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My boyfriend likes anal sex but it hurts

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Question - (29 December 2010) 9 Answers - (Newest, 30 December 2010)
A female United States age 26-29, anonymous writes:

My boyfriend and I have been talking about anal sex since after we had vaginal sex. So, it's been about six months now... We had anal sex (barely) once before and it hurt like hell. I ended up crapping blood for a couple days after that. That was about a month or so ago.

Well, my boyfriend still really wants to do it. He's not pressuring me or anything but it's just one of those things he really wants to do. How do I get myself more comfortable for it and make it pleasurable for both of us?

View related questions: anal sex, vagina

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A male reader, anonymous, writes (30 December 2010):

Double M...are you a doctor? Do you really know that anal sex leads to hemorrhoids or cancer? Truth is there is no direct evidence to support your comments. giving out false medical information is extremely dangerous. don't do it. Keep you r personal opinions and values on anal sex separate from factual medical aspects of it.

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A female reader, dmartin89 United Kingdom +, writes (29 December 2010):

dmartin89 agony auntThe first time I had anal sex it hurt like hell, but I found I was doing it all wrong. I was on top and I didn't use lube, and I bled for days unsurprisingly!

The second time was fun and enjoyable. We used lots of KY, a condom, had some red wine beforehand and worked eachother up so we were excited to do it!

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A female reader, anonymous, writes (29 December 2010):

If it hurts you then don't do it. Buy a very larg strap on and penetrate him and see how he likes it.

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A female reader, xanthic United States +, writes (29 December 2010):

xanthic agony auntThe real question should be is this something YOU want to do, or is it something you want to do only because he wants it? After that experience, I'm surprised you're even considering it.

Lubricant can help a lot, but there's no guarantee it's not still going to hurt.

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A male reader, rivi United States +, writes (29 December 2010):

You have advice here from the feminist perspective - which is fair enough. You decide whose advice you want to follow.....

Here's some from that of a guy who totally understand and sympathises with yr bf ; and also thinks he's really lucky to have a gf who is willing to go the extra mile to give him total sexual experience and satisfaction.......

You may not actually enjoy the physical sensation of being anally penetrated...... but you may well enjoy the feeling of giving your bf the extreme pleasure sensations involved.... the intimacy and closeness... and it does not have to hurt.....

My experience is if he can get you as relaxed as poss with a load of foreplay around your vagina / clit / nipples.... then he can move on to paying attention to your anus with plenty of lube and introducing first one, then two, and finally three fingers at a time into you..... just an inch at first, then the whole length of the fingers, bit by bit..... you should find it acceptable and even enjoyable. After you are comfortable with the three fingers he should touch his condomed and lubed penis into you..... just an inch or so at first..... progressing gently to the full length of the shaft.......

Even if it is true what others have said about the anus not being designed to receive anything inside it..... in my , and some of my gfs' experiences penetration can still be a source of pleasure, even for the girl...... And your bf will worship you !! [ if that's a plus for you.....]

Let us know if it works out for you.......

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A reader, anonymous, writes (29 December 2010):

if your going to do it, the main thing to remember is to RELAX! that's about the most important part of it, go slow and relax, have him wear a condom, and use some k-y or something like that also with the KY dont just rub it on the outside and go for it, insert your finger a bit into your anus, that will help as well. also it can help your enjoyment of it if either you or him manually stimulate your self during anal. It can be very enjoyable if done right.

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A female reader, Tisha-1 United States + , writes (29 December 2010):

Tisha-1 agony auntYour boyfriend injured you enough to make your anus/rectum bleed and he wants another chance? Really?

One thing on these anal sex questions, is that it's something that can be a two-way street. He has an anus and a rectum as well, so he can experience anal sex firsthand, just like you did. My advice is for him to experience anal penetration, perhaps seeing how it feels to have bloody stools and pain for several days afterwards, maybe then he'll get some understanding and sensitivity for what you went through. Buy a dildo that has a diameter sufficient to match the size of his anus, relative to the size of his penis and your anus, just to be fair. Take a look at the diameter of his stools in the toilet, relative to yours. I expect you'll see a difference.

As DoubleM points out, the anus is designed to expel things, it's not really set up for penetrative sex. If you really want to do it, you have to be sufficiently lubricated and learn to relax. Again, it seems logical tht he'll be better able to understand the problem after he experiences it himself firsthand.

Take care!

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A male reader, PeterPan United States +, writes (29 December 2010):

PeterPan agony auntI would highly recommend reading this book. I consider it (and many other by this same author) an excellent reference to understanding how to safely start experimenting with anal sex.

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A male reader, DoubleM United States +, writes (29 December 2010):

DoubleM agony auntWell I think that a lubricant, such as K-Y Jelly, might somewhat ease the discomfort of anal penetration. But please realize that the rectum and colon is designed for excretion, not penetration. I'm aware that potential problems can include such nasty problems as painful and lifelong hemorrhoids, pervasive rectal bleeding, colitis (infection of the colon), diverticulitis, colon or rectal cancer and other maladies. As a respectful man, I've never subjected my wives or girlfriends to anal penetration for the aforementioned reasons.

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