Some experts say if you do anal sex ‘properly, it won’t hurt. I say even if you do it correctly, the urge to say ‘Owwww! That bloody hurt!” will strike you at times.

The anal sphincter muscles are used to pushing things out, not taking things in, so you literally have to retrain your bottom.

You can only do this by taking things slowly and preparing for it properly (see How to prepare your bottom for anal intercourse).

But while it’s uncomfortable some of the time, it shouldn’t be really painful. If it is, you’ve rushed into it or you’re a bad fit (too small bottom with too big penis!)

Ironically, it will sometimes feel most uncomfortable while the penis is shallow.

That’s because it’s passing through two different sets of sphincter muscles which are determined to guard against intruders.

The external sphincter is controlled by the central nervous system, meaning you’re (kind of) in control of it.

The internal sphincter is about an inch further in and it’s controlled by the autonomic nervous system (it’s controlled by your body, not by you).

You can help relax both sets by bearing down (imagine you’re doing a big poo and push out).

Once the penis is through both sets of muscles and deeper, it should feel more comfortable.

BUT don’t rush the process to put it inside: take it slowly and while it may feel uncomfortable, it’s not unbearably painful. Barge right in and you’ll be hitting the ceiling.

Once you relax into it any pain should subside and the pleasure factor should start to kick in.

Never EVER attempt penetration without first inserting fingers or anal toys – the rectum needs time to get used to things inside it!

You can do this with your partner but you can also do it solo.

If you’re keen to try anal intercourse, prepare by gently inserting a finger into your anus for a minute or two every time you have a shower.

Yes, you will feel mighty weird doing it the first few times but it works.

Insert a fingertip and feel around, identifying both sets of anal sphincter muscles (the external and internal – more about those later) and squeeze the muscles around your finger.

If you’re with a partner, get them to apply lots of good quality lube to both the pad of their finger and the outside of your anus (you MUST use good quality anal lube – thick, slippery and heavy duty – to make anal intercourse comfortable), then massage in a gentle, circular motion.

Wait until your muscles relax, then get them to insert their finger in a little.

Once they’ve been doing this over a few sessions, get them to insert two fingers.

The next stage is to use a butt plug: a small toy that you put inside and leave in while they give you oral sex or stimulate you with their hands or fingers.

Plugs get the rectum used to relaxing around an inserted object.

Glass dildos work well anally because they slide in easily and you can start small and work up to the same penis size as the person penetrating.

Why not go straight for the real thing? Because the dildo isn’t likely to get carried away and start manically thrusting before your partner is ready!

1.Play with his hair.
2.Rest your head on his shoulders.
3.Let him rest his head in your lap.
4.Massage his feet.
5.Take a bath or shower together.
6.Slow dance.
7.Rest your hands on the small of his back.
8.Hug him from behind.
9.Kiss his neck.
10.Give his bum a “love tap”.
11.Plan an intimate night for just the two of you.
12.Get him a body massage.
13.Kiss his forehead.
14.Squeeze his hand when you say goodbye.
15.Greet him at the door with a kiss.
16.Sit in his lap(When the setting is appropriate).
17.Cuddle with him for a few extra minutes in the morning.
18.Place his hand on your tummy or waist when you’re cuddled up together.
19.Rub/touch his arm when you walk past him.
20.Have a “Wrestling match” or a “tickle fight”.
21.Cup his face in your hands when you kiss him.
22.Wash his hair and massage his scalp.
23.Wink at him.
24.Foreplay.
25.Lotion his hands and give him a mini spa-like treat.
26.Whisper in his ears the many reasons why you love him.
27.Scratch his back.
28.Use your body language to flirt with him.
29.Grab his arms and wrap them around your waist.
30.Put your hand in his back pocket while you walk together.
31.Grab him by the neck and pull him close.
32.Try new sex way,like the anus sex.

If you haven’t already , you should explore your anus with your fingers before you even consider a toy. Get to know the area a bit before you start putting stuff up there!

