From top to rocking bottom


Steven Lavender 

This article is written to help men who have been a top and now want to, or at least, are thinking of transitioning to being a bottom and do not know precisely how to go about it.  Some men will have physical and or psychological issues achieving this, and some will not have any problems at all.  If you have attempted anal sex and the attempt failed because it hurt of your head was in the wrong space, or you have never tried and don’t know where to start, read on. 

Get help if you need it

Life is very short.  Try not to waste time entertaining unhelpful and self-limiting thoughts and behaviors that will rob you of potentially new and beautiful experiences.  If you find yourself unable to proceed with achieving your goals because of emotional, intellectual, negative self-talk, or self-esteem issues, please seek help from an experienced recommended health professional.  If you are unsure if your anal and rectal tissue is in excellent condition because of the possible side effects of some treatments, get it checked by a medical doctor before you entertain the idea of putting anything in your ass.

Location, location, location

For those of you who don’t know the anus is located in a group of muscles called the pelvic floor. The pelvic floor muscles lay like a sling between your pelvic bone and your tail bone.  If you are sitting upright reading this article, your pelvic floor will be in contact with the surface of the seat.  It has several vital functions.  Firstly the pelvic floor supports all of the organs above it.  It is an essential part of and contributes to what we now understand as core stability.  It regulates the passage of urine and feces from the body.  Specific muscles of the pelvic floor are responsible for filling the penis with blood to form an erection and pulse in orgasm to propel semen from the body.  Some of the muscles are under your conscious control, and some are not. 

Everyone gets this bit wrong

The anus is two muscles that form the terminal tube of the intestinal tract. It is a common misbelieve that the anal verge is called the external sphincter and the other end of the anal canal called the internal sphincter.  There is an internal and external anal sphincter but, the external anal sphincter raps around the internal sphincter and they both run the course of the anal canal which is 3-5 centimeters long.  You have conscious control over the external sphincter. The power you have over the external sphincter is demonstrated by your ability to squeeze the muscle when you want to put off passing gas or going to the bathroom when it is inconvenient. There is another muscle that when tightened can feel like there is a deep internal sphincter.  It is called the puborectalis muscle.  It originates behind the pubic bone and loops around the descending bowel. When tightened it causes a kink in the tube which also helps regulate the passage of stool from the bowel.  Getting through the anal canal is the hard part of receptive anal sex.  Once your finger, anal toy or partner’s penis is past the anal canal, the pressure is off as you have just entered the rectum.


Tension equals increased muscle tone which leads to pain which leads to increased tension which leads to….

Because the pelvic floor has work to do, even at rest it has a certain amount of muscle tone. This is called resting tone.  This pelvic floor resting tone keeps the anus closed thereby containing gas, liquid or solid fecal matter inside the body until you decide to empty it.  The muscle tone increases and decreases so the pelvic floor can continue to do its job under different circumstances. Resting tone can become unnecessarily elevated due to factors including stress, anxiety, anger, pain and so on.  This increased resting tone can cause pain, unsatisfactory bowel movements, resistance to receptive anal sex and can increase the risk of injury associated with anal sex or passing a hard stool.

To prepare yourself to experiment with receptive anal sex the tone of your pelvic floor should be at its most relaxed.  Anything that hinders this relaxed tone should be dealt with before proceeding. This includes stress, anxiety, fear, a bad mood or being physically uncomfortable.  

Preparation for anal sex is preparation for girth not the length in most cases

Breath deeply rhythmically and constantly

Relaxation is by definition the active inhibition of normal resting tone.  This feeling is like the feeling you are seeking during meditation.  It is the feeling you get after the first or second sip of a great Marguerita or the whole body feeling just before drifting off to a peaceful sleep.  There should be a sense of heaviness to a muscle in a genuinely relaxed state.  To first start engaging in anal sex you want to obtain the feeling a deep heavy relaxation in your pelvic floor.  When you are learning relaxation, it might be easiest to learn whole body relaxation.  Then with time and experience, you can begin to isolate your pelvic floor and experiment with the ability to relax just those muscles.  The feeling of truly relaxed pelvic floor muscles would be the same feeling you have after emptying your bowls without stress or strain.  It is almost impossible to increase unwanted muscle tension when you practice deep abdominal breathing.  The reverse is also true; it is easy to increase unwanted muscle tension by shallow chest breathing.

