Request for advice (very NSFF)

NSFF = Not Safe For Friends. Which means Melearlin, no reading this. Andyl, you too.

No, seriously.

I warned you!

Go away!

Okay, hopefully this is enough of a warning? Blum 3

My boyfriend wants to try anal sex and I'm not averse (in large part because the book convinced me it is not a scary-evil thing, so thanks MeiLin? In an odd sort of way? :D) except when we tried it hurt so badly we had to stop. Owburnowburnow. Suggestions on how to keep this from happening...?

Forums: 
Gudy's picture

Embodiment

... as far as I can see: lube and relaxation.

OK, first, I'm gonna assume in the following that he wants to put his dick into you. If the reverse is true, that doesn't change the substance of anything, just switch pronouns as necessary.

So, lube. You want something slippery with a bit of staying power. Thin water-based lubes are slippery but don't usually cut it in the staying power department. Use a thick, water-based lube (there are lubes specifically formulated for anal play), or a good silicone lube, or - if you're not using a latex-based barrier method for birth control and protection - even something oil-based. Absolutely stay away from anything that looks like it might contain a numbing agent or hints in any way, shape or form of making things less painful. You want to know when things go wrong, after all. I'm partial to silicone-based lubes myself (slippery and lots of staying power, cleanup can be a bit of work, though).

How much? While I know people who do without, the usual advice is that too much is almost enough. My experience is that yes, you want quite a bit of lube, certainly more than for vaginal play. Slather it on both your parts and his. If it looks like you have enough (or even too much), use some more, and try to get some inside of you, too (fingers or a syringe without a needle).

Relaxation. You need to be relaxed, physically and mentally. Being really aroused is good too. If you aren't, it probably ain't gonna work, at least not without being painful. If orgasms relax you, having had a couple of those before you proceed to the anal part of the evening may not be such a bad idea. Mentally, stress is bad, and not really wanting to have your ass penetrated and just going along with your boyfriend's wishes is, too. That may very well mean that you guys first need to do some preliminary play (kissing, tonging, fingers both inside and out) while giving you lots of orgasms in order to get your brain to make a link between pleasure and your butt. Also, you want your butt to get slowly used to not being a one way street any more, so start small. Fingers are always on hand. Start with one, work up to more. Be patient. Using latex gloves can make things more slippery due to the smooth surface they provide. If nothing more than that happens for a couple of weeks, that's perfectly OK.

Physically, find a position that works for you - doggy style, cowgirl, missionary, whatever is the most comfortable for you. Cowgirl/woman on top gives you all the control, but relaxation can be harder, while doggy style, especially with the head down is often better for relaxing the pelvic floor but leaves you with less control. Have a couple pillows on hand to adjust the angle if necessary. Start slow and small using tongue and fingers, then work your way up using dildos or more fingers until your butt is used to things that are at least as big as his dick.

Always go slow, especially with his dick. If it hurts, stop what you're doing but don't necessarily withdraw. Relax, try to figure out what's wrong (not enough lube, wrong angle, not relaxed enough, whatever) and fix things before continuing.

I know this sounds like a big production, but it does get easier if you do it with some regularity and your butt gets used to the shenanigans. Good luck, report back with the results }:) and above all, have fun!

ETA: typos, some minor clarifications

Amy's picture

Supplicant

Everything Gudy says is totally correct. I find on other bit of advise works well in conjunction with all of the above. Always make sure your bowels are empty before you try any kind of anal play.

If you have no room for fun parts to go it will make things a lot more painful & a lot less fun.

For beginners it's usually best if his first few penetrations of your anus with his penis is done from what ever position keeps as everything evenly lined up as possible. Hope you have lots of fun & enjoy the new way to play.

Swedgin's picture

bowels. If you know company is coming over always make sure to clean out your basement. And have your BF start with toys. It should give him a better, up close, view of how lubricated you have to be and how slowly he should go. Starting with toys also means all of his focus is spent making sure the insertion is comfortable, and how you respond to it, instead of his lizard brain taking over because he is getting to 5th base so he has to get there now.

Cheez-It's picture

...and try starting small, perhaps the index finger during normal sex or even a small vibrator.

Tigger's picture

Supplicant

but I find that doggy actually gives me more control. That could have more to do with my husband, but...yeah. He can hold perfectly still (when he tries very hard) and let me do the "work". I also find that going very, very slowly is helpful - just a little bit at a time, stop and pause in between to let my body adjust. And I can't stress the lube that Gudy was talking about. It might seem overly slippery, but believe me - it's WAY better to have too much than not enough. Amy also has a good point about making sure you are "empty". Consider how the body works, and that your anus is designed to be a one way street. Things can get "compacted" if you're not careful, which can cause all sorts of problems later.

