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Past Tips


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

  • The basic 101's (by Alex Caroline Robboy, LCSW, CAS)
  • Anal Stimulation (by Alex Caroline Robboy, LCSW, CAS)
  • Harm? (by Alex Caroline Robboy, LCSW, CAS)
  • How to do the Venus Butterfly (written by the subscriber, Matthew B)
  • Anal Devices (Written by Shan&Claude)
  • Can't cum & anal sex (written by Dr. Pluhar)

HTHGS: The Basic 101’s of Anal Stimulation

*** Before putting any object into a person’s anus use common sense. And for those of you who are at a loss of what common anal sense is keeping reading.***

  •                   Listen to your partner.  This includes both verbal and non-verbal cues. What does she/he verbally say? Has she/he told you she/he wants to experiment with anal stimulation? Does she/he like having her/his butt touched. Does she/he get more excited  as your finger brushes along the tip of her/his anus?

  •      Never try something on a partner that you would be unwilling to have tried on you (unless specifically requested). 

  •      Always use retrievable objects. Can you imagine having to rush to the emergency room and explain to the on-call doctor that you have part of a cucumber stuck up your butt?

  •       Be clean. Wash all your tools with antibacterial soap and hot water before inserting them into your partner. You can also disinfect your toys by soaking it in hydrogen peroxide (full strength) for 15 minutes. 

  •      Always use smooth objects.  Anything sharp or jagged runs the risk of puncturing the anal canal. This not only causes pain, but may lead to infection and other complications.

  •      Avoid rigid objects. Flexible objects will enable you to maneuver through those curves in the rectum (and there are many of them!)

  •       And most importantly, be realistic. If this is the first time experimenting with anal stimulation start small. Your finger-tip is more than sufficient and will definitely create a rise. Fisting, and other such forms of anal-play are something that takes time to learn how to do / receive.  Trust & experience are something that only comes with time and practice. There is no such thing as an overnight expert.  No one is good the first time they have sex. Everybody is slightly uncoordinated and miss the social cues that teach us about a partner’s body.  Give yourself time. You have the rest of your life to perfect these techniques. Let yourself savor the moments of each ‘new’ thing that you try.

 This tip is written by Alex Caroline Robboy, LCSW, CAS

HTHGS: Anal Stimulation

Ask Alex 
My girlfriend & I are thinking of experimenting with anal sex. We have been discussing this for the past month, and believe it is about time that we give it a go. We are wondering if a condom is required. We are both monogamous and free of other sexually transmitted infections. The contraception that we are using is the pill. We have also heard that the initial penetration, the anal sphincter is likely to give a violent spasm. Is there anything that we can do to ease this? 

Dear Eager-to-Try, 
If both you & your partner are "free" of sexually transmitted infections and are monogamous, the need for a condom is minimal. Choosing to use a condom is a personal decision between you and your partner.

Pros of condom usage

  • Cleaner - some people feel bothered by the idea that when the penis (or finger) is withdrawn there is fecal waste on it.
  •  Safer - Even in a monogamous in relationship, each person is susceptible to infection with gonorrhea or HPV (warts) from a moist towel. Condom usage reduces the risk of sexual transmission.
  • Decreases the sensations slightly for the male, thus his erection may last longer.

To begin experimenting with anal pleasuring

  • Both partners must be willing.
  • Experiment with a finger, or an anal plug. This will help the insertee begin to get comfortable with this new sensation. At the beginning of anal pleasuring, take a deep breath and relax. The more relaxed the anal muscles are, the easier it is to insert a finger, penis or anal plug.
  • Lubrication will help the entry process and will reduce the risk of tearing the inside lining of the anus. Saliva and water based lubricants work well. According to Jack Morin, author of Anal Pleasure and Health oil is a recommended method. Having spoken with several sex educators, I have heard mixed opinions about this recommendation. Thus to be SAFE, I recommend using water based lubricants and/or saliva.
  • If something hurts, STOP.

