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ANAL SEX

Part I: Learning the ropes

It can take quite a while to get comfortable with anal sex, especially when there have been bad experiences in the past. So, either be prepared to be patient, or don't even attempt it.

First, trim your nails.

Spend a few sessions playing with your lover's asshole with the clear understanding that you won't use more than one finger until they say they're ready. This will allow them to avoid the nervous anticipation of imminent pain, and learn to enjoy the sensation of anal penetration. Make sure, too, that it's very clear that you want and need feedback; if you know what's going wrong when it goes wrong, it'll be a lot easier for you to figure out how to fix it. Communication is essential. And of course, remember to pay very close attention to nonverbal responses.

For any anal play, use lubricant. Lots of it. Do not use an oil based lubricants: they dissolve condoms, and even if neither of you has ever had another sexual partner, it's still advisable to use a condom for anal sex. This protects both of you.

I recommend that you have your lover lie on their side for anal play, until you're both very comfortable that you know what's happening. This allows them to pull away if they need to --- there's a lot more control for the person being penetrated, and it's not at all awkward for anal sex --- everything lines up, and there are no legs in the way. I find that it's easier with my legs pulled up in front of me.

Through all of this, too, if something seems to hurt them, freeze --- do not remove your finger suddenly. If the problem is a gradual loss of lubrication to the point that there's some unpleasant friction, pulling out quickly can be quite painful. It's usually okay to keep going after unexpected pain; just give them a chance to relax and recover, with no new stimulation, then start back up slowly.

Now, how to do that one-finger playing? For starters, don't start there. Play in a comfortable, familiar pattern first. Anal sex is much easier to relax for if you're already turned on. When you think it feels like the timing is right, start playing with your lover's ass and around the opening to the anus. When the response to this is increased arousal, get a bit of lubrication on your finger (it's better to go back for more than to have a big gob, the stuff tends to be cold --- if you need a lot at once, you're going too fast) and, pulling their cheeks open with your other hand so you can see what you're doing, put it on the outside of their anus. Press very gently, rubbing in a small circle. Press a little harder, until the tip of your finger is in. Hold still for a few seconds, then move it in a small circle. Vibrate it a little bit.

Gradually, go in deeper. Stop every so often, and move around gently. Pump in and out, again gently, and slowly at first. Stop for more lubricant if you need it. You can increase the diameter of the circles slowly; if your lover seems very tense, tell them in a soothing voice to relax (the finger should probably be still at this point). With your free hand, stroke their back and hair; kiss their thigh or hip. Gradually start the finger play again.

How long this goes on, and just how enthusiastic it gets, will depend on how much your lover enjoys it. Read their responses closely. If in doubt, ask. Hopefully, at some point either body language or verbal communication will let you know that you're going too slowly and/or gently. Focus on your lover, and trust your instincts.

Once one finger is familiar, you can either use a slim vibrator (not necessarily turned on all the time), or two fingers next. Depending on the size of what you want to put up them, you'll want them to be able to take at least two fingers, maybe three, comfortably before trying intercourse.

When you finally feel ready to approach intercourse, lie side by side with you behind them. Your lover's ass should be thoroughly greased by your play; put some lube on your cock or dildo as well (don't overdo it, or it'll squirt around and be more difficult to control :-). Set the head of your cock or dildo at the opening to their anus, then have them push back against you. You'll be braced against the pushing; let them control the speed of penetration, and freeze when they freeze. You'll have access to lots of their body (though they may find this a distraction); if there's pain, remind and help them to relax.

One other thought --- it's possible that part of your lover's mind is taken with the concept of fingers in the ass; any time that part of the mind is turned off like that, it'll get in the way. If they think that could be part of the problem, they might be more comfortable starting out with the slim vibrator or dildo, and working up to bigger ones. The smallest buttplug I've seen would probably not be useful to start with --- it's not what they're designed for.

And when you're all done, wash hands, other bodyparts, and toys carefully, with lots of hot soapy water; always keep the ass and things which have been in it away from penis, vagina or urethra. E. coli can be nasty in the wrong places. Toys, especially porous ones, are best kept separated.

Have fun!

Part II: Getting used to it

Anal sex can be pleasurable for both the inserter and the insertee, but some preparation may be needed. Anal penetration does not have to hurt, although it often does the first time people try it. Go slow, and communicate!

Some things to be aware of before you start...if you are with a woman, never, never go from her ass into her cunt --- the bacteria in each are drastically different, and can cause some unpleasant health problems. And remember to always use a condom!

Make sure that you have lots of water-based lube around. The more lube the better! Some water based lubes include: KY, Astroglide, Elbow Grease, Probe etc.

