How to Enjoy Anal Sex

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One woman's suggestions.
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Judging from the popularity of this category and the myriad of responses I received from the two stories I have in this category, I have come to the conclusion that the misconceptions and preconceived notions respecting anal sex are legendary. My impression is for the most part that a lot of men want it and a lot of women are horrified at the very thought. Generally, society has frowned on this type of sex, as reflected in derogatory remarks such as "asshole". Unfortunately, a lot of people are missing out on a great addition to their sexual repertoire.

Before I go any further, I want to VERY clearly urge anyone with ANY concerns about their health to USE a condom. Even the gentlest anal sex can cause tiny nicks and scratches that could easily conduct any organisms straight into your body.

The anus has a multitude of nerves and muscles which when stimulated correctly, can provide enormous pleasure. Two sphincters are obvious when a finger is inserted – the first which provides the 'pucker" with which everyone is familiar, the other, about half an inch in. The first is controlled by the individual consciously – thus you can tighten or loosen it at will. The second is controlled by the part of the brain that controls bodily functions such as heartbeat, breathing etc – i.e. you cannot control its reactions directly. Proper and gentle manipulation can be equally enjoyable for men – whose prostrate can be stimulated from the insertion of a finger in the rectum – and for women, whose G spot is readily massaged through this form of lovemaking.

I would highly recommend that each individual familiarize themselves with their own bodies, exploring their own fundaments first to gauge the feeling and reactions that the insertion of a finger or object engenders.

As an aficionado myself, and female, I thought it would be helpful to address the issue and give my own suggestions/recommendations respecting the introduction and enjoyment of this unique form of lovemaking. I will deal with male penetration of a female's rectum as that is what I can recommend and am familiar with.

Anal sex is not something that should be introduced on a whim, nor thrust upon someone who is unfamiliar with this very arousing form of lovemaking. Ultimately, I believe that preparation and patience are the two primary ingredients of a successful introduction to anal sex.

A subtle yet honest form of behaviour modification works very well in this regard. Introducing your lover by attempting to push a stiff penis up a very small area unused to intrusions from that side of the body is a guarantee of failure. Rather, start gently and carefully.

1. First, begin with oral sex – an excellent starting point as you not only have intimate access to the desired area but as your lover's arousal increases, you are provided with the opportunity to gently and subtly introduce a finger; for instance, just tickling the fundament as your tongue takes care to keep her attention focused on the main event. As your lover starts to peak, push your finger very gently within the rim – do not go too deep or you will not only most likely derail her orgasm (thus creating a very frustrated and angry lover), you will also overstep the first steps to successful seduction.

Do this frequently and often, allowing her to slowly get accustomed to the feel of something tickling her anus, and in turn, linking an orgasm with the sensation of a foreign object around her anus. Done correctly, she will unconsciously begin to enjoy the extra stimulation provided by a careful finger or a warm tongue.

My strongest advice – DO NOT rush it! Most of us have been taught from a young age that anything to do with the very natural functions conversant with an anus are "dirty", that anything to do with the butt is "hands off". So not only do most people have to deal with the startling reality of accustoming themselves to something foreign in their anus – even more importantly, they have to overcome societal imperatives and parental restrictions.

2. Second, after your lover has become accustomed to – and learned to enjoy – non-threatening anal play, slowly begin to increase the level of your insertion. The anus does not self-lubricate, so unless your finger is sufficiently lubricated with your partner's own juices, then use a proper lubricant such as KY jelly or something similar. Providing oral sex while gently thrusting your finger in and out of her anus after she has learned to enjoy anal play is guaranteed to provide a very satisfactory and intense orgasm – thus continuing your gentle behaviour modification.

At this stage, it can also be stimulating and encouraging to gently insert a finger during intercourse. This can be done in a variety of positions, the easiest being the female kneeling and the male penetrating from the back. He then has easy access to her rectum and although it can be tricky, the sensation engendered by double penetration can be seductive and immensely exciting.

3. Third. After a sufficient period of time has elapsed and your lover has become accustomed to and enjoys her anus being stimulated, then you can begin preparations for actual anal intercourse.

There are some basic rules and preparation that I would highly recommend if you want an enjoyable and satisfying experience with anal sex. I will list them below:

• Be healthy – ensure there is plenty of fibre in your diet so that your natural functions are normal and healthy. Some individuals prefer to have an enema to ensure no fecal matter is present, but if your diet is healthy and you have emptied your bowels, I do not believe this is necessary.

• Have a recommended lubricant on hand, such as KY jelly.

• Be conscious at all times of your lover's responses – being aware and responsive to her reactions is crucial if both parties are to enjoy the process.

