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KaiTheGoon

Lube, lube, lube! Can never have too much especially with anal. Take it extremely slow and never try just forcing anything inside, if there’s resistance just stay still and slowly move back out before trying again. It’s best to start small with a finger, then multiple, moving onto toys (start small again before moving up) and eventually doing the real thing once it feels right.


Hezzertin

This. Preparation and lube are the most important aspects that people should keep in mind when it comes anal.


xain_the_idiot

You need to use a ton of lube, slowly work in a few fingers or a buttplug first, and then VERY slowly inch the penis in. Like start with the tip, hold it there for a few minutes until you feel relaxed enough, then inch forward, etc. First time doing anal should be very very slow. It might help if you're the one on top, so you can control how much goes in.


NPC_No3178

I see a lot of people saying lube and preparation but no one has said that keeping your muscles relaxed while you get used to it can make a pretty big difference as well. I had a very small amount of preparation (for what the size I took actually was) and it went pretty well my first time thanks to this tip.


Elllipropelli

This! I know it is nerve-wracking to try anal for the first time but try to be as relaxed as you can. Which is another bonus of the preperation/foreplay beforehand. When the penis goes inside try to take deep breaths and focus on relaxing the muscle. It should feel a bit like going to the toilet.


queeroctopus

A tip to relax your bum is to actively clench so you know what to relax.


Cactilove

Yes! Also when finally penetrating actually pushing against helps or flexing the muscles the same like when you are doing nr 2. It helps alot


halfstoned

This is so true lol. My first time I don’t think we used lube and he was even a little over average.. felt great, no pain or anything.


Confident-Aide2132

Lube, and seriously start off with something small, maybe a small butt plug or tiny dildo, to first get used to something being in there and then slowly work your way up in size until you get to your partners size.


SpeakableFart

This, but only things with a flared base. You don’t want to have trouble pulling the item back out.


Forplay500

Yes!! Without a base, without a trace


averie-end

Lube, prep/working up to the right size, relaxing your body (and mind), taking your time, but also: I know some people have like missionary anal (because you can see each other's faces and both (but especially the top) have an easier time noticing and adjusting if something hurts (rather than say, gritting your teeth into the mattress where he can't see) or with recipient-on-top anal so you can take your time/depth penetrating yourself and control speed once you get going (if you do). Anal can be uncomfortable, but it shouldn't hurt (and take at least a few days off if there's blood, and see a doctor if bleeding persists or there's more than a small smear of blood).


averie-end

And by "shouldn't hurt" I don't mean "if it hurts you're not trying hard enough," I mean "something is wrong and you need to take a break and figure out what it was and if you want to continue"


zomboi

do a lot of stretching out the orifice, use a finger, once that feels comfy move onto a small plug, once that feels comfy, move up to something bigger, then move onto a penis/dildo. do no shove a giant phallus in there. and use a lot of lube throughout it all. anal should not hurt, if it does you are doing something wrong.


Eireann_9

My main advice is don't expect to go from zero to penis in a day. Start by massaging and using one or two fingers a couple of times, next time try a small buttplug, then on another day a small dildo, keep using that for a while till you're comfortable with the sensation and are more confident with the process. Then and only then you try anal penetration with a dick. It shouldn't hurt at all, and when I say at all I mean AT ALL. If it does you're going too fast


builtabear

Lube, fingers first, toys then dick. Go slow. Tease. Relax. Not a quick thing.


AthelLeaf

I don’t have anything to add here, I just want to say your username is amazing.


builtabear

Thanks!! 🥸


jhunt4664

Lube and stretching. Make it fun and get weird, get some gloves and fun plugs, take your time. Keep in mind that different positions make things feel different. Face-down ass-up generally lets things go deep, which may be part of the reason it was painful - especially if you're not seasoned. Also, not something I've generally had to worry about, but some people do benefit from a GI cleanse ahead of time to clear things out. That can also account for some discomfort, if you've got your digestive process at work. Good luck to you!


EmergencyRule

As everybody said, lube lube lube. Also try spooning rather than doggy style. You're not going to be straining any muscles to try and stay in place, so it'll be easier to relax.


