex. When u take care for all the details I dont thin un can feel the pleasure. U can do it with every penis – it doesnt matter the shape size or colour. Important is to trust your partner and to wish yourself that in this moment u want him in your ass. Belive me, it works without training or oil. And its more fun when u feel just orgasm after orgasm without thinking…
    Take care!

  2. .I don’t think so much training is usually necessary either. Following the 10 Steps to Great First Time Anal Sex should be enough for most couples. However, I’ve had reader requests to do a post about this topic after my post What to Do If Your Man’s Penis Is Too Big, which only covered vaginal sex.

  3. wow. how helpful!
    :)

  4. anal sex is forbiden, it could be danger for the healhty, beside it wasn’t normal behavior for human being.
    the poin is ” People never being satisfied” that’s why they always try another thing and keep trying to get the up-date one.
    Ass hole does not match to Penis,it’s dirt place because…it’s like an EXHAUST……………ha ha ha ha
    Next time you write a welknown brand of exhaust there, like “Yoshimura or Arrow etc” it will be much better look, ha ha ha ha.
    Da da da da, bye bye bye

  5. Good tips! Thanks!

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  32. How can I prepare my ass for anal sex

  33. Follow the recommendations in this article.

  34. thank god i’m queer. to think that women need to do all of these “exercises” in order to participate in an activity (sex) that should be NATURAL and PLEASURABLE makes me wanna puke. women, unlike men, do not have a prostate and therefore anal sex for women CANNOT make them come. in essence, this article is about how women should please men at their own expense (“it will make the vagina more tight and more pleasurable for HIM!”). now, many het women believe that their utmost pleasure is pleasing men sexually (i.e. “i get off by him getting off!”) but give me a break; that is a meta-pleasure. he’s having the orgasm, you’re not. i have a suggestion for all you women who “love” anal sex for whatever reason (masochism, finding it ‘sexy’ when he dominates you, whatever): watch the video “bend over boyfriend” and strap it on and DO HIM. i’m sure that all the manly-men you’re with will find that terrifying at first (“dood, i ain’t gay”, “bitch, *I* be da mann!”) but, in my opinion, if you’re gonna have to take it, you should also learn to give it. and, given the prostate, chances are he’s gonna love it (since that seems to be your–and his–first priority anyway).

    “my straight friend told me that of course sex with men is painful at first and chances are you’re not gonna come anyway, but you just need to keep doing it to break yourself in. i told her that i don’t need to, or want to be broken. five years later she’s still saying ‘the best part is before, when i know he wants me, and afterwards, when he holds me.’ and still asking me what two girls could possibly do in bed without a penis. i say, ‘have orgasms’, as she chugs more cranberry juice to counter that nasty urinary tract infection and wonders if there’s anything else she can do to make anal sex less painful because he likes it when she’s in pain but she doesn’t.” –overheard at a gay bar.

    maybe she should read this article. after all, never mind making art, music, learning a new sport, or masturbating…all women owe it to themselves to make every hole in their body the perfect spot for THE PENIS!

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  36. Is anal sex a more challenging procedure when the female has a large rear? I’d like to know this before attempting anal sex with my girl.

  37. I can’t think of any reason it would be

  38. it IS important to work your way up to a really big penis1 When I first tried it I thought it was impossible but now I can take some really big ones! thing is, Ive had as much pleasure with small or medium sized penises as I have with 8″ ones. I think most guys would agree with that. Sometimes I wish I could return the favour but mine doesnt work anymore after years on hormones!

  39. Alexanne,

    This dynamic is not unique to the het world, and I don’t really think there is anything wrong with it. I wouldn’t, since I participate in it. My partner takes me anally with a strap-on often, sometimes almost every night. I don’t really receive that much physical pleasure from it, in fact sometimes there can be a lot of pain, but the mental pleasure (meta pleasure as you call it) is intense. Yes, I enjoy it that she enjoys it… she is a lot older and smarter than me, and is very successful and accomplished, and being penetrated and in a position of subjugation to someone like that is very exciting to me. In fact, while she does get physical pleasure, a lot, maybe even most of her pleasure is meta as well. I am young and, to be frank, very pretty, and she has expressed that she is very excited by the feeling of sexual conquest over me. She uses a very large dildo to intensify this, what I would call “ego pleasure” (which is why I am here, since I was a bit worried since I am small and a little afraid it might be too big and causing some damage). And yup, its pretty clear that she likes my pain. And she is very (very) able to orgasm from this, meta or not.

