Ask Cara: Women’s beginner’s guide to giving a man anal pleasure (& helpful top tips)

Question

I’ve started a new relationship with a man and it turns out he wants me to give him anal pleasure. I’ve only ever been with one guy before who liked it and it was a very short relationship so we didn’t dabble that much. I know things like keeping my nails short and using lube but after that I am pretty clueless! I know how I like my ass played with but that’s me, and I’m a woman – I have no idea what I am doing with a man. Could you possibly explain how to give anal pleasure to a man, or some kind of beginner’s guide? Some helpful top tips would be really awesome! Hoping you can help.

– Anon

Answer

Hi there and thanks for your question. Anal play is a sensitive subject (pun entirely intended) for all parties involved. As you may be aware, the tissue and lining inside the anal area is quite thin and prone to tears and rips if not treated with the utmost respect.

 

  1. Always use lube. I cannot emphasise this enough. Lubricant is mandatory for anal play. I don’t mean a quick spit on your fingertips before shoving them in with a whispered prayer either; I’m talking about honest-to-goodnesssex lube. You can choose from water based or silicone, there are even thicker formulation lubricants available especially for anal sex and use with anal sex toys. They’re less likely to run too fast and dribble into a messy puddle beneath. You can also make sure it stays where intended and feel where it’s going – no matter what the lighting in the room is like.
  2. Work slowly. Rushing when it comes to anal pleasure does nobody any good – at least not until there’s a decent about of lubrication, little to zero friction and everyone’s passionate in the heat of the moment. This is especially true for newbies to anal play. Things in the bottom seem larger than they appear so start very small, smaller than you’d think. Edge the tip of a pinky finger inside to begin with, aided by lubricant (I may have mentioned lube already).
  3. In a similar vein, if you want to introduce anal sex toys to him then start off very small. There are various butt plugs for beginners and a static one first of all (as opposed to a vibrating butt plug) may be less intimidating and help him get used to the shape and feel inside him. Only use sex toys with a flared base for anal play as this will stop them from being ‘sucked up’ into the body. Other ideal anal beginner toys are multi butt plug sets which let you experiment with different sizes, as well as inflatable options which give you the versatility of a small or large butt plug and everywhere in between – as well as a quick release valve in case of panic.
  4. Give additional pleasure while experimenting with his anal region. This is quite tricky, as it’s natural to want to see what you’re doing. Extra and familiar pleasure helps him relax and allows you to explore his ass with your fingers if you’re giving him a fluid, well lubricated hand job at the same time, paying attention to his testicles as well as his shaft and penis tip, of course. In later sessions you might feel confident enough to kiss and suck his penis, giving a languid and thoroughly stimulating blow job while you probe his anal area slowly.
  5. When giving anal pleasure to a man, you would do well to be aware of a little something called the prostate. A little walnut shaped something, to be precise. This gland is located fairly deep inside the anal canal, on the upper wall if the man is laying face up. You should be able to just about stimulate it with a fingertip or two but it takes practice – and again, more lube. Use a beckoning motion with your finger and watch him squirm in pleasure. You’re right to keep your fingernails short! The prostate is the epicentre of a man’s anal pleasure. When correctly stimulated, the prostate can lead to full body orgasms like your man has never before experienced. For more on this subject and a great deal of in-depth, expert knowledge, I highly recommend Charlie Glickman’s The Ultimate Guide to Prostate Pleasure (here at Amazon.com:https://www.amazon.com/gp/product/1573449040/ref=as_li_tl?ie=UTF8&camp=1789&creative=390957&creativeASIN=1573449040&linkCode=as2&tag=carsut-20&linkId=IYPA6HZHSU3LTH3N). It’s a must-read for everything prostate and male anal  pleasure.
  6. A little housekeeping: don’t use sex toys from anal to vaginal (woman) or share sex toys between his anus and your anus and/or vagina. The anal area is loaded with bacteria which can cause nasty irritations, infections and other medical issues of a nasty nature if you introduce them to other areas on yourself or on another person. After anal play, always make sure you wash all items involved (sex toys, fingers, body parts) thoroughly and use an anti-bacterial soap (or relevant spray, in the case of sex toys). Use a nail brush to make sure you remove any nasties from under your nails.

I hope that this short guide to giving a man anal pleasure has helped – good luck and enjoy your anal adventures together.

Enjoying anal sex is definitely a pleasure that takes a bit of a learning curve. Listening to your body and communication with your lover are a must. Also, I can’t stress enough how important going slowly, relaxing and using lots of lube are to your fun. Another key to enjoying anal sex is the position you play in.

