Bf wants to do buttstuff

I told him, before we first started having sex that I've never done that and am not interested in that. However he's been mentioning that he'd like to do anal occasionally. If I were to let him, should I do anything to prepare properly to minimize any potential mess? Is it gonna be painful?

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You should take an enema. It won't hurt if you're relaxed, but given it's your first time that may be tough. Use lots of lube also.

Prepare for your boyfriend to leave you for a man. That will be the most painful part.

>female
>ass
This is gay to you?

start with a plug. make sure he knows to go slow, and rim/massage for a while first. if he pisses you off just push all the poop out of your butthole while you have sex and he will probably stop asking

jfc

>You should take an enema
Unnecessary.
>It won't hurt if you're relaxed
Untrue
>Use lots of lube also.
At least that's correct.

Don't listen to zoomers OP. From an adult man who has done anal with multiple different partners:
1) Use lube, that's point number 1
2) You know if you have a shit on deck, don't do anal then. If you go relieve yourself like 20 minutes before hand and then actually wash up (wet wipes or shower) then you're 100% fine. A dick isn't going THAT far in.
3) Be. On. Your. Back. Lifted legs, while you're on your back straights the rectum and prevents pushing up against the turn that's like 3 inches in. This is EASILY the most comfortable position for the one receiving.
4) The receiver is in control. Once he gets the tip in, he stays absolutely still and you push yourself back and forth, probably bracing hands above your head against a wall. This lets you ease into it and prevents anything from hurting
5) It WILL sting every time, right at first. However, don't panic. If you panic and clench up it will actually hurt. If you think of it like... like picking at your gums with a toothpick. Like it hurts right at first, but if you keep doing it your body eases up. Relax, and go slow and it will stop hurting.
6) You can definitely cum this way and I'm told it's a much slower "deeper" orgasm for women. Like less of a climactic explosion and more like a rising tide. I dunno, the words don't always translate to me, but that's the language the women I've been with have used.

It's completely possible to have a positive first anal experience, you just have to not think it works like porn presents it.

>unnecessary
Maybe, but it helps clean you out. Reduces chances of him coming across something.
>Untrue
Pretty much true, if she's not relaxed it WILL hurt. First time probably always does a little, but if properly relaxed it won't really hurt with subsequent tries. A lot of proper foreplay helps in that.
>At least that's correct.
I know, thanks. I'm gen Y also, no Z.

>Maybe
It's a barrier to entry. An enema isn't a super easy hassle free procedure and thinking it's necessary is just going to dissuade people from trying anal. Yes, you're right it DOES reduce the chance of a small spec of feces being present. Is it more trouble than it's worth for new-comers? 99/100 yes.

>if she's not relaxed it WILL hurt
Perhaps I was unclear. If you're not relaxed it will hurt yes, but even if you are relaxed it will still sting at first. If you tell people "Relax and it won't hurt" they're going to try it, be relaxed, still feel the sting, think something is wrong (like they're not relaxed ENOUGH) and they're going to clench up and panic.

It WILL sting no matter how relaxed she is, but if she _stays_ relaxed, that pain will go away. That was the important take away.

Yeah that's fair. You make a good point about the position anyway. My ex wanted anal from time to time, I was actually the one that cared less for it. Just felt a lot less easy and eventful than just having regular sex. Porn definitely made anal seem more appealing than it actually is, at least to me.

Anal isn't at the spur of the moment activity.
I've been doing buttstuff for a couple years now.

First, start taking metamucil. It'll make your shits come out much easier, which will anal much cleaner and more pleasant.

Second, you need to start training your ass.
Not just stretching it out, but also teaching your rectum to get used to having something going in the wrong way.
If your ass isn't comfortable and you tense up, it will be very, very painful. For you.

Get some nice lube, water based will work, but if you want you can try silicone. Silicone is a bit messier since it doesn't dry up like water based, but it lasts longer. Also remember that there is no such thing as too much lube.

Start training with your ass with your finger. Start with teasing your asshole, you'll feel it pucker.
Keep teasing it until it stops puckering to your touch. Then start trying to penetrate. Be slow and gentle, and above all else, be relaxed. Having your asshole and rectum relaxed isn't optional. You know your body best, if you feel your ass wanting to reject your finger, just stop, concentrate on relaxing, then push in deeper. Rinse and repeat until you've got your entire finger in there.
Once you're in, you can start trying to finger fuck your ass, just remember to stop when you feel yourself trying to shit your finger out.

Keep training yourself with your finger and you should get used to it fairly quickly. Getting used to your finger or two should take less than a week

After your finger, you can try start using toys.
I'd suggest buying dildos, specifically soft, flexible dildos, hard dildos and objects aren't pleasant imo.
When you buy a dildo, make sure it has a flared base otherwise your asshole could eat it. I heard that if your ass eats a small dildo, you can shit it out. But I never tempted fate.
Train your ass similar to how you did with your fingers. Remember to stop when you feel yourself trying to shit the dildo back out.

At some point during training, you're going to feel like you're going to shit yourself while your ass is stuffed. As long as you shit before hand, you should be fine.