Getting to know your asshole inside and out

To prepare yourself for bottoming there are a couple of things you can do so when the big day comes you will be a pro.  This is the time that you have to get to know and understand your anus.  To the uninitiated, it can feel like your ass has a mind of its own.  You need to know it and understand it so you can control it.  This is vital because if you do not know it and understand it, you could get injured by doing too much too soon.  If you have never had anything near your anus get your self in a comfortable position where you can still reach your ass with an index finger.  This comfortable position will be different for everyone.  Some people can reach their ass lying down on their back.  Others may find it easier to sit on the toilet or sit on their haunches and reach behind yourself as if wiping yourself with toilet paper.  Put the pad of your well-lubed index finger directly on the outside of your external anal verge and start small circular motions.  Breath deeply and regularly and try to relax the muscle actively.  No matter how relaxed you are, you will occasionally feel a reflex tightening or grip of your sphincter around your finger.  When this occurs stop and wait, do not pull out, wait ‘till the grip relaxes entirely and start again.  After a short amount of time, you will probably find the anal verge has relaxed, and the pad of your finger is now considerably deeper than where you began and resistance to your finger much less.  Do this until you get used to it and you get to understand the feelings, sensations, and reactivity of the anal muscle.  This is your time to get acquainted with your ass.  Do not skip this step if you are a beginner. Keep performing this activity until you feel like you can proceed.  Remember the first entry will always need some coaxing no matter how skilled you become.

Resistance is futile

 At first, your finger may be too big and make you too uncomfortable to continue inserting it deeper into the anus.  If this happens, you will benefit from a graded set of beginner butt plugs. They come in boxes of three or four.  You can purchase them online.  Of course, you start with the smallest one with plenty of lube on it.  The goal is not to get it in all the way immediately.  The goal is to learn as you go so the experience is positive and you don’t get hurt. Gently let you ass accommodate to the size and pressure.  Gently push the plug in until you feel some resistance but not pain, stay at that point for a moment, wait and feel and learn what that, and every sensation means.  Gently pull the plug out a short distance and gently push it back in.  Repeat again and again until you can get the plug in further and further. Listen and feel.  When you can move the small plug in and out without pain or trauma, move onto the next size and do the same thing. As you learn more and your ass accommodates to the increasing sizes try doing this in different positions.  If you have been doing this lying on your back, try doing it sitting on your haunches or child’s pose.

Down and out and in and up

When you can change positions with the plug inside you and still be comfortable try some muscle control exercises.  These exercises will significantly enhance both your partners and your sexual enjoyment.  Start by using only the internal pelvic muscles and gently push down and out with the plug still inside you, like you are trying to have a bowel movement or push the plug out. Then try pulling in and up like you are trying to stop having a bowel movement or passing gas with the plug inside you.  This is the beginning of learning control over the muscles. This is learning time.  When you are just starting, don’t use the dilation plugs every day. Give the anal canal tissue and muscles some time to relax and repair.  Start with every second or third day.  Only use anal toys that have a large solid base at the end of them as many a couple has ended up in the ER after a toy has gone rogue.

Don’t do anything that causes pain

I am having a great deal of success in my practice with a protocol for anal self dilation using just a finger.  I use this protocol with people who have elevated resting anal tone or soft tissue restrictions causing difficulty in achieving receptive anal sex.  This particular research was designed to compare and contrast anal dilation treatment following the diagnosis of an anal fissure. I think it works so well because it provides a closed loop of sensory input, (head, finger, ass, head finger, etc), as opposed to an open chain using inanimate dilation dildos or plugs.  The protocol comes from a research article titled,  Anal self-massage in the treatment of acute anal fissure: a randomized prospective study Fabio Gaj, a Ivano Biviano,b Laura Candeloro,b, and Jacopo Andreuccettic.  , published in Ann Gastroenterol. 2017; 30(4): 438–441.

