Anal? You want anal? Well, have you heard of........
Overview: Lighten up, no matter how pressing your desire for ass fucking may be. Talking, pressuring or coercing your girl into anal isn't effective. Tricking or forcing her into it is out of the question. Pleasuring her into it is a whole different story........
THE BASIC RULE: You must be well-versed in pleasuring the "usual" parts. That's right, you must be handy with a pussy. If you're not already giving your girl heights of orgasmic pleasure like she's never seen, you're not ready for the ass fuck conspiracy. If you're not skilled with her vagina and related parts (and genuinely enjoy being so), there's no way she's letting you near the "other" place. Period. And she has a sense of this, trust me. If this is an issue, go back and figure it out, then proceed only when you've practiced more.
Step #1: Orgasms, orgasms, and more orgasms (for her, duh). If you're providing your girl with many lovely and varied types of O's, she's going to have an inherent trust in your knowledge of and ability in the area of pleasuring her, which is going to make the issue of ass fucking much more considerable. (see above.) Also, for most girls, its more desirable and more pleasurable to do anal if they've already had at least one or several orgasms. More on this below.
Step #2: Oral, oral and more oral. While you're down there showing off your superior oral abilities and facilitating those O's, mix-it up a bit -- flick your tongue, swirl it, and perform oral on and around her asshole. This will not only introduce her to the fact that there are many lovely nerve-endings there, which she will most likely enjoy, but will exhibit the fact that you are adventurous and appreciative of and committed to the pleasure of her entire being. This creates a much different atmosphere then that of completely avoiding her asshole and then trying to stick something in it. You know?
Step #3: The T'aint. "It ain't the pussy and it ain't the asshole." You may have heard of this little place between the pussy and the asshole. If you are enjoying or working up to Step #2, don't forget this little place for licking, etc.
Step #4a: Fingering. There are a couple different sections to the "fingering" step. Fingering begins on, around and in the vulval area (which you know if you've adhered to the Basic Rule). Specific to the ass fuck conspiracy is the fact that inside the vagina itself, there are many special "spots." (Also useful: "mapping" the vaginal anatomy of your particular girl.) You've most likely heard of or are familiar with the "G." Well, did you know there's a "reverse-side G?" It may have its own special name, but I don't remember it right now. Its on the opposite side of the "G" -- that's right, on the wall seperating her pussy from her ass. The "internal t'aint," if you will. This is a special place; special because it feels really good when stimulated -- tickled, rubbed, pressed on, up, down, side to side, circular, you have to experiment a bit to find the right stimulus for your girl. Also special because most girls haven't had lovers who have taken the time to find all their internal special spots, particularly this one, and if you are that special lover then you have already set yourself apart in a really great way. And special because when you are stimulating this little area, you are actually stimulating her asshole, which is your ultimate goal here in the ass fuck conspiracy. Now, if she really responds to the stimulation of this little area, as evidenced by the usual signs specifying heightened pleasure, you should feel really encouraged. You are most likely golden for ass fucking sometime in your very near future. If she's unresponsive, unsure or she out and out doesn't like it, you may have to reconsider your options or at least spend more time on steps 1-3.
Step #4b. Fingering cont'd. At some point, you're going to want to proceed with your superior fingering skills on into her ass. For several reasons. One -- you want to relax that mostly tight, unrelaxed space slowly. You want to open her up in a pleasurable way, not just ram your tool in there. You try one finger --- slowly, see how that goes, then probably two. Most people know this even if they aren't familiar with the secrets of the ass fuck conspiracy. Reason two -- not only are you relaxing the space, you are pleasuring her. You are now in the vicinity of the reverse G -- but now on the other side of the internal t'aint. Are you with me geographically? So, while you're exploring, relaxing and fingering here, your job is to help her enjoy it. While your fingers are in her ass, you are actually stimulating spots in her vagina. Did you know that? In that light, most of your movements should be directed "up," towards her vagina, as opposed to "down," away from it. It turns out, that nature, in her ever-comical way of tripping us up, has actually made some really great pleasure spots in the vagina easier to reach from the asshole. Ha! Funny isn't it? Even more funny since most women won't let you anywhere near their asshole. Right. ha. This is where I should tell you that many women who haven't experienced vaginal orgasms can and will experience "anal" orgasms via this method. Remember -- its because when you are in her ass, you are really stimulating spots in her vagina. Also remember that the internal t'aint (either side) is a very delicate, thin area (although strong, especially if she kegels), so act accordingly -- nothing too rough or jamming, please. Again, you have to experiment a bit to find out just where her great spots are and to what stimulus she responds best. This should be no problem for you, since at this point, having incorporated all of the above, you are a master lover -- adept at reading all the clues from your lover and responding accordingly. Even if she's super-orgasmo girl and regularly has all types of orgasms -- vaginal, clitoral, etc., she may experience orgasms from this like she never has -- rolling, continuous, non-stop, fully body, etc. And she may squirt, or ejaculate. (I'm not going into female ejaculation here, or debating whether its "real" or not, that's a whole other story, I'm just warning you.) Or she may not. She may not like it. She may feel weird. She may feel out of control. She may love it, but she may feel weird or out of control, and hence, want to stop. You are responsible for dealing with these variables. That's just the way it is. Deal with it without whining no matter how much you were "progressing" with the plan and are bummed you can't proceed.