When the time comes, remember to plan anal around your poo cycle, not your poo cycle around anal.
Wait until your body tells you you're ready to take a shit. If you force it, it'll be harder to get all of it out and you might end up pinching a nugget in there.
After you shit, let your boyfriend know to be ready to fuck in 30 minutes. Use this time to take a shower and if you want, have an enema. I never do it because it fucks up your bacterial ecosystem. If you've been taking metamucil then your ass should be relatively clean.

When you finally get to it, you need to communicate a lot, your boyfriend doesn't know what you're feeling, so it's up to you to tell him how slowly he can go in, when to stop, and what tempo to fuck you.

I’m saying this as a male. Be firm in your beliefs. Sexual compatibility is part of a relationship. If you have him the heads up before dating and he’s starting to pressure you he’s putting his own sexual interests over your comfort.

Also, anal sex is fucking gross. The anus is not a sexual organ and shouldn’t be used as one. And it’s extremely painful. For you.

If he really wants to do butt stuff, make him rim you first

>Also, anal sex is fucking gross. The anus is not a sexual organ and shouldn’t be used as one. And it’s extremely painful. For you.
It is what I told him beforehand and he said ok. But he mentions it sometimes. Few times when we had sex I felt like I could maybe let him do it and it wouldn't be so bad, however that might just be the heat of the moment doing the thinking for me.

1) if you don't want to perform a sex act with your boyfriend, it's totally fine and he should respect that
2) anal sex isn't really that gross. My girlfriend and I clean up in the shower together before anal play on both our ends (I penetrate, but I also enjoy it when she plays with me down there too. We both eat each other's asses). Both holes have secretions, and both are very clean if you know what you're doing. Vaginal pleasure and anal pleasure are two types of things that are probably worth exploring.

Remember, aside from penetrative sex and cumming deep, everything else in sex is social and extraneous. So don't convince yourself that anything like anal is anymore artificial than stripping naked to have sex, than sucking on boobs, or even kissing.

Yeah no don't do anything impulsive like that, better yet just don't try it at all. It's puts you both at risk for health problems and STDs. Overall it's not that great.

Anybody that advocates for anal sex either has some trauma they need to deal with or has had their mind corrupted by porn. Or worse yet been pursuaded into it by a partner that falls into either of those two categories. Again, don't. You already don't want to so be firm about it and close the lid on the discussion.

>Anybody that advocates for anal sex either has some trauma they need to deal with or has had their mind corrupted by porn
???
I think you're projecting mate. Anal sex is fine so long as you practice safe sex.

I take it you were convinced by an ex then. I'm so sorry...

I know this is shitposting, but not really. My girlfriend and I practice it regularly (like once a month or something). We're both well functioning members of society (she's an electrical engineer and I'm a physics grad student), we're sociable, etc. There's nothing "broken" about us.

>is it gonna be painful
for you

For sure. Have him lick your butt. You'll probably like that at least.

licking butts is unironically so much fun for everyone involved, especially if both partners reciprocate. I like licking my girlfriend's ass and then biting her asscheeks. It drives her nuts (and drives me nuts when she does it to me, too)

I'm genuinely not shitposting. You have to have something wrong with you to enjoy anal sex. I won't lie and say I haven't done it before but I was disgusted with the experience (and yes, she was clean and "ready").

>If I were to let him, should I do anything to prepare properly to minimize any potential mess? Is it gonna be painful?
Free Bargianing chip here gurl, take it and run with it. Ask for something you want.
Google anal prep, get a cheap silicone plug set, L2 Douche and Lube.
Yes it will potentially be painful if you don't work up to his size.

Some people have the ability to stimulate Gspots with anal based on a biological difference. People get built differently. Missionary isn't a solve all either.

We call those biological disorders.

Femanon here - DO NOT start with anal sex. DO NOT let him train you with his dick. Get a soft dildo or beads - Bad Dragon HIGHLY recommended in medium or soft consistency. With beads start out small, USE LUBE I cannot stress that enough. You should masturbate and use a small plug/ beads/ Bad Dragon on yourself so you can relax. It is so much easier to train yourself if your clit is being stimulated. Try it on your own so you know that you can relax and what to expect in terms of "mess" honestly I've never had issues with making a mess during anal. But trust me on the toys and stimulation first, no starting with sex.

are you that dude that types whole paragraphs about how anal is bad on /gif/?? lol
also you're on Jow Forums so there must be something wrong with you too ya nignog

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shit on his dick

Came here for this.

Guys that want to do a woman in the ass are bisexual.

His brain has probably been warped by pornography like most men these days but then again so has mine and I've never been into anal sex.

Have an Orgasm first, it will be easier

Start with 1 finger and add more as you get used to it over time. Also use lots of lube. And don't forget the lube.

Do an enema before hand
Also to minimise pain buy a small butt plug and put it in your ass for 5-10 mins a couple of days leading up to it and you’ll be fine

No. Now go back to your tranny thread.

I don't watch porn, but thanks bud.

Right, you just visit /gif/ for educational purposes.

A finger in the bum?

tell him he needs to lick your butthole first

>my anecdotal experience generalizes into the truth, which is black and white
Now I know you’re projecting for sure