Start with oral. Progress to licking her ass, rimming, sticking your tongue into her ass. Fucking her ass with your tongue. Some fingerings with one finger and lots of lube. Then two fingers. Small dildo… and so it goes.

Important: get her always very hot before starting to play with her ass: give her oral, edge her, finger her pussy simultaneously, lube on, don’t make her cum. You want her pussy needy, her clit swollen, begging for your touch. So, you move to her ass, but keep giving attention to her clit, edging, never letting her cum.

Just thinking of it now, I’m soaking wet in my pussy, very excited and willing to give my ass.

If I were a man, I wouldn’t ask for anal. I’d do the gradual building up I’ve described, so, if she didn’t want it, she’d have plenty of time to let me know and stop. Never force. Never. But you can introduce things slowly, in the most pleasant way possible, so that the person has the possibility to feel how good it is, before saying no.

Lots of women say no, because we always expect men to be brutes, and inept in bed. So, they give a preemptive no.

Source

sluttyanalwitch: I have a friend and she says the best birth control method is the use of condom. I disagree, however using condom is important of course. I’m pretty sure the best birth control method is having only anal sex.

that-shy-freak: Have you ever done anal?

rockergirl1979: LLLOOOVVVEEE it!!!

First time I had anal was April.21st and I haven’t looked back since. LoL It is the best way to be closest to your partner and for me I will cum 100 times harder than regular vaginal sex.
Feel free to ask anything else shy one ?

??

The problem with anal is that guys don’t know how to do it, not that women can’t enjoy it.

Yes, I am sure there are some women that no matter what you do they will never like it, and that’s fine.

But the average woman will go nuts for butt sex once she’s had her first anal orgasm, TRUST!

The key is to put her pleasure before your own. If you introduce anal stimulation during cunnilingus she can see that it adds to the pleasure. Analingus has always been the best way to introduce a backdoor virgin to anal imo.

The tongue is soft, warm, wet and non-threatening. Even a finger can seem scary to some girls. With your tongue on her clit and your finger in her ass you can take her to new levels of orgasm she’s never experienced.

After that, she will be BEGGING to see what an orgasm from a cock in the butt feels like! And even if it is a bit painful (usually at the entry when the head goes in) she will be more willing to try and relax through it knowing that pleasure is to come. But if she has not experience with anal pleasure, she will probably have not reason to persevere IF it’s painful.

But if ur doing your job right, it shouldn’t be.

Source

Anonymous: I’m new to this… I’m planning on altering my ass for my husband who works over seas. I was just wondering to you have any tips/tricks to help me?

alteredasses: Open it a little wider every time you train, always working up from the smallest to the largest toy during *each* session. If you don’t feel yourself gently pushing past your previous physical limit, you’re not going to get there. Use lots of lube, more than you planned on using. *Always* rub your clit while you stretch to help wire your brain to expect pleasure while your asshole is filled — there’s serious research backing that one up, and some really fun less-serious research too. Most importantly, remember to send pics here, maybe even to your hubby too. 😉

A young female reader of dearcupid.org asks:

recently by BF has taken to asking me to have anal sex, but i really dont know what to do here?

i dont really want to, but at the same time i am a bit curious. i want to know does it really hurt? does it feel better for him? is that why he want it.im not sure but there is just something that isnt quite right for me with someone putting something “up there”i know its up to me if i say yes, but what would justify me saying no?

Shrewd observers will notice that she closes the question by appealing for reasons that will justify to herself not trying anal sex. This is a subject in itself, which deserves addressing fully at another time.

Let us instead turn our attention on the “why does he want anal?”. Many wives or girlfriends are confused and don’t understand the motivation that their partner has. This can often lead to fear and uncertainty and a reluctance to try anal which can be damaging to the relationship. Only by communicating and exploring this aspects of their partners desire can they come to understand and possibly accommodate them.

It is important to realize that whatever you may have been told, there is no single reason why a man (or woman) will want anal. There may be just one reason, or a combination of reasons.

Some of the more common reasons are:

• They find anal sex more intimate.
• Anal sex provides more physical stimulation, so orgasm is more likely or stronger.
• Doing something different is mentally exciting.
• Prefer the look of the anus or buttocks.
• Are not aroused by vaginal sex or the vagina itself.

Rest assured, all these are all very normal and very common, though little reported. Millions of people around the world share these things in common, being a natural part of them just like any other aspect of their personality or genetic make-up.

After all, nobody is strange because they like blondes, or large breasts, so why worry if a person is attracted to the idea of anal sex? To do so would be irrational.

ironlion8: Is baby oil a good lube for anal? What would you recommend to a first time couple?

I would not suggest baby oil, no. Try a water based lube or silicone lube (don’t use silicone lubes with silicone sex toys, however—it will ruin them). A lot of people do like coconut oil.

The long winter is over. After 5 years without even one complete anal sex session (3 attempts, 2 barely count) my girlfriend and I finally broke the spell. She gave me her virgin ass for over an hour before her beautiful asshole gracefully extracted every last ounce of my cum. It’s already been a few days since we did it but my cock remains utterly entranced, desperately longing to once more re-enter its natural home. I want to go back but she is insisting that it should only be a “special” thing. She doesn’t understand that I /need/ more, and that It’s not that I don’t love her pussy. I do. I love her pussy and most of the other wonderful pussies i’ve encountered. But anal is my ambrosia and addiction. What’s more is that it’s also a way of life for me. Since highschool I have only ever looked at anal porn. Unfortunately I wasn’t able to find a girl who would let me have it more than once maybe twice a week tops. But like a vampire, I thirsted for more. And now after years of patiently waiting I finally got an overwhelming taste of what it’s like to act on my thoughts. I emptied half a fucking bottle of baby oil on her ass while I fucked her from behind, missionary anal, and finally mesmerizing reverse cowgirl anal that literally made the hair on my neck stand up. But it’s definitely not enough. I am happy she liked it but I need to change that. I need more. Any suggestions on how to turn her? She’s not into, as she calls it, “fetishy” type stuff  and is also relatively conservative. Can we change that?

Show her that it’s not a fetish, it’s a normal, beautiful, incredibly pleasurable way of sharing intimacy, and that it can make her feel better than anything else. Make her cum from anal enough times and she won’t want it to just be “something special”.

My wife and I both enjoy and have a lot of anal sex and, having spent much time discussing our results and helping interested couples with tips, I’ve put together a blog recently and started to collect some light weight articles to help interested couples with getting from anally curious to anally adventurous.

The focus of the blog is promoting good communication and a mutually beneficial entry into anal for straight couples. While not necessarily a lifestyle blog, we will be writing about our personal experimentation and thoughts in addition to informational writing.

I was hoping you could give us a mention, as I think many of your tumblr fans are the kinds of people who may benefit from our experience to try and gain their partners’ interest in the forbidden fruit.

http://analforcouples.tumblr.com/

Thanks!

The Spartans

Anonymous: I’m a 19 year old girl and I’ve only been doing anal for a few months but I couldn’t agree more. Its so good, I ask my boyfriend for it all the time now!

analk1ng: That’s splendid! Anal really is better for you both. Your boyfriend is a very lucky man – I hope he appreciates you!