A
male
age
41-50,
anonymous
writes:Hi, i need some advice from the ladies. I have a wonderful girlfriend and we love each other very much. I love her to bits and she is super hot. I would like to have anal sex with her, i noticed that when i touch her, or lick her there, it arouses her very much. I want to be respectful when i ask to, i just dont know how to ask or when. If she agrees to try it i want to make her feel good, i have read that usually the first time is painful and unpleasant for the girl. I dont want her to feel that. Do you have any suggestions on how to ask her and how to do it? I mean which position, how to be gentle, what to tell her while doing it, any tips?
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female
reader, So_Very_Confused  +, writes (11 December 2012):
 It's not just the first time that hurts. IT HURTS.
I agree with Ciar totally.... if she agrees to try it it may be a one shot deal.
I also agree with YouWish in terms of technique.
I want to add not only should you be well washed... please cut and file your nails very very very short.... ragged edges will hurt worse.
IF she agrees to try and then it's too painful you will have to accept this.
also NO oral or vaginal play after anal play without serious soap and hot water washing... e.coli is NOTHING to mess with. YOU should wear a condom to avoid potential UTIs which in men are NASTY....
Also my personal advice. SHE LEADS.
in other words after MUCH foreplay and lube and relaxing (we are talking hours... this is NOT an event to be rushed)
when she is ready she should lie on the bed belly down with a pillow under her hips... relaxed... she's lubed, you're lubed... you press lightly against her anus and then you wait. talk nice... once SHE feels comfortable (it could take a few minutes) SHE presses back onto to erect well lubed penis... you just stay still... she presses till she feels too much pressure/discomfort... and she stops. she does not pull forward nor do you pull back.. you just STOP at the position you are in and you WAIT... talk nice... kiss her back if you can reach it... reassure her you are waiting till she is ready.
When she feels ready again she pushes back some more and you start all over... she pushes some more till she is uncomfortable but not in pain.... PAIN Means STOP... disengage and try again some other day IF she is willing.
you keep at it this way giving her total complete control over the amount of penetration on her terms, at her speed....
this could take over an hour.... there is nothing quick or down and dirty here... it's a slow gentle process...
This is how I was taught... and while I don't suggest anal intercourse as it really is NOT exciting for the woman in any way shape or form in most cases, I understand to some extent why men like it... and it can be a nice experience for a woman in love with a guy to know she's doing something he really wants....
A
female
reader, anonymous, writes (11 December 2012): Alcohol isn't exactly a good way to get honest answers from people. If someone's drunk or tipsy, he or she tends not to think properly.
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A
male
reader, Yos  +, writes (10 December 2012):
 Ok i'm being misunderstood when I say ask when drunk, so i need to clarify.
What I mean is you want an honest answer from her. I said you could ask when you are both drunk, but at the same time out of the house somewhere. In a situation when you are obviously not about to have sex, because you are fully clothed and in a public place! Clearly you are struggling to have the courage to ask her directly, and she may lack the courage to give you an honest answer. Put yourselves in a situation where you can speak your minds. Alcohol can aid that.
Why? Because you want to have an open and honest conversation about it. Being a bit drunk tends to have people speak their minds.
At the same time, since you are not in a situation where you are about to have sex, there's no pressure to have sex. Instead you are talking about sex, what you like, and what you don't like, in a situation where you can do nothing more than talk about it. This is important: if she feels you are asking because you are putting pressure on her to do it now (or very soon) then you're not going to get the honest answer, and all sorts of bad things could come of that.
I absolutely do not recommend you to have anal sex for the first time drunk. You need to be very sensitive and aware when you do, and being drunk gets in the way of that.
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A
female
reader, peteloevely  +, writes (9 December 2012):
 Please, please, please, DO not do it while drunk, make sure you both know what you are doing…Plus for what I read from 99% of anal posts you have to concentrate on stimulating her clitoris, other ways there will be no pleasure for her… I cannot attest, but that is my two cent. Good luck, you yourself might find out you are not that in to it after you try it, I have seen it happen, fantasizing about some stuff is hotter than actually doing it, but of course not for everyone.
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A
female
reader, anonymous, writes (9 December 2012): Do not try this or ask her when either of you are drunk as one poster suggested...that's very immature and incredibly irresponsible of anyone to go about anything new in this manner. Seriously....You need to just ask her. Don't beat around the bush, make crued anal sex jokes or take her response personally. It is quite possible, she's already had anal sex before and would love to or she had a bad experience and won't ever do it again, won't even consider trying it, or is willing to try it with you...whichever way it goes, the worst she can say is no...right?If she trusts you and feels secure and agrees to this, take it really really slow and if at any time she is in discomfort or feels pain, stop at that moment and go wash your penis before you engage in any other sexual activity. You can try again another time when she's ready. If you don't stop or hurt her, that might be the end.She needs to communicate and you need to listen. You can ease entry by either you are her, gently rubbing her clit.
