I’ve heard it 863 times now (I’ve been keeping track). “I tried it once and it was awful.” Or “My ex did it to me once and ruined it for me.” Or “I’d like to do it again but I’m afraid it’ll be as bad as the first time.”
With a fervent desire to elevate butt-luv to the highest echelons of sexual experience for as many people as is possible, I would like to give you some ideas about how to make your first experience with anal so amazing that you’ll want to try it again. And again. And again.
A caveat: I am not an expert. Read here for much more information on the topic in general, or here for some panty-drippingly hot personal accounts and instructions.
I have but one iron-clad rule which I will get it out of the way first. Both the giver and the receiver of the anal attentions must want it and want it badly. If this criterion is not met, nothing else will go well, no matter how hard you try.
If the penis-owning partner wants no part of inserting his willy into your ass, or if the ass-owning partner can’t imagine being penetrated in that manner, you are SOL. I can’t help you.
If the receiver really, really wants it, the first thing she (here I’m making the wild assumption that she will be a she; of course she needn’t be a she, but I am a she, so there you go. Extrapolate at will.) must do is practice on her own. No partner. No audience. No help. Privacy is absolutely necessary.
To get comfortable with anal play, you have to convince yourself that you can have things in your ass without poo going everywhere and without horrific pain. You can–but you won’t believe me until you try it for yourself.
For this part of the program, I suggest a very thin dildo. Be sure to select a dildo with a flared base made specifically for anal play, as the last thing you want to do on the same day that you violate your own virgin ass it to have to haul that ass to the nearest ER for the surgical removal of a toy from your rectum. This would be exceptionally awkward. Flared base. Got it?
Also, invest in some high quality thick lube. Maximus is nice, but the Sliquid line is almost as nice and it doesn’t have the drawback of an icky taste. Thus you can repurpose your unused Sliquid for any activities requiring lube, just in case your anal adventures are a complete bust.
Put the dildo and the lube within reach of the bed. Add to the pile your favorite method for working your body into a pre-assplay frenzy. I like a good strong vibrator. Do you like porn? Turn some on. Will fingers suffice? So be it.
Toss down an old towel of a darker shade on the bed. I have a black towel expressly for this purpose. Place another dark towel near the bed. You’ll need this later. Then hop in bed and make sure everything you need is within reach.
You may notice that I’ve said nothing about enemas. I’ve not yet tried an enema, although I’m not against their use. If you feel the need, go right ahead. If you’ve recently used your butt for its primary purpose, an enema’s probably not going to add much to the cleanliness aspect, but if it makes you happy, enema away.
If you are multiply-orgasmic, get your bad self off in your standard way a whole lotta times before you even think about your bottom. If you aren’t multiply-orgasmic, get yourself exquisitely, throbbingly close to an orgasm a few times before you even think about your bottom. Your goal is to be so achingly horny that your inhibitions drop to nearly nothing.
Then lube both the dildo and your ass liberally. Make sure the lube goes right up the shaft of the toy, as that part may eventually be inside you too. If the toy has a long enough handle, you can try inserting it while you lie on your back. If not, roll on your side with one knee pulled toward your chest.
When first you try to insert a toy, your ass will be very confused. It will be all agog with wonder that something is violating the rule (One Way Only!) that has been so strictly followed up until this point.
Asses can be stubborn creatures and comfortable in their habits. Your job is not to force your ass to bend to your will. You must coerce your ass. Romance your ass. Woo your ass. Nudge the toy ever so gently against the opening until it wants to open up.
It will help if you do two things at this point. First of all, if you can in any way manage it, keep up the stimulation you were using before. Can you wedge a vibe against the bed? Can you nestle a bullet between your labia? Can you keep on watching porn? Good. We’re not trying to pull a fast one on your butt. We’re only trying to keep the level of happy relaxation going.
It will also help matters greatly if you push gently out against the dildo you are attempting to insert. Yes, push out. When my dear friend and butt-mentor first explained it to me, I didn’t believe him. But pushing out against your toy will actually open up your bottom wonderfully. Don’t believe me? Try it.
You will feel some resistance, but if you are sufficiently lubed and horny as hell, the tip of your dildo should eventually make its grand entrance into your bottom. Go very slowly. Do not force it.
If this time it doesn’t go, relube and try again. Or not. It’s not a competition to see how much / how fast / how many / how large you can take. The more relaxed you are, the easier it will slide in. But if it doesn’t, just finish getting off and try again another day. A not-forced bottom is a happy bottom. A forced bottom has the potential to make your life exceedingly miserable.
It make take you several sessions before you can insert your toy. That’s alright. The goal here is to be able to have buttsex eventually. You may have to practice for weeks before you are comfortable enough to move past this point. If your partner is understanding, he’ll wait. If he’s not, then he doesn’t deserve to get into your ass in the first place.