For the beginner, there are several positions that are easier for penetration and can also make things funner all around.

Missionary – The original man on top position for PIV sex. With her bottom tilted upward, her little hole is exposed and easy for him to access. With her legs folded back towards the shoulders, this is a great position for those who like deep penetration or if he has a shorter penis.

You can also try these variations of the traditional Missionary position.

Upright Missionary – With her on the back, he sits up on his knees between her legs. She bends her knees and rest her feet on his chest. In this position, his hands are free to explore her lady bits or breasts. It’s also fun for men who like a good view.

Missionary L – In the same manner as the Upright Missionary, in this position, her legs are straight in this position rather than resting on his chest. Lying in this position her torso and rectum straightens out, making penetration a bit easier. This position is also good for those who like shallow penetration since he can control the depth easily.

CowGirl – the typical woman on top for PIV sex. With her straddling him, this is a good position for beginners because she can control the angle, depth and pace. While she controls it all, his hands are free to explore and give her extra stimulation. This is also a good position to prolog your play, since a man’s ejaculation reflexes slow down when he’s on his back.

Froggie – A fun variation of Cowgirl, in the position she’s crouched down on her feet straddling him. Taking the strain off her knees she can now ride his rod more vigorously. I’ve found that this position works a bit easier when I can reach the headboard or wall to balance against.

Spooning – Especially comfortable for anal beginners, with both partners on their sides facing in the same direction, penetration is natural and easy. Also, lying in this position, thrusting is gentler and slower. With lots of body contact, this position lets your hands be free to explore and caress each other. It’s also a great position for those who like to use a vibrator while they play since there’s full access to her vulva.

As Spooning becomes comfortable and she wants more, it’s easy to move into the Spoon & Fork position. With one of his leg between hers, wrap yourselves together. He’ll find that thrusting with gusto is much easier in this position.

Doggie Style – Oh yes the beloved Doggie Style is a great position for anal sex beginners. With her on all fours, this position is extremely versatile. Since she can angle herself differently, finding the right variation for smooth penetration is easy. After she’s warmed up, Doggie Style lets him thrust deep and hard. At the same time, in this position she can take control and slowly move herself on his rod. Men love this position because it’s easy to see and his hands are free to explore her ass.

Remember, there’s never a right or wrong way to a sexual position. All positions can be adapted to accommodate your needs, body size, flexibility, comfort, personal preferences, gender or sexual orientation. Sexual positions aren’t about finding the correct way. It’s about exploring with your partner and finding what’s right for you. The joy is in the journey, not in the perfection.

For me, anal sex is a great experience. Explore and find the pleasures that it may hold for you too.

Wiki-anal oral sex google imageIf you’re apprehensive about anal sex; you’re not alone. Thousands of women are nervous about trying it. Even more have vowed to never try it again after a bad experience.

Often times, anal sex is thought of as dirty, painful or awkward at the best. But it doesn’t have to be this way. Anal sex can be a highly erotic sexual pleasure with the right approach.

Hygiene

Hygiene is a simple fix. If you have normal firmed bowel movements simply washing with close attention to your bottom should do the trick. For a better cleaning anal douching is an effective choice; visit my article for more about anal douching. Another option is having your partner wear a condom during anal sex. With a condom, clean up is easy in case of an accident.

Warming Up

The number one thing to help you get in the mood for anal sex is warming up your bottom. A sensual booty massage is a great way to help get your bottom relaxed and longing for more attention. Butt plugs are also a dandy little tool. Even the smallest of plug’s work great to relax your anal entrance and reduce the cringe of penetration latter.

To warm things up even more, there are a few intimate tricks that work wonders too. Such as, try using a small vibrator or even a finger to stimulate the tight little hole. Even more erotic is anilingus or anal rimming. During oral sex, visiting down bellow with the tongue and everywhere in-between is a sure way to get ready for more play. Even having a vaginal orgasm before anal sex will make things easier for back door play.

The nitty gritty of anal sex.

The first rule of anal penetration is lube, lube and more lube.

With a generous dab of lube on your little hole and his rod well lubed up, it will slip in easier and smoother. Go slow and have him stop once he’s just a bit inside of you. Breathe and try to relax your muscles; don’t let him move yet.

After a few moments, have him pull back out and re-lube up your bottom and his rod.

Going back in will be a bit easier this time.

However, once again only allow him to go in a little ways and stop. Think about relaxing and take some deep breaths. When you feel comfortable begin to move your hips and enjoy the feeling of him inside of you. After your at ease, allow him to take control and have fun.

Be sure to keep the lube close at hand and have him reapply when needed.

