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Start with cunnilingus...and a finger

The very very best way to go about anal is to begin orally: for me at least, a finger in the ass makes cunnilingus about a million percent more enjoyable. a few orgasms into the session, another finger can be added. a few minutes of this, and you'll be practically begging for anal sex... and you'll be both physically prepped and mentally ready for it.

Intensely intimate act - Anne, Age 35, Nova Scotia, Canada

I tried anal sex seven years ago with a former boyfriend. It was a spur of the moment decision, no lube, no nothing. He got inside me gradually, uncomfortably... and then I asked him to get out. There was nothing pleasurable about it. After that, I had two more boyfriends who were very interested in anal penetration and stimulation. I let one boyfriend stimulate my rosebud, but found nothing pleasurable from it, in fact, all I could think of was "there's a finger up my ass!" And again, this was with no lube. I refused to engage in any anal stimulation with these other two partners, giving or receiving.

That all has changed with my current lover and partner. I feel a deep connection with him, which has allowed me to let go of my inhibitions and trust him and the situation. Most importantly, before we ever tried anal sex, my partner communicated his desires to me, desires he'd had for a long time but had told nobody. He felt safe enough to talk to me about them because I had been so open in talking with him about sex, sexuality, and sexual desire. He told me about all the research he had done on the topic- for example, use tons of lube (if you think you have enough, use even more!) and that the woman needed to be in total control of the situation. His understanding of the most safe and pleasurable way to do it, and his respectful and thoughtful communication of that (rather than in a laviscious, crude way) gave me the courage and motivation to try it again.

When we finally did do it,  he emphasized that I was in total control, and he was absolutely respectful and sensual in his actions and communication. Although I couldn't handle his being inside of me for too long (I'm anticipating and hoping that this will change in the future!), it felt very pleasurable (and rimming- yum- oh, that felt gorgeous too), and it also gave me *intense* pleasure to know that I was fulfilling a long-time desire of his. Most importantly, engaging in anal sex with him was an intensely personal and intimate act, and made me feel much closer to him, perhaps because I had opened myself up to him in a such a vulnerable way and had trusted him. Likewise, he is beginning to trust me also. I engaged in anal penetration with him (with my finger)- something he also had desired. We hope some day to engage in much more anal play in the future, and to "up the ante" so to speak!

My partner has gotten me more in touch with my ass than any man ever has, and I am both grateful for that and excited by it! The second time we did it, we used mirrors so that I could see him behind me-- views I'd never had before. This was *totally* arousing. I wish we had taken pictures. Now, I'm scanning the internet on a regular basis for pictures and stories of anal sex, and longing for the next time when we can touch one another in that manner again!

Explore each other - Sharon, Age 38

What tips can I offer on the subject of anal sex?
First: I think that we as women need to discuss anal sex beyond and outside of the context of women being penetrated by men. This context is too narrow.
Second: To enjoy it you need: lube, patience, the right lube, to feel safe, self-awareness, more lube, a willing partner, a patient partner, communication, knowledge of your partner, curiosity, and trust.

Lubrication is essential when you first experiment! If you are starting to explore this aspect of love making it is essential that both partners become familiar with the sensations of both giving and receiving this form of loving touch. By the way: not all lubricants are the same. I like sesame oil and Astro-Glide.

My second boy friend introduced me to anal play when I was 20. The first time I invited him in to my bed he rather gently put the pad of his thumb over my anus when he was eating me out. I was quite startled and momentarily fearful by the sensation at first. But he did not try to penetrate me and within a few of minutes it felt normal. He varied the thumb pressure a bit from time to time and he moved his thumb around a bit. I felt good. Then we changed position and his hands went elsewhere. Looking back this was the turning point for me. I felt safe when he touched me back there and everywhere else.

Explore yourself:
Later that evening I tried touching him in a similar manner and he responded favorably. My curiosity about exploring anal sensation further was activated. Soon I experimented with anal penetration when I masturbated. Point of advice: Start small and use lots lube.

Explore each other:
The next step in my discovery process was reading about prostate massage in some book. That night in the middle of a restaurant I asked my boyfriend if he wanted a prostate massage when we got back to the apartment. I then had the dubious honor of explaining what I had in mind. He said that it sounded "interesting" and that he would like to "give it a try some time." But he was obviously a bit nervous about the idea. That night my boy friend explored my anus with his fingers for the first time. The next morning I woke up EARLY, my boyfriend was sound asleep (he was not a morning-person). I lubed up my hands and I woke him up orally and proceeded to give him his first prostate massage.

