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Anal Sex   
Brought to you by How To Have Good Sex Inc

How to engage in anal sex (written by Alex Caroline Robboy, LSW)

Ask Alex,
I am a heterosexual girl, and my partner and I have experimented a little with anal sex.  At first, he was interested in it, but when he saw how I wasn't interested and how I winced and stopped all sex when he tried to penetrate me because of the pain he lost interest.  The strange thing is that I've now become really interested in this, even though I know there is a LOT of discomfort involved.  When I approached him with the idea of having anal sex, he was really hesitant, saying that he knew it would hurt me and then after agreeing, I winced as he started inserting his penis into me and then he insisted that we stop. Since he pulled out of me and I didn't want to go through the initial pain of insertion I eagerly complied.  I have two questions, one how can I get him interested in anal sex again, and how can I limit how much it hurts-we used plenty of lube, but he does have a very large penis.    Interested in Anal Sex,

 Dear Interested in Anal Sex,
I am glad you wrote. There are many things you can do to help the situation.  The first issue that you must tackle is how to let your partner know that despite the potential for pain, you are interested in experimenting with anal play.  To do so, here are some possible tactics.  You could try the verbal approach: tell him that despite the fact that you may experience a little bit of discomfort, you want to try anal sex.  If he is worried that he is hurting you, tell him that you will take care of yourself and he should worry about his own pleasure. If the pain gets too severe, you will say the code word, ‘coffee mug’ to signal that you need to stop. But most likely, you may just say, slow down or lets just stop for a moment while you adjust to the sensations, but that you do not mean ‘STOP.’    Second you could try the behavioral approach: show him your interest (e.g. – let your body do the talking).  Let him see how physically excited you are by the idea.  Moan, grown, talk dirty to him.  Right now, he doesn’t trust your body language and he may need some time to adjust to the idea that something that could cause some discomfort could actually also be a turn on.  In addition, you could arrange on a Friday night to watch some sexy movies together about couples having anal sex. As you watch the movie, you could tell him how much the sight excites you. Lastly, you could purchase some books on ‘how to engage in anal sex’ and leave them on his coffee table with a note attached saying that you saw this and thought of him.   

To grapple with the pain that you mentioned, there are several techniques to decrease the pain.  The most important thing you can do is to relax your sphincter muscles.  Tight sphincter muscles can cause pain.  To relax your sphincter muscles try squeezing them ten times fast, and then feel what they feel like afterwards. Next try simply focusing on relaxing them. Sometimes, taking several deep breaths help. Another way to do the same thing is by getting used to the sessions caused by having your anus stimulated.  To do so, start small. Maybe have your partner use his finger inside of you.  Hint, lots of lubrication helps. Some women love anal stimulation combined with oral sex / manual stimulation. 

Fun ways to use your finger during anal play:

  •  While the woman is lying down, the man should be down towards her feet, looking up at her vagina.  He then should insert his index finger into her anus and make the ‘come here motion.’  To facilitate the ease of penetration, place a lot of water-based-lubricant at the tip of your finger.

  •  Using the same position as before, the man can take his well – lubricated finger and enter her anus while making very small circles. 

  • Experiment with different finger positions. After each slight (note the word SLIGHT) variation ask your partner if she liked “choice A” or “choice B” better.  Whichever she prefers repeat, and then add in some new variable.


Alex Caroline Robboy LSW



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The Founder: "Alex" Caroline Robboy, LCSW, QSW, CAS
"Alex" Caroline Robboy is a certified sex therapist through the American Association of Sex Educators, Counselors and Therapists and an American Board Certified Sexologist. In addition, she is a clinical member of the American Association of Marriage and Family Therapists and a member of the North American Society for Psychological Obstetrics and Gynecology.


  Our Philosophy sex is like dancing, it changes every time. It depends on culture, atmosphere and mood. Sometimes it is done alone, with a partner or in a group. It can be fast and hard or slow and soft. Sex is a combination of non-verbal negotiation and verbal cues: a scream, a twitch of the toes, or a flush of the face. There is no one 'right' way to move, only what feels good to all those involved. 
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