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A
female
reader, Honeypie + ♥, writes (9 December 2012):
 I agree, just ask her and RESPECT her answer. If hell no is the answer then that means hell no - not OK, ask me again in 5 days....
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A
female
reader, anonymous, writes (9 December 2012): I think the best thing you can do is ask her. Ask her when you are both feeling very close and relaxed. Be mature about it, and express it's something you would very much like to explore with her, but you completely understand if she does not want to.
Having anal sex takes a little prep, so give her that privacy and advance time to think about it and be ready for it both physically and emotionally, if she is receptive to the idea. Anal sex, if done right does not hurt, pressure at first yes, but not pain. It requires a lot of lube, your partner to be completely relaxed and aroused. If there is any tension or fear it will be painful and could cause her damage. Do not think you can just go from nothing to penis insertion. And please, please please, do not do this is a manner you could have possible seen in a porn. I am just throwing it out there because too often men watch this stuff and think that's the way it goes....well, no, not even close.
I personally enjoy having anal sex. It's very arousing. However, it took me almost a year with my partner on and off of trying, to finally get it right and figure out what worked best for initial entry. Again, this may not be for anyone else, but for me, him entering from behind seems to work without any pain and after that, we can go in almost any position, but I have to start the same way. And even after another year or so of enjoying this, entry is still very lubed and very slow. Perhaps I am just cautious, I don't know, but I'm 46 and I don't want any damage that will haunt me down the road if you know what I mean...
If she is dead set against it and shuts it down without any further discussion, then leave it alone and put it out of your mind...there are plenty of other things you can do with her. She may down the road, change her mind and you can revisit it then.
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A
female
reader, anonymous, writes (9 December 2012): I'd listen to the first two answers.
She should not be drunk when you ask her nor should you.
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A
reader, anonymous, writes (9 December 2012): No No NO! I know this from experience that it hurts like HELL! My bf tried to seduce me in the same way by licking me down there. It felt good :) Then we had anal sex ( I thought I would give it a whirl... OUCHHH! I bled and it hurts so much... :( We were both not happy about that... I was well lubed too...
I guess some people like it and some don't. ;)
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A
female
reader, anonymous, writes (9 December 2012): I agree with a comment that you need to ask her. Personally I don't know how any woman can like it. I tried it several times, it's just gross. It hurts, I had a feeling like I want to poop, sorry but that's what I felt. I had no pleasure what so ever. One thing is to like when it is touched, another when you stick something in there. For me it felt like enema.
I understand that it's much tighter than vagina, but aren't you guys afraid that you will have a little accident in bed? I heard these things happen, yuk.
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A
male
reader, Yos +, writes (9 December 2012):
Since she gets aroused when you touch her there she's quite possibly going to like it, even love it.
You can try just asking. Maybe wait till the two of you are out somewhere, and drunk. The advantage being: you're both drunk, so its easier, plus since you are out it's not like you are saying 'lets do it right this second', getting you hopefully an honest answer.
The other option is to indicate you want to do it physically. In that case just do what you normally do, then use a finger, and see how she responds. If she enjoys it, use a second finger. If she still enjoys it then you are probably good to go. Just be very very gentle, go very slow, ask if she's ok, and listen to her body and her reactions. Also bear in mind that it's something that shouldn't be over-done and for which there is definitely a time and a place: pick your moment in other words.
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A
female
reader, YouWish +, writes (9 December 2012):
 I agree with Ciar and count yourself very lucky if she's game to try.
If she says yes, don't just go from zero to penetration! You know that lubricant is absolutely critically essential. Do not take anything you see or have ever seen on porn as learning material or any kind of example.
Also, she must get used to it. Try using gentle lubed fingers (well washed!) to get her used to it, then just try touching your penis against the walls of it, also lubed. Don't just lube your penis, lube her too. Then simply trying pressing gently against it...you see the pattern here? You have a long way to go from her saying "yes" to you going balls-deep, if you pardon my expression.
What might help as well is if, after she agrees, that BOTH of you study up on techniques and the best way to keep it safe and good. NEVER go from anus to vagina, because that can do her a *LOT* of damage in terms of infection.
Also, you might want to reconsider anal if you're the type of guy who must be ultra rough to have stimulation. Anal skin can tear badly if you need to pound like a jackhammer to get off, and then we're talking irreparable damage to her sphincter. Don't masturbate for a few days before you go for the full anal experience. The last thing she needs is for you to damage her by too much friction and jerking around.
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A
female
reader, Ciar  +, writes (9 December 2012):
 I suggest you just come right out and ask if she's willing to try it. If she is, there are plenty of online articles that provide step by step instructions.
Having said that, please be aware that while some women truly enjoy this, it really isn't anything to write home about for most. It's far more thrilling for the man but most women get very little out of it. So if she does agree to try it, don't assume that means she's game all the time. It may be a one time thing. If so, be grateful she was even willing to try it, then accept it and don't mention it again. That includes joking and hinting about it.
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