Eventually I found the courage to have my boyfriend penetrate me anally. That experience was the most joyous loss of virginity of my life. We were relaxed, trusting, prepared, and ready.

Warming up with lube - Carrie, Age 43

Guys, pay attention to the girls on here--they have it right for the most part. 

My husband and I have been enjoying anal sex for more than 5 years now, and it's great but only if both partners are considerate.  The man, especially, needs to be patient.  Rob's cock feels great in me, but only after 10 or 20 minutes of foreplay and LOTS of lubricating. 

Here's a tip we learned:  Before we begin, he takes two syringes from an old Delfen foam birth control kit and fills them with KY jelly (from a tube).  These syringes are clear plastic, they come apart for cleaning and they are very smooth. 

Then I let him start by massaging my anus with the really slippery KY that comes in the bottle (not the tube stuff).  He uses a latex glove because no matter how clean I feel, it still grosses me out for him to put his bare fingers on (much less IN!) my anus.  Once I'm relaxed (and usually moaning a little) he starts putting his fingers into me.  When I tell him I'm ready, he slides each syringe into my butt and "fills me up" with KY Jelly.

By this time I'm ready, and he can put on his rubber and lube up his cock with some of the KY from the bottle.  He also puts some more of the bottle KY around my anus.  I can't emphasize enough that you have to use a LOT of lube.

Once he's done all of this, his cock usually slips right into me with no resistance or pain.  Maybe some couples need to work it in and out some, but it goes right into me.  If I feel any pain at all, Rob senses it and stops immediately.

Anal is a lovely, very intimate way to have sex.  I wish you much enjoyment if you decide to try this with your lover.

Start with fingers and vibrators - Age 23, England

Let's be honest, it's a bit naughty, anal sex.  That's a turn on in itself.  Men also appreciate that it's quite rare for a girl to like it, so they tend to get quite excited at the prospect (bless them).  Don't let them rush in.  Warm up properly and for God's sake, LUBE.  I can't stress that enough.

I lost my anal virginity to a bloke who was pretty selfish and probably not that experienced in the area (with hindsight).  It hurt.  Lots.  Why?  We had no lube and he didn't take his time.  Consequently I wasn't relaxed and it almost put me off.  Almost.

Still with burning curiosity and the belief that it would be amazing with the right person, I tried it again. The second time was with a different bloke who knew what he was doing and it was an incredibly intense, full feeling that I enjoyed immensely.  He played around with the area for ages first, then lubed, then slowly eased his cock in.  It took about 5-10 minutes for him to fully penetrate because he would insert it an inch or so and wait, then pull out and push a bit further and wait etc. etc. until I was fully relaxed (and very turned on!).  After that, full penetration was easy and intensely pleasureable!

Prior to trying anal sex with a bloke I'd experimented with toys and my own fair hands.  I recommend fingers and anal vibrators to start with, and for a really amazing orgasm, use a vaginal vibrator at the same time and, if you can manage it, stimulate your clit with yet another vibrator.  Sounds complicated but it's worth it.  It also get you used to having something up your arse because it is quite a weird feeling at first and psychologically, it takes a bit of getting used to.

Stick with it, is my last piece of advice.  It's a unique feeling that is completely different to vaginal sex and worth experimenting with.  Just don't forget to lube..

Listen to your lady - Nebraska

All I can say is that you guys need to listen to your women.  I have had more than one experience with men that don't listen when I am giving them directions on positions and speed.  I happen to enjoy anal sex alot, but not if I am in pain.  The biggest tip that I can give you men is to let her lead you, even if it's not the masculine thing to do.  She will only be leading you for a short time before you can take up the reigns and take the wild ride if you do it right.

Clearing the Way - Age 27, South Carolina

I use an enema early that morning when I know we are going to do it that night. Or I'll take a gentle laxative the night before. That way in the morning I'm all cleaned out. Trust me it helps to know that nothing is in there while he is going in. And like these other women said, get more lube. Makes everything feel so good!

Girls Love the Lube - Jude, Age 30, UK

A simple rule to remember before having anal sex: "Too much lube is almost enough." Always put more lube on/around your partner's anus than you'd expect to use.

