May 072014
 

I have recently started a new relationship, and we have been getting to know each other including experimenting a little with different sexual things. The topic of anal sex came up and she is turned on by it, but so far her rule is “two fingers max.” She’s a very small person all around, and that includes her asshole. She wants to stretch her ass to accommodate my cock, so we want to know how to do it and how long it will take.

–Patient in Palo Alto

Her small stature does not necessarily have anything to do with how much cock she can take in her ass. Haven’t you seen those tiny porn starlets take huge dicks up their butts? It is absolutely possible. Her objective should not be to stretch her ass, but rather to learn to relax the sphincter muscles to make penetration comfortable and pleasurable. I suggest you begin slowly. Try one finger in her ass, your tongue or fingers or a vibrator on her clit, and a rousing orgasm. From there, let her set the pace as you work your way up from one finger to two, and so on. You can also work your way up with dildos or butt plugs in graduated sizes. You shouldn’t move on to the next step until everything feels great. How long it takes to get used to this new sensation, be comfortable with anal play, and work up to a cock in her ass will totally depend on her. Don’t be so focused on how long it will take, just enjoy all the fun you’ll have getting there!

Feb 052014
 

My girlfriend knows that anal sex has been a long time fantasy of mine, and recently she decided to try it. We were in the shower fooling around, then we had vaginal sex. She suggested I put it in her ass, and, of course, I gladly obliged. I gently placed my dick at the entrance of her sexy asshole, and she pulled her ass cheeks apart for me. I slowly tried to push my dick in her ass, but it was like pushing my dick against a wall. I was just not going anywhere. The funny thing is that I was fully lubed up and so was she. She was also very relaxed, so I don’t see why I couldn’t get my dick inside her. My dick is about eight inches long and three inches thick, could this be the reason?

–Stranded in the Shower

It sounds like your girlfriend has never had anal sex before, and a nice warm shower does not qualify as warming her up! I am not surprised it felt impossible to get inside; the sphincter muscles are a tight ring of muscles and they’ll keep you from going anywhere you’re not welcome. In this case, you weren’t welcome because you tried to go from 0 to 60 in five seconds. So let’s start over and introduce her to this wonderful activity properly, shall we?

Begin exploring your girlfriend’s ass with analingus, external stimulation, and one finger. As you lick her pussy or stimulate her clit, slip a well-lubed finger inside her ass gently and slowly. Build from this experience and make sure to let her set the pace. Don’t proceed to add another finger or try out a toy until she’s ready.

Once you’ve had many sessions of anal penetration with fingers and toys, only then are you ready to put your dick in her ass. It sounds like your dick is both longer and a lot thicker than average. Get a dildo that’s just slightly smaller than your erect cock, and begin playing with it. Once she can take that dildo comfortably and it feels really good, then you can give your dick another try. If you return to the shower for the big event, make sure to use a silicone-based lubricant, since water-based lubes will simply wash away.

Oct 242012
 

My boyfriend and I have been dating for about two years, and he loves anal sex. Before him, I had never experienced anal anything. I really enjoy it, too. However there are times that no matter how bad I want to have anal sex and no matter how excited and ready for it I am, as soon as he enters me, the pain is so great, I can’t handle it. Other times, after the initial entry the pain subsides with pure pleasure and I can’t get enough.

I really would like to know why those times I can’t handle it are so painful and what I can do to lessen the pain. How can it hurt when I am so turned on and begging for it? I end up disappointing my boyfriend because I can’t handle the pain. This only happens about once out of every five times, but it is very aggravating for both of us. We don’t have anal sex all the time, usually about three to four times a month. We have tried using lots of lube. We have also tried Anal Ease — all that does is make his cock numb and he can’t keep an erection. Muscle relaxers don’t even seem to work. I am desperate for answers and help.