HTHGS: Harm?
For all you women whose partner's want you to experiment with anal sex, it is only fair that if they want to stick their penis inside your anus, that they too be willing to experience something in their anus. Equality is the name of the game. If you are ready to engage in anal play, then that means you are willing to be on either end. You should be comfortable (or at least willing to try) putting something in your partner's anus, and having something inside your anus. To make this possible, I suggest keeping on hand a butt plug, small dildo/vibrator, finger and some Astroglide to help the ride. I know some of you may be reading this saying to yourselves, hey that's crazy. I do not have to be comfortable being on both ends to enjoy having something inserted into me, or inserting something into your partner. That is true, it is more an issue of flexibility. It is important in your own sexual development to be comfortable having done to you, what you do to others.

Some people have anal sex as a form of birth control. You can not get pregnant. Others have anal sex because they want to try something new. Experimenting can be fun. Some people choose to because it is so taboo. While others have anal sex for the simple reason, that it feels good. Anal pleasuring causes you to feel a sensation that is unlike anything else. There are no comparable sensations (but please feel free to write in descriptions which might be able to give others a better idea of what it could feel like). In fact, there is no one reason why people choose to incorporate anal sex into their sexual play. People choose to engage in anal sex due to desire, personal style, preference, and taste.

Tips written by Alex Caroline Robboy, LCSW


HTHGS: Anal Stimulation
Ask Alex,
Recently, I was feeling playful.  I didn't want to masturbate because I was pretty sure I would have sex with my wife when she got home.  I wanted to please myself in some way. I decided to get out a slim vibrator that we have.  I never used it in quite this way before though.  I lubed up well and inserted it with the idea of directly stimulating my prostate gland because I had read that this can be pleasing.  Wow, was I surprised.  I used the tip to massage my gland.  It felt so good I ended up getting pretty aggressive. My rectum became so relaxed that I wanted some thing larger and more powerful in there so I got out a larger vibrator and it went in fine.  None of this action gave me an erection, but it did give me minor ejaculations of what appeared to be thin semen.  It was not like having a regular orgasm. It was very new feeling and great.  After I decided to finally put things away and clean up, I was left with a really pleasant relaxed feeling in my abdomen that lasted into the next day.  I did have intercourse with my wife and it seemed better than usual and it seemed like I ejaculated more than I usually do even though I had already put out the fluid I did earlier.  This whole episode was really great and I want to experiment with it more but I am wondering if this could do me any long term harm in any way.  Is it OK as long as I don't feel any pain?  Is this type of ejaculation normal and is it regular semen that I was seeing? Confused,

 Dear Confused,
Yes, what you experienced was normal.  Furthermore, as long as you feel no pain, you can do no harm.  Enjoy!  

This tip was originally written by Alex Caroline Robboy, LCSW, CAS

HTHGS: How to do the Venus Butterfly (written by the subscriber, Matthew B)

The Venus Butterfly: here's another classic technique that's become legendary. It all started with an episode of the 80's TV series "L.A. Law." They referred hinted as to how it was actually done. That show generated more mail than any other episode. Everybody was asking, "How do you do The Venus Butterfly?" Now, you'll finally know.                                              

Here's What You Need:
**One bottle of baby oil.

Here's How You Do It:
Get your woman naked. Have her lie on her back, her knees bent and legs slightly apart. Apply a little baby oil to your hands.

Put your hands together, as if you were saying a prayer. Bend each of your ring fingers down. The tip of your left ring finger should be touching the knuckle of your right ring finger; the tip of your right ring finger should be touching the knuckle of your left ring finger. All of your other fingers should remain extended.

Now comes the "ladies choice" part of this technique. In the classic Venus Butterfly, your extended pinkies would be inserted into your woman's anus. Many women prefer that, instead, you simply fold your pinkies over like your ring fingers. It's totally a matter of personal preference.

Next, insert your middle fingers into her vagina. Your index fingers should be placed on both sides of your woman's clitoris.

Keeping your fingers together, open your palms so that your thumbs are about three inches apart. Begin to rub your fingers back and forth, as if you were trying to warm them. When you do this, your hands will resemble a butterfly flapping its wings.
Matthew B.


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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. 
     The purpose of this site is to share information. Thus, if you have any ideas, thoughts or information that you believe others might benefit from, please e-mail your tip to and I  will be sure to include it on either our weekly newsletter or here on the actual website. 

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