Anal sex can be painful if you don't know what you are doing, and nobody initially knows. But if you do proper anal training upfront, anal will always be pleasurable and you'll crave for more!
After 20 hours of research and crowdsourcing hundreds of people experiences I compiled all the best people tips, helpful stories and positions in one place:
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How To Prepare For Anal Sex?
The first time me and my girl did it, we simply talked about it… read a little bit on safety precautions…and playfully went for it!
All it took was a condom on my finger, lots of lubrication and slow, patient anal massage…till the butt-hole opened for a nice entrance…
The best position to do it was doggy style… and I got immense pleasure from fucking her vaginally while having my finger in her butt-hole.
I was incredibly hard and horny just from the idea of doing something dark and kinky… and her pussy felt way tighter than she usually does..
In fact, I felt my finger in her ass while my cock was in her.
I loved it…
She loved it too and quickly orgasmed while rubbing her clit.
Soo.. that's it… That's all the preparation there was…
But it's not that easy…
There are sometimes emotional blocks from the past both for man or woman.
I took me a while to accept myself touching my butt as a straight male hah!
And it took a while for her to accept that I loved her pussy and ass..!
She had insecurities around her intimate parts and it took a long time and many repeated times of compliments for her to relax and open up… and believe that her pussy and ass was indeed super sexy for me!
Steps To Follow For Successful Anal Play
If I needed to break it down to steps I would say:
- talk about it with your partner and get her/him comfortable and open with the idea
- take a shower, do enema, whatever to get yourself clean
- get yourself relaxed, hell, drink a glass of wine if it helps
- get a nice anal lube (Sliquid Sassy is the most loved across hundreds of anal players)
- get to it — massage the anus gently…and slowly insert the finger…
- if you've got butt-plugs, anal beads..use them.
- if you've got prostate massager (for men) use it
- if you've got penis that you wanna use — stretch the butt for that…!
Just know all of this takes time… Butt sex is not a fast process.
It takes time for your butt, rectum to relax and open up.
Further Anal Training Tips From Other People
“So just so general things: don’t eat beforehand or during meeting the person. “
“It stops poop from accumulating.
Buy an enema, preferably a bulb type and about a hour or 2 before hand, clean out your intestinal track.
You should practice using it before hand to get use to it and know how it works.
Try to get the water coming out clear.
And buy something to warm up (stretch) your asshole. A butt plug or a dildo should do (and lube).
The first time stretching might hurt if done too fast or too hard so you want to be prepared and make sure you do it yourself, you don’t want to go have sex with the guy and him not warm you up before hand.
But this is just a precaution because if you just shove anything of any reasonable size up there really fast, be prepared for some real bad pain.
Again these are just some general things and precautions, so go have some fun!”
Source: MrCheese67
“Should I try anal sex?"
“Try some anal play first, would be my suggestion.
Don’t go from nothing to a dick in your Ass.
That’s… quite a transition to make.
But keep an open mind about it, and just try a few things to start out with.
It’s a different kind of pleasure than vaginal sex.
See if you like it before going all the way, but never be afraid to try new things.”
Source: SleepingTigress
“Butt plugs will help. Fingering helps. Silicone lube is a must. “
“Make sure you have pooped a few hours in advance.
If you have to poop it will hurt A LOT worse. Even after all of that my boyfriend still hurts me too.
He must go slow.
I have to breathe and relax because if you tense your ass it will hurt more.
The only position I’m comfortable is with him laying on my back with his face next to my face.
I think that relaxes me because he’s like pushing me down almost.
You should try that position!”
Source: Anonymous
“Anal Pleasures: My wife wants to start experimenting with butt sex. Got any advice?”
“Lube. More lube. Still more lube.
Best position: doggy with you kneeling (or standing off the bed) perfectly still, allowing her to move and adjust as she needs to.
When it gets to be too much, let her pull completely away, relax and start again after a brief break.
DO NOT THRUST until she tells you to.
You can also lie down on your back and let her cowgirl (straight or reverse) until she’s comfortable, then ride you at her own pace.”
Source: ReallyEvilCanine
“Use a sex toy or your fingers to loosen her up a little.
Helps a lot when it comes time to insert your hot man sausage.
Oh, and did we mention lube?”
Source: andrewhy
“Fingers first, one then two. “
“If it hurts at all you stop for a bit and wait for a few mins then try again.
Don’t grit your teeth and power through the pain, keep stopping and starting.
Take your time. It’s not supposed to hurt.”
Source: Anonymous
“Tell her to use her rectum to push on your equipment, (the same action as is required for pooping), instead of trying to draw it in (which makes her clench and is much more painful for her.)
Also, lube cannot be mentioned enough.
Lastly, inform her that if she wants a little reprieve, she can put her hands behind her and make space as she needs to in order to get used to it.
Allowing her to control the pace is huge for her having a good experience.”
Source: Tbone139
“Be gentle, but remember, once you’re all up in that shit, it’s an amazing experience that you can just let loose and go buck wild with.”