Unvarnished Truth - Los Angeles, Age 35

Lube of course is very important. I did notice a few who forgot that all important thing. Spit does not work fellas; sorry, wrong answer. There is no lube in my asshole and all though I really enjoy anal I do make sure all is lubed and very clean first.

As far as watching pornos is concerned not a good idea. Pornos are made for men not women and they edit out the parts where, like one of the more tactful gentlemen put it, patience is a virtue. 

Girls in pornos are simply pretending to like it most of the time. After all they are being paid to be good actresses. There are many things going on behind the scenes you are unaware of. After all it is just a movie and not real life. Now for the good stuff. Personally, I love to be licked all over and this includes my asshole especially when a man fucks it with his tongue. Fingers are nice if used gently and not rammed up me without proper lube. Toys can also work well with me if used properly. Thing is you need to ask questions especially if it is your first time having anal with a lady. Also, please make sure you are very hard before you try or else you will hurt the lady.

To Enema or Not to Enema - San Francisco, Age 52

One woman advised to use the bathroom before anal sex. I have found it is cleaner if I have not had to use the bathroom for at least an hour before having anal sex. Also, having an enema before anal sex may make the woman more susceptible to bacteria introduced into her colon if she participates in unprotected anal sex, so one should consider if this is the best way to proceed. If a condom is used, an enema is unnecessary anyway, isn't it?

When the man is entering me, I push out, as if I am trying to void. Doing this relaxes my sphincter muscle and opens my anus. If we have used enough of my lube plus KY to make me nice and juicy, he will slide right in.

I have some of my most astounding orgasms during anal sex. There are so many nerve endings in the anus, the stimulation is extraordinary. Also, it seems that men get extremely excited by women who love anal sex, so the emotional atmosphere is super-charged.

 Takes practice - New York

The first time I did it, I remember my boyfriend just sticking it in and I had the worst pain. Sex was a dead issue after that! But a few months later, I opened my eyes. I started with lots of lube and a small vibrator. Eventually my boyfriend worked me up and I had anal sex for the first time. It's not something we do all the time, but if we are drunk or loose ourselves a little, we will do it. Sometimes I am in the mood for it. I also have begun penetrating him a little. He has the best orgasms when I do it. Don't be afraid, just go slow and relax. LUBE LUBE LUBE

On my stomach - Age 20, Riverside, CA

Lying flat on my stomach is better for me when my husband inserts himself. After a couple minutes of going slowly he can fully thrust himself at any pace he wishes.

On his knees - Age 18, North Carolina

I always like to start out with a deep session of getting eaten out... just to get hot and wet. The best position I've came to love is me laying on my back, with my future husband on his knees between my legs. It doesn't hurt at all, it only feels great. He plays with my clit while he's making love to me anally, this makes the orgasm more intense and hard. Oh, and don't forget, lube, lube, lube, lube!!!

Practice by yourself - Age 30, North Carolina

I recommend, first and foremost, patience and lots of lube. Experiment with different lubricants, K-Y is not the only lubricant out there. My personal favorite is I-D Glide.

Experiment by yourself in the shower using a small dildo and lots of lubricant. Do not be afraid to enjoy the sensation or be shy about asking your partner. It turns out when my husband and I saw anal sex in an adult movie, we both ended up admitting we had been thinking about it for weeks (think of all the fun time wasted).

Go slow at first. I personally like to enema first and shower. That way there are no inhibitions about the "gross out" factor. That way you BOTH are free to enjoy the experience.

On your side - Anna, Canada

1) You need and want to use lube. It may be painful the first time but ahhhh.. once you try it and if it's done right you will love it!

2) Always stimulate the anus before, be it with a finger or whatever.

3) Lying on your side is much easier for you and for the guy. Since it is very tight and new this is easier and better for both make the experience more fun. As you get used to anal sex then you can work your way to sitting on top of your man.

4) ENJOY!!!!!!!   It is an incredible feeling to cum while you're having anal sex!!!!  YUMMY! 

PS:  If you fear that anal will be messy and you're very nervous about it, get an enema kit!!!  Cheap @ Wal-Mart and no need to be ashamed.

First poop - Nicole, Florida, Age 22

Make sure you poop first or else his cock will compress all your poop and it's gonna be really hard to shit.

