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The Ass Instructional
Saturday, January 10, 2004
Apparently I need to write a really thorough instructional guide on how to get your girlfriend to take it in the ass. I've seen and read lots of instructionals on this, one video including knocking your girl silly with a rock to the head. Fortunately, my Ass Instructional will limit the region of pain and humiliation. And who better to help me than the guy who took my ass-ginity?

Ok, darling, on a scale of one to ten, how difficult was it to let you fuck my ass?

Hmm . . .you seemed willing. But more than hesitant. You disliked the first time, but were still willing to do more. I'm sure you just felt some sort of pity for me.
Ok, now what numerical value is that?
I'd say it was . . . oh . . . a 4. And it's really only a 4 now because of the way things have turned out. Otherwise I'd say 6.
Are you calling me easy?
No, you were just willing to try it. I didn't think you seemed to keen on the idea. You didn't really like it. But you did it anyway.
Well, if you'd never had anal sex before, why did you want it with me?
Cause I wanted to have anal sex, I wanted to try it. It looked like fun.
So what's the difference between sex in my pussy and sex in my ass?
Pussy and ass. Hmm well . . . it's different. That's the big thing; it's a variation, a change and change is good.
Admit it, you liked anal sex better than regular sex, you perve.
It felt better. Tighter, a little bit warmer. That and it was anal sex. Just the idea.
Then why fuck my pussy at all?
Because I enjoyed fucking all of you.  Anal sex was like a treat.
You're so sweet.
I'm not sure how else to explain it.
Can you try at least?
Well . . . slamming your beautiful poon was like . . . filet mingon; anal sex was . . . like . . . Otoro Sushi. Not a meal in itself, something different but still of equal quality.
Ok . . . what about when we stopped using condoms . . . didn't that gross you out?
Nah. Simple rule. Why stick my tongue where I wouldn't stick my dick?
Yeah, I know. But you were totally ok with it?
Yup, 100 percent. I hate condoms, they hurt like hell when they would break.
What about with analingus? Did you want that as much as you wanted to fuck my ass?
I'm not 100 percent sure why. But I LOVE! licking your ass. Licking your ass . . . well . . . god. How to describe it. It's like anal sex . . . but much more intimate. Burying my face, feeling you squirm.
Mmmmm indeed. The great thing about licking your ass . . . is that I didn't need foreplay to start doing it, not like cunnilingus. That required a startup.
Why is that? Isn't it the same thing?
It is. But you didn't need to be wet to enjoy analingus.
I have to be wet for you to eat me?
It helps. A lot.
Really? I didn't know that.
So what would you suggest for other guys? How should they go about it? Besides fucking me that is?
I didn't really strain myself trying to convince you . . . you were willing to try. I don't think anal sex is something that you can force on the unwilling. Unless, of course, they're unconscious.
Yeah, we saw the rock on the head approach . . . more pain than necessary.
Ah yes. I still have that movie on my computer. Direct honest approach. Sneaky WHOOPS approach. Then hit her with a brick. Ahh . . . so many fond memories of you just minding your own business and me just Bliztkrieging your ass.
Hehe, those times were wonderful.
Yeah, you'd just bend over and I'd pull you down and go to work.
You think it's worth it for both the guy and the girl or am I just a supreme freak?
I'd say it's worth it. The guy gets something awesome out of it. And if the girl ends up enjoying it . . . well, if you are any example . . . it'll be great for both parties.
But I doubt I'm an example. I'm just an exception.
Who knows.

Step 1: Getting Her Reacquainted With Her Ass
If you're not already grabbin' her ass 24/7, I suggest you do so now. The more attention you shower on that booty, the more she will recognize that it is a formidible sexual object. Touch it, grab it, knead it. Let her know you love it. Compliment it and when you're kissing her, reach down and give it a little squeeze. The objective of this is to get her used to her ass being involved with sex, so it won't be so awkward and uncomfortable or nearly as dirty when you both decide to take the plunge.