–Seeking Peace in Pennsylvania

Forget Anal Ease, it will make your ass and his cock numb, and that’s no fun for anyone. I also think muscle relaxants are not a good idea. There seems to be a mind/body disconnect going on for you, since it sounds like you feel extremely turned on, but your ass is not on the same page. Are you working your way up to it? Since you say that initial penetration hurts (even during those times when it eventually subsides), it seems like you’re not doing any warm up. If he just sticks his dick in your ass, no matter how well-lubed his cock is, it’s most likely going to hurt. Because our asses just don’t work that way. Your ass needs to be coaxed and seduced before a penis barges in.

Your boyfriend should start with his mouth, tongue, or one finger. When you’re ready, add another finger or move on to a small dildo or butt plug. He should not progress to the next step until whatever he’s doing feels really good and the penetration is comfortable. My hunch is that if you take things at a slower pace, you will give your ass a chance to catch up with the rest of you.

Oct 302011
 

The first time I tried anal sex was almost six years ago but it was EXTREMELY PAINFUL. I want to try anal again with my current partner. It gets me hot thinking about it with him, but when it comes to doing the actual deed, my butthole it closes up and nothing will get through. Seriously, it locks up tight — not even a finger will fit. I’m at a loss because I don’t know what to do to loosen up.

–Want to Get Loose

You and your ass were traumatized during that first negative experience, and you need to realize that it takes time to heal from any trauma. It sounds like you have a partner you trust and you’re enthusiastic and open about giving anal sex another shot, but your body hasn’t quite caught up to your mind.

I recommend that you very slowly begin to introduce anal play into your solo masturbation routine. Start with external rubbing or a vibrator on the outside only. When you are ready, really take it slowly. Try one finger or the slimmest toy you can find. Give yourself the time and space to explore anal play on your own, so it will take the pressure off doing it with your partner. When you feel comfortable, you can try it with your partner, but you need to take it just as slowly as you did on your own. Make an agreement with your partner that you’ll be the one to call the shots (or call it off if need be). Focus on your desire and trust to help you move past the fear and anxiety and toward pleasure.

Aug 152005
 

My wife and I are new to anal sex but we are both very interested and excited to try it. She enjoys penetration of small objects such as fingers and small plugs. But as we work up slowly to bigger things such as dildos and my cock, she complains of pain and sometimes burning. Also, I can’t get either of these things to go in her ass. She has no problem taking fingers or small plugs. She has one tight ass, let me tell you. We are using plenty of Astroglide, so I don’t think lube is the issue. She is ready and willing to try, but her body is not cooperating and it zaps the pleasure and fun out of it a lot of the time. Can you give us some advice on how to make things go easier without the pain?

–Backdoor Newbies

It sounds like you are taking many of the necessary steps for safe and pleasurable anal penetration, including going slowly, warming up with small things like fingers and toys, and using plenty of lube. As fans of Astroglide, I suggest you try Astroglide Gel, that brand’s thicker lube. Thick water-based lubes tend to stay wet longer and can act as a cushion inside the delicate rectum. The burning she experiences can be another form of pain (many people report the same feeling when they rush it or take something too big) or the body’s reaction to the lube. Try some different lubes to rule out the latter.

My suggestion is that you add some clitoral stimulation to the mix, which you did not mention in your letter. Whether you use your tongue, your hand, a vibrator, or she touches herself, clitoral stimulation can help transform anal penetration into a much more pleasurable experience. In fact, some women say they can’t have anything in their ass without clit stimulation. Remember, the more turned on she is, the more her body will relax, and she can let go. It’s also important for her to be one hundred percent into it. Ask her if she has lingering fears or doubts, since they can be getting in the way of her enjoyment. Her state of mind and body are both crucial to the experience, so make sure you take care of them both.