Use lube.
A lot of people say use a lot of lube, but in reality, you don’t need to use a whole bottle every time you pack her fudge.
Do NOT be afraid to lick her asshole before fucking it.
Unless, of course, there are dingleberries lurking about.
Anyhow, women love this.
In fact, you’ll probably love it too.
Be prepared, eventually she will be swallowing your sword, and she’ll lift it up and lick under your balls, your taint, and let her tongue venture to your asshole.
It feels great.
It’s NOT gay.
Well, maybe it is, but only if it’s a dude licking your asshole.
Enjoy it. It’s a lot of fun.”
Source: mrp
“A few things come to mind as to how to get better butt sex…”
First, check the lube.
Find a high quality lube without a lot of additives.
Believe or not, some people have issues with the popular lubes like Astroglide and others.
They contain things that can cause cramping, faster bowel movements and so on.
So be sure you look for a lube without glycerin and for some people, without parabens.
Take a gas pill a few hours beforehand.
Something like gas X/phazyme can help keep gas bubbles from forming down there.
May or not help much but can’t hurt.
Try to get some practice with a small toy or one around his size, a few times a week by yourself.
Throw a condom on it if you’re worried about cleanliness and ease of cleanup if you don’t want to rinse out before toys.
Don’t be afraid to go to the bathroom just after and try to push some of the air out. If he comes all the way out and back in a lot you can build up some air in the rectum.
Lastly, if you’re using condoms, try a non-latex one in case that’s an issue for you.
Something like Lifestyles Skyn (they’re non-latex polyisoprene synthetic latex, but NOT natural skin so they’re fine against pregnancy and disease prevention) are good to use for those with latex allergies.”
Source: Isimagen
The Best Anal Toys For Anal Training?
The best is to start small and avoid "eyes bigger than the hole" mistake.
Best is to buy an affordable anal training kit with various size toys that allow to ease in to actual penis size anal sex.
I love this Lovehoney Bumper Kit:
Toys are made from silicone, there is a vibrating bullet to experiment with different kinds of pleasure, and douching bolb.
This kit will last you a long time.
This helpful video reviews some of the best various anal toys:
Do Women Like Anal Sex? What does Anal Feel like?
Women answer:
“Statistics show that 36% of women have tried anal sex.”
“I’m a woman into anal sex.
It’s a pleasurable pressure to me, and I absolutely adore the dominating and forbidden nature of the act.
I wouldn’t have sex with anyone I didn’t personally find attractive though…
Most of my female friends haven’t tried it.
The few that have often state it feels like a reverse bowel movement or express that it hurts.
Only one is into it like me.”
Source: MissKinkykittykat
“The fullness, The naughtiness and it just feels amazing.”
“For me it just feels amazing. Clitoral stimulation is definitely an added benefit but anal alone feels good. “
“I haven’t cum from anal alone but it feels good enough that maybe one day I’ll cross that threshold.
There are women who definitely do cum from anal alone though.
To compare vaginal and anal sex is hard.
They both feel different.
If I had to choose I would choose vaginal any day but sometimes it’s just nice to switch things up.
It’s more of a heat of the moment thing for me.
I am feeling so good that I just want it in my ass too.”
Source: ladylonglegs22
“So my husband and I just recently breeched the anal sex thing and I absolutely love it. “
“He’s been wanting to for 5 years and while we were doggy style the other night he put his finger in my ass and I begged him to put his dick in.
It instantly made me orgasm.
It’s all I can think about now.
We just finished another round tonight.
I love everything about it.
That it’s just between us, the pressure, the mind blowing stimulation, the fact that he loves it, the fact that there is a dick in my ass.
The fact that I can feel him cum inside of me and know I can’t get pregnant again, just everything.
Can’t wait until tomorrow so we can do it again. 
”
Source: mmmmm1993
“Butt sex stimulates the same spot that vaginal sex does, just from a different angle. “
“I rub my clit during anal sex it gives me the best, most intense orgasm.
That’s why I don’t care for cunnilingus.
Clitoral stimulation alone is boring, compared to the combination of clit stimulation and some intense fucking in either orifice.
This is from someone who can only cum clitorally.”
Source: HappySubbie
“I don’t like full anal sex but I do like butt play. “
“I like a finger in the ass or a butt plug.
I like the fullness, the naughtiness, how it makes his cock feel even more intense for piv sex, and being submissive to him.”
Source: throwitaway1596
“My girlfriend can come from anal penetration alone, as could one of my ex’s. “
“The skin barrier between vagina and anal cavity are paper thin in some spots, and sometimes the nerves are actually closer to the surface in the rear, from my understanding.
It just depends on the woman's body.”
Bringing It All Together
Hope this advice from many people will help you to kick some butt with your first butt sex experience (pun intended) 
After your first experience make sure you read more how to have an anal orgasm (for women) or how to massage prostate (for men).
And you gotta read the rimming guide (how to eat ass).
Cheers! 