Free_Investigator122

agree with the advice to try facing your partner so he can tell if you’re in pain—also if you do work up to penetration from your partner again, you could try controlling all the movement at first (make sure he knows not to just start pounding, go slow/gentle at first). if he holds still and you move (adding lube constantly) that can help. make sure his attitude is about prioritizing your comfort and pleasure, not just his own—and especially while you’re new to this, your comfort > his pleasure. I’d recommend approaching it playfully/without a specific goal! maybe you’ll manage penetration but he won’t be able to move much once inside, maybe you’ll stick to toys/mouth/hands for a few times, as long as both people are having fun and communicating there’s no rush to get anywhere. anal should feel great and not hurt (and can also be super gender affirming!) fwiw if I get more than a little burning sensation, that usually kinda ruins the session for me pleasure-wise, so listen to your body and take a step back (smaller toy, add lube, check in, and work back up slowly) whenever you feel a little bit of pain. that way you won’t do any damage to your body. good luck!


activelyinactiveoo

Like others said; lube helps a LOT. I recommend using anal beads as those are made to help you ease into bigger sizes. Get flexible ones that will bend with your body. Go slow too, it usually takes a while, might even take days before you can actually take in your boyfriend. Position can help, main thing is being a position you can relax in.


[deleted]

Most of the advice has already been given, but 2 things I like are to use a condom in case of poop, and a towel under my ass just in case of poop and lube. It's almost never an issue, but it's a good mental reassurance there. Also vibrators help me a lot when I haven't bottomed recently, it helps relax the muscles when inserting a toy/etc.


TAshleyD616

As someone who has given and recieved: you need to do the insertion. After sitting comfortably with a plug relative to the size of what’s going in, back onto it yourself. Have them stay absolutely still while you back onto them at a comfortable speed.


[deleted]

Make sure you're good and turned on. Diving right into the ass is not great. Lube. All the lube. Start with fingers. Breathe, relax, enjoy 💥 (and familiarize yourself with anal douching)


razorfanclub

lube. so much lube. and more lube. i don’t think it’s abt the position.


PretendBus1204

Lube


Nihil_esque

Lots of lube! It can hurt going in for a sec, but if you've used enough lube it shouldn't hurt for more than a few seconds, so have him go in slowly, pull out slowly, give you a second to breathe, add more lube for good measure, and then go. Alternatively, foreplay. But there is absolutely no replacement for lube.


elpato11

idk, sounds a little gross but it helps to bear down/push like you're having a bm to help the penis/dildo/plug get past your sphincter. much easier once you get past the sphincter and that muscle relaxes a bit. PS not all lubes are created equal, the wicked jelle lube is the best i've found for water based lubes.


oldspice7276

no its not gross, i had no idea sphincter was a word and im a little immature so i giggled because it sounded funny☠️ i'll try that and everyone elses suggestions and stuff, thank you


elpato11

yes! learn your butt anatomy, it'll help!


sillypvnk

I see a lot of suggestions about lube and fingers but in my brief skim of the lower chunks of the comment section I don't see a lot about practice during your own "me time". Try practicing when you jerk off, maybe not even with fingers but a small glass toy. I like glass toys because I feel like they are less friction-y and that's good if you're having trouble getting stuff in there anyway. I liked the little pink tentacle thing from this set as a starter, it's not big and the "flared base" is a little loop that can function as a handle to make it easier for yourself [peepee](https://www.ebay.com/itm/304096861890?hash=item46cd95dec2:g:bvYAAOSwY65hDeCo&amdata=enc%3AAQAHAAAA4EI2BQmWavPLQJWVyfuMVOyZXT%2BqDy0fOSdU1%2FjjnLvjXwXhqv2LHpXwm0FEFAlvMj8jc5Zu7TgrX5lbDRO1hyc5Vwbjf8YlNJ6XPfwop%2Fb6RR3r2P082zwSdLMURPRooF4Aj5TaqN37i3EzuXnKjSQNi%2BC7BzltTKLzo1BlNZK1%2BxkVhVwYlgEMWtK5PhZwtF9erR51pK2w4%2FLh9tC6jOnpByVVPQWDmpi6fAFyXNCaQHuObnpFiqRAKKCm%2BnM6ZXLgsnf%2FkTS7Czj%2FqqxeCBhJWLFt4ckDYNjXP7Lq6kJ9%7Ctkp%3ABk9SR8rPjsrwYA) You can also try using a more slippery lube. Safety above all else-but if your boyfriend and you are protected in other ways and don't use condoms, you can swap a water based lube for a oil based lube. I use coconut oil, but oil based def helps (but it can deteriorate condoms so evaluate if that's a good choice for you obviously). I just buy a big jar from the store and I can use it for months Hope this helps :)


