Note: The following is from the perspective of a heterosexual guy. Replace she with he, her with his, etc. if necessary.

Many women yearn to try this last of the taboos, but there seem to be few statistics on how many like the experience, and even less information on how many repeat it. What follows is based on my own experiences, in the hope that it will help a few more people enjoy this activity. I especially hope some of you go back for more!

Yes, I’ve done it, and yes I loved it. So did the women involved each time. I’m not trying to brag, but if I accomplish nothing else in life, I’d at least like to think I have made a few converts to the intense pleasures of anal sex. Despite the warnings which follow, it can be amazing and intense for both people when done right!

Warnings, prison jokes, and pain:

One ex-gf of mine had an abusive and physically damaging Experience involving no relaxation, little trust and even less lube! Another friend tells of a boyfriend who was drunk and just jammed straight in the wrong hole, with no warning! Yet another friend tells of her guy coming up behind her, while she brushed her teeth at the sink, and just going for it. Still others have seen that infamous scene in Deliverance, and cringe every time they hear “Dueling Banjos”. For every person who loves anal, many more tell cautionary tales, relating bad experiences because of inconsiderate partners, wrong or insufficient information, little or no preparation and impatience. The good news is that, with consideration for her, communication, trust and preparation, you can avoid all of this, and hopefully win another over to the dark side of the moon.

Anatomical basics:

“Woe boy, the butt is not just a tighter pussy!” While the vagina can

expand like a balloon to accommodate girth – baby’s pop outa there after all – the tissues of the rectum are some of the most delicate in the body. They are not supposed to stretch far, and do NOT lubricate themselves. This last bit is most important. Do not believe what you read or see in porn; it is a myth that a little spit on your dong will make it all good. It won’t! A little transplanted pussy juice won’t sufficiently combat the “ring sting” either! Think about it. We’ve probably all had a big bowel movement that either hurt coming out, or caused pain we noticed later on. “Hmm, I think I can see the stitching on the baseball!” Blood is not a good lubricant for anything!

Condoms, to use or not to use:

If you’re using condoms, do not use those coated in spermacide as the delicate tissues where we’re going are easily irritated. Be careful with products containing perfumes, dyes, and sugars. Smucker’s Plumb Preserves are not the right lube, despite what Little Jack Horner may have told you. If you’re using condoms, also use a water-based lubricant, and lots of it! More than you think you need is almost enough.

If you’re not using condoms, assuming things have been nicely inspected, cleaned, prepared and gently probed, and neither of you have STD’s or hepatitis, you can use oil-based lubes. Believe it or not, a clean anus is probably no dirtier than the average human mouth, which is actually teeming with nasty bacteria. Personally, I love good ol’ baby oil back there. It’s delightfully slick and slippery, and it doesn’t disappear like some of the water-based lubes do. Besides that, its innocent smell contrasts nicely with the rather raunchy taboo activity you’re about to engage in. Cleaning and preparing is a necessary part of it, so enjoy it and think of it as a cleansing ritual. Cuddle in the bath together.

Preparing thy way:

Besides lube, the other watch word to keep in mind is RELAX! This cannot be

willed or forced mentally. The sphincter, that cute wrinkly muscular ring at the

entrance, is under involuntary control. You cannot fake being

relaxed or ready, any more easily than you can stop your heart or

stop breathing. If you’re afraid, tense, or nervous, it’ll stay tight! Cumming hard a couple times, through whatever way works best for her, may help a lot.

“Love, is a Burning Thing; and It Leaves a Fiery Ring”:

And now, we learn the other meaning of “digital.” First, train the butt to accept small things before you go for the big one. Maybe give her a shoulder and back massage, and at some point, work a well-lubed baby finger in. (Kinkier readers may wish to try wearing a small butt plug while doing household chores, masturbating, or attending Easter dinner with family, to get used to that fuller feeling.) Regardless, go straight and slow and make sure your nails are trimmed short. Once she’s grown

accustomed to that, go for a slightly larger finger, again, well-lubed. Eventually, you may work up to two fingers at once, and be able to gently flex them inside. The entrance is full of nerve endings and blood vessels, so it tingles and feels very intense when things move through it.