Step #5: Don't forget the clit. Oh-no-siree. While you're doing all that other stuff, encourage her to play with her clit, or you do it with your other hand. Reasons for this are twofold: One, her clit is a pleasure place, and you want a pavlovian-type association going on here. Two -- it will enhance orgasmic possibilities. And/or give her oral. Remeber the orgasm part above? Now's the time to absolutely insure she's having them.
This is a good time to mention THE GOLDEN RULE: Never ass to pussy! Pussy to ass, OK, but don't put anything in any other places after they've been in her ass, it could lead to yucky infections. Keep track of your fingers, designate if you have to.
Step #6: Actual ass fucking. Now, if you're lucky, and all of the above steps have been successful, you may just find that she's asking you to fuck her ass. You should be so lucky. It could happen. Anyway, you may now be ready to put your cock in her ass. There are many ways to go about this, keeping in mind the foundation of lube, limits and pacing as mentioned above. Here are some tips, since much has been written (and can be found) on how to proceed with ass fucking.
Tip #1: Fuck her pussy first. If you haven't already, its good to do this first. Why? well, it feels good, loosens up the entire area (remember, its all very close together), she may have more orgasms, especially given all the above action, its good for lubrication purposes. And its fun.
Tip #2: Be creative with lube. Yes, there's lube in a tube. There are other types -- her juices, your spit, be inventive, use what's there.
Tip #3: You introduce your tool, let her back onto it at her pace, with you facilitating -- gently, slowly, adding a teensy tinsy bit of equal resistance every time she makes a move. This is teamwork -- you adding resistince provides extra sensation, and if she's hesitant and has already demonstrated she likes you to be "in control" or she likes to be led down debaucherous paths, she needs you to keep the pace or she may abort the mission. I know you're excited, I know you're having fun, but keep track of her responses and don't lose her!
Tip #4: Don't forget the clit. Somebody get the clit! Again, as above, pavlovian connection and increased pleasure.
Tip #5: Reverse cowgirl. Most people only think of one or two positions when planning ass fucking, but don't forget "girl on top," it works for anal too. Reverse cowgirl anal gives her control over depth and movement and allows her to experiment and find all the good spots, what feels best to her.
Tip #6: If she's really enjoying it, she may squirt (see above).
Tip #7: A reminder: never ass to pussy! For those set on indulging in this taboo action, you wear a condom and have her wear a female condom, then everyone is safe and you can go back and forth. Otherwise, never ass to pussy unless you wash (thoroughly) or switch condoms. Even if you're not overly concerned about your partner's health (which you should be), think of it this way: even if she loves it, you're not doing it again anytime soon if you give her an infection through sloppy habits. I know its all close together, figure it out.
Tip #8: Safe Word. "Safe word", you say? "We're not S&M types, we don't need a safe word." Well, you might, so come up with one just in case. You see, due to various psycho-social factors as well as thin lines between pleasure and pain, your girl may feel the need to tell you to stop or say no even if she doesn't want you to. And you don't want to stop if you don't have to do you? No, I didn't think so. So, "stop" or "no" are not good safe words. Come up with something else -- "red" or "pickle" or "smurf" or anything at all that doesn't usually come up in a sexual context. Because you DO want to stop if she really wants you to. Not stopping if she really wants you to will completely ruin the ass fuck conspiracy.
Tip #9: She may cry. In case you haven't noticed, girls can be kinda emotional. Just because she cries doesn't (necessarily) mean you hurt her or something. She might cry for any number of reasons -- intense orgasms, emotional release, just because. Hey, she also might laugh. Don't take it personally.
Whew! If you've done all this, you are successfully ass fucking! Congratulations. Proceed as with other fucking and enjoy.
Other considerations: You may have to enact the ass fuck conspiracy over a period of time -- days, weeks, months -- it all depends on the variables of how long you've been together, how open-minded she is, etc. With a girl you haven't been with that long who's never been open to anal, it could take a while. I am in no way implying you can be successful in one session (or at all, for that matter) even if you are the greatest lover on earth. Oh, and the bigger you are, the longer its going to take, sorry. You could be "stuck" at #2 or #4b for quite awhile. Let her know how much you love it, let her enjoy all the fabulous orgasms, let her know in a really sexy way how much fun you're having and how much you really want her ass one day. Naughty mid-day phone calls reminding her of these things don't hurt either. :) Once you actually do it, she may love it but not let you do it that much. She may love it and want you to do it all the time. She may love it and have "issues" about it. She may be worried you're "ruining" her asshole, her virtue, etc. If she starts ejaculating, you may have more laundry to do. She may eventually want to be DP'd, and you may have to buy more toys. More chores and financial investment due to ass fucking!? Who knew? Well, you started it. She may follow you to the ends of the earth for providing such mind-blowing orgasms. More drama may come about in eventual breaking up. ("But I let you fuck my ass!") She may be mad at you for turning her into an anal slut. Ass fucking can be murky territory. These are all your problems to deal with. Good luck.
Endnotes: Yes, I'm a girl. Yes, I enjoy anal. Yes, I used to be a girl who said I'd never let anyone do anything to my ass. Yes, some ass-fucker got me with this plan. It took him a month (and many, many mind -blowing orgasms and naughty mid-day phone calls). No, I wasn't aware of "the plan" at the time; I figured out his evil conspiracy later and I deemed it the "ass fuck conspiracy," he laughed. Yes, we met on cl. Yes, we broke up. Yes, I was mad at him for turning me into an anal slut. Yes, I got over it. Yes, I ejaculate. No, I'm not looking for dates. Bye!