Good luck with this! Like Gudy said, relax. I know it's difficult, but important. Smile

PS All puns were unintended...

Kittae's picture

Postulant

Thank you so much for making this topic and getting all these answers already! The book inspired me as well, but I had a -very- bad experience in the past and so I tense up real bad even thinking about anal sex in a personal sense sometimes. But me and my current SO moved past it slowly and it turned out great.

Something's stuck in my head again lately, and I tense up and get afraid again for no good reason. Then by the time we get all relaxed the lube has run out. So I'll definitely try this silicone-based lube idea. I didn't really know what it was for except for toys from reading Carnal Nation's stuff.

Thanks, everyone, for making my (our) sex better!

Gudy's picture

Embodiment

... it just stays slippery for ever, doesn't dry out or get cold (no evaporation), and does not irritate my wife's sensitive skin (she frequently had a burning sensation after we used different water-based lubes. Also, while it is more expensive, a small bottle lasts forever because you need way less of it than with water-based lubes.

Just about the only down side (apart from the fact that it's a bit harder to wash off than water- or oil-based lubes), is that it can attack lower grade silicone toys (dildos, vibes).

Blue Coyote's picture

Devotee

Savage love written by Dan Savage is also great for the sex-advice, and since he's gay he does know a little about it(and boy does he like to talk about it). Can be found online in The Onion or The Stranger.
Only extra piece of advice to add is "Towels are your friends". We keep a drawer full of little white towels on each side of the bed, dedicated sex towels that can be bleached. This is just something we do in general (to save the sheets) and is doubly true (and a good idea to double up the towels to sop up lube and Santorum) when doing anal.

Laureril's picture

Supplicant

Towels come in handy around certain times of the month too, or if you're interested in facials or what have you. Consider also having some hand sanitizer (for when you're done - it can irritate sensitive spots) to keep various ickies at bay.

kawaiikune's picture

Embodiment

I could get away with little towels. I keep a stack of giant towels near the bed, because we've been known to soak through them if they're not folded over enough times.

Amy's picture

Supplicant

to keep something by the bed dedicated to such things. I don't usually need towels, but I do keep a drawer filled with Cheep wash-cloths that are used for sex, that time of the month, & other things. I have two beach towels that I keep on hand for when I know things are likely to get very messy. Diaper pins help hold towels in place on the bed, very nicely I have found.

Stormy's picture

Supplicant

we have found that the one that works best for us is actually basically spooning with penetration. Also, standing in the shower works surprisingly well. Getting relaxed enough while standing can be a problem, but things definitely get and stay slippery.

Definitely get creative to find what works best for you. Positions that do not work with vaginal sex can actually work really well for anal.

NorthwoodsMan's picture

Embodiment

Well look who's back...

She shows us her chicken and disappears...

Amy's picture

Supplicant

That was a very banal joke if ever I saw one. Biggrin :whistle:

Stormy's picture

Supplicant

sorry 'bout that. "real" life got in the way of my online life. WTF is that about, right?! Anyway, I got massively behind on all my RSS subscriptions and have been waiting to catch up to start commenting again. It's only natural that my first one would be regarding subtext... Angel

Andyl's picture

Embodiment

*giggles at Marri*

Now, why didn't you want me reading that? Angel

Also, I probably wouldn't even have noticed it was you posting, if not for that warning. :bigsmile:

Gudy gave good advice, so I'd just add one thing - it was always a bit uncomfortable for me first going in, but touching yourself (especially the clitoris) can do wonders to alleviate that discomfort. Wink

Marri's picture

Supplicant

It was more for Melearlin, since she (unlike you) knows both the people in question, so even if it's a subject she's okay with in theory it's probably not something she wants to know / think about in specific relation to me and my boy. Biggrin

raecchi's picture

Devotee

If you can manage it, having the gal on top for the first time can be a good idea. It puts her entirely in control, which can ease the mental discomfort as well as the physical. The only downside is that it can be a bit awkward, especially if you're very lubed up.

My other suggestion is to get a small butt plug -- I recommend silicone or pyrex toys, for cleaning ease -- and try that while you have vaginal sex. The feeling is incredible, and it can be a good prelude to anal sex. The plug will help stretch you a bit, and if you get off during sex, you'll probably be a bit more relaxed. Have fun!