After you have gotten the toy into your bottom successfully, you’ll want to play. Thrusting is nice, but it’s not for everyone. Try it and see, because it’s especially nice to be able to hit your g-spot from inside your ass. It’s really especially nice.
But if you find this less nice than I do, think about experimenting with clitoral stimulation while your dildo simply rests inside your bottom. This also is amazing.
You may need to wedge your toy against the bed in some way so that it doesn’t shoot out of you. Butt-muscles are surprisingly strong, and while it can be damned funny when your butt fires your toy across the room, your cat will be pissed as hell if he gets hit in the head with it, and you will be less than enthused if this happens right as you are about to come. To avoid this possibility, find a toy with a thin neck designed to stay in while you play.
Orgasms with something in my bottom feel completely different than orgasms without. I feel more opened, more exposed, more hot. Expect yours to feel different as well.
When you want to take your toy out, you again will need to work very slowly. Give your bottom time again to open up, and under no circumstances should you yank the toy from your body. Gently pull on the toy, going especially slowly when its head is coming free of your body. Push a little if you can.
It’s not stuck. Really. Just keep working it.
When finally it breaks free, use the towel that is not under your bottom both to wipe up any drips (there will be drips) and to wrap the toy. Get that bad boy to the bathroom as soon as you’re done cuddling with yourself. Give it a thorough wipe off and bath.
During my year-plus of playing with my bottom, I have yet to experience a feeling I’d describe as pain. Some people do. I’m just lucky, or have a high pain tolerance, or a slight degree of brain damage, or something. But if you feel pain that does not resolve almost immediately into intense pleasure, you should stop.
Don’t for the love of God even dream of using any kind of desensitizing product. The point of buttsex is pleasure, not numbness, and if you even briefly trick your body into ignoring pain in the moment, you can rest assured that it will repay you with additional pain on the following day.
Later we’ll continue our lesson on buttplay. We’ll talk about how to incorporate your partner into your buttplay in such a manner that you’ll both want to try it again and again and again.
Now get on outta here and practice. Then come back and tell me how it felt.
Amen to that.
(Surely that was blasphemy.)
Saying AMEN about buttsex?
I dunno…buttsex always makes me pray…
Also (sorry for the double comment), for beginners – or, hell, anyone – I would recommend the Little Flirt buttplug. They sell ‘em at Babeland.
Funny! I linked to the Little Flirt!
Amber, we can just hang out and talk about buttsex alllll night long, if you’d like.
:)
Embarrassed! I totally did not see that one of your links went to the Little Flirt until after I posted that comment. Sorry. :P
However, I have had many instances of the Little Flirt shooting dramatically across the room. Interesting that you mentioned it as one that stays in. I like it a lot, but that’s not one of the reasons.
And, yes, I am fine hanging out and talking about buttsex all night. :)
Oh god, does it shoot???? Oh noes!
It’s just too damn funny when they go bouncing merrily away.
Unless they are messy. Then it becomes not so much fun.
i haven’t had butt sex in a decade but i was just getting in the mood to try it with my now ex lover when he became my ex lover. i think i’m kinda glad now that i didn’t do it with him.
somehow it’s more intimate to give that away for me and though i’m stoked to try it again now that i have a sex drive i think maybe it will have to be with someone i’m deeply involved with
that said, i use the ‘g spot stimulator’ on my butterfly and sit on it. i really do need a proper little toy but that works quite well.
This made me laugh explosively more than once. That, and it also made me, once again, curious about buttlovin’.
I think Amber should comment again. That was amusing. :-)
Well, dirty filthy princess, I don’t know what more you want from me… I’m not sure I could top the “shooting dramatically across the room” comment! ;) (At least I don’t have a cat or dog to hit in the head.)
Its an odd thing. Some of the most earth-shattering eyes-rolled-back-in-the-head orgasms I’ve seen women have came from buttsecks. But for others, after a fully patient do everything right no pain attempt, it was a big, uh, this isn’t much fun and isn’t doing anything for me. Highly variable.
A lot of guys seem to get awfully hung up on it, certainly porn seems to be. Which is odd, because from the, uh, pitcher’s point of view, it actually is physically less stimulating; sure, a little tighter at first (but less and less so as the act goes on and things continue to relax), but it’s just an O, not a full contact grip like a vagina has. It’s the psych of the whole thing, really, not the sensation.
I only really get off on it when with a partner who is really getting off on it. That is pretty hott. But outside of that, there really isn’t much point.
Excellent advice, AAG. We have a vibe that’s about a half-inch thick we bought expressly for butt-lovin’, and that’s a good choice for anyone who wants to begin experimenting.
About half of all women love anal sex, and about half don’t. If you’re in the former group, rejoice and enjoy. If you find you fall into the latter group despite valiant efforts to enjoy it, no worries; there are lots of other things you can do to achieve total satisfaction in bed!
