Jackie...Wassup?
Jackie...Wassup Archive
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Somewhere Over The Booty Rainbow

Just what exactly, you might ask, does anal sex have to do with that magical land of Oz? Quite simply, when your tight little asshole is filled with eight inches of hard dick, you know for sure, Toto, that you’re not in Kansas anymore.

For the adventurous, it is. For the timid, missionary-position-with-all-the-lights-off types, it is not. Anal sex is the hottest type of sex I’ve ever experienced. When it’s right, it’s as close as I’ve ever come to an out of body experience. Afterwards, when you’ve really been ass fucked by the best, it’s even a little hard to walk. Is it worth it? Does Nathan Lane sing in the shower?

Anyone familiar with my predeliction for butt fucking invariably asks the same three questions . First and foremost, do I really enjoy taking a hard cock up my tender asshole. Apparently, most people find it impossible to imagine it enjoyable. Number two (no pun intended), how was I ever convinced to allow eight inches of hard dick meat to enter my tight sweet rosebud. Lastly (and always requested with a hint of desperation) I’ve been asked for a step-by-step guide, a how-to manual, if you will, on not only butt-fucking, but convincing the wife or girlfriend that she’s going to like it. I notice these requests never come from women.

Well, I have a few things to say about that. I will readily confess that it was my husbands idea and took some persistence on his part to achieve successful and pleasurable anal sex copulation. The truth is that I’m the type of woman who likes to be led by her sex partner, encouraged to go beyond the mundane boundaries. I really abhor the idea that I might be missing out on something. So if I’m given the right motivation I’m usually up for pushing the sexual envelope. Generally speaking, I’ve found sexual adventurism to be rewarding. I’m certainly no Xavier Hollander. But it has been my experience that anal sex in particular is an acquired pleasure.

An acquired pleasure for women, that is. Not for men. Oh no, men take to ass-fucking like bees to honey, that is, as long as the man is the fucker not the fuckee. The second their dicks make the slide inside the “tight” hole, there’s no looking back. But for women it’s a totally different story. The pleasure is not instantaneous. As a matter of fact, I knew a woman who couldn’t take as much as a Q-tip inside her ass. She told me every time her boyfriend attempted to devirginize her asshole she actually cried tears of pain. Now that’s no way to have fun. Nor is it any motivation for a woman to continue to try.

But for women who are curious and brave enough to push their sexual envelope to include their asshole, I do have a few tips for getting there. A word of warning; there is some pain involved. But hey, Dorothy didn’t get over that rainbow without a little bit of discomfort, either.

Tip # 1) If a woman is dead set against it, forget it. But one way to possibly pique her interest is to talk to her about it during enjoyable and hot sex. Mention how much you’d love to place your cock inside her beautiful sweet asshole. Tell her how much you love to watch her ass move in a tight skirt, how appetizing it is, how it gets you hard instantly. After a few hot sex session with fantasy anal sex talk, she may be open to a little butt-experimentation.

#2) Anal sex should never be attempted without ample foreplay. It just isn’t one of those things that a woman can enjoy unless she’s been fondled, sucked, licked, and played with, and has had at least one orgasm under her belt. I find that after an orgasm my entire body relaxes and yet is still in a state of very high stimulation. Relaxation and stimulation are like the two keys to the anal treasure chest. So my advice is, attempt anal as part of a long and sumptuous feast of totally indulgent sex.

#3) If you drink, I’d suggest a low level of intoxication for the beginner. Sip on a dry and very well chilled martini, or a light and friuty Cotes du Rhone. If you don’t consume alcohol, then a second orgasm before anal penetration wouldn’t be a bad idea. Yeah, the guy has to do a little extra work. But I never said it was easy! Tiger Woods makes it look easy, but do you have any idea how many balls that guy hits before he ever walks on the course?

#4) Eating pussy is the essential precurser to getting a big cock up a tiny butthole. Not only does proficient clit sucking and nibbling loosen up the ass muscles, it’s the perfect time to begin teasing the asshole with both tongue and fingers. I especially enjoy it when my lover is sucking on my clit, finger fucking my pussy, then slides his wet fingers down and begins gently inserting a finger inside my ass. At first, only up to the first joint, then he slides it out again. He might slip his tongue down to my ass and lick it for a while, pressing his tongue inside my ass a little, then sliding his tongue back up to my clit while his fingers start playing with me again. Just at the point of my first orgasm he’ll slide his finger all the way inside my ass as waves or orgasm wash over my body. It’s such a rush to the senses, it’s almost like skiing in the Sierras. Except warmer. And you’re not nearly as likely to break your leg.

#5) Lube, lube, lube. Lots of it. We like AstroGlide. The point is, don’t ever attempt to fuck anyone’s asshole without lots and lots of lube. Ouch!

#6) Timing. The right time is when a woman has reached orgasm, her asshole has been fondled and she’s extremely well lubricated. Another thing to remember is position. The more relaxed my ass muscles are for initial penetration the more fun it’s going to be. So I like to put my legs up over my partner’s shoulders while I lay on my back at the edge of the bed. He is standing and has great access to my ass. Sometimes we’re both on the bed and he’s on his knees. Either way, I find penetration works easiest for me in this position. And easy initial penetration is vital to successful anal sex because...

#7) ...Usually it’s gonna hurt for about a minute. Now, pain is subjective. And it’s not horrible pain. More like discomfort. The point here is that the discomfort passes as the muscles relax and accept that big cock that just slid into your ass. Somtimes, if I’m really stimulated and relaxed, I feel no discomfort at all. I don’t know why, but my guess is that the more stimulated you are, the more endorphins are pumping through your body and the faster you get to the good part.

#8) Don’t ever confuse ass fucking with pussy fucking. Totally different animals. I enjoy the proverbial sport fuck, in other words, when a guy fucks your cunt so hard and fast that he gets his cardio workout for the month. But anal sex is the Yoga of fucking. Slow, methodical, meditational. And once the woman is past the “initializing” period it’s like flying, when the pilot says, “you’re free to walk about the cabin.” In fact, one of the most amazing positions for anal sex is doggy style, I’ve found. But as I said, power butt-fucking I wouldn’t recommend.

I guess the reason I enjoy anal so much is the way that it heightens the experience of sex. Takes it to a different plane where every touch, every french kiss, every stroke of a hand on your back feels amplified about 100 times when a cock is inside your tender asshole. Somehow, and I don’t know why exactly, I feel closer with my lover during anal sex than any other sex act. Maybe because it’s so taboo and you feel like you’re partners in the same sinfully carnal crime. Maybe because it takes you to a place that’s over the rainbow without the necessity of mind altering drugs. So if you’ve ever wondered, “Oh, why, oh, why can’t I?” now you know how.

Let me know how it works out!