Marshmallow Jesus Guide to Anal Sex


So, you’ve been dating your insignificant other for a few months, somebody’s birthday’s approaching and anal is on the table. What do you mean it’s a one night thing and she’s up for it? Anal sex is not to be trifled with. Done right it can be sublime and incredibly intense for both parties. Unfortunately – chances are, if you’ve done it before, you did it poorly. Done wrong – quickly and without adequate preparation, particularly when alcohol is involved, it can result in agonising pain, the vile sector of santorum (look it up), or even an ‘anal fissure’ – a slow healing internal wound that will make wearing your bottom a cruel obligation.

But there’s no need to fear, with Marshmallow’s British Public Schoolboys guide to informed, ecstatic anal, you’ll be up in that booty in no time, wondering why it took you both so long.

Step One – Anal Play

Over a period of weeks you’ll want to prepare for your initial anal experience with your partner. Anal play is important – both as a form of foreplay to ensure you’re both into the experience, and to prepare the fuckee’s behind for the fuckers cock. No amount of anal play is too much preparation – it should be as far as you go at least the first few dozen times you experiment in this area. You can begin experimenting initially with fingers and tongues, and move on in later session to small flexible latex dildos or vibrators. Start playing around the sensitive nerve endings surrounding your butt, and move on to in-ass play in later sessions. Use lots of a good water based lubricant and go slowly. Anal play should be hella fun for both parties. You may want to try a variety of lubricants before finding one that has the right balance of slippy (yum), sticky (yuck) and taste for you.

Step Two – Enemas

This step isn’t strictly necessary, but is rather, highly advised – especially for first time anal. Preparing for the act itself using an enema or douche will avoid messy accidents and make your or your partners butt a prettier place to be. An enema bag resembles a hot water bottle, and is designed to squeeze warm water into your rump. Most bags come complete with a tube and a variety of nozzle attachments. You’ll want to use distilled water, available from most chemists – not tap water or any included solution (especially not saline, which can be drying, not good for anal!) to fill your bag. Enema bags come in a variety of quartages (1 imperial quart is just over a metric litre). Enema kits can be purchased in most chemists (in the laxative area or behind the counter) or from regular online stores like Amazon. A bag size between half and one quart should do unless you have an enormous arse cavity.

How to Use – Wait an hour after eating. Boil (then cool to luke warm) your distilled water, pour it into your enema bottle. Lying on your back, squeeze the nozzle in and release the fluid slowly. Remove the nozzle. Hold the fluid until your feel the need to go to the bathroom. You may experience mild cramps. Don’t worry, this is normal. Wait thirty minutes to an hour before engaging in anal sex.

Step Three – The Big Day(s)

bummingMake sure you’re both on the same page. It’s not big, clever or legal to surprise someone with a dick in their arse. Engage in lots of finger foreplay – by this point you should be able to painlessly double finger your partner. Make sure your partner is relaxed. If she or he feels tight, do other things and come back to it. This is something you want to do lots right? Don’t rush it.

When you do both feel ready, use a condom and lashings of lovely lube. Even though you should have had the all clear from your regular STI tests, lots of nasty bacteria live in the colon, so always wear a condom. Do not double dip either partners or orifices – there’s a reason pornstars get infections. Remember thesimple rule, one condom, one hole. Although if you’re a boy girl couple (or dykes with a strap on) you may want to have lots of lovely vaginal sex first.

Enter your partner slowly, continue slowly, and for Christ’s sake if it hurts stop! If done right, anal sex should never be painful. Your first time round you will probably not be able to go all the way in. This is fine, you don’t have to. Enjoy the brief experience of empathising with an enormously well endowed man. Don’t get all crazy excited and polax your poor lover. Be gentle and patient. Your partner lying face down maybe a good position initially, although doggy style (with your partner on hands and knees, use pillows to ensure their comfort), will give you more visibility and control.

If your partner is experiencing tightening you may want to try poppers (myl or other alkyl nitrates) a (legal – at least in Ireland) sniffable drug sold in little bottles (often marked as room deodorisers) in sex shops (for between five to ten euro). Popper are a safe muscle relaxant, but may result in headaches for some folks. A few sniffs should relax your butt.

For more information check out ‘the ultimate Guide to Anal Sex for Women’ by Tristan Taormino and ‘Anal Pleasuure and health’ by Jack Morin. Also check out Dan Savages excellent weekly column ‘Savage Love’ and his podcast the ‘Savage Love Case’, available at the


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