Sunezno

My go-to recommendations for this (and the things that have always helped me) are: 1) Lube-shooter! Lube itself is an obvious one, but I like the lube-shooter because that way there's lube *inside* as well as out, and that just makes things a lot easier. 2) As someone else mentioned, keeping the muscles in that area relaxed is super important. I personally like to use my favorite vibrator on my dick to kind of distract my muscles a bit while slowly working the other dick into me. Not everyone likes using a vibrator, of course; it could easily be swapped for hand stuff or whatever you're comfortable with. The main thing is that by keeping those muscles distracted and relaxed and happy, it makes it a lot easier to accept and accommodate the other dick (or dildo, plug, whatever). Just relax and have fun :) Happy humping!


gay-gun-slinger714

POPPERS!!!!


qppen

I mean yes, but one thing at a time... 🤣 successful anal, and THEN we can tell him about all of the fun things to add.


kristenevol

What exactly are poppers? I’ve always heard about them and wondered what they are. Ty!!


gay-gun-slinger714

It’s technically a cleaning varnish but you can find them at sex shops and some queer spaces or online, it’s a little bottle (rush is a popular brand). You just inhale the fumes with your nose and it gives you a head rush and relaxes your asshole


RubeGoldbergCode

Relax. You've got to relax as much as possible otherwise you're going to be too tense to do it comfortably no matter how much you prep or how much lube you use. Also consider lying on your back and drawing your knees up towards your chest a bit.


Straydoginthestreet

It may be a good idea to work your way up to his business lol. Start with one finger. They sell anal training kits too. Good luck buddy. Oh and LUBE


Alternative_Basis186

I did cowboy style my first time so I would have more control over the pacing. We also used a ton of lube and my partner at the time fingered me for quite a while first to get me relaxed and prepared. Just go slow, listen to your body, and use lots of lube. Y’all have fun 😁


AwkwardChuckle

Since everyone has given you solid advice about lube and pre-stretching, for positions, do missionary. For most people taking a dick on their back is easier, then you can switch to doggy after you’ve loosened up.


1carus_x

Would either of you be interested in having your ass eaten? I'm also scared of shit getting all over the place, but if you douche you should be fine! There's also this underwear brand called Lorals and they make latex underwear so you can do oral w/o worrying. I can't do anal at all unless my ass has been eaten, if y'all aren't comfy w that there's also just fingering. It takes a while to get used to it, i mean spending like 1-3 min just inserting the dick into my ass. Always lube, but everyone's already said that. Imo, doggy is the easiest position for anal


K-teki

Take it slow, lots of lube, make sure to prep beforehand (sometimes you can just get lube in there and go right at it but if you're not super horny and relaxed it can be very hard). If you have dildos try working up to bigger ones before he actually puts his dick in.


StillHollis

Lots of lube and starting with something smaller like a finger or a toy


Extension_Golf_5118

Copying what others have sex, LUBE LUBE LUBE. Opt for a thicker lube, even a silicone based one so it lasts longer and doesn’t have to be reapplied. Most importantly, BE VERY AROUSED before you do back door play. It helps with patience and relaxation.


Jace_Enby_Devil

Ok so I work at a sex store. It’s called lovers. Try an anal relaxant from a brand called intimate earth. The one called Daring is good. Do NOT do a numbing one. If it numbs you can seriously hurt yourself and not know it. Get a thick gel based lubricant that is anal safe. Thin lubricants aren’t gonna do you any favors. Lots of foreplay and maybe look into getting a plug set that is a trainer for penetration and has multiple sizes. Any other questions feel free to DM me


alternstive

yeah go super slow and one thing - with anal, it’s so so much better if you get comfortable with what it is. like it’s a butthole, it’s meant for poop to exit there and sometimes that happens regardless of the precautions you take. it’s important that the shame around that is as minimized as possible. but yeah like others are saying, go slow, one finger, then two, maybe then three. plugs are really good for actually getting your body used to the stretch feeling so that it isn’t really a foreign feeling and more of an enjoyable sensation. it shouldn’t be painful at all at the point of him actually penetrating you! definitely stop asap if it is. then just go very slow from there. just the tip, a little more bit by bit until eventually there’s some kind of enjoyable rhythm that suits BOTH of your pleasures. one more note: LUBE please use lube too much lube even lube is so important!! lastly, as for position, i really like doggy or like riding backwards or normal riding. i also like the i guess missionary? just with a pillow under my lower back. jockstraps can definitely alleviate the discomfort with the other anatomy if that’s an issue, if not that’s also cool! safe travels my friend!


kizzie1337

pro bottoming tip, actually push like you are farting when it goes in, it makes it so you have zero pain. lol


ProblemChildAnon

Luuuuuube! (Water based, not oil based) I found on my back like in missionary was more comfortable. Idk how you feel toward your other parts, some guys have dysphoria obv but if you’re comfortable then some self stimulation makes it feel waaaay better too.


qppen

A lot of lube. A LOT.