Published online 2017 May 10. Doi: 10.20524/aog.2017.0154   The protocol calls for a seven-day commitment.  For the first two days, the participant places a well-lubed index finger into the anus and just stay still twice a day for ten minutes.  This, of course, is doing more than what it would first appear.  As I have tried to make clear previously in this article, understanding your anus, and it’s “personality,” if you will, takes time and concentration in the beginning.  For the remaining five days the participant, with the inserted lubed finger, gently performs a circular motion with a slowly increasing diameter.  Only to comfort.  The results of this technique, in the treatment of hypertonic anal sphincter causing anal fissure, were found to be faster and cost less than using dilators.  Do yourself a favor and do both the plugs and the finger.  Do the plugs a couple of times a week with time in between to rest and repair.  When you are up to the large plug start the fingering on the off plug days.  Gently.


So now it is time for real sex


So after all of this preparation, you should have learned a great deal about yourself and your ass.  The reason for all of this preparation is to achieve your goals while avoiding injury.  By now you should be able to breathe deeply and continuously, relax the muscles of your pelvic floor in a variety of positions, accept a finger and the largest of the dilators completely without apprehension or pain and exhibit some level of control over the muscles of your pelvic floor.  Right?

Give yourself the best chance of success when the time comes.   If you are nervous and think you may poo with all the stimulation then give yourself a Fleet Enema.  Buy it at the pharmacy, follow the directions; it is quick and painless. Don’t overdo it thinking more is better.  It isn’t in this case.  If you think about it,  the time that your pelvic floor is used to being relaxed and staying relaxed in on the toilet after you have moved your bowels.  So until you are as confident as you can be, simulate that position for the first penetration. 

Positioned for success

Do not choose a partner that has a larger penis than your largest plug for the first time.   Look at the circumference of your largest plug and compare.   You need some “wiggle room” to be comfortable and safe.  Always try to have a partner who is smaller than the maximum girth you can take.  To enjoy sex, you want to be able to be transported and let go.  If you are at you limit immediately, then any quick misdirected thrust may be the one that finishes the evening abruptly and painfully. So with that in mind proceed.  With your partner lying on his back, straddle him, so you end up facing his feet.  This is also known as the Reverse Cowboy.  Keep your spine tall and long, hinge forward at your hips just a little ( 15-30 degrees) like a dipping bird, then ever so slightly push your ass out a little by just arching your lower back gently.  This position mimics the position you should be when going to the toilet.  Your bowel should be used to being relaxed in this toileting-like position.  The backward tilt of your pelvis will help position the puborectalis muscle, (the muscle that can feel like a false internal sphincter), away from the incoming penis.  Reach behind yourself and position the penis at your anal verge, continue deep relaxed abdominal breathing, relax your pelvic floor to heavy and gently sit down on him ‘till you feel some resistance.  Stay calm, keep breathing and actively relaxing your pelvic floor and wait.  Wait ‘till the resistance eases ultimately and gently continue.  Keep your back up, the forward lean and the backward pelvic tilt in place.  Even when you get more experience with receptive anal sex, you may still choose to initiate sex in this position as it facilitates and open relaxed pelvic floor you being in control.


So what could possibly go wrong

It is not abnormal to see a small about of blood after ass play.  A diffuse amount of pale pink fluid on tissue paper at clean up after sex and no pain is not an emergency.  You may experience this a couple of times when beginning and the symptoms will usually cease.  A bright red streak of blood on a toy or your partner’s penis with the feeling of an acute paper cut in your bum is a sign you have torn the lining of your ass.  You may feel acute pain or sting with a bowel movement following the event.  This does not constitute an emergency either.  Rest your backside for a couple of days and avoid hard stool or any anal play.   If symptoms persist more than a couple of days see your doctor.

Again is it outside the scope of this paper to discuss all of the possible consequences of having sex in the modern era.  Take time to educate yourself about risk, disease, and precautions.

If you are still nervous and unsure, seek help from a pelvic floor physio, proctologist or gastroenterologist.  There are gay or anally driven straight men friendly medics in most cities that will make you feel comfortable and help you with your concerns.

Things to remember

1) Learn to relax yourself and your anus

2) Get to know your anus and use graded toys and your finger to help

3) go slowly and do your homework before you jump right in

4) The reverse cowboy can be a man’s best friend

5) At first, don’t let your eyes be bigger than your anus. Leave some wiggle room