Aug 182004
 

Are some women’s butts more pre-disposed to anal intercourse than others? I know we are all different, with different bodies, needs, and desires, but I wonder if there is a physical component to achieving success in anal penetration. My current partner loves anal sex, and she can have these long, all-over-her-body orgasms when I fuck her that way. With my last girlfriend, however, I wanted on many occasions to have anal sex, but could never get it right. We did loads of foreplay, including massaging, oral with loads of clitoral stimulation, anal rimming, licking, loads of lube etc. With all that said and done, her butthole never loosened up very much, and didn’t get vaguely close to me getting myself in there. Is she just not an ‘A’ candidate, or was I missing something somewhere?

–Perplexed About A Butt

Yours is a very interesting question, one I think could be asked about all sorts of sexual desires and acts, not just anal penetration. You’re correct about how individual we all are; while our anatomy may be similar, our sexuality — how we liked to be touched, what turns us on, what combinations of sensations and scenarios brings us to orgasm — can be almost as unique as our fingerprints. Certainly, there are some women who seem to enjoy anal pleasure more than others, and I can say from experience that some women have an easier time than others. When I say easy, though, know that all the same rules still apply; you still must use lube, go slow, and make sure her body is warmed up. Likewise, there are plenty of women who tell me that they enjoy anal, but it takes them a lot of time to relax and open up, and on some occasions, it just won’t happen.

I appreciate your dedication to your previous girlfriend; it sounds like you made all the right moves, but even with the best effort, sometimes foreplay isn’t enough. In addition to the physical aspects of anal play, there are psychological and emotional components that cannot be ignored. If a woman is feeling unsure, nervous, anxious, or conflicted about receiving anal pleasure, then no amount of expert cunnilingus or rimming may change her mind. Sometimes, working through a partner’s fears about anal play — whether it’s the potential mess or pain, or feeling dirty for just wanting it — are the key to opening up. Free her mind, and (hopefully) her ass will follow.

Aug 202003
 

My boyfriend and I decided to try anal sex for the first time. We did it for about 5 or 10 minutes. He loved it. I, however, found it very uncomfortable and painful, and I didn’t have very much fun. Although at one point it almost felt good in a way. I want to try it again (he loves the idea so much), but I want to have fun while doing it. I’ve heard such good things about it. Is there anything we can do to make it more enjoyable for me or get me used to it without the pain?

–Clueless and Curious

First, I want to commend you on remaining curious and open to anal sex even after you had a not-so-memorable first experience. Most women have a negative anal de-flowering and never try it again.

It sounds to me like your husband may have made the most common mistake that I hear about: he rushed the process. Unlike your pussy, the ass is not self-lubricating, so you absolutely need to use lube, and plenty of it. I prefer a thick water-based lube that’s similar in consistency to hair gel; thicker lubricants stay wet longer and have a cushioning effect inside the delicate rectum. And speaking of the delicate rectum, your ass is very sensitive and needs plenty of slow, patient warm up to get it ready for your husband’s cock. That means activities like oral pleasure, gentle penetration with his finger or playing with a small butt plug or dildo to start. He needs to err on the side of caution, especially in the beginning, to get your ass used to having something inside it.

Take your time, and make sure you let him know if you want him to slow down or stop. As you relax (lots of deep breaths help), your ass will, too, and penetration should feel pleasurable, not painful. During this foreplay, experiment with adding other sensations to the mix: many women like (even need) clitoral stimulation in order for anal to feel good. Some like to have vaginal penetration or direct G-spot stimulation at the same time. See what works best for you.

Aug 142003
 

My partner likes anal sex very much, she has had plenty of experience and we practice it regularly. But, despite extended warm up sessions, a lot of lube and communication, she cannot accommodate my penis every time. I am always very gentle and caring. I know that even with the same partner each day is unique and different even if the mood and environment is the same. The situation is even more frustrating for me (and probably for her too) as we have often to stop after the tip of my cock has gotten inside her. It’s almost like some sort of reflex in her body just “rejects” me. What is the best way to achieve full anal sphincter relaxation, allowing an easy and guaranteed penis insertion?