Relaxation

Part physical, part psychological. Very important: You must really want something inserted to your ass. Pain can occur if Bottom isn't relaxed or if Top is pushing too hard, or if there isn't enough lube. Bottom is responsible for telling Top how things feel, if they are ready for more or wants to back off. Go slow. Work up to more vigorous activities. Your anal sphincter is a muscle and you are going to learn to control this muscle. Fear, embarrassment, and pain will cause you to tighten up. Hot baths, a good, firm massage, deep breathing, or a cup of hot tea/chocolate will help to relax you.

Part III: Using a butt-plug

Ideally, you should train every day, or at worst every other day, until you reach graduate level. This will maintain the physical stretch that you are trying to develop, and keep your ass in a constantly excited state. If you get very sore, you are going too fast, so stop and take a break for a while.

A butt plug, is a smooth, T-shaped piece of rubber or latex. The long part of the `T' starts out at a blunt point and widens considerably towards the middle.

You can buy these by mail order, or at a sex shop in various sizes from tiny to Oh-my-God! You should select a size that tapers up to slightly larger than the cock or dildo you are going to be fucked with, at the plug's widest point. Perhaps your lover will take you with them to the shop to help select it. It should be washed at the end of anal sex, always.

Some receptive partners feel pain because hairs around their assholes are being pulled during anal sex: it's easy enough to trim them.

Variation for all stages

Lie face down on the bed with a pillow under your hips. This will raise your ass for your lover's convenience.

Curriculum

Freshman (needs privacy and a lubricant)

1. Finger penetration first: the penetrative partner sits on a bed (or an armless chair for back support). You lie down over their lap with your bare bottom open to their touch. They begin by stroking slowly up and down the outsides of your cheeks, perhaps lightly using the fingernails, but staying away from your cock or pussy at first.

   Gradually they get closer and closer to the crack of your ass, stopping to lubricate the fingers, then continue. Using the other hand to spread your cheeks, they start to spread the lubricant from just below your asshole to the top of your crack, rubbing a single finger up and down and up again, but not entering you. They ask you how it feels. Tell them.

   They then begin to rub the ring of your ass with one finger, going around the outside first, then the center, rotating gently and pushing outwards. After making you wait for a while, they begin to push a well-lubricated finger into your ass, just to the first knuckle, while finally starting to play with your pussy or cock.

   They keep the finger still, but play with you until you start moving. They ask you if you want more, when you feel ready, tell them. They gently begin to move their finger in and out of you, just a ¼'' at a time, gradually sliding deeper until they are in to the second knuckle. They stop again, and watch you move on their finger. They slowly begin turning the finger slightly, and go back to the pumping action of before, but moving a little more now, exploring your inside with their finger tip. They ask you again if you like it, and you tell them.

   They can play with your cock or pussy and your ass until you cum with the finger all the way inside you, so they can feel every wriggle and shudder. When you have finished, they slowly pull their finger out, and you satisfy them with your mouth, cock and/or pussy. After they cum, they whisper in your ear that next time, you will feel the thickness of their thumb.

2. Using the thumb: as before, substituting thumb for finger.

3. Responsiveness training: in subsequent sessions, your lover plays with your ass a bit more, and your pussy or cock a little less each time, until you can almost cum from your ass sensations alone.

Sophomore

1. Needs the above plus a butt plug: this time the butt plug and lubricant are laid out in plain sight as you undress for your lover. After lubing and fingering you as before, they take the lubed plug and stroke that up and down your crack instead, then place the tip directly over your asshole.

   Letting you wait, they start to stroke your cockhead or your clit and pussy with the other hand, until you are almost ready to beg them to start exploring your ass. Your lover asks you if you want the butt plug inside you. When you are ready, say so. They push firmly on the plug, but only let the very tip enter you. Breathe deeply and concentrate on how open and excited you feel.

   They begin turning the plug gently, playing with the opening of your ass. When you feel ready for more, you tell them, and they slowly push the plug a little (<½'') deeper into you, letting you relax around it.

   When you can't take anymore, ask them to stop, but keep the plug at the same level. Wait 10 minutes while they play with your pussy or cock. See if you can take it deeper. If you can't, then wait a while longer at that level, until they remove the plug slowly and you both cum anyway you like.

2. Try each time to take the plug a little deeper. Your lover can show you the plug before each session.

3. If you can't be trained every day, your lover may choose to assign `homework', where you lube and stretch yourself with the plug. Although this is really a more advanced exercise, and may actually be harder for you to remain relaxed, it is important at this stage to have your ass worked at least once every 48 hours, otherwise you might lose progress.

   Play with yourself just as they would and try to go a little deeper each time. Perhaps they will phone you with instructions and have you tell them how it feels inside you...

Junior

1. You reach this stage when you can take the thickest part of the plug in your ass. Your lover may choose to reward you by turning on the vibrator, and you both should celebrate, (perhaps eat some ice cream off each other?).