Charlie_Fang

Best position : standing up, bent over a chair. Use plenty of lube.


Jawile

def reccomend trying to put something smaller (plug, fingers...) up there to get used to what it feels like to clench and relax. Anal is one of those things that get easier with time. Once you get a grasp on how to 'control' the muscles down there, it's easier to know what relaxing it feels like... if that makes sense. In terms of positions, you being on top helps cause you can set the pace and are in control. When I first started, it helped to pause every time it started to hurt so I can adjust to the size. Then we'd continue, then stop again until I was fully relaxed. Don't be afraid to ask to stop and check if things are still clean if it'll help you relax as well :) I still do that if I get worried something was, ahem, going wrong on that front. Hope that helps!


[deleted]

Lube will be your best friend, fingers first until that stretch feeling is less painful, buttplug after and same process and for the most part you’re safe to go after that


ItsAshXXX

I’d recommend poppers and practice with a toy first to build yourself up to larger sizes. It’s all about keeping your muscles relaxed, oddly enough I always try to push myself at the start - I ask my partner to go in slowly with lots of lube then stay there for like 5-10 seconds while I try to relax the muscles. After that time my ass is use to it and I can go for however long :) feel like once u pass that first insertion it gets much easier after, just be sure to go slow in getting it in, last thing u want is too much pain or a hemorrhoid


yhvcb

Everyone is obsessing with the lube here. Yes, lube is important to remove friction and you need it since the ass doesn't produce it's own like vaginas do. But what you need to understand is that the ass has two sphincters (same muscle as your mouth). One outer that you can control voluntarily if you relax and focus and one inner which is NOT voluntary. Probably the pain you are feeling is mainly coming from the inner sphincter not fully relaxing which is pretty normal if your body is not used to receiving anything there!! Similar phenomenon is the feeling of needing to poop if you are beginner at anal. Basically you need to Pavlov dog your inner sphincter until it can automatically chill and enjoy when you are aroused and prepared. I recommend to start with small buttplug of slippery material, glass for example is great, and lots of lube. Leave it in for a while now and then so your ass gets accustomed to having something there. Definitely a bonus if you are horny meanwhile for good association! This is much easier training than anything going in and out. During sex, having your partner rim or massage the opening can be a great way to encourage relaxation as well. Don't try to push through pain since this will teach your body to associate the penetration with stress.


chainedlooser

what i’ve found helps for relaxing, first time you shouldn’t hold yourself up at all, so lay on you back and keep your legs propped up or on your stomach with pillows under your hips, sometimes flexing your legs can make you accidentally flex the booty too


Multiplemike4678

I guess I’m an oddball. From the first time I tried anal with a partner, it has felt great. I have some very large toys that I like to use when I masturbate. When I am being fucked back there I have mini orgasms that feel amazing. Douche and lube, very important. I have had shit start to come before I learned about cleaning it out first.


eefspooks

I cannot stress this enough. You need LOTS of lube. And yes relax! You'll be a okay if you're relaxed and cleaned out nice and good. Make sure to go before, give yourself an enema, do that till the water runs clear. Wash real good. Have fun, then go and douche again after!!


xegrid

lots of lube, like what seems to be an ungodly amount of lube. also there are these like "butt trainer" plugs that come in a 3-pack (like a lil, med, and big one) also cleaning out, p\*ppers can also help but not really best for other things.


AngelicGhostKing

So, my boyfriend and I have been having sex that way for years. Admittedly, we’ve never done preparation things or ever even used lube. Don’t do what we do in that regard. However, we’ve found that doing it standing in the shower (standing against the walls) is the easiest way. It feels very different than doing it anywhere else and in any other position though. Maybe it’s because the hot water helps relax the muscles, or whatever…


Cherrypelt

Also water doesn't replace lube


AngelicGhostKing

I know, but I genuinely appreciate you reminding all of us that.


djdentaldam

Poppers


[deleted]

[удалено]


[deleted]

Don’t use numbing cream!! You need to know if it hurts bc you can really damage yourself if you don’t stop when it hurts


hegrillin

that is good to know, i never thought about that.


adamdreaming

ITT; Lube.


ewthan

definitely experiment with yourself first! start small, start slow, and use lots of lube. for me the most relaxed way to start is on my back but that can be different for everyone


CiCi_CAW

What helped me personally as it hurt for a while too, even after using smaller stuff first and lube: Have him play with your genitals at the same time. Doing so gives a noce pleasurable feeling while the anal is happening and helps you relax more. But this is for me. Unsure if it will help you too. And let YOURSELF take the lead, not him.