I loved buttsex with my ex, who had a tiny willy and was a very conscientious lover. My current bf, who will likely be the man i have buttsex with for the rest of my life, has a giant cock that makes my poor bum clench in terror. Because i really (really really) like buttsex I was eager to try it with current bf (who was also eager), but due to differences of scale I, um, tore. It wasn’t nice. And I was lubed up and rearing (pardon the pun) to go.
Any advice on how I can work myself to accommodate his girth?
CB, my experience in getting women ready often has included have them put in a butt plug for an hour or more before moving to direct play.. it helped them to relax and loosen up. Then have several dildos in graduated thicknesses to play with, so that you get more and more open. At some point you should be ready to take him in because your butt will have relaxed and opened up far more than you might have thought possible…. but it does take time.. so enjoy the butt fucking that way and if, on a given night, you don’t feel quite ready for him, no harm done as you will have had a great time anyway.
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Thanks for talking about this. I’m very curious about it and have only found very “clinical” descriptions. Not much of an inspiration. You’ve made buttsex sound really good!
The first time I tried buttsex, my ass rejected it. Big-time. I got the painful clench that didn’t release for a minute or more, and lost my horny.
My current partner and I have managed to coax my butt into submission. While fucking me from behind, he works a finger — or two, or three — in there until I’m ready for him. Then we switch fingers and cock. ;)
Thanks for the honest how-to, though — I could have used this a few years ago!
“I have yet to experience a feeling I’d describe as pain. Some people do. I’m just lucky, or have a high pain tolerance, or a slight degree of brain damage, or something.”
I could SO fall in love with you if I let myself :o)
I remember the time I decided I wanted to enjoy anal. The first time was very painful and didn’t actually happen, but then I spent the next couple of months, trying a little bit every day. It was a cold and wintery Iowa afternoon that I finally sank down on my toy and let out a very happy noise.
So, I agree completely with your post. :)
I wanna have butt-sex !!!!!! It feels so amazingly good done right !
oh for any of your male readers anal play can make your orgasms very very hard indeed…like in my case once in a while I’ll have my vision go dim and once I even lost consiousness for what seemed like forever but really was only a few seconds.
“If you’ve recently used your butt for its primary purpose”
That made me giggle like mad for some reason.
This was excellent advice. I had no trouble starting the butt-love, and was actually EMBARRASSED that my first behind-me-lover found it so easy. An ill-timed “Hey, this isn’t too tight at all!” comment from a man is BAD.
aag- this post was marvelous. it was educational and offered some laughs. you are so right about both partners needing to be interested in it if it is going ot happen and happen right. i have gotten into this recently and enjoy it immensely. sometimes, it works and sometimes not…i think i get a bit stressed and then it becomes an exit only. all you need is a conscientious lover willing to try again. thanks aag.
What a lovely treatment of something I’ve played around, and judging by my stats, several other guys are also into! And not just on the giving end of it.
The aneros that I’ve written about has a rather large handle, suitable for some play but not for walking around in or sitting on. It’s the champ of prostate massage although I have yet to master it. Butt you inspire me.
I’ve always liked your posts along this line.
D.
“Romance your ass. Woo your ass.”
That’s one of those lines for which I just want to hug you to pieces. You always make my day in one way or another!
You kind of make taking a big one up the ol’ keister sound like WAY too much work here, though. All I usually need are a couple shots of whiskey and a bullet to bite.
No, seriously, all it takes is for me to remember to try to push out while he’s pushing in and to remind him to give me a few good pumps with half of his cock before slapping his balls off mine.
:) Well, this was primarily directed at those who want to do the butt-luvin’ thing but have some degree of trepidation.
Not for experienced ass-lovers such as yourself, Joe.
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Hey, if anyone has trouble leaving a comment, let me know, willya? There seems to be an issue.
Lord don’t I hate issues.
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Really funny and insightful article!
New to anal here, but liking it. I found the friction at the anus to be the most exhilirating part! There was also the pressing of my partner’s legs against my buttocks and a feeling of fullness near the back of my vagina which was really lovely. Not much clitoral stimulation here – but always loved rear-entry vaginal so this is quite the experience.
My friend sent me this page for a laugh after doing research for something she was writing. But eventually, your little “tutorial” made me so curious about it that I decided to actually give it a go. I didn’t think I’d enjoy it at all, but I did! Holy wow. I definitely wasn’t expecting that.
Anyway I guess all I really wanted to say was thanks for the advice! I know I wouldn’t have enjoyed it half as much if I’d just taken a running leap at it (metaphorically of course). I’m glad someone out there is willing to talk openly and helpfully about stuff like this! Thank you again!
My buttcheeks contracted involuntarily when I read “running leap.” I’m glad you enjoyed it.
Btw, what was your friend writing about that she needed to research here? ::puzzled::
She was writing a story about a gay couple. LOL