Step 2: Broaching The Subject of Anal Intrusion

Of course, not all women will be thrilled or at all enthusiastic into letting you into her ass. It's her ass! However you choose to broach the subject, ingratiate yourself to her. Think about what you are asking and how you would react if it was she were asking you to get up in there, so have some humility. She will, at first, be experiencing some pain for your pleasure. I suggest doing something satisfying to her, sexual or not. This is in no way meant to make her feel obligated if you do; instead, it will be a swapping of sexual favors, where one partner definitely recieves and the other really gives. Think of it thusly: You must first prostrate yourself before she prostrates herself. My partner just asked me and I relented, feeling very obligated to do it out of love and knowing that, eventually, I would be worn down. If he had taken me out to dinner, drawn a bubble bath and washed me, gave me a body massage followed by oral, I would have been much more willing to give it up.

Whatever you do, don't try anal in an "oops situation." You know what I mean, guys. "I couldn't find the right hole" or "it slipped." Also, don't do it when you're both drunk and horny, thinking she would be less likely to remember. We're not stupid. Our assholes don't scream from pain on a daily basis. So do me a favor and swallow the fear of rejection and just ask your girl. It's a trust and understanding thing, way over your heads.

Step 3: Practice Makes Perfect

Like my ex said, "Why stick my tongue where I wouldn't stick my dick?" That's right boys, I'm asking you to stick your tongue down there. You've already asked to fuck it with your dick, why don't you get more intimate with that area of her body? Do some serious research on it before you get to stick it in. Here's what I want you to do: Don't just turn her 'round and start making out with her ass. Spend lots of time on oral, making frequent trips south to probe her ass with your tongue. That way she gets a connection of pleasure when you eat her ass because you were also eating her out. "I hear keeping the pad of your thumb over the anus while performing cunnilingus is a good way to get a woman comfortable," my ex adds. Be gentle, don't stab your tongue in and out. If you want her to be the most comfortable she can be during your first time with as less pain as possible, do this. When you've done these preliminaries and she's comfortable with analingus, take her in doggie position, lube up your pointer finger and gently slide it in. At first you may use only the first knuckle of the finger but when she gets used to it, her sphincter will relax, letting room for a whole finger or two to enter. Don't stretch it or finger it fast; just let her know what having something in her ass feels like. Of course while you're doing this, you're fucking her good, right? Multitask! I don't recommend buying a butt plug at this point. Some suggest it, but if anal intercourse fails, it will only serve as a sour reminder. And if you are new to toys, it's just another thing to get used to. The whole reason people suggest it is because they hope it will make the anus ready for anal intercourse. The smooth tapered sides of my butt plug feels nothing like a cock in my ass. The only thing to get you ready for real anal intercourse is real anal intercourse.

My first experience was unbelievably awkward and a little bit humiliating. I describe taking it in the ass for the first time as taking this enormous dump where someone keeps pushing the rewind and play button, over and over and over. You end up gritting your teeth and trying to take as much as you possibly can before you whimper to your partner to stop. That was when I was very inexperienced and in the shower. I had no idea what to do and I wasn't in a very comfortable situation (which I apparently dropped the soap in). But I learned to love it.

Step Four: One Small Plunge For Man . . .
Ok, you've prepared and prepared and set a date to actually do this. Lube within reach? Long foreplay? Lots of oral? Good. Now, without either of you cumming, fuck her good vaginally. Get her to the point where she's working up a lather, foam is around her mouth, and truthfully, anything at this point is bound to feel good. She'll give you the cue, and if she doesn't, next time then. If she does choose to take the plunge, contain your excitement because it is imperative that you go slow and cautiously. Put on a rubber. Apply lubrication liberally. Again, another suggestion, don't use the numbing lubrications. I guess I'm a fan of natural and raw feelings in intercourse, but the pain and uncomfort she feels now will be the pleasure she will feel later. I guarantee that. Probe her hole with your head, it actually feels damn good. Don't barge in there when you do get a go-ahead, but enter slowly. The head, for me, was the most uncomfortable part of anal sex at first - besides the whole dick up your ass thing. When my ex would pull out somewhat, I could feel his huge head against me, stretching me. It wasn't too pleasant; I enjoyed the feeling of his shaft but didn't welcome the approach of his head. Get in there and go slowly, sinking in even slower. And when you get to the hilt of your cock, all nestled inside her, stop and let her get used to something so filling. This can take a few minutes because the entrance is followed by an intense and acute burning. Staying in and staying put allows that burning to go away. Now, at this point, don't do anything. It's all up to her. She knows what's good and what's not, let her take control. She will slide up and down your pole with as much speed and intensity as she can take it, so let her and don't try to "help." If you're seeking pleasure, you will have it, just don't get her to loathe anal sex. If you've got a vibrator or other such device, I suggest that you use it. Clitoral stimulation is very important. It allows her to feel pleasure and also distracts her from the pain, resulting in a more relaxed anus. If you do not have a vibrator, either reach down and finger that clit, or ask her to do it herself, because it really does help. Keep going slow, your orgasm is not important this session. And if you do, pull out. Crapping out your semen doesn't help the humiliation of the first time.