GreenGlass's picture

Supplicant

In real world experience, anal sex works out if you aim to follow the very good advice above. But yeah, it can still be uncomfortable in the heat of the moment, no matter how much both parties want it to be a good experience. From more earthy experience, yeah, even when you're aroused, the burning can really be a bitch. I've just taken the discomfort because it doesn't last long, lol. I'm planning to try enemas next. If they're quick and easy, I think I'll be pushing for it's use the next time it starts heading in that direction.

May I emphasize to you, to drill into your boy, SLOW going in! If the position IS wrong, it usually hurts badly enough that the venture is over, buddy. And if you go despite the pain, past it... I may just have been sick, but I blacked out in the shower once. So no matter how in the moment it is, there is indeed potential for messing it up big time, so he better channel that desire into making it as easy for you as possible!

kawaiikune's picture

Embodiment

For everyone who talked about silicone-based lubes (or other recommended lubes) up above, can you indicate a good brand?

For me, with anal sex, I slather the insides of the ass cheeks where you could have chafing, the asshole itself, and the dick, dildo or finger, with KY (which stays on it very well), and then I drizzle everything in astroglide. I use a TON of lube. I always put down a towel first so that extra lube can drip all over the place and I don't have to worry about it.

There are several different kinds of pain associated with ass play, and if you can figure out what it felt like, you can usually figure out what you're doing wrong. If you're doing everything right and you're experienced, putting things in your butt can lead to some of the best orgasms you've ever had. So, pain and it's causes:
1) Burning. Burning means you haven't used enough lube. If it burns like hell, have pull out whatever is in you, and add more KY, topping with astroglide. It could also be #3.
2) Internal aching (like a stomach ache, nausea, etc). This could mean a bad angle (so try to adjust a little), but if it continues, this means you probably have to poop, and you didn't. Pull out, go poop, wash everything really well, and try again. If you're getting into ass play, consider thinking about your diet. Do you eat enough fiber?
3) Owowowowowowowow!!! Especially if he feels like he's applying a lot of pressure to get something in there, you need to start with something smaller and work your way up. You're probably not relaxed enough (because you probably haven't figured out how to relax that part of your body independently yet). This leads to the thing that was the most important for me, when i was getting into ass play.

Practice! When you're in the shower, touch yourself there, or take some time by yourself. Try slipping a soapy fingertip just inside yourself in the shower, or use some astroglide outside the shower. When you do, you'll hit a point, as you insert the fingertip, that reflexively makes you clench up, and you'll feel it. Ass-muscles are really strong, so you can't really miss it. As soon as you feel yourself clench, stop moving your finger immediately. Don't pull it out, just leave it exactly where it is. Then try to relax the muscles that are clenching down on your finger. Once they relax, move again. Practice when you masturbate, (and if you don't masturbate, start!) and practice in the shower. Try to figure out what makes it take longer for you to clench up and what helps you relax. Maybe playing with your clit first will help. Maybe rubbing yourself all around the hole with a lot of lube first will help. I usually rub around the hole a lot and slowly, very slowly, work my way closer to the clenching spot. You should be able to get to the point where you can feel the finger hit the point where you would clench, and you think sexy enough thoughts that you are so relaxed that it doesn't. It will probably take some practice, and some time by yourself. Only have anal sex when you're in a good, warm, relaxed, trusting mood. Use lots of lube, start with your fingers, move onto his fingers, move on to a toy, and make sure he understands that it may be a while before you can relax enough to actually put his dick in there.

Once you are comfortable with putting things in there, when you actually go to have anal sex, it helps if you put something smaller in directly before you move on to something bigger. When I have anal sex, I usually start with a gloved finger (I keep a box of latex gloves and a stack of towels next to the bed), work my way up to a vibrating bullet or dildo, and then move up to a dick. This loosens me up in the moment, and helps me get into a more relaxed state of mind regarding my ass.

One final tip: if you don't have one of those vibrating bullets, get one! Vibrating bullets are great for your ass for several reasons. One, they are usually a little rounded plastic thing on the end of an electrical cord. This means that they meet the requirements for going in your ass: they can't get lost up there. Never use a dildo in your ass that doesn't have a flange, or a cord connected to something that won't get sucked in too. That will be one embarrassing trip to the emergency room. Two, they are usually a little rounded plastic thing on the end of an electrical cord. That means that you can get used to (and enjoy!) having something in your ass without the uncomfortable part: dealing with the sphincter. When you have a dick or dildo in your ass, it holds your sphincter open, which is the source of most of the discomfort that newbies to ass play report. This vibrating bullet can motivate you to get better at ass play by demonstrating how incredible it feels and how much harder you come with something moving around in your ass. Three, they're usually not too big, and they often come in "extremely tiny" and "still pretty small", so they're good for beginners to "Putting Things in Your Butt 101". Four, it vibrates. Need I say more? I can't recommend them more highly. One thing to note, however: they are made of plastic. This means that they can't be multi-purpose. If you put it in your butt, you can't put it anywhere else, because plastic is porous, and cannot be dishwashed or boiled, which means it can't be sanitized as thoroughly as glass. I use a condom with mine, but I hold onto the condom at all times, so it doesn't get sucked in and lost forever in the void. They have them at The Lover's Temple riiiiight here

