Anal Sex 101

Anal Sex 101


By Miss Tessa


That word – err, instruction – was supposed to be simple enough.

Instead, he pushed harder. Which completely embedded him inside me (oh, okay, my ass).  Complete with a loud grunt – he was happy, real happy, with the development, as his cock went all in, in my supposed satin-y ass (that’s what they say when they describe the feeling of buggery in stories, right?).

It was good for him, it seemed.

But it wasn’t exactly a great feeling for me.

Because it hurt.  Badly. Make that ‘really badly.’

And so there is a need to discuss anal sex.

There are many ways to name that act – e.g. anal sex/intercourse and pinuwet (stating the common), or bugger [an English term said to originate from an ancient Bulgarian tribe of people in the time of Peter I of Bulgaria (927-969), which, even if repressed (including killing them), remained strong until the fall of Bulgaria in the end of the 14th century. 

According to, “for the Bogomils, sex played a part in many social roles in their society, and male/male or male/female sex was normal (depending on the social activity: friendship, love, making babies, spiritual, sport).  Despite some rather advanced spiritual and intellectual beliefs, the Bogomills were negatively labeled for butt fucking, and since the English (profane) translation at the time for ‘Bogomills’ was ‘Buggery’, and that's what the act was eventually known as].

For the, “while there are many ways to enjoy the anus erotically – some people enjoy the sensation of a finger inserted into their anal opening and gently rotated, and others may find the insertion of a sex toy or penis very arousing and stimulating, some people are not very open to experimentation with this body part.”

The main reasons?  “They are scared that it will cause great amounts of pain, or the whole thought of it is grosses them out,” the site continues.

So now come the guidelines to ensure the anal sexual contact is fun for all concerned.

  1. Clean up. We’ve all heard the peanut butter or kangkong story linked with anal sex – yes, you get the point – so making sure it doesn’t happen to you is a must.  “Cleanliness is essential with virtually all forms of this type of play. A bath or a shower is a great primer, and can be the start of the festivities. Once your penis or sex toy has been inside the rectum, don't put them inside anywhere else until you have washed them. Carelessness in this regard can cause a very serious infection,” states
  2. Lube up, dear. Help it slide in smoothly.
  3. Don’t push it – unless, of course, it’s THAT small, or you’re into pain. The anus is like a vagina (no joke!), it has to get used to being penetrated.  From “Pain is usually a sign that something is being performed incorrectly, not that the act is wrong. In most cases pain is due to a few reasons: the receiver is too tense and tightening, the giver is pushing too hard, there isn’t enough lubricant, or that the penis or toy is still too big to put in (based on current experience levels). Using fingers and smaller toys is the best way to get used to the feeling, and it is advised that you increase size a little at a time. Once you have become comfortable with the idea and concepts you will probably find it very pleasurable.”
  4. Use condoms. The receiving end (you’re about the same as a glory hole, dearie) always has the higher risk to getting infected with STIs (HIV included), so take control of what gets into your body and from whom.
  5. Practice. Find what position is comfortable for you, angles of entry, et cetera.  After all, as the Sinclair Intimacy Institute ( states, “anal penetration can be pleasurable, but it can also be a source of physical discomfort. The muscle on the outside of the rectum, called the anal sphincter, ordinarily tightens if stimulated, which means that attempts at insertion of the penis, or even a finger, may be uncomfortable even if done slowly and gently. If penetration into the anus is forced, injury is possible. It is helpful to use a lubricant liberally and to relax and gradually dilate the sphincter by gentle manual stimulation before attempting penetration.”  Besides, you know what they say about practicing...
  6. Talk. He’s plugging your backside, not your mouth (unless there’s a third, fourth, fifth, et cetera party involved, and you are more than double plugged, of course), so tell him what’s in your head.
  1. No forcing.  “If your partner refuses, don’t try to force them, it will be a horrible experience for them (and ultimately for you) if they are not comfortable with the idea.
  2. If you’re THAT big, start slow – play with the finger or smaller toys before shoving yours in.  Unless the partner is into pain, of course.  As sexinfo101.comstates: “If you are trying to convince your partner to explore this world, using something as large as a penis is definitely not the way to get started. You should start by getting them comfortable being touched in the area, then move up to using a finger or two, and then, when ready, finally moving up to intercourse. Please refer to the anal fingering to please women, or prostate stimulation to please men sections to learn more about anal play, plus using anal sex toys and analingus. Until your partner is ready to receive, their anxieties will cause their anal sphincter to tighten, and trying to push through will be extremely painful, so be patient.”
  3. Stop when told to stop.  Unless you want shit wrapping your cock; or be kicked off the bed; or... Just stop – imagine if it’s you getting fucked, and the top won’t stop when you tell him/her to, then you get the point.
  4. Use condoms.  “Even if you're sure that both you and your partner are disease- free, you should still use a condom. The rectum is home to lots of infectious bacteria that can cause burning and urethritis of the penis. It will also help you clean up afterwards,” states the Sinclair Intimacy Institute.  Simply, yes, dear, even the top can get infections.
  5. Experiment, e.g. positions, angles, et cetera.  Make this good not just for you.
  6. Talk.  This will make it pleasurable for everyone.
Getting fucked (or, for that matter, fucking) in the ass is not for everyone.  Having stated this, do it ONLY when you are comfy with it – else, forget it, there are still a lot of other holes to be plugged. Unless you're into pain, no forcing is necessary.

As for my hard plugging BF?  He’s an “ex” now.  No use staying with someone who thinks a “go slow” means “faster”, or thinks that a “no” is really a “yes”.  There, too, are still a lot of other guys to be had.


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