Step Five: Rinse And Repeat

Hopefully the first time went well. You can't really force someone to like anal sex, it's more of an acquired taste, like caviar and champagne. It helps to have a loving and interested partner, who will take the time with you to do it and do it with less of an asshole attitude, but a loving, caring approach. I daresay that you can only completely enjoy anal sex if both partners enjoy it, tapping into pleasures undreamt of. So, fuck her ass again. It will get less painful and lots more enjoyable as time goes on. In fact, it was so good that for one whole month, that's all what my ex and I were doing, and some of it was real hardcore fucking. Once both of you are comfortable with it, take the condom off and enjoy the sensations it gives you. It really makes a marked difference, the rubber making the cock slippery and easy to slide in. Going "bareback" as they say, the only way I'll take it now, offers incredible sensations. And if you can, orgasm and then stick it in her ass, the cum making a lubricant more heady than any manufactured. Having done that recently, where he actually came twice before entering my ass, it slipped right in as if it belonged there, not as it should have, which was an end to a very long dry spell. God, that feels so good, let me tell you. Better yet, experience it for yourself.

Step Six: And Once Anal Intercourse Becomes Vanilla . . .

Once it gets to be pleasurable and finally, happily, anal sex becomes the norm of your sex life, what do you do to spice it up? There's an array of toys you can implement. Vibrating butt plugs, Ben Wa balls or otherwise known as anal beads, wands, jelly dongs, even a strap on specifically designed for penetrating the orifice you aren't busy with. You can mix it up with bondage or domination, any variation, but anal sex should never be boring. And for the very daring couples I could suggest things that deal with compersion, trust, and love. But that is another desire of mine and therefore another entry for later.

I hope you have enjoyed my Ass Instructional. If you did get to follow along and all was successful, then happy day! If not, well, don't feel too bad. There are other kinks to be had, most of which I can introduce you to. If you were successful and it was because of this instructional, I would love to hear about it and congratulate you.

As always, have fun and be safe. Go ass!

Posted at 08:37 am by Deanna.

October 21, 2006   11:25 AM PDT
Muffera wants me to have buttsecks with her. That is all.
June 5, 2004   09:55 AM PDT
You wouldn't be too excited if it was the first time your ass would be penetrated :P
June 5, 2004   09:54 AM PDT
Scott: Stop thinking about it and do it already..
June 5, 2004   09:53 AM PDT
Hi. My name is Scott, and me and my girl are now thinking of anal sex. It was actualy completely her idea, and I am for it. I read your articlel on it and it helped.

I just wanted to say thank you.
March 26, 2004   04:53 PM PST
did you know that poop comes out of the ass?
February 12, 2004   07:58 PM PST
Chicks who dig getting boned in the ass rule
January 21, 2004   08:07 AM PST
i've always wanted to try anal, but the guy i was with was too cowardly to try that stuff-therefore im still an anal virgin. anyways,i liked ur blog entry! i dunno why i told you about my ass tho.cya!
January 21, 2004   08:03 AM PST
Peo- I wanted to thank you. After reading your blog I tried anal with my girlfriend. Just as you said...she wasn't sure then exploded in pleasure. We are converted perverts...thanks.

My girlfriend now wants to try multiple input now that she is crazy over anal sex. Any advise?

January 12, 2004   02:03 PM PST
If there's anything I am not, it's lazy. When it comes to sex that is. That's why it's Fuck 101 . . .
January 12, 2004   01:19 PM PST
My girl knows I like ass...I do not take this for granted, as many people do not seem so lucky.
January 12, 2004   01:11 PM PST
If I ran a school, I would hire you. It's almost funny how much thought you put into this.

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