Add extra spice to your anal sex with a clitoral vibe or by using a toy vaginally.

Being intimate in new ways is always a rocky road. Although it may be awkward, exploring new things adds a new dimension to your intimacy and is well worth the journey.

For me personally, I’ve embraced ‘Greek Love’ and enjoy it as much, if not more, than vaginal sex alone. Anal orgasms are some of the best I’ve ever experienced.

I hope these tips help you feel more comfortable and open up to new delights. You never know where the journey may take you.

One of the concerns when embarking on the journey into anal play is cleanliness. Let’s face it as erotic as anal sex is, no one wants to find mud on their hood when they pull out. Often times, this fear or surviving the embarrassment of one bad experience can be enough to detour people from anal sex.

However, with a bit of preparation, there are a few things that can be done to ensure that your anal sex is nothing but good clean fun.

Digestive Health

A diet that’s high in natural fiber (not over processed fibers) and staying hydrated is the number one thing that you can do for digestive tract health. Fiber will cause the feces in your bowels to bind together and come out as a formed solid and drinking the proper amount of water will help things flow on a regular basis.

A quick look at how the digestive track works.

The food that you eat passes through the stomach and into the small intestines. Here nutrients are absorbed into the body. Next it passes into the large intestines where the fluid and remaining nutrients are absorbed into the body. It’s at the bottom of the large intestines where the feces is held until a build up is detected by the nerves which then single the brain that it’s time to expel the feces. The last section is the rectum, which is approximately eight inches long. It’s a common myth that this is the area where feces are held until evacuating. However, in normal circumstances, the rectum is only a passage way out. Typically, people who have normal bowel movements don’t need to worry about internal cleanliness. A simple through washing of the outer anal area is all that’s needed before your play time.

For those who’s bowels are not fully formed, a few little bits may remain in the rectum after defecating. For these situations, anal douching is effective to clean everything out.

Anal Douching

For those who desire a bit more reassurance, anal douching remains the most popular option.

However, there’s great debate over the safety of anal douching. Many experts say that douching washes away much of the protective mucous lining of your rectum, leaving you open to infections. Also, anal douches can irritate or cause small tiny cuts in your anus making you more susceptible to infections. In addition, over use of enemas/douches can interfere with the normal workings of your bowels and possibly lead to your bowels being dependent upon laxatives to function correctly. Most importantly, water is absorbed through bowels and a sudden overload can increase blood volume. This can cause problems for those who suffer from heart or kidney diseases; including heart arrhythmia. Therefore, if you’re not in good health it’s always best to consult your physician before anal douching.

Although there are health concerns, when using anal douches in moderation, it’s believed by many to be the best option to have an overall hygienic anal experience.

How to Anal Douche

The goal of anal douching is to clean the walls of the rectum, not prompt you to have a bowel movement. Therefore, it’s best not to use enemas which contain laxatives or other medications. For anal douching only lukewarm water is needed. Also, a strong force of water or over filling the rectum with water may cause you to have a bowel movement if the water reaches the lower large intestine. When anal douching, only approximately four to eight ounces of water at a time is needed to rinse away anything stuck to the rectal walls.

It’s always best to douche two to four hours before you play. Douching a few hours before anal sex allows your body to expel any extra water and also gives the rectum time to reproduce some of the mucus which was washed away during the rinsing.

To douche, insert the water and hold it in for about ten to twenty seconds. Then, sit on the toilet and allow the water to run back out. Remember, the goal is to simply rinse the rectum’s walls. Repeat this process until the water runs clearish, (Normally the water will never run crystal clear since the mucus lining is also being washed away). Never over douche, since this removes too much of the mucus lining and can cause health problems. I typically douche only two times a few hours before anal sex and have never experienced an embarrassing moment.

Tools To Use

Anal douches can be purchased at most local drug stores. However they are generally marketed under the name ‘rectal syringe’. These are small bulbs with a rounded tip to make insertion easier. They can also be purchased at most sex toy stores. Also, these are also available in travel size and fit in your purse. Perfect to take along on a date or a night out on the town, these allow you to clean yourself for unexpected fun.

Anal douche hoses that attach to your bathtub are also available. However with these, it’s important to make sure that you can control the force of the water flow to ensure that damage to your rectum isn’t caused by the strong force of the water. The safest design is those that work based on gravity and not water force.

An old fashioned douche bag is another option. Although these work well, be sure to only use a small amount of water at a time and to use the anal attachment. The vaginal attachment has small holes which may not do the trick.