   They continue to play with you, but it no longer has to be quite as slow, and you will spend much more time being plugged, getting used to the stretched, full, but not painful sensation.

   After you can spend an hour or more this way, you can go out together while you are plugged (wear panties to hold it in), and they can watch your expression while he turns the vibrator on in public (keep the control in your pocket). While they vary the speed, they can tell you just what they want to do to you when you get home.

2. While you lie face down with your hips up on a pillow, your lover slides the plug deep into your ass, plays with you a bit, then either climbs on top of you, firmly entering your pussy and fucking you, or sucks on your cock, as long as possible before coming. Just before they come they turn the vibrator on so they (and you) can feel the vibrations between your passages.

3. You lie on your back with your legs on your lover's shoulders. They plug you, turn on the vibrator, and tease your cock or pussy with cock or dildo until you beg them to fuck you.

4. Show your lover how good you have become at accepting your butt plug. Either as a surprise for them, or at their command, strip and lube yourself, then insert the plug into your ass making sure that they have a good view. After working your ass for a while, ask if you have pleased them, and if you can please them some more. Should they say yes, ask them to lie on their back, keep working the plug in and out, and hand over your vibrator control, kneeling so they have a good view, and use your mouth to satisfy them.

Senior (it's time!)

1. After you have accomplished the above, you'll reach a point when your anticipation level and the tingling in your ass grow to the point where you can't stand not having your lover fuck your ass any longer. This is when you know you are ready. Decide several days ahead exactly when you'd like your first time to be. Then during those days, don't cum! You may please them with your mouth or otherwise, but explain that you are putting yourself in a special state of readiness. Then, on the big day, take a long hot, bath, share a glass of wine and either:

   • lube and plug yourself as above, get into the usual facedown, hips on a pillow position, ask them please to remove your plug and fuck your ass, or:

   • simply get in position, and ask them please to play with your ass, then fuck it.

2. Either way, they may want you to do other things first, and it is to your advantage if your lover is very horny, yet not in a rush, so you may want to suck or lick them until they cum, then lick them back to arousal before you offer your ass.

   They should hold the dildo or cock near the tip when they first enter you, to avoid bending, and should not thrust much at first. Just the long, first glide that opens and fills you completely, then a wait, and a building of thrusting and pleasure for you both. Denying yourself an orgasm for several days and all of your previous training will combine to make this a very special time. You will probably feel like a kid with a new toy, but try to get into it gradually over the next few weeks until it becomes very easy for you. You can always include any part of your training that excites either of you in your usual play. You can consider yourself a graduate when they can enter your well-lubricated ass as easily as they could a wet pussy.

Postgraduate  ( for advanced/enthusiastic students only)

1. Keep small packets of lubricant on you at all times, since you never know when your lover will require your ass to serve them (KY Jelly comes in such packets).

2. Now that you know you can accept them, try alternately relaxing your ass when they stroke into you, and tightening slightly as they withdraws. This feels wonderful!

3. Try different positions. On your back with your legs on their shoulders; both of you on your sides like spoons; you bent over the edge of the bed, them kneeling on the floor behind you, etc. Positions that require a lot of leg tension on your part are not as simple to do at first (standing, bent over, hands and knees, propped against a wall, squatting or kneeling over cock or dildo etc.), although they may give you more control of depth and thrusting (assuming you want control). One thing you might want to try any time you are lubed and facing away from them, is to spread your naked cheeks wide with both hands, saying quietly, `This is for you'. A very powerful submissive image.

4. As a variation on (3) above, they may hold/tie you to keep you from moving your body, slide deep into your ass, and while not thrusting themselves, have you squeeze and release with just your ass muscles until they cum. Quite difficult, but worth it.

5. At your request or theirs, set aside a particular weekend or other such time exclusively for anal sex. For example, you may use your tongue on them, but only to get them aroused enough to fuck your waiting ass. This will leave you tired, and maybe a bit sore, but very satisfied.

6. For women Bottoms, have him deep inside your pussy before you or he inserts the plug. This suddenly makes your pussy seem much tighter, and then of course, you can both enjoy good vibrations.

7. Don't always use the bedroom. One of my favorite times was very impromptu. I simply led my already very experienced, highly excited lover stark naked and lubed out into her living room, placed my hand firmly on the back of her neck, and had her bend over the back of waist-high armchair. I then opened my robe, grabbed her hips and entered her, thrusting firmly. She later told me that she had lost count of her orgasms during the first 30 seconds after my entry, and that it was a good thing that she wasn't `a screamer'. I just thought it was a good thing she had very thick opaque drapes on all of her windows...

8. Sometime shortly after they fuck your ass, maybe as soon as you wash up, bend over, spread your cheeks with both hands, and look at yourself again in that mirror. Now, haven't you come a long way? Share the view and how it makes you feel, with the person who's just been deep inside you.