4. Next, it is probably most helpful to introduce anal sex when your lover is already open, relaxed and aroused – i.e. don't START with it but consider it the culmination of a sexy, fun and enthusiastic session of lovemaking. This is also advised because due to matters of hygiene and possible cross-contamination, it is highly recommended than the penis is washed thoroughly and carefully with soap and water after anal sex. The penis must be washed both to avoid any bacteria that might cause infection in the penis, but also to avoid giving your lover any issues.

Thus, assuming that you are now ready to introduce the penis, I suggest the following:

1. Lots of lubrication – particularly the first few times – play with your partner's anus with lubricated fingers and warm tongue until the rectum is relaxed and open. You can lubricate her rectum during play. Then, ensure that your penis is similarly coated with a safe lubricant.

2. Choosing a position which is comfortable for both of you – spoon fashion works very well especially for the first few times as it gives the woman more control – holding your penis firmly, push it gently – and I mean gently, against the lubricated rectum. A lubricated anus together with a lubricated penis almost guarantees that the spongy head of the penis will slowly push in. JUST as you enter – STOP!

It should be noted at this point, that the two sphincter muscles I mentioned above now become relevant. The woman can help with the first muscle by pushing out as if having a bowel movement - that flares the anus open and gives egress to the penis. BUT, once the head of the penis has entered, the man must stop and allow the inner sphincter muscles to accommodate themselves to the intrusion. However, eager and open she is, the woman cannot control that inner muscle and must wait for her body to accommodate – forcing it at this point could damage and tear the muscles.

3. Let the woman take the initiative at this point. She has to accustom herself to the feel of the penis in her butt – the sensation when first experienced can feel quite uncomfortable, as if you need to have a bowel movement. Allow her the time to relax both physically (given time, the inner ring of muscles will loosen) and emotionally, to the feel of a penis in her rectum. Allow her to take the lead, to indicate either verbally or through her body that she is ready for you to push a little more of your penis up. Again, GO SLOW. As the penis is thrust up the fundament, that ring of muscles will once again tighten; allow them the time to loosen and relax as they accommodate the girth of the penis.

Once the entire penis is inserted to the groin, relax and enjoy the sensation before actually beginning to thrust. The woman can flex and constrict the outer ring of muscles as she becomes used to the feel. By slowing wiggling her bottom, she can control the rhythm and make the decision when she wants her partner to push in or out.

4. The feel of a penis up your rectum is immensely arousing once you have been properly prepared. There is the physical reality that the anus has a multitude of nerve endings and muscles that signal pleasure, the feel of a thrusting penis against the G spot can induce a sensation unlike any other (and can actually eventually lead to female ejaculation which will be the subject of another essay) and then the emotional reality that you are engaging in a "forbidden" pleasure can be in itself stimulating and exciting.

From that point on, keeping hyper aware of your partner's response, you can engage in an increasingly enthusiastic bout of anal intercourse. As the intercourse continues, while the anus itself doesn't self lubricate, the sensation and intense pleasure will ensure that the woman's natural lubrication together with the male's pre-cum mingle to form a very satisfactory and slippery lubricant which adds to the pleasure and allows intercourse to become more enthusiastic.

The man at this point, may want to reach around and stimulate the woman's clitoris manually as it is quite common for women to require a little extra stimulation.

The only drawback to anal sex at this point occurs when the very exciting session has culminated and both partners have orgasmed. While it is tempting to loll in bed and enjoy the aftermath, it is crucial to wash within a reasonably quick period after sex – both the male and the female – to avoid the possibility of any infections.

I would add at this point that once you and your partner have a little more experience, some may prefer to use less lubricant or dispense with it altogether. Many females such as myself prefer the rougher stimulus provided by an unlubricated penis.

All in all, anal sex can be an exciting, arousing and fun addition to lovemaking.

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Client8Client8over 2 years ago

In criticism of every "how to" I've read here on LitEro: nobody's going to gain anything from anyone telling you how you should go about anything about sex. LISTEN to your partner. TALK to your partner. That's the ONLY way to go.

AnonymousAnonymousover 4 years ago
Extremely useful

A great practical guide

Shenachie2010Shenachie2010almost 7 years ago
KY Jelly?

Here in the UK it s a thin water based jelly not suitable in my opinion and experience for anal. For enabling a medics finger for a brief inspection yes fine. But not for full on anal.

Please buy a proper anal lube such as "Backdoor" which is excellent.

AnonymousAnonymousabout 7 years ago
"Do guys like anal?. . ."

To answer that question, anal sex with my wife is the most mind-blowing sex either of us has. There is no feeling like her clamping down on my cock while I'm in there!

AnonymousAnonymousabout 11 years ago
whoop!

as a young gay man, this was really good advice

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