Enemas are a convenient, inexpensive and disposable option. However, be sure that the enema you choose is saline water. Again, other types of enemas which contain laxatives or other ingredients that work with your body to alleviate constipation can cause you have a bowel movement at the wrong time; before you play.

There’s no exact science to anal douching. Also, I’m not a medical doctor. These are just some tips and tricks to help you along your anal sex journey and not intended to over ride any medical advice you’ve received. If you experience bleeding, pain or cramping please seek medical attention as this can be a signs of serious injury to your rectum.

With a bit of preparation you can enjoy anal sex without having the fear of an embarrassing moment. The trick is to find what’s right for your body. The more experience you have with anal douching you will find the combination of time and water volume that works right for you.

When you feel clean and confident, you can relax and enjoy yourself during anal sex. I’m sure your partner will also appreciated that you’ve taken the time to cleanse yourself and make him feel more at ease also.

Have fun, relax and enjoy yourself.

Your lover’s bottom is a playing field just waiting to be explored. An often over looked erogenous zone, the two cheeks like to be caressed, kneaded, pinched, spanked and so much more.

On way to entice your lover into opening up to its pleasures is a sensual massage. Massaging this area floods the pelvis with fresh blood flow which enhances sexual sensations. Not only the butt cheeks, but also the hips, lower back, and inner thighs are highly erogenous zones. Massaging these areas just might lead to other back door pleasures.

When giving a sensual massage set the mood for your lover to help them relax. Dimming the lights and setting around a few candles are only a couple of the things you can do. Aromatherapy is also a wonderful touch to help your lover relax. Sandalwood is one of my personal favorites. Its aroma is soft, warm and woody without a smelling like perfume or flowery. Best of all, Sandalwood has an ago-old reputation as an aphrodisiac. Another nice touch is wrapping your lover’s bottom in a warm towel for a few minutes while you massage their shoulder and back. Lastly, don’t forget the massage oil. When using oil, remember a little goes a long way and excess oil may not taste nice latter.

There’s no right or wrong way to give a booty massage. However, there are few techniques that can help to make it more enjoyable experience.

Blushing Cheeks is a wonderful way to help loosen up tight and over worked muscles. For this technique, cup your palms on each cheek and rub in slow circular motions until the skin warms beneath your touch. Also, you can kneading and squeezing their cheeks with your whole hand. Once the muscles begin to loosen a bit, make soft fists and slowly kneed and twist them towards the center of your lover’s cheeks.

Surfboading is another technique that works well to relax tight muscles. Straddling your lover’s lower back work their booty from the top down. With lubed hands, place the heels of your palms just above your their cheeks and on either side of the spine. With firm pressure slowly glide your hands down the cheeks to the thighs. Resist the urge to go fast; slow deep strokes are more effective and stimulating.

Pray for More is also an excellent way to relax the inner cheeks and warm up your lover’s booty for play latter. For this technique place your palms together with the pinkies at the top of your lover’s butt cleavage. Slide your pinkies down for a slow ride, nestling them deep in for maximum pleasure. Then glide back up and slowly repeat. You can also add a wave like motion for extra stimulation.

Crease Rider will help to relax their lower booty muscles. Nestle your thumbs into the crease where the legs and butt meet. With firm pressure glide your thumbs in small circular motions. Slowly widen the circle and press deeper as you run your thumbs back and forth across the crease.

After your lover relaxes, you can move onto more concentrated A-spot massage.

Taint Treat, is a nice way to warm their tight button up. For this type of massage spread your lover’s legs wide and place your finger tips on your lover’s taint. Next, slowly and gently move your fingertips in small circles, applying only light pressure as you advance up.

All Thumbs is also a fun and effective. For this, gently place both thumbs deep between your lover’s cheeks on either side of their A-spot. With soft pressure slowly glide your thumbs up and outward. Repeat as you moving down slightly each time until you reach the taint. Repeat the process from the top again.

There are even a few techniques for direct A-spot massage.

Thumb Roller is one of Hubby’s personal favorites. With both thumbs directly on the A-spot stroke up and down as you lift the thumbs in a twiddling motion. This stimulates the outer anal rim as you slowly glide your thumbs across it. Another fun technique is the Butt Buffer. Use one lubed finger to slowly glide back and forth across your lover’s tight hole in a windshield wiper motion. Light pressure can be applied as they relax underneath erotic sensations.

No matter how you choose to massage your lover’s booty, one thing’s for sure, it’s a great way open your lover up to back door pleasures. Take your time, help them relax and before you know it their booty will be yearning to feel more.

Do you have an erotic way to massage your lover or a something special that to warm them up? Don’t keep it a secret, share your kinky thoughts bellow.