Positioning, AKA “c’mere biotch”:

So, she’s relaxed, she tells you she’s ready, everything is all soft and yielding and slick with lube. It’s time to get very very intimate back there. Maybe things are more relaxed if she’s on her tummy, pillows making everything comfortable. Maybe her lying on her side is more comfortable. Both are probably better than her on all-fours or on top, neither of which promote the necessary relaxed state. Maybe the shower or bathtub will work better than the bed – you’re going there after anyway.

“Shake hands with Beef”:

Lube up your cock and maybe squirt a last little bit into the cute quivering little target. Maybe get her to lube you up. This might get her more excited, feeling the large, smooth, greasy thing about to enter her most private area.

Pop Goes the Weasel:

Carefully aim straight ahead, go slow and listen for directions from her whether to stop or move forward. Getting the head past the tight opening is the trickiest part. Telling her to push, as if she’s trying to expel you, is helpful. This doesn’t actually push anything out; instead, it helps the muscles relax and loosen. The entrance will probably yield with a little “pop” feeling that I’m sure both of you will like. Stop once you’re

inside a little, and let her adjust to having you there, and the new and intense stimulation you are giving. If things sting a little, just relax and wait. The fullness can feel amazing if you let it!

The Train Tours Hersheyville:

Ease forward, and keep going if she says it’s ok. Before you know it, you’ll experience the amazing contrasting pleasures of a tight, rubbery muscle around your cock, and the lovely pillowy softness of your hips, balls, and lower belly against her buns. Gently pull back, then ease forward, noting how the lube and all the preparation makes it easy, slippery, and very hot! Again, coming to rest fully inside, the tightness combined with the softness around it, is the magic part for me. If things are perfect and relaxed, you may even be able to give a little push near the entrance, and feel the combination of lube and momentum carry you all the way back in.

“Onward Christian soldiers”:

Can you pick up some speed at this point? Yes, if she says so. The important thing to remember is to be direct. Go straight forward, don’t try to be fancy. No shimmying, just follow the lovely slick road. Your cock will take the path of least resistance all on its own. Don’t pull all the way out, although she may love the feeling of you pulling back most of the way before each thrust, so this too can be great. Pick up speed and always listen for directions from her. Can things get slammin’ and sweaty and downright beastly? Most definitely! That’s why you made all this effort in

the first place.

“And the rocket’s red glare, the bomb’s bursting in air”:

Yes boys and girls, saying “no” to “bush” in this way can be a political protest! At this point, cumming quite fast is not a problem, if you’re anything like me. However, she will probably need some help. She can reach under and play with her clit, or tell you to do so with your hands. A vibrator could be placed under or in her. Nibbling the back of the neck, shoulders, or ears, slight or not to slight hair tugs, nipple pinches, or shoulder grasping may be required, if she likes things a little rough. You are much more likely to be permitted back there again if she enjoys it though, and her cumming hard while you’re in deep greatly increases your odds!

And After?:

As always, cuddling after is nice, but even more important here after something so special and intense. Talk. Stay inside if you want, because unlike vaginal intercourse, your softening cock is less likely to slip out. A shower or bath together is both loving and good hygiene. Carefully wash and caress those tender sexy parts you just explored. Similar to what it says on the shampoo bottle: “Sodomize. Rinse. Repeat.”


1. I am pleased to report that some other curious wenches have tried anal for the first time, thanks to previous versions of this document. Daddy is so proud!

2. “Ring of Fire” is apparently about Hell, but who cares, right? Apologies to Johnny Cash. (Also check out the Frank Zappa cover version on The Best Band You Never Heard In Your Life, disc 1).

3. “Shake Hands with Beef” is actually the name of an unrelated song by the band Primus. They, like the music of Mr. Zappa, are highly recommended.

4. “Onward Christian Soldiers” is a Protestant hymn, and if using it’s title here causes just one of you to laugh while in church, I have done my good deed for the day.

June 2018
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