So, that's all the advice I had. As a girl who was very ass-shy at one point, that's the best advice I can give you from experience. Hope it helps Smile Happy ass-fucking!
(...ahhh, phrases you almost never get to say)

judisheshok's picture

Postulant

That, I think, depends on the crowd you're in...lol Smile

Gudy's picture

Embodiment

... right there. I very much agree with all of it.

kawaiikune wrote:
For everyone who talked about silicone-based lubes (or other recommended lubes) up above, can you indicate a good brand?

We're using Pjur, and we're quite happy with it, to the point where we've essentially stopped using anything else. I'd recommend Pjur Basic or Pjur Original. I advise you to stay away from their Performance line - my warning above about numbing agents seems to apply for some of those.

Their DropStop tubes are great for not leaving a mess, but only if you don't need much lube (vaginal play). It's hard to get more substantial amounts of lube out of those tubes, especially when your fingers are already slippery.

blwinteler's picture

Supplicant

Don't really have much to add, except that it does get easier over time. The first time I had vaginal sex I ended up a little sore, same with anal. Like everyone said, use lots of lube, start small, go slow at first. And I definitely recommend raecchi's suggestion of using a toy there while having vaginal sex. It really does feel amazing, and is a good start for associating good feelings with anal sex, which means you will relax more later. I also enjoy the other way around, using a toy vaginally during anal. There is lots of fun to be had once you are comfortable Smile

Trillian's picture

Keep in mind that the larger HE is... The more you need to prep yourself. The first time I had anal it hurt so bad we stopped, fooled arond elsewhere, then went back a bit more slowly. Having him not quite full mast helps too. He has a bit more give, while still being hard enough to get in. Too flacid is a problem though. Just really dont get upset if it is slow going. Better slow and eventually awesome, then painful and avoided.

attercob's picture

Petitioner

Even more important than lube is that you be turned on. If you're hot then the sensations will be pleasure. If you're not into it then everything will hurt even with a ton of lube.

I find that eating my wife out while she lays on her back and making a point to let a lot of slobber get down to her asshole works well. She gets turned on and the slobber is enough lube to get fingers in her ass. Then move up to a smallish toy in the ass while continuing the oral sex. Then a toy that's bigger and about the size of my dick. Then lube up my dick with silicone and swap it in for the toy.

BTW, don't let him give you an orgasm from the oral until after the anal sex. You want to stay hot.

NorthwoodsMan's picture

Embodiment

nuff said...

Raigne's picture
Gudy's picture
NorthwoodsMan's picture

Embodiment

trust or have experianced?

Gudy's picture

Embodiment

... you seem to think. I certainly believe her when she says that multiple orgasms aren't for everyone, or by implication for her. Plus, my own experience supports her assertion since my wife doesn't do multiples, either. Clitoral orgasms cause a refractory period in her, just like orgasms usually cause a refractory period in men. G-spot orgasms, when we can make them happen, aren't so much multiple as they are one long, continuous, orgasmic state.

NorthwoodsMan's picture

Embodiment

Don't think I've heard of a refractory period in a woman before. Certainly time between one and the next, but not something that has required a break, fresh lube, or etc. While I suppose that the not orgasim time could be the refractory period.

I've found that it takes quite a while to get a G-spot orgasim achieved and usually requiries some clitoral stimulation along the way. But when it has been, it goes, and goes, and goes.

Raigne's picture

Embodiment

I'm done. I could probably be ready again in about twenty minutes to a half an hour, if I have some motivation.

I have also never had a g-spot orgasm.

attercob's picture

Petitioner

Even if you do multiples, I suggest holding staying on the edge if you're about to try anal. You want that "omg give me more, damnit" feeling when the dick goes up your ass. Once you have it in and are happy with it being there then you can have as many orgasms as you like.

