Recently 'deflowered' an anal virgin. One of many anal-agnostic (and anti-anal) women - and she was a hard case. Literally went from "NO BUTT STUFF" to "stick it in nowwww."
With a few very exceptional exceptions, most women aren't thrilled with the idea of ass-play, at first brush.
Chalk it up to any number of things, including cultural conditioning ("it's bad and dirty, and I don't want to do things that sluts do,") personal presuppositions (again, "it's bad and dirty and I don't want to do things that sluts do") , bad past experiences ("wrong hole!" or "it hurts!") or anecdotes about bad past experiences heard from others...there are a lot of women who are weird about anal.
But despair not! I'm good at making women want to bend over and spread their cheeks for me, and willing to share what works for me (And avoid the court date you can anticipate following the horrible, impractical advice others have offered!).
I have a pretty reliable system. Here are its fundaments:
Don't Be A Scumbag!
If she doesn't at least trust you a little, anal's off the table. Don't stick it in dry. Don't try to surprise her, don't try to pressure or guilt her into it. Self-explanatory, but part of the challenge of convincing a woman to take it in the ass is disabusing her of the notion that anal is bad because some idiot came along before you and ****ed up and ruined her perception of it.
Don't Pay Attention At First
Before you even as much as touch on the idea, you want your gal so well-banged that she's feeling loose and ready for anything. You want her a couple of orgasms deep.
Yes, yes, I hear what you're saying now: "But GhostApe, I wanna fvck her in the ass..." Well, we'll get to that. Have some patience, you goddam ape.
If she hasn't gotten off at least once or twice and/or her ***** hasn't been subjected to least 15-20 minutes of cumulative pounding, the odds are low that she's going to agree to anal. And if you can't meet either of those criteria, or if they seem unreasonable, you have no business trying to convince a woman to let you fvck her in the ass anyway.
What you want to do is get her horny, wet and at least partly satisfied. Women are way easier to convince to do kinkier crap when they're into what's already going on. I've upgraded from vanilla to choking/spanking/bondage with women, and it always happens a solid half-hour into the encounter.
LUBE
I shouldn't need to make a separate subhead for this, but here we are. Unless you've got a 4-inch, finger-thick penis (and I doubt anyone here will admit to that anyway), you're going to need a lot of lubrication.
Stop trying to 'surprise' her with anal, and stop assuming "she'll just loosen up" after a few strokes.
Part of the reason women are so resistant to taking it in the brown is because there are men trying to do dry anal with them, or not adequately prepping.
If you belong to that category, cut that out, stop ruining women on anal for the rest of us, you imbeciles.
This isn't a porno shoot. If you want to fvck her in the ass you need patience and willingness to probe around with a finger to the get the lube IN her.
Also, you want a good, quality lube, so open your wallets, already. Stop trying to grease the skids for some wild bacchanalia you've seen on Brazzers that you want to act out with her, with cheapo-depot K-Y jelly from the drug store.
There's a plethora of good quality lube out there that won't dry out five strokes in. Yes, it will cost money, but you're paying for quality here.
The As(s)k
There's no real knack to this. Eventually, you've got to show interest.
It can be at anytime. I've brought it up on O.L.D. conversations, texting, I've asked during coitus, I've mentioned it with FWBs on the second or third meeting. Your mileage may vary but you're generally going to get responses that fall into three general categories.
1. YES: Proceed with lube and ass-fingering, foreplay, gently insert and work your way up to crazy porno stuff. Enjoy, you goddamn sodomite.
2. NO: There's more variation to this one than you think. And it depends on the severity of the 'no.' The last woman I ass-fvcked was a hard no for months. She and I were an on-again-off again FWB situation and I didn't want to push it. So I didn't.
But then, a month or two in, she started hitting the gym and her ass grew - and I wanted to put my penis in it.
How did I turn a hard no into an enthusiastic yes? I worked my way up. Slowly amp up the spanking; Notice her ass, by complimenting and and drawing a lot of attention to it.
Amp up the spanking more. Eat her out and spank her while you eat her out - eat her out from behind.
Eventually, with the hard-case I converted, I moved onto "hot dogging" my shaft up and down the cleft of her ass, alternating between that and pounding her ***** in the same position.
This builds associations, and, since I was taking it slowly. I also was able to show her that I was patient enough to literally stimulate my junk, rubbing it between her ass-cheeks without trying to ram it into her rectum.
Eventually, I'd set the mood by lowering the lights (lower inhibitions), running through that "work up" I just described and putting on some music that gets her going. This led to her getting worked up over the feeling of how engorged I was, going between her ass cheeks with my junk, hot-dog style, and she started to get turned on by how turned on I was.
It was all a simple coast downhill from that point. I fingered her slowly, tickling the outside "rim," until she was warmed up enough to take a finger. Lube goes on, finger goes in, and just work her until she's ready. Eventual, slow insertion, as she throws back her head and ... yeah you get the rest.
CAVEAT: My point here isn't to suggest it's a practical or realistic thing to wait months to fvck a woman in the ass. I'm just saying it's possible to turn even the hardest no into a yes, consensually, if you're patient.
I could have sped up the timeline by taking some of those bolder steps later, but again, this was a long-term FWB situation and I didn't even really want to bang her in the ass until it grew. (I presume she learned how to squat in the gym, bless her heart.)
3. MAYBE SO:
Honestly, just do what you did for the hard-no, but do it on a speedier timeline.
"Maybes" are far rarer than yeses or nos, when it comes to anal. It's a pretty polarizing subject.