Try on your own first - Annabel, Chicago, Age 19

The first time my ex and I did it, it hurt. I asked him to stop and we didn't try again. Now that I am single, I think about it a lot. I read up on the subject and I learned a lot of things I wish I knew the first time I tried it.

After some research I decided to get myself a small dildo and try it on my own. I got lots of lube and I masturbated for a while, and when I got really turned on I went for it. I was really relaxed and I went very slowly at first. It wasn't long before I was inserting the dildo as far and as fast as I could. All it took was some getting used to. I recommend trying it with small toys and your finger before you go in with the penis. It's just too large. If your lady is shy about trying it with you, ask her if she'd like to do it alone, see if she likes the sensation, she might be at ease when she realizes it is really pleasant and relaxing.

Another thing I recommend, talk about your concerns. I bet most women might be shy to try it because they are afraid you might get grossed out. Explain to them that no matter what happens, it wont turn you off, and you're understanding of the fact that the anus isn't the cleanest area of the body, even after you're showered.

Make her trust you, show her that you care for her and no matter what you will stay just as attracted to her as before. Insecurities for women ruin a lot of good sex.

Get wet - Poplar Bluff, MO

always find that anal sex is a lot less painful the more turned on I am. I never let my husband hit the back door until the front door is sloppy wet.

Hop on top - Australia, Age 20

As a woman who really likes anal sex, my best bit of advice to first time girls is sit on top of your guy so you are in full control. It can be a teeny bit awkward but it means you're in full control of how far/hard/fast things go. Plus, he can play with your clit and pussy while you fuck him. It drives guys wild.

Don't ignore the clit - Dallas

Be sure she uses the restroom beforehand! You don't want anything on yourself when you pull out, do you? Ugh. Anyway, I absolutely can't do it unless I'm getting some sort of clitoral stimulation at the same time. As long as that's going on, it's fun. Get her to use a vibrator, or even a dildo while you're busy back there, and it should be pleasant for her.

Listen up! - Karen, Michigan, Age 22

Patience! and Plenty of KY! Start slow with something small. Make sure she knows that she/he is in charge and if they say "No," or "Stop" then you immediately stop. It may not work the first time but if she trusts you, and you've listened to her in the past, she'll be willing to try again! Hello fans!

Stimulate the clit - "A chick who likes it," New York, Age 29

My boyfriend and I have been doing it for a while. First step is to start small. For instance, use your lubed up pinkie finger during oral sex or any other clitoral stimulation. It's also really good to use a small vibrator/dildo or something like that. 

The most important is clitoral stimulation, I think if you play with her clit during any kind of anal play (including anal sex) she WILL COME REALLY REALLY HARD -- like fireworks will go off an violins will play. This will make her want it again.  There's my two cents.

Dos and Don'ts - mjcat, Ohio

What you need to get started: 

  • Patience, lots of lube (I recommend K-Y, it's what the doc uses lol), and intimate knowledge of your partner!  


  • Do talk about it a lot!
  • Do be gentle in manner and action. Let her tell you how she would like it.  
  • Do experiment slowly with fingers and small toys, and remember lots and lots of lube!!!  


  • Don't be pushy.
  • Don't be disappointed if the first few times it doesn't end up in the end the way you wanted it.  
  • Don't give up. If she is willing be persistent and always gentle and supportive. Try, try again. Believe me it will work and both will have the greatest pleasure either could have ever imagined!!!

Wash up first and lots of lube - Anonymous woman, NY

I never gave it a second thought. Me and my guy never even talked about. We were fooling around one time, and it slipped in. We didn't pursue it, but because I was so wet at the time, it didn't hurt. I was interested in trying it fully, so I suggested getting some anal-specific lube, and it *really* worked well. It slipped right in with no pain. Never try it without lubrication, that's the biggest key. 

He did it very slowly, because the pressure inside can be uncomfortable if it goes too fast on first entrance, as well as any normal discomfort of having something a couple times the size of your asshole plowing in. This is something that takes a lot of relaxation and trust for a female who is an anal virgin. If your girl shows in other ways that she is into new ideas, this might be easier. If she feels gross about it (it is after all her ass) prepare her by showering together so she feels *clean*. I read on a gay website somewhere that the person on the receiving end should make sure they shit before they try it, so you might want to gently suggest that as well. All in all it wasn't a bad experience for me and it certainly wasn't painful.

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