Regarding multiples, in my experience it varies a lot person to person. For example, my wife's clit gets too sensitive for about 15 minutes after an clitoral orgasm, but vaginal/g-spot simulation is still productive. In contrast, on of my friends will have multiple clit orgasms one after the other until she pretty much passes out, but she pretty much never has a vag orgams no matter what I try. People are different.

Amy's picture

Supplicant

Are different simple as that. not only in how many orgasms they can have but in recovery time too. I happen to be very multi but if I've been stimulated for too long before I'm brought over at all then I will need recovery. I generally stay stay lubbed naturally, a little water may be needed vaginally but nothing else. & slobber is usually enough for anal sex too.

The G spot is so difficult to achieve because it's not just "A" spot. Think, neck, arms, breasts, lips, thighs, fingers, massive stimulation to all these places make the G Spot easier to achieve.

Gudy's picture

Embodiment

... vary a lot. The reasons heavy G-spot play isn't a regular thing for us are that we have two small kids at home who are total time and energy drains, and G-spot play takes quite a bit more time than clitoral stimulation to get good results for us. Also, the intensity involved costs my wife a lot of energy that she just doesn't have right now. The G-spot itself being hard to find or difficult to get working is so not a problem for us: arouse the wife - there it is, ready to play. Smile Whole body stimulation certainly makes it better, in fact it makes everything better. But in a pinch, or out of it, cunnilingus and a bit of G-spot stimulation are always a winning combination.

I am kinda envious of your self-lubrication, though. Pretty much any kind of penetration, regardless of her level of arousal, size of object or orifice involved, requires lube for us, and spit alone usually doesn't cut it. Makes spontaneous sex rather difficult. Sad

attercob's picture

Petitioner

spit is a really good lube.... I have a lot of trouble imagining vaginal penetration that would require more that spit, particularly if the woman has had children. I suppose anything is possible, but I have to wonder if you're just not being "sloppy" enough with the slobber?

I'd offer to demonstrate, but that would pose certain logistical challenges. Wink

Gudy's picture

Embodiment

... during cunnilingus. It's not enough, though, because I (and her) draw the line at opening her up and spitting into her vagina. So while her pubes can be covered in plenty of slobber, her vagina is still too dry for more than a finger. And once you have the need to add more lube to your dick anyway, using a purpose-made product like silicone lube takes about the same effort as hawking up more spit, but with vastly more reliable and consistent results regarding the reduction of friction.

And as for having had two children tunnel through the area, contrary to popular opinion that hasn't had any appreciable effect on the looseness or lubricity of the tunnel involved.

Velvetackbar's picture

Most High

Hrm...

Anyone that offers to spit into my asshole is going to at LEAST buy me a drink first Wink

Seriously: When doing anal play, you want to:

1. Make sure the field is clear. No players on the field. erm. If you have to ask "what players?" then you need to stop considering anal play.

2. Slippery, Slippery, Slippery. Think "stacking" lubes: water based KY or jelly lube with J-Lube powder or KLube. I know a few folks that stack silicone and ky. I don't like astroglide for anything but jacking off. It has an acidic quality that irritates my anal lining. Get a tiny spray bottle at the dollar store, and keep it by your bedside. A quick spray and suddenly all is again slippery.

3. Barrier protection: gloves keep hangnails from catching, and condoms keep you (or your partner) safer. Use them. If you play with lots of folks, keep "dry" condoms onhand for toys that might be shared, anally, and consider using polyeurethane gloves.

4. While "poppers" are fun, keep in mind that in men, that same vascular expansion will make erections difficult for 15 or so mins. Also keep in mind that the person who does poppers while playing anally will have reduced pain sensation: they may not know it hurts until it REALLY hurts. Bad Juju. Use at your own risk.

5. Relax: Safety precautions will help you do just that. a glove shows a partner cares. A lot of lube makes it FUN. dry lube is like having a piece of wood shoved up your ass. Not fun.

6. PUSH! Seriously...pushing out flexes the sphincter muscle, allowing it to be opened, and stretched out.

MalachiGuest's picture

My S/O and I have had great results with AstroGlide. It was recommended to me by a very good gay male friend of mine, so I figure he knew what he was talking about. He did, and it works great. Another thing that I don't think I saw mentioned here is that when you're warming up, it helps (assuming you're empty downstairs) if you push as if you were trying to poop. Just a little, just enough to get the sphincter to start opening up. This will make it easier for your partner to get a finger/toy/penis inside just a bit, and then when you stop, it will get drawn in by your contracting sphincter. From there, it's a slow process of getting everything loosened up, stretched out, and finally put in. Take it slow, take your time. If the guy wants to rush it and just get inside, then he's the wrong guy to let inside.

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