Any toys that are going into your butt need to be thoroughly cleaned before (and after) penetration. Hot water and soap are usually sufficient, but you can also find antibacterial sprays specially formulated for sex toys. Some toys can also be sterilized by boiling them (or even putting them in the dishwasher); check your toy’s manual for specific instructions (and ya know, maybe don’t toss your dildo in the dishwasher if you have roommates around).

For your first foray into anal sex toy land, think about whether you want to be the one holding the toy, or if you’d like your partner to do it. If you’re nervous, I’d suggest being the one to hold it, since you’ll have more control. A partner has the advantage of being more dexterous, but you’ll have to make sure to communicate with them about what feels good and what doesn’t.

Next, find a position that gives you good leverage. The arm that’s operating the toy will need to stretch further than you usually do when you masturbate. Sitting up in bed with some pillows propped behind you is usually doable. If you’re with a partner, they can sit between your legs. You want to be relaxed and turned on before venturing backdoor. One of the challenges of using anal toys is getting your muscles relaxed enough for penetration,so do whatever tickles your fancy: put some fingers up there, masturbate, get your partner off, watch porn, fantasize, you know the drill.

Make sure you have your trusty lube nearby. If you’re using a silicone toy, you’ll need to use a water-based lube (silicone lubes can break down the silicone in your toy). If you’re using a stainless steel toy, you can go for silicone or water-based lube.

Next, whoever is wielding the toy should pick a designated butt-hand. You want to be careful not to get fecal bacteria in your other orifices, so use just one hand to touch your asshole, and keep it off-limits from any other activity. Put a nickel-sized amount of lube on your fingers, and apply the lube to your anus. You can push your fingers in a few inches to get some lube inside and prepare yourself for the toy. Then thoroughly saturate your toy with lube. You want it so lubed that it practically slips out of your hand. Lube is your friend when it comes to anal, and you really can’t use too much. For peace of mind, you can put a towel under your butt to guard your sheets against lube spillage.

Holding your toy in your butt-hand, press the tip of the toy against your anus as you continue masturbating. Just hold it there for a few moments while your body adjusts to the pressure. When you feel ready, gently push the toy in about an inch or less, then hold it there. If this feels painful or like there’s too much resistance, slowly pull the toy out. Hold it against your anus while you keep masturbating. You can also add a little more lube if you feel like the toy is tugging at your skin or not gliding smoothly. If all systems are go, slowly slide the toy further in, an inch at a time, taking breaks to hold it in place and keep masturbating. Once it feels like the toy is fully inserted, try taking your hands off of it. Some toys will stay in place snugly, while others may get pushed around a bit by your sphincters. If it feels like your butt is pushing your toy out, just hold onto it to keep it in place. If your toy has a flat base, you can sit up a bit so the base comes in contact with your bed and keeps the toy inside. You can keep the toy stationary, and enjoy the sensation of fullness it creates. Or try moving it in and out or around in circles.

When your orgasm, your muscles will contract, and will attempt to push the toy out. This is where having a towel beneath you comes in handy! You can let your body do its thing without having to scramble to catch the little plug being shot out of your butthole. The sensation of the toy coming all the way out of your asshole can feel a little bizarre, so just take a deep breath. If it doesn’t come out on its own, ease it out slowly. You may be tempted to pull it out quickly, but doing so feels a little too similar to pooping, so take your time.

If you’re using a toy with a partner, you may notice that the anus stays agape after the toy has been removed. This will be especially noticeable if you used a girthy toy. Don’t worry, your butthole will return to its usual puckered state in just a few minutes. Just pretend it’s saying “WOW!”

Wrap your toy up in your towel or in some Kleenex, and take it to the bathroom to clean and sanitize it. Don’t forget to wash your hands with soap and water, especially before touching other parts of your or your partner’s bodies.

Congratulations, you’ve now leveled-up in your anal adventures!