    My point in telling you this is that physical pleasure isn’t everything, not by a long shot. If it was we could just use a vibrator and be done with it.
    Isn’t it said that the mind is the largest sex organ? “Meta pleasure”, I can personally attest, is nothing to sneeze at!

  40. That is good so how about if she cries when i put it into her ass

  41. You’re not doing it right. You’re hurting her.

  42. Isma,
    Does it hurt when she jams a big cock in your ass?
    Learn some patience, take your queues from your partner.

  43. will i have read all comments on are big penis safe
    i am a male and i have a new friend in my life we hang out i enjoy having oral sex with him but he want to now Preparation me anally
    he is a black male with a 9.5 by 7.5 thick so as far as i can tell everyone on he saying i should be able to take his penis full size as long as i lube up every will

  44. Yes, and take it slowly Enjoy the process of working it in. That should be part of the fun. You’ll feel a real sense of accomplishment when you’ve taken it all.

  45. should i start off in the doggy position,
    what would be the best position to start off with
    and will it be safe after i have taken the full 9.5 inches of his man hood to start pounding my ass hard and deep is it safe with a cock that huge
    i mean a 9.5X7.5 is no small cock

  46. No, it isn’t, but if you follow the advice in this article, you should be fine. The missionary position is the best to start with. “Slow” doesn’t just refer to putting it in. He should also warm you up with long, slow thrusts until it starts to feel good to you, and you’re ready for him to give it to you deep and hard. A lot of the problems with anal sex are due to the active partner not knowing what he’s doing or being too eager and not caring about his partner.

  47. I am getting to know a Woman I met through work, Who I found out is Transgendered, I love her and she is beyond beautiful, the only possible problem is ” and it is true I measured it ” She is 14 inches and 9 around! I have never even done Anal nor has she “giving that is” it turns both of us on so it is going to happen but am I safe? She has been married before so she knows what to do take it slow etc.. but I am a bit afraid of that part of her .. She is understanding and I am using toys to get ready, any advice? Can she go in all the way eventually?

  48. The world record for penis size is held by Jonah Falcon at 13.5 inches. It’s amazing that you’ve found a transgendered woman with an even larger penis than that.

  49. It’s nearly impossible to find educated people about this topic, however, you sound like you know what you’re talking about! Thanks

  50. If she is that big I would love to try to take it with you.

  51. I have a similar problem like willie above, though it is not *that* big. it is still really big though. it is very long, but the problem is the girth.
    i never thought of myself as gay before meeting her, but i want to be a part of her life so badly. she has so much going for her, she is brilliant, and gorgeous, very kind, and very passable, which is important to me. And she keeps saying she cant get over how beautiful i am. she is an exclusive top, so this is a really big problem. when we tried we did the relaxation thing, we made out in her hot tub and she took me to her bedroom, she had it set up with candles and soft music, she spooned me kissing my ears and neck and used lots and lots of lube and was very slow and gentle, but it was just too painful. i wanted her to keep going anyway but she refused. i couldn’t help but be scared and im sure thats part of the problem.
    the thing is like i said i didn’t even think i was gay, im only 19 and still a virgin when i met her, i guess i still am. i am so scared, and worried about the sex part. i am very attracted to her physically and as a person, but im very conflicted about the gay aspect. i like her penis, the way it looks, i like the way it feels when i masturbate her, and i even dont mind licking it, i love the way she reacts to that. but i wish we could leave the sex at that. i wont tell her that though, she wants to penetrate me so much and i feel like i cant refuse that. if it wasn’t for her wanting it so much i wouldnt want to at all. but she has been so nice and patient about it, she said we have the rest of our lives to do it, which made me so happy to hear. And the thought of her leaving me makes me feel sick to my stomach. well sorry if that was tl/tmi

  52. its so easy to fuck girl’s ass without pain ,i am so expert in that if any girl like to know how ,i am ready to learn them free & make them so interest in anal sex ….

  53. isnt it true that girth is much more of an issue than length of the penis, esp when it comes to anal? Why does everyone talk about length always? a 2 3/4″ thick penis is pretty challenging to take anally i think! (still working on it with my guy… ;)

  54. Yes, girth is more important, but length is easier to measure. Longer penises are thicker than shorter penises on average, but average length penises can be thick, too.

  55. yes but how does one work up to 2 3/4″ thick (ie over 8.5″ around)?

  56. I am transgender mtf. Thank you for the tips. Now I know I will be able to fit big men in there. I have had an 8 inch in till his balls were slapping my ass. Anal sex is wonderful with the right man.

  57. I love a huge one balls deep in my butt, pounding me hard and creaming my crapper to the max all day long.

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