–Patient in Paris

There are no guarantees in life, especially with matters of the heart and ass. It sounds to me like your partner’s body still isn’t relaxed enough which is why her ass is rejecting you. A surefire solution is to increase the amount of foreplay. I suggest more warm up with fingers and toys, plus you should add clitoral stimulation to the mix. Using a vibrator, your hand, or hers to manually stimulate her clit while you play with her ass can increase her arousal and help her rectum expand for penetration.

Once you first get inside her, don’t make any sudden moves. Stay put and give her a chance to adjust to the feeling before you start moving in and out. When she feels relaxed, then start with gentle thrusting, and let her call the shots in terms of speed and depth. Take your time, listen to her body, and don’t put so much pressure on yourself and her to make it happen every time.

Nov 262002
 

My boyfriend and I have been going out for 5 years. My boyfriend wants to have anal sex, but he is very big and thick. He hurts me when we’re just having regular sex. I don’t know why, since I’m 100% wet when we have sex, and it still hurts. We tried anal once but I told him to take it out because it hurt even when he put the head in. I’m just afraid that if we have anal sex he’s gonna hurt me. He says he will go slow, but he never listens to himself. Just before he’s getting ready to cum he starts to do it harder, so I don’t know if I should do it with him or not.

–I Want A Pain-Free Poke

First, I recommend you really focus on extended foreplay before your boyfriend even attempts penetration with his dick. Have him go down on you, rub your clit, use a vibrator, and work your body before getting inside it. The more aroused you get, the better your circulation; blood rushes to the genitals, the body relaxes, the pussy lubricates, and penetration becomes much easier. You say you are 100% wet, but I still really recommend using lube. Lube makes everything nice and slick, and eases penetration whether he’s well endowed or not. You also need to warm up both your ass and pussy with something smaller than your husband’s dick, like his fingers or a smaller dildo or vibrator. Start small and slow, and work your way up. Add another finger or go farther in only when you feel completely relaxed and ready for more. Don’t rush it.

Once you start having intercourse, make sure you are in the driver’s seat. You call the shots about how hard, how deep, how fast. Talk to your boyfriend and make sure he knows when something feels really good and when it does not. Penetration, whether vaginal or anal, should never hurt you. Take the time to make sure your body is warmed up, you are ready, and make sure he’s connected to you so he knows when the time is right.

For some men, in order to orgasm they need to take some very quick hard thrusts, which sounds like it may be the case with your guy. If he simply can’t slow down or when he does slow down, he can’t come, then I suggest this: when he’s ready to shoot, have him pull out. Then you can give him a hand job, he can jerk himself off, or he can thrust against you but not inside you.

Nov 072001
 


My girlfriend had recently asked me to have anal sex with her since we had never done it before. I complied, and after two tries (on separate occasions), we succeeded. We enjoyed it so much that we attempted it twice more with success. But we can’t do it anymore. We’ve tried, but we haven’t been able to do it for months. I am supportive as I can be. I give her control, soothe and relax her, question, encourage. But lately she says I have been hurting her. She says I get stuck just after my head goes in, and she can’t continue. The first time we went at it slowly, but near our climaxes, we started to really go at it, and she took all of it in. I have suggested some form of foreplay, but she refuses. She says it is all penis or nothing at all. Please help!

—Frustrated in Florida

You are absolutely doing the right thing by giving your girlfriend control and warming her up. Her insistence that it’s all or nothing just isn’t realistic, and you need to somehow make her see that. Remind her that the ass is not like the pussy: it requires a lot more delicate handling and more foreplay before she can relax it enough to make penetration comfortable and pleasurable. Licking her ass, penetrating with your fingers, or playing with a small butt plug, dildo, or vibrating toy are all good ways to get her ass ready for your cock; of course, remember to use plenty of lube! As for her theory that you are “getting stuck” after the head of your cock goes in, again, with a gradual progression to penetration, her ass will feel more relaxed and open. Because it is the head of your cock she complains about, it sounds like her sphincter muscles aren’t relaxed enough to accommodate your dick. With more warm up